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Gumroad,
with Sahil Lavingia
From Silicon Vally hype to mass layoffs, and the tactics that helped Gumroad grow to their $100M
valuation
Tactician
Case
Interview:
001
http://www.Tactician.Tech
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PRESERVERENCE
What role preserverence played
in Gumroad's journey to its
$100M valuation
BUILDING IN PUBLIC
How BIP has helped Gumroad to
attract the right talent, eliminate
meetings, and raise $5m in 12
hours
Topics Explored
MARKET SIZING
How size of market constrained
Gumroad's early growth, and how
founders can avoid building in
small markets
Sahil was born in the US, grew up in Singapore, then moved back to the US to study
Computor Science at the University of Southern California. He dropped out to
become Pinterest's second hire and built their iOS app, then left to start Gumroad in
2011 at the age of 19. He manages an investment fun with LPs that include Marc
Andreeseen, Naval Ravikant, Elad Gil, and Tim Ferris, and has invested in Clubhouse,
HelloSign, Notion, and Figma.
Meet Sahil
Meet Gumroad
Gumroad helps content creators (ex. musicians, writers, filmmakers, photographers,
etc.) sell digital products (ex. online courses, memberships, etc.) directly to their
audiences. They monetize by charging a fee on each transaction and a $10 monthly fee
to "Pro" account holders
o Founded in 2011: Silicon Vally, USA
o $16.1M raised
o >40 employees
o $100M valuation as of August, 2021
Origin Story:
http://www.Tactician.Tech
Origin Story (1/6)
o In high school, Sahil fell in love with building and selling
digital products on the internet.
o From a young age, he admired Bill Gates and aspired to
build his own billion-dollar company.
Origin Story (2/6)
o He moved to the US for college, but dropped out at the
age of 18 when he recieved an offer from Pinterest to
build their iOS app and became their second employee.
Origin Story (3/6)
o Less than one year into his role at Pinterest, Sahil had
designed an icon and wanted to sell it to his followeers on
Twitter, but realized the process of selling was more
difficult than it should be.
o He built the first version of Gumroad over a weekend to
solve that problem, and launched on Hacknews, landing at
the #1 spot for the day.
o With the hypothesis that over time more individuals and
companies will want tools to sell directly to the audiences
they build on social media and other platforms, he believed
he was on to something.
Origin Story (4/6)
o He quit Pinterest shortly after (before vesting his
equity), and raised a Seed round from Silicon Valley
stalworths such as SV Angel, Max Levchin, Chris Sacca,
and Josh Kopelman.
o Before launching the product, the venture fund Kleiner
Perkins offered Sahil a pre-emptive $7m Series A
investment.
Origin Story (5/6)
o Gumroad made good headway in its first three years,
however, the company did not grow fast enough to
raise a Series B
o After hundreds of unfruitful meetings with investors,
Sahil eventually laid off his entire team of 20 and
continued as a solo entreprenure, eventually moving to
Utah to decompress and find direction
Origin Story (6/6)
o Gumroad is now a $100m company that employs 40
people
Shahil plans to use the funding to xxxxxxxxx
The future
At $12 annualized revenue, Gumroad raised a
$5m crowdfunded round within 12 hours
2021: $5M equity crowdfunding
The first layoff took the company from 20
people down to 5. The second took the
compnay from 5 to Shail as the only employee.
He moved from Silicon Valley to Utah in 2017,
looked for ways to process his experience, and
continued working on Gumroad
2015: Layoffs begin
Gumroad grew by close to 60% in 2016, 15% in
2017. In 2018 Sahil begain shipping features
and hiring for the first time since the final
layoffs and grew 25%, then 40% in 2019 and
87% in 2020
Continued growing the business
Their 60-80% YoY growth wasn't the 3x growth
Series B investors look for. Kleiner did a $2m
bridge is 4x liquidation pereference
2014-2015: Struggled to raise
Series B
At 19 years old, raised a $1.1M seed round.
Soon after raised a pre-emptive $7M Series A
from Kleiner Perkins
2011: Raised Seed and Series A
Timeline
Key Challange:
Market Sizing
http://www.Tactician.Tech
Top down is a less reliable way to estimate the size of a market alone, but using it with bottoms
up analysis to triangulate, or sanity check your numbers can help you get a more accurate size
of the market, and convince others.
Investors at the earliest stages when there is less information, are more aminable to top down
analysis. Aim to make the methodology used as clear as possible (ex. its common for investors
to hear: "the market is $xB. If we get 10% of that, it could be $y!"... what are the assumptions
that justify the ability to get 10%?)
Considerations:
2 Important considerations when determining the market size for something fundamentally new
Ways To Think ABout Market Size, by Benedict Evans
1 Step by step guide to determining the size of your market, in the context of pitching VC's
Market Sizing: Framing the Opportunity, by Maximilian Bruhn
Recommended Reading:
3 Why market size matters, when you should do analysis, and how to go about it
Market Sizing Guide, by Pear VC
Sahil:
"...we had a few success cases where marquee folks – authors – made $300 000 in a year, which,
as an author, is pretty crazy. We really felt we were going to be able to replicate this: If we had
1000 authors – that didn’t seem like too many – that’s $300 million a year. And then we realized,
slowly, there were not that many of those authors...
It doesn’t matter how awesome your product is, or how awesome your team is, or how often
you ship features; the market you’re in is going to determine most of your growth...
And often, you don’t really think about: How big is the market? How many people need this?
How much money do they have, or are they willing to spend, on this sort of thing? So, I think it’s
really important to spend time thinking a bit more about the market... Early adopters are often
your best customers, and it is impossible to predict how many of them are out there until you
start analyzing....
If we believe there are 50… or 5,000, lets make a list of all of them.”
According to Sahil, the size of the creator market was the biggest limiter of Gumroad's early growth: there
were fewer creators, and the LTV of each was smaller than expected. Ideniftying this earlier could have helped
them to target a better segment, or pivot to a new market
There are two ways startus can determine the size of their market to avoid suprises:
02
Bottoms up method
Find the number of customers. Multiply that by the average revenue per
customer per year
MARKET SIZING
01
Top down method
Broad industry market size (usually provided by a research company)
multiplied by a target % of ownership. Less accurate as broad reseach rarely
excludes segments that arn't targeted
o According to Sahil, the size of the creator market was
Gumroad's biggest limiter in its early growth: there were
fewer creators, which meant fewer customers, and the
LTV of each was smaller than expected
o Identiftying this earlier could have helped them to target a
better segment, or pivot to a new market
MARKET SIZING (1/6)
Top down is a less reliable way to estimate the size of a market alone, but using it with bottoms
up analysis to triangulate, or sanity check your numbers can help you get a more accurate size
of the market, and convince others.
Investors at the earliest stages when there is less information, are more aminable to top down
analysis. Aim to make the methodology used as clear as possible (ex. its common for investors
to hear: "the market is $xB. If we get 10% of that, it could be $y!"... what are the assumptions
that justify the ability to get 10%?)
Considerations:
2 Important considerations when determining the market size for something fundamentally new
Ways To Think ABout Market Size, by Benedict Evans
1 Step by step guide to determining the size of your market, in the context of pitching VC's
Market Sizing: Framing the Opportunity, by Maximilian Bruhn
Recommended Reading:
3 Why market size matters, when you should do analysis, and how to go about it
Market Sizing Guide, by Pear VC
Sahil:
"...we had a few success cases where marquee folks – authors – made $300 000 in a year, which,
as an author, is pretty crazy. We really felt we were going to be able to replicate this: If we had
1000 authors – that didn’t seem like too many – that’s $300 million a year. And then we realized,
slowly, there were not that many of those authors...
It doesn’t matter how awesome your product is, or how awesome your team is, or how often
you ship features; the market you’re in is going to determine most of your growth...
And often, you don’t really think about: How big is the market? How many people need this?
How much money do they have, or are they willing to spend, on this sort of thing? So, I think it’s
really important to spend time thinking a bit more about the market... Early adopters are often
your best customers, and it is impossible to predict how many of them are out there until you
start analyzing....
If we believe there are 50… or 5,000, lets make a list of all of them.”
According to Sahil, the size of the creator market was the biggest limiter of Gumroad's early growth: there
were fewer creators, and the LTV of each was smaller than expected. Ideniftying this earlier could have helped
them to target a better segment, or pivot to a new market
There are two ways startus can determine the size of their market to avoid suprises:
02
Bottoms up method
Find the number of customers. Multiply that by the average revenue per
customer per year
MARKET SIZING
01
Top down method
Broad industry market size (usually provided by a research company)
multiplied by a target % of ownership. Less accurate as broad reseach rarely
excludes segments that arn't targeted
Going after an attractive market is considered by many to be the most important thing you can
do (even more important than the quality of your team, or your product).
As Marc Andreessen (Andreessen Horowitz, Co-Founder) puts it:
"… in a terrible market, you can have the best product in the world and an absolutely killer team,
and it doesn’t matter—you’re going to fail...
You’ll break your pick for years trying to find customers who don’t exist for your marvelous
product, and your wonderful team will eventually get demoralized and quit, and your startup will
die.
… assuming the team is baseline competent and the product is fundamentally acceptable, a great
market will tend to equal success and a poor market will tend to equal failure."
MARKET SIZING (2/6)
Top down is a less reliable way to estimate the size of a market alone, but using it with bottoms
up analysis to triangulate, or sanity check your numbers can help you get a more accurate size
of the market, and convince others.
Investors at the earliest stages when there is less information, are more aminable to top down
analysis. Aim to make the methodology used as clear as possible (ex. its common for investors
to hear: "the market is $xB. If we get 10% of that, it could be $y!"... what are the assumptions
that justify the ability to get 10%?)
Considerations:
2 Important considerations when determining the market size for something fundamentally new
Ways To Think ABout Market Size, by Benedict Evans
1 Step by step guide to determining the size of your market, in the context of pitching VC's
Market Sizing: Framing the Opportunity, by Maximilian Bruhn
Recommended Reading:
3 Why market size matters, when you should do analysis, and how to go about it
Market Sizing Guide, by Pear VC
Sahil:
"...we had a few success cases where marquee folks – authors – made $300 000 in a year, which,
as an author, is pretty crazy. We really felt we were going to be able to replicate this: If we had
1000 authors – that didn’t seem like too many – that’s $300 million a year. And then we realized,
slowly, there were not that many of those authors...
It doesn’t matter how awesome your product is, or how awesome your team is, or how often
you ship features; the market you’re in is going to determine most of your growth...
And often, you don’t really think about: How big is the market? How many people need this?
How much money do they have, or are they willing to spend, on this sort of thing? So, I think it’s
really important to spend time thinking a bit more about the market... Early adopters are often
your best customers, and it is impossible to predict how many of them are out there until you
start analyzing....
If we believe there are 50… or 5,000, lets make a list of all of them.”
According to Sahil, the size of the creator market was the biggest limiter of Gumroad's early growth: there
were fewer creators, and the LTV of each was smaller than expected. Ideniftying this earlier could have helped
them to target a better segment, or pivot to a new market
There are two ways startus can determine the size of their market to avoid suprises:
02
Bottoms up method
Find the number of customers. Multiply that by the average revenue per
customer per year
MARKET SIZING
01
Top down method
Broad industry market size (usually provided by a research company)
multiplied by a target % of ownership. Less accurate as broad reseach rarely
excludes segments that arn't targeted
A market's attractiness is dictated by its size and growth rate, competition and customer
dynamics.
Low switching cost, low barriers to entry, cheap customers are all bad for business
However, innovation (in product, channel, etc.) can create new markets, increase
switching cost and render competition moot.
The greater your intention, available capital, and team's competency for innovation, the
less important to focus on competitive forces in evaluating a market.
MARKET SIZING (3/6)
Top down is a less reliable way to estimate the size of a market alone, but using it with bottoms
up analysis to triangulate, or sanity check your numbers can help you get a more accurate size
of the market, and convince others.
Investors at the earliest stages when there is less information, are more aminable to top down
analysis. Aim to make the methodology used as clear as possible (ex. its common for investors
to hear: "the market is $xB. If we get 10% of that, it could be $y!"... what are the assumptions
that justify the ability to get 10%?)
