Podcast
Startup Hustle
Hosted by Startup Hustle · EN
Startup Hustle is a podcast for entrepreneurs, by entrepreneurs. With the mission of telling the real story of startups and entrepreneurs, topics range from funding to failure and beyond. If you want to start, own, or build a business then you're in the right place.
41episodes
Episodes
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LeadershipOS Decoded: Building Teams That Run Without You in the Room
1w ago00:29:49Tap to summarize"Back in the 1900s when I was crossing the Great Plains in a covered wagon, programming in the back, the cover headline was: Software Development is Dead."I talked with Anthony Jackson, a CTO with 30 years across healthcare tech and enterprise software and author of the Architecture Protocol series, on Startup Hustle this week. Anthony is the creator of LeadershipOS, a framework for building teams that keep running when the leader isn't in the room.Here's what you'll get out of it:⚡ Why "software development is dead" has been a headline for 30+ years, and why the human judgment layer never goes away⚡ Why the real gap isn't more engineers, it's product people (and engineers who think like them)⚡ What actually changes when you go from individual contributor to manager, and why almost no company trains you for it⚡ Why every line of code still needs a name attached to it, especially in regulated industries⚡ How "lossy compression" quietly ruins decisions as they filter up and back down through management⏱️ Episode Breakdown00:32 Introduction and Anthony Jackson's background02:13 Is software development dead again?03:14 The impact of AI on coding and human judgment04:07 The importance of responsibility in software development05:59 The challenge of product management and customer feedback10:18 Transitioning from individual contributor to manager11:36 Building effective teams and leadership culture14:41 Anthony Jackson's leadership OS book and approach18:26 The significance of company and team culture21:07 The impact of good and bad managers21:38 Anthony Jackson's newsletter and coaching23:14 Connecting software developers with customers25:06 Empathy for users and understanding their experience28:18 Where to find Anthony Jackson's resources and booksLinks & ResourcesConnect with Anthony Jackson on LinkedInAnthony Jackson's Website - https://technicaleader.coachWhat Smart CTOs Are Doing Differently With Offshore Teams in 2025Subscribe to the Global Talent SprintFull Scale – Build your dev team quickly and affordablyIf you’re trying to get your team out of the basement and into real product ownership, this episode is your playbook. Stop being a ticket factory. Build teams that think, create, and lead.Follow the show, rate it, and send this to someone who’s still trying to do “real Scrum.” They need it more than you do.
Transcribe →It's Not About the Code. It's About the Problem.
2w ago00:28:36Tap to summarizeI don't view engineers being out of a job. I view software engineers finally coming back to a real job."I talked with Adrian Gutierrez, co-founder of Ledgre, on Startup Hustle this week. Ledgre is an AI-native accounting platform built specifically for real estate investors, putting agentic AI to work doing the bookkeeping instead of handing you one more piece of software to manage.Here's what you'll get out of it:⚡ Why he was the startup's bookkeeper by hand for a year before writing a line of product, and why doing things manually first is the shortcut⚡ Why AI didn't kill software engineering, it exposed that distribution and the value prop were always the hard part⚡ Why domain knowledge beat his development skills every time when getting Ledgre off the ground⚡ What running a startup as a digital nomad across Europe, Spain, and Argentina taught him about which problems are actually worth solving⏱️ Episode Breakdown00:42 Introduction to Adrian Gutierrez and Ledger01:04 Adrian's background in FinTech and PropTech00:49 The origin story of Ledgre and market gaps02:54 How AI is transforming property management tools04:11 Adrian's experience owning rental properties05:18 The importance of domain knowledge in product development06:18 Manual bookkeeping and workflow complexity07:15 Scaling wisely and understanding problems before automating08:24 The importance of iteration and customer feedback08:52 Challenges of outreach and building relationships10:16 Cold outreach and response rates11:03 The impact of AI on distribution and problem-solving12:10 AI exposing weaknesses in traditional software development13:36 Reviving software engineering practices with AI14:32 Shift in marketing and distribution roles15:55 Using AI for marketing and SEO automation17:22 AI's role in software development and team management21:10 Living as a digital nomad and its impact on business22:45 Traveling and understanding global fintech landscapes24:33 Financial and payment infrastructure differences worldwide25:13 The value of solving real problems in different markets25:48 How to learn more about Ledger and AdrianIf you're building a product, leading engineers, or working in fintech and proptech, this one is worth your time.Listen to the Startup Hustle podcast anywhere you listen to podcasts!Links & ResourcesConnect with Adrian Gutierrez on LinkedIn - https://www.linkedin.com/in/adrian--gutierrez/Ledgre Website - https://www.ledgre.ai/
