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

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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