Startup Hustle
Startup Hustle is a podcast for entrepreneurs, by entrepreneurs. It aims to tell the real story of startups and entrepreneurs, covering topics from funding to failure and beyond. The show is designed for anyone who wants to start, own, or build a business.
Episodes
The Speed of Context: Why AI Changed What Engineers Actually Do
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, sh
AI, Protein, and GLP-1s: What's Actually Working in Health Tech
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
Building Software Solo with Beth Epperson of Legacy Purposed
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 ac
Geothermal Energy and the Future of Data Center Power
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,
From Excel Sheet to 13,000 Customers: How Sean Tepper Built Tykr
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
Eric Ries: Why Good Companies Go Bad
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 pathologi
The Non-Technical Founder Who Beat the Developers
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
Stop Hiding Behind Process (You Should Own the Product Instead)
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 p
The Secret to Winning Venture Capital: What 2,000 Startup Investments Taught Dave Lambert
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
Are Software Engineers Really at Risk? Mohan Reddy Weighs In
Matt 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
How AI Is Disrupting Education with Katie Boody Adorno of LeanLab Education
AI 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
AI Isn't Killing Software Jobs: It's Changing Who Builds What
Zach 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
From Personal Tragedy to Healthcare Innovation
In 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 Fi
Matt & Mark Roberge
In 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 positiv
Revolutionizing Hiring with GitHired
In this episode of Startup Hustle, Matt Watson interviews Krishna Oza, founder and COO of Git Hired, discussing the challenges of hiring software engineers, particularly for startups. Krishna shares his personal experiences that led to the creation of GitHired, an AI-driven platform designed to help startups find the right technical talent based on proof of work. The conversation delves into the u
Harnessing AI for Business Success
In this episode of Startup Hustle, Matt Watson interviews John Morlan, founder and CEO of Smarter Risk, about the transformative impact of AI on startups. John shares his journey of integrating AI into his business, enhancing productivity, and improving collaboration with developers. He discusses the balance between product-led and sales-led growth strategies, the importance of knowledge managemen
Navigating Entrepreneurship: Insights from Matt Haycox
In this episode, Matt Watson interviews Matt Haycox, an experienced entrepreneur who shares insights from his 25 years in business, focusing on capital raising, the challenges of entering the tech space as a non-technical leader, and the impact of AI on business development. Haycox discusses his journey from traditional businesses to tech ventures, emphasizing the importance of understanding both
Creative Engineering at Scale What Big Companies Get Wrong and Right with David Mitchell
What happens when you mix creative agency chaos with world-class engineering? You get teams that don’t just write code—they own the product.In this episode, I’m talking with David Mitchell, CTO at VML, one of the biggest creative agencies on the planet. With thousands of engineers and global clients like Wendy’s and United Airlines, David’s teams are building things that most devs only dream of—an
Engineering Clarity in the Age of AI with Seth Rosenbauer
Engineering Clarity in the Age of AI: How Docs, Context, and Product Thinking Shape Better SoftwareSeth Rosenbauer is the founder of a tool that uses AI to help engineers create better documentation—and, more importantly, the right thing, faster.But this conversation isn’t just about tooling.It’s about how context is the new currency in engineering. Why your team’s ability to understand what to bu
Fixing the Language Barrier Between Engineers and Executives with Karell Ste Marie of The Serious CT
Matt is joined by Karell Ste-Marie, founder of The Serious CTO YouTube channel. Together, they tackle one of the biggest hidden challenges in software companies: the language and cultural barrier between engineers and executives.Karell and Matt break down why innovation is so rare in large organizations, why engineers and business leaders often talk past each other, and how the CTO role often beco
Prompt Prototyping, AI Vibes, and the New Rules of Product Management
Product management is being rewritten in real time, and AI is doing the editing.Matt sits down with Jerel Velarde, product manager at Full Scale Ventures, to discuss how AI is reshaping the relationship between PMs and engineering. We dive into what Jerel calls prompt prototyping, how expectations for product velocity have changed, and why the best PMs today are blending design, strategy, and code
Why Teams Lose Their Way at Scale with Randy Silver
