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.

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 MultiFunding, a company that works with entrepreneurs with revenue between one and $20 million on growing their businesses.And yet there have been failures along the way—times where he, metaphorically, struggled to keep the lights on. Still, he looks at entrepreneurship as a triathlon, where you're sometimes going to feel elated and sometimes like you have to vomit.In this episode, he shares about how his biggest failure has been a lack of self-care, why being able to tolerate risk is a key to success and why adapting to circumstances is the key to overcoming failure.For more info, go to www.failyourway.com.

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 venture—and how facing what happened was the key to moving past it.For more info, go to www.failyourway.com.

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 coach but he's also MY business coach. And to say he's brilliant, amazing and hilarious is an understatement. In this episode, we discuss how he recovered from a disastrous first year in college, how the first business he tried to acquire cancelled the deal just as he was dropping off the equity check and how these things taught him exactly how to bounce back.For more info, go to www.failyourway.com.

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 preceded the crime.Now he helps other people find fulfillment before they reach the point he was at. We get into all of that, as well as his three-step process for bouncing back from failure, in this episode.For more info, go to www.failyourway.com.

 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 into how to get paid speaking gigs (the short version: kill it at free conferences so that people ask you to come deliver the same speech at their company) but also how she learned the most from a failed startup, finding out she had to deliver a TEDx talk two days before the event and why she started Innovation Women because she was “pissed off.” For more info, go to www.failyourway.com.

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 failure, why logging your successes and failures at the end of the day transforms your perspective and what it's like to fail every day. For more info, go to www.failyourway.com.

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 to www.failyourway.com.

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 failure around by listening to this episode, here's a fair warning: I talk about me at least half the time. That's because James and I were doing a simul-record—a term I just made up to describe when two people interview each other so they can each release the episode for their individual podcasts.

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 time and space for she and her children to heal. Now she helps people with both wealth building and mental health.In her new book, Buying Time, McNulty walks readers through her journey and shows them not only how they can build wealth but also how they to survive—and thrive—in the worst of times.

Ricky Regalado is an ambitious guy. And when I say ambitious, I mean he runs eight companies in the cleaning business which have an annual revenue in the millions. In this interview, we talked about getting into the 37th college he applied to, how he struggled to make bank loans keep up with his ambition and why starting and ending each day on a positive note is the key to bouncing back from failure. For more info, go to www.failyourway.com.

You surely know by now that I'm obsessed with the idea of failing your way to success. But did you know that I speak at corporations and events on the topic? Well, now you not only know that but you can hear the actual keynote speech in this week's episode. I hope you love it, and that it motivates you to pursue your own EPIC (Extraordinary, Powerful, Impactful and Courageous) goals. And if you want the workbook I mention in the speech to help you along, you can get that here. (Do you work at an organization or with events that bring in keynote speakers and want to bring me in to speak about failing your way to success? Just let me know! And you can get more info about hiring me as a speaker here.)For more info, go to www.failyourway.com.

Justin Breen is without a doubt the most unique person I've ever met (and I've met some unique ones in my time).  He's obsessed with personality tests to the point that he'll have you tell him your Kolbe score before he meets with you. He has no filter. He is the most non-BSy person I've ever known. And he's become, very quickly, a dear friend.  In this episode, he talks about why you need to know where you come from, why he was the most miserable he'd ever been when he was making more money than he'd ever made and why he doesn't believe failure exists, among many other topics. For more info, go to www.failyourway.com.

Ashley Stahl is a force of nature. A former counter terrorism professional turned career coach, bestselling author, spokesperson and podcaster, she's had TEDx talks go viral and she now helps people write and book their own TEDx talks. But she hasn't been without her struggles. In fact, she's gone into debt TWICE on her road to success. And she has all the suggestions and tools anyone can use to bounce back. Lucky for us, she shares them all in this episode.For more info, go to www.failyourway.com.

Let's just get it out up front: I am a Swiftie through and through. We're talking songs-stuck-in-my-head-when-I-can't-sleep, saw-the-concert-documentary-3-times, drove-to-San-Diego-for-a-Taylor-dance-party Swiftie.  And while you may argue with me if you want about the appropriateness of my obsession at my age, you cannot argue with the fact that TS is one of the great entrepreneurs of all time.  Don't believe me? Listen to this and then tell me I'm wrong. 

Mark Fujiwara can trace his first failure back to grade school.But there's no arguing with his success as a financial planner today.Still, as a burgeoning spokesperson for mental health struggles of entrepreneurs, he's as open about failing his way to success as anyone could be.In this episode, we get into breaking generational cycles, holding onto things for 47 years, living up to parents' expectations, talking to your kids about taking medication and so much more.For more info, go to www.failyourway.com.

Oprah is, of course, a legend. Her successes have been well-documented—25 years hosting The Oprah Winfrey Show, an Oscar nomination for The Color Purple and the creation of her OWN network, among many other things. But there have been a few failures along the way, including a box office disaster with Beloved, a bad restaurant investment and even early struggles in her TV career. This episode breaks those down and also includes some amazing Oprah quotes about failure.For more info, go to www.failyourway.com. 

