iwon™ podcast with Michael J Thomas

Michael J Thomas

IWON™ (It Wasn’t Over Night) is a long-form podcast for ambitious founders. Wherever you are at in your business journey, you'll get something from every episode and each guest. These are the people who been there and done it. If you want to understand what it actually takes to build and scale a successful company, iwon™ is worth listening to. Each episode features honest, in-depth conversations with founders, operators and growth leaders who have built, scaled, exited or survived in the tech world. Iwon™ is hosted by Michael J. Thomas. He is an experienced marketing strategist, Cambridge-accredited coach and founded DARWIN™ Works Marketing in 2011. This isn’t surface-level advice or recycled LinkedIn BS. It's the real stories. We go deep and unscripted with every episode and every guest. It’s the real story behind: • Early mistakes and failures • Fundraising realities and financial pressure • Product and growth decisions that changed everything • Sales lessons that cost years to learn • Mental health, leadership and resilience • What genuinely moves the needle From first customers to $750m exits, IWON reveals the thinking, trade-offs and hard-earned lessons you rarely hear in public. If you are building a SaaS or tech company, leading a product or growth team, or trying to grow without chaos, this podcast will give you perspective, clarity and practical insight from people who have done it for real. New episodes every two weeks. The names iwon and DARWIN are registered trademarks. This podcast and the opinion-based content herein are wholly owned by, property of, and produced by - and is a DARWIN Works Production - a trading name of BlueEyed Digital Marketing Ltd. Copyright 2026.

  1. Oct 15

    Two Unlikely Founders With One Big, Bold Vision for the Future | iwon™ podcast | Season 2 Episode 1

    These two co-founders and their story will inspire you to dream bigger. It all starts with one question ... Where do you find the perfect technical co-founder? LinkedIn? A startup accelerator? Y Combinator? For Tracey Aitken and David Carboni, the answer was slightly less conventional: Tinder. Tracey spent around 30 years in hairdressing and salon ownership. David spent his career in technology, engineering and working as a CTO. Two completely different worlds. Partners in life. Partners in business. And now co-founders of HairTracker. In the first episode of Season 2 of iwon™, we talk about how a problem Tracey had lived with for decades became the foundation for a technology company, and why sometimes your biggest advantage as a founder is knowing an industry from the inside. But their first idea wasn't HairTracker. There was Capture Me. Then the wonderfully named Ping My House. Neither became the business. But neither was a failure either. Those early experiments helped Tracey and David learn how to build together, understand each other's strengths and eventually recognise the opportunity that had been sitting right in front of them. We get into: • How to know when to persevere and when to pivot • Why founder fit matters as much as product-market fit • Building a business with your life partner without destroying the relationship • Why Tracey's 30 years of hairdressing experience became an enormous competitive advantage • What happens when a non-technical founder meets a “firewall” for the first time • Building the first version of HairTracker around a genuine problem Tracey experienced herself • Validating the product with working hairdressers and the wider industry • Winning support from Innovate UK • Why being new to an industry can sometimes work in your favour • Building confidence when you don't feel like you know what you're doing • Networking when you're completely outside your comfort zone • Why Tracey doesn't believe in failure • And why their philosophy is simple: take action, learn, adjust and keep moving One of my favourite ideas from the conversation is also one of the simplest: The language of the universe is action. You don't need to know exactly how everything is going to work before you start. Sometimes you take the next step, see what happens, learn something and take another. As Tracey puts it: If you don't take action, nothing happens. If you're building something, thinking about starting something, looking for a co-founder, or wondering whether your own experience is “relevant enough” to build a company around, this episode is absolutely worth your time. ABOUT HAIRTRACKERHairTracker is being built around a problem Tracey experienced first-hand throughout her career in hairdressing: keeping useful, accessible and practical client records. What began as a product built for Tracey's own needs has evolved through feedback from hairdressers and the wider industry, with Tracey and David exploring opportunities across hair, beauty and education. ABOUT IWON™iwon™ stands for It Wasn't Overnight. Most business podcasts make success sound much cleaner and faster than it really is. This show is about what happens in the middle. The false starts. The uncomfortable decisions. The sacrifices. The mistakes. The pivots. The lessons. And all the work nobody sees before somebody eventually calls it an “overnight success”. If you're a founder, building something of your own, or even just thinking about it, subscribe wherever you get your podcasts. DISCOVER HAIRTRACKER Website: https://hairtracker.com/ Apple App Store: https://apps.apple.com/gb/app/hairtracker/id6475737879 Google Play: https://play.google.com/store/apps/details?id=app.hairtracker HairTracker Education: https://hairtracker.com/education LinkedIn: https://www.linkedin.com/company/hairtracker/ CONNECT WITH TRACEY AND DAVID Tracey Aitken: https://www.linkedin.com/in/tracey-aitken/ David Carboni: https://www.linkedin.com/in/davidcarboni/ CONNECT WITH MICHAEL LinkedIn: https://www.linkedin.com/in/realmjt-in/ DARWIN™: https://darwinworks.com/ iwon™: https://iwonpodcast.com/ Apply to be a guest: https://iwonpodcast.com/ Subscribe or watch now - on YouTube: https://www.youtube.com/@realmjt ABOUT IWON™ Most business stories show you the funding, growth or success. iwon™ explores the false starts, uncomfortable decisions, sacrifices and lessons that came first. If this conversation helped you, subscribe, like the video and tell us in the comments: would you build a company with your life partner? DISCLAIMERThe views expressed in the iwon™ podcast are those of the individual speakers and do not necessarily reflect the views of the producers or associated organisations. This podcast is provided for informational and entertainment purposes only and should not be considered financial, legal, investment or other professional advice. Always conduct your own research and seek appropriately qualified professional advice before making decisions for yourself or your business. The iwon™ Podcast is produced by DARWIN™ Works, a trading name of BlueEyed Digital Marketing Ltd. iwon™ and DARWIN™ are registered trademarks. © BlueEyed Digital Marketing Ltd 2026. Companies mentioned in this episode: TinderLinkedInY CombinatorHair TrackerCapture MePing My HouseZooplaEtsyBeauty TrackerInnovate UKApple App StoreFacebookInstagramChatGPT