Transcribe →The Speed of Context: Why AI Changed What Engineers Actually Do
Jun 2500:25:18Tap to summarizeMost engineering teams are still optimizing for the wrong thing. They chase the speed of code when the real bottleneck is the speed of context. Matt Watson and Eban Bisong, founder and CEO of Senvi, get into what actually changes when AI moves from a coding tool to a teammate.Eban has spent his career as a founding engineer, and his approach is hands-on: don't tell skeptical engineers AI works, show them, every standup, until the pushback turns into excitement. At Park DNA he built "RTD2," an OpenClaw-powered droid wired read-only into their data sources, Slack, and Jira. It answered support questions before an engineer could, created its own bug tickets, and joined meetings through Fireflies so nothing got lost. The lesson underneath all of it: record everything, because the team that captures the most context ships the right thing fastest.Matt also shares his own three-week rabbit hole with Claude Cowork, $8K in tokens, a fully rebuilt Full Scale website, a thousand dead blog posts deleted, and 200 more rewritten. They go a few rounds on why it's a bad time to be a coder but a great time to be a builder, why "good enough" is a real standard and not a cop-out, and why ownership beats asking permission every time.If you build software or lead an engineering team, listen now. And if you want to try Eban's voice-first AI journal, visit senvi.ai.⏱️ Episode Breakdown00:42 From Founding Engineer to Solo Founder01:52 Using AI as an Engineering Leader03:24 Building RTD2: An AI Teammate for Support05:27 The Speed of Context, Not Code06:11 Why You Should Record Everything08:59 Winning Over AI-Skeptical Engineers11:50 The AI Spectrum Across 80 Clients13:35 A Bad Time to Be a Coder, a Great Time to Build14:03 Why "Good Enough" Is Good Enough14:52 Human-in-the-Loop and Reviewing AI's Work16:28 Going All-In on Senvi19:01 Validating the Product With a Beta Group21:01 Bootstrapping a Truly AI-Native CompanyLinks & ResourcesConnect with Eban Bisong on LinkedInSenvi.ai - senvi.aiWhat Smart CTOs Are Doing Differently With Offshore Teams in 2025Subscribe to the Global Talent SprintFull Scale – Build your dev team quickly and affordablyIf you’re trying to get your team out of the basement and into real product ownership, this episode is your playbook. Stop being a ticket factory. Build teams that think, create, and lead.Follow the show, rate it, and send this to someone who’s still trying to do “real Scrum.” They need it more than you do.
Transcribe →AI, Protein, and GLP-1s: What's Actually Working in Health Tech
Jun 1800:29:12Tap to summarizeMost people are already asking AI about their health. Almost none of them believe the answers. Around 40% use it to make wellness choices, but fewer than 5% trust what it says. Matt Watson and Josh Anthony, CEO of Nlumn, dig into why.Josh has spent 25 years in food and nutrition, and his take is blunt: trust drops fast as the question gets serious, from a recipe to a diagnosis, and the fix isn't a smarter chatbot. It's pairing the data with a human people actually trust. They cover what's real right now too. The protein obsession. Beans having a moment. GLP-1s and why weight loss is now about saving muscle, not just dropping fat. Why people are building their own messy personalization stacks because no single company does it well.Matt also explains why he flat out ignores his doctors on cholesterol, and he and Josh go a few rounds on whether ultra-processed food is the problem or a missed opportunity.If you build or invest in health products, listen now. And if you want help with personalized nutrition, reach Josh@nlumn.com or info@nlumn.com.⏱️ Episode Breakdown00:28 Introduction to Health Tech and AI03:36 Trust in AI for Health and Nutrition06:29 Personalization in Health and Nutrition09:26 Emerging Trends in Health Tech12:23 The Role of GLP-1 in Weight Management15:29 Challenges in the Food Industry18:37 Innovative Products in Health and NutritionLinks & ResourcesConnect with Joshua Anthony on LinkedInNlumn Website - https://www.nlumn.com/Email - mailto: info@nlumn.comWhat Smart CTOs Are Doing Differently With Offshore Teams in 2025Subscribe to the Global Talent SprintFull Scale – Build your dev team quickly and affordablyIf you’re trying to get your team out of the basement and into real product ownership, this episode is your playbook. Stop being a ticket factory. Build teams that think, create, and lead.
