iwon™ podcast with Michael J Thomas
IWON (It Wasn't Over Night) is a long-form podcast for ambitious founders, featuring honest, in-depth conversations with entrepreneurs, operators, and growth leaders who have built, scaled, or exited tech companies. Hosted by marketing strategist and coach Michael J. Thomas, each episode explores early mistakes, fundraising realities, product decisions, sales lessons, mental health, and resilience. The podcast aims to reveal the real stories behind building successful businesses, from first customers to major exits.
Episodes
This Was for the Founders From Day One - A Sneak Peek into What's Coming
From day one, iwon™ has been for founders. The people thinking about starting, the ones stuck in the messy middle, the founders trying to grow, and even those who have achieved what they thought they wanted and are now asking, “What next?”In this short Season 2 teaser, Mikey looks back at the brilliant guests and lessons from Season 1, from sales, cash flow and product-market fit to AI, purpose, r
Buffer, Dropbox and Superhuman -The Exact Tactics That Drove Rapid Growth - iwon podcast - episode 14
I explain how Buffer, Dropbox, and Superhuman validated their ideas before they scaled. I break down the exact tests they ran so you can apply clear steps to validate your product or feature. I show how Buffer asked for paying signals, how Dropbox used a simple explainer to make the result visible, and how Superhuman focused on the right users and waited for strong commitment. We distill these les
AI + What Every Founder Needs to Know Now | iwon podcast | Episode 13
As you'll know, there is a ridiculous amount happening in tech, software and AI right now.As a founder, it can feel impossible keeping up.That's why Michael J. Thomas sat down to digest it all and share it with you.To save you hours sifting through to find the truth online.TLDR: AI investment and revenue are accelerating, new regulation is taking effect, SaaS pricing is being challenged, and small
AI, Jobs and Power: Musk, Altman and Yang on What Comes Next - iwon podcast - Summer Series with Michael J Thomas
Artificial Intelligence (AI) has fundamentally transformed the landscape of business, provoking critical inquiries regarding its governance and implications.The BIG question is, "Who holds the keys?"As I delve into the recent advancements made by corporate giants such as Microsoft, ServiceNow, SAP, and Capgemini, it becomes evident that substantial financial investments are being made to harness A
Amazon, Meta and Uber + Founders Building with AI | iwon podcast Summer Sessions with Michael J Thomas | Episode 11
AI has made it seem astonishingly easy to build software.But what information should you pay attention to as a founder?As it's summer time, we felt like it would be a good time share some stories from big tech so you can learn from it all. Don't worry - normal guests and episodes will resume after the holidays (some great ones to come).The aim of this episode is to provide you with what you need t
Build the Speedboat: How Small Startups Can Beat Much Bigger Competitors | iwon™ podcast | ep. 10 | Sachin Goyal
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 Multivers
AI Skills and Future of Work - Building a Gold Standard That Doesn't Exist (Yet) | Aatish Thakerar | iwon™ podcast Ep. 9.
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 bigge
The Real Overnight Success Story: Elizabeth Dodson's 14-Year Journey Building HomeZada | iwon™ podcast | Episode 8
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, countless pi
Idea to Impact: From Google to Becoming a Startup Founder - Tolu's Salami's Journey | iwon podcast | Episode 7
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
From IBM to Entrepreneur: Sarah Eggleston's Inspiring Founder Journey | iwon™ podcast episode 6
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.Throughout
Why I’m Taking on Spotify: Scott Truitt’s Plan to Fix a Broken Industry | iwon podcast | Episode 5
Summary of this episodeIn 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 significa
£1M to £5M Revenue: It Could Kill Your SaaS Company | iwon podcast Episode 4 | Mark Blakemore
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
This Blind Spot Ruins Product-Market Fit & Growth | Scott Byrne-Fraser | iwon podcast
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 pr
From Zero to $750 Million: How to Build a High Performing Sales Team | Alex Sullivan Lepaffe | iwon podcast with Michael J Thomas
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.80%
This Will Save You Years in Your Business | Christian Zigler (£24m + Multi-Exit Founder) on VCs, Hiring & AI
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 tec
Welcome to IWON™. Because "It Wasn’t Over Night". It rarely is.
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• The n
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