William Glass

The Will Glass Show

Business EN ↓ 128 episodes

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.

Author

William Glass

Category

Business

Podcast website

www.siliconalleypodcast.com

Latest episode

Mar 27, 2026

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Episodes

The Fire In Your Belly, Building a Liquor Brand, & Flipping Businesses | Chander Arora Founder & CEO of Red Eye Louie's 06.11.2020

52: In The Fire In Your Belly, host William Glass sits down with Chander Arora, the founder and CEO of Red Eye Louie's.  In today’s episode, we go deep into Chander’s entrepreneurial journey and how he went from driving a forklift in a textile factory to founding an international spirits brand. Chander is wide-open about both his successes and failures. There are some doozies from terrib...

A Tale of Two Valleys | Martin Babinec | Founder of TriNet (NYSE: TNET) & Author of More Good Jobs 30.10.2020

51: A Tale of Two Valleys, host William Glass sits down with Martin Babinec, an industry titan, entrepreneur, investor, philanthropist, and Author. Martin discusses his two contrasting valleys, Silicon Valley & the Mohawk Valley in upstate New York. You’ll hear the challenges that Martin overcame at the helm of TriNet leading through the boom and bust of the dot com bubble and how he overcame...

Producing Creativity and Representing Artists | Jimmy Carter, Founder of Legacy West Media 23.10.2020

50: In Producing Creativity, host William Glass sits down with Jim Carter, the founder of Legacy West Media . Jim discusses how repetitive physical injuries forced him to change his life’s path away from athletics and embrace his natural creativity. We discuss the power of travel and developing deep connections with a diverse set of people and how those connections not only bring Jim joy but also...

Empowering the Gift of Giving | Kelly Keurzoneff, Founder of Givelist 16.10.2020

49: In Empowering the Gift of Giving, host William Glass sits down with Kelly Keurzoneff, founder of Givelist . Kelly discusses the importance of social impact and how we can better support our fellow humans especially in times of need. She discusses the challenges of being a solo-founder (the loneliness) and how to continue to build your business without a co-founder. In addition, Kelly shar...

Competing When There's Nothing to Lose, How to Build an Antifragile Business | Tom Libelt, Founder of Smart Brand Marketing 09.10.2020

48: Competing When There's Nothing to Lose, host William Glass sits down with Tom Libelt, founder of Smart Brand Marketing . Tom dives into the concept of building an antifragile business that not only survives during uncertain times but thrives. He also gets into the benefits of being lazy and spending more time thinking versus spending all of your time hustling. One example of that approach...

Solving Financial Literacy | William Glass Guest Appearance on the Bacon Bits 'n' Bytes Podcast 02.10.2020

47: Solving Financial Literacy, host William Glass is interviewed on The Bacon Bits ’n’ Bytes Podcast by Karen Swyszcz. Together they discuss why financial well-being and financial literacy are so important as well as the vision for Ostrich.  On that note, Ostrich is approaching a public beta release and will of course give early access to Silicon Alley listeners who want to be the first to j...

The Art of Productive Screen Time | Laura Page-Hamelin & Graeme McKay, Co-Founders of Artebula 25.09.2020

46: The Art of Productive Screen Time, host William Glass sits down with Laura Page-Hamelin & Graeme McKay, co-founders of Artebula. Together they discuss the power of creativity and how promoting creative children lead to future innovators. From there we explore the challenges facing parents and children with the current content platforms and how Artebula is focused on promoting productive sc...

Developing the Perfect Product: How to Build a Minimum Viable Product (MVP) | Ned Lomigora, Founder of Cape Ann Tech 18.09.2020

45: Developing the Perfect Product: How to Build a Minimum Viable Product (MVP), host William Glass sits down with Ned Lomigora, Serial Tech Entrepreneur & Founder of Cape Ann Tech to discuss the illustrious MVP. In today’s episode, Ned walks us through how to develop a Minimum Viable Product (MVP), the common pitfalls, and why it is so crucial when developing a new product. We spend the last...

