Podcast
Millennial Masters
Hosted by with Daniel Ionescu · EN
Conversations with founders and leaders on business, growth, AI, and how modern companies adapt. Millennial Masters is for people building businesses and leading teams.
millennialmasters.net
millennialmasters.net
20episodes
Episodes
Newest firstAll episodes
Why builders make bad entrepreneurs 🧱 Matt Watson
2w ago01:05:10Tap to summarizeMatt Watson has spent years building software companies, including Full Scale, where he helps businesses hire and manage software development teams. He is also the author of Product Driven, a book about turning product thinking into real business growth.That matters because Matt has lived close to the gap between making software and building a company people actually want. His warning feels especially useful now that AI has made product building look easier than ever. Shipping faster does not solve the harder parts of entrepreneurship. You still need to understand the customer, the market, the problem, the positioning, and why anyone should care enough to buy.In this episode, we get into why builders often struggle to become entrepreneurs, why product vision cannot be handed off, and what still matters when AI makes the first version easier to create.What we cover1️⃣ Why technical founders still get stuck on the commercial sideMatt explains how builders can stay busy improving the product while the real business problem stays untouched.2️⃣ The trap AI makes easier to fall intoBuilding is now faster, cheaper, and more addictive. This part gets into the danger of mistaking constant output for actual progress.3️⃣ Product vision that cannot be outsourcedIf the thinking stays vague in the founder’s head, the team ends up guessing. Matt talks through what clear product direction really requires.4️⃣ Why perfect code is the wrong obsessionSoftware changes, teams change, and standards move. The business cannot be built around the fantasy that the product will stay pristine forever.5️⃣ The loneliness that comes with building seriouslyThe episode also gets into founder isolation, changing relationships, and the need for people who understand the pressure without needing the whole backstory.Chapters00:00 Introduction to Matt Watson02:57 The birth of VinSolutions05:43 Growth, pressure, and early challenges08:11 Why he decided to sell10:19 The founder and CTO trap12:49 Scaling and delegation problems16:03 What AI changes in software development18:01 From engineers to developers19:42 Product Driven as a way of thinking22:04 The changing role of product management29:50 What technical debt actually does36:50 Leadership inside development teams44:52 From AI prototypes to scalable products46:32 AI in prototyping and development48:14 The code review problem51:43 Building trust in business relationships56:07 How exits affect personal relationships01:00:37 What entrepreneurship takes out of youGet more founder interviews and practical business lessons in the Millennial Masters newsletter at MillennialMasters.netSend this to a builder who still needs to learn how to sell 📤 Get full access to Millennial Masters at millennialmasters.net/subscribe
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Don’t hire helpers, hire owners 👑 Gavin Bell
3w ago01:04:37Tap to summarizeGavin Bell built and sold a paid media agency by the age of 30. From the start, he wanted the business to become sellable, which forced a different kind of thinking around hiring, delivery, and how much still depended on him.One of the clearest lessons from his exit is that founders often hire help when they really need ownership. A helper takes tasks off your plate. An owner takes responsibility for an outcome. That difference shapes how the business grows, how much pressure stays with the founder, and whether the company can ever run properly without you in the middle.In this episode, we get into building a business that someone would actually want to buy, why your first hires set the standard, and how founders keep slowing the company down without realising it.What we cover1️⃣ The difference between help and ownershipGavin explains why taking tasks off the founder’s plate is not enough if nobody is truly carrying responsibility for an outcome.2️⃣ What makes a service business easier to sellThis part gets into systems, delivery, capacity planning, and the proof a buyer needs that the company can keep working when the founder leaves.3️⃣ Why founders need to understand the work firstDoing the job yourself early on helps you recognise quality, judge capacity properly, and delegate with a much clearer standard.4️⃣ How approval habits create dependencyStaying too close for too long teaches the team to keep coming back for sign-off, even when the founder thinks they are just protecting quality.5️⃣ Choosing a model that fits the life you wantAfter selling Yatter, Gavin became clearer on the kind of business he did and did not want to build next.Chapters00:00 Intro to Gavin Bell01:46 From fitness to Facebook ads03:59 The scaling problems that showed up early06:57 Why he rebranded and built Yatter09:55 What the early Yatter years taught him12:34 Delegation, trust, and building a team15:20 Systemising delivery inside the agency17:48 How the acquisition process unfolded20:27 What changed in advertising over time22:39 AI, personalisation, and the future of ads26:14 The downside of hyper-personalised advertising33:41 Where social media and AI go next37:17 What he learned from building and exiting41:08 Starting a new venture in healthcare46:52 Personal brand and why it matters52:13 Building a business that works without you57:30 How AI fits into business operationsGet more founder interviews and practical business lessons in the Millennial Masters newsletter at MillennialMasters.netSend this to someone stuck in delivery 🧱 Get full access to Millennial Masters at millennialmasters.net/subscribe
