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/

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.