How many people do you know who, while working in banking, thought, "You know, I'd rather be a janitor"?Well, I know one and he's my guest in this episode.John Disselkamp found that suit he had to wear just a bit too tight so left it to literally push a broom.That broom turned into a $10 million a year company with over 300 employees.So how did he do it and what were his failures along the way? More importantly, what constitutes a failure—is it working in a job that doesn't fulfill you or making money? And how can you have both?We got into all that and more in this episode.For more info, go to www.failyourway.com. 

To most people, it looked like Arianna Huffington went from political pundit to publishing with ease, allegedly pocketing a cool $100 million when her eponymous site The Huffington Post sold. But did you know she was rejected 37 times when she was trying to sell her second book? Or that when she ran for governor, she received less than 1% of the votes? In this episode, I break down Huffington's highs, lows, successes and of course failures.For more info, go to www.failyourway.com. 

Michael E. Gerber is well-known for writing his series of E-Myth books.But did you know he lost his whole E-Myth business to his ex-wife?Or that he had numerous struggles before changing the face of business?He's a great guy—I've benefited from that since he wrote the foreword to my most recent book. And in his late 80s, he's still out there failing and succeeding.Listen in as he shares it all.For more info, go to www.failyourway.com. 

When you think of Walt Disney, you may think hit movies and that wondrously hellish theme park. But did you know he came to Hollywood with just a few drawing instruments and $40 in his pocket? Or that he declared bankruptcy in 1920? Or that Disneyland's first day open was called “Black Sunday” because so many things went wrong? I tell you all about that and more in this episode.For more info, go to www.failyourway.com. 

Hal Elrod claims he was mediocre at everything he did as a kid and yet he ended up having his own weekly radio show by the age of 15. Then he became one of the top salespeople at Cutco Cutlery. Then, in 1989 he was struck a drunker drive and broke 11 bones, suffered permanent brain damage, and was found dead. His heart stopped beating for 6 long minutes. Six days later, he woke up from a coma to be told he would probably never walk again. Then, in 2007, he lost everything and used a morning ritual to get his hope back. That ritual turned into The Miracle Morning, which has sold over 2.5 million copies and started a global movement. All good, right? Um, then he was diagnosed with a rare form of leukemia and given a 20-30% chance of surviving. Anyway, he beat cancer, and has gone back to world conquering. So if anyone can talk about failing their way to success, it's this guy. If this episode doesn't inspire you, it's safe to say nothing could. For more info, go to www.failyourway.com. 

You may think you know everything about the failures and comebacks of the late, great Steve Jobs.But I uncovered some new ones in this solo episode.I give them all to you, in quick and bite-sized form. Enjoy the bite out of this apple!For more info, go to www.failyourway.com. 

Laura Spaulding has not had a standard road to success. She went into the military in the early 90s because she was homeless and wanted to go to college. After college, she became a cop in the Midwest. And then, solely because she wanted to earn overtime, she agreed to work undercover pretending to be a sex worker. That led into undercover work busting drug dealers. From there it led to a crime scene clean-up business, then a crime scene cleanup business that also flips the real estate where the crime took place and then a franchise. Have I mentioned the $30 million real estate portfolio or the millions of social media subscribers? Well, it's all in this episode—along with her tips for bouncing back from failure.For more info, go to www.failyourway.com. 

How much have you thought about the origin of that ketchup pack you tried to make sure didn't hit the steering wheel when you enjoyed crispy fries on that road trip? Well, you're going to think about that origin now—particularly the origin of one Henry Heinz, who's responsible for your road trip pleasures. But his journey to leaving a legacy business that has done over 26 billion in revenue was not without its struggles. In fact, his journey includes depression, bankruptcy and a whole lot of other issues along the way. In this solo episode, I break down them all.For more info, go to www.failyourway.com. 

Christina Nicholson worked as a TV producer, reporter and anchor for more than a decade. The founder of Media Maven, a PR agency made up of former journalists. The host of the Become A Media Maven podcast and the founder of Podcast Clout, a podcast database that makes it easier for PR professionals to build podcast pitch lists, she's been on TEDx stages and Lifetime TV, among many other places.She's also a truth teller extraordinaire. And in this episode, she told ALL the truths—about her greatest regrets, her biggest failures, that time she called her boss a sociopath and found herself out of a job and why it's CRUCIAL to share about all your failures.For more info, go to www.failyourway.com. 

Steve Jobs was fired from Apple before returning and making it into the behemoth company it is today. Henry Heinz failed at selling horseradish before he pivoted to ketchup. The point is: many of the most successful people in the world failed before they found success. In this show, New York Times bestselling author Anna David interviews leaders about how they've failed their way to success, leaving listeners with tools to do the same.Find out more information at: www.failyourway.com. 

Steve Jobs was fired from Apple before returning and making it into the behemoth company it is today. Henry Heinz failed at selling horseradish before he pivoted to ketchup. The point is: many of the most successful people in the world failed before they found success. In this show, New York Times bestselling author Anna David interviews leaders about how they've failed their way to success, leaving listeners with tools to do the same.Find out more information at: www.failyourway.com.