    Two Unlikely Founders With One Big, Bold Vision for the Future | iwon™ podcast | Season 2 Episode 1

  2. Oct 1

    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, resilience and the reality behind so-called overnight success. And, more importantly... Season 2 is coming. More founders. More mistakes. More lessons. More honest conversations about what it actually takes to build something. What We Have Accomplished Already (Don't Miss This Either)Season 1 of iwon™ brought together founders, operators and business leaders at very different stages of the journey. In this episode, Mikey looks back at some of the biggest lessons from: Sarah Eggleston Leaving the 9-to-5, starting before you're ready and building something of your own. Tolu Salami Leaving Google and Accenture, validating an idea and talking to customers before disappearing off to build. Scott Byrne-Fraser How to work out whether you're actually solving the right problem for your customers. Alex Sullivan-Lepaffe Why hiring a salesperson isn't a magic answer to your growth problems. Mark Blakemore Cash runway, financial discipline and surviving the dangerous growth “death zone”. Scott Truitt Purpose, fulfilment and what happens when conventional success still leaves you asking, “Is this it?” Elizabeth Dodson Fourteen years building HomeZada and the truth behind the phrase “overnight success”. Aatish Thakerar AI, leadership, resilience and the things technology still can't replace. Sachin Goyal Why he spent 10 months building alongside one customer before charging them a penny. Christian Zigler Building, scaling and exiting businesses, raising money, working with companies including Netflix and PayPal, and the lessons founders normally learn the hard way. Different founders. Different businesses. Different stages. That was always the point. This was for the founders from day one. Season 1 has already reached more than 85,000 people across YouTube, LinkedIn and other platforms, with updated numbers still to come. And now we're getting ready to go again. SEASON 2 IS COMINGMore founders. More brilliant stories. More mistakes. More lessons. And more of the bits of building a business that usually get edited out of the success story. If you've listened, watched, shared an episode, left a review or sent Mikey a message during Season 1, thank you. We're just getting started. WATCH & FOLLOW IWON™YouTube: https://www.youtube.com/@realmjt Apple Podcasts: https://podcasts.apple.com/gb/podcast/iwon-podcast-with-michael-j-thomas/id1882021798 Spotify: https://open.spotify.com/show/629GCCMNKOJNblEtz99Ybp Website: https://iwonpodcast.com/ ABOUT IWON™iwon™ stands for It Wasn't Overnight. Most business podcasts focus on the success at the end. We're interested in everything that happened in between. The mistakes. The pivots. The doubts. The decisions that worked. The ones that didn't. And the lessons founders usually have to learn the expensive way. No hype. No overnight-success rubbish. Just honest conversations about what it actually takes to build something. DISCLAIMERThe views expressed in the iwon™ podcast are those of the individual speakers and do not necessarily reflect the views of the producers or associated organisations. This podcast is provided for informational and entertainment purposes only and should not be considered financial, legal, investment or other professional advice. Always conduct your own research and seek appropriately qualified professional advice before making decisions for yourself or your business. The iwon™ Podcast is produced by DARWIN™ Works, a trading name of BlueEyed Digital Marketing Ltd. iwon™ and DARWIN™ are registered trademarks. © BlueEyed Digital Marketing Ltd 2026.