Transcribe →Building Software Solo with Beth Epperson of Legacy Purposed
Jun 1100:31:47Tap to summarizeMatt Watson sits down with Beth Epperson, founder and CEO of Legacy Purposed, here in the Kansas City area. Beth came up through marketing and branding, including the brand launch for Hyvee Arena, before deciding to build something of her own.Her company is built around two products. Aligned Legacy measures how people think in real time and helps teams see how aware, connected, and aligned they actually are. HIKMET, or Wisdom Illuminated, keeps a company's knowledge governed and accurate so nothing walks out the door when an employee leaves.Beth and Matt get into the messy reality of being a founder. She self-funded the whole thing, learned to code her own prototype, and pitched for over a year through a pile of rejections. She also walked away from a paid pilot because the people on the other side were not aligned on ethics and accountability.Matt shares why he thinks Beth represents a new kind of founder. Sales first, build second, now that AI can help build the thing. They also dig into validating an idea, the pull you want to feel from customers, and why getting your first case studies is the hardest part.If you have ever tried to get a product to market on your own, this one is for you.⏱️ Episode Breakdown00:38 Introduction to Legacy Purposed and Beth Epperson03:37 Beth's Entrepreneurial Journey and Corporate Experiences06:37 The Birth of Legacy Purposed and Its Mission09:52 Understanding Emotions and Accountability in the Workplace12:35 The Development of Innovative Tools for Corporate Growth15:38 Challenges in Building and Marketing the Software18:28 The Importance of Case Studies and Market Validation21:37 Future Aspirations and Closing ThoughtsLinks & ResourcesConnect with Beth Epperson on LinkedInLegacy Purposed Website - https://legacypurposed.com/Email - mailto:Beth@legacypurposed.comWhat Smart CTOs Are Doing Differently With Offshore Teams in 2025Subscribe to the Global Talent SprintFull Scale – Build your dev team quickly and affordablyIf you’re trying to get your team out of the basement and into real product ownership, this episode is your playbook. Stop being a ticket factory. Build teams that think, create, and lead.Follow the show, rate it, and send this to someone who’s still trying to do “real Scrum.” They need it more than you do.
Transcribe →Geothermal Energy and the Future of Data Center Power
Jun 400:24:35Tap to summarizeData centers are multiplying fast, and the energy demands are staggering. Matt Watson sits down with Tim Tarver, founder and CEO of Exceed Geo Energy, to talk about one of the most underrated power sources in the conversation: geothermal. Tim breaks down how his company is adapting drilling technology from the oil and gas industry to generate clean, baseload energy almost anywhere in the country, why geothermal outlasts solar and wind by decades, and how it could be the right fit for the next wave of AI infrastructure.If you're watching energy costs climb and wondering where the power for all these data centers is actually going to come from, this one's worth your time.Listen now and learn why geothermal might be the energy answer nobody's talking about enough. And if you enjoyed this episode, leave us a review and subscribe so you never miss a conversation with the founders and operators building what's next.⏱️ Episode Breakdown00:44 Introduction to Data Centers and Energy Challenges03:40 Geothermal Energy: A Sustainable Solution06:33 The Role of Geothermal in Data Center Energy Needs09:41 Entrepreneurship in Geothermal Energy12:41 Water Usage and Cooling in Data Centers15:40 Cost Comparison: Geothermal vs. Other Energy Sources18:50 Technological Advances in Drilling and Geothermal Energy21:48 Future of Geothermal Energy and Closing ThoughtsLinks & ResourcesConnect with Tim Tarver on LinkedInExceed Geo Energy - http://www.exegeoenergy.comWhat Smart CTOs Are Doing Differently With Offshore Teams in 2025Subscribe to the Global Talent SprintFull Scale – Build your dev team quickly and affordablyIf you’re trying to get your team out of the basement and into real product ownership, this episode is your playbook. Stop being a ticket factory. Build teams that think, create, and lead.Follow the show, rate it, and send this to someone who’s still trying to do “real Scrum.” They need it more than you do.