Considerations:
2 Important considerations when determining the market size for something fundamentally new
Ways To Think ABout Market Size, by Benedict Evans
1 Step by step guide to determining the size of your market, in the context of pitching VC's
Market Sizing: Framing the Opportunity, by Maximilian Bruhn
Recommended Reading:
3 Why market size matters, when you should do analysis, and how to go about it
Market Sizing Guide, by Pear VC
Sahil:
"...we had a few success cases where marquee folks – authors – made $300 000 in a year, which,
as an author, is pretty crazy. We really felt we were going to be able to replicate this: If we had
1000 authors – that didn’t seem like too many – that’s $300 million a year. And then we realized,
slowly, there were not that many of those authors...
It doesn’t matter how awesome your product is, or how awesome your team is, or how often
you ship features; the market you’re in is going to determine most of your growth...
And often, you don’t really think about: How big is the market? How many people need this?
How much money do they have, or are they willing to spend, on this sort of thing? So, I think it’s
really important to spend time thinking a bit more about the market... Early adopters are often
your best customers, and it is impossible to predict how many of them are out there until you
start analyzing....
If we believe there are 50… or 5,000, lets make a list of all of them.”
According to Sahil, the size of the creator market was the biggest limiter of Gumroad's early growth: there
were fewer creators, and the LTV of each was smaller than expected. Ideniftying this earlier could have helped
them to target a better segment, or pivot to a new market
There are two ways startus can determine the size of their market to avoid suprises:
02
Bottoms up method
Find the number of customers. Multiply that by the average revenue per
customer per year
MARKET SIZING
01
Top down method
Broad industry market size (usually provided by a research company)
multiplied by a target % of ownership. Less accurate as broad reseach rarely
excludes segments that arn't targeted
o There are two ways startups can determine the size of
their market to avoid suprises:
MARKET SIZING (4/6)
Top down is a less reliable way to estimate the size of a market alone, but using it with bottoms
up analysis to triangulate, or sanity check your numbers can help you get a more accurate size
of the market, and convince others.
Investors at the earliest stages when there is less information, are more aminable to top down
analysis. Aim to make the methodology used as clear as possible (ex. its common for investors
to hear: "the market is $xB. If we get 10% of that, it could be $y!"... what are the assumptions
that justify the ability to get 10%?)
Considerations:
2 Important considerations when determining the market size for something fundamentally new
Ways To Think ABout Market Size, by Benedict Evans
1 Step by step guide to determining the size of your market, in the context of pitching VC's
Market Sizing: Framing the Opportunity, by Maximilian Bruhn
Recommended Reading:
3 Why market size matters, when you should do analysis, and how to go about it
Market Sizing Guide, by Pear VC
Sahil:
"...we had a few success cases where marquee folks – authors – made $300 000 in a year, which,
as an author, is pretty crazy. We really felt we were going to be able to replicate this: If we had
1000 authors – that didn’t seem like too many – that’s $300 million a year. And then we realized,
slowly, there were not that many of those authors...
It doesn’t matter how awesome your product is, or how awesome your team is, or how often
you ship features; the market you’re in is going to determine most of your growth...
And often, you don’t really think about: How big is the market? How many people need this?
How much money do they have, or are they willing to spend, on this sort of thing? So, I think it’s
really important to spend time thinking a bit more about the market... Early adopters are often
your best customers, and it is impossible to predict how many of them are out there until you
start analyzing....
If we believe there are 50… or 5,000, lets make a list of all of them.”
According to Sahil, the size of the creator market was the biggest limiter of Gumroad's early growth: there
were fewer creators, and the LTV of each was smaller than expected. Ideniftying this earlier could have helped
them to target a better segment, or pivot to a new market
There are two ways startus can determine the size of their market to avoid suprises:
02
Bottoms up method
Find the number of customers. Multiply that by the average revenue per
customer per year
MARKET SIZING
01
Top down method
Broad industry market size (usually provided by a research company)
multiplied by a target % of ownership. Less accurate as broad reseach rarely
excludes segments that arn't targeted
MARKET SIZING (5/6)
01
Top down method:
The number of customers that exist (usually found in broad industry
research) multiplied by what you expect to earn off each customer. For
example, imagine your company sells learning resources to schools. Your
research shows 10,000 relevant schools in your country, and your average
sale per school is $10k, which means your market size is $100M.
Although top down is simple, it is often unreliable and overly optimistic.
Not EVERY school needs your product, and perhaps not all would take your
$10k package.
Top down is a less reliable way to estimate the size of a market alone, but using it with bottoms
up analysis to triangulate, or sanity check your numbers can help you get a more accurate size
of the market, and convince others.
Investors at the earliest stages when there is less information, are more aminable to top down
analysis. Aim to make the methodology used as clear as possible (ex. its common for investors
to hear: "the market is $xB. If we get 10% of that, it could be $y!"... what are the assumptions
that justify the ability to get 10%?)
Considerations:
2 Important considerations when determining the market size for something fundamentally new
Ways To Think ABout Market Size, by Benedict Evans
1 Step by step guide to determining the size of your market, in the context of pitching VC's
Market Sizing: Framing the Opportunity, by Maximilian Bruhn
Recommended Reading:
3 Why market size matters, when you should do analysis, and how to go about it
Market Sizing Guide, by Pear VC
Sahil:
"...we had a few success cases where marquee folks – authors – made $300 000 in a year, which,
as an author, is pretty crazy. We really felt we were going to be able to replicate this: If we had
1000 authors – that didn’t seem like too many – that’s $300 million a year. And then we realized,
slowly, there were not that many of those authors...
It doesn’t matter how awesome your product is, or how awesome your team is, or how often
you ship features; the market you’re in is going to determine most of your growth...
And often, you don’t really think about: How big is the market? How many people need this?
How much money do they have, or are they willing to spend, on this sort of thing? So, I think it’s
really important to spend time thinking a bit more about the market... Early adopters are often
your best customers, and it is impossible to predict how many of them are out there until you
start analyzing....
If we believe there are 50… or 5,000, lets make a list of all of them.”
According to Sahil, the size of the creator market was the biggest limiter of Gumroad's early growth: there
were fewer creators, and the LTV of each was smaller than expected. Ideniftying this earlier could have helped
them to target a better segment, or pivot to a new market
There are two ways startus can determine the size of their market to avoid suprises:
02
Bottoms up method
Find the number of customers. Multiply that by the average revenue per
customer per year
MARKET SIZING
01
Top down method
Broad industry market size (usually provided by a research company)
multiplied by a target % of ownership. Less accurate as broad reseach rarely
excludes segments that arn't targeted
MARKET SIZING (6/6)
02
Bottoms up method
Identify the specific segments you will target, source a list of potential
customers, multiply by the expected revenue per customer.
The distiction here is that you've made a specific list of customers. Not
only can bottoms up be more accurate than top down, it can also help
identify and list customers to target
Generally, earlier stage investors are amenable to top down. By Series A
aim to be able to do bottoms up
"...we had a few success cases where marquee folks – authors – made $300,000 in a
year, which as an author, is pretty crazy. We really felt we were going to be able to
replicate this: If we had 1000 authors – that didn’t seem like too many – that’s $300
million a year. And then we realized, slowly, there were not that many of those authors...
It doesn’t matter how awesome your product is, or how awesome your team is, or how
often you ship features; the market you’re in is going to determine most of your growth...
And often, you don’t really think about: How big is the market? How many people need
this? How much money do they have, or are they willing to spend, on this sort of thing?
So, I think it’s really important to spend time thinking a bit more about the market... Early
adopters are often your best customers, and it is impossible to predict how many of
them are out there until you start analyzing....
If we believe there are 50… or 5,000, lets make a list of all of them.”
"...we had a few success cases where marquee folks – authors – made $300,000 in a
year, which as an author, is pretty crazy. We really felt we were going to be able to
replicate this: If we had 1000 authors – that didn’t seem like too many – that’s $300
million a year. And then we realized, slowly, there were not that many of those authors...
It doesn’t matter how awesome your product is, or how awesome your team is, or how
often you ship features; the market you’re in is going to determine most of your growth...
And often, you don’t really think about: How big is the market? How many people need
this? How much money do they have, or are they willing to spend, on this sort of thing?
So, I think it’s really important to spend time thinking a bit more about the market... Early
adopters are often your best customers, and it is impossible to predict how many of
them are out there until you start analyzing....
If we believe there are 50… or 5,000, lets make a list of all of them.”
"Placehodler for comment from Elizabeth. Lorem ipsum delor.”
Elizabeth Yin
GP @Hustle fund
2 Important considerations when determining the market size for something fundamentally new
Ways To Think ABout Market Size, by Benedict Evans
1 Step by step guide to determining the size of your market, in the context of pitching VC's
Market Sizing: Framing the Opportunity, by Maximilian Bruhn
Recommended Reading:
3 Why market size matters, when you should do analysis, and how to go about it
Market Sizing Guide, by Pear VC
The Only Thing That Matters, by Marc Andreeseen
Why the market is more important then team and product for startups
4
Key Challange:
Surviving the "Trough of
Sorrow"
http://www.Tactician.Tech
“If you join Gumroad, my goal is that you learn almost nothing new on the day you join. The
revenue and everything you should have known, you could know right now by Googling it, which I
think is really important. I don’t want anyone to join the company and realize this is not the right
fit…
I make it really clear that I don’t like telling people what to do. I do that in the hiring process,
before the hiring process, on a jobs page, afterwards… So, hiring is definitely the largest part of it
– making sure you’re hiring the right kind of folks who can operate in this way – and that’s
mostly a function of being really clear with people and letting them self-select out.
Ultimately, the hardest thing – and I think the reason a lot of people may want to work this way
but eventually won’t – is that it requires a really high bar of hiring. I interview hundreds of people
for some roles...”
Sahil:
2 Reddal provides a case study on one company's approch to getting out of the TOS and gives advice on how to
think about pivoting
Tech startups can minimize their time in the trough of sorrow with a zoom-in pivot
1 Andrew Chen provides both emotional and tactical advice on how to manage, and exit the TOS
After the Techcrunch bump: Life in the “Trough of Sorrow”
Recommended Reading:
3 Brain Balfour shares the most important characteristic of his company that got his startup out of the TOS
How We Got Through The Trough Of Sorrow
There are two widely discussed considerations for not building in public:
o Increased competiton: businesses with little barrier to entry, those in competetive markets
should weigh the upside of BIP with the asymitry of information they'll create for their
competition
o Increased scrutiny: negetive signaling (several months of high churn, revenue dips, etc) can
damage customer, investor and your team's perception of the viability of the businss
Considerations:
There are four essential "fits" a startup needs to reach
in order to scale:
Product/Market Fit → Does your product satisfy demand?
Product/Channel Fit → Products are built to fit marketing/growth channels. Can you
product leverage a particular channel to scale?
Channel/Model Fit → how you charge (freemium, transactional, free trial, one year
upfront, etc.) and how much you earn from customers dictates what channels can provide
profitable growth. Does your business model fit said channel?
Model/Market Fit → There need to be enough customers at your average revenue per
customer to create a big business
SURVIVING THE TROUGH OF SORROW (1/6)
In competing for talent, Gumroad’s competitive advantages are flexibility and efficiency. Gumroad's team doesn't hold
meetings, eliminating time wasted on coordination
o Tweeting and writing about his experience and experiments building this unique culture attracts applicants (50-30
interviews per engineer hire)
o Those applicants have self selected into Guhmroad’s unique work environment and plan: candidates are aligned to
the work culture, state of the business’ financials, mission and vision before they start work, creating a highly
engaged and motivated team
1. Creating an efficient work culture
“If you join Gumroad, my goal is that you learn almost nothing new on the day you join. The
revenue and everything you should have known, you could know right now by Googling it, which I
think is really important. I don’t want anyone to join the company and realize this is not the right
fit…
I make it really clear that I don’t like telling people what to do. I do that in the hiring process,
before the hiring process, on a jobs page, afterwards… So, hiring is definitely the largest part of it
– making sure you’re hiring the right kind of folks who can operate in this way – and that’s
mostly a function of being really clear with people and letting them self-select out.
Ultimately, the hardest thing – and I think the reason a lot of people may want to work this way
but eventually won’t – is that it requires a really high bar of hiring. I interview hundreds of people
for some roles...”