Matt is joined by product and leadership consultant Randy Silver to unpack one of the most frustrating problems in product organizations: everyone knows where they want to go, but no one knows how to actually get there.Together they explore what causes this breakdown in execution, how companies drift from product strategy to dysfunction, and what strong leadership really looks like at scale.Key Di
How AI Is Really Impacting Developer Experience and the Real Productivity Problem with Laura Tacho
In this episode, Matt is joined by Laura Tacho, CTO at DX — one of the leading voices in developer experience research and tooling. Together, they unpack how AI is really affecting software development teams, why developer experience has a “marketing problem,” and why organizational friction — not technology — is the biggest productivity killer.If you’ve been wondering whe
Why We Still Need Software Engineers in the Age of AI with Brian Jenney
AI can scaffold an app in seconds, but can it refactor that thousand-line React file when the first bug hits production? In this episode, I sit down with Brian Jenney software engineer and program owner of the coding bootcamp Parsity, to draw a hard line between “code that runs” and “code that lasts.” From mentoring career-switchers to stress-testing AI in real-world pipelines,
Simple Systems that Let CTOs Delegate Ownership—and Still Sleep at Night with Brittany Rastsmith
If you’re running a startup, chances are you’re the bottleneck. Brittany Rastsmith joins Product Driven to talk through why founders constantly end up in this trap and how to escape it. She works with early-stage companies through her consulting firm, Bloom Remote, and she's seen it all. We get into how to create clarity, visibility, and accountability across your team so you’re not stuc
Technical Co-Founders are Startup Gold with Noah Lindner
The 10X Developer Decoded: Why Technical Co-Founders Are Startup Gold 💎In this revealing conversation, we unpack one of tech's most polarizing concepts while exploring the brutal realities of building technical partnerships in today's startup ecosystem. Host Matt Watson and Noah Lindner (ex-Airbnb engineer turned consultant) deliver unfiltered insights that challenge conventional wisdom about tech
CTO Levels and the Path to Strategic Tech Leadership with Kathy Keating
From Coding to Catalyst: The Evolution of Technology Leadership 🚀Journey through the transformation of modern CTOs with industry veteran Kathy Keating, who shares battle-tested insights from scaling teams of 2 to 450+ engineers. This episode unravels the complex tapestry of technology leadership, exploring how yesterday's code-focused roles have evolved into today's strategic business catalysts.🔗
Inside 'Product Driven': Why This New Book is Every Engineering Leader's Must-Read
Product Driven: Building Software Teams That Ship Value 🚀In this special book launch episode, we dive deep into the intersection of engineering leadership, product thinking, and the transformative impact of AI on software development. Join Matt Watson and Craig Ferril as they explore the revolutionary "Product Driven Model" and why traditional development approaches are becoming obsolete.🔗 Essenti
The Engineering Leadership Book That Actually Shows You How to Build Product-Minded Teams
Product Driven: The Book Launch - A Software Leader's Journey to Creating High-Performance Teams 📚After months of intensive writing and years of industry experience, Matt Watson unveils his groundbreaking book "Product Driven" - a comprehensive guide for engineering leaders seeking to build teams with a genuine product mindset. This isn't just another business book; it's a practical roadmap for tr
Rethinking Requirements When Engineers Are No Longer the Bottleneck with Chris Rickard
Breaking Through Requirements Hell: How AI is Revolutionizing Software Development 🚀In this compelling exploration of technological transformation, host Matt Watson connects with Chris Rickard, founder of UserDoc, broadcasting from Vietnam. Their conversation unveils a profound shift happening across the software industry—one where artificial intelligence is fundamentally reshaping the relationshi
How Boddle's Product-Driven Approach Built Educational Games That Kids Ask Parents to Buy with Clarence Tan
Learning Through Play: How Boddle Built Educational Games That Kids Actually WantIn this insightful conversation, Matt Watson talks with Clarence Tan, founder and CEO of Boddle Learning, about their journey building educational games that have reached over 10 million users. Clarence shares how they tackled the classic problem of educational games - how to make them as engaging as regular games whi
How Feedback Loops Transform Development Efficiency with Ashley Davis
Feedback-Driven Development: Optimizing Your Software Engineering ProcessIn this enlightening conversation with author Ashley Davis, Matt Watson explores the concept of feedback-driven development and how it shapes effective software engineering practices. Ashley, author of "Bootstrapping Microservices" and the upcoming "The Feedback-Driven Developer," shares valuable insights on how developers ca
Product-Led Growth vs. VC Funding: Lessons from 25 Bootstrapped Startups with John Rush
Bootstrapping vs VC: John Rush on Building 25 Successful Products 🚀In this enlightening episode of Product Driven, host Matt Watson sits down with serial tech entrepreneur John Rush. Known for his prominent presence on social media platforms like Twitter (X) and LinkedIn, John shares his journey from VC-backed companies to successfully bootstrapping 25 different startups over the past 15 years. Th