Exploring Your Inner Voice and Discovering Equanimity | Tej Singh, Host of The Growth Lab Podcast 11.09.2020

44: Exploring Your Inner Voice, host William Glass sits down with Tej Singh a Sr. Sales Executive and Podcaster to discuss how to find your purpose through what Tej refers to as equanimity and walking us through his process of self-discovery. You’ll learn how expectations can be our own worst enemy and how to deal with that feeling that you are not aligned with your purpose. Tej shares a number of...

Making Money a Family Topic | Mike Fraietta, Founder of KidFolio 04.09.2020

43: Mike Fraietta - Making Money a Family Topic, host William Glass sits down with the Founder & CEO of KidFolio. KidFolio is an app that helps friends and family send money to kids safely and easily all while creating meaningful ways to bond, learn & build for the future. The idea for KidFolio came out of Mike’s own experiences buying stocks for his niece over the years and then his...

Just Let Them Play, Coaching Elite Teams, and Defining Expectations | Jay Hammond 28.08.2020

42: Jay Hammond - Just Let Them Play, Coaching Elite Teams, and Defining Expectations, host William Glass sits down with Jay Hammond a championship-winning soccer coach. We zoom in to the similarities between sports and business. You’ll hear Jay discuss how he approaches building championship-winning teams from utilizing personal goal setting with his players to his approach to understanding...

The Mission Isn't Money, It's Impact | Deric Cahill, Co-Founder of WickedBold Chocolate 21.08.2020

41: Deric Cahill - The Mission Isn't Money, It's Impact and How to Build a Chocolate Empire, host William Glass sits down with serial entrepreneur, sales professional, and podcaster, Deric Cahill. Deric shares his experience building multiple different businesses from car detailing to handcrafted chocolate. You'll hear how Deric overcame a poverty-stricken childhood and parents with substance...

Brad Feld, Foundry Group & Techstars: Being a Human is Hard, Work-Life Balance Is Nonsensical, & Why Entrepreneurship Is Foundational to Society 14.08.2020

40. Brad Feld - Being a Human is Hard, Work-Life Balance Is Nonsensical, & Why Entrepreneurship Is Foundational to Society, host William Glass sits down with renowned Venture capitalist Brad Feld. Brad shares his insights across a number of areas including leadership during a pandemic, advocating for social justice, and accessing mental health care when you have limited resources. "Being a hum...

Why Is My Brain Thinking This Way | Randall Ledet Jr. 07.08.2020

39: Why Is My Brain Thinking This Way, host William Glass sits down with Randall Ledet Jr., a technology sales executive at Gartner. Following the death of George Floyd and truly seeing the reality of Black Americans in our society, host William Glass posted on Social Media that he would use this platform to be an advocate for People of Color. Randall and Will coordinated this episode to tell his...

Don't Just Focus on the Money | Karen Swyszcz, Founder of Kaibigan Connection 31.07.2020

38. Don't Just Focus on the Money, host William Glass sits down with Karen Swyszcz, a best selling author, entrepreneur, and teacher. Karen talks about how she didn't grow up with the entrepreneurial bug and her career has been more of a rock-climbing wall than a clear path.  Karen Swyszcz is the co-founder of  Kaibigan Connection  - an organization that is dedicated to connecting F...

Seven Lessons From The First Year In Business | William Glass, Co-Founder of Ostrich 24.07.2020

#37 In this episode, Seven Lessons From The First Year In Business, host William Glass shares 7 key lessons he's learned through the first year of building Ostrich . Glass provides concrete examples of what has worked well for him and what has not. You’ll hear from past guests that embody the lessons learned from Andrew Holliday and William Glass's first-year starting up Ostrich. The 7 lessons are...

How to Build a Brand on Social Media | Scott Aaron, Best Selling Author, Coach, & Speaker 17.07.2020

36: How to Build a Brand on Social Media, host William Glass sits down with Scott Aaron, a best selling author, business coach, and speaker. Together they discuss the keys to building a strong personal and business brand on LinkedIn through human-centric approaches. Scott opens up about his struggles building multiple 6 figure businesses and how he was thrust into entrepreneurship at the age...