    This Was for the Founders From Day One - A Sneak Peek into What's Coming

  3. Sep 17

    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 lessons into a three step plan to test the problem, the promise, and the path quickly. I provide a worksheet and a practical playbook to help founders run small tests that give clear signals before building more features. Takeaways: I showed that you must test whether people will move toward paying before building full features.I demonstrated how Dropbox used a short explainer video and a landing page to make the outcome visible and easy to understand.I argued that Superhuman succeeded by focusing on one clear problem, finding the right users, and refusing to scale prematurely.We recommended designing the smallest test that can give a clear signal in a week or ten days before adding more work.I urged founders to decide whether to test the problem, the promise, or the path first and to use simple commitment signals like clicks, waitlists, or pilot requests rather than building unvalidated features. Companies mentioned in this episode: BufferDropboxSuperhumanTwitterXFacebookLinkedInPinterestInstagramGoogleGoogle DriveGeminiChatGPTClaude Enjoyed This Episode?If you found this conversation valuable, follow the show so you don’t miss future episodes with founders and growth leaders building in SaaS and tech. Leaving a 5-star review on Apple Podcasts or Spotify helps more aspiring entrepreneurs and founders in the trenches right now to discover the show. And, it supports the growth of the IWON™ community. About the HostMichael J. Thomas is a marketing strategist and Cambridge-accredited coach. He founded DARWIN™ Works Marketing in 2011, helping SaaS and tech companies overcome growth hurdles and build sustainable momentum. Learn more about Michael and DARWIN™ here: https://darwinworks.com About IWON™IWON™ (It Wasn’t Over Night) is a long-form podcast exploring what it really takes to build and scale a successful technology company. Find out more about the podcast: https://iwonpodcast.comInterested in being a guest? https://iwonpodcast.com/guests/Want to sponsor IWON™ and help the community thrive? https://iwonpodcast.com/sponsors/ Michael J Thomas Copyright 2026 - iwon and DARWIN are registered trademarks. This podcast and those trademarks are wholly owned by, property of, and produced by - and is a DARWIN Works Production - a trading name of BlueEyed Digital Marketing Ltd.

    Buffer, Dropbox and Superhuman -The Exact Tactics That Drove Rapid Growth - iwon podcast - episode 14

