The Will Glass Show
The Will Glass Show is where curiosity meets real talk on entrepreneurship, technology, real estate, and building a life on your own terms. Each week Will Glass — entrepreneur, investor, and builder based in Birmingham, Alabama — sits down with founders, investors, and innovators, or breaks down the ideas and trends shaping business and culture right now. From AI and crypto to Birmingham real estate and startup fundamentals, no topic is off limits. New episodes every Friday.
Episodes
Birmingham, Alabama isn't the next Nashville — and that's exactly what makes it interesting. In this episode, Will Glass breaks down the full picture of the Birmingham real estate market: where it came from, where it stands in March 2026, and how to think about it as an investor or homebuyer.
Will covers the city's origin as a geological accident, how UAB became Birmingham's economic backbone, and why the same ridge ...
122: In the Consequences of the Startup Life, Jon Carder, founder of Vessel Health, joins host William Glass to discuss his 23+ year entrepreneurial journey. From bootstrapping early in his career to raising venture capital, Jon experienced all of the classic trials and tribulations of being a startup founder. Living on Ramen early in his career helped him through the bootstrapping phase, but ultimately took a toll on his health. ...
121: In A New Way for Content Creators to Engage with Fans, Derek Gorthy, founder at Enshrine, joins host William Glass to discuss how web 3 can bring content creators closer to their fans. Derek shares his journey of founding Enshrine and how NFTs can be used to power a community. Enshrine was founded with creators in mind making it extremely simple to utilize NFTs without having to learn how to code or becoming an expert in web 3...
120: In Unlocking Profit for SaaS Marketplaces, Joe Keeley, founder of JustiFi, joins host William Glass to discuss how processing payments can drive revenue. Previously, Joe built a successful business connecting college athletes and students to families seeking highly skilled nannies and tutors. As the business shifted to a SaaS model, Joe was frustrated with how much he was paying in payment processing fees. Which led Joe to fou...
119: In How to Run the Perfect Venture Capital Fundraise, Nathan Beckord, founder of Foundersuite, joins host William Glass to discuss the secret to raising capital for your startup. Nathan walks through step-by-step the perfect startup fundraise and where many founders go wrong. You'll learn how to set yourself up for funding success and increase your likelihood of raising venture capital. Nathan also shares his entrepreneurial jo...
118: In Hacking the Student Loan Repayment System, Bobby Matson, founder of Payitoff, joins host William Glass to discuss his journey of becoming a founder. Bobby shares how his family's struggle to pay down student loans prevented him and his wife from starting a family. After hacking their way out of student loan debt, Bobby decided to commercialize his knowledge through Payitoff. Payitoff provides debt paydown software that supp...
117: In A Contrarian View of Technological Innovation, Somi Arian, founder of InPeak, joins host William Glass to discuss the future of human society. Somi describes herself as a tech philosopher and is passionate about the implications that technological innovation has on our society. Somi shares her views on the difficulties that technology will have on human society and how to rectify the challenges that technology will present ...
116: In Venturing into Venture Capital, Ketul Patel, investor at Headline, joins host William Glass to discuss his journey into the venture capital world. Ketul shares how he was drawn to technology and innovation at an early age. His curiosity led him deeper into the startup world where he joined a family member on the investing side. After finding some initial success, Ketul had to pivot his investment philosophy and joined a lar...
115: In Marketing in the Metaverse, Andre Kay, founder of Metaiblock + Sociallybuzz, joins host William Glass to discuss the future of marketing. As a social media marketing veteran, Andre Kay has been at the forefront of new marketing channels for multiple decades. Andre shares how he typically works with franchise clients and how business owners should be approaching marketing in web 3.
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114: In Busting Outsourcing Myths, Daniel Ramsey, founder of MyOutDesk, joins host William Glass to discuss how to find more time in your business through virtual assistants. Daniel shares the biggest mistakes entrepreneurs make when hiring a virtual assistant and helps clarify what tasks and job roles best suit a virtual assistant. In addition, we discuss the key concerns around quality, security, and communication that many entre...
113: In the Psychology of Money, Melissa Pancoast, founder of the Beans, joins host William Glass to discuss why our current approach to finances leaves millions of people behind. Melissa has spent years studying behavioral tech that can reduce financial stress and shares her learnings that she's applying at the Beans. We discuss how our current approaches to financial improvement are not aligned with our psychology which directly ...
112: In Build a PR Machine for Your Startup, Donna Loughlin, founder of LMGPR, joins host William Glass to discuss how to make a big splash with your company and keep the media coverage coming. Donna shares her own journey and examples of how startups can generate big buzz and sustain it long-term through strong storytelling. Towards the end Donna does a little workshopping to show you how to get started with your own company.
Follo...
111: In Debunking the MVP & Thriving in a Downturn, Bo Davis, founder of MarginEdge, joins host William Glass to discuss how he approached building MarginEdge counter to the traditional MVP model. Bo shares how his experience as a restauranteur gave him a competitive edge that allowed him to skip the traditional minimum viable product step. You'll also hear how Bo focused on putting customers at the forefront in 2020 when essen...
110: In Start with the Exit, Mart Achler & Mert Iseri, partners at MATH Ventures, joins host William Glass to discuss how to sell your startup for a lot of money. Through Mert's recent exit of his startup he learned that by focusing on how you will exit the business from the start you can build relationships that will ultimately lead to a better exit. Mark & Mert dive into the FAIR Framework and other tools that founders ca...
109: In a Consumer First Approach to Debt, Sean Hundtofte, founder of Solve Finance, joins host William Glass to discuss how our current lending practices fail borrowers. Sean spent years in consumer finance at the NY Fed and Better Mortgage and became frustrated with how our current lending practices fail consumers. We discuss his experience in the industry and how Solve Finance is taking a consumer-centric approach and the keys t...
108: In WTF is Financial Independence Anyway, Matt Ruttenberg, founder of SureLI Insurance, joins host William Glass to discuss financial independence and how to achieve this mythic state as an entrepreneur. Matt became frustrated after only spending 7-hours with his kid and realizing that his work was impeding his ability to be happy. Matt shares how he mapped out financial independence and a way for him to take his knowledge in t...
107: In Angel Investing in Startups for Dummies, Hall Martin, founder of TEN Capital Network, joins host William Glass to discuss how to get started investing in startups. Hall covers a wide range of basics from what size checks to write, what types of companies to focus on, and how to do proper due diligence. You'll come away with a solid foundation to start your angel investing journey and source potential investments.
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106: In M&A Uncovered, Kison Patel, founder of DealRoom & M&A Science, joins host William Glass to discuss how exactly mergers and acquisitions work. Kison shares what you need to know about M&A as a business owner, employee, and investor. Kison also goes into how he stumbled into an organic content strategy that has enabled DealRoom to grow without having to raise massive amounts of investor capital.
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105: In Creating Ads that Convert, Ben Marcoux, founder of Bottomless Branding, joins host William Glass to discuss the importance of creating ad copy that actually converts. Ben shares the steps to create really compelling ad copy that will increase your conversion rates. Additionally, Ben shares what led him to start his own agency and what it's like to be a solopreneur.
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104: In for the love of sport, David Arnett (@ChuckSportsApp), founder of Chuck, joins host William Glass to discuss how his passion for sports led him to build a better way to engage as a fan. David an avid sports fan felt there was something missing. He struggled to track all of his favorite teams, keep up with his fellow sports buddies, and began to dream of a better fan experience. That led him to build Chuck the social network...
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