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1380 episodes
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Date created
2017/12/09
Latest episode
2026/10/01
Average duration
32 min.
Release period
12 days
Description
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.
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Building the Ramp of the Philippines: Fintech for the Underbanked
2026/10/01
"There are eight digital banks trying to build the Chime of the Philippines. No one's building the Ramp or the Brex. That's the opportunity."
I talked with Zach Marks, founder and CEO of Jia, on Startup Hustle this week. Jia is building modern digital banking for small businesses in emerging markets, starting in the Philippines, powered by an AI credit engine that turns messy, handwritten paperwork into an underwriting decision in minutes instead of weeks.
Here's what you'll get out of it:
⚡ Why small businesses in emerging markets are so underserved, and why banks there take zero risk while asking founders to put their house up as collateral
⚡ How Zach went from teaching English and befriending samosa vendors in India to launching fintech markets across 15+ countries
⚡ How Jia's AI credit engine cuts a three-week manual underwriting file down to minutes, with a low non-performing loan rate
⚡ The real story of doing business in the Philippines, from BIR shakedowns to why the best local talent still beats every other emerging market
⚡ Why building a strong local culture and hiring leaders who embody it matters more than anything when you hire abroad
If you're building in fintech, emerging markets, or with an offshore team, this one is worth your time.
Listen to the Startup Hustle podcast anywhere you listen to podcasts!
⏱️ Episode Breakdown
01:16 Introduction and Guest Background
02:20 Starting in Construction and Key Clients
03:24 The Inspiration Behind the Book
04:23 Early Life Challenges and Lessons Learned
07:03 Common Entrepreneurial Traits and Backgrounds
09:38 Key Lessons from the Book
10:27 Business Lessons for Tech Entrepreneurs
11:55 Impact of AI on Construction and Design
13:50 Acquiring Big Name Clients and Referrals
16:24 Building a Scalable Business Model
18:24 The Power of Case Studies and Content Marketing
20:05 Showcasing Work Through Content and Videos
24:00 Final Advice and Closing Remarks
Links & ResourcesConnect with Zach Marks on LinkedIn
Jia - https://jia.xyz/
Full Scale – Build your dev team quickly and affordably
If 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.
Unlock working capital with Jia
Nothing to Lose: What Really Drives Entrepreneurs
2026/08/20
"There's no magical growth lever. You just do a good job, every day, for 23 years, and the referrals do the rest."
I talked with Matt Watts, founder of MWA Projects and author of Made With Ambition, on Startup Hustle this week. Matt designs and builds some of the most striking commercial spaces in the world, from Jimmy Choo's London HQ to Nike showrooms, Net-a-Porter, and a new lounge for Netflix.
Here's what you'll get out of it:
⚡ Why there's no magic growth lever, and how one great job snowballed into Nike, Hermès, ASOS, and Stella McCartney through pure referral
⚡ How a difficult childhood and a bitter divorce shaped the risk appetite so many entrepreneurs share, playing not to lose instead of playing to win
⚡ The AI horror story where a tool invented 10 years of Harrods experience for his head of facilities "because it thought it sounded better"
⚡ Why case studies are the mistake too many founders skip, and how showing beats telling in a visual business
⚡ Why the CEO has to drive the marketing, and why "TikTok next week" is now on the agenda
⏱️ Episode Breakdown
00:48 Introduction and Guest Background
01:52 Starting in Construction and Key Clients
03:18 The Inspiration Behind the Book
03:55 Early Life Challenges and Lessons Learned
06:35 Common Entrepreneurial Traits and Backgrounds
09:09 Key Lessons from the Book
09:59 Business Lessons for Tech Entrepreneurs
11:27 Impact of AI on Construction and Design
13:22 Acquiring Big Name Clients and Referrals
15:56 Building a Scalable Business Model
17:56 The Power of Case Studies and Content Marketing
19:37 Showcasing Work Through Content and Videos
23:32 Final Advice and Closing Remarks
Links & ResourcesConnect with Matt Watts on LinkedIn
Website: MWA Projects
What Smart CTOs Are Doing Differently With Offshore Teams in 2025
Subscribe to the Global Talent Sprint
Full Scale – Build your dev team quickly and affordably
If you're building a business the slow, durable way, this one is worth your time.