  4. Sep 3

    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 companies are still finding ways to attack enormous incumbents. Michael digests the stories, goes back to the original sources and asks the question founders actually care about: so what does this mean for my business? Full show notesAI is booming. Anthropic is reportedly generating revenue at an extraordinary rate. The European Central Bank is asking whether AI valuations are beginning to resemble the dot-com era. The EU AI Act has new transparency obligations in force. The UK is examining its reliance on American frontier AI models. And a $21B chip startup founded by three people in their mid-twenties is taking on Nvidia. Those are the headlines. This episode is about the useful bit: what they mean for founders and CEOs. Michael breaks down the news in plain English, then tests some of the startup advice founders hear constantly and finishes with practical questions that come up in his consulting work and conversations with founders. The core promise is simple: reliable sources, no BS, the TLDR, Michael’s take, and why it matters to you. TOPICS COVERED • AI boom versus AI bubble • Anthropic’s reported $65B annual revenue run rate and what it does — and does not — prove • Why AI hype is not the same as product-market fit or a business model • Why the EU AI Act can still matter outside the EU • AI transparency, enterprise buyers and trust • The strategic risk of relying on one AI provider • Model agnosticism and having a backup plan • How AI could change SaaS seat pricing, usage pricing and margins • Etched versus Nvidia and what underdogs can learn from changing markets • Fact or Fiction: raising with an MVP, solving your own problem, founder audiences, niche SaaS and pre-selling • Founder Hot Seat: sales leadership, crowded markets, technical founders selling, and marketing versus sales iwon™ stands for It Wasn’t Overnight. Michael created the show to get beyond polished success stories and understand what really happens between the beginning and the apparent success at the end. iwon™ conversations mentionedSachin Goyal — ClarityLoop: https://youtu.be/FJqy1H3UBIY?si=vcwoZydODSNdstBn Beth Dodson — HomeZada: https://youtu.be/NbJUs4Ib3EE?si=Y8e2gbYwpKthaKv0 Aatish Thakerar — Pedagogue: https://youtu.be/tAS-ndpYk7Q?si=g32R0ChpifQZ0ORg Alex Sullivan-Lepaffe — The Salespeople: https://youtu.be/q7gbrmvsius?si=d_suyY-_-UfzV7xS Mark Blakemore — Home Run Finance: https://youtu.be/iU6ONslsshw?si=vzQgqaf47Dnc9Lnr Original sources and further readingEuropean Central Bank — The AI boom: rational enthusiasm or the next dot-com bubble?: https://www.ecb.europa.eu/press/blog/date/2026/html/ecb.blog20260817~754a8a4418.en.html Reuters — Anthropic IPO valuation hinges on $190–200bn 2028 revenue forecast: https://www.reuters.com/business/anthropic-ipo-valuation-hinges-190-200-billion-2028-revenue-forecast-sources-say-2026-08-15/ Reuters — Anthropic revenue run rate tops $65bn: https://www.reuters.com/technology/anthropic-revenue-run-rate-tops-65-billion-source-says-2026-08-17/ European Commission — Article 50 transparency guidelines: https://digital-strategy.ec.europa.eu/en/library/guidelines-transparency-obligations-providers-and-deployers-ai-systems European Commission — Article 50 FAQ: https://digital-strategy.ec.europa.eu/en/faqs/transparency-obligations-under-article-50-ai-act Financial Times — UK examines economic hit from loss of access to frontier AI models: https://www.ft.com/content/418e0159-d2d1-4432-a7b3-de0cc446ef08 McKinsey — Upgrading software business models to thrive in the AI era: https://www.mckinsey.com/industries/technology-media-and-telecommunications/our-insights/upgrading-software-business-models-to-thrive-in-the-ai-era McKinsey — Is that AI agent worth it? Agentic economics and the modern operating model: https://www.mckinsey.com/capabilities/quantumblack/our-insights/is-that-ai-agent-worth-it-agentic-economics-and-the-modern-operating-model Wall Street Journal — A $21 Billion 'Kids in Chips' Startup Is Scooping Up Nvidia Talent: https://www.wsj.com/tech/ai/a-21-billion-kids-in-chips-startup-is-scooping-up-nvidia-talent-4d099f12 Carta — State of Pre-Seed, Q2 2026: https://carta.com/uk/en/data/state-of-pre-seed-q2-2026/ CRV — Series A Metrics VCs Expect in 2026: https://www.crv.com/content/series-a-metrics-vcs-expect First Round Review — Productboard’s Path to Product-Market Fit: https://review.firstround.com/productboards-path-to-product-market-fit/ LinkedIn + Edelman — How B2B Thought Leadership Can Persuade Hidden Buyers: https://www.linkedin.com/business/marketing/blog/research-and-insights/b2b-thought-leadership-influence-hidden-buyers SaaStr — Vertical SaaS and high net retention with Mangomint: https://www.saastr.com/vertical-saas-and-high-net-retention-revenue-with-mangomint/ First Round Review — Material Security’s Path to Product-Market Fit: https://review.firstround.com/material-securitys-path-to-product-market-fit/ Connect with Michael / iwon™ / DARWIN™Michael J. Thomas on LinkedIn: https://www.linkedin.com/in/realmjt-in/ DARWIN™ Works: https://darwinworks.com/ iwon™ podcast: https://iwonpodcast.com/ Apply to be an iwon™ guest: https://iwonpodcast.com/guests/ YouTube @realmjt: https://www.youtube.com/@realmjt DisclaimerThis episode contains news commentary, research summaries and personal opinion. The opinions and...