Finding Your Purpose and Live an Authentic Life | Austin Walker, Founder of RAW Coaching 10.07.2020

35. Finding Your Purpose and Living an Authentic Life, host William Glass sits down with Austin Walker , co-host of Purpenthicity , a certified life coach, and technology sales executive. We dive not only into Austin’s backstory and where his focus on living a purpose-driven life comes from but discuss his experience as a Black man navigating corporate America and growing up in a predominately whi...

Over Quota Guest Appearance: How To Go From No Industry Experience To Sales Management In Under 2 Years 03.07.2020

34: Now on today’s episode, How to go from no industry experience to sales management in under 2 years, I sit down with Jay Webb on his podcast Over Quota. If you remember Jay was on episode #29 Flipping the Script: Sell Your Way Out of Anything. Jay probes deep into my backstory and we talk about all things sales. Jay Webb is the Founder of the j. David Group ,  which helps rapidly growing s...

Where People Fall Short and Building a Socially Focused Business | Ben Sampson Founder of WeHero 26.06.2020

33: Where People Fall Short, host William Glass sits down with Ben Sampson, Founder of WeHero . Ben shares 7 tips for finding product-market fit and how he’s applied them across his own businesses. In addition, we dive deep into Ben's current endeavor WeHero, the early mistakes - teaser it involves an illegal very addictive narcotic - and how the team overcame that pitfall as well as adapted their...

Beyond Profit: Ethics in Business | Sophia Sunwoo, Serial Entrepreneur 19.06.2020

32: Beyond Profit: Ethics in Business, host William Glass sits down with Sophia Sunwoo, Founder of Ascent Strategy to discuss the biggest pitfalls she sees entrepreneurs make and how to get out of the extreme bootstrap mindset. Sophia highlights some of the key differences between leading a for-profit and a non-profit business and how if you can raise money in the non-profit world you can sell jus...

The Side Of Startups We Don't Talk About | Jeff Wald Founder of WorkMarket, Author of The End of Jobs, & Angel Investor 12.06.2020

31: The Side of Startups We Don't Talk About, host William Glass sits down with Jeff Wald, Founder of WorkMarket to discuss the dark side of entrepreneurship, the future of work, and much more. This conversation is jam-packed with actionable advice and stories from Jeff's own experiences building multiple successful companies. Jeff's book, The End of Jobs is now available on Amazon.  Jef...

Driven To Succeed | Judah Longgrear, CEO & Co-Founder of Nickelytics 05.06.2020

30: Driven to Succeed William Glass sits down with Judah Longgrear, Co-Founder & CEO of Nickelytics who is an entrepreneur through and through. From buying a coffee shop for $5,000 at the age of 19 to starting Nickelytics which just finished the TechStars mobility program in Turin Italy. We go deep into building a tech company, raising money, pivoting, and having to deal with the backlash. Bef...

Flipping The Script: Sell Your Way Out Of Anything | Jay Webb, Founder of J. David Group & Host of The Over Quota Podcast 29.05.2020

29: Flipping The Script: Sell Your Way Out Of Anything, host William Glass sits down with Jay Webb, Founder of the j. David Group & Host of The Over Quota Podcast . An enthralling conversation we go deep into understanding what drives Jay, going all in, and Jay's LAID philosophy of taking action.  Jay Webb is the Founder of the j. David Group ,  which helps rapidly growing softw...

Difficult Conversations With Difficult People | Ralph Peterson, Management Development Coach, Entrepreneur, & Best Selling Author 22.05.2020

28: Difficult Conversations With Difficult People, host William Glass sits down with Ralph Peterson, management development coach, entrepreneur, and best selling author to discuss what makes a great manager. A dynamic conversation that breaks down the myths of management from micromanaging to picking your battles. Ralph Peterson is the owner and operator of a management development company that he...

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