Transcribe →From Excel Sheet to 13,000 Customers: How Sean Tepper Built Tykr
May 2800:28:14Tap to summarizeMost retail investors don't know what to do after they open a brokerage account. Sean Tepper was one of them until he built a traffic light rating system for stocks and turned it into a SaaS platform used by 13,000 customers across 50 countries.In this episode of Startup Hustle, Matt Watson sits down with Sean Tepper, founder and CEO of Tykr, to break down the real story behind building a B2C SaaS product in a crowded fintech space.They get into why Warren Buffett and Charlie Munger inspired a process engineer to build a stock screener, how Tykr cuts through 100+ data points to give investors one simple signal, the broker API nightmare that nearly broke their best feature, and why onboarding is harder than the product itself. Sean also gets honest about the hiring mistake he made for years—and what finally changed.If you're building a self-serve SaaS product or trying to find your footing as a solo founder, this one's worth your time. Tune in to Startup Hustle now.⏱️ Episode Breakdown00:41 Introduction to Ticker and Sean Tepper03:31 The Journey of Building Ticker07:04 Understanding the Stock Market and Investment Strategies11:09 Building Trust and Confidence in Investment Decisions21:31 Acquisition Strategies and Metrics for Success16:21 The Impact of AI on Investment Platforms19:41 Challenges in Building a High-Tech Investment Platform22:11 Key Lessons Learned in Entrepreneurship25:33 Final Thoughts and Team DynamicsLinks & ResourcesConnect with Sean Tepper on LinkedInWhat Smart CTOs Are Doing Differently With Offshore Teams in 2025Subscribe to the Global Talent SprintFull Scale – Build your dev team quickly and affordablyIf you’re trying to get your team out of the basement and into real product ownership, this episode is your playbook. Stop being a ticket factory. Build teams that think, create, and lead.Follow the show, rate it, and send this to someone who’s still trying to do “real Scrum.” They need it more than you do.
Transcribe →Eric Ries: Why Good Companies Go Bad
May 2100:36:06Tap to summarizeEric Ries wrote The Lean Startup. Sold 2 million copies. Helped hundreds of people build companies from nothing. Now he's back with a harder question: why do so many of those companies eventually go bad?In this episode, Matt Watson sits down with Eric to talk about his new book Incorruptible—a deep dive into the invisible forces that corrupt organizations, why profit-maximization becomes pathological, and what it actually takes to build a company that stays great.They get into why the stage-gate development model keeps failing founders, the story of Saul Price and how Costco was born from a betrayal, and what a real fiduciary duty to your customer looks like in practice. Plus, how to structure your company so your values outlast you.Listen to the full episode on Startup Hustle. And if Incorruptible sounds like your next read, pre-order it at incorruptible.co before May 26th.⏱️ Episode Breakdown00:37 Introduction to Eric Ries and The Lean Startup06:57 The Journey to Incorruptible: A New Perspective12:38 The Challenge of Short-Term Thinking in Business16:14 Understanding Corruption in Business Practices22:51 Building Trustworthy Organizations31:03 Who Should Read Incorruptible?Links & ResourcesConnect with Eric Ries on LinkedInWhat Smart CTOs Are Doing Differently With Offshore Teams in 2025Subscribe to the Global Talent SprintFull Scale – Build your dev team quickly and affordablyIf you’re trying to get your team out of the basement and into real product ownership, this episode is your playbook. Stop being a ticket factory. Build teams that think, create, and lead.Follow the show, rate it, and send this to someone who’s still trying to do “real Scrum.” They need it more than you do.
