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Fail Your Way to Success
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Fail Your Way to Success

Author: Anna David

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The best books are made up of stories.

And the best stories are about bouncing back from failure.

New York Times bestselling author and Legacy Launch Pad Publishing founder Anna David is an expert at both stories and failing your way to success.

Through interviews and solo episodes, she delves into the stories behind the failures and successes of top business leaders, leaving you with the tools you need to turn every failure into a success.

For more about turning your own failure-to-success story into a book, go to
30 Episodes
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
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
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
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
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
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
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 100 million copies of books by people like Brene Brown, Simon Sinek and Jen Sincero.But just because he looks like someone who’s never experienced a day of failure, Anderson is the first to admit that he’s had his fair share—including clients who were incensed when the books his company wrote didn’t sell to traditional publishers.In this episode, we talked about how trying to do everything for your company is asking for failure, the importance of finding people with different strengths than yours and why you have to let go to move on, among other things.For more info, go to
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
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
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
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.For more info, go to
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.For more info, go to
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
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
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
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
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. For more info, go to
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
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 
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