Sahil:
2 Reddal provides a case study on one company's approch to getting out of the TOS and gives advice on how to
think about pivoting
Tech startups can minimize their time in the trough of sorrow with a zoom-in pivot
1 Andrew Chen provides both emotional and tactical advice on how to manage, and exit the TOS
After the Techcrunch bump: Life in the “Trough of Sorrow”
Recommended Reading:
3 Brain Balfour shares the most important characteristic of his company that got his startup out of the TOS
How We Got Through The Trough Of Sorrow
There are two widely discussed considerations for not building in public:
o Increased competiton: businesses with little barrier to entry, those in competetive markets
should weigh the upside of BIP with the asymitry of information they'll create for their
competition
o Increased scrutiny: negetive signaling (several months of high churn, revenue dips, etc) can
damage customer, investor and your team's perception of the viability of the businss
Considerations:
- The challenge Sahil faced was
model/market fit: that there didn't
seemed to be enough customers for the
business model to create a large, fast
growing company
- That situation of post-launch slow
growth is often referred to as the Trough
of Sorrow. Sahil spent (arguably) 8 years
there and in "Wiggles of False Hope"
-What got him out was perseverance - ie.
not allowing the company to die so that
he could:
SURVIVING THE TROUGH OF SORROW (2/6)
In competing for talent, Gumroad’s competitive advantages are flexibility and efficiency. Gumroad's team doesn't hold
meetings, eliminating time wasted on coordination
o Tweeting and writing about his experience and experiments building this unique culture attracts applicants (50-30
interviews per engineer hire)
o Those applicants have self selected into Guhmroad’s unique work environment and plan: candidates are aligned to
the work culture, state of the business’ financials, mission and vision before they start work, creating a highly
engaged and motivated team
1. Creating an efficient work culture
Coined by Paul Graham, Co-Founder of Y Combinator
“If you join Gumroad, my goal is that you learn almost nothing new on the day you join. The
revenue and everything you should have known, you could know right now by Googling it, which I
think is really important. I don’t want anyone to join the company and realize this is not the right
fit…
I make it really clear that I don’t like telling people what to do. I do that in the hiring process,
before the hiring process, on a jobs page, afterwards… So, hiring is definitely the largest part of it
– making sure you’re hiring the right kind of folks who can operate in this way – and that’s
mostly a function of being really clear with people and letting them self-select out.
Ultimately, the hardest thing – and I think the reason a lot of people may want to work this way
but eventually won’t – is that it requires a really high bar of hiring. I interview hundreds of people
for some roles...”
Sahil:
2 Reddal provides a case study on one company's approch to getting out of the TOS and gives advice on how to
think about pivoting
Tech startups can minimize their time in the trough of sorrow with a zoom-in pivot
1 Andrew Chen provides both emotional and tactical advice on how to manage, and exit the TOS
After the Techcrunch bump: Life in the “Trough of Sorrow”
Recommended Reading:
3 Brain Balfour shares the most important characteristic of his company that got his startup out of the TOS
How We Got Through The Trough Of Sorrow
There are two widely discussed considerations for not building in public:
o Increased competiton: businesses with little barrier to entry, those in competetive markets
should weigh the upside of BIP with the asymitry of information they'll create for their
competition
o Increased scrutiny: negetive signaling (several months of high churn, revenue dips, etc) can
damage customer, investor and your team's perception of the viability of the businss
Considerations:
o Learn and iterate: time, and diligent
studing of customers has lead the team
to re-segment and target higher value
customers with product offering he
believes has lower competition, and
launch a membership product which fules
most of the current revenue growth.
SURVIVING THE TROUGH OF SORROW (3/6)
In competing for talent, Gumroad’s competitive advantages are flexibility and efficiency. Gumroad's team doesn't hold
meetings, eliminating time wasted on coordination
o Tweeting and writing about his experience and experiments building this unique culture attracts applicants (50-30
interviews per engineer hire)
o Those applicants have self selected into Guhmroad’s unique work environment and plan: candidates are aligned to
the work culture, state of the business’ financials, mission and vision before they start work, creating a highly
engaged and motivated team
1. Creating an efficient work culture
“If you join Gumroad, my goal is that you learn almost nothing new on the day you join. The
revenue and everything you should have known, you could know right now by Googling it, which I
think is really important. I don’t want anyone to join the company and realize this is not the right
fit…
I make it really clear that I don’t like telling people what to do. I do that in the hiring process,
before the hiring process, on a jobs page, afterwards… So, hiring is definitely the largest part of it
– making sure you’re hiring the right kind of folks who can operate in this way – and that’s
mostly a function of being really clear with people and letting them self-select out.
Ultimately, the hardest thing – and I think the reason a lot of people may want to work this way
but eventually won’t – is that it requires a really high bar of hiring. I interview hundreds of people
for some roles...”
Sahil:
2 Reddal provides a case study on one company's approch to getting out of the TOS and gives advice on how to
think about pivoting
Tech startups can minimize their time in the trough of sorrow with a zoom-in pivot
1 Andrew Chen provides both emotional and tactical advice on how to manage, and exit the TOS
After the Techcrunch bump: Life in the “Trough of Sorrow”
Recommended Reading:
3 Brain Balfour shares the most important characteristic of his company that got his startup out of the TOS
How We Got Through The Trough Of Sorrow
There are two widely discussed considerations for not building in public:
o Increased competiton: businesses with little barrier to entry, those in competetive markets
should weigh the upside of BIP with the asymitry of information they'll create for their
competition
o Increased scrutiny: negetive signaling (several months of high churn, revenue dips, etc) can
damage customer, investor and your team's perception of the viability of the businss
Considerations:
2. Take advantage of unpredictable
favorable events: He rode the small
but steady growth of the creator market
over a perioed of 10 years and managed
to bing in perfect position to capitalize
on the spike in 2020 that resulted from
COVID-19.
SURVIVING THE TROUGH OF SORROW (4/6)
In competing for talent, Gumroad’s competitive advantages are flexibility and efficiency. Gumroad's team doesn't hold
meetings, eliminating time wasted on coordination
o Tweeting and writing about his experience and experiments building this unique culture attracts applicants (50-30
interviews per engineer hire)
o Those applicants have self selected into Guhmroad’s unique work environment and plan: candidates are aligned to
the work culture, state of the business’ financials, mission and vision before they start work, creating a highly
engaged and motivated team
1. Creating an efficient work culture
“If you join Gumroad, my goal is that you learn almost nothing new on the day you join. The
revenue and everything you should have known, you could know right now by Googling it, which I
think is really important. I don’t want anyone to join the company and realize this is not the right
fit…
I make it really clear that I don’t like telling people what to do. I do that in the hiring process,
before the hiring process, on a jobs page, afterwards… So, hiring is definitely the largest part of it
– making sure you’re hiring the right kind of folks who can operate in this way – and that’s
mostly a function of being really clear with people and letting them self-select out.
Ultimately, the hardest thing – and I think the reason a lot of people may want to work this way
but eventually won’t – is that it requires a really high bar of hiring. I interview hundreds of people
for some roles...”
Sahil:
2 Reddal provides a case study on one company's approch to getting out of the TOS and gives advice on how to
think about pivoting
Tech startups can minimize their time in the trough of sorrow with a zoom-in pivot
1 Andrew Chen provides both emotional and tactical advice on how to manage, and exit the TOS
After the Techcrunch bump: Life in the “Trough of Sorrow”
Recommended Reading:
3 Brain Balfour shares the most important characteristic of his company that got his startup out of the TOS
How We Got Through The Trough Of Sorrow
There are two widely discussed considerations for not building in public:
o Increased competiton: businesses with little barrier to entry, those in competetive markets
should weigh the upside of BIP with the asymitry of information they'll create for their
competition
o Increased scrutiny: negetive signaling (several months of high churn, revenue dips, etc) can
damage customer, investor and your team's perception of the viability of the businss
Considerations:
Here are his recommendations for what to do if
you find yourself there:
SURVIVING THE TROUGH OF SORROW (5/6)
In competing for talent, Gumroad’s competitive advantages are flexibility and efficiency. Gumroad's team doesn't hold
meetings, eliminating time wasted on coordination
o Tweeting and writing about his experience and experiments building this unique culture attracts applicants (50-30
interviews per engineer hire)
o Those applicants have self selected into Guhmroad’s unique work environment and plan: candidates are aligned to
the work culture, state of the business’ financials, mission and vision before they start work, creating a highly
engaged and motivated team
1. Creating an efficient work culture
“If you join Gumroad, my goal is that you learn almost nothing new on the day you join. The
revenue and everything you should have known, you could know right now by Googling it, which I
think is really important. I don’t want anyone to join the company and realize this is not the right
fit…
I make it really clear that I don’t like telling people what to do. I do that in the hiring process,
before the hiring process, on a jobs page, afterwards… So, hiring is definitely the largest part of it
– making sure you’re hiring the right kind of folks who can operate in this way – and that’s
mostly a function of being really clear with people and letting them self-select out.
Ultimately, the hardest thing – and I think the reason a lot of people may want to work this way
but eventually won’t – is that it requires a really high bar of hiring. I interview hundreds of people
for some roles...”
Sahil:
2 Reddal provides a case study on one company's approch to getting out of the TOS and gives advice on how to
think about pivoting
Tech startups can minimize their time in the trough of sorrow with a zoom-in pivot
1 Andrew Chen provides both emotional and tactical advice on how to manage, and exit the TOS
After the Techcrunch bump: Life in the “Trough of Sorrow”
Recommended Reading:
3 Brain Balfour shares the most important characteristic of his company that got his startup out of the TOS
How We Got Through The Trough Of Sorrow
There are two widely discussed considerations for not building in public:
o Increased competiton: businesses with little barrier to entry, those in competetive markets
should weigh the upside of BIP with the asymitry of information they'll create for their
competition
o Increased scrutiny: negetive signaling (several months of high churn, revenue dips, etc) can
damage customer, investor and your team's perception of the viability of the businss
Considerations:
o Get clear on what needs to be: (a) proven, (b)
accomplished, (c) by when - to get to the next stage (i.e.
profitability or next funding round), and be sure to give
yourself as much runway as possible.
o Consider setting a "red alert" – deadline, by which to start
exploring pivots if you are still not getting appropriate
traction.
o Test and prove your hypothesis of the value delivered by
your product through customer targeting, customer
acquisition and retention until you find the path out... or
pivot.
SURVIVING THE TROUGH OF SORROW (6/6)
In competing for talent, Gumroad’s competitive advantages are flexibility and efficiency. Gumroad's team doesn't hold
meetings, eliminating time wasted on coordination
o Tweeting and writing about his experience and experiments building this unique culture attracts applicants (50-30
interviews per engineer hire)
o Those applicants have self selected into Guhmroad’s unique work environment and plan: candidates are aligned to
the work culture, state of the business’ financials, mission and vision before they start work, creating a highly
engaged and motivated team
1. Creating an efficient work culture
"One thing I definitely think we should have done was to say: We’re
always going to have more than 18 months of runway, which means that
if we get to two years we need to stop hiring people. It’ like red alert. We
had a lot of optimism in the market – and maybe in 2020 that was
proven out – and we felt it was going to take a lot of time for these
verticals to develop; that we just had to exist long enough...
Because of the lack of red alert, we didn’t have the capacity to really do
anything. We had a couple of experiments; we had a bunch of things we
tried in the last nine-month sprint. We shipped a bunch of features, but
we just didn’t have the capacity, the team or the energy at that time to
build a totally new product from scratch."
2 Reddal provides a case study on one company's approch to getting out of the TOS and gives advice on how to
think about pivoting
Tech startups can minimize their time in the trough of sorrow with a zoom-in pivot
1 Andrew Chen provides both emotional and tactical advice on how to manage, and exit the TOS
After the Techcrunch bump: Life in the “Trough of Sorrow”
Recommended Reading:
3 Brain Balfour shares the most important characteristic of his company that got his startup out of the TOS
How We Got Through The Trough Of Sorrow
4 Brain Balfour shares the most important characteristic of his company that got his startup out of the TOS
How We Got Through The Trough Of Sorrow
Key Opportunity:
Build in Public
http://www.Tactician.Tech
Startups "build in public" (BIP) by sharing aspects of their journey (obstacles, tips,
metrics, learnings, resources, process, etc.) publicly.
BUILD IN PUBLIC (1/8)
BUILD IN PUBLIC (2/8)
An emerging trend that has exploded in popularity since 2018, there are three
audiences:
o Customers: people interested in your product
o Observers: people interested in your process (fellow entrepreneurs, media,
potential hires, potential investors)
o Yourself: keep yourself accountable
Examples:
BUILD IN PUBLIC (3/8)
Product Hunt gathers feedback on design from Twitter followers
Buffer makes revenue, staff salaries, etc. public
Third example, Third example, Third example, Third example
Fourth example, Fourth example, Fourth example, Forthe example
BUILD IN PUBLIC (4/8)
Why BIP?
o To build an audience
o Market to/monetize an
audience
o Increase engagement, buy-in,
trust
o To keep yourself accountable
o To validate ideas/get feedback
o To share knowledge/ help
others
o To build a network/support
group
What to share:
o Teach what you've learned
o Share stats
o Celebrate milestones
o Share failures
o Outline plans
o Ask questions / seek feedback
Where to share:
o Social media
o Blog
o BIP platforms/communities
How to do it?
o Syncronously: build in isolation
and tell the world about it when
you are ready
o Asyncronously: speak to your
audience while building
Top down is a less reliable way to estimate the size of a market alone, but using it with bottoms
up analysis to triangulate, or sanity check your numbers can help you get a more accurate size
of the market, and convince others.
