Three Exits in 10 Years: Lessons from Serial Entrepreneur Iñaki Berenguer

Founders in Arms

Iñaki Berenguer is a serial entrepreneur with three successful exits: Pixable (sold to Singtel), Clink (sold to Thinking Phones), and CoverWallet (sold to Aon for $300M). He's now a partner at Flive Ventures, a $100M fund investing at the intersection of AI and healthcare, and president and co-founder of Ipronics, an AI infrastructure company for data centers.

What you'll learn:

1. How Iñaki built CoverWallet from 0 to $100M in premium revenue and 400 employees in just 4 years
2. Why he'd rebuild his 250-person company with only 10 people in the AI era
3. The hidden time cost of scaling teams: 40% of CEO time spent on HR, hiring, and one-on-ones
4. How strategic partnerships with potential acquirers create acquisition optionality
5. Why investment bankers matter: the difference between 3-month and 8-month due diligence timelines
6. The critical mistake of taking common stock vs. preferred in acquisition deals
7. Why "paranoid optimist" is the ideal founder mindset
8. The lifestyle reality check: VC work vs. founder intensity and what actually counts as "high pressure"
9. Reference check strategies that reveal integrity under pressure
10. How luck and timing determine exits more than founders want to admit

In this episode, we cover:

(00:51) Iñaki's journey: three companies, three exits across different industries

(03:21) Why Pixable's "always on" consumer product was harder than enterprise

(09:04) The decision to sell CoverWallet despite investor pressure to keep building

(12:20) Product-market fit doesn't exist in AI: markets change faster than products

(19:43) How Iñaki would rebuild differently: from 250 employees to AI agents

(22:32) The real time cost of hiring: 100 employees = 1,000 interviews

(27:16) M&A lessons: why time kills deals and investment bankers matter

(29:03) Building optionality through strategic partnerships with potential acquirers

(32:37) The fulfillment of building vs. investing: team wins and external validation

(36:23) Why founders struggle to celebrate wins that took years to achieve

(40:25) The "paranoid optimist" mindset: assuming someone is always working harder

(42:14) AI in healthcare: the most underhyped opportunity

(45:20) Comparing entrepreneurial cultures: Silicon Valley vs. New York vs. Europe

(46:16) The biggest mistake: not doing enough reference checks on people

(48:44) What drives founders: proving doubters wrong, not money