iwon™ podcast with Michael J Thomas

At 14, Andy Choi started his first company because nobody would give him a job.

He grew it to 21 employees across three cities and, on his best days, made $2,000 a day as a teenager.

Impressive.

Now, nearly three decades and seven businesses later, Andy is candid about what entrepreneurship has cost him, what his ego got wrong and how his definition of winning has changed.

Today, Andy is the Founder and CEO of Do Good NaaS, a Nonprofit-as-a-Service platform helping businesses, creators and communities launch and scale charitable projects without the usual legal, financial and operational burden.

In this episode of the iwonTM podcast, Andy and Michael J. Thomas explore the person behind those seven businesses.

They discuss:

• Growing up in a Korean immigrant family in Oakland

• The moment Andy realised his father could not afford to buy him a burger

• How his brother's cerebral palsy shaped his understanding of service

• Starting and scaling a company at 14

• Turning youth and other perceived disadvantages into advantages

• The expensive decisions Andy made because of ego

• How founders can distinguish conviction from insecurity

• Why holding on to a business can become like remaining in an unhealthy relationship

• Why Andy nearly closed Do Good

• The responsibility founders carry for employees and investors

• Why startup life is nothing like social media makes it appear

• Why loving something does not necessarily mean you should build a business around it

• Servant leadership and what it means in practice

• What humans can continue to offer in the age of AI

• Why money matters, but should never become the destination

Andy also explains why founders should understand a problem deeply before building a company around it, why experience matters more than startup theatre and why the most valuable thing humans may offer in the age of AI is our ability to serve one another.

This is an honest conversation about poverty, faith, family, ego, leadership, responsibility, purpose and what nearly three decades of entrepreneurship can do to the person building the businesses.

CHAPTERS

00:00 He built a 21-person company at 14

01:15 Growing up poor in an immigrant family

04:42 Did responsibility make him an entrepreneur?

07:38 What his brother taught him about service

11:45 Can doing good become a competitive advantage?

14:56 Building the Alameda Teen Project at 14

19:29 What happens when the teenage boss gets it wrong?

21:35 Turning weaknesses into founder advantages

24:08 The expensive decisions driven by ego

28:30 Good ego, bad ego and decisions driven by fear

32:06 Conviction or insecurity?

35:24 The businesses he should have let go

38:31 Why Andy nearly closed Do Good

43:12 What makes humans valuable in the age of AI?

44:11 "Cash is king" and the fundamentals of business

48:37 The truth behind overnight startup success

52:16 How Andy's leadership style changed

55:26 What servant leadership actually looks like

59:31 When winning stopped being only about money

01:02:07 Launching 100 nonprofit projects in under a year

ABOUT ANDY CHOI

Andy Choi is the Founder and CEO of Do Good.

A serial entrepreneur who launched his first venture at 14, Andy has built seven businesses across marketing, technology, manufacturing, hospitality and social impact.

Do Good NaaS helps established businesses, startups, creators and communities launch and scale nonprofit projects. Its Nonprofit-as-a-Service platform provides the infrastructure required to manage areas such as legal structure, tax-deductible donations, fundraising and campaign tools.

DISCOVER MORE ABOUT ANDY CHOI AND DO GOOD NAAS

Website:

https://dogoodnaas.com/

CONNECT WITH ANDY

LinkedIn:

https://www.linkedin.com/in/andyhchoi/

ABOUT IWONTM

iwonTM stands for It Wasn't Overnight.

Most business stories show you the funding, growth, acquisition or success. iwonTM explores the false starts, uncomfortable decisions, sacrifices and lessons that came first.

Real founders. Real stories. Everything that happened before anyone called it an overnight success.

Follow iwonTM on your podcast platform so you do not miss the next episode.

CONNECT WITH MICHAEL J. THOMAS

LinkedIn:

https://www.linkedin.com/in/realmjt-in/

Visit iwon:

https://iwonpodcast.com/

Watch on YouTube:

https://www.youtube.com/@realmjt

Apply to share your founder story:

https://iwonpodcast.com/guests/

DARWIN Works Marketing:

https://darwinworks.com/

DISCLAIMER

This episode contains personal experiences, opinions and general discussion for information and entertainment only. It is not legal, financial, investment, tax, religious or other professional advice.

Views expressed belong to the individual speakers and do not necessarily represent iwonTM, DARWIN or any company, client, partner or organisation mentioned.

Please conduct your own research and seek appropriately qualified advice before making business, financial or other significant decisions.

The names iwon and DARWIN are registered trademarks, protected under copyright.

The iwon podcast is a DARWIN Works Production.

Copyright 2026.

Dr Steven Charlap lost his brother, a cardiologist, following a misdiagnosis.

That loss became deeply personal.

