Today, we’re welcoming Bob Campana, a California-based serial entrepreneur with more than 40 years of experience building businesses across hospitality, travel, real estate, and aviation.
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From hot tub manufacturing to founding the beloved Redwood Café in Modesto, to leading Redwood Café Tours across Europe, Asia, and Oceania, Bob’s career is a living case study in adaptability, optimism, and grit.
He’s also the author of the book Don’t Look Down! The Improbable Adventures and Battle-Tested Lessons of a Serial Entrepreneur, where he shares candid lessons learned from a lifetime of figuring it out as he went. Bob has his own entrepreneurship podcast, continuing his mission to share what really happens behind the scenes of business building.
1. A Lifetime of Reinvention
Bob, you’ve built businesses in very different industries—from manufacturing to hospitality to aviation. Looking back over 40 years, what allowed you to keep reinventing yourself rather than getting stuck in one version of success?
2. Risk, Fear, and the Title “Don’t Look Down!”
Your book title says a lot. Don’t Look Down! suggests both courage and consequence. How have you learned to take risks without being reckless—and what’s one moment when looking down might have stopped you if you’d let it?
3. Building Places That Connect People
Redwood Café became more than a restaurant—it became a community hub, and now it’s evolved into Redwood Café Tours around the world. What do you think makes an experience or a business truly memorable to people? (Bob recommends two books. “Moments of Truth: How the SAS President and CEO Adapted to the New Customer-Driven Economy” by Jan Carlzon. “Setting the Table: The Transforming Power of Hospitality in Business” by Danny Meyer.)
4. Lessons Earned the Hard Way
Your book promises “battle-tested lessons,” not theory. What are one or two hard-earned truths about entrepreneurship that you wish more people understood before they start their first venture?
5. What’s Next—and Why Keep Going?
You’re still expanding into real estate and aircraft leasing, writing books, and launching a podcast. What keeps you energized at this stage—and what advice would you give to entrepreneurs who wonder if it’s too late to start something new?
Bob, if you could leave our listeners with one mindset or principle that’s helped you navigate uncertainty over four decades, what would it be?
