Stories From the Rock Bottom

Calin Drimbau

Oct 7, 2022

This post is part of our 'Entrepreneurial toolkit' series. In this series, we put together a curated list of resources on a topic that is top of mind for entrepreneurs.

We'll share some key insights from the selected clips, but we highly encourage you to listen to the clips on broadn so that you can hear the experts themselves sharing ideas, opinions, and advice.

Introduction: Stories From the Rock Bottom

We all had our darkest moments. Things sometimes tend to collapse when it's a career setback, a mental health breakdown, or a relationship crisis. In this blog, we have prepared for you some stories from outstanding athletes, entrepreneurs, and creators about their nadirs and what are their reflections on getting back on top from rock bottom. Enjoy. 

Rich Roll on his alcoholic past

To many people, Rich Roll is just a popular podcast host, with The Rich Roll Podcast being a familiar guest on top podcast charts. However, before he rose to the top in the podcast world, he was also an athlete, a wellness advocate, a public speaker, and a lawyer. So it is fair to say that he has lived a versatile life.

This time, on The Tim Ferriss Show, a popular podcast, Rich Roll revealed some of his darkest moments, troubled by his alcoholism. In his twenties, Rich Roll was a student at Stanford Law School, one of the most prestigious law schools in the United States. Yet after attending lectures and seminars in the daytime, Rich was drunk every night, sometimes so unconscious that everything he had on himself was stolen. 

Alcohol addiction finally started encroaching on every part of his life: his academic performances were poor, and he encountered a marital crisis when still on his honeymoon with his wife. 

What helped Rich get out of the situation was becoming an athlete; through training, he forced himself to be more disciplined. When he started to be a bodybuilder and restrained his lousy diet habits, everything negative in his life began to disappear.

Darren Prince on fighting addictions

Darren Prince is a celebrity agent and CEO of Prince Marketing Group. Despite the success he owns today, Darren had a pretty low period in his life, fighting addictions.

On the podcast On Purpose with Jay Shetty, Darren told his story that there was a lengthened period in his life where his mind was entirely under the control of pills. He couldn't go anywhere without them and stored various medications in his house.

What helped Darren escape his predicament was a combination of professional help and his new dedication to assisting others in getting rid of addiction. Mentored by a group of professionals, his rehab had a good start, and his self-redemption through helping other addicted people boosted his confidence. In reflection, Darren regarded helping others as the most significant contributor to his recovery: there is nothing better than assisting others and watching them lead better lives.

Tom Blomfield on dealing with a PR crisis

Building a Fintech firm is difficult, especially when your firm's name is Monzo. Monzo was once deeply troubled by scandals around Anti-money laundering procedures and payment security questions as one of the biggest names in UK digital banking. 

At the height of the digital banking scandals, every day, every newspaper in the UK will put Monzo on the front page, said Tom Blomfield, ex-CEO of Monzo, on the critically acclaimed podcast The Story of a CEO with Steven Bartlett. 

The business model of Monzo was flawed, and Tom Blomfield knew that, but he was so deeply rooted in this fast-growing business machine that he could not break from it and start a significant refresh. So, finally, he decided to leave Monzo at the start of 2021 to chase a more balanced and calm life.

James Lawrence on his difficult journey out of the financial crisis

James Lawrence, also aptly named the 'Iron Cowboy' from his biography, is a Canadian athlete. He initially rose to fame in 2015 when he set the world record for the most Ironman-distance triathlons completed within a calendar year: 50. James broke that record in 2021 during the 'Conquer 100' in which he completed 100 consecutive Ironman length triathlons in 100 days. He then completed one more for a total of 101 in 101 straight days. He also holds the record for the most half-ironman distance triathlons in one year: 22.

Nonetheless, being an iron-man athlete as he is, James Lawrence had fallen to the bottom. When he initially moved to the United States, he, unfortunately, ran into the Global Financial Crisis of 2008 and lost almost all his possessions. He had to live with his family in abject houses and endured a period of poverty. 

