The Leadership Toolkit with Dave Berkus
From Tim Stating the Obvious by statingtheobvious
April 29, 2026 · 37 min · Season 7 · Episode 24
About this episode
Tim Staton interviews Dave Berkus about his journey from entrepreneur to super angel investor and the lessons learned in leadership and investing.
What does it take to move from entrepreneur to super angel investor, and what can leaders learn from that journey? In this episode, The Leadership Toolkit with Dave Berkus, Tim Staton sits down with Dave Berkus, a pioneering entrepreneur, tech innovator, and investor with more than 200 startup investments, to unpack the lessons he has learned building companies, backing founders, and advising leaders. Dave shares how a teenage side business evolved into a public company, how he recognized opportunity during crisis, and how he built one of the earliest hospitality software systems, technology that helped shape modern hotel reservations and was adopted by Marriott International for decades. The conversation explores the evolution of angel investing and the story behind the renowned Berkus Method, Dave’s practical framework for valuing early-stage startups before revenue. He explains what he looks for in founders, the red flags that signal trouble, why coachability matters, and why disciplined investing is often about making money before you ever exit. Tim and Dave also dive into missed opportunities, including passing on Amazon, and why failures and near misses often become a…
People in this episode
Host: Tim Staton
Guest: Dave Berkus
Topics covered
- leadership
- angel investing
- entrepreneurship
- startup valuation
- decision-making
- risk management
Keywords
- leadership
- angel investing
- Berkus Method
- startup
- entrepreneur
- decision-making
- risk
- investment
Mentioned in this episode
Organizations: Marriott International
Products: Berkus Method
Books & works: The Leader's Toolkit
Places: Amazon
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