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.
34episodes
Episodes
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From Excel Sheet to 13,000 Customers: How Sean Tepper Built Tykr
1w ago00:28:14Tap 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
2w ago00:36:06Tap 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
4w ago00:35:39Tap 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 →The Secret to Winning Venture Capital: What 2,000 Startup Investments Taught Dave Lambert
Apr 1600:34:11Tap to summarizeMost founders think investors bet on ideas. They don't.Dave Lambert has funded over 2,000 companies through RightSide Capital, and he's seen this pattern play out thousands of times. Great product. No revenue traction. Wrong ask, wrong timing. Automatic no.In this episode of Startup Hustle, Matt sits down with Dave to break down how RightSide Capital evaluates startups differently than traditional VCs. No subjective analysis. No months of diligence. Just data, profiles, and a decision in about a week.They get into how AI is changing the startup game, not just for building products faster, but for every operational aspect of running an early-stage company. And why sales is still the one thing that isn't getting easier anytime soon.Plus, the real talk on founder-market fit, why being slightly delusional might actually help, and what it takes to walk away with a check from an investor who's seen everything.If you're a technical founder who knows how to build but has no idea how to sell, this episode is for you.⏱️ Episode Breakdown00:26 Introduction to Venture Capital and Startups03:36 The Importance of Sales and Marketing in Startups06:24 Data-Driven Investment Strategies09:23 The Impact of AI on Startup Opportunities12:23 Operational Efficiency and Cost Reduction through AI15:28 Sales and Marketing Challenges for Startups18:31 Support and Resources for Portfolio Companies21:25 Evaluating Founders and Market Fit24:28 The Role of Delusion in EntrepreneurshipLinks & ResourcesConnect with Dave Lambert 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.Right Side Capital Management - https://www.rightsidecapital.com/
Transcribe →Are Software Engineers Really at Risk? Mohan Reddy Weighs In
Apr 900:25:46Tap to summarizeMatt Watson sits down with Mohan Reddy, serial entrepreneur and Chief Scientist at Cornerstone AI Labs, to explore how AI is fundamentally reshaping the way we think about work, skills, and human potential. Mohan shares the origin story of Skyhive—a workforce intelligence platform built to reskill and upskill people at a global scale—and how its acquisition by Cornerstone brought that mission to a larger stage.The conversation digs into why AI doesn't eliminate skills but transforms them, the distinction between tasks that can be automated versus those that require human judgment, and why "vibe coding" is both a breakthrough and a danger. Mohan also makes the case for reverse engineering as the most critical skill in an AI-driven world, and why sandbox environments will be essential for building trust in AI-assisted workflows.Whether you're a founder, engineer, or business leader trying to navigate the AI transition, this episode offers a grounded, optimistic perspective from someone who has spent decades at the intersection of human potential and machine intelligence.If you enjoyed today's episode, subscribe to the Starter Hustle podcast and leave us a review!⏱️ Episode Breakdown00:30 The Journey of Mohan Reddy and Skyhive03:34 Transition to Cornerstone AI Labs06:22 AI's Impact on Skills and Workforce09:33 The Evolution of Software Engineering12:29 The Future of Coding and AI Collaboration15:33 Upskilling in the Age of AI18:30 Curiosity and Learning in Tech21:34 Final Thoughts and AdviceLinks & ResourcesConnect with Mohan Reddy 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 →How AI Is Disrupting Education with Katie Boody Adorno of LeanLab Education
Apr 200:28:55Tap to summarizeAI is changing how kids learn. But are schools ready?Katie Boody Adorno is the founder and CEO of LeanLab Education. She's spent 13 years trying to close the opportunity gap in public education. In this episode, she and Matt break down how COVID widened learning disparities, why high-dosage tutoring works but doesn't scale, and how AI is now lowering that cost. They also get into what it takes to prepare kids for a world where AI handles most of the knowledge work.Listen to the full episode now! Subscribe to Startup Hustle wherever you get your podcasts.⏱️ Episode Breakdown00:00 The Genesis of Lean Lab Education05:25 Innovative Approaches to Educational Challenges09:08 The Impact of the Pandemic on Education11:32 Funding and Sustainability in Education12:58 The Role of Technology in Learning18:12 The Importance of Human Connection in Education20:12 Rethinking the Purpose of Education25:30 The Future of Higher Education and AILinks & ResourcesConnect with Katie Boody Adorno on LinkedInWhat Smart CTOs Are Doing Differently With Offshore Teams in 2025Subscribe to the Global Talent SprintFull Scale – Build your dev team quickly and affordablyLean Lab Education - https://leanlabeducation.org