After a few years, James was able to find a new life by being an athlete. He had trained a tough mindset through the difficulties, which is well-suited for competing in sports. His biography became a bestseller, and now he tells this story on one of the most popular podcasts on the whole Internet: Impact Theory with Tom Bilyeu.

Dan Murray-Serter talks about the failure of his former startup

Dan Murray-Serter, a multi-time successful founder and LinkedIn influencer, spoke about the darkest moments on his podcast, Secret Leaders. His previous startup, Grabble, was highly successful at its start and was a multi-award-winning fashion app for web and mobile, which helps users browse, save and purchase the latest fashion in one place. The outstanding growth Grabble achieved attracted many early-stage investors looking to tap Grabble's potential.

While everything was running smoothly, a storm was forming in the background; on the day the UK government announced that the country will start Brexit, all investors suddenly started calling to pull their investments out. They don't want to risk their money during fluctuations and chaos. Cut off from fresh capital, Grabble lost the ground it stood upon and failed briefly after.

Dan didn't stop here. He summarized his learnings from his entrepreneurial experiences: he knows how to build a good business model and make a product that people love. He just needed more time. After the pandemic, his new startup Heights finally rose as a famous brain-health brand and attracted £1.7 Million in funding.

Joe Rogan on his experience through horrible controversies

If you are a podcast lover, you probably already know who Joe Rogan is. Previously a UFC color commentator, he now runs one of the most popular podcasts on the planet: The Joe Rogan Experience. 

With his popularity also came controversies. Earlier this year, Joe Rogan was attacked by various media after he made some inappropriate jokes. Those days he was constantly insulted on social media and on national television. As he described on the Lex Fridman Podcast, his family started worrying about his mental health during that period.

But Joe Rogan stayed strong and kept on producing his media programs, and currently, his podcast is still high on any podcast player's list. When asked how he managed to pull that through, he said the right attitude to deal with these situations is to focus on doing the right things. So, with his career goals in mind, Joe Rogan continued producing high-quality podcast episodes and will probably continue to do this for a while.

Bill Ackman on the lessons learned from investment losses

Bill Ackman is a superstar in the investor community. His activist investment approach and his fund Pershing Square Capital's great returns make him one of the most exciting financial figures. 

As a seasoned investor, Bill Ackman had his downturns, especially in 2012 when he started campaigning and shorting against a company called Herbalife, calling it a pyramid scheme. On The Knowledge Project podcast, he recollected that, while Herbalife ran a suspicious business model, Bill Ackman was targeted by another famous investor, Carl Icahn, and suffered short squeezes. Finally, Bill Ackman had no option but to choose to cover all his short positions, incurring a loss of hundreds of millions of dollars. 

Bill Ackman said he didn't let this failure hit him. Instead, he felt motivated because he thought the attacks he incurred proved his opinions right. As a result, he continued to seek investment opportunities, and his Pershing Square Capital is still delivering outstanding performance.

David Goggins on taking the first step

David Goggins, the American ultramarathon runner and retired United States Navy SEAL, is currently very popular on various social media channels for his inspirational content. But do you know that he was once troubled by obesity and domestic violence?

When David was on the Impact Theory with Tom Bilyeu podcast, he mentioned his childhood scarred by his father's beatings and racist taunts from his neighbors. Before qualifying for SEAL training, he was also too obese that people would laugh at his body. Compared to his unusual stamina and fit shape, David Goggins was in real trouble back then.

He told the podcast listeners to dare to take the first step because it is always the hardest. For example, when David applied to become a SEAL, he was overweight and had to lose 100 pounds in 3 months to have a chance. While it seemed impossible, David took that first step, opening the door for him to many years of physical fitness and superman-like mental strength.


It is always inspiring to hear people rising back on top after being trapped in difficulties. What's more important, though, is to summarize these learnings and apply them to real-world problems.  We hope the resources compiled above are helpful to get you started on getting your startup on track for product-market fit. To listen to the clips and the full episodes, sign up to get access to broadn.