One of the extraordinary things about the startup ecosystem is the kind of company that gets celebrated. Most of the time, they don’t make money. They bounce from one funding round to the next, and only a tiny % eventually make it. They’re the kinds of businesses that would’ve made our grandparents shake their heads.Today’s guest, Tom Leathes, the Co-Founder and CEO of used car marketplace Motorway, is different. The first few companies he built were bootstrapped, profitable and he sold them for more money. Which is basically how business worked for centuries.But then Tom found himself leading a VC-backed startup and things didn’t go so well. It was the first time he and his Co-Founders had failed. So after that experience they re-set and they’ve come back fighting with another VC-backed business, Motorway, which was just valued at over a billion pounds.Find out about the key learnings that have made him successful - and lead to a different outcome for Motorway.--SponsorsVorboss - get better internet: https://vorboss.com/secretleadersVanta - get 20% off security certifications like ISO27001 and SOC2: https://vanta.com/secretleadersVertice - save on your SaaS or cloud spend ($5k off or a free benchmark) using the code secretleaders: https://www.vertice.one/l/secretleaders--NewsletterSign up here: https://secretleaders.email/You can find our historic newsletters here: https://www.secretleaders.com/episodes Learn more about your ad choices. Visit megaphone.fm/adchoices

If you’re in the UK and you like your peanut butter, you’ve probably come across Pip & Nut, the brand named after its Founder and today’s guest, Pip Murray.Pip started the business when she was 24, at her kitchen table, with a blender and some nuts. But plenty of people start businesses like that so what makes her special? How has she managed it? Oh, and we’ve also got the return of the king, Rich Martell, Co-Founder of Secret Leaders, who went to university with Pip and was one of her early investors. He couldn’t resist the chance to join Dan in the interview chair - and so he could ask Pip the difficult questions.Like how do you actually get your product listed at Tescos? --SponsorsVorboss - get better internet: https://vorboss.com/secretleadersVanta - get 20% off security certifications like ISO27001 and SOC2: https://vanta.com/secretleadersVertice - save on your SaaS or cloud spend ($5k off or a free benchmark) using the code secretleaders: https://www.vertice.one/l/secretleaders--NewsletterSign up here: https://secretleaders.email/You can find our historic newsletters here: https://www.secretleaders.com/episodes Learn more about your ad choices. Visit megaphone.fm/adchoices

It’s amazing how important business seems until something really important happens, like a war breaks out.For Aleksandr Volodarsky, Founder of Lemon.io, which connects companies with software engineers, although he and his colleagues had gotten used to operating in a conflict situation since 2014, he was still stunned when Russia invaded. And the most useful thing he can do now is to keep the business going so it can support the war effort - including his employees who’ve gone off to fight. Find out what it’s like in his shoes right now. What’s going on with his team. What’s it like on the ground.--SponsorsVorboss - get better internet: https://vorboss.com/secretleadersVanta - get 20% off security certifications like ISO27001 and SOC2: https://vanta.com/secretleadersVertice - save on your SaaS or cloud spend ($5k off or a free benchmark) using the code secretleaders: https://www.vertice.one/l/secretleaders--NewsletterSign up here: https://secretleaders.email/You can find our historic newsletters here: https://www.secretleaders.com/episodes Learn more about your ad choices. Visit megaphone.fm/adchoices

Former CEO of MedMen, Adam Bierman, reflects on the rise and fall of the cannabis industry's first unicorn. He discusses the decline of MedMen's value, personal financial losses, leaving the company, and lessons learned from the experience.

