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 Tech04:51 Darrell’s experience pitching Jason Calacanis and TechCrunch Disrupt08:21 Building Thinkful and selling to Chegg11:02 Best practices for acquihires and retaining senior talent13:00 Evaluating deals by weighing the best alternative15:46 Why you can’t BS your way through an M&A process17:32 Why Darrell launched Unbundle Studio21:41 The thesis behind Unbundle Studio23:25 Types of founders Unbundle is looking for24:22 Why Darrell is using his own money to start Unbundle26:01 How the traditional venture model doesn’t account for profitable businesses27:27 Darrell’s experience as an LP28:38 Why he sticks to his expertise when investing30:50 What he looks for when he invests33:06 The importance of good board members35:55 Building your networks37:05 What he learned from Mike Maples at Floodgate38:36 Redflags people should avoid when pitching him as an LP39:50 How Darrell adds value as an LP41:16 Why being a board member is philanthropic42:44 Advice for new LPs44:39 The best career advice he’s gotten as an LP45:50 Why he’s building a workshop with his dad

Fast Favorites

* 🎙- Favorite Podcast: Mike Maples

* 📰 - Favorite Newsletter/Blog: Matt Levine

* 📲 - Favorite Tech Gadget: Apple Watch

* 📈 - Favorite New Trend: Google Home

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

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

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

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