Three Exits in 10 Years: Lessons from Serial Entrepreneur Iñaki Berenguer
Founders in Arms
Intro
Hosts introduce Iñaki Berenguer, summarizing his three exits and current roles, and set episode themes.
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:
- How Iñaki built CoverWallet from 0 to $100M in premium revenue and 400 employees in just 4 years
- Why he'd rebuild his 250-person company with only 10 people in the AI era
- The hidden time cost of scaling teams: 40% of CEO time spent on HR, hiring, and one-on-ones
- How strategic partnerships with potential acquirers create acquisition optionality
- Why investment bankers matter: the difference between 3-month and 8-month due diligence timelines
- The critical mistake of taking common stock vs. preferred in acquisition deals
- Why "paranoid optimist" is the ideal founder mindset
- The lifestyle reality check: VC work vs. founder intensity and what actually counts as "high pressure"
- Reference check strategies that reveal integrity under pressure
- 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
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