What’s particularly shocking about Nick Telson’s success with DesignMyNight is how deliberate it all seemed. They set themselves a target each year, achieved it and moved onto the next one until they’d hit the numbers they needed for the exit they wanted. How many businesses do that? And it was the first startup he’d ever founded…Nick explains how they sold the business - the actual steps they took - which isn’t a process that most people know about unless they’ve been lucky enough to go through an exit themselves. And in classic startup style, it looked like the whole deal was going to collapse on the day of signing until an unlikely hero stepped up.Since exiting DesignMyNight, Nick has founded Horseplay Ventures, and more recently Trumpet, a mixture of Squarespace and Canva and Slack for sales decks. It sounds like something I would use, tbf.Despite his success, throughout his time leading DesignMyNight, Nick kept one aspect of himself relatively hidden - his sexuality. Find out why and what he’s doing about it now. --SponsorsVorboss - get better internet: https://vorboss.com/secretleadersVanta - get 20% off security certifications like ISO27001 and SOC2: https://vanta.com/secretleadersVertice - save on your SaaS or cloud spend ($5k off or a free benchmark) using the code secretleaders: https://www.vertice.one/l/secretleaders--NewsletterSign up here: https://secretleaders.email/You can find our historic newsletters here: https://www.secretleaders.com/episodes Learn more about your ad choices. Visit megaphone.fm/adchoices

It’s the stuff entrepreneurs dream of. Houzz, a marketplace for home renovations, evolved from an evenings and weekends passion project into a multi-billion dollar company with investors queuing up to get a slice of their proverbial pie. So how did the two Co-Founders, husband and wife Adi Tatarko and Alon Cohen, do it?“I think, in retrospect, delaying it and bootstrapping it, the way we bootstrapped it without even understanding that this is what it is back then helped us tremendously down the road.”“Go invest the first six months and validate and see that this idea can really scale, people will really use it, you're really invested in it, and you really love it. And then you will not need to prove these things to investors.”Find out how they secured an investment from legendary investor Mike Moritz in a matter of days - and what they did next to dominate their category.--SponsorsVorboss - get better internet: https://vorboss.com/secretleadersVanta - get 20% off security certifications like ISO27001 and SOC2: https://vanta.com/secretleadersVertice - save on your SaaS or cloud spend ($5k off or a free benchmark) using the code secretleaders: https://www.vertice.one/l/secretleaders--NewsletterSign up here: https://secretleaders.email/You can find our historic newsletters here: https://www.secretleaders.com/episodes Learn more about your ad choices. Visit megaphone.fm/adchoices

Life is the sum of your choices, says Jeffrey Kolovson, COO and Co-Founder of Faire, an online wholesale marketplace for retailers and brands. At the end of the day, it’s not what you say, it's what you do and the choices you make and the accumulation of those over time that matters. “I once had a mentor tell me that the prize for winning the donut eating competition is more donuts. And that kind of stuck with me, as things don't necessarily get easier. And the more you do, the more you have to do.”Jeff isn’t one for taking the easy route. He’s made quite a few interesting choices over the years. Like the time he had to build 60 futons in 36 hours, or the time he left Square to start Faire only to have to leave Faire in its infancy, before returning once more to Faire a few years later. Now, having just raised $400 million in their last funding round off the back of a $12.4 billion valuation, why did Jeff have to leave Faire in the first place? Well, for very good reason - to protect his mental health.“And so you both have to one: figure out how to be at peace with the unrelenting nature of it and two: how you don't let it overwhelm you at any given time. One of the tricks I do is that I like to think about the problems from a year ago or two years ago, how quaint they seem to me now.”The thing is, says Jeff, when you put your head down and work hard, you have to be able to enjoy it. There has to be enough about what you’re doing and the people you’re doing it with, that you derive enjoyment from what you’re doing, otherwise, what’s the point?--SponsorsVorboss - get better internet: https://vorboss.com/secretleadersVanta - get 20% off security certifications like ISO27001 and SOC2: https://vanta.com/secretleadersVertice - save on your SaaS or cloud spend ($5k off or a free benchmark) using the code secretleaders: https://www.vertice.one/l/secretleaders--NewsletterSign up here: https://secretleaders.email/You can find our historic newsletters here: https://www.secretleaders.com/episodes Learn more about your ad choices. Visit megaphone.fm/adchoices

