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 leader’s greatest teachers. Dave offers candid insights on risk, diversification, internal rate of return, and why angel investing is not for the faint of heart.

The discussion also turns to leadership through Dave’s book, The Leader's Toolkit, where he shares practical wisdom on decision-making, crisis leadership, governance, and building the right advisory board. From startup strategy to boardroom negotiations, this episode is packed with lessons on leadership, investing, and thinking long term.

In this episode, we discuss:

How Dave Berkus built and exited a pioneering software company
The origins of the Berkus Method for startup valuation
What separates investable founders from risky ones
Lessons learned from missed opportunities and failed investments
Why strong boards and governance can shape a company’s future
Practical leadership principles from The Leader’s Toolkit

If you are interested in entrepreneurship, leadership, investing, or building something that lasts, this conversation delivers wisdom earned through decades of experience.

Listen in and discover why great leadership, like great investing, often comes down to judgment, relationships, and seeing opportunity before others do.