Investors at the earliest stages when there is less information, are more aminable to top down
analysis. Aim to make the methodology used as clear as possible (ex. its common for investors
to hear: "the market is $xB. If we get 10% of that, it could be $y!"... what are the assumptions
that justify the ability to get 10%?)
Considerations:
2 Important considerations when determining the market size for something fundamentally new
Ways To Think ABout Market Size, by Benedict Evans
1 Step by step guide to determining the size of your market, in the context of pitching VC's
Market Sizing: Framing the Opportunity, by Maximilian Bruhn
Recommended Reading:
3 Why market size matters, when you should do analysis, and how to go about it
Market Sizing Guide, by Pear VC
Sahil:
"...we had a few success cases where marquee folks – authors – made $300 000 in a year, which,
as an author, is pretty crazy. We really felt we were going to be able to replicate this: If we had
1000 authors – that didn’t seem like too many – that’s $300 million a year. And then we realized,
slowly, there were not that many of those authors...
It doesn’t matter how awesome your product is, or how awesome your team is, or how often
you ship features; the market you’re in is going to determine most of your growth...
And often, you don’t really think about: How big is the market? How many people need this?
How much money do they have, or are they willing to spend, on this sort of thing? So, I think it’s
really important to spend time thinking a bit more about the market... Early adopters are often
your best customers, and it is impossible to predict how many of them are out there until you
start analyzing....
If we believe there are 50… or 5,000, lets make a list of all of them.”
According to Sahil, the size of the creator market was the biggest limiter of Gumroad's early growth: there
were fewer creators, and the LTV of each was smaller than expected. Ideniftying this earlier could have helped
them to target a better segment, or pivot to a new market
There are two ways startus can determine the size of their market to avoid suprises:
02
Bottoms up method
Find the number of customers. Multiply that by the average revenue per
customer per year
MARKET SIZING
01
Top down method
Broad industry market size (usually provided by a research company)
multiplied by a target % of ownership. Less accurate as broad reseach rarely
excludes segments that arn't targeted
Sahil has leveraged BIP to raise funding, and improve the
performance of his team:
BUILD IN PUBLIC (5/8)
"The benefit of building in public is that you have an audience, so when you launch your product,
you’ve already seeded the idea in everyone’s head and everyone’s ready for it, which is important. The
downside is that it’s embarrassing – it’s public embarrassment. The trick is realizing that no-one cares
about your failure; everyone’s just impressed that you tried – and that’s another important lesson.
You’ll be rewarded for trying...
Thinking about Gumroad as a set of opinions that I have has been really helpful in terms of marketing
the business... saying, ‘We have this set of opinions around how to build a company or how to work’ –
is compelling to people. The crowd-funding, for example, happened in large part because people are
interested in Gumroad as a business and as an experiment that they want to support...
I also think that being public about the Gumroad’s story made it a company that people want to win.
It’s like watching a movie like Rocky: you want to root for the underdog... I’m sure there are at least a
few creators who leaned into that and used Gumroad purely for that reason."
Sahil:
2 One of the key players behind the movement on its origins and benefit
The Transparency Movement: Why It's Important, Buffer Blog
1 Sahil on how
No Meetings, No Deadlines, No Full-Time Employees, Sahil Lavingia
Recommended Reading:
3 Actionable guide to building in public
The Building in Public How-To Guide, Gaby Goldberg
There are two widely discussed considerations for not building in public:
o Increased competiton: businesses with little barrier to entry, those in competetive markets
should weigh the upside of BIP with the asymitry of information they'll create for their
competition
o Increased scrutiny: negetive signaling (several months of high churn, revenue dips, etc) can
damage customer, investor and your team's perception of the viability of the businss
Considerations:
o In March, 2021, the SEC increased the limit startups can
raise through crowdfunding from $1M to $5M
o Sahil saw this as an opportunity to not only raise capital,
but also "blur the lines between investor and customer" by
creating super fans or spokespeople for the company by
raising funding from his audience
Raising $5M in 12 hours
BUILD IN PUBLIC (6/8)
"The benefit of building in public is that you have an audience, so when you launch your product,
you’ve already seeded the idea in everyone’s head and everyone’s ready for it, which is important. The
downside is that it’s embarrassing – it’s public embarrassment. The trick is realizing that no-one cares
about your failure; everyone’s just impressed that you tried – and that’s another important lesson.
You’ll be rewarded for trying...
Thinking about Gumroad as a set of opinions that I have has been really helpful in terms of marketing
the business... saying, ‘We have this set of opinions around how to build a company or how to work’ –
is compelling to people. The crowd-funding, for example, happened in large part because people are
interested in Gumroad as a business and as an experiment that they want to support...
I also think that being public about the Gumroad’s story made it a company that people want to win.
It’s like watching a movie like Rocky: you want to root for the underdog... I’m sure there are at least a
few creators who leaned into that and used Gumroad purely for that reason."
Sahil:
2 One of the key players behind the movement on its origins and benefit
The Transparency Movement: Why It's Important, Buffer Blog
1 Sahil on how
No Meetings, No Deadlines, No Full-Time Employees, Sahil Lavingia
Recommended Reading:
3 Actionable guide to building in public
The Building in Public How-To Guide, Gaby Goldberg
There are two widely discussed considerations for not building in public:
o Increased competiton: businesses with little barrier to entry, those in competetive markets
should weigh the upside of BIP with the asymitry of information they'll create for their
competition
o Increased scrutiny: negetive signaling (several months of high churn, revenue dips, etc) can
damage customer, investor and your team's perception of the viability of the businss
Considerations:
o 12 hours after going live on Republic.co, he raised $5M from
7,303 investors (in $100 to $1,000 cheque sizes)
o Nearly 2,300 were customers of Gumroad and a large portion
of the rest were followers of his BIP journey
o As crowdfunding becomes more prevelant, an additonal
benefit to BIP is leveraging your audience to finance your
business
Raising $5M in 12 hours
BUILD IN PUBLIC (7/8)
"The benefit of building in public is that you have an audience, so when you launch your
product, you’ve already seeded the idea in everyone’s head and everyone’s ready for it,
which is important. The downside is that it’s embarrassing – it’s public embarrassment.
The trick is realizing that no-one cares about your failure; everyone’s just impressed that
you tried – and that’s another important lesson. You’ll be rewarded for trying...
Thinking about Gumroad as a set of opinions that I have has been really helpful in terms
of marketing the business... saying, ‘We have this set of opinions around how to build a
company or how to work’ – is compelling to people. The crowd-funding, for example,
happened in large part because people are interested in Gumroad as a business and as
an experiment that they want to support...
I also think that being public about the Gumroad’s story made it a company that people
want to win. It’s like watching a movie like Rocky: you want to root for the underdog... I’m
sure there are at least a few creators who leaned into that and used Gumroad purely for
that reason."
"The benefit of building in public is that you have an audience, so when you launch your product,
you’ve already seeded the idea in everyone’s head and everyone’s ready for it, which is important. The
downside is that it’s embarrassing – it’s public embarrassment. The trick is realizing that no-one cares
about your failure; everyone’s just impressed that you tried – and that’s another important lesson.
You’ll be rewarded for trying...
Thinking about Gumroad as a set of opinions that I have has been really helpful in terms of marketing
the business... saying, ‘We have this set of opinions around how to build a company or how to work’ –
is compelling to people. The crowd-funding, for example, happened in large part because people are
interested in Gumroad as a business and as an experiment that they want to support...
I also think that being public about the Gumroad’s story made it a company that people want to win.
It’s like watching a movie like Rocky: you want to root for the underdog... I’m sure there are at least a
few creators who leaned into that and used Gumroad purely for that reason."
Sahil:
2 One of the key players behind the movement on its origins and benefit
The Transparency Movement: Why It's Important, Buffer Blog
1 Sahil on how
No Meetings, No Deadlines, No Full-Time Employees, Sahil Lavingia
Recommended Reading:
3 Actionable guide to building in public
The Building in Public How-To Guide, Gaby Goldberg
There are two widely discussed considerations for not building in public:
o Increased competiton: businesses with little barrier to entry, those in competetive markets
should weigh the upside of BIP with the asymitry of information they'll create for their
competition
o Increased scrutiny: negetive signaling (several months of high churn, revenue dips, etc) can
damage customer, investor and your team's perception of the viability of the businss
Considerations:
The working culture at Gumroad is unique: there are no meetings, fixed working hours, or
deadlines. Designed for both efficiency and work/life balance, Sahil writes and tweets
about his hypotheses, experiments, and experiences building Gumroad's culture, which
in turn attracts a volume of candidates that have self select into the way they work,
enabling a unique working culture that would be difficult to build otherwise (eg. 30-50
interviews per engineer hire with a cost per interview of $0)
Attracting talent at no cost, and
eliminating meetings
BUILD IN PUBLIC (8/8)
“If you join Gumroad, my goal is that you learn almost nothing new on the day you join.
The revenue and everything you should have known, you could know right now by
Googling it, which I think is really important. I don’t want anyone to join the company
and realize this is not the right fit…
I make it really clear that I don’t like telling people what to do. I do that in the hiring
process, before the hiring process, on a jobs page, afterwards… So, hiring is definitely the
largest part of it – making sure you’re hiring the right kind of folks who can operate in
this way – and that’s mostly a function of being really clear with people and letting them
self-select out.
Ultimately, the hardest thing – and I think the reason a lot of people may want to work
this way but eventually won’t – is that it requires a really high bar of hiring. I interview
hundreds of people for some roles...”
Considerations:
There are three widely discussed arguments against building in
public:
o Increased competition: businesses with low barriers to entry, and
those in competitive markets should weigh the upside of BIP with the
downside of the asymitry of information they'll provide their competition
o Increased scrutiny: negative signaling (ex. several months of high
churn, revenue dips, etc) can damage customer, investor and your
team's perception of the viability of the businss
o Time better spend elsewhere: It takes time to create contnet. Your
time maybe spent better elewhere
2 History of some of the main players behind the BIP movement
The Transparency Movement: What It Is, Why It’s Important And How to Get Involved
1 Playbook on how to build in public by Gaby Goldberg
The Building in Public How-To Guide
Recommended Reading:
3 Cheat sheet that includes metrics that can be shared, places to post and people to follow
Build In Public Cheatsheet (v1.0)
“If you join Gumroad, my goal is that you learn almost nothing new on the day you join. The
revenue and everything you should have known, you could know right now by Googling it, which I
think is really important. I don’t want anyone to join the company and realize this is not the right
fit…
I make it really clear that I don’t like telling people what to do. I do that in the hiring process,
before the hiring process, on a jobs page, afterwards… So, hiring is definitely the largest part of it
– making sure you’re hiring the right kind of folks who can operate in this way – and that’s
mostly a function of being really clear with people and letting them self-select out.
Ultimately, the hardest thing – and I think the reason a lot of people may want to work this way
but eventually won’t – is that it requires a really high bar of hiring. I interview hundreds of people
for some roles...”