    AI + What Every Founder Needs to Know Now | iwon podcast | Episode 13

  5. Aug 6

    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 AI's potential for tangible business outcomes. Simultaneously, influential figures like Elon Musk, Sam Altman, and Andrew Yang have different perspectives on the future trajectory of AI, prompting us to reflect on the broader societal implications of these technologies. This discourse aims to engage listeners in contemplating the profound questions surrounding AI's role in our lives, rather than prescribing definitive conclusions. This week’s episode brings to the forefront the intricate relationship between technological advancement and societal impact, particularly in the realm of AI. As businesses rush to integrate AI into their operations, the conversation extends beyond technological capabilities to encompass ethical and economic ramifications. The insights from thought leaders like Musk, Altman, and Yang provoke a deeper investigation into the balance of power in an increasingly automated world. Musk's vision of a future where work becomes optional contrasts sharply with the practical realities faced by employees today, raising essential questions about income distribution and the role of government in this transition. Recent high profile security breaches involving AI systems, the need for vigilant oversight in the deployment of AI technologies cannot be overstated. Let's explore it all together. Takeaways: Artificial Intelligence has the potential to transform product development and customer service significantly, yet it prompts critical inquiries regarding control and oversight.The financial investments by corporations such as Microsoft, ServiceNow, and SAP reveal a robust commitment to integrating AI into existing operational frameworks, marking a shift towards practical applications.Elon Musk, Sam Altman, and Andrew Yang present different perspectives on the implications of AI, urging us to consider both opportunities and ethical challenges as we advance.The recent incident involving an autonomous AI agent underscores the necessity for stringent controls and ethical guidelines in the deployment of advanced technologies.As businesses increasingly leverage AI, the focus must not solely be on technological capabilities but also on the broader socioeconomic effects that may arise, particularly regarding employment.The ongoing discourse surrounding AI necessitates a collective examination of power dynamics, ownership, and the responsibilities of technology creators to society at large. Companies mentioned in this episode: MicrosoftUnileverNovo NordiskServiceNowSAPCapgeminiOpenAIHugging FaceModal LabsDremioPrior LabsElon MuskSam AltmanAndrew YangMartin Ford Reports, interviews and sources mentioned:Elon Musk interviewed by The EconomistSam Altman on AI and the “jobs apocalypse”Andrew Yang and Martin Ford, “The Robots Are Coming for Your Job”.Microsoft launches Microsoft Frontier CompanyServiceNow Q2 2026 results and highlightsSAP trims its 2026 profit outlookCapgemini raises its growth target as businesses prepare for AIOpenAI agent security incidentHugging Face security incident disclosureCloudflare on the changing scope of internet usage This podcast represents personal commentary and opinion based on publicly available reporting and sources. It is intended to encourage open discussion, not to provide financial, legal, investment or technology advice. Opinion and freedom of expression are protected under the law. Please review the original sources and make up your own mind. Enjoyed This Episode?If you found this conversation valuable, follow the show so you don’t miss future episodes with founders and growth leaders building in SaaS and tech. Leaving a 5-star review on Apple Podcasts or Spotify helps more aspiring entrepreneurs and founders in the trenches right now to discover the show. And, it supports the growth of the IWON™ community. About the HostMichael J. Thomas is a marketing strategist and Cambridge-accredited coach. He founded DARWIN™ Works Marketing in 2011, helping SaaS and tech companies overcome growth hurdles and build sustainable momentum. Learn more about Michael and DARWIN™ here: https://darwinworks.com About IWON™IWON™ (It Wasn’t Over Night) is a long-form podcast exploring what it really takes to build and scale a successful technology company. Find out more about the podcast: https://iwonpodcast.comInterested in being a guest? https://iwonpodcast.com/guests/Want to sponsor IWON™ and help the community thrive? https://iwonpodcast.com/sponsors/ Michael J Thomas Copyright 2026 - iwon and DARWIN are registered trademarks. This podcast and those trademarks are wholly owned by, property of, and produced by - and is a DARWIN Works Production - a trading name of BlueEyed Digital Marketing Ltd.

    AI, Jobs and Power: Musk, Altman and Yang on What Comes Next - iwon podcast - Summer Series with Michael J Thomas

