The Will Glass Show

William Glass
  • 5.0 (24)
  • ENTREPRENEURSHIP
  • UPDATED WEEKLY

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.

  1. MAR 27

    Birmingham Real Estate: History, Neighborhoods & Why the Math Still Works in 2026

    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 that fueled steel furnaces still divides the city's most valuable neighborhoods from the rest. You'll get a clear breakdown of market cycles from the 1990s through today, neighborhood tiers from Mountain Brook to Norwood, and the rental math behind Birmingham's cash flow reputation. In this episode: Birmingham's industrial history and why it still matters for real estateUAB as an anchor employer and what that means for market stabilityMarket cycles: 1990s through March 2026Neighborhood tiers: Class A, B, C & D breakdownsCap rates, occupancy rates & what rental returns actually look likeDowntown revitalization and the 2026 bull case2026 forecast: modest appreciation, strong single-family rental demandIf you're evaluating Birmingham for your portfolio — or just trying to understand the city before making a move — this is your starting point.

    25 min

  2. 11/06/2022

    The Consequences of the Startup Life, Rejuvenating Your Body, Mind, + Soul | Jon Carder, 4X founder

    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. After discovering functional medicine, Jon was able to revitalize his health and wellbeing. Vessel Health was born to help bring functional medicine to the masses. Follow the Silicon Alley podcast wherever you get your podcasts. __ Visit SiliconAlleyPodcast.com to become a guest and sign-up for the newsletter. Follow on: - Instagram: http://bit.ly/SIliconAlleyIG - LinkedIn: http://bit.ly/SiliconAlleyLI - YouTube: http://bit.ly/SiliconAlleyYouTube Our Sponsors: Ostrich provides a financial habit-building app that helps you build a strong financial foundation. When you first join Ostrich you'll receive your Ostrich financial health score that shows where you are today and how you compare to your peers. Get your Ostrich financial health score for free at https://www.getostrich.com Wicked Bold Chocolate is a vegan chocolate brand using just 3 natural ingredients in its chocolate. Delicious, natural and get 15% off using the promo code: SiliconAlley go to https://www.WickedBold.com About Jon Carder: Jon Carder is a serial entrepreneur. He built four start-ups over the last 23 years, including successful 3 exits. Jon has raised ~$100M in venture capital and hired hundreds of employees. That entrepreneurial lifestyle eventually took its toll and he started having challenges with low energy, brain fog, and trouble sleeping. These problems prevented Jon from consistently showing up as his best self. After talking to friends, he realized that these issues were actually pretty common. Jon learned that through lab work he could identify the root cause of some of the problems and improve them, but that wasn’t going to happen with his conventional doctor. After a lot of searching he eventually found a functional medicine doctor, who was able to identify, through expensive blood work, that Jon had nutrient deficiencies and high toxin levels. So, Jon adjusted his supplements, nutrition and lifestyle accordingly. And, within a month, he was feeling the best he had felt in years. This inspired Jon to start Vessel and use new technology to empower people to track and improve their wellness from home. www.vesselhealth.com Silicon Alley is a Financial Glass Production

    44 min

  3. 10/30/2022

    A New Way for Content Creators to Engage with Fans | Derek Gorthy, Enshrine.io

    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.  Follow the Silicon Alley podcast wherever you get your podcasts. __ Visit SiliconAlleyPodcast.com to become a guest and sign-up for the newsletter. Follow on: - Instagram: http://bit.ly/SIliconAlleyIG - LinkedIn: http://bit.ly/SiliconAlleyLI - YouTube: http://bit.ly/SiliconAlleyYouTube Our Sponsors: Ostrich provides a financial habit-building app that helps you build a strong financial foundation. When you first join Ostrich you'll receive your Ostrich financial health score that shows where you are today and how you compare to your peers. Get your Ostrich financial health score for free at https://www.getostrich.com Wicked Bold Chocolate is a vegan chocolate brand using just 3 natural ingredients in its chocolate. Delicious, natural and get 15% off using the promo code: SiliconAlley go to https://www.WickedBold.com About Derek Gorthy: Derek started his first business at the age of 15 after teaching himself how to repair Xbox 360 consoles and smartphones. Since then, he has started multiple companies that range from affiliate marketing sites to algorithmic stock trading. After college, Derek started his career in consulting -- working in the tech, finance, energy, and health industries. He found his niche in understanding difficult concepts and complex systems, then distilling the value of those concepts and systems into a form that anyone could understand. Derek is currently working on his latest company, Enshrine. Enshrine is a Web3 community engagement platform focused on giving content creators the ability to build unique, cross-platform experiences for their fans. Derek is passionate about the company's mission because he believes content creators should own their financial relationships with their fans, not large tech platforms. https://www.linkedin.com/in/derekgorthy/  https://enshrine.io/ Silicon Alley is a Financial Glass Production

