Episodes

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 battled fierce competition in the early days, pulls back the curtain on the biggest challenges SaaS fou...

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 stuck in the past? We'll explore the evolution of this critical practice. AI in Debugging: Frien...

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, leading to earlier intervention and potentially better outcomes. Free up doctors' time: AI could become...

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 drive results. That's where gamification came in. We'll hear how Steve used fun and competition to...

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'll hear how his law firm embraced AI to automate tedious tasks, leaving lawyers free to focus on c...

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 often overlooked) skill of self-awareness for these tech titans. This episode is packed with insights...

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 disputes. But Chargeblast's journey wasn't always smooth sailing. We'll hear how Qi Cao pivoted from B2C to...

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 clunky manuals and build a system for capturing and organizing knowledge fast. A sneaky trick to s...

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 before engaging a CTO or developer and suggests starting with a PowerPoint slide deck to gather feedba...

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. Robby shares tips for effective networking and emphasizes building a strong team and listening to oth...

Join us as Chase Harmer, a seasoned entrepreneur with over 20 years in the fintech industry, dives deep into the challenges and innovations of building a fintech company with heart. In this episode, we explore the intersection of financial technology and charitable giving through Chase's latest venture, Wishes—a platform designed to transform how we support causes we care about. Episode Highlights: The Genesis of Wishes: From overcoming compliance hurdles to raising $30 million, Chase shares t...

Steve Wolfe, managing partner and co-founder of Growth Street Partners, joins Matt Watson on the Startup Hustle podcast to discuss practical fundraising for founders. They explore the challenges faced by practical founders in raising money and the drawbacks of traditional venture capital funding. They emphasize the importance of founder market fit and the advantages it brings. They also discuss the benefits of having a growth equity firm like Growth Street Partners as an investor, including the ...

In this episode, Matt Watson interviews Rob Snyder, the founder and CEO of Reframe, about product market fit and the challenges of being an entrepreneur. They discuss the definition of product market fit, the importance of customer case studies, and the need to focus on solving specific problems for a target audience. Rob shares insights from his program for founders and emphasizes the value of talking to customers and iterating on the sales pitch. They also touch on the difficulty of scaling a...

Feeling trapped on a workaholic hamster wheel? This episode of Startup Hustle dives deep into the entrepreneur's struggle for work-life balance and that elusive thing called happiness. Join serial entrepreneur and travel addict Michael Motamedi as he discusses aligning your company goals with your desire to, you know, not die alone. We'll crack the code on the "happiness threshold" (it's not about that third yacht) and explore why fixing your water heater might be more fulfilling than you thin...

This episode of Startup Hustle is a goldmine for aspiring entrepreneurs! Yaniv Bernstein, host of the StartUp podcast and founder of Funding Fit, joins the show to dish on the exciting and often messy world of startups. Ever heard of "entrepreneurial ADHD"? Yaniv, a former Google employee who freely admits to this condition, dives into the challenges founders face, including the pitfalls to avoid. Learn from his experience to dodge common mistakes and build a venture that thrives, not dives. I...

Join us as Matt Watson chats with Greg Head about the power of in-person events like the SaaS Open. We're talking about ditching the Zoom fatigue and forging real connections with founders who GET IT. They discuss the value of talking to other entrepreneurs and attending events. They highlight the power of community and the benefits of connecting with like-minded individuals. They also touch on the importance of in-person events and their impact on building relationships. The conversation empha...

Do you ever feel like you're the only one getting things done at your startup? This episode is for you! Matt Watson chats with Greg Schmedding, a problem-solver with a proven track record in the staffing industry, about the critical hires every startup needs to flourish. In this episode, you'll learn: Why delegating and letting go are essential for startup growth (and how to do it without losing control) The biggest hiring mistakes founders make (think: promoting that talented developer to CT...

In this episode of Startup Hustle, Matt Watson chats with Rex Kurzius, founder and CEO of Asset Panda, about the exciting (and sometimes messy!) world of building a global SaaS company. Get ready to hear about: The entrepreneurial itch: Rex, a serial entrepreneur, shares his insights on what drives him to build new businesses constantly. From home inventory to global asset tracking: Discover how Asset Panda pivoted from a consumer product to a successful B2B solution for tracking assets world...

Ever wonder what happens when you buy out your business partner? Join Jeff Munn and Matt Watson, the new CEO of Full Scale, as they go through Matt’s entrepreneurial rollercoaster in the first 90 days! In this episode, you'll hear: Matt's origin story: From problem solver to accidental business owner, Matt shares his hilarious and relatable journey. Leadership lessons learned (the hard way): Matt dives into the challenges and triumphs of taking over a company he once co-ran. Going global (a...

Have you ever wondered how entrepreneurship can change communities? This episode dives deep into business ownership with Dr. DeAngela Burns-Wallace, a leader with an impressive track record in government, education, and philanthropy. Now, she's at the helm of the Ewing Marion Kauffman Foundation, a powerhouse dedicated to empowering entrepreneurs, especially women and people of color. Here's what you won't want to miss: Inspiring stories: Dr. Wallace shares her incredible career journey, from...

Ever felt like your website is about to crash from a sudden surge in traffic? Our guest founder knows that feeling all too well. In this episode, we chat with the Chief Innovation Officer of WP Engine, Jason Cohen, about the company's incredible journey and his own path from burnt-out developer to successful entrepreneur. You'll learn: How Jason's early struggles with WordPress led to the creation of a billion-dollar business. The surprising secret weapon that helped WP Engine stand out from ...

Join Matt Watson for a blast-from-the-past reunion with his long-time friend, Danny Zaslavsky! This episode dives deep into Danny's fascinating journey, from growing up in a car dealership to becoming the founder of a tech startup, DealerCue. Matt and Danny reminisce about their early days working together, the challenges they faced in the car business, and the power of technology to revolutionize the industry. They'll discuss: The Birth of DealerCue: How Danny's experience managing a car...

Have you ever struggled to find reliable contractors for your home repairs? You're not alone! In this episode, we'll hear from Bo Lais, the CEO and founder of Lula. He started out helping homeowners but discovered a hidden goldmine in the property management industry. Bo and his wife faced the same challenge as many homeowners: finding qualified contractors. This led them to create a platform to connect homeowners with reliable professionals. But what they learned along the way was even more va...

Tired of dead-end jobs and feeling stuck in your career? Hope is on the horizon. In this episode, Matt Watson chats with Kadima Careers's Founder, CEO & Chief Accelerator, Alan Stein. Alan, a seasoned professional with a unique career path, shares his insights on: Fast-tracking your career and exploring side hustles: Learn how Alan went from being "tired of getting fired" to helping others land their dream jobs, and explore his experiences on both sides of the interview table. Crafting a winn...