Listen to the Startup Hustle podcast anywhere you listen to podcasts!
The 2026 State of IT Staffing: Trends in Hiring, AI, and Offshore
2026/08/13
"Both things are true. Software jobs are projected to grow 15%, and 74% of employers say they can't fill the roles. That's the whole story of IT staffing in 2026."
This week on Startup Hustle, Matt Brown, Full Scale's head of marketing, put me in the guest chair to walk through our new State of IT Staffing report, a data-heavy look at where tech hiring actually stands heading into 2026.
Here's what you'll get out of it:
⚡ The 2026 paradox, why the field isn't shrinking but the entry ramp into it is breaking, with new-grad hiring down 65% at big tech
⚡ Why the job shifted from "engineering" back to "development," and why AI made product thinking the scarce skill
⚡ Why AI sped up the typing but left the judgment exactly as hard, so the value moved to senior people
⚡ Why retention is the number the industry can't fake, and why AI turned it from nice-to-have into the whole game
⚡ Why software has never been cheaper to build, and why that's a reason to build more, not cut
If you're hiring engineers, leading a team, or building a career in software, this one is worth your time.
⏱️ Episode Breakdown
00:33 Introduction and overview of the episode
02:39 Full scale's employee satisfaction and recognition
05:30 The impact of AI on software development roles
10:40 The 2026 paradox: job growth vs. role filling
15:35 The importance of product thinking and customer feedback
20:36 Decoupling headcount from output with AI
25:21 Remote work, location independence, and cultural shifts
30:37 Running engineering teams in 2026 and beyond
35:35 The need for strategic focus and organizational agility
40:37 Conclusion and key takeaways from the episode
Links & Resources
Read the full report - [https://fullscale.io/blog/state-of-it-staffing/
Full Scale(https://fullscale.io/blog/state-of-it-staffing) – Build your dev team quickly and affordably
What Smart CTOs Are Doing Differently With Offshore Teams in 2025
Subscribe to the Global Talent Sprint
If 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.
Why AI Made Software Engineers More Human
2026/08/06
"AI scribes are just a feature. The record of clinical judgment is the moat."
I talked with Kush Shah, founder and CEO of Noted Dent, on Startup Hustle this week. Noted Dent uses AI to handle clinical documentation for dentists, so practitioners aren't stuck writing notes at 11pm or on the weekend, and so they're covered when the auditors and health funds come knocking.
Here's what you'll get out of it:
⚡ Why vibe coding gets you to an MVP and no further, and why Kush deleted 8,000 lines of AI-generated code in three months
⚡ Why the job of a software engineer has changed, and how AI has actually made it more human
⚡ Why demand, not product, is the hardest thing in any business, even eight years in
⚡ Why startups are the best place for young engineers to learn, and why job-title silos hold them back
⚡ What actually makes the leap to CEO so hard when you come from a technical background
If you're a technical founder, an engineer eyeing your next move, or anyone building in a regulated space, this one is worth your time.
Listen to the Startup Hustle podcast anywhere you listen to podcasts!
⏱️ Episode Breakdown
01:06 Introduction and Anthony Jackson's background
02:47 Is software development dead again?
03:48 The impact of AI on coding and human judgment
04:41 The importance of responsibility in software development
06:33 The challenge of product management and customer feedback
10:52 Transitioning from individual contributor to manager
12:00 Building effective teams and leadership culture
15:14 Anthony Jackson's leadership OS book and approach
19:00 The significance of company and team culture
21:41 The impact of good and bad managers
22:06 Anthony Jackson's newsletter and coaching
23:48 Connecting software developers with customers
25:40 Empathy for users and understanding their experience
29:06 Where to find Anthony Jackson's resources and books
Links & ResourcesConnect with Kush Shah on LinkedIn - https://www.linkedin.com/in/kush-shah-kush/
Noted Dent - https://noteddent.com/
What Smart CTOs Are Doing Differently With Offshore Teams in 2025
Subscribe to the Global Talent Sprint
Full Scale – Build your dev team quickly and affordably
If 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.
