20VC: Fundraising Wisdom that is Total BS; Dilution, Meeting Associates, Taking the Highest Price, Always Be Raising | Why Second Time Founders Are More Investable & Why Not To Hire People Out of College with Dan Siroker, CEO @ Limitless

Dan Siroker is the Co-Founder and CEO @ Limitless, a personalized AI powered by what you’ve seen, said, or heard. For his latest funding round, Dan took an unusual approach resulting in 1,000 preliminary offers with valuations as high as $1BN — and resulted in a $350 million Series A valuation. Prior to founding Limitless, Dan was the Founder of Optimizely, scaling the company to $120M in ARR and raising from some of the best in the business including Peter Fenton @ Benchmark who led the Series A.

In Today’s Episode with Dan Siroker We Discuss:

1. Serial Entrepreneurs are More Investable:

• Why would Dan always prefer to invest in serial entrepreneurs than first time founders?

• How do serial entrepreneurs approach team building and size of team differently?

• How do serial entrepreneurs approach focus and prioritisation differently?

• How do serial entrepreneurs approach pivoting differently to first time founders?

• What is Dan’s advice from Elad Gil and YC’s Dalton Caldwell on when to pivot?

2. The Secret to Fundraising: How to Speak VC

• Should founders always be raising?

• What is the right thing to respond to investors when they reach out to you outside of a round?

• What question are investors really asking when they ask, how much are you raising?

• How should founders approach valuation, what should they say when they are asked for it?

• How can founders create urgency in a funding round? What works? What does not?

3. How to Raise the Best Funding Round:

• Should founders engage with associates or only worth it with decision-makers?

• Why should founders always choose the investor who is on the early arc of their career?

• Why was Dan’s first meeting with Peter Fenton the best meeting he has ever had with a VC?

• Why does Dan believe that taking the highest price is never the right answer?

• To what extent does having a true Tier 1 VC lead your round, change the game for your company?

4. Dan Siroker: AMA:

• How did becoming a father change the way that Dan operates?

• Why is Dan scared we might see technological progress stall for the next 20 years?

• Why did Dan not do YC the second time around with Limitless?

• What is the story of how Optimizely nearly bought Amplitude?