Fail Your Way to Success

Jonathan Small has been chronicling the failures and successes of people for most of his career. From doing his first interview (with George Carlin) to his sharing dating tips as “Jake” for Glamour magazine to his stint as an editor at Entrepreneur magazine to his experience interviewing hundreds of writers on his Write About Now podcast, Small has been a fly-on-the-wall for many failure-to-success stories.

Now he’s release...

Diana Cannon has been through more than your average bear (or human).

After growing up in a dysfunctional Mormon home, she raised three kids as a single mom, uncovered deep family secrets and wrote about it all in the Legacy Launch Pad published memoir, Loose Cannons (which got her featured in the Daily Mail, Today and the LA Times Book Fair, among other places).

Post publication, just when it looked like the drama w...

Nicolas Cole has founded more successful writing businesses than perhaps anyone on earth. These include a daily writing program that has over 10,000 students, a ghostwriting academy that has over 800 students, a SaaS platform and a paid newsletter. He’s also written 10 books, been a World of Warcraft champion, accumulated over a billion views online and been published in a slew of mainstream publications.

While his failure...

There was a time where you couldn’t walk down the street without seeing someone sporting a SpiritualGangster t-shirt. (Please note: that time hasn’t really passed.) 

Well, the shirt that epitomized the spiritual seeker who was also cool was the brain child of former lawyer and yoga teacher Ian Lopatin. Despite the fact that the brand he and his wife started by making t-shirts out of their garage mushroomed into a $30 millio...

Darren Prince holds a special place in my heart.

Not only is he a powerhouse (you’ll read more about that in a second) but he was also Legacy Launch Pad’s first client—AKA the reason this company even exists.

See, many years ago when Darren and I met, we both knew he needed to write a book. The thing is, he needed a publishing company. The short version of the story is that I built one for the sole purpose of launching his...

While comedian Craig Shoemaker has been very successful—winning an American Comedy Award, writing, producing and starring in two Universal feature films, landing on IMDB’s list of 100 top comics—finding success isn’t how he’s avoided failure. 

By his own admission, he’s failed over and over again. But he now has a system for changing perspective to the point that failure doesn’t even register. He employs it in his coachin...

Charlie Hoehn is an expert at getting through to Big Name folks through cold outreach, as evidenced by the fact that he’s worked with such greats as Ramit Sethi and Tim Ferriss. He’s also—in part because of his time working with those greats—a publishing expert who’s not only released his own bestselling books but also worked on many other New York Times bestsellers. (You can find out more about working with him by going t...

There are charming and wonderful people, and then there’s Matt George. He was an early client at Legacy Launch Pad and one of my favorite people that I’ve ever worked with.

This isn’t just because he’s an amazing soul whose life mission has been to help people.

It isn’t just because he’s so warm and wonderful to be around that he attracts mentors like the original “Shark” Kevin Harrington and Chicken Soup for the Sou...

Sharon K. Gillenwater never expected to sell the company she founded for $25 million.

But that’s exactly what happened to this former working-class kid when she and her business partner sold her baby, Boardroom Insiders, in 2022.

Of course, it hasn’t been one smooth ride to the top.

That journey has been rife with challenges that Gillenwater so eloquently describes in her just released memoir, Scaling with Soul: How I Buil...

Ami Kassar once had a big, fat corporate job. Corporate suites at sporting events and a sweet, comfortable life.

Then that company went under.

While, as a nationally renowned expert on access to capital for entrepreneurs, he advises people to take time to figure out their next move, he instead started his new business the day after he was fired.

What started with a revenue of $13,000 a year has now turned into Mul...

Joe DeMaria is a self-described executive mercenary.

An entrepreneur who got started by hawking candy and soda from his home cupboard on the playground, DeMaria gets called in to help restructure multi-million-dollar companies. But before he found himself being pursued by successful CEOs, he had a business partnership that almost destroyed him.

In this episode, we talk about what he learned from that failed business ...

Michael Richman is a master of self-deprecation, which means that he may be being facetious when he claims he couldn’t get a prom date in high school, despite repeated attempts.

But he can’t deny the phenomenal success he’s achieved since then—including buying up half of his dad’s awning business and growing it to the point that he could have retired when they sold it a decade later.

Now he’s not only a thriving business coa...

When you think "convicted felon," you would not picture Craig Stanland.

The "reinvention architect," TEDx speaker and author looks like just about the most upstanding citizen you're likely to meet.

But looks can be deceiving; when Stanland was living a high-flying lifestyle many years ago, he was embezzling money to do it. And he sees his greatest failure NOT as the crime he committed (or going to jail) but what prec...

Kevin Anderson never meant to get into the publishing business after growing up in a small town in Canada before getting his PhD and graduating summa cum laude from Harvard and starting a tutoring company. Nevertheless, that tutoring company transitioned into what is now a massive publishing company that employs 30 writers and editors that have collectively worked on over 200 New York Times bestselling books and sold over ...

The founder of the Innovation Women speaking platform, she also owns the companies Innovation Nights, Carlton PR + Marketing and Lioness Magazine. 

She does what she does because she’s tired of seeing the same “male, pale and stale” speakers on stage at events. But she’s hardly against men—she says, in fact, that she’d welcome any man that wants to join a website called Innovation Women. 

In this episode, we not only dove ...

David Trent, a wealth manager who exited his company very comfortably and is now a speaker, business coach and soon-to-be-author, isn't only a master of acronyms. 

He's also someone who can compare the time he failed when coaching his son's second grade basketball team to the sort of failures he had when launching (and exiting) his business. 

In this episode we discussed how self-development books can help you overcome fai...

Tamar Hermes doesn't look like someone who struggles with self-confidence. A successful real estate investor, bestselling author and founder of a thriving mastermind, she seems to take life by the proverbial horns.

But she's the first to admit that she's been held back by a fundamental lack of belief in herself. So how has she conquered that—and what lessons can she share with the rest of us about it?

For more info, go t...

When you meet James Prince, you don't necessarily think "former criminal defense attorney." But that's exactly what he was for eight years before he became a wealth manager in Dubai.

Yet Prince doesn't see the time he spent in his former career as a waste. That's because he sees every detour—and failure—as something he would have paid money to learn.

While you're going to find out how to turn your entire attitude about fai...

Heidi McNulty seemed to have it made. After building up her net worth to over $10 million and retiring at the age of 35, she was ready to pass along everything she'd learned about finances to others.

Then the unthinkable happened: her husband, during a bout with PTSD, shot himself in front of Heidi and their children.

That's when McNulty understood why her financial stability was so important: that it allowed her the...