LeadershipOS Decoded: Building Teams That Run Without You in the Room
2026/07/30
"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 Breakdown
00:32 Introduction and Anthony Jackson's background
02:13 Is software development dead again?
03:14 The impact of AI on coding and human judgment
04:07 The importance of responsibility in software development
05:59 The challenge of product management and customer feedback
10:18 Transitioning from individual contributor to manager
11:36 Building effective teams and leadership culture
14:41 Anthony Jackson's leadership OS book and approach
18:26 The significance of company and team culture
21:07 The impact of good and bad managers
21:38 Anthony Jackson's newsletter and coaching
23:14 Connecting software developers with customers
25:06 Empathy for users and understanding their experience
28:18 Where to find Anthony Jackson's resources and books
Links & ResourcesConnect with Anthony Jackson on LinkedIn
Anthony Jackson's Website - https://technicaleader.coach
What Smart CTOs Are Doing Differently With Offshore Teams in 2025
Subscribe to the Global Talent Sprint
Full Scale – Build your dev team quickly and affordably
If 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.
It's Not About the Code. It's About the Problem.
2026/07/23
I 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 Breakdown
00:42 Introduction to Adrian Gutierrez and Ledger
01:04 Adrian's background in FinTech and PropTech
00:49 The origin story of Ledgre and market gaps
02:54 How AI is transforming property management tools
04:11 Adrian's experience owning rental properties
05:18 The importance of domain knowledge in product development
06:18 Manual bookkeeping and workflow complexity
07:15 Scaling wisely and understanding problems before automating
08:24 The importance of iteration and customer feedback
08:52 Challenges of outreach and building relationships
10:16 Cold outreach and response rates
11:03 The impact of AI on distribution and problem-solving
12:10 AI exposing weaknesses in traditional software development
13:36 Reviving software engineering practices with AI
14:32 Shift in marketing and distribution roles
15:55 Using AI for marketing and SEO automation
17:22 AI's role in software development and team management
21:10 Living as a digital nomad and its impact on business
22:45 Traveling and understanding global fintech landscapes
24:33 Financial and payment infrastructure differences worldwide
25:13 The value of solving real problems in different markets
25:48 How to learn more about Ledger and Adrian
If 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 & Resources
Connect with Adrian Gutierrez on LinkedIn - https://www.linkedin.com/in/adrian--gutierrez/
Ledgre Website - https://www.ledgre.ai/
The Speed of Context: Why AI Changed What Engineers Actually Do
2026/06/25
Most 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 Breakdown
00:42 From Founding Engineer to Solo Founder
01:52 Using AI as an Engineering Leader
03:24 Building RTD2: An AI Teammate for Support
05:27 The Speed of Context, Not Code
06:11 Why You Should Record Everything
08:59 Winning Over AI-Skeptical Engineers
11:50 The AI Spectrum Across 80 Clients
13:35 A Bad Time to Be a Coder, a Great Time to Build
14:03 Why "Good Enough" Is Good Enough
14:52 Human-in-the-Loop and Reviewing AI's Work
16:28 Going All-In on Senvi
19:01 Validating the Product With a Beta Group
21:01 Bootstrapping a Truly AI-Native Company
Links & ResourcesConnect with Eban Bisong on LinkedIn
Senvi.ai - senvi.ai
What Smart CTOs Are Doing Differently With Offshore Teams in 2025
Subscribe to the Global Talent Sprint
Full Scale – Build your dev team quickly and affordably
If 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.
AI, Protein, and GLP-1s: What's Actually Working in Health Tech
2026/06/18
Most 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 [email protected] or [email protected].