    42 min

  4. 10/23/2022

    Unlocking Profit for SaaS Marketplaces | Joe Keeley, founder of JustiFi

    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 found JustiFi which arbitrages payment processing options to ensure SaaS marketplaces can process transactions more efficiently.  Follow the Silicon Alley podcast wherever you get your podcasts. __ Visit SiliconAlleyPodcast.com to become a guest and sign-up for the newsletter. Follow on: - Instagram: http://bit.ly/SIliconAlleyIG - LinkedIn: http://bit.ly/SiliconAlleyLI - YouTube: http://bit.ly/SiliconAlleyYouTube Our Sponsors: Ostrich provides a financial habit-building app that helps you build a strong financial foundation. When you first join Ostrich you'll receive your Ostrich financial health score that shows where you are today and how you compare to your peers. Get your Ostrich financial health score for free at https://www.getostrich.com Wicked Bold Chocolate is a vegan chocolate brand using just 3 natural ingredients in its chocolate. Delicious, natural and get 15% off using the promo code: SiliconAlley go to https://www.WickedBold.com About Joe Keeley: Joe Keeley is a dynamic, yet thoughtful entrepreneur and conscious leader. As such, Keeley is the CEO and Co-founder of JustiFi Technologies, a venture-backed fintech business providing payments and fintech infrastructure and strategy for vertical SaaS platforms. JustiFi exists to accelerate the potential of vertical SaaS platforms by bringing optimized embedded payments and beyond payments fintech solutions to bear resulting in increased value for the platform of 3-5X with a remarkably lower cost of ownership. https://www.linkedin.com/in/joekeeley https://www.justifi.ai/ Silicon Alley is a Financial Glass Production

    42 min

  5. 10/16/2022

    How to Run the Perfect Venture Capital Fundraise | Nathan Beckord, Foundersuite

    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 journey and how he came to start Foundersuite. Follow the Silicon Alley podcast wherever you get your podcasts. __ Visit SiliconAlleyPodcast.com to become a guest and sign-up for the newsletter. Follow on: - Instagram: http://bit.ly/SIliconAlleyIG - LinkedIn: http://bit.ly/SiliconAlleyLI - YouTube: http://bit.ly/SiliconAlleyYouTube Our Sponsors: Ostrich provides a financial habit-building app that helps you build a strong financial foundation. When you first join Ostrich you'll receive your Ostrich financial health score that shows where you are today and how you compare to your peers. Get your Ostrich financial health score for free at https://www.getostrich.com Wicked Bold Chocolate is a vegan chocolate brand using just 3 natural ingredients in its chocolate. Delicious, natural and get 15% off using the promo code: SiliconAlley go to https://www.WickedBold.com About Nathan Beckord: Nathan Beckord is the CEO of Foundersuite.com a venture-backed company that makes the leading “funding stack” (Investor Database, CRM, Pitch Deck Hosting, Bulk Email, Virtual Data Room and Investor Update tools) for startups raising capital. Since launching in 2016, users have raised over $3 Bln in seed and venture capital. Prior to starting Foundersuite, Nathan spent ten years working with over 150 startups as interim CFO, Business Developer, and Advisor. Nathan has an MBA in Entrepreneurship, a BSC in Finance, and is a Chartered Financial Analyst (CFA). In his free time, he enjoys sailing, traveling, and riding motorcycles. Silicon Alley is a Financial Glass Production