Now, at 67, Steven is the Founder and CEO of Medome, an AI-first healthcare platform designed to help patients and doctors build a more complete picture before important medical decisions are made.

And he has invested more than $4 million of his own money into the mission.

Steven is an NYU-trained physician, Harvard MBA and Stanford Distinguished Careers Institute Fellow who has spent decades building healthcare companies.

In this episode, we talk about the human story behind Medome, the real potential of AI in healthcare, the limitations and risks, and one very big question:

Can AI actually help save lives?

We get into:

• How losing his brother changed the direction of Steven's life

• Why incomplete medical histories can contribute to diagnostic errors

• Whether AI could eventually outperform doctors in some areas of diagnosis

• Why AI should support clinicians rather than simply replace them

• The challenge of processing thousands of possible diseases and symptoms

• Why asking better questions could be one of AI's biggest advantages

• Steven's belief that AI can help reduce avoidable harm

• Why doctors themselves may become some of the strongest advocates for better diagnostic tools

• Building trust in medical AI

• The importance of verification rather than blindly trusting an algorithm

• Privacy, patient data and healthcare technology

• Putting more than $4 million of his own money into building Medome

• Working seven days a week at 67

• Founder resilience, mission and personal sacrifice

• And what Steven believes healthcare could look like in the years ahead

This is not simply a conversation about technology.

It is about what happens when a personal tragedy becomes a life's mission.

ABOUT DR STEVEN CHARLAP

Dr Steven Charlap is the Founder and CEO of Medome.

He earned his medical degree from NYU Grossman School of Medicine and later completed an MBA at Harvard.

Steven was also a Fellow at Stanford University's Distinguished Careers Institute, where his work included extensive study in genetics, genomics and preventive medicine.

He has spent more than 40 years in medicine and healthcare and has founded and built healthcare businesses since 1989.

His current focus is Medome, which uses AI to help collect and organise detailed patient information, identify clinically relevant questions and support better-informed conversations between patients and doctors.

Medome describes itself as a tool designed to enhance medical decision-making, not replace professional medical care.

MORE ABOUT DR. STEVEN & MEDOME

Medome:

https://medome.ai/

Steven Charlap on LinkedIn:

https://www.linkedin.com/in/steven-charlap-md-mba-8911906/

Steven's Stanford profile:

https://dci.stanford.edu/fellow/steven-s-charlap-md-mba/

Steven on Medium:

https://medium.com/@scharlap_807

ABOUT THE IWON PODCAST

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 sacrifices.

The difficult decisions.

And the lessons founders normally have to learn the expensive way.

No hype.

No overnight-success rubbish.

Just honest conversations about what it actually takes to build something.

WATCH & FOLLOW IWON AND MICHAEL J THOMAS

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/

Companies mentioned in this episode:

• ChatGPT (OpenAI)
• Claude (Anthropic)
• Harvard University
• Harvard Business School
• Stanford University
• New York University Grossman School of Medicine
• National Institutes of Health (NIH)
• National Health Service (NHS)
• Nike
• McDonald's
• Twitter
• Amazon
• American Express
• iwon Podcast
• Madome.ai

DISCLAIMER

This episode discusses healthcare, medicine, artificial intelligence and diagnostic technology.

The views and claims expressed are those of the individual speakers and do not necessarily reflect the views of the producers or associated organisations.

Nothing in this podcast should be considered medical advice, diagnosis or treatment, and it is not intended to replace consultation with a qualified healthcare professional.

AI-based healthcare tools, including Medome, have limitations and should not be relied upon as a sole source of medical diagnosis or treatment.

It is not a substitute for professional medical advice and recommends consulting an appropriate healthcare provider for medical decisions.

If you have concerns about your health, seek advice from a qualified medical professional. In an emergency, contact the appropriate emergency service in your country.

The iwonTM Podcast is produced by DARWINTM Works, a trading name of BlueEyed Digital Marketing Ltd.

iwonTM and DARWINTM are registered trademarks.

© BlueEyed Digital Marketing Ltd 2026.

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.

HairTracker 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.

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?

The 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:

• Tinder
• LinkedIn
• Y Combinator
• Hair Tracker
• Capture Me
• Ping My House
• Zoopla
• Etsy
• Beauty Tracker
• Innovate UK
• Apple App Store
• Facebook
• Instagram
• ChatGPT

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.

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.

More 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.

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/

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.

The 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.

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:

• Buffer
• Dropbox
• Superhuman
• Twitter
• X
• Facebook
• LinkedIn
• Pinterest
• Instagram
• Google
• Google Drive
• Gemini
• ChatGPT
• Claude

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.

Michael 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

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.com
• Interested 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.

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?

AI 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.

Sachin 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

European 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/

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

This episode contains news commentary, research summaries and personal opinion. The opinions and interpretations expressed by Michael J. Thomas are his own and are presented as an exercise of freedom of expression. They do not necessarily represent the views of any guest, source, company, employer, client, partner or other organisation mentioned.

