Tank Talks
Tank Talks By Ripple Ventures
Darrell Silver of Unbundle Studio on Exiting Two Startups for $100M+, Launching a Venture Studio and Being an LP in Venture Funds

Darrell Silver of Unbundle Studio on Exiting Two Startups for $100M+, Launching a Venture Studio and Being an LP in Venture Funds

Episode 109

Once is lucky, twice is good. And our guest today is good. Darrell Silver, Founder and CEO of Unbundle Studio, has sold two companies for over $100M and he’s using that experience to start investing. We dig into why Darrell decided to help create tech companies with underappreciated founders in a venture studio model and the mindset needed for running the studio completely off his own balance sheet.

About Darrell Silver:
Darrell Silver runs Unbundle Studio, a venture studio that launches tech companies with underappreciated founders. He is also a board member, advisor, and investor across EdTech and child advocacy.

He co-founded+CEO'd+sold two companies: Thinkful (acquired by Chegg) & Perpetually (acquired by Dell).

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In this episode we discuss:

02:33 Darrell’s journey into Tech
04:51 Darrell’s experience pitching Jason Calacanis and TechCrunch Disrupt
08:21 Building Thinkful and selling to Chegg
11:02 Best practices for acquihires and retaining senior talent
13:00 Evaluating deals by weighing the best alternative
15:46 Why you can’t BS your way through an M&A process
17:32 Why Darrell launched Unbundle Studio
21:41 The thesis behind Unbundle Studio
23:25 Types of founders Unbundle is looking for
24:22 Why Darrell is using his own money to start Unbundle
26:01 How the traditional venture model doesn’t account for profitable businesses
27:27 Darrell’s experience as an LP
28:38 Why he sticks to his expertise when investing
30:50 What he looks for when he invests
33:06 The importance of good board members
35:55 Building your networks
37:05 What he learned from Mike Maples at Floodgate
38:36 Redflags people should avoid when pitching him as an LP
39:50 How Darrell adds value as an LP
41:16 Why being a board member is philanthropic
42:44 Advice for new LPs
44:39 The best career advice he’s gotten as an LP
45:50 Why he’s building a workshop with his dad

Fast Favorites

  1. 🎙- Favorite Podcast: Mike Maples

  2. 📰 - Favorite Newsletter/Blog: Matt Levine

  3. 📲 - Favorite Tech Gadget: Apple Watch

  4. 📈 -  Favorite New Trend: Google Home

  5. 📚 - Favorite Book: Hitchhiker’s Guide To The Galaxy, Grinding It Out

  6. 🤔 - Favorite Life Lesson: How lucky he’s been to be presented with these life opportunities

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Tank Talks
Tank Talks By Ripple Ventures
Join your host, Matt Cohen, Founder & Managing Partner at Ripple Ventures for weekly conversations with leaders in the startup ecosystem discussing the truth about investing, building and running startups.