Life Advice From a Serial Entrepreneur

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Jimmy Tomczak spent his early adulthood founding a number of companies and startups, the most well-known being Paper Feet, a foot apparel brand that turned recycled billboard vinyl into sandals.

For many, the fast-paced startup business world is all-consuming. Many entrepreneurs enter the market with a clear mission and deep, emotional stake in their company. But in the craziness of the day-to-day, it can be easy to lose sight of the big picture, and in some ways, even that basic sense of purpose.

After appearing on Shark Tank, Jimmy decided to step away from the standard entrepreneur lifestyle for a bit in favor of traveling the world and connecting to as many likeminded people as possible. Regain that sense of perspective.

He collected his insights in a new book called Lakeside & Tide, a guide for how entrepreneurs can live their best lives now. We had a chance to catch up with Jimmy about his work.


Dustin Clendenen: How has your perspective and life changed since your travels and connecting with all these fellow entrepreneurs?

Jimmy Tomczak: You’ve heard that saying, “You are the average of the five people you spend the most time with.” Travel helps you connect with more people faster so that you can learn more and at an accelerated rate, deep-diving into immersive experiences with fellow entrepreneurs: masterminds, retreats, adventures. I’d say these experiences have led to some of my biggest breakthroughs. Intentional travel is about improving yourself and your life so that you can help improve the lives of others. When you travel there is so much to see and do. But most importantly, learn. Learning is my number one favorite thing.

DC: What can other entrepreneurs do to stay centered, focused and committed to purpose without having to take such drastic measures to recharge?

JT: I spent an entire year traveling: East Coast, West Coast, middle of nowhere, Bangkok, Canada, Mexico, North, South, East, West. I told myself my “grand finale” would be another trip to the Nevada desert to revisit Burning Man. My first experience was so transformative, I could only dream about what another go would be like now, this time with twelve friends and entrepreneurs from all over the world. We packed into an overloaded RV and trekked from Detroit to Black Rock City and back.

The Burn was everything we hoped and more, but I said I’d be done. Instead, when I got back I heard from another friend about a new program: the world’s first “Decelerator.”

I’d heard of accelerators. It seemed like every organization had a new take on helping entrepreneurs grow their businesses better and faster. This program was for the entrepreneur already taking on too much. The specific focus was focusing.

I applied and after a few interviews was accepted. I was the youngest entrepreneur to join a small group of elite designers, speakers, and business owners: an owner of a global grocery chain, a “bubbleologist,” the founder of a theater, all convening on an island in Bali with no wifi, no cell phone, and no excuses to not get back to basics and recharge.

For me, I felt I had to go that extreme. Similarly, sometimes people do Vipassana experiences, Ayahuasca, and retreats that cost more than some cars. The truth is that once you experience something like that, you can change. You realize you can go there—within—any time you want, to get exactly what you need. It’s about self love, commitment, and letting go…

Sometimes, less is more. Sometimes, a whole lot more. I write about that in my book because I began writing it while embracing these once-in-a-lifetime opportunities.

DC: What are the core fundamentals of “living your best life, now?”

JT: Living your best life now is about acknowledging that life isn’t always a “hop-a-plane-and-party-with-global-digital-nomads” kind of non-stop ride. You have to embrace both the highs and the lows equally. Yes I’ve cruised around Turkey and Greece on a boat with twenty of my best friends in the world. But I’ve spent far more time alone and at peace in my home writing, reading, and doing my deepest work in quiet solitude where pretty much no one can find me.

The key is balance.

Lakeside & Tide breaks down some of these very big concepts into bite-size pieces that anyone can try anytime. You can go as far and as fast as you want, at purely your own speed.

DC: From where you are now, what advice would you like to give to your younger self and aspiring entrepreneurs as well? 

JT: Get the help you need.

There’s no need to go it alone. Ask for help. Ask for what you need. Be willing to give to others to support them in their meaningful work. And the circle goes around like that. Love more!

Mentors are so powerful. So get a mentor. But also be a mentor to someone. Teaching is the highest form of knowing. So what do you know? Learn it yourself somehow and then share it.

I’d also say read. Pick up a book. Type your “unanswerable question” into Google and see what other people are saying. Then follow your heart combined with the logic of what works for now and for you and for the future. But don’t care too much about what other people think. And don’t take other people’s advice without fully considering your own.

One of the reasons I wrote my book was because I’d be having conversations that looked very similar with multiple people: how to start a business, the basics of self-actualization, the purpose of personal growth, how to connect…

I realized I couldn’t go as deep or give as much help as I could in the time we had together and given the time constraints of my own commitments. So I wrote a book so that anyone can encounter a life’s worth of experiences—my own—in brief, but more importantly, see that there’s nothing stopping them from going after their own meaningful experiences and starting right now, the best time in the world to do anything.


Lakeside & Tide is available for purchase at

Learn more about Jimmy’s work at

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