Transcribe →The Non-Technical Founder Who Beat the Developers
May 700:35:39Tap to summarizeMost founders get the order wrong. They build for two years, then ask a marketer how to sell it. Connie Lund flipped the script. She started Zaboom with no dev team, no code background, and no VC funding. What she had was 50+ years of combined marketing and product experience, a GoHighLevel account, and a willingness to break things at 2 a.m. on a Sunday. In this episode, Connie walks Matt through how she built a working voice AI product for insurance agencies—using N8N, GoHighLevel, and Claude as her "CTO." Then landed paying customers in under 90 days. She also gets honest about what AI can't do for you: use good judgment, know when to stop, and figure out if what you're building actually matters to anyone. They cover the difference between outputs and outcomes, why talking to customers beats building in isolation every time, and how the traditional "raise VC, hire devs, ship product" playbook is getting replaced by something scrappier and faster. If you're a founder who's been waiting until the product is perfect to talk to people, this episode will make you uncomfortable. Good. Listen to this Startup Hustle episode now.⏱️ Episode Breakdown00:49 Introduction to Connie Lunn and Zaboom02:33 The Journey of Building Zaboom05:41 Tech Stack and Tools Used11:58 Prototype vs. Final Product16:16 Marketing and Customer Engagement21:09 Coaching and Helping Others25:31 Democratizing Technology and Skills32:08 Final Thoughts and AdviceLinks & ResourcesConnect with Connie Lund on LinkedInWhat Smart CTOs Are Doing Differently With Offshore Teams in 2025Subscribe to the Global Talent SprintFull Scale – Build your dev team quickly and affordablyIf you’re trying to get your team out of the basement and into real product ownership, this episode is your playbook. Stop being a ticket factory. Build teams that think, create, and lead.Follow the show, rate it, and send this to someone who’s still trying to do “real Scrum.” They need it more than you do.
Transcribe →Stop Hiding Behind Process (You Should Own the Product Instead)
Apr 2300:29:56Tap to summarizeMost product managers are just project managers with a fancier title. They make zero real decisions, answer to everyone, and wonder why nothing ships on time. Willis Jackson has been building product teams for over a decade. He's blacklisted entire companies from his hiring pool. And he moved to the Bay Area to measure himself against the best—only to find out nobody there really knows how to do product either. In this episode, Willis and I get into why product thinking is now the most valuable skill in tech, why AI didn't solve the bottleneck problem (it exposed it), and what happens when engineers can build 10x faster but nobody knows what to build. We also get into his company Middle Mile—basically the Airbnb of e-commerce fulfillment—and why stay-at-home parents running micro-warehouses out of spare rooms might be the future of how your next Amazon package gets delivered. Fair warning: if you're a product manager who hasn't talked to a customer for two weeks, this episode is going to be uncomfortable. Hit follow so you never miss an episode of Startup Hustle.⏱️ Episode Breakdown00:35 Reconnecting and Early Influences03:27 The Challenges of Product Management06:34 The Role of AI in Product Development09:32 Understanding Risks in AI and Software Development12:34 Bottlenecks in Product Teams15:25 The Importance of People in Business18:17 Innovative Fulfillment Solutions21:39 The Journey of Building a BusinessLinks & ResourcesConnect with Willis Jackson III on LinkedInWhat Smart CTOs Are Doing Differently With Offshore Teams in 2025Subscribe to the Global Talent SprintFull Scale – Build your dev team quickly and affordablyIf you’re trying to get your team out of the basement and into real product ownership, this episode is your playbook. Stop being a ticket factory. Build teams that think, create, and lead.Follow the show, rate it, and send this to someone who’s still trying to do “real Scrum.” They need it more than you do.
Transcribe →