Transcribe →AI Isn't Killing Software Jobs: It's Changing Who Builds What
Mar 2600:35:33Tap to summarizeZach Klempf is back! He joined Matt Watson on one of the early episodes of the show. Now, Zach is president of AutoManager, a private equity group with five automotive software companies under its umbrella.In this episode, Zach and Matt get into how AI is making senior engineers more productive. They talk about why offshore teams tend to adopt it more slowly, and where vibe coding breaks down when you're running production software with real integrations. They also get into why simple SaaS products are getting harder to defend. And why leads and sales have always been the harder problem anyway.Listen to the full episode now! Subscribe to Startup Hustle wherever you get your podcasts.⏱️ Episode Breakdown00:00 Introduction to Zach Klempf and AutoManager03:09 The Journey of Selle Automotive05:48 Outsourcing and Global Talent Strategy08:59 Experiences in Jamaica and the Philippines12:01 Transition to AutoManager and AI Integration15:13 AI Adoption and Team Dynamics18:02 The Future of Software Development and AI21:02 Challenges in AI Implementation24:10 Market Dynamics and Competitive Landscape26:53 Final Thoughts and ReflectionsLinks & ResourcesConnect with Zach Klempf on LinkedInhttps://www.automanager.com/What 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 Personal Tragedy to Healthcare Innovation
Mar 1200:26:17Tap to summarizeIn this episode, entrepreneur Chris Jones shares his journey from personal tragedy to building MatchRite Care, a healthcare data integration platform. He discusses product-market fit, scaling strategies, and the importance of community and continuous learning in entrepreneurship.⏱️ Episode Breakdown00:00 The Entrepreneurial Journey Begins02:54 The Birth of MatchRite Care06:07 Navigating Product Fit and Market Strategy09:04 The Importance of Data Sharing in Healthcare12:01 Scaling vs. Selling: The Business Model Dilemma15:08 Consulting and Mentorship in the Entrepreneurial Space17:45 The Value of Lifelong Learning and Community Support20:48 Reflections on the Entrepreneurial JourneyLinks & ResourcesConnect with Chris Jones 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 →Matt & Mark Roberge
Mar 500:37:46Tap to summarizeIn this episode of Startup Hustle, Matt Watson interviews Mark Roberge, a former HubSpot executive and current venture capitalist, about his journey from engineering to sales and the importance of scaling startups. Mark discusses the genesis of HubSpot, the significance of sales in startups, and the concept of product-market fit. He emphasizes the need for customer research, avoiding false positives in feedback, and identifying the ideal customer profile. Mark also shares insights on scaling strategies, key metrics for success, and the science behind scaling businesses effectively.⏱️ Episode Breakdown00:00 The Genesis of HubSpot02:56 Transitioning from Engineering to Sales06:06 The Science of Scaling08:53 The Importance of Selling Early12:12 Understanding Customer Needs14:58 Avoiding False Positives in Feedback15:39 Design Partner Dilemma18:21 Target Audience Insights19:56 Ideal Customer Profile Framework23:00 The Science of Scaling25:05 Understanding Growth Investment30:55 Navigating Growth Challenges35:25 Final Thoughts on Scaling SuccessTAKEAWAYSSales is crucial for startup success.Understanding product-market fit is essential before scaling.Customer research should start at the ideation stage.Avoid false positives by validating customer interest.Identify your ideal customer profile to focus efforts.Scaling should be approached methodically and strategically.Establish leading indicators of customer retention.Sales methodologies must evolve as the company grows.Demand generation must align with growth aspirations.The science of scaling involves data-driven decision making.Links & ResourcesConnect with Mark Roberge 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.
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