Fail Your Way to Success

On the outside, Jessica Zweig had it all. She’d built an award-winning personal branding agency that worked with such companies as Google and Pinterest. She was the beautiful girl with the yellow branding on her popular social media feeds.

And yet inside, she was falling apart.

After a transformative experience in Egypt, she was able to rebuild her life, redefining what success and failure mean to her. Now she helps other women avoid falling apart in their quest to subscribe to the patriarchy and other man-made constructs.

She documents her entire journey and provides tips for others who want to follow in her stead to use in her new book, The Light Work: Reclaim Your Feminine Power, Live Your Cosmic Truth, and Illuminate the World.

In this episode, we talk about all of this and more—including how to use your calendar settings to get in the right frequency, why women should reconsider traveling during that time of the month and how chasing success is overvalued.

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 released a book made up of the origin stories of some of the writers he’s interviewed, which I’m proud to say Legacy Launch Pad has published. With insights from as wide a variety of people as Killers of the Flower Moon author David Grann to 90s fashion queen Betsey Johnson, Write About Now reveals the failures and successes of a succession of greats.

In this interview we talked about the main qualities successful people have in common, our shared experience starting our careers working at parenting magazines and why many companies would be far better off sharing the struggles of the founder, among many other topics.

For more info, go to www.failyourway.com.

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 was done, the sh*t hit the fan again. In this episode, Cannon talks about falling apart, coming together and how bouncing back from failure requires a belief in something that truly matters to you.

For more info, go to www.failyourway.com.

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 failures may not be obvious from the outside, they’ve existed. These include holding onto employees that didn’t care about their jobs, building a business only to find himself miserable and thinking of business success as the number of team members you have.

He’s also a guy who radically changed my business life when he said a seemingly simple thing to me one day in 2017.

Listen in as we discuss success, failure, bottoming out, changing, altering your money mindset and so much more.

For more info, go to www.failyourway.com.

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 million business, their success was far from a straight line—as Lopatin shares in this episode, there were many failures along the way. 

But Spiritual Gangster has never been so much a clothing company as it is an ethos—one that Lopatin embodies. And now he’s helping those who have achieved it all but still find themselves in a place of lack discovering how they can get out of the achievement game and into a life of true fulfillment. 

We dove into everything from the glory failure can bring when you embrace it, how being “energy rich” brings you everything and the way failure comes from fear and attachment. And so much more!

For more info, go to www.failyourway.com.

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 book. I had no idea it would turn into what it has today. And I owe it to him.

To be clear, the dude was no slouch when he first came to me. A prominent sports agent who already represented people like Magic Johnson and Hulk Hogan, he’d had a powerful experience overcoming addiction and wanted to help others in that world. We did his book, Aiming High, with that in mind.

His addiction story is beyond brutal, and it started with a need to escape, in part because of the teasing he got when he was little. (But don’t worry about that; those teasers ended up working for him.)

What Darren has turned his book into blows my mind. It will blow yours too if you listen to this one.

For more info, go to www.failyourway.com.

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 coaching practice, his events, his stand-up specials and everything else he does. 

Listen in on this episode for that system as well as snippets on overcoming his dad leaving when he was born, feeling like a horrible failure on the biggest night of his career, dealing with an ex who’s been brainwashed and so much more. 

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 to Author Alliance.)

Despite the way things may appear, it hasn’t been one clear success after another for Hoehn. He’s even written about the many things he’s tried that have failed!

But there’s one thing he knows how to do better than seemingly anyone, and that’s figuring out what people need—and then delivering it. As he explains it, the last thing busy people want is to figure out who they want to hire. So instead of putting yourself in a sea of many, Hoehn suggests seeing where someone great could do even better—and then do it for them.

We talked about all that and more in this episode. Enjoy!

For more info, go to www.failyourway.com.

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 Soul creator Marc Victor Hansen.

It’s all of that and more.

In this conversation—where he perhaps gives Legacy Launch Pad too much credit in his journey to success—we discuss how to use failure as fuel and how even founders of $100 million companies deal with the same sort of frustrations we all do.

For more info, go to www.failyourway.com.

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 Built and Sold a $25 Million Tech Company Without Being an A**hole, which I’m oh so proud to say that Legacy Launch Pad has published.

In this episode, we talk about her many peaks and valleys, starting with when she only realized she didn’t know what the seventh-grade class secretary did once she was elected to the position through realizing that she had the luxury of failing because of what her family had done for her.

Get all that and more in this episode and you can grab Sharon’s spectacular new book here.

For more info, go to www.failyourway.com.