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Investors don’t fund ideas 💸 James Church
Apr 2701:10:53Tap to summarizeJames Church sees what most founders miss about raising money. He works closely with companies going through the process, and the pattern is consistent. Founders focus on the pitch, the deck, and the story they want to tell. Investors are reading something else entirely.The decision starts forming long before the meeting. Your traction, your positioning, how clearly you explain the problem, and how you show up in the market all carry more weight than any polished slide. That is where a lot of founders get caught out. They treat fundraising like a moment instead of a process, and by the time they are pitching, much of the work that matters has already been done or neglected.In this episode, we get into how investors really make decisions, why fundraising is closer to sales than storytelling, when not to raise, and how to build the kind of trust that makes people want to back you before you even ask.James is offering Millennial Masters listeners his bestselling book, The Investable Entrepreneur, free via his websiteWhat we cover1️⃣ The signals investors read before the pitchJames explains why traction, positioning, and market credibility shape the decision earlier than most founders realise.2️⃣ What a polished deck cannot hideSlides help, but they do not fix weak fundamentals. This part gets into the gaps investors spot quickly when the business story does not hold up.3️⃣ Why fundraising behaves more like salesThe process is less about performance and more about helping someone get comfortable making a high-risk decision.4️⃣ Trust built before the askJames talks about the role of consistency, communication, and how founders show up over time when investors are deciding who they believe in.5️⃣ Knowing when funding is the wrong moveNot every company should raise. The episode looks at when outside capital creates more pressure than advantage.Chapters00:00 Introduction to James Church02:32 From graphic design to investment consulting05:25 Understanding the high-performance founder12:41 The art of investor engagement17:12 The journey of fundraising23:38 Timing your fundraising efforts35:51 Overcoming shyness and building confidence44:06 Networking and using existing connections49:33 Understanding angel investors and their expectations52:49 Navigating dilution and equity distribution01:02:41 When not to raise fundsGet more founder interviews and practical business lessons in the Millennial Masters newsletter at MillennialMasters.netShare this with a founder chasing funding 📩 Get full access to Millennial Masters at millennialmasters.net/subscribe
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Hire your army, don’t rent mercenaries ⚔️ Yannik Schrade
Apr 1900:46:23Tap to summarizeYannik Schrade thinks a lot of founders are too casual about what they outsource. He is the founder of Arcium, building privacy infrastructure at a time when AI is making software easier to build, easier to copy, and more exposed than most people realise.His view is simple: If your edge lives in the product, the knowledge, and the way the team works together, you cannot keep giving that away and expect to build a real moat.In this episode, we get into in-house teams versus outsourced work, privacy as a competitive advantage, how AI is changing software, and why founder taste matters more than technical skill on its own.What we cover1️⃣ The work that should stay inside the businessYannik makes the case for keeping the core knowledge, product thinking, and team learning close rather than letting too much of it sit outside.2️⃣ Why privacy can strengthen the productThis part gets into treating privacy as part of the offer itself, not just a legal or compliance issue sitting in the background.3️⃣ What cheaper AI tools are doing to softwareAs building gets faster and easier, copying gets easier too. Yannik talks through the risks that come with that shift.4️⃣ Founder taste as the thing that holds it togetherTechnical skill matters, but once products get more complex, judgement around what should exist and what is worth building starts to matter even more.5️⃣ Putting yourself in rooms where useful things happenThe conversation also gets into luck, exposure, and why more opportunities come from being in enough real situations for something unexpected to open up.Chapters00:00 Meet Yannik Schrade02:04 From apps to privacy infrastructure09:26 Why the old model stopped working18:14 Building Arcium around privacy25:44 Where financial systems go next27:01 What healthcare gets wrong about data27:46 The basics behind computational primitives28:42 AI, ethics, and privacy pressure29:39 Whether privacy can support a business model30:39 Funding privacy technology with VC money31:48 Fixing data silos in healthcare33:39 Why everyday apps should worry you36:05 Messaging apps and what secure really means39:38 Convenience versus privacy in AI tools41:38 Building a team that keeps the edge43:37 Putting yourself where luck can happenGet more founder interviews and practical business lessons in the Millennial Masters newsletter at MillennialMasters.netKnow a founder still outsourcing their edge? Send them this episode ⚔️ Get full access to Millennial Masters at millennialmasters.net/subscribe