⏱️ Episode Breakdown
00:28 Introduction to Health Tech and AI
03:36 Trust in AI for Health and Nutrition
06:29 Personalization in Health and Nutrition
09:26 Emerging Trends in Health Tech
12:23 The Role of GLP-1 in Weight Management
15:29 Challenges in the Food Industry
18:37 Innovative Products in Health and Nutrition
Links & ResourcesConnect with Joshua Anthony on LinkedIn
Nlumn Website - https://www.nlumn.com/
Email - mailto: [email protected]
What Smart CTOs Are Doing Differently With Offshore Teams in 2025
Subscribe to the Global Talent Sprint
Full Scale – Build your dev team quickly and affordably
If 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.
Building Software Solo with Beth Epperson of Legacy Purposed
2026/06/11
Matt 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 Breakdown
00:38 Introduction to Legacy Purposed and Beth Epperson
03:37 Beth's Entrepreneurial Journey and Corporate Experiences
06:37 The Birth of Legacy Purposed and Its Mission
09:52 Understanding Emotions and Accountability in the Workplace
12:35 The Development of Innovative Tools for Corporate Growth
15:38 Challenges in Building and Marketing the Software
18:28 The Importance of Case Studies and Market Validation
21:37 Future Aspirations and Closing Thoughts
Links & ResourcesConnect with Beth Epperson on LinkedIn
Legacy Purposed Website - https://legacypurposed.com/
Email - mailto:[email protected]
What Smart CTOs Are Doing Differently With Offshore Teams in 2025
Subscribe to the Global Talent Sprint
Full Scale – Build your dev team quickly and affordably
If 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.
Geothermal Energy and the Future of Data Center Power
2026/06/04
Data 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 Breakdown
00:44 Introduction to Data Centers and Energy Challenges
03:40 Geothermal Energy: A Sustainable Solution
06:33 The Role of Geothermal in Data Center Energy Needs
09:41 Entrepreneurship in Geothermal Energy
12:41 Water Usage and Cooling in Data Centers
15:40 Cost Comparison: Geothermal vs. Other Energy Sources
18:50 Technological Advances in Drilling and Geothermal Energy
21:48 Future of Geothermal Energy and Closing Thoughts
Links & ResourcesConnect with Tim Tarver on LinkedIn
Exceed Geo Energy - http://www.exegeoenergy.com
What Smart CTOs Are Doing Differently With Offshore Teams in 2025
Subscribe to the Global Talent Sprint
Full Scale – Build your dev team quickly and affordably
If 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.
From Excel Sheet to 13,000 Customers: How Sean Tepper Built Tykr
2026/05/28
Most 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 Breakdown
00:41 Introduction to Ticker and Sean Tepper
03:31 The Journey of Building Ticker
07:04 Understanding the Stock Market and Investment Strategies
11:09 Building Trust and Confidence in Investment Decisions
21:31 Acquisition Strategies and Metrics for Success
16:21 The Impact of AI on Investment Platforms
19:41 Challenges in Building a High-Tech Investment Platform
22:11 Key Lessons Learned in Entrepreneurship
25:33 Final Thoughts and Team Dynamics
Links & ResourcesConnect with Sean Tepper on LinkedIn
What Smart CTOs Are Doing Differently With Offshore Teams in 2025
Subscribe to the Global Talent Sprint
Full Scale – Build your dev team quickly and affordably
If 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.
Eric Ries: Why Good Companies Go Bad
2026/05/21
Eric 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 Breakdown
00:37 Introduction to Eric Ries and The Lean Startup
06:57 The Journey to Incorruptible: A New Perspective
12:38 The Challenge of Short-Term Thinking in Business
16:14 Understanding Corruption in Business Practices
22:51 Building Trustworthy Organizations
31:03 Who Should Read Incorruptible?