Cocaine, £1,000 on roulette, sleeping with the client, a boss demanding bail out of a Malaysian prison, a restraining order - and that’s just one of the stories in this special episode where we turn the microphone on our host, Dan Murray-Serter.This is the start of a semi-regular series where we interview Dan roughly every three months because:  If you listen to the podcast regularly we thought you might want to get to know him better. Who is this guy in your ears every week? Dan is the Founder of braincare startup Heights so we thought we could grill him every 3 months so you can find out what it’s really like in the Founder hot seat - warts and all. This episode is focused on the early part of Dan’s career - a period when Dan learned how he wanted to lead - from bad bosses.Dan grew up with an entrepreneur of a father - and saw the toll it took on him. It wasn’t a life Dan wanted, so what eventually convinced him to take the plunge into entrepreneurship?“Entrepreneurship is a bit of a drug. And the scariest part of it always is and always has been leaving my job to do this full time, that was always the scariest part, because there's no, you know, there was no safety net.”What was Grabble, Dan’s previous startup? Why did it fail? How did he get invited to Buckingham Palace? Who did he joke about to make the Queen laugh? And why did Brexit kill Grabble?“I mean, the thing is, it is quite a long story, because sadly, what we should have done is pull the cord. And we didn't do that, we did death by 1,000 paper cuts.”--SponsorsVorboss - get better internet: https://vorboss.com/secretleadersVanta - get 20% off security certifications like ISO27001 and SOC2: https://vanta.com/secretleadersVertice - save on your SaaS or cloud spend ($5k off or a free benchmark) using the code secretleaders: https://www.vertice.one/l/secretleaders--NewsletterSign up here: https://secretleaders.email/You can find our historic newsletters here: https://www.secretleaders.com/episodes Learn more about your ad choices. Visit megaphone.fm/adchoices

Having grown up poor, Founder and CEO of Vuori Joe Kudla always wondered what it would be like to have money and go on holiday, so he spent the first chapter of his career proving to himself that he could make money. But then he started to make life decisions differently.“I see myself on my deathbed. And I am coming to terms with that moment, am I going to look back and feel like I went for it, like I seized the day? Did I live a life in alignment with my passions, my heart, my interests? Or did I take the safe path?”In 2013 he founded Vuori, an activewear brand initially aimed at men. They nearly ran out of money in 2015, but a few pivots and several years later Vuori is worth $4b and launching in the UK this spring. How has Joe done it in such a competitive industry? How has he done it having raised a pittance compared to his rivals? And why is clarity the ultimate currency?--SponsorsVorboss - get better internet: https://vorboss.com/secretleadersVanta - get 20% off security certifications like ISO27001 and SOC2: https://vanta.com/secretleadersVertice - save on your SaaS or cloud spend ($5k off or a free benchmark) using the code secretleaders: https://www.vertice.one/l/secretleaders--NewsletterSign up here: https://secretleaders.email/You can find our historic newsletters here: https://www.secretleaders.com/episodes Learn more about your ad choices. Visit megaphone.fm/adchoices

Curve CEO and founder Shachar Bialick is a multi-exit entrepreneur with a background in the Israeli Defense Force special forces.“There's a joke in Israel: how do you win a competition in racing? You start as fast as you can, and you slowly increase the pace.”Curve brings all your credit cards and debit cards into one app and card. The idea first came to Shachar in 2006, but he knew that launching a business is all about timing. And so he waited until 2014 to pick it back up, when he knew the world was ready. After creating a proof of concept in 2015, and raising the first series seed funding of £1.2m in 2015, Shachar launched Curve in 2016.“When we [first] went to MasterCard and told them about what we’re trying to do and the vision we have, we were laughed out of the room, literally they said, ‘Have you opened the MasterCard rules?’”So how did he rack up 4 exits? How big can Curve really be? And why is he using Amazon, Netflix and Spotify to validate his mission?--SponsorsVorboss - get better internet: https://vorboss.com/secretleadersVanta - get 20% off security certifications like ISO27001 and SOC2: https://vanta.com/secretleadersVertice - save on your SaaS or cloud spend ($5k off or a free benchmark) using the code secretleaders: https://www.vertice.one/l/secretleaders--NewsletterSign up here: https://secretleaders.email/You can find our historic newsletters here: https://www.secretleaders.com/episodes Learn more about your ad choices. Visit megaphone.fm/adchoices