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.
A word from our sponsor:
At Ripple, we manage all of our fund expenses and employee credit cards using Jeeves.
The team at Jeeves helped get me and my team setup with physical and virtual credit cards in days. I was able to allow my teammates to expense items in multiple currencies allowing them to pay for anything, anywhere at anytime. We weren’t asked for any personal guarantees or to pay any setup or monthly SaaS fees.
Not only does Jeeves save us time, but they also give us cash back on our purchases including expenses like Google, Facebook, or AWS every month. New users can earn up to 3% cashback for their first 90 days.
The best part is Jeeves puts up the cash, and you settle up once every 30 days in any currency you want, unlike some other corporate card companies that make you pre-pay every month. Jeeves also recently launched its Jeeves Growth and Working Capital initiative for startups and fast-growing companies to enable more financial freedom for companies. The best thing of all is that Jeeves is live in 24 countries including Canada, US and many other countries around the world.
Jeeves truly offers the best all-in-one expense management corporate card program for all startups especially the ones at Ripple and we at Tank Talks could not be more excited to officially partner with them. Listeners of Tank Talks can get set up with a demo of Jeeves today and take advantage of our Tank Talks special with a $250 statement credit after the first $2,500 in spend or a $500 statement credit after the first $5000 in spend. Lastly, all Jeeves cardholders receive access to their Lounge Pass program and access to over 1300 airports globally.
Visit tryjeeves.com/tanktalks to learn more.
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
🎙- Favorite Podcast: Mike Maples
📰 - Favorite Newsletter/Blog: Matt Levine
📲 - Favorite Tech Gadget: Apple Watch
📈 - Favorite New Trend: Google Home
🤔 - Favorite Life Lesson: How lucky he’s been to be presented with these life opportunities