Sahil:
2 One of the key players behind the movement on its origins and benefit
The Transparency Movement: Why It's Important, Buffer Blog
1 Sahil on how
No Meetings, No Deadlines, No Full-Time Employees, Sahil Lavingia
Recommended Reading:
3 Actionable guide to building in public
The Building in Public How-To Guide, Gaby Goldberg
There are two widely discussed considerations for not building in public:
o Increased competiton: businesses with little barrier to entry, those in competetive markets
should weigh the upside of BIP with the asymitry of information they'll create for their
competition
o Increased scrutiny: negetive signaling (several months of high churn, revenue dips, etc) can
damage customer, investor and your team's perception of the viability of the businss
Considerations:
Startups "build in public" by:
o Proposing ideas (ex. product design) and getting feedback
o Shareing experiences/insights (ex. how you overcame roadblocks, what its like to work in the company)
for the purpose of:
o Galvanizing customers
o Increasing traffic/marketing
o Getting feedback
o Attracting talent
Sahil has also used this tactic to successfully raise funding, and improve the performance of his team
o The SEC recently increased the limit startups can raise through crowdfunding from $1M-$5M
o Sahil saw this as an opportunity to not only raise capital, but also "blur the lines between investor and customer"
creating super fans or spokes people for the company by raising from his audience
o 12 hours after going live on Republic.co, he raised $5M from 7,303 investors ($100-$1,000 cheque size)
o Nearly 2,300 were creators on Gumroad and many more were followers of his BIP journey
o As crowdfunding becomes more prevelant, an additonal benefit to BIP is leveraging your audience to finance the
business
1. Raising $5M in 12 hours
SUMMARY OF THE CASE STUDY
Lorem ipsum, Lorem ipsum, Lorem ipsum
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How Gumroad Overcame Early Growth Constraints

  • 1. Gumroad, with Sahil Lavingia From Silicon Vally hype to mass layoffs, and the tactics that helped Gumroad grow to their $100M valuation Tactician Case Interview: 001 http://www.Tactician.Tech
  • 2. This is a live document. Recommend resources, provide contrarian views, and additional insight by clicking where you see this: Subscribe for updates and future interviews here: SUBSCRIBE
  • 3. PRESERVERENCE What role preserverence played in Gumroad's journey to its $100M valuation BUILDING IN PUBLIC How BIP has helped Gumroad to attract the right talent, eliminate meetings, and raise $5m in 12 hours Topics Explored MARKET SIZING How size of market constrained Gumroad's early growth, and how founders can avoid building in small markets
  • 4. Sahil was born in the US, grew up in Singapore, then moved back to the US to study Computor Science at the University of Southern California. He dropped out to become Pinterest's second hire and built their iOS app, then left to start Gumroad in 2011 at the age of 19. He manages an investment fun with LPs that include Marc Andreeseen, Naval Ravikant, Elad Gil, and Tim Ferris, and has invested in Clubhouse, HelloSign, Notion, and Figma. Meet Sahil
  • 5. Meet Gumroad Gumroad helps content creators (ex. musicians, writers, filmmakers, photographers, etc.) sell digital products (ex. online courses, memberships, etc.) directly to their audiences. They monetize by charging a fee on each transaction and a $10 monthly fee to "Pro" account holders o Founded in 2011: Silicon Vally, USA o $16.1M raised o >40 employees o $100M valuation as of August, 2021
  • 7. Origin Story (1/6) o In high school, Sahil fell in love with building and selling digital products on the internet. o From a young age, he admired Bill Gates and aspired to build his own billion-dollar company.
  • 8. Origin Story (2/6) o He moved to the US for college, but dropped out at the age of 18 when he recieved an offer from Pinterest to build their iOS app and became their second employee.
  • 9. Origin Story (3/6) o Less than one year into his role at Pinterest, Sahil had designed an icon and wanted to sell it to his followeers on Twitter, but realized the process of selling was more difficult than it should be. o He built the first version of Gumroad over a weekend to solve that problem, and launched on Hacknews, landing at the #1 spot for the day. o With the hypothesis that over time more individuals and companies will want tools to sell directly to the audiences they build on social media and other platforms, he believed he was on to something.
  • 10. Origin Story (4/6) o He quit Pinterest shortly after (before vesting his equity), and raised a Seed round from Silicon Valley stalworths such as SV Angel, Max Levchin, Chris Sacca, and Josh Kopelman. o Before launching the product, the venture fund Kleiner Perkins offered Sahil a pre-emptive $7m Series A investment.
  • 11. Origin Story (5/6) o Gumroad made good headway in its first three years, however, the company did not grow fast enough to raise a Series B o After hundreds of unfruitful meetings with investors, Sahil eventually laid off his entire team of 20 and continued as a solo entreprenure, eventually moving to Utah to decompress and find direction
  • 12. Origin Story (6/6) o Gumroad is now a $100m company that employs 40 people
  • 13. Shahil plans to use the funding to xxxxxxxxx The future At $12 annualized revenue, Gumroad raised a $5m crowdfunded round within 12 hours 2021: $5M equity crowdfunding The first layoff took the company from 20 people down to 5. The second took the compnay from 5 to Shail as the only employee. He moved from Silicon Valley to Utah in 2017, looked for ways to process his experience, and continued working on Gumroad 2015: Layoffs begin Gumroad grew by close to 60% in 2016, 15% in 2017. In 2018 Sahil begain shipping features and hiring for the first time since the final layoffs and grew 25%, then 40% in 2019 and 87% in 2020 Continued growing the business Their 60-80% YoY growth wasn't the 3x growth Series B investors look for. Kleiner did a $2m bridge is 4x liquidation pereference 2014-2015: Struggled to raise Series B At 19 years old, raised a $1.1M seed round. Soon after raised a pre-emptive $7M Series A from Kleiner Perkins 2011: Raised Seed and Series A Timeline
  • 15. Top down is a less reliable way to estimate the size of a market alone, but using it with bottoms up analysis to triangulate, or sanity check your numbers can help you get a more accurate size of the market, and convince others. Investors at the earliest stages when there is less information, are more aminable to top down analysis. Aim to make the methodology used as clear as possible (ex. its common for investors to hear: "the market is $xB. If we get 10% of that, it could be $y!"... what are the assumptions that justify the ability to get 10%?) Considerations: 2 Important considerations when determining the market size for something fundamentally new Ways To Think ABout Market Size, by Benedict Evans 1 Step by step guide to determining the size of your market, in the context of pitching VC's Market Sizing: Framing the Opportunity, by Maximilian Bruhn Recommended Reading: 3 Why market size matters, when you should do analysis, and how to go about it Market Sizing Guide, by Pear VC Sahil: "...we had a few success cases where marquee folks – authors – made $300 000 in a year, which, as an author, is pretty crazy. We really felt we were going to be able to replicate this: If we had 1000 authors – that didn’t seem like too many – that’s $300 million a year. And then we realized, slowly, there were not that many of those authors... It doesn’t matter how awesome your product is, or how awesome your team is, or how often you ship features; the market you’re in is going to determine most of your growth... And often, you don’t really think about: How big is the market? How many people need this? How much money do they have, or are they willing to spend, on this sort of thing? So, I think it’s really important to spend time thinking a bit more about the market... Early adopters are often your best customers, and it is impossible to predict how many of them are out there until you start analyzing.... If we believe there are 50… or 5,000, lets make a list of all of them.” According to Sahil, the size of the creator market was the biggest limiter of Gumroad's early growth: there were fewer creators, and the LTV of each was smaller than expected. Ideniftying this earlier could have helped them to target a better segment, or pivot to a new market There are two ways startus can determine the size of their market to avoid suprises: 02 Bottoms up method Find the number of customers. Multiply that by the average revenue per customer per year MARKET SIZING 01 Top down method Broad industry market size (usually provided by a research company) multiplied by a target % of ownership. Less accurate as broad reseach rarely excludes segments that arn't targeted o According to Sahil, the size of the creator market was Gumroad's biggest limiter in its early growth: there were fewer creators, which meant fewer customers, and the LTV of each was smaller than expected o Identiftying this earlier could have helped them to target a better segment, or pivot to a new market MARKET SIZING (1/6)
  • 16. Top down is a less reliable way to estimate the size of a market alone, but using it with bottoms up analysis to triangulate, or sanity check your numbers can help you get a more accurate size of the market, and convince others. Investors at the earliest stages when there is less information, are more aminable to top down analysis. Aim to make the methodology used as clear as possible (ex. its common for investors to hear: "the market is $xB. If we get 10% of that, it could be $y!"... what are the assumptions that justify the ability to get 10%?) Considerations: 2 Important considerations when determining the market size for something fundamentally new Ways To Think ABout Market Size, by Benedict Evans 1 Step by step guide to determining the size of your market, in the context of pitching VC's Market Sizing: Framing the Opportunity, by Maximilian Bruhn Recommended Reading: 3 Why market size matters, when you should do analysis, and how to go about it Market Sizing Guide, by Pear VC Sahil: "...we had a few success cases where marquee folks – authors – made $300 000 in a year, which, as an author, is pretty crazy. We really felt we were going to be able to replicate this: If we had 1000 authors – that didn’t seem like too many – that’s $300 million a year. And then we realized, slowly, there were not that many of those authors... It doesn’t matter how awesome your product is, or how awesome your team is, or how often you ship features; the market you’re in is going to determine most of your growth... And often, you don’t really think about: How big is the market? How many people need this? How much money do they have, or are they willing to spend, on this sort of thing? So, I think it’s really important to spend time thinking a bit more about the market... Early adopters are often your best customers, and it is impossible to predict how many of them are out there until you start analyzing.... If we believe there are 50… or 5,000, lets make a list of all of them.” According to Sahil, the size of the creator market was the biggest limiter of Gumroad's early growth: there were fewer creators, and the LTV of each was smaller than expected. Ideniftying this earlier could have helped them to target a better segment, or pivot to a new market There are two ways startus can determine the size of their market to avoid suprises: 02 Bottoms up method Find the number of customers. Multiply that by the average revenue per customer per year MARKET SIZING 01 Top down method Broad industry market size (usually provided by a research company) multiplied by a target % of ownership. Less accurate as broad reseach rarely excludes segments that arn't targeted Going after an attractive market is considered by many to be the most important thing you can do (even more important than the quality of your team, or your product). As Marc Andreessen (Andreessen Horowitz, Co-Founder) puts it: "… in a terrible market, you can have the best product in the world and an absolutely killer team, and it doesn’t matter—you’re going to fail... You’ll break your pick for years trying to find customers who don’t exist for your marvelous product, and your wonderful team will eventually get demoralized and quit, and your startup will die. … assuming the team is baseline competent and the product is fundamentally acceptable, a great market will tend to equal success and a poor market will tend to equal failure." MARKET SIZING (2/6)
  • 17. Top down is a less reliable way to estimate the size of a market alone, but using it with bottoms up analysis to triangulate, or sanity check your numbers can help you get a more accurate size of the market, and convince others. Investors at the earliest stages when there is less information, are more aminable to top down analysis. Aim to make the methodology used as clear as possible (ex. its common for investors to hear: "the market is $xB. If we get 10% of that, it could be $y!"... what are the assumptions that justify the ability to get 10%?) Considerations: 2 Important considerations when determining the market size for something fundamentally new Ways To Think ABout Market Size, by Benedict Evans 1 Step by step guide to determining the size of your market, in the context of pitching VC's Market Sizing: Framing the Opportunity, by Maximilian Bruhn Recommended Reading: 3 Why market size matters, when you should do analysis, and how to go about it Market Sizing Guide, by Pear VC Sahil: "...we had a few success cases where marquee folks – authors – made $300 000 in a year, which, as an author, is pretty crazy. We really felt we were going to be able to replicate this: If we had 1000 authors – that didn’t seem like too many – that’s $300 million a year. And then we realized, slowly, there were not that many of those authors... It doesn’t matter how awesome your product is, or how awesome your team is, or how often you ship features; the market you’re in is going to determine most of your growth... And often, you don’t really think about: How big is the market? How many people need this? How much money do they have, or are they willing to spend, on this sort of thing? So, I think it’s really important to spend time thinking a bit more about the market... Early adopters are often your best customers, and it is impossible to predict how many of them are out there until you start analyzing.... If we believe there are 50… or 5,000, lets make a list of all of them.” According to Sahil, the size of the creator market was the biggest limiter of Gumroad's early growth: there were fewer creators, and the LTV of each was smaller than expected. Ideniftying this earlier could have helped them to target a better segment, or pivot to a new market There are two ways startus can determine the size of their market to avoid suprises: 02 Bottoms up method Find the number of customers. Multiply that by the average revenue per customer per year MARKET SIZING 01 Top down method Broad industry market size (usually provided by a research company) multiplied by a target % of ownership. Less accurate as broad reseach rarely excludes segments that arn't targeted A market's attractiness is dictated by its size and growth rate, competition and customer dynamics. Low switching cost, low barriers to entry, cheap customers are all bad for business However, innovation (in product, channel, etc.) can create new markets, increase switching cost and render competition moot. The greater your intention, available capital, and team's competency for innovation, the less important to focus on competitive forces in evaluating a market. MARKET SIZING (3/6)
