March 16, 2018

To Be Funded or Not To Be Funded, SaaStr Annual 2018


Our biggest takeaways from “To Be Funded or Not To Be Funded” at SaaStr Annual 2018.


Amy Pressman — Co-Founder & President / MedalliaTeddy Schleifer — Sr Reporter / Recode


One company, two sides of the funding debate. Medallia, #7 on Forbes’ 2017 top 100 private SaaS companies, bootstrapped for 10 years, then took $255M in investment from Sequoia Capital over the past 6+ years. Company co-founder Amy Pressman talks about the pros and cons of being bootstrapped vs investor-backed and provides tips for entrepreneurs about how to go it alone (even in Silicon Valley!).



“Was it [bootstrapping] ever challenging?” — Teddy

Nah, piece of cake 😉

“I don’t know what kind of help Sequoia would have given us in the early stages” — Amy


  • Control over how they spent their time and resources
  • Clarity on focus because your survival depends on it
  • Business Problems, not Board Problems: Amy mentioned how, when she was bootstrapped, she was the only Bootstrapper in a Co-founder group. While she was talking about problems in her business, everyone else was talking about Board Dynamics and problems with their investors

Being funded


  • Name recognition and credibility
  • Without the capital resources of being funded, you have [or get?] to be more creative. With funding, you can operate in more traditional swim lanes (which is not necessarily a good thing)

Tying Ambition to Funding is Demeaning imo

“By not accepting venture capital, you’re building a less ambitious company” — Teddy on what some VC’s would say about not taking VC money

In the words of E-40 “Nope.” Capital raised does not equal Founder ambition. Ambition is not one-sized fits all.

Considering Giving up Equity

You really want to think about what you want to do with your company. How large do you want to grow? How quickly do you feel you need to do it? What market are you in and how competitive is it? And many more considerations…

Basically, frame your capital strategy around where you think you want to be and how you think you want to get there. Get resources, go heads down on your plan, come back up and reassess.