A Podcast for People Who’ve Broken Things in the Past.

And a place filled with stories of the incredible entrepreneurial growth that occurred as a result. Join us as we dive into breakage through a business lens. You might even gain the motivation to completely shatter something

— for the better — yourself.

The Story Behind

How I Broke That

How I Broke That came to be after host Josh Chernikoff experienced significant breakage himself, and witnessed his business excel because of it. Chernikoff became intrigued by how events that may seem unfortunate at the time can actually turn into entrepreneurial success. For the detail-filled description, take in our introductory blog post here.

Coming soon:

Arianna Davis

Author of the best-selling book,

“What Would Frida Do?”

John Gamba

A serial entrepreneur dedicated to transforming education

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Click here to be considered for a spot on the show

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How I Broke That

For better or worse, most business owners have “broken” themselves, their business, or their industry at some point. Josh Chernikoff, a serial entrepreneur who has successfully grown (and broken) three bootstrapped businesses, interviews other entrepreneurs to learn how they built, broke, and rebuilt within their industry.


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Meet your host

Josh Chernikoff


“After all, breakage isn’t always bad. In fact, breaking things, including yourself, is completely okay when the experience leads to something better.”

Hi, I’m Joshua Chernikoff. I’m an entrepreneur and business owner who has founded and sold two education businesses in the past. I currently spend my time supporting our nation’s post-pandemic educational comeback through the founding of Flex Tutors and the coaching of multiple companies in the education space. I’ve experienced the positive effects of breakage myself, and I’m looking forward to learning from others who’ve grown from their most challenging moments as well.

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