  • 18. Top down is a less reliable way to estimate the size of a market alone, but using it with bottoms up analysis to triangulate, or sanity check your numbers can help you get a more accurate size of the market, and convince others. Investors at the earliest stages when there is less information, are more aminable to top down analysis. Aim to make the methodology used as clear as possible (ex. its common for investors to hear: "the market is $xB. If we get 10% of that, it could be $y!"... what are the assumptions that justify the ability to get 10%?) Considerations: 2 Important considerations when determining the market size for something fundamentally new Ways To Think ABout Market Size, by Benedict Evans 1 Step by step guide to determining the size of your market, in the context of pitching VC's Market Sizing: Framing the Opportunity, by Maximilian Bruhn Recommended Reading: 3 Why market size matters, when you should do analysis, and how to go about it Market Sizing Guide, by Pear VC Sahil: "...we had a few success cases where marquee folks – authors – made $300 000 in a year, which, as an author, is pretty crazy. We really felt we were going to be able to replicate this: If we had 1000 authors – that didn’t seem like too many – that’s $300 million a year. And then we realized, slowly, there were not that many of those authors... It doesn’t matter how awesome your product is, or how awesome your team is, or how often you ship features; the market you’re in is going to determine most of your growth... And often, you don’t really think about: How big is the market? How many people need this? How much money do they have, or are they willing to spend, on this sort of thing? So, I think it’s really important to spend time thinking a bit more about the market... Early adopters are often your best customers, and it is impossible to predict how many of them are out there until you start analyzing.... If we believe there are 50… or 5,000, lets make a list of all of them.” According to Sahil, the size of the creator market was the biggest limiter of Gumroad's early growth: there were fewer creators, and the LTV of each was smaller than expected. Ideniftying this earlier could have helped them to target a better segment, or pivot to a new market There are two ways startus can determine the size of their market to avoid suprises: 02 Bottoms up method Find the number of customers. Multiply that by the average revenue per customer per year MARKET SIZING 01 Top down method Broad industry market size (usually provided by a research company) multiplied by a target % of ownership. Less accurate as broad reseach rarely excludes segments that arn't targeted o There are two ways startups can determine the size of their market to avoid suprises: MARKET SIZING (4/6)
  • 19. Top down is a less reliable way to estimate the size of a market alone, but using it with bottoms up analysis to triangulate, or sanity check your numbers can help you get a more accurate size of the market, and convince others. Investors at the earliest stages when there is less information, are more aminable to top down analysis. Aim to make the methodology used as clear as possible (ex. its common for investors to hear: "the market is $xB. If we get 10% of that, it could be $y!"... what are the assumptions that justify the ability to get 10%?) Considerations: 2 Important considerations when determining the market size for something fundamentally new Ways To Think ABout Market Size, by Benedict Evans 1 Step by step guide to determining the size of your market, in the context of pitching VC's Market Sizing: Framing the Opportunity, by Maximilian Bruhn Recommended Reading: 3 Why market size matters, when you should do analysis, and how to go about it Market Sizing Guide, by Pear VC Sahil: "...we had a few success cases where marquee folks – authors – made $300 000 in a year, which, as an author, is pretty crazy. We really felt we were going to be able to replicate this: If we had 1000 authors – that didn’t seem like too many – that’s $300 million a year. And then we realized, slowly, there were not that many of those authors... It doesn’t matter how awesome your product is, or how awesome your team is, or how often you ship features; the market you’re in is going to determine most of your growth... And often, you don’t really think about: How big is the market? How many people need this? How much money do they have, or are they willing to spend, on this sort of thing? So, I think it’s really important to spend time thinking a bit more about the market... Early adopters are often your best customers, and it is impossible to predict how many of them are out there until you start analyzing.... If we believe there are 50… or 5,000, lets make a list of all of them.” According to Sahil, the size of the creator market was the biggest limiter of Gumroad's early growth: there were fewer creators, and the LTV of each was smaller than expected. Ideniftying this earlier could have helped them to target a better segment, or pivot to a new market There are two ways startus can determine the size of their market to avoid suprises: 02 Bottoms up method Find the number of customers. Multiply that by the average revenue per customer per year MARKET SIZING 01 Top down method Broad industry market size (usually provided by a research company) multiplied by a target % of ownership. Less accurate as broad reseach rarely excludes segments that arn't targeted MARKET SIZING (5/6) 01 Top down method: The number of customers that exist (usually found in broad industry research) multiplied by what you expect to earn off each customer. For example, imagine your company sells learning resources to schools. Your research shows 10,000 relevant schools in your country, and your average sale per school is $10k, which means your market size is $100M. Although top down is simple, it is often unreliable and overly optimistic. Not EVERY school needs your product, and perhaps not all would take your $10k package.
  • 20. Top down is a less reliable way to estimate the size of a market alone, but using it with bottoms up analysis to triangulate, or sanity check your numbers can help you get a more accurate size of the market, and convince others. Investors at the earliest stages when there is less information, are more aminable to top down analysis. Aim to make the methodology used as clear as possible (ex. its common for investors to hear: "the market is $xB. If we get 10% of that, it could be $y!"... what are the assumptions that justify the ability to get 10%?) Considerations: 2 Important considerations when determining the market size for something fundamentally new Ways To Think ABout Market Size, by Benedict Evans 1 Step by step guide to determining the size of your market, in the context of pitching VC's Market Sizing: Framing the Opportunity, by Maximilian Bruhn Recommended Reading: 3 Why market size matters, when you should do analysis, and how to go about it Market Sizing Guide, by Pear VC Sahil: "...we had a few success cases where marquee folks – authors – made $300 000 in a year, which, as an author, is pretty crazy. We really felt we were going to be able to replicate this: If we had 1000 authors – that didn’t seem like too many – that’s $300 million a year. And then we realized, slowly, there were not that many of those authors... It doesn’t matter how awesome your product is, or how awesome your team is, or how often you ship features; the market you’re in is going to determine most of your growth... And often, you don’t really think about: How big is the market? How many people need this? How much money do they have, or are they willing to spend, on this sort of thing? So, I think it’s really important to spend time thinking a bit more about the market... Early adopters are often your best customers, and it is impossible to predict how many of them are out there until you start analyzing.... If we believe there are 50… or 5,000, lets make a list of all of them.” According to Sahil, the size of the creator market was the biggest limiter of Gumroad's early growth: there were fewer creators, and the LTV of each was smaller than expected. Ideniftying this earlier could have helped them to target a better segment, or pivot to a new market There are two ways startus can determine the size of their market to avoid suprises: 02 Bottoms up method Find the number of customers. Multiply that by the average revenue per customer per year MARKET SIZING 01 Top down method Broad industry market size (usually provided by a research company) multiplied by a target % of ownership. Less accurate as broad reseach rarely excludes segments that arn't targeted MARKET SIZING (6/6) 02 Bottoms up method Identify the specific segments you will target, source a list of potential customers, multiply by the expected revenue per customer. The distiction here is that you've made a specific list of customers. Not only can bottoms up be more accurate than top down, it can also help identify and list customers to target Generally, earlier stage investors are amenable to top down. By Series A aim to be able to do bottoms up
  • 21. "...we had a few success cases where marquee folks – authors – made $300,000 in a year, which as an author, is pretty crazy. We really felt we were going to be able to replicate this: If we had 1000 authors – that didn’t seem like too many – that’s $300 million a year. And then we realized, slowly, there were not that many of those authors... It doesn’t matter how awesome your product is, or how awesome your team is, or how often you ship features; the market you’re in is going to determine most of your growth... And often, you don’t really think about: How big is the market? How many people need this? How much money do they have, or are they willing to spend, on this sort of thing? So, I think it’s really important to spend time thinking a bit more about the market... Early adopters are often your best customers, and it is impossible to predict how many of them are out there until you start analyzing.... If we believe there are 50… or 5,000, lets make a list of all of them.”
  • 22. "...we had a few success cases where marquee folks – authors – made $300,000 in a year, which as an author, is pretty crazy. We really felt we were going to be able to replicate this: If we had 1000 authors – that didn’t seem like too many – that’s $300 million a year. And then we realized, slowly, there were not that many of those authors... It doesn’t matter how awesome your product is, or how awesome your team is, or how often you ship features; the market you’re in is going to determine most of your growth... And often, you don’t really think about: How big is the market? How many people need this? How much money do they have, or are they willing to spend, on this sort of thing? So, I think it’s really important to spend time thinking a bit more about the market... Early adopters are often your best customers, and it is impossible to predict how many of them are out there until you start analyzing.... If we believe there are 50… or 5,000, lets make a list of all of them.”
  • 23. "Placehodler for comment from Elizabeth. Lorem ipsum delor.” Elizabeth Yin GP @Hustle fund
  • 24. 2 Important considerations when determining the market size for something fundamentally new Ways To Think ABout Market Size, by Benedict Evans 1 Step by step guide to determining the size of your market, in the context of pitching VC's Market Sizing: Framing the Opportunity, by Maximilian Bruhn Recommended Reading: 3 Why market size matters, when you should do analysis, and how to go about it Market Sizing Guide, by Pear VC The Only Thing That Matters, by Marc Andreeseen Why the market is more important then team and product for startups 4
  • 25. Key Challange: Surviving the "Trough of Sorrow" http://www.Tactician.Tech
  • 26. “If you join Gumroad, my goal is that you learn almost nothing new on the day you join. The revenue and everything you should have known, you could know right now by Googling it, which I think is really important. I don’t want anyone to join the company and realize this is not the right fit… I make it really clear that I don’t like telling people what to do. I do that in the hiring process, before the hiring process, on a jobs page, afterwards… So, hiring is definitely the largest part of it – making sure you’re hiring the right kind of folks who can operate in this way – and that’s mostly a function of being really clear with people and letting them self-select out. Ultimately, the hardest thing – and I think the reason a lot of people may want to work this way but eventually won’t – is that it requires a really high bar of hiring. I interview hundreds of people for some roles...” Sahil: 2 Reddal provides a case study on one company's approch to getting out of the TOS and gives advice on how to think about pivoting Tech startups can minimize their time in the trough of sorrow with a zoom-in pivot 1 Andrew Chen provides both emotional and tactical advice on how to manage, and exit the TOS After the Techcrunch bump: Life in the “Trough of Sorrow” Recommended Reading: 3 Brain Balfour shares the most important characteristic of his company that got his startup out of the TOS How We Got Through The Trough Of Sorrow There are two widely discussed considerations for not building in public: o Increased competiton: businesses with little barrier to entry, those in competetive markets should weigh the upside of BIP with the asymitry of information they'll create for their competition o Increased scrutiny: negetive signaling (several months of high churn, revenue dips, etc) can damage customer, investor and your team's perception of the viability of the businss Considerations: There are four essential "fits" a startup needs to reach in order to scale: Product/Market Fit → Does your product satisfy demand? Product/Channel Fit → Products are built to fit marketing/growth channels. Can you product leverage a particular channel to scale? Channel/Model Fit → how you charge (freemium, transactional, free trial, one year upfront, etc.) and how much you earn from customers dictates what channels can provide profitable growth. Does your business model fit said channel? Model/Market Fit → There need to be enough customers at your average revenue per customer to create a big business SURVIVING THE TROUGH OF SORROW (1/6) In competing for talent, Gumroad’s competitive advantages are flexibility and efficiency. Gumroad's team doesn't hold meetings, eliminating time wasted on coordination o Tweeting and writing about his experience and experiments building this unique culture attracts applicants (50-30 interviews per engineer hire) o Those applicants have self selected into Guhmroad’s unique work environment and plan: candidates are aligned to the work culture, state of the business’ financials, mission and vision before they start work, creating a highly engaged and motivated team 1. Creating an efficient work culture