AI Adoption Strategies: Inspiring Developer Teams to Embrace Intelligent Tools with Senad Santic
AI and Agency Evolution: Navigating the Future of Software Development 🚀In this thought-provoking episode of Product Driven, Matt Watson welcomes Senad Santic, owner of Zendev software development agency and founder of LinkBound. They dive deep into how AI is reshaping software development agencies, training strategies for developers in this evolving landscape, and the challenges of diversifying f
Three Core Principles CTOs Use to Create an Engineering Culture that Inspires and Retains Top Talent with John Durrant
Building Human-Centric Engineering Teams: Culture, Motivation, & Purpose 🛠️In this episode of Product Driven, Matt Watson talks with John Durant, founder of Human Centric Engineering, about the critical elements that create high-performing engineering cultures. John explains how mastery, autonomy, and purpose form the foundation of intrinsic motivation for engineers and how courage enables tea
AI in QA Testing: How TestChimp is Revolutionizing Software Quality Assurance with Nuwan Samarasekera
🧪 The AI Testing Revolution: Reimagining QA in the Era of Generative IntelligenceIn this intellectually stimulating conversation, Matt Watson and Nuwan Samarasekera (Founder & CEO of TestChimp) explore the transformative impact of generative AI on software testing methodologies. As AI accelerates development cycles, discover why testing has emerged as the new bottleneck and how innovative
Solving the Hidden Challenges of Growing Engineering Teams at Scale with Gleb Braverman from HackerPulse
🔍 Engineering Visibility: Unlocking Team Performance at Scale with Hacker PulseIn this intellectually stimulating exploration, Matt Watson and Gleb Braverman (Founder & CEO of Hacker Pulse) delve into the universal challenges that emerge when engineering organizations reach critical mass. From identifying "ghost engineers" to optimizing team composition across time zones, discover why seemingl
How Full Scale Ventures Builds Product-Driven Startups with Craig Ferril
Full Scale Ventures Launches & The Power of Venture Studios 🚀In this transformative episode of Product Driven, host Matt Watson introduces his exciting new venture with Craig Ferril—Full Scale Ventures. They dive deep into the concept of venture studios, exploring various models and explaining why they've launched their own. The conversation reveals how their combined expertise in technology,
When Great CTOs Go Into Beast Mode with Ron Timoshenko
🦸♂️ Unlocking CTO Mode: When Technical Leaders Become Innovation HeroesIn this intellectually stimulating conversation, Matt Watson and Ron Timoshenko (CIO of Rimbull Health) unpack the multifaceted nature of the CTO role and explore the critical moments when technical leaders must activate their "beast mode" to drive innovation. Through candid discussion about leadership styles, technical debt,
The Best Startup Pitch Framework
In this episode, Matt Watson interviews Rajiv Nathan, the Startup Hype Man, who shares insights on how to pitch a startup to investors and customers effectively. Rajiv discusses his journey from a marketing background to becoming a pitch expert, emphasizing the importance of understanding the pitch landscape beyond just raising capital. He introduces the K-PASA formula for crafting elevator pitche
Targeting the Midmarket, Growing with SEO
In this episode, Matt Watson interviews Ben Taylor, founder and CEO of Soft Ledger, about his journey in creating accounting software. They discuss the challenges of building a product in a competitive market, the importance of identifying gaps in existing solutions, and the lessons learned from the startup experience. Ben shares insights on their go-to-market strategy, the role of AI in accountin
Starting vs Growing a Business
In this episode, Matt Watson and Sean Beckner discuss the journey of entrepreneurship, investment strategies, and the evolution of business growth. Sean shares his experiences transitioning from a startup founder to an investor, highlighting the importance of timing in business exits and the dynamics of customer engagement in the digital age. They explore the challenges and rewards of acquiring bu
Boutique VCs & The Effect of AI
In this episode, Matt Watson speaks with Joseph Ruscio, a partner at Heavybit, a venture capital firm focused on investing in software development-related companies. They discuss the evolving landscape of venture capital, the unique value niche VC firms provide, and the impact of AI on software development. Joseph shares insights on the challenges developers face, the importance of finding product
Scaling with Affordable Talent from the Philippines
In this episode, Matt Watson and Yoni Kozminski discuss the intricacies of hiring talent in the Philippines, exploring Yoni's journey from creative advertising to building a recruitment agency. They delve into the challenges of scaling a business, the importance of value creation in sales, and the need for clear job definitions and onboarding processes. The conversation highlights the evolving wo
