iwon™ podcast with Michael J Thomas

Big companies move like oil tankers. Smaller B2B tech companies have an advantage - they can move like speedboats. In this 10th episode of the iwon™ podcast, Michael J. Thomas sits down with Sachin Goyal, Founder and CEO of ClarityLoop, to discuss what it really takes to build enterprise SaaS from the ground up. Sachin has worked in high-growth technology environments, including FanDuel and Multiv...

AI is moving at a rapid pace. Most education institutions, schools and companies cannot keep up with it. While technology continues to reshape industries, careers, and the future of work, many education systems are still trying to figure out how to respond. In this 9th episode of the iwon™ podcast, Michael J. Thomas sits down with Aatish Thakerar, Co-Founder of Pedagogue, to discuss one of the big...

Instagram wasn't an overnight success. Facebook required enormous funding. Most success stories take years. Most people see success and assume it happened quickly. Elizabeth Dodson knows better. What does it take to build a software company for 14 years without giving up? What looks like an overnight success story is actually the result of decades of learning, one successful software exit, countle...

This iwon podcast episode revolves around the entrepreneurial journey of Tolu Salami, the award-winning founder of LetPlant. He's an ex Google and Accenture employee with an innovative solution to plant care, combining software and hardware. This discussion dives into many of the challenges faced by founders and highlights the stark reality that only 1 in 200 entrepreneurs succeed, emphasizing the...

Sarah Eggleston's journey from her two-decade tenure at IBM to the establishment of her own startup encapsulates the multifaceted challenges and triumphs inherent in the entrepreneurial landscape. In our conversation, she articulates the harsh reality that merely building a product does not guarantee its success; potential customers must be aware of its value and relevance to their needs. Througho...

Summary of this episode In this conversation, Scott Truitt shares his journey from a comfortable career in enterprise software to pursuing his passion for music through his start-up, Sawtooth. He discusses the challenges of the music industry, the importance of artist compensation, and the need for a transparent platform that connects artists directly with their fans. Scott emphasizes the signific...

Mark Blakemore, a seasoned financial expert with extensive experience in the SaaS sector, elucidates the critical financial pitfalls that SaaS founders frequently encounter. He introduces the concept of the "SaaS death zone," a precarious stage of growth where companies struggle to secure funding between one and five million in annual recurring revenue. Blakemore emphasizes the importance of maint...

What if the thing slowing growth is not your product team, your marketing, or your users... but a founder blind spot? In this episode of the iwon™ podcast , Michael J Thomas speaks with Scott Byrne-Fraser about the hidden assumptions that cause founders to build the wrong features, chase the wrong outcomes, and lose touch with what customers actually need. Scott shares lessons from his work across...

This podcast episode features a compelling dialogue with Alex, a sales specialist who took one team and company to a $750m exit as sales person number one. He is also an investor, who wants to help founders and their sales people succeed. Believe it or not, the average failure rate of new salespeople is as high as 80 percent. Yet, Alex and his team have a remarkably high 95 percent success rate. 8...

This episode could genuinely save you years in business. Christian Zigler, my guest is a serial entrepreneur who previously founded and exited for around £24m. He has built, scaled, IPO’d and exited multiple companies across Europe. Christian shares hard-earned lessons for founders, start up leaders and tech entrepreneurs who want to avoid the most common early mistakes. Christian is a multi-exit...

Most successful tech companies don’t happen overnight. IWON™ (It Wasn’t Over Night) is a long-form podcast hosted by Michael J. Thomas, featuring honest, in-depth conversations with tech founders, operators and growth leaders who have built, scaled, exited or survived in the world of SaaS. This isn’t surface-level advice or recycled growth hacks. It’s the real story behind: • The early mistakes •...