The episode is provided for information, discussion and entertainment only. It is not legal, financial, investment, tax, technical, cybersecurity or other professional advice. Some stories are based on third-party reporting and publicly available information which may change, develop or be disputed after publication. Original sources are linked so you can review the reporting and reach your own conclusions. Always carry out your own research and, where appropriate, seek advice from a suitably qualified professional before making business or investment decisions.

Add accurate chapters after the live recording is complete. For the podcast version, timestamps are still useful in the written show notes even where a listening app does not render formal chapters. Use the final edited audio/video as the source of truth for timings.

Takeaways:

• Founders often struggle to keep pace with the rapid developments occurring in the tech landscape, affecting their ability to innovate effectively.
• The ongoing investment in AI companies suggests a dual narrative where genuine growth potential coexists with concerns about inflated valuations, reminiscent of the dot-com bubble.
• It is crucial for founders to assess not only the benefits AI brings to their products but also the risks associated with reliance on a single AI provider.
• As regulatory frameworks like the EU AI Act evolve, founders must consider compliance not only as a legal obligation but as a potential competitive advantage in securing larger customers.
• The relationship between marketing and sales is pivotal; clarity on what constitutes a viable lead is essential for aligning efforts and optimizing conversion rates.
• In the AI era, understanding the economics of usage is vital, as increased AI deployment can lead to unforeseen costs that impact profitability.

Companies mentioned in this episode:

• Nvidia
• European Central Bank
• Anthropic
• Fanduel
• Multiverse
• Clarity Loop
• Microsoft
• Google
• Honzada
• NFL
• Pedagog
• Etched

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:

• Microsoft
• Unilever
• Novo Nordisk
• ServiceNow
• SAP
• Capgemini
• OpenAI
• Hugging Face
• Modal Labs
• Dremio
• Prior Labs
• Elon Musk
• Sam Altman
• Andrew Yang
• Martin Ford

• Elon Musk interviewed by The Economist
• Sam Altman on AI and the “jobs apocalypse”
• Andrew Yang and Martin Ford, “The Robots Are Coming for Your Job”.
• Microsoft launches Microsoft Frontier Company
• ServiceNow Q2 2026 results and highlights
• SAP trims its 2026 profit outlook
• Capgemini raises its growth target as businesses prepare for AI
• OpenAI agent security incident
• Hugging Face security incident disclosure
• Cloudflare 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.

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.

Michael 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

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.com
• Interested 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 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.

• Why a working AI prototype is not necessarily a dependable product
• The difference between vibe coding and responsibly assisted development
• What Amazon’s experience with its Kiro coding agent can teach founders
• Why human review and accountability still matter
• How Uber reportedly exhausted its annual AI coding budget in four months
• Why producing more code does not automatically create more customer value
• Meta’s projected investment of up to $145 billion in 2026
• Why Meta is exploring ways to commercialise its AI infrastructure
• Humata Health’s warning about the difficult “final mile”
• How AI is changing the build-versus-buy decision
• Why security, compliance, reliability and support can become a competitive moat
• Three questions every founder building with AI should answer

00:00 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

1. What would happen if a customer stress-tested your product tomorrow?
2. Are the depth, reliability and value of your product clear to prospective buyers?
3. Are you creating enough genuine value to make customers want to stay when a competitor can build something similar?

• Michael 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 AI
• Financial Times: Amazon service was taken down by AI coding bot
• The Guardian: Amazon’s cloud reportedly hit by outages involving AI tools
• Business Insider: Uber COO says AI spending is becoming harder to justify
• Reuters: Meta raises its 2026 capital expenditure forecast to as much as $145 billion
• Reuters: Meta building a cloud business to sell excess AI capacity
• Reuters: Meta and Anthropic discuss a potential $10 billion compute agreement
• Forbes: Dr Jeremy Friese on how the build-versus-buy decision has changed
• Gartner: Over 40% of agentic AI projects predicted to be cancelled by the end of 2027

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.

This 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:

• Amazon
• Uber
• Meta
• Humata Health
• Loveable
• Base44

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.

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.

• 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

00:00 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

LinkedIn:

https://www.linkedin.com/in/aatish-thakerar/

Pedagogue:

https://pedagogue.io/

Pedagogue on LinkedIn:

https://www.linkedin.com/company/pedagogue-schools/

LinkedIn:

https://www.linkedin.com/in/realmjt-in/

Michael and the team at DARWIN™ Works help founders simplify their message, sharpen their positioning, and accelerate growth.

Find out more:

https://darwinworks.com/

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:

• 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:

• Pedagogue
• Climatex
• Palantir
• Claude
• Grok
• Base44
• Replit

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.