Dan Siroker: Second-Time Founders Are More Investable & Why Not To Hire People Out of College |E1153

ℹ️ EPISODE INFO

Released

May 15, 2024

Duration

1h 17m

Channel

The Twenty Minute VC

Watch on YouTube

▶ Open ↗

📝 EPISODE DESCRIPTION

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. ----------------------------------------------- Timestamps: (00:00) Intro (00:47) Background (01:35) Yeses & Nos as Turning Points (06:45) First-Time Founders vs. Serial Entrepreneurs (14:53) Biggest Mistakes in Leadership (16:36) Navigating Enterprise: Advice for Founders (19:25) Title Inflation: A Common Founder Mistake (24:20) Lessons on Secondaries & Motivation (30:46) Negotiation Tactics (35:06) Steps for Structuring Pronoun Fundraisers (41:46) Engaging with Associates & Practicing the Pitch (58:07) The Best Venture Meeting (59:58) Navigating the AI Investment Landscape (01:07:42) Quick-Fire Round ----------------------------------------------- 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?

1. 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?

1. 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?

1. 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? ----------------------------------------------- Subscribe on Spotify: https://open.spotify.com/show/3j2KMcZTtgTNBKwtZBMHvl?si=85bc9196860e4466 Subscribe on Apple Podcasts: https://podcasts.apple.com/us/podcast/the-twenty-minute-vc-20vc-venture-capital-startup/id958230465 Follow Harry Stebbings on Twitter: https://twitter.com/HarryStebbings Follow Dan Siroker on Twitter: https://twitter.com/dsiroker Follow 20VC on Instagram: https://www.instagram.com/20vchq Follow 20VC on TikTok: https://www.tiktok.com/@20vc_tok Visit our Website: https://www.20vc.com Subscribe to our Newsletter: https://www.thetwentyminutevc.com/contact ----------------------------------------------- #20vc #harrystebbings #dansiroker #limitless #founder #ceo #venturecapital #startup #hiring #fundraising

🎤 SPEAKERS

• Dan Siroker

  guest

• Harry Stebbings

  host

🧾 EPISODE SUMMARY

In this episode of The Twenty Minute VC, featuring Dan Siroker and Harry Stebbings, Dan Siroker: Second-Time Founders Are More Investable & Why Not To Hire People Out of College |E1153 explores dan Siroker Explains Smarter Fundraising, Hiring, And Second-Time Founders’ Edge Dan Siroker, founder of Optimizely and Limitless, unpacks what he learned building, pivoting, and scaling companies, and why second-time founders are often more investable and effective. He contrasts first- vs second-time founder behavior across focus, hiring, fundraising, and control, and explains why following his gut would have avoided some of Optimizely’s biggest missteps. A large portion of the discussion centers on running fundraising processes intelligently—how to think about valuation, dilution, investor minimums, signaling, boards, and secondary liquidity for employees. He also covers building lean senior teams (and why he doesn’t hire straight out of college), launching products well, and why problem-obsessed founders—not AI-for-AI’s-sake—will win.

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