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A good business can still trap you 🪤 Melissa Kwan
Apr 1401:12:12Tap to summarizeMelissa Kwan has spent years building, selling, and starting again. By the time she launched eWebinar, she had a much clearer idea of what she wanted this time and what she was no longer willing to compromise on. For a while, it looked like it was working. Then growth slowed, old habits started creeping back in, and she realised the problem was not just effort or execution. It started earlier.Sometimes the market does not understand the problem the way you think it does, and no amount of pushing fixes that until the positioning gets clearer. In this episode, we get into lifestyle by design, founder drift, weak positioning, pricing, hiring, burnout, and the cost of staying too long in a business that no longer fits.What we cover1️⃣ When the business starts pulling you in the wrong directionMelissa talks about what happens when a company looks healthy on paper but keeps dragging you further from the life you were trying to build.2️⃣ Positioning problems that make everything heavierWhen the market does not quite understand what you are or why it matters, sales, marketing, and growth all get harder than they should be.3️⃣ Why more effort does not solve a message problemThis part gets into the temptation to push harder when growth slows, and why that often misses the real commercial issue.4️⃣ How founder drift quietly builds upOne compromise at a time, founders can end up carrying roles, pressures, and work they were never meant to keep doing.5️⃣ The cost of staying too longMelissa is clear on what happens when you keep forcing a setup that no longer fits, whether that is the offer, the pricing, the positioning, or the business itself.Chapters00:00 Meet Melissa Kwan01:50 Leaving corporate behind03:14 Building a business from zero07:21 Turning services into a product09:38 Bootstrapping, debt, and profitability12:40 Finding a model that fits15:38 What “lifestyle business” really means18:55 Choosing a problem you care about21:30 When sales is the wrong channel23:55 What stopped working in marketing26:47 The challenge she could not ignore29:29 Rethinking the identity of the business32:11 The inner work that changed everything41:41 Treating sales like a science43:26 Taking marketing back in-house45:42 Hiring without losing the culture47:15 Pricing mistakes and what they cost52:48 Getting to real product-market fit57:43 Building something you can sustain01:01:22 The sacrifices behind the freedomGet more founder interviews and practical business lessons in the Millennial Masters newsletter at MillennialMasters.netShare this with someone stuck on positioning 🟣 Get full access to Millennial Masters at millennialmasters.net/subscribe
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Bad setup kills good AI ⚙️ Ben Tasker
Apr 600:49:49Tap to summarizeBen Tasker works close to the part most companies would rather skip. He leads AI upskilling and reskilling at scale, helping tens of thousands of employees learn how to use these tools properly inside real organisations.His background spans data science, product, healthcare, education, and workforce transformation. That gives him a clearer view than most of where AI is genuinely helping and where it is making things worse. A lot of companies say they are investing in AI when what they really mean is they bought a tool, opened a few licences, and hoped for the best. Ben’s view is more grounded. Most AI projects fail because the basics are weak: poor data, weak guardrails, little training, no real change management, and no clear idea of what the tool should actually be doing.In this episode, we get into why AI is still misunderstood inside businesses, why treating it like simple automation causes problems, how leaders should think about upskilling, and what changes when junior work starts disappearing first.What we cover1️⃣ What AI is actually doing under the hoodBen explains why these systems are predicting rather than understanding, and why that matters when founders expect too much from weak prompts and vague instructions.2️⃣ The real reasons AI rollouts failThis part gets into poor setup, weak training, bad change management, and why buying a licence is not the same as changing how a business works.3️⃣ Where AI helps most inside a teamThe better use case is often augmentation rather than replacement. Ben talks through where stronger people can move faster and make better decisions with the right support.4️⃣ The messy data problem underneath the hypeBad systems, inconsistent inputs, and poor data hygiene still shape what AI can do well. The shiny layer does not fix that.5️⃣ What happens when junior work starts shrinkingThe episode also looks at entry-level roles, the pressure now hitting early-career work, and the skills people need if they want to stay useful through the shift.Chapters00:00 Introduction to Ben Tasker01:37 Data came before AI did03:27 ChatGPT changed what people think AI is06:16 Useful does not mean trustworthy09:33 AI is not the same as automation11:57 The right AI job depends on the size of the business14:52 AI can guide you, but it cannot think for you16:49 Start small before you break something bigger19:17 What to check before AI goes live21:21 Reviewing AI work without wasting time26:32 Advanced work still needs human judgement28:26 Human review is still doing the heavy lifting29:19 Bad data will break good AI33:10 AI skills are rising, human skills still matter35:44 Fear makes people resist AI before they learn it39:17 Junior roles are getting squeezed first43:15 The better move is augmentation, not replacement47:25 What businesses should do next with AIGet more founder interviews and practical business lessons in the Millennial Masters newsletter at MillennialMasters.netSend this to a founder using AI every day 📤 Get full access to Millennial Masters at millennialmasters.net/subscribe