Building Customer & Employee Trust
In this episode, Matt Watson interviews Andrew Plato, a seasoned entrepreneur and author of 'The Founder's User Manual.' They discuss the challenges of entrepreneurship, the importance of differentiation in a competitive market, and the role of trust and credibility in business. Andrew shares insights from his experiences, emphasizing the need for startups to establish a unique identity, navigate
Bootstrapping to $10M, The Future of Inbound Sales
Adam Robinson, founder and CEO of Retention, discusses his new product RB2B and the importance of simplicity and profitability in building a successful business. He emphasizes the value of bootstrapping and achieving $10 million ARR before considering raising funds. Adam challenges the traditional venture-backed model and highlights the benefits of owning a profitable business that generates milli
The Business of Virtual Assistants
Tyler Lieber, co-founder and CEO of Coconut VA, joins Matt Watson on the Startup Puzzle podcast to discuss the benefits and challenges of hiring virtual assistants (VAs) in the Philippines. They share their personal experiences with remote hiring and highlight the importance of trust and communication in working with VAs. Tyler explains that VAs can assist with a wide range of tasks, from email an
Startup Lawyer Advice, Future Impact of AI
In this episode, Matt Watson interviews Nimrod Vromen, author of Prompting Happiness, about the future of generative AI and its impact on various aspects of life. They discuss the role of lawyers in startups, the importance of focusing on distribution rather than protection in the early stages, and the need for founders to have a clear and comprehensive founders agreement. They also explore the po
Building a Global Service Business
In this episode, Matt Watson and Ian Myers discuss the topic of hiring global talent. Ian shares his experience of starting a company in Sri Lanka and leveraging the highly skilled workforce there. They also discuss the challenges of scaling service-based businesses and the importance of upskilling and mentoring employees. Ian highlights the benefits of hiring talent from different countries and t
Construction Tech, Building Additional Products
Chris Callen, founder and CEO of Plot, discusses his journey in the construction technology industry and the challenges of coordinating job sites. He shares his experience with his first software startup and the lessons he learned from it. Callen explains how Plot's job site coordination software helps streamline the delivery and procurement processes in construction. He also discusses the role of
Startup Different
David Sinkinson, co-founder of AppArmor, shares his entrepreneurial journey and the lessons he learned along the way. He challenges startup myths and emphasizes the importance of finding the right co-founder. The conversation covers topics such as the need for funding, the psychology of being a founder, the evolution of AppArmor's product, the slow sales cycle in selling to colleges, and the impac
MidxMidwest and the State of Venture Capital in 2024
In this episode, Matt Watson interviews Dan Kerr from Flyover Capital, discussing the evolving landscape of venture capital in the Midwest, particularly in Kansas City. They explore the importance of networking for founders, the structure of the upcoming Mid-by-Midwest event, and the changing dynamics of funding, including the rise of debt and royalty financing. Dan shares insights on Flyover Cap
Founder Super Powers
In this episode, Matt Watson interviews Michelle Denogean, the Chief Marketing Officer of MindTrip and author of the book 'Grow Up.' They discuss the challenges that founders face when growing their companies and the importance of having a diverse team with different superpowers. Michelle introduces four superpowers: innovator, builder, connector, and persuader, and explains how each one contribut
Healthcare Tech Needs a Check Up
In this episode, Matt Watson interviews Markus Waite, the President of Empara and CIO of Goodroot, about healthcare technology. They discuss the challenges and complexities of the healthcare industry, the role of generative AI in simplifying healthcare processes, the high cost of healthcare in the United States, and the need for transparency and cost-saving solutions. Marcus also shares insights i
How to Access Non-Dilutive Funding
In this episode, Matt Watson interviews Keith Harrington, the founder and COO of Novel Capital, about non-dilutive capital and alternative funding options for startups. They discuss the different types of capital available, such as revenue-based financing and venture debt, and the importance of understanding when and how to raise money. Keith emphasizes the need for entrepreneurs to have access to
Technical Debt, Bridging Business & Tech
Christian Hammer, founder and CEO of Vala AI, joins Matt Watson on the Startup Hustle podcast to discuss AI for software development and the concept of technical debt. They explore the challenges of bridging the gap between business needs and technology, the different definitions of tech debt, and the importance of keeping up with the rate of change in the industry. Christian shares insights into
SaaS vs Professional Services, Business Growth
