Want to move from side hustle to startup? Ditch your backup plan, says investor and guest 'Shark Tank' shark Matt Higgins

Want to move from side hustle to startup? Ditch your backup plan, says investor and guest 'Shark Tank' shark Matt Higgins
Matt Higgins, author of "Burn the Boats" is a guest shark on "Shark Tank"Eric McCandless/Getty Images
  • Matt Higgins, cofounder of RSE Ventures, has had a successful career, despite a tough upbringing.
  • Higgins' new book, "Burn the Boats," urges people to forego the backup plan to fulfill their goals.

Side hustlers and would-be entrepreneurs will often have a backup plan to their dreams, just in case things don't work out.

But that safety net might be preventing them from achieving their full potential, according to a book by Matt Higgins, an investor and guest shark on "Shark Tank."

Higgins' book, titled "Burn the Boats," urges entrepreneurs to find the right moment, and then go all-in on their goals.

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"What holds us back from fully committing to our purpose are these metaphorical boats that tell us to retreat," Higgins told Insider. "When you leave a door open for retreat, it undermines your resolve. You need the pain of potential failure to drive you to take extraordinary acts to succeed."

Scared? That's the point, according to Higgins. It's that kind of productive anxiety that drives entrepreneurs. Without risk, he said, reward is more elusive. Even flourishing founders will find ways to continuously access pools of doubt or fear that drive them forward toward the next thing.


For Higgins, there was no plan B. The cofounder of RSE Ventures and investor in such brands as Momofuku, VaynerMedia, and Magnolia Bakery, he grew up poor in Queens, New York, the youngest child of a single mother with depression and other health problems.

Higgins started working at age 10, then dropped out of school at 16 so he could get his GED and attend college — and start earning real money – as quickly as possible. His mother died just as his career began to take off.

Early on, Higgins worked in communications for dotcom-era grocery startup Kozmo.com. He was New York City Mayor Rudolph Giuliani's press secretary on 9/11, and later chief operating officer of the Lower Manhattan Development Corporation. RSE Ventures was founded in 2012, and Higgins also held executive roles with the New York Jets and Miami Dolphins.

Moving from side hustle to startup

While his resume looks like nonstop progression, Higgins shares in the book the tradeoffs involved, such as when he decided to leave a "dream job" as an operations executive with the New York Jets.

Want to move from side hustle to startup? Ditch your backup plan, says investor and guest 'Shark Tank' shark Matt Higgins
RSE Ventures

"I felt like I wasn't using all my skills." he wrote. "I wanted to be in a place of perpetual growth and disruption, not presiding over things that were generally fine. So I quit. Crazy, right?"


That decision would lead to his connecting with real estate developer Stephen Ross, owner of the Miami Dolphins and later Higgins' cofounder of RSE Ventures.

For those working a side hustle, it's tough to know when the time might be right to quit your day job.

"When you are in the land of the side hustle, you're trying to identify that which would be fulfilling enough, rewarding enough, and sustaining enough to be your plan A," Higgins told Insider.

If you're looking for financial guarantees from day one, however, that's the wrong goal. "If that's your framework, you'll never go all the way in," he added. The trick is to figure out what is the level of risk you can tolerate, but not eliminate it completely. Otherwise, he said, you are in danger of losing focus on the best possible outcome.

Optimizing anxiety while avoiding burnout

Higgins dedicates an entire chapter to optimizing anxiety, including tools for letting it spiral out of control.


"Anxiety is a power source," Higgins told Insider. "Like nuclear power it needs to be unleashed the same time it's contained or you have a total meltdown."

Burnout is common for anyone pursuing their passion. "There's a cost to being all-in because the stakes are always very high," he said. "While it's propelling you to greatness, it does grind you down."

He advises identifying the specific parts of your life that are essential to your well-being, and protecting them — but defining them narrowly so that you're not adding stress by worrying about things that ultimately don't matter.

Higgins also tries to meditate every day, citing examples of other leaders from Ray Dalio to Bill Gates who swear by the practice.

Mainly though, you have to learn to let go when things don't go your way. He wrote, "Do what you can, forgive yourself when you don't achieve perfection, and keep trying."