  6. Jul 23

    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 to know as a founder. So that you apply some of those lessons to how you plan to use AI to improve your business. Here's the TLDR version for you: A founder recently showed Michael a product he had created using AI in just nine days. It worked. It looked good. But what would happen when a paying customer encountered a problem nobody had anticipated? How would they even know where to begin? That is where a promising demonstration has to become a dependable product. In this first iwon™ Summer Session, Michael J. Thomas explores with you, what Amazon, Uber, Meta and Humata Health shared on AI. The goal is to share useful lessons for founders and AI. Amazon’s experience raises important questions. Uber’s spending demonstrates why producing more code does not necessarily create more customer value. Meta’s enormous infrastructure investment shows that even the largest technology companies must find sustainable business models in the AI era. Humata Health explains why the difficult “final mile” of security, compliance, integration and support still matters. AI has made building easier. Responsibility has not changed. So put your feet up, enjoy the summer and let Michael gently narrate what is happening in AI. Think Bob Ross (how Michael sounds, according to his friend), but with fewer happy little trees and considerably more enterprise software. In this episodeWhy a working AI prototype is not necessarily a dependable productThe difference between vibe coding and responsibly assisted developmentWhat Amazon’s experience with its Kiro coding agent can teach foundersWhy human review and accountability still matterHow Uber reportedly exhausted its annual AI coding budget in four monthsWhy producing more code does not automatically create more customer valueMeta’s projected investment of up to $145 billion in 2026Why Meta is exploring ways to commercialise its AI infrastructureHumata Health’s warning about the difficult “final mile”How AI is changing the build-versus-buy decisionWhy security, compliance, reliability and support can become a competitive moatThree questions every founder building with AI should answer Timestamps00:00 Welcome to the iwon™ Summer Sessions 01:09 The AI product built in only nine days 01:45 A demonstration is not a dependable product 03:47 What Amazon can teach founders about AI-assisted development 04:43 Kiro and the reported AWS service interruption 05:17 Amazon’s response and the return of mandatory peer review 06:25 Why more code does not automatically mean more value 06:42 Uber’s AI spending and the customer-value question 08:01 Meta’s investment of up to $145 billion 08:29 Could Meta turn its infrastructure into another business? 10:02 Humata Health and the difficult final mile 11:57 How AI is changing the build-versus-buy decision 13:03 Why Gartner expects many agentic AI projects to be cancelled 13:42 Trust as a competitive advantage 14:04 The questions enterprise buyers will increasingly ask 15:07 Three questions for founders building with AI 16:01 Building is becoming easier, but responsibility is not 16:43 Final thoughts from Michael Three questions for foundersWhat would happen if a customer stress-tested your product tomorrow?Are the depth, reliability and value of your product clear to prospective buyers?Are you creating enough genuine value to make customers want to stay when a competitor can build something similar? Sources and further readingMichael J. Thomas: “Building AI is easy. But is there a business around it?”Computing UK: AWS blames user error, not AI, for cloud outage caused by AIFinancial Times: Amazon service was taken down by AI coding botThe Guardian: Amazon’s cloud reportedly hit by outages involving AI toolsBusiness Insider: Uber COO says AI spending is becoming harder to justifyReuters: Meta raises its 2026 capital expenditure forecast to as much as $145 billionReuters: Meta building a cloud business to sell excess AI capacityReuters: Meta and Anthropic discuss a potential $10 billion compute agreementForbes: Dr Jeremy Friese on how the build-versus-buy decision has changedGartner: Over 40% of agentic AI projects predicted to be cancelled by the end of 2027 Follow Michael and iwon™Michael J. Thomas: https://www.linkedin.com/in/realmjt-in/ iwon™ podcast: https://iwonpodcast.com/ YouTube: https://www.youtube.com/@realmjt Apple Podcasts: https://podcasts.apple.com/gb/podcast/iwon-podcast-with-michael-j-thomas/id1882021798 Spotify: https://open.spotify.com/show/629GCCMNKOJNblEtz99Ybp DARWIN™: https://darwinworks.com/ If you enjoyed the episode, please follow the podcast and leave a five-star review. It helps more founders discover these conversations. DisclaimerThis episode summarises research, personal opinions and interpretation of publicly available information and reporting. It is provided for discussion, information and freedom of expression only. For openness and transparency, all articles and sources have been provided. It should not be treated as professional, legal, financial, technical, cybersecurity or business advice. Sources are provided above so listeners can review the original reporting and reach their own conclusions. Some of the organisations mentioned have disputed aspects of the reporting, as acknowledged during the episode. We aim to provide a fair and balanced view on the information provided. Always conduct your own research and seek appropriately qualified professional advice before making decisions for your business. The names iwon and DARWIN are registered trademarks. A DARWIN Works Production. Copyright 2026. Takeaways: The advent of AI has drastically transformed the speed at which founders can create initial product versions, enabling rapid prototyping in mere days.While rapid prototyping is beneficial, it is imperative for founders to understand the complexities involved in building a product that is robust and reliable.Customers are not merely interested in polished demonstrations; they demand comprehensive support and dependable performance post-purchase.The necessity for thorough security and compliance measures becomes paramount, especially in industries handling sensitive information such as healthcare. Companies mentioned in this episode: AmazonUberMetaHumata HealthLoveableBase44

    Amazon, Meta and Uber + Founders Building with AI | iwon podcast Summer Sessions with Michael J Thomas | Episode 11