  • 27. “If you join Gumroad, my goal is that you learn almost nothing new on the day you join. The revenue and everything you should have known, you could know right now by Googling it, which I think is really important. I don’t want anyone to join the company and realize this is not the right fit… I make it really clear that I don’t like telling people what to do. I do that in the hiring process, before the hiring process, on a jobs page, afterwards… So, hiring is definitely the largest part of it – making sure you’re hiring the right kind of folks who can operate in this way – and that’s mostly a function of being really clear with people and letting them self-select out. Ultimately, the hardest thing – and I think the reason a lot of people may want to work this way but eventually won’t – is that it requires a really high bar of hiring. I interview hundreds of people for some roles...” Sahil: 2 Reddal provides a case study on one company's approch to getting out of the TOS and gives advice on how to think about pivoting Tech startups can minimize their time in the trough of sorrow with a zoom-in pivot 1 Andrew Chen provides both emotional and tactical advice on how to manage, and exit the TOS After the Techcrunch bump: Life in the “Trough of Sorrow” Recommended Reading: 3 Brain Balfour shares the most important characteristic of his company that got his startup out of the TOS How We Got Through The Trough Of Sorrow There are two widely discussed considerations for not building in public: o Increased competiton: businesses with little barrier to entry, those in competetive markets should weigh the upside of BIP with the asymitry of information they'll create for their competition o Increased scrutiny: negetive signaling (several months of high churn, revenue dips, etc) can damage customer, investor and your team's perception of the viability of the businss Considerations: - The challenge Sahil faced was model/market fit: that there didn't seemed to be enough customers for the business model to create a large, fast growing company - That situation of post-launch slow growth is often referred to as the Trough of Sorrow. Sahil spent (arguably) 8 years there and in "Wiggles of False Hope" -What got him out was perseverance - ie. not allowing the company to die so that he could: SURVIVING THE TROUGH OF SORROW (2/6) In competing for talent, Gumroad’s competitive advantages are flexibility and efficiency. Gumroad's team doesn't hold meetings, eliminating time wasted on coordination o Tweeting and writing about his experience and experiments building this unique culture attracts applicants (50-30 interviews per engineer hire) o Those applicants have self selected into Guhmroad’s unique work environment and plan: candidates are aligned to the work culture, state of the business’ financials, mission and vision before they start work, creating a highly engaged and motivated team 1. Creating an efficient work culture Coined by Paul Graham, Co-Founder of Y Combinator
  • 28. “If you join Gumroad, my goal is that you learn almost nothing new on the day you join. The revenue and everything you should have known, you could know right now by Googling it, which I think is really important. I don’t want anyone to join the company and realize this is not the right fit… I make it really clear that I don’t like telling people what to do. I do that in the hiring process, before the hiring process, on a jobs page, afterwards… So, hiring is definitely the largest part of it – making sure you’re hiring the right kind of folks who can operate in this way – and that’s mostly a function of being really clear with people and letting them self-select out. Ultimately, the hardest thing – and I think the reason a lot of people may want to work this way but eventually won’t – is that it requires a really high bar of hiring. I interview hundreds of people for some roles...” Sahil: 2 Reddal provides a case study on one company's approch to getting out of the TOS and gives advice on how to think about pivoting Tech startups can minimize their time in the trough of sorrow with a zoom-in pivot 1 Andrew Chen provides both emotional and tactical advice on how to manage, and exit the TOS After the Techcrunch bump: Life in the “Trough of Sorrow” Recommended Reading: 3 Brain Balfour shares the most important characteristic of his company that got his startup out of the TOS How We Got Through The Trough Of Sorrow There are two widely discussed considerations for not building in public: o Increased competiton: businesses with little barrier to entry, those in competetive markets should weigh the upside of BIP with the asymitry of information they'll create for their competition o Increased scrutiny: negetive signaling (several months of high churn, revenue dips, etc) can damage customer, investor and your team's perception of the viability of the businss Considerations: o Learn and iterate: time, and diligent studing of customers has lead the team to re-segment and target higher value customers with product offering he believes has lower competition, and launch a membership product which fules most of the current revenue growth. SURVIVING THE TROUGH OF SORROW (3/6) In competing for talent, Gumroad’s competitive advantages are flexibility and efficiency. Gumroad's team doesn't hold meetings, eliminating time wasted on coordination o Tweeting and writing about his experience and experiments building this unique culture attracts applicants (50-30 interviews per engineer hire) o Those applicants have self selected into Guhmroad’s unique work environment and plan: candidates are aligned to the work culture, state of the business’ financials, mission and vision before they start work, creating a highly engaged and motivated team 1. Creating an efficient work culture
  • 29. “If you join Gumroad, my goal is that you learn almost nothing new on the day you join. The revenue and everything you should have known, you could know right now by Googling it, which I think is really important. I don’t want anyone to join the company and realize this is not the right fit… I make it really clear that I don’t like telling people what to do. I do that in the hiring process, before the hiring process, on a jobs page, afterwards… So, hiring is definitely the largest part of it – making sure you’re hiring the right kind of folks who can operate in this way – and that’s mostly a function of being really clear with people and letting them self-select out. Ultimately, the hardest thing – and I think the reason a lot of people may want to work this way but eventually won’t – is that it requires a really high bar of hiring. I interview hundreds of people for some roles...” Sahil: 2 Reddal provides a case study on one company's approch to getting out of the TOS and gives advice on how to think about pivoting Tech startups can minimize their time in the trough of sorrow with a zoom-in pivot 1 Andrew Chen provides both emotional and tactical advice on how to manage, and exit the TOS After the Techcrunch bump: Life in the “Trough of Sorrow” Recommended Reading: 3 Brain Balfour shares the most important characteristic of his company that got his startup out of the TOS How We Got Through The Trough Of Sorrow There are two widely discussed considerations for not building in public: o Increased competiton: businesses with little barrier to entry, those in competetive markets should weigh the upside of BIP with the asymitry of information they'll create for their competition o Increased scrutiny: negetive signaling (several months of high churn, revenue dips, etc) can damage customer, investor and your team's perception of the viability of the businss Considerations: 2. Take advantage of unpredictable favorable events: He rode the small but steady growth of the creator market over a perioed of 10 years and managed to bing in perfect position to capitalize on the spike in 2020 that resulted from COVID-19. SURVIVING THE TROUGH OF SORROW (4/6) In competing for talent, Gumroad’s competitive advantages are flexibility and efficiency. Gumroad's team doesn't hold meetings, eliminating time wasted on coordination o Tweeting and writing about his experience and experiments building this unique culture attracts applicants (50-30 interviews per engineer hire) o Those applicants have self selected into Guhmroad’s unique work environment and plan: candidates are aligned to the work culture, state of the business’ financials, mission and vision before they start work, creating a highly engaged and motivated team 1. Creating an efficient work culture
  • 30. “If you join Gumroad, my goal is that you learn almost nothing new on the day you join. The revenue and everything you should have known, you could know right now by Googling it, which I think is really important. I don’t want anyone to join the company and realize this is not the right fit… I make it really clear that I don’t like telling people what to do. I do that in the hiring process, before the hiring process, on a jobs page, afterwards… So, hiring is definitely the largest part of it – making sure you’re hiring the right kind of folks who can operate in this way – and that’s mostly a function of being really clear with people and letting them self-select out. Ultimately, the hardest thing – and I think the reason a lot of people may want to work this way but eventually won’t – is that it requires a really high bar of hiring. I interview hundreds of people for some roles...” Sahil: 2 Reddal provides a case study on one company's approch to getting out of the TOS and gives advice on how to think about pivoting Tech startups can minimize their time in the trough of sorrow with a zoom-in pivot 1 Andrew Chen provides both emotional and tactical advice on how to manage, and exit the TOS After the Techcrunch bump: Life in the “Trough of Sorrow” Recommended Reading: 3 Brain Balfour shares the most important characteristic of his company that got his startup out of the TOS How We Got Through The Trough Of Sorrow There are two widely discussed considerations for not building in public: o Increased competiton: businesses with little barrier to entry, those in competetive markets should weigh the upside of BIP with the asymitry of information they'll create for their competition o Increased scrutiny: negetive signaling (several months of high churn, revenue dips, etc) can damage customer, investor and your team's perception of the viability of the businss Considerations: Here are his recommendations for what to do if you find yourself there: SURVIVING THE TROUGH OF SORROW (5/6) In competing for talent, Gumroad’s competitive advantages are flexibility and efficiency. Gumroad's team doesn't hold meetings, eliminating time wasted on coordination o Tweeting and writing about his experience and experiments building this unique culture attracts applicants (50-30 interviews per engineer hire) o Those applicants have self selected into Guhmroad’s unique work environment and plan: candidates are aligned to the work culture, state of the business’ financials, mission and vision before they start work, creating a highly engaged and motivated team 1. Creating an efficient work culture
  • 31. “If you join Gumroad, my goal is that you learn almost nothing new on the day you join. The revenue and everything you should have known, you could know right now by Googling it, which I think is really important. I don’t want anyone to join the company and realize this is not the right fit… I make it really clear that I don’t like telling people what to do. I do that in the hiring process, before the hiring process, on a jobs page, afterwards… So, hiring is definitely the largest part of it – making sure you’re hiring the right kind of folks who can operate in this way – and that’s mostly a function of being really clear with people and letting them self-select out. Ultimately, the hardest thing – and I think the reason a lot of people may want to work this way but eventually won’t – is that it requires a really high bar of hiring. I interview hundreds of people for some roles...” Sahil: 2 Reddal provides a case study on one company's approch to getting out of the TOS and gives advice on how to think about pivoting Tech startups can minimize their time in the trough of sorrow with a zoom-in pivot 1 Andrew Chen provides both emotional and tactical advice on how to manage, and exit the TOS After the Techcrunch bump: Life in the “Trough of Sorrow” Recommended Reading: 3 Brain Balfour shares the most important characteristic of his company that got his startup out of the TOS How We Got Through The Trough Of Sorrow There are two widely discussed considerations for not building in public: o Increased competiton: businesses with little barrier to entry, those in competetive markets should weigh the upside of BIP with the asymitry of information they'll create for their competition o Increased scrutiny: negetive signaling (several months of high churn, revenue dips, etc) can damage customer, investor and your team's perception of the viability of the businss Considerations: o Get clear on what needs to be: (a) proven, (b) accomplished, (c) by when - to get to the next stage (i.e. profitability or next funding round), and be sure to give yourself as much runway as possible. o Consider setting a "red alert" – deadline, by which to start exploring pivots if you are still not getting appropriate traction. o Test and prove your hypothesis of the value delivered by your product through customer targeting, customer acquisition and retention until you find the path out... or pivot. SURVIVING THE TROUGH OF SORROW (6/6) In competing for talent, Gumroad’s competitive advantages are flexibility and efficiency. Gumroad's team doesn't hold meetings, eliminating time wasted on coordination o Tweeting and writing about his experience and experiments building this unique culture attracts applicants (50-30 interviews per engineer hire) o Those applicants have self selected into Guhmroad’s unique work environment and plan: candidates are aligned to the work culture, state of the business’ financials, mission and vision before they start work, creating a highly engaged and motivated team 1. Creating an efficient work culture
  • 32. "One thing I definitely think we should have done was to say: We’re always going to have more than 18 months of runway, which means that if we get to two years we need to stop hiring people. It’ like red alert. We had a lot of optimism in the market – and maybe in 2020 that was proven out – and we felt it was going to take a lot of time for these verticals to develop; that we just had to exist long enough... Because of the lack of red alert, we didn’t have the capacity to really do anything. We had a couple of experiments; we had a bunch of things we tried in the last nine-month sprint. We shipped a bunch of features, but we just didn’t have the capacity, the team or the energy at that time to build a totally new product from scratch."