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Proving the sceptics wrong 🌙 Michelle Bell
Mar 2900:53:09Tap to summarizeMichelle Bell did not stumble into this idea by accident. Before founding Cosmic Universe, she worked in journalism and SEO, watching in real time what people searched for, what they clicked, and what they kept coming back to. One pattern stood out. Astrology was not a side interest or a joke category. The demand was huge, the audience was engaged, and the market was much bigger than most people realised.That insight became Cosmic, a personality and connection platform built around astrology, compatibility, and live experiences. What sounds niche on paper has turned into something much more interesting in practice: a business sitting at the intersection of identity, loneliness, self-discovery, and how people now try to connect.In this episode, we get into why Michelle left journalism to build something of her own, what she saw in the data that others missed, and what it takes to build in a category many people still dismiss too quickly.What we cover1️⃣ The search signals that pointed to a real marketMichelle explains how search demand revealed an audience with real intent long before astrology looked like an obvious business opportunity.2️⃣ Building in a category people dismissScepticism can put founders off too early. Michelle talks about seeing past that and focusing on whether the pull is real.3️⃣ What users were really looking for underneath the productThe bigger opportunity was not just content. It was connection, compatibility, self-discovery, and the emotional needs users kept signalling.4️⃣ The pressure that comes with building aloneThis part gets into solo founder pressure, decision fatigue, and how to keep going when the weight sits with you.5️⃣ Motherhood, growth, and changing as the business changesThe episode also looks at user behaviour, leadership, and what it means to keep building while your life keeps moving too.Chapters00:00 Introduction to Michelle Bell01:36 Journalism trained her for founder pressure04:24 She spotted a real astrology market08:15 A different answer to dating app fatigue10:45 Turning the app into live events13:02 People want connection but avoid the risk15:38 The pressure of being a solo founder18:39 Measuring meaningful connection20:57 Social media still drives growth23:21 What sceptics miss about astrology26:34 Why founders are wired differently29:12 When personality helps or hurts leadership30:43 Building a business through motherhood32:13 Building in a space people dismiss34:21 Community matters more than audience37:18 What power users do differently39:33 Motherhood, work, and constant adjustment43:12 New York, London, and raising children44:31 Why walking clears her head46:00 Growth means changing your mind47:55 The reality behind building a businessGet more founder interviews and practical business lessons in the Millennial Masters newsletter at MillennialMasters.netSend this to someone sitting on an idea people doubt 📤 Get full access to Millennial Masters at millennialmasters.net/subscribe
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Why working harder stops working 🔁 Damon Flowers
Mar 2300:54:48Tap to summarizeDamon Flowers has spent more than 20 years building and scaling companies across eCommerce, SaaS, and coaching. He is a four-time CEO with two eight-figure exits, including growing one business from $3.5 million to $30 million in two years.In this episode, we get into the real reason growth starts to stall for a lot of founders. It is rarely effort. It is usually structure. Damon explains how to stop being the bottleneck, build a business that can move without you, and create operating systems that hold up as you scale.What we cover1️⃣ Why founders stay too central for too longWhen too much runs through you, growth creates drag. Damon breaks down how to spot the decisions, approvals, and workflows that still depend on you.2️⃣ Harder work does not solve a broken structureMore hours can keep things alive, but they rarely fix the underlying issue. This part gets into redesigning the way work flows across the business.3️⃣ What real delegation actually requiresStepping back is not about good intentions. It needs clear ownership, better handovers, and systems people can follow without pulling you back in.4️⃣ How to get teams thinking like ownersDamon shares how better accountability, visibility, and rhythm can change the way a team operates.5️⃣ Where AI fits into a better operating systemUsed properly, AI can remove friction and improve execution. Used badly, it just adds more noise.Chapters00:00 Introduction to Damon Flowers03:24 Early bruises in business07:03 Knowing your strengths and blind spots08:11 Better partners, better outcomes12:08 Stepping out of the middle18:16 Paying to buy back your time20:56 Delegating the low-value work23:43 Hiring, roles and handover26:12 The lonely side of running a business28:08 Getting staff to think like owners30:40 Losing sight of the numbers33:25 Cadence, dashboards and the right metrics37:52 Stabilise, build, optimise, grow41:39 AI inside the operating system45:53 Training your team to use AI wellGet more founder interviews and practical business lessons in the Millennial Masters newsletter at MillennialMasters.netSend this episode to the busiest founder you know 👀 Get full access to Millennial Masters at millennialmasters.net/subscribe
