Evolving as an Entrepreneur - Matt Wensing BoS 2021.pdf

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Evolving as an Entrepreneur - Matt Wensing BoS 2021 Over the past couple of years, Matt, a committed bootstrapper, focused on building the product and growth strategy for Summit, his second startup. Matt came to realize that to build the business he wanted to create, bootstrapping was not the right path – for the company or for him as an entrepreneur. This time, pursuing meaningful funding was a better route to a successful outcome. In this BoS talk, Matt shares his thinking process, the context and the pivotal moments that led to this big decision. You can watch the talk, with slides and transcript at https://businessofsoftware.org/talks/evolving-enrepreneur/

Business

Evolving as an entrepreneur ...
@mattwensing 🐙
#thisisnotadvice

A little about my 1st rodeo
(Riskpulse):
Bootstrapped SaaS to profitability, 2004-2012.
Co-founder (CTO), built a team of 15.
Raised $3.3m, sold to private equity & DHL in 2019.
Along the way, co-raising 4 children.

Every startup is a journey through this table.

It's time to build ...
financial planning SaaS.
@usesummit

Product, v1: Fill out a
form, get a forecast.

Early 2019: Launch v1,
validate willingness to pay.

By late 2019, lots of feedback
and free users, revenue is
slow going ...

Raise $315k in
convertible debt, start
working on v2.

Summer 2020: launch
v2 (more flexibility).

Market responds, raise
an additional $650k
debt.

More powerful, more
heavy, more consuming ...
🌃

More powerful, more
heavy, more consuming ...
... "the long winter."

45 days (of hellish
uncertainty) later ...

Time & the
inescapable costs of
entrepreneurship.

Binary = clarity.
Let's go big,
or go home.

@mattwensing 🐙
@usesummit
Keep evolving.

MTBiz is for you if you are looking for contemporary information on business, economy and especially on banking industry of Bangladesh. You would also find periodical information on Global Economy and Commodity Markets. Signature content of MTBiz is its Article of the Month (AoM), as depicted on Cover Page of each issue, with featured focus on different issues that fall into the wide definition of Market, Business, Organization and Leadership. The AoM also covers areas on Innovation, Central Banking, Monetary Policy, National Budget, Economic Depression or Growth and Capital Market. Scale of coverage of the AoM both, global and local subject to each issue. MTBiz is a monthly Market Review produced and distributed by Group R&D, MTB since 2009.

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1. Evolving as an entrepreneur ... @mattwensing 🐙 #thisisnotadvice

2. A little about my 1st rodeo (Riskpulse): Bootstrapped SaaS to profitability, 2004-2012. Co-founder (CTO), built a team of 15. Raised $3.3m, sold to private equity & DHL in 2019. Along the way, co-raising 4 children.

3. Every startup is a journey through this table.

4. What will my journey be this time?

5. Last time.

6. Decision 1: Solo founder.

7. 1 co-founder ≈ 3 rounds of funding

8. What about this axis?

9. Bootstrapping?

10. Then (2009) ... 2017 ...

11. (Family) Business of Software 2019 ...

12. Decision 2: Optionality. ?

13. You can have it all? ?

14. $200k pre-seed. ?