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.
?

15.
It's time to build ...
financial planning SaaS.
@usesummit

16.
Product, v1: Fill out a
form, get a forecast.

17.
Early 2019: Launch v1,
validate willingness to pay.

18.
By late 2019, lots of feedback
and free users, revenue is
slow going ...

19.
Raise $315k in
convertible debt, start
working on v2.

20.
Summer 2020: launch
v2 (more flexibility).

21.
Market responds, raise
an additional $650k
debt.

22.
More powerful, more
heavy, more consuming ...
🌃

23.
More powerful, more
heavy, more consuming ...
... "the long winter."

24.
More powerful, more
heavy, more consuming ...
😱

25.
"The Call"

26.
45 days (of hellish
uncertainty) later ...

27.
Time & the
inescapable costs of
entrepreneurship.

28.
Decision 2: Optionality.
?

29.
Decision 3: Optionality.
🚶

30.
Binary = clarity.
Let's go big,
or go home.

31.
One more swing. Team ++.

32.
The Point of No Return

33.
All in.
🔥
🔥
Burn the boats.

34.
Launch private beta,
June 2021.

35.
July 14, 2021.

36.
Next 30 days (August 2021).

37.
v2 redux?
❓

38.
September month-to-date.

39.
Is this "it" ... ?

40.
@mattwensing 🐙
@usesummit
Keep evolving.