  7. Jul 9

    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 Multiverse, where he helped scale teams and navigate the realities of fast-moving software businesses. But when he started ClarityLoop, he chose a very different path. Instead of raising too early, chasing pitch decks, or blindly following the standard startup playbook, Sachin focused on solving a real problem for a real customer. ClarityLoop helps teams develop performance continuously by using AI to analyse work patterns, surface useful signals, and support better feedback, coaching, performance conversations, and career growth. But this episode is not just about AI, HR, or performance reviews. It is about how enterprise software is really built. Together, Michael and Sachin explore why traditional performance review processes are outdated, why generic startup advice does not always apply to enterprise B2B founders, and why one committed customer can sometimes matter more than thousands of casual users. Sachin also shares the honest lessons he learnt from bootstrapping ClarityLoop, spending months building alongside a major enterprise customer, avoiding early fundraising, and learning why founders need real commitment from customers, not just polite enthusiasm. If you are a SaaS founder, B2B tech founder, technical founder, enterprise software builder, or someone trying to work out whether your idea is actually worth pursuing, this conversation is packed with practical, honest, and deeply useful insight. In This Episode • Why Sachin walked away from hypergrowth to bootstrap ClarityLoop • How ClarityLoop helps teams develop performance continuously • Why feedback should happen inside the work, not months later • Why customer discovery matters more than the idea • What The Mom Test taught Sachin about asking better questions • Why enterprise B2B is completely different from B2C startup advice • Why MVP advice does not always work in enterprise software • The dangers of raising money too early • How small B2B tech companies can beat large incumbents • Why great enterprise SaaS is built through trust and relationships • What Sachin would do differently if he started again • Why managers need better signals, not more dashboards • How AI can help managers prepare for difficult conversations. Connect with Sachin Goyal LinkedIn: https://www.linkedin.com/in/sachin-goyal-se/ ClarityLoop: https://www.clarityloop.com/ Connect with Michael J. Thomas LinkedIn: https://www.linkedin.com/in/mrmichaelthomas/ Stuck where you are with your SaaS or B2B tech product? Michael and the team at DARWIN™ Works help founders simplify their message, sharpen their positioning, and accelerate growth. Find out more: https://darwinworks.com/ Learn More About the iwon™ podcast Website: https://www.iwonpodcast.com LinkedIn: https://linkedin.com/company/iwon-podcast Success isn't overnight. That's why we tell the real stories. Takeaways: Smaller B2B tech companies can beat bigger incumbents by moving faster, listening harder, and building deeper customer relationships. Generic startup advice does not always apply to enterprise SaaS, especially when one customer can meaningfully shape the product and the business. Founders should validate the problem before falling in love with the solution, because the original idea is rarely the final version. Raising money too early can create pressure to grow before the product, customer base, or business foundations are ready. Customer enthusiasm is useful, but customer commitment matters more. Founders need to test interest with real conversations, contracts, payment, or clear commercial intent. AI can improve performance management when it helps people understand patterns, coach better, and grow in their careers, rather than simply monitoring output. Companies and tools mentioned in this episode: ClarityLoop FanDuel Multiverse Y Combinator GitHub Jira Confluence The Mom Test And many more. Disclaimer: The views expressed in this podcast are those of the individual speakers and do not necessarily reflect the views of the producers or associated organisations. This podcast is provided for informational and entertainment purposes only and should not be considered financial, legal, or professional advice. Trademarks and Copyright: The iwon™ podcast is produced by DARWIN™ Works, a trading name of BlueEyed Digital Marketing Ltd. iwon™ and DARWIN™ are registered trademarks. All content is copyright © BlueEyed Digital Marketing Ltd 2026.

    Build the Speedboat: How Small Startups Can Beat Much Bigger Competitors | iwon™ podcast | ep. 10 | Sachin Goyal