In this episode, Matt Watson and Ryan Dowdy discuss the difference between professional service companies and SaaS companies. They explore the challenges and opportunities of scaling a service-based business and the importance of sales and distribution in entrepreneurship. They also touch on the significance of personal branding for founders and the role it plays in building trust and thought lead
Product Adoption & Reducing Churn
In this episode, Matt Watson and Brett Sears discuss the importance of customer onboarding and training in software companies. They highlight the need for software companies to focus on getting customers to see value and have an 'aha' moment as quickly as possible. They also emphasize the significance of understanding the perspective of new users and providing a seamless onboarding experience. Th
Why the Inc 5000 is a Big Deal
In this episode, Matt Watson and Ryan Dowdy discuss the importance and benefits of being recognized on the Inc 5000 list. They explore the motivations behind winning awards and the impact it has on company culture, employee morale, and recruiting. They also highlight the value of third-party validation and how it builds credibility and trust with customers and investors. The conversation emphasize
Creating a Private Stock Market
Sim Desai, founder and CEO of Hive, discusses the creation of a secondary stock market for private companies. He explains the challenges of the current system, where selling private stock options is fragmented and opaque. Hive aims to centralize and automate the secondary market process, providing a platform for buyers and sellers to connect. The target market for Hive ranges from small companies
Transition from Founder to CEO, Resiliency, Avoiding Burnout
In this episode, Matt Watson interviews Vijay Rajendran, the coach and CEO of Startup System, about startup resilience and fundraising in the current economic climate. They discuss the challenges faced by startups, the importance of being cashflow positive, and the need to adapt and refine value propositions. They also explore the role of marketing, the significance of communication and delegation
Startup Positioning
In this episode, Matt Watson interviews Dale Walden, the founder of Njord & Co, a SaaS B2B marketing company. They discuss the importance of positioning in marketing and how it can help companies focus on their target audience. Dale shares his experiences in the B2C and B2B worlds and emphasizes the need for founders to niche down and focus on a specific customer profile. They also discuss the
The Remarkability Formula
In this episode of the Startup Hustle podcast, Matt Watson interviews Rich Brooks, the president of Flight New Media, about digital marketing and the Remarkability Formula. They discuss the impact of AI on marketing, the importance of finding your uniqueness, and the benefits of niching down. Rich explains the four lenses of remarkability: find, focus, frame, and forge. He also shares insights on
Scaling an Enterprise Data Startup
In this episode of the Startup Hustle podcast, Matt Watson interviews Ozan Unlu, the founder and CEO of Edge Delta, an observability company. They discuss the challenges of managing large amounts of data in complex production environments and the need for developers to have access to production data without compromising security. Ozan shares his journey from being a software developer at Microsof
Building Up Tech Talent
Neelima Paraskar, founder and CEO of Snap IT, discusses her journey in the tech industry and the challenges of hiring and retaining talent in the IT field. She shares how Snap IT started as a training company to address the lack of affordable and skilled engineers in Kansas City. Neelima also talks about the impact of AI on software development and the changing skills required in the industry. She
How to Make Opportunity Happen
Maria Flynn, founder and CEO of AmbioLogix, discusses her background in healthcare technology, entrepreneurship, and the digital health industry. She shares insights from her book 'Make Opportunity Happen' and provides valuable advice for entrepreneurs. The conversation covers topics such as urgency, finding opportunities, and practical advice for business success. Urgency is a critical factor in
The Complexities of SaaS Billing
Thinking of taking your software global but worried about navigating different markets and regulations? We've got you covered! Join Matt Watson as he explores the world of SaaS in Sweden with Nicholas Lilja, the founder and CEO of Younium, a billing and subscription management platform. In this episode, you'll discover: The unique challenges and opportunities of launching a SaaS company in Sweden
Asking for What You Want, Slack Early Days
Ever wonder why amazing entrepreneurs sometimes struggle to ask for what they want? This episode explores the surprising roadblocks that can hold even the most successful founders back. We'll be joined by Kenneth Berger, an executive coach who's seen it all—from Slack's explosive growth to the unique challenges faced by startup founders. Here's what you won't want to miss: Secrets from Slack's ea
From Pet Stores to SaaS & The Steps to Success
How does an experienced retail expert construct a cutting-edge financial platform? Prepare yourself because that's precisely the fascinating topic we're exploring in this episode!