  • 33. 2 Reddal provides a case study on one company's approch to getting out of the TOS and gives advice on how to think about pivoting Tech startups can minimize their time in the trough of sorrow with a zoom-in pivot 1 Andrew Chen provides both emotional and tactical advice on how to manage, and exit the TOS After the Techcrunch bump: Life in the “Trough of Sorrow” Recommended Reading: 3 Brain Balfour shares the most important characteristic of his company that got his startup out of the TOS How We Got Through The Trough Of Sorrow 4 Brain Balfour shares the most important characteristic of his company that got his startup out of the TOS How We Got Through The Trough Of Sorrow
  • 34. Key Opportunity: Build in Public http://www.Tactician.Tech
  • 35. Startups "build in public" (BIP) by sharing aspects of their journey (obstacles, tips, metrics, learnings, resources, process, etc.) publicly. BUILD IN PUBLIC (1/8)
  • 36. BUILD IN PUBLIC (2/8) An emerging trend that has exploded in popularity since 2018, there are three audiences: o Customers: people interested in your product o Observers: people interested in your process (fellow entrepreneurs, media, potential hires, potential investors) o Yourself: keep yourself accountable
  • 37. Examples: BUILD IN PUBLIC (3/8) Product Hunt gathers feedback on design from Twitter followers Buffer makes revenue, staff salaries, etc. public Third example, Third example, Third example, Third example Fourth example, Fourth example, Fourth example, Forthe example
  • 38. BUILD IN PUBLIC (4/8) Why BIP? o To build an audience o Market to/monetize an audience o Increase engagement, buy-in, trust o To keep yourself accountable o To validate ideas/get feedback o To share knowledge/ help others o To build a network/support group What to share: o Teach what you've learned o Share stats o Celebrate milestones o Share failures o Outline plans o Ask questions / seek feedback Where to share: o Social media o Blog o BIP platforms/communities How to do it? o Syncronously: build in isolation and tell the world about it when you are ready o Asyncronously: speak to your audience while building
  • 39. Top down is a less reliable way to estimate the size of a market alone, but using it with bottoms up analysis to triangulate, or sanity check your numbers can help you get a more accurate size of the market, and convince others. Investors at the earliest stages when there is less information, are more aminable to top down analysis. Aim to make the methodology used as clear as possible (ex. its common for investors to hear: "the market is $xB. If we get 10% of that, it could be $y!"... what are the assumptions that justify the ability to get 10%?) Considerations: 2 Important considerations when determining the market size for something fundamentally new Ways To Think ABout Market Size, by Benedict Evans 1 Step by step guide to determining the size of your market, in the context of pitching VC's Market Sizing: Framing the Opportunity, by Maximilian Bruhn Recommended Reading: 3 Why market size matters, when you should do analysis, and how to go about it Market Sizing Guide, by Pear VC Sahil: "...we had a few success cases where marquee folks – authors – made $300 000 in a year, which, as an author, is pretty crazy. We really felt we were going to be able to replicate this: If we had 1000 authors – that didn’t seem like too many – that’s $300 million a year. And then we realized, slowly, there were not that many of those authors... It doesn’t matter how awesome your product is, or how awesome your team is, or how often you ship features; the market you’re in is going to determine most of your growth... And often, you don’t really think about: How big is the market? How many people need this? How much money do they have, or are they willing to spend, on this sort of thing? So, I think it’s really important to spend time thinking a bit more about the market... Early adopters are often your best customers, and it is impossible to predict how many of them are out there until you start analyzing.... If we believe there are 50… or 5,000, lets make a list of all of them.” According to Sahil, the size of the creator market was the biggest limiter of Gumroad's early growth: there were fewer creators, and the LTV of each was smaller than expected. Ideniftying this earlier could have helped them to target a better segment, or pivot to a new market There are two ways startus can determine the size of their market to avoid suprises: 02 Bottoms up method Find the number of customers. Multiply that by the average revenue per customer per year MARKET SIZING 01 Top down method Broad industry market size (usually provided by a research company) multiplied by a target % of ownership. Less accurate as broad reseach rarely excludes segments that arn't targeted Sahil has leveraged BIP to raise funding, and improve the performance of his team: BUILD IN PUBLIC (5/8)
  • 40. "The benefit of building in public is that you have an audience, so when you launch your product, you’ve already seeded the idea in everyone’s head and everyone’s ready for it, which is important. The downside is that it’s embarrassing – it’s public embarrassment. The trick is realizing that no-one cares about your failure; everyone’s just impressed that you tried – and that’s another important lesson. You’ll be rewarded for trying... Thinking about Gumroad as a set of opinions that I have has been really helpful in terms of marketing the business... saying, ‘We have this set of opinions around how to build a company or how to work’ – is compelling to people. The crowd-funding, for example, happened in large part because people are interested in Gumroad as a business and as an experiment that they want to support... I also think that being public about the Gumroad’s story made it a company that people want to win. It’s like watching a movie like Rocky: you want to root for the underdog... I’m sure there are at least a few creators who leaned into that and used Gumroad purely for that reason." Sahil: 2 One of the key players behind the movement on its origins and benefit The Transparency Movement: Why It's Important, Buffer Blog 1 Sahil on how No Meetings, No Deadlines, No Full-Time Employees, Sahil Lavingia Recommended Reading: 3 Actionable guide to building in public The Building in Public How-To Guide, Gaby Goldberg There are two widely discussed considerations for not building in public: o Increased competiton: businesses with little barrier to entry, those in competetive markets should weigh the upside of BIP with the asymitry of information they'll create for their competition o Increased scrutiny: negetive signaling (several months of high churn, revenue dips, etc) can damage customer, investor and your team's perception of the viability of the businss Considerations: o In March, 2021, the SEC increased the limit startups can raise through crowdfunding from $1M to $5M o Sahil saw this as an opportunity to not only raise capital, but also "blur the lines between investor and customer" by creating super fans or spokespeople for the company by raising funding from his audience Raising $5M in 12 hours BUILD IN PUBLIC (6/8)
  • 41. "The benefit of building in public is that you have an audience, so when you launch your product, you’ve already seeded the idea in everyone’s head and everyone’s ready for it, which is important. The downside is that it’s embarrassing – it’s public embarrassment. The trick is realizing that no-one cares about your failure; everyone’s just impressed that you tried – and that’s another important lesson. You’ll be rewarded for trying... Thinking about Gumroad as a set of opinions that I have has been really helpful in terms of marketing the business... saying, ‘We have this set of opinions around how to build a company or how to work’ – is compelling to people. The crowd-funding, for example, happened in large part because people are interested in Gumroad as a business and as an experiment that they want to support... I also think that being public about the Gumroad’s story made it a company that people want to win. It’s like watching a movie like Rocky: you want to root for the underdog... I’m sure there are at least a few creators who leaned into that and used Gumroad purely for that reason." Sahil: 2 One of the key players behind the movement on its origins and benefit The Transparency Movement: Why It's Important, Buffer Blog 1 Sahil on how No Meetings, No Deadlines, No Full-Time Employees, Sahil Lavingia Recommended Reading: 3 Actionable guide to building in public The Building in Public How-To Guide, Gaby Goldberg There are two widely discussed considerations for not building in public: o Increased competiton: businesses with little barrier to entry, those in competetive markets should weigh the upside of BIP with the asymitry of information they'll create for their competition o Increased scrutiny: negetive signaling (several months of high churn, revenue dips, etc) can damage customer, investor and your team's perception of the viability of the businss Considerations: o 12 hours after going live on Republic.co, he raised $5M from 7,303 investors (in $100 to $1,000 cheque sizes) o Nearly 2,300 were customers of Gumroad and a large portion of the rest were followers of his BIP journey o As crowdfunding becomes more prevelant, an additonal benefit to BIP is leveraging your audience to finance your business Raising $5M in 12 hours BUILD IN PUBLIC (7/8)
  • 42. "The benefit of building in public is that you have an audience, so when you launch your product, you’ve already seeded the idea in everyone’s head and everyone’s ready for it, which is important. The downside is that it’s embarrassing – it’s public embarrassment. The trick is realizing that no-one cares about your failure; everyone’s just impressed that you tried – and that’s another important lesson. You’ll be rewarded for trying... Thinking about Gumroad as a set of opinions that I have has been really helpful in terms of marketing the business... saying, ‘We have this set of opinions around how to build a company or how to work’ – is compelling to people. The crowd-funding, for example, happened in large part because people are interested in Gumroad as a business and as an experiment that they want to support... I also think that being public about the Gumroad’s story made it a company that people want to win. It’s like watching a movie like Rocky: you want to root for the underdog... I’m sure there are at least a few creators who leaned into that and used Gumroad purely for that reason."
  • 43. "The benefit of building in public is that you have an audience, so when you launch your product, you’ve already seeded the idea in everyone’s head and everyone’s ready for it, which is important. The downside is that it’s embarrassing – it’s public embarrassment. The trick is realizing that no-one cares about your failure; everyone’s just impressed that you tried – and that’s another important lesson. You’ll be rewarded for trying... Thinking about Gumroad as a set of opinions that I have has been really helpful in terms of marketing the business... saying, ‘We have this set of opinions around how to build a company or how to work’ – is compelling to people. The crowd-funding, for example, happened in large part because people are interested in Gumroad as a business and as an experiment that they want to support... I also think that being public about the Gumroad’s story made it a company that people want to win. It’s like watching a movie like Rocky: you want to root for the underdog... I’m sure there are at least a few creators who leaned into that and used Gumroad purely for that reason." Sahil: 2 One of the key players behind the movement on its origins and benefit The Transparency Movement: Why It's Important, Buffer Blog 1 Sahil on how No Meetings, No Deadlines, No Full-Time Employees, Sahil Lavingia Recommended Reading: 3 Actionable guide to building in public The Building in Public How-To Guide, Gaby Goldberg There are two widely discussed considerations for not building in public: o Increased competiton: businesses with little barrier to entry, those in competetive markets should weigh the upside of BIP with the asymitry of information they'll create for their competition o Increased scrutiny: negetive signaling (several months of high churn, revenue dips, etc) can damage customer, investor and your team's perception of the viability of the businss Considerations: The working culture at Gumroad is unique: there are no meetings, fixed working hours, or deadlines. Designed for both efficiency and work/life balance, Sahil writes and tweets about his hypotheses, experiments, and experiences building Gumroad's culture, which in turn attracts a volume of candidates that have self select into the way they work, enabling a unique working culture that would be difficult to build otherwise (eg. 30-50 interviews per engineer hire with a cost per interview of $0) Attracting talent at no cost, and eliminating meetings BUILD IN PUBLIC (8/8)
  • 44. “If you join Gumroad, my goal is that you learn almost nothing new on the day you join. The revenue and everything you should have known, you could know right now by Googling it, which I think is really important. I don’t want anyone to join the company and realize this is not the right fit… I make it really clear that I don’t like telling people what to do. I do that in the hiring process, before the hiring process, on a jobs page, afterwards… So, hiring is definitely the largest part of it – making sure you’re hiring the right kind of folks who can operate in this way – and that’s mostly a function of being really clear with people and letting them self-select out. Ultimately, the hardest thing – and I think the reason a lot of people may want to work this way but eventually won’t – is that it requires a really high bar of hiring. I interview hundreds of people for some roles...”
  • 45. Considerations: There are three widely discussed arguments against building in public: o Increased competition: businesses with low barriers to entry, and those in competitive markets should weigh the upside of BIP with the downside of the asymitry of information they'll provide their competition o Increased scrutiny: negative signaling (ex. several months of high churn, revenue dips, etc) can damage customer, investor and your team's perception of the viability of the businss o Time better spend elsewhere: It takes time to create contnet. Your time maybe spent better elewhere
  • 46. 2 History of some of the main players behind the BIP movement The Transparency Movement: What It Is, Why It’s Important And How to Get Involved 1 Playbook on how to build in public by Gaby Goldberg The Building in Public How-To Guide Recommended Reading: 3 Cheat sheet that includes metrics that can be shared, places to post and people to follow Build In Public Cheatsheet (v1.0)
  • 47. “If you join Gumroad, my goal is that you learn almost nothing new on the day you join. The revenue and everything you should have known, you could know right now by Googling it, which I think is really important. I don’t want anyone to join the company and realize this is not the right fit… I make it really clear that I don’t like telling people what to do. I do that in the hiring process, before the hiring process, on a jobs page, afterwards… So, hiring is definitely the largest part of it – making sure you’re hiring the right kind of folks who can operate in this way – and that’s mostly a function of being really clear with people and letting them self-select out. Ultimately, the hardest thing – and I think the reason a lot of people may want to work this way but eventually won’t – is that it requires a really high bar of hiring. I interview hundreds of people for some roles...” Sahil: 2 One of the key players behind the movement on its origins and benefit The Transparency Movement: Why It's Important, Buffer Blog 1 Sahil on how No Meetings, No Deadlines, No Full-Time Employees, Sahil Lavingia Recommended Reading: 3 Actionable guide to building in public The Building in Public How-To Guide, Gaby Goldberg There are two widely discussed considerations for not building in public: o Increased competiton: businesses with little barrier to entry, those in competetive markets should weigh the upside of BIP with the asymitry of information they'll create for their competition o Increased scrutiny: negetive signaling (several months of high churn, revenue dips, etc) can damage customer, investor and your team's perception of the viability of the businss Considerations: Startups "build in public" by: o Proposing ideas (ex. product design) and getting feedback o Shareing experiences/insights (ex. how you overcame roadblocks, what its like to work in the company) for the purpose of: o Galvanizing customers o Increasing traffic/marketing o Getting feedback o Attracting talent Sahil has also used this tactic to successfully raise funding, and improve the performance of his team o The SEC recently increased the limit startups can raise through crowdfunding from $1M-$5M o Sahil saw this as an opportunity to not only raise capital, but also "blur the lines between investor and customer" creating super fans or spokes people for the company by raising from his audience o 12 hours after going live on Republic.co, he raised $5M from 7,303 investors ($100-$1,000 cheque size) o Nearly 2,300 were creators on Gumroad and many more were followers of his BIP journey o As crowdfunding becomes more prevelant, an additonal benefit to BIP is leveraging your audience to finance the business 1. Raising $5M in 12 hours SUMMARY OF THE CASE STUDY Lorem ipsum, Lorem ipsum, Lorem ipsum
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