Oct 6 • 56M

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

Episode 109

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Ripple Ventures
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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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