Don’t Look Down!: The Improbable Adventures and Battle-Tested Lessons of a Serial Entrepreneur by Bob Campana with Niles Howard is an inspiring, humorous, and hard-won roadmap to resilience, chronicling one man’s globe-trotting entrepreneurial journey—and the life lessons he learned about staying the course, adapting to change, and never losing sight of your vision. Authors Bob Campana and Niles Howard talk to Book Glow about the book.

What first inspired you to turn your life story into a book? Was there a specific moment when you realized your experiences could resonate with a wider audience?

I set out to write this book for my children and grandchildren, to capture my life story before the details faded. But as the stories took shape, my collaborator, Niles, pointed out that they carried lessons that could help other entrepreneurs. That’s when it shifted from a family memoir to a book with a broader message.

The book began as a personal project for your family. How did your perspective shift once you decided to write it for the public?

Writing for the public meant shifting from personal memories to teachable moments. We rewrote sections to draw out the entrepreneurial lessons behind the stories—how I handled risk, failure, and growth. It became less about me and more about what others could take away.

Don’t Look Down! mixes adventure, humor, and business lessons. How did you find the balance between storytelling and sharing practical takeaways?

The stories came first. Once we had them down, Niles and I looked for the business lessons hidden inside each one. The humor and adventure gave readers something to enjoy; the lessons gave them something to use.

You’ve built businesses in so many industries—construction, hospitality, travel, and more. What thread connects all of your ventures?

People. Whether I was building pools, running restaurants, or designing travel experiences, success always depended on understanding what people wanted and how to make them feel good about the experience. Over time, my focus shifted from making money to serving people. Ironically, that’s when I made the most money.

The subtitle mentions “battle-tested lessons.” What’s one lesson that was the hardest to learn, but the most rewarding?

Trust. You can’t build anything lasting without it, but trust will get tested. Some people let you down, but others rise to the occasion when you give them responsibility and faith. Seeing an employee grow into a leader because someone believed in them. That’s as rewarding as any profit I’ve made.

You’re candid about your flops as well as your victories. Why was it important to include those failures in the book?

Because that’s where the learning happens. Success doesn’t teach you much; failure does. My first restaurant failed because I didn’t understand the business. The second one thrived because I fixed every mistake. I tracked costs, upgraded systems, and built a strong team. The market is the judge, and if you listen, it will teach you everything you need to know.

“Stay the course, adapt to change, and never stop moving toward your vision” is a powerful motto. When has that philosophy been tested the most in your life?

In pretty much every venture I’ve started. Nothing I’ve built ever took off overnight. It was always a grind of trial and error, small course corrections, and persistence. You have to stay flexible, keep learning, and never lose sight of the long game.

The book is full of colorful stories—from hot tubs to helicopters. Is there one adventure that still makes you laugh (or cringe) when you think about it?

I flew with a buddy of mine into the Sierra Nevada mountains in my Bell 206 helicopter to fish in a remote river. We set down on a flat rock in the middle of the river. When my buddy got out, his weight shifted the balance, and the helicopter started to tilt back, nearly falling into the river. He jumped back on just in time. It’s funny now—but it sure wasn’t then.

What do you hope young entrepreneurs and readers just starting out in their careers take away from your journey?

It’s never easy. Every time you grow, the problems become bigger and more complicated. Business isn’t a straight line; it’s a long, winding journey that keeps revealing new terrain.

Looking back now, is there anything you wish you had done differently in business—or in life?

I might have avoided a few partnerships. The wrong partner can drain you faster than a bad year. Still, every misstep taught me something. You make the best decision you can with the information you have, then adjust when reality proves you wrong. The key is staying nimble enough to change course.

If readers could only remember one idea from Don’t Look Down!, what would you want it to be?

Enjoy the climb. You’ll face setbacks and detours because you don’t know what you don’t know. But persistence and adaptability will see you through. That’s what keeps life interesting.

Questions for Niles Howard

Niles, as a coauthor and business journalist, how did you approach shaping Bob’s story and voice while keeping it authentic?

I approached it less as shaping and more as listening. Bob’s voice was already there—direct, funny, full of fizz. My job was to get out of the way and let it through. Readers needed to hear Bob, not some airbrushed version. He had great stories—hot tubs, restaurants, helicopters—but what really interested me was the thread running through it all: how he handled risk, kept reinventing himself, and stayed connected to people. The hard part was what to leave out; he’s lived enough for three lifetimes. My goal was for readers to feel like they’re sitting across from Bob at breakfast, hearing him tell it straight. Probably with a grin. Definitely with a lesson.

How did your collaboration work in practice—did you record conversations, trade drafts, or brainstorm together?

We talked for a couple of hours every Tuesday morning for six months. The conversations wandered—from steerage out of Italy to a royal fishing hole in Nepal, a business partnership from hell, and a backyard bonfire gone rogue. I never knew where we were headed, but that’s where the good stuff hides. Over time, a bigger story came into focus: ambition, long shots, failure, resilience, and the sheer nerve it takes to keep going. We realized we were sitting on more than a family memoir. Bob made my job easy—he told the truth, even when it hurt. I just had to make sure that honesty stayed on the page.

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