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Your business still needs your voice 📣 Jess Jensen
Mar 1700:52:12Tap to summarizeJess Jensen has spent more than 20 years working across brands including Nestlé, Adidas, Microsoft, and Qualcomm, right as digital marketing and social media started reshaping how businesses build trust. She now runs Copilot Communications, helping founders and executives build a public presence that supports the business instead of hiding behind the brand.In this episode, we get into why so many leaders still stay quiet online, why polished company messaging often falls flat, and why founder visibility now plays a bigger role in trust, hiring, sales, and long-term brand value than most people realise.What we cover1️⃣ Why your company cannot speak for youA polished brand helps, but people still want to know who is behind the decisions. Jess explains why founder visibility shapes trust faster than corporate messaging ever can.2️⃣ People judge the founder before the businessBefore someone buys, joins, or replies, they usually look at the person behind the company. This part gets into how your online presence shapes that first impression.3️⃣ Why simple thinking travels furtherWhat cuts through is not polished waffle. It is clear ideas, useful lessons, and honest communication people can actually remember.4️⃣ Authority takes longer than most founders thinkA few posts rarely change much. Jess talks about the compounding effect of showing up consistently over time.5️⃣ Why visibility is part of leadership nowLeading a business now includes communicating in public. Jess breaks down how sharing your thinking helps people understand your direction, values, and judgement.Chapters00:00 Introduction to Jess Jensen02:15 Early agency career and learning everything07:14 MBA, Nestlé and the Fortune 500 path09:58 Adidas, Facebook and early digital marketing11:59 Microsoft, Qualcomm and the tech shift15:01 What leaders can say beyond the company17:41 Causes, values and leadership identity20:35 Choosing causes and charitable engagement22:20 Why simple language builds trust26:33 Why leadership can feel lonely29:12 LinkedIn beyond the digital CV32:24 Mixing personal and professional identity35:23 Why imperfection builds trust37:57 Why founders miss the audience40:24 Leaders doing social media well43:04 Should leaders outsource LinkedIn?45:50 Using AI to shape better content47:23 What entrepreneurship taught Jess48:55 Why brand building takes timeGet more founder interviews and practical business lessons in the Millennial Masters newsletter at MillennialMasters.netSomeone in your network is hiding behind the company logo. Send them this 🎧 Get full access to Millennial Masters at millennialmasters.net/subscribe
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The ego trap behind your £10 tasks 🪤 Gary Das
Mar 1000:57:12Tap to summarizeGary Das built a seven-figure mortgage business with a team of 15. It still depended on him far more than it should have.Deals, decisions, and day-to-day problems kept finding their way back to him. The business had scale, but not separation. Instead of trying to patch it, Gary shut it down and rebuilt it properly. That reset led to the £10 task rule, a simple way to spot where your time is leaking and where ego is keeping you stuck.In this episode, we get into what keeps founders trapped in low-value work, the systems problems that quietly cap growth, and the mindset shift required to build a business that can move without you at the centre of everything.What we cover1️⃣ The £10 tasks keeping founders stuckGary breaks down the low-value work that keeps founders too close to the engine, even when the business looks successful from the outside.2️⃣ Ego, control, and the need to stay involvedBeing the closer, the fixer, or the person with all the answers can feel productive. It also keeps the team dependent on you.3️⃣ Bad leads, wasted budget, and false momentumGary shares what years of paying for weak leads taught him, and why trust, referrals, and reputation usually bring better business.4️⃣ When hustle stops workingMore effort can cover cracks for a while. It does not solve the structural problem underneath.5️⃣ Getting your team to think for themselvesThe real shift starts when people stop bringing you every problem and start bringing solutions.Chapters00:00 Introduction to Gary Das02:09 When success starts to feel miserable03:49 The reset that changed everything06:57 Why founder control becomes the problem12:51 The ego trap that kills businesses15:44 Why referrals beat paid leads18:32 Lead handling that keeps people warm21:20 The 3 lead magnets that convert24:12 Why founders get marketing wrong27:10 The first hire that buys back time31:16 Delegation, systems, and where to start34:47 What to automate and what to keep human40:18 Training people to think for themselves46:01 Metrics that show if you’re really scaling53:35 Starting again after building successGet more founder interviews and practical business lessons in the Millennial Masters newsletter at MillennialMasters.netShare this with someone who needs this today ⚡ Get full access to Millennial Masters at millennialmasters.net/subscribe
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