Our guest today, Brad Parker, takes us on a wild ride through his 20-year retail experience, growing a business from a single location to a multi-million dollar empire. But Brad's story doesn't end there. He saw a gap in
Why Startups Get Stuck & The Pitfalls of Raising Money
Have you ever dreamt of launching a startup but worried about the dangers of scaling too quickly? Or maybe you're already running a business that feels stuck, unable to reach its full potential.
This is the podcast for you. Join host Matt Watson as he explores the fascinating world of entrepreneurship with Dave Hirsch, a seasoned investor and turnaround specialist. Together, they'll crack the code
Mastering Software Sales
Have you poured your heart and soul into building a game-changing SaaS product, only to find crickets chirping when it comes to sales? Fear not, fellow entrepreneur, because you're in the vast company of frustrated founders.
This episode of "Mastering Software Sales" dives deep into the trenches of selling software with industry expert Matt Wolach. Matt, a former technical founder who himself bat
How Honeycomb Created a New Product Category: Observability
Do you feel like you're flying blind when it comes to your software?
In today's episode, we dive deep into the world of observability - it's not just monitoring on steroids, and we'll explain why. Our guest, Charity Majors, co-founder and CTO of Honeycomb, will break down the concept and how it's changing the game for developers.
Get ready to hear about:
Observability 1.0 vs. 2.0: Is your toolkit
AI in Healthcare, First-Time CTO
Did you know traditional breast cancer screenings can miss early signs of the disease?
In this episode, we get an exclusive look into MedCognetics, a company using AI to revolutionize breast cancer detection. Matt Watson chats with guest Tim Cogan, MedCognetics co-founder & CTO, about how AI can:
Catch cancer earlier: Imagine AI spotting subtle abnormalities that might escape the human eye, l
Outbound Sales & Gamify Sales
Are you tired of the same old outbound sales tactics that just don't work?
In this episode, we'll be joined by entrepreneur Steve Claydon, founder of The Outbound Game, to chat about shaking things up with gamification and personalization.
Steve used to be stuck in the trenches of sales, and let's face it, it can be a grind. But he realized there had to be a better way to motivate salespeople and
Generative AI & Legal Tech
Are robots about to take over your lawyer's job?
Not quite, but Artificial Intelligence is poised to revolutionize the legal industry. In this episode, Matt Watson ventures into the world of immigration law with Josh Waddell, co-founder of VisaLaw.ai.
Josh isn't just another lawyer; he's a legal tech pioneer who saw the limitations of traditional practice and decided to disrupt it from within. We'
The 7 Types of a CTO
Ever heard the term "CTO" and wondered what it actually means? In the wild world of startups, the role can be a bit of a mystery.
In this episode, we're joined by Adelina Chalmers, also known as the "Geek Whisperer." Buckle up as we dissect the ever-evolving role of a startup CTO. We'll crack open the code on how CTOs can translate techie jargon into investor gold, and explore the crucial (but of
Pivoting & Bootstrapping to 1000 Customers
Ever gotten hit with a chargeback? You're not alone. In this episode, we dive into the world of e-commerce fraud with Qi Cao, the co-founder and CEO of Chargeblast, a company helping merchants fight back against unfair chargebacks.
Qi Cao went from scientist to entrepreneur after experiencing the pain of chargebacks firsthand. Now, he's helping businesses win back revenue and avoid costly disput
The Power of Knowledge & Bootstrapping for 20 years
Tired of your tedious onboarding routines for new hires and useless knowledge bases no one seems to use?
This episode of Startup Hustle is your guide to conquering knowledge transfer in the digital age. We chat with Greg DeVore, CEO of ScreenSteps, a software platform that's helping companies slash onboarding times and boost employee productivity.
In this episode, you'll learn:
How to ditch the c
The Evolving Role of the CTO
In this compelling episode, join Matt Watson as he sits down with Stefan Schmidt, a seasoned CTO coach and author of the acclaimed book "Amazing CTO." Together, they discuss the pivotal role of a Chief Technology Officer (CTO), exploring crucial insights on when to bring one on board and the critical errors to avoid in the selection process.
Stefan underscores the importance of idea validation bef
From Sales Guy to Tech Founder
In this episode of Startup Hustle, Matt Watson interviews Robby Yates, co-founder and Chief Everything Officer of FollowApp, a networking software company. They discuss Robbie's journey from being a salesperson to becoming an IT guy and starting his own company. They also talk about the importance of networking, the challenges of being a non-technical founder, and the benefits of white labeling. R
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