New Book — David Hilbish

Passport
to Profit

How Travel Taught Me to Build, Scale & Sell Businesses

Get the Book on Amazon

Available in Paperback & Kindle

Passport to Profit book cover
84
Countries Visited
5
Businesses Built
30+
Years in Business
2025
Published

Two journeys.
One lesson.

Every chapter opens on a real expedition — crossing the Drake Passage to Antarctica, drinking at the base of Mount Everest, queuing at a snowy Croatian border — and lands on a clear, honest business lesson. Business books don’t have to be boring.

Travel is a simple metaphor for nearly every aspect of the entrepreneurial journey. The storms, the wrong turns, the moments of clarity at altitude. This book takes you on both journeys in one compressed timeline.

“Venturing into the Drake Passage was akin to taking the leap into entrepreneurship — the thrill of the unknown mixed with a healthy dose of trepidation. Success, whether at sea or in business, doesn’t magically materialize on calm waters; it’s about harnessing resilience, adaptability and a willingness to navigate rough seas.”
— From Chapter 1: Travel & Business

Board this flight with a plan.
Land with one too.

✈️

Decide if entrepreneurship is right for you

See if you have the right temperament, timing, and tolerance for risk — before you bet everything on it.

🧭

Think like an entrepreneur

Deal with pressure, get comfortable being uncomfortable, and build the mental habits that separate builders from dreamers.

🗺️

Plan your journey

Build a real roadmap for your business and define the type of company you want to build — before you start digging foundations.

🏗️

Build the right way

Products, teams, processes, and the skills needed to run a successful company — the stuff that actually makes businesses work.

🛬

Exit on your terms

Start planning your exit on day one. Avoid the trap of becoming a passenger in your own business when it matters most.

🌅

Build your encore life

What comes after selling your company — the opportunities, the challenges, and the questions most people forget to ask.

You belong on this flight if…

🚀

You want to start a business

You have the idea, the drive, and the restlessness — but you are not sure if you have what it takes or where to begin. This book helps you decide honestly and start smart.

📈

You are already running one

You built something real but growth has plateaued, the team is stretched, and the operating model needs a rewrite. The middle chapters were written for you.

🛬

You are thinking about the exit

Whether you are five years out or five months out, the time to prepare is now. Most owners wait too long. David shares what he learned the hard way about timing, valuation, and what comes next.

🌍

You are a traveler who thinks in lessons

You believe the best education happens outside the classroom — in airports, on expedition ships, at altitude. This book was written in that same spirit.

Your flight plan.

Departure Gate

Getting off the ground

Everything you need to think through before you commit — and once you do, how to build it right from the start.

  • Can You Learn Entrepreneurship?
  • Embracing Risk & Uncertainty
  • Build The Right Team
  • Build A Great Product
  • Go Where Others Aren’t
  • Sell Or Die: Why Sales Is First
Fly the Plane

Running the business

The day-to-day and year-to-year of actually operating a growing company — systems, people, culture, and the hard calls.

  • Systems Beat Hustle
  • The Founder’s Dilemma
  • Build Company Culture
  • Navigating Failure
  • Overcoming Challenges
  • Exit Readiness Is Day One Work
Taxiing In

Landing on your terms

The smart exit, life after the sale, and building a second chapter that’s as intentional as the first.

  • The Smart Exit
  • Career 2.0 / 3.0
  • Build Your Encore Life
  • Practical Tips & Resources
Passport to Profit by David Hilbish

David Hilbish

David Hilbish is a serial entrepreneur, operator, and adventure traveler based in Chicago. Over 30 years he has built, scaled, and sold multiple companies — and has consulted on the launch or turnaround of dozens more through PresumeNothing, his firm of senior operating partners.

He is also a certified flight instructor, a PADI scuba instructor, and has 84 countries stamped in his passport — most of them places you’ve either never heard of or have only seen on the Discovery Channel. The lessons he has drawn from both adventure travel and business are the engine behind this book.

Crain’s Chicago Business named his company Augmentity Systems one of the 50 fastest-growing companies in Chicago. He has been teaching — in cockpits, underwater, and in boardrooms — for over 25 years.

Airline Transport Pilot FAA Flight Instructor PADI Scuba Instructor Crain’s Fast Fifty 84 Countries Purdue University

Ready to board?

Start the journey that turns travel stories into business strategy — and your ambition into a plan worth executing.

Get the Book on Amazon

Available in Paperback & Kindle