  8. Jun 25

    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 biggest challenges facing education today: preparing the next generation for a world powered by AI. A former British Army Reservist, engineering leader, and startup founder, Aatish brings a unique perspective on technology, learning, leadership, and the realities of building a business in one of the fastest-moving industries on the planet. Before launching Pedagogue, Aatish founded and exited an AI startup before spending four years helping scale Climate X through multiple stages of growth. Along the way, he learnt first-hand what works, what doesn't, and why timing, distribution, and economics often matter more than founders realise. Together, Michael and Aatish explore AI literacy, startup lessons, product-market fit, education reform, future careers, large language models, agentic AI, and why schools must rethink what "elite education" means in the age of artificial intelligence. If you're a founder, educator, parent, student, or simply curious about where AI is taking us next, this conversation is packed with practical insights and thought-provoking ideas. In This Episode• Why AI is advancing faster than most education systems can adapt • What "elite education" looks like in the age of AI • Lessons from building and exiting an AI startup • Why timing, distribution, and economics matter in startup success • Product-market fit and knowing when to pivot • Why education became Pedagogue's focus • The future of work and the skills students need most • The opportunities and risks of large language models • Agentic AI, automation, and what comes next • Why founders should avoid outsourcing all of their thinking to technology • Leadership lessons from the British Army • Why human creativity still matters in an AI-powered future Chapters00:00 AI Is Moving Faster Than Education 00:36 Welcome to the iwon™ podcast 01:40 Building and Selling an AI Startup 04:18 Startup Lessons, Risk, and Luck 07:07 The UK vs Silicon Valley 12:00 Product Market Fit and Enterprise Challenges 14:14 The Palantir Problem 16:17 Why Education Became the Focus 17:34 What Is Elite Education Today? 20:24 Why Schools Must Teach AI 23:16 Why AI Could Increase Inequality 25:49 Why Not Start With Government Contracts 31:31 Is Pedagogue the Right Solution? 34:00 The AI Boom and Startup Reality 36:52 Why Most People Misunderstand AI 38:00 Teaching AI Without Platform Bias 41:08 Agentic AI and the Future 46:00 How Founders Avoid Overengineering 50:41 Leadership Lessons Beyond Technology 54:28 Think Long Term and Compound 56:00 Are We Outsourcing Thinking? 57:50 Unknown Unknowns and Human Creativity 58:52 Final Thoughts Connect with Aatish ThakerarLinkedIn: https://www.linkedin.com/in/aatish-thakerar/ Pedagogue: https://pedagogue.io/ Pedagogue on LinkedIn: https://www.linkedin.com/company/pedagogue-schools/ Connect with Michael J. ThomasLinkedIn: https://www.linkedin.com/in/realmjt-in/ Stuck where you are with your SaaS or B2B tech product?Michael and the team at DARWIN™ Works help founders simplify their message, sharpen their positioning, and accelerate growth. Find out more: https://darwinworks.com/ Learn More About the iwon™ podcastWebsite: https://www.iwonpodcast.com LinkedIn: https://linkedin.com/company/iwon-podcast Success isn't overnight. That's why we tell the real stories. Takeaways: Artificial intelligence is advancing rapidly, while educational systems struggle to keep pace with these developments.The incorporation of AI education in countries like China begins at a remarkably young age, highlighting deficits in the UK and US educational frameworks.The role of schools extends beyond traditional education; they must prepare students for the future of work, integrating technology into their curriculums.Founders must navigate the complexities of funding and commercial viability, particularly in the fluctuating landscape of AI and technology startups. Companies mentioned in this episode: PedagogueClimatexPalantirClaudeGrokBase44Replit And many more. Disclaimer: The views expressed in this podcast are those of the individual speakers and do not necessarily reflect the views of the producers or associated organisations. This podcast is provided for informational and entertainment purposes only and should not be considered financial, legal, or professional advice. Trademarks and Copyright: The IWON™ Podcast is produced by DARWIN™ Works, a trading name of BlueEyed Digital Marketing Ltd. IWON™ and DARWIN™ are registered trademarks. All content is copyright © BlueEyed Digital Marketing Ltd 2026.

    AI Skills and Future of Work - Building a Gold Standard That Doesn't Exist (Yet) | Aatish Thakerar | iwon™ podcast Ep. 9.
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IWON™ (It Wasn’t Over Night) is a long-form podcast for ambitious founders. Wherever you are at in your business journey, you'll get something from every episode and each guest. These are the people who been there and done it. If you want to understand what it actually takes to build and scale a successful company, iwon™ is worth listening to. Each episode features honest, in-depth conversations with founders, operators and growth leaders who have built, scaled, exited or survived in the tech world. Iwon™ is hosted by Michael J. Thomas. He is an experienced marketing strategist, Cambridge-accredited coach and founded DARWIN™ Works Marketing in 2011. This isn’t surface-level advice or recycled LinkedIn BS. It's the real stories. We go deep and unscripted with every episode and every guest. It’s the real story behind: • Early mistakes and failures • Fundraising realities and financial pressure • Product and growth decisions that changed everything • Sales lessons that cost years to learn • Mental health, leadership and resilience • What genuinely moves the needle From first customers to $750m exits, IWON reveals the thinking, trade-offs and hard-earned lessons you rarely hear in public. If you are building a SaaS or tech company, leading a product or growth team, or trying to grow without chaos, this podcast will give you perspective, clarity and practical insight from people who have done it for real. New episodes every two weeks. The names iwon and DARWIN are registered trademarks. This podcast and the opinion-based content herein are wholly owned by, property of, and produced by - and is a DARWIN Works Production - a trading name of BlueEyed Digital Marketing Ltd. Copyright 2026.

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  • Creator
    Michael J Thomas
  • Years Active
    2026
  • Episodes
    17
  • Rating
    Explicit
  • Copyright
    © Copyright 2026 - iwon and DARWIN are registered trademarks. This podcast and those trademarks are wholly owned by, property of, and produced by - and is a DARWIN Works Production - a trading name of BlueEyed Digital Marketing Ltd.
  • Show Website
    iwon™ podcast with Michael J Thomas