    48 min

  6. 10/09/2022

    Hacking the Student Loan Repayment System | Bobby Matson, Payitoff

    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 supports fintech companies and banks repayment solutions. Follow the Silicon Alley podcast wherever you get your podcasts. __ Visit SiliconAlleyPodcast.com to become a guest and sign-up for the newsletter. Follow on: - Instagram: http://bit.ly/SIliconAlleyIG - LinkedIn: http://bit.ly/SiliconAlleyLI - YouTube: http://bit.ly/SiliconAlleyYouTube Our Sponsors: Ostrich provides a financial habit-building app that helps you build a strong financial foundation. When you first join Ostrich you'll receive your Ostrich financial health score that shows where you are today and how you compare to your peers. Get your Ostrich financial health score for free at https://www.getostrich.com Wicked Bold Chocolate is a vegan chocolate brand using just 3 natural ingredients in its chocolate. Delicious, natural and get 15% off using the promo code: SiliconAlley go to https://www.WickedBold.com About Bobby Matson: Bobby Matson is the CEO and founder of Payitoff, a venture-backed team automating every aspect of student loan repayment for fintechs and workplace providers. A few years ago, Payitoff's founder, Bobby, and his wife were weighed down by crushing six-figure student debt, unsure if they’d ever be able to start a family or own a home. Bobby spent nights and weekends codifying student loan regulations and building an algorithm to help his family navigate their personal student debt crisis. This technology, which in time became the core to Payitoff’s algorithm, helped him gain what every borrower seeks: a course of action for his student loan management that without a doubt would get the the best possible financial outcome for his family. Amidst the confusion and complexity of the student loan system, Bobby was able to turn chaos into certainty thanks to this algorithm. With that freedom, Bobby and his wife were empowered to start a family and move forward with their lives. (They currently have an adorable 3-year-old daughter!) Of course, Bobby quickly realized his struggle wasn’t unique. 43 million other borrowers could benefit from the technology he developed in order to overcome the overwhelming complexity of student loan debt. He founded Payitoff in 2018, and we’ve since built a suite of innovative tools to revolutionize student loan management, from the unique perspective of having experienced the struggle firsthand. https://www.linkedin.com/in/bobbymatson/ Silicon Alley is a Financial Glass Production

    38 min

  7. 10/02/2022

    A Contrarian View of Technological Innovation | Somi Arian, InPeak

    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 on society. This episode is deep and a bit contrarian, enjoy! Follow the Silicon Alley podcast wherever you get your podcasts. __ Visit SiliconAlleyPodcast.com to become a guest and sign-up for the newsletter. Follow on: - Instagram: http://bit.ly/SIliconAlleyIG - LinkedIn: http://bit.ly/SiliconAlleyLI - YouTube: http://bit.ly/SiliconAlleyYouTube Our Sponsors: Ostrich provides a financial habit-building app that helps you build a strong financial foundation. When you first join Ostrich you'll receive your Ostrich financial health score that shows where you are today and how you compare to your peers. Get your Ostrich financial health score for free at https://www.getostrich.com Wicked Bold Chocolate is a vegan chocolate brand using just 3 natural ingredients in its chocolate. Delicious, natural and get 15% off using the promo code: SiliconAlley go to https://www.WickedBold.com About Somi Arian: Somi Arian began her journey with a passion for making science and technology more inclusive. In 2018 Somi released her multi-award-winning documentary, "The Millennial Disruption", featuring industry leaders from The Economist, Marie Claire, Bentley, JLR, and Gary Vaynerchuk, to name a few. The documentary was followed by Somi's book on the future of work, “Career Fear (and how to beat it), where she observed the severe lack of women in leadership in Business and Technology. So, she set out to do something about this. Somi launched FemPeak as a Think Tank for Women in Business and Technology in August 2020. With her "I have a Dream" video on LinkedIn. The Think Tank consisted of four big virtual conferences with thousands of attendees and close to a hundred panellists including the Managing Director of Marie Claire, CEO of Bentley Motors, and thought leaders from Google, Microsoft and Morgan Stanley. We wanted to know why women were absent in the top tier of business and Technology. https://www.somiarian.com/ https://inpeak.xyz/ Silicon Alley is a Financial Glass Production

    43 min
  8. Venturing into Venture Capital | Ketul Patel, Investor

    09/26/2022

    Venturing into Venture Capital | Ketul Patel, Investor

    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 large global venture capital firm. Follow the Silicon Alley podcast wherever you get your podcasts. __ Visit SiliconAlleyPodcast.com to become a guest and sign-up for the newsletter. Follow on: - Instagram: http://bit.ly/SIliconAlleyIG - LinkedIn: http://bit.ly/SiliconAlleyLI - YouTube: http://bit.ly/SiliconAlleyYouTube Our Sponsors: Ostrich provides a financial habit-building app that helps you build a strong financial foundation. When you first join Ostrich you'll receive your Ostrich financial health score that shows where you are today and how you compare to your peers. Get your Ostrich financial health score for free at https://www.getostrich.com Wicked Bold Chocolate is a vegan chocolate brand using just 3 natural ingredients in its chocolate. Delicious, natural and get 15% off using the promo code: SiliconAlley go to https://www.WickedBold.com About Ketul Patel: Ketul started his career working in startups. He joined Jet.com after it was acquired by Walmart, and he joined Paxos before it became a unicorn. In 2019, he launched a tech services investment firm called Eximer Capital. Today, he's an early stage investor at a global venture capital firm, Headline. https://www.linkedin.com/in/ketulpatel1 Silicon Alley is a Financial Glass Production

    46 min
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About

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.

Information

  • Creator
    William Glass
  • Years Active
    2019 - 2026
  • Episodes
    128
  • Rating
    Clean
  • Copyright
    © William Glass
  • Show Website
    The Will Glass Show