Links & ResourcesConnect with Eric Ries on LinkedIn
What Smart CTOs Are Doing Differently With Offshore Teams in 2025
Subscribe to the Global Talent Sprint
Full Scale – Build your dev team quickly and affordably
If 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.
The Non-Technical Founder Who Beat the Developers
2026/05/07
Most 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 Zaboom
02:33 The Journey of Building Zaboom
05:41 Tech Stack and Tools Used
11:58 Prototype vs. Final Product
16:16 Marketing and Customer Engagement
21:09 Coaching and Helping Others
25:31 Democratizing Technology and Skills
32:08 Final Thoughts and Advice
Links & ResourcesConnect with Connie Lund on LinkedIn
What Smart CTOs Are Doing Differently With Offshore Teams in 2025
Subscribe to the Global Talent Sprint
Full Scale – Build your dev team quickly and affordably
If 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.
Stop Hiding Behind Process (You Should Own the Product Instead)
2026/04/23
Most 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 Breakdown
00:35 Reconnecting and Early Influences
03:27 The Challenges of Product Management
06:34 The Role of AI in Product Development
09:32 Understanding Risks in AI and Software Development
12:34 Bottlenecks in Product Teams
15:25 The Importance of People in Business
18:17 Innovative Fulfillment Solutions
21:39 The Journey of Building a Business
Links & ResourcesConnect with Willis Jackson III on LinkedIn
What Smart CTOs Are Doing Differently With Offshore Teams in 2025
Subscribe to the Global Talent Sprint
Full Scale – Build your dev team quickly and affordably
If 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.
The Secret to Winning Venture Capital: What 2,000 Startup Investments Taught Dave Lambert
2026/04/16
Most 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 Breakdown
00:26 Introduction to Venture Capital and Startups
03:36 The Importance of Sales and Marketing in Startups
06:24 Data-Driven Investment Strategies
09:23 The Impact of AI on Startup Opportunities
12:23 Operational Efficiency and Cost Reduction through AI
15:28 Sales and Marketing Challenges for Startups
18:31 Support and Resources for Portfolio Companies
21:25 Evaluating Founders and Market Fit
24:28 The Role of Delusion in Entrepreneurship
Links & ResourcesConnect with Dave Lambert on LinkedIn
What Smart CTOs Are Doing Differently With Offshore Teams in 2025
Subscribe to the Global Talent Sprint
Full Scale – Build your dev team quickly and affordably
If 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/
Podcast reviews
Read Startup Hustle podcast reviews
Gotchayeah 2023/03/31
👀
Good podcast but needs better cover art
Dan in KC 2022/12/30
Love it!
Love these folks! Rotating host is a pretty unique idea. Fun to get to know the hosts and their speciality. Seems like that helps produce a ton of goo...
ASobering 2022/12/15
Top Tier!
This is one of the most insightful podcasts that I have ever come across! Startup Hustle does such a great job highlighting meaningful conversations w...
Dan1777999877 2022/12/15
A Must Listen🎧
Startup Hustle has quickly become a favorite in my feed! I'm consistently impressed by the engaging conversations, insightful content, and actionable ...
The Real KO 2022/10/11
A breath of fresh air
With SO many podcasts to choose from, making sure you pick one that is fun, informative and engaging is rare.
The Startup Hustle team has assembled ...
Tired of Hate Speech 2022/10/02
Matt is so obnoxious
I had to sit through an hour of this because I wanted info on STL tech scene. Ending up fast forwarding every time he was talking.
Fina💋❤️ 2022/09/23
Proud!
I am so proud of you. Love your piece aka peace! ❤️💋
Mario87 Medford 2022/07/27
🔥show for entrepreneurs at every stage of their biz
Highly recommend Startup hustle show. They really have topics for every step of your business.
The Machine Pun 2022/05/23
Love this show
This podcast is seriously amazing! So many great guests whose insights have been incredibly powerful in my career. If there is one podcast to checko...
ErmaTheLurker 2022/05/19
Fabulous Show
This show brings together the best conversations on engaging topics. Must listen!
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