After 30 years of building startups, teams, and products, entrepreneur and media exec Jeremy Toeman is taking time to reflect — and to ask the questions that don’t get answered in pitch decks or exit press releases.
Founder@50 is a podcast for anyone rethinking life, work, or identity. Guests include 20-somethings just starting out to 50-somethings starting over or reflecting back.
Through candid conversations with founders, creators, and builders from all walks of life, Jeremy draws on decades of experience. His career spans places like WarnerMedia, Etsy, and CBS, and this podcast is here to uncover the lessons, mistakes, and moments of reinvention that shape how we build meaningful lives.
Because after years in the game, what really matters is clarity, growth, and doing work that actually lasts.
Still building. Still questioning. Always learning.
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In this episode of Founder@50, Jeremy sits down with colleague and good friend Ben Walter, a dynamic leader with an amazing career journey. From his early days at Continental Airlines to his current role as CEO of Chase for Business at JP Morgan Chase, Ben’s career is a testament to the power of cold emails and warm connections. With a background that spans multiple industries, including consulting, retail, and asset management, Ben’s journey is as diverse as it is inspiring, showcasing his ability to pivot and thrive in various roles.Ben and I explore how his initial role at Continental Airlines set the stage for his future successes, and how his strategic mindset was honed through his experiences at BCG and Gap Inc. We delve into pivotal moments that shaped his career, including his transition to Hiscox and his current leadership at JP Morgan Chase.
Key Takeaways:
* How a cold email to an airline executive launched Ben’s career in aviation (not to mention him learning how to fly).
* Insights on managing imposter syndrome and the importance of authenticity in leadership.
* The impact of in-person mentorship versus remote work on professional development.
* His “three to five” goal template to help guide major career decisions.
In our chat, Ben also shares his vision for the future of leadership in the age of digital transformation, offering valuable insights for entrepreneurs and leaders alike. Whether you’re a seasoned professional or just starting out, Ben’s journey from cold emails to warm connections offers a wealth of knowledge and inspiration.
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8 Jan 2026
Debra Aho Williamson: A Marketing Virtuoso
In this episode of Founder@50, Jeremy sits down with the remarkable Debra Williamson, a trailblazer in the world of digital marketing and media. From her early days as a copy editor at Advertising Age to leading the social media practice at eMarketer, Debra’s career is a testament to the power of seizing opportunities and adapting to the ever-evolving landscape of technology and media. With a background in music and English literature from Northwestern University, Debra’s journey is as diverse as it is inspiring, showcasing her ability to pivot and thrive in various roles, including her current venture, Sonata Insights.
Debra and I dive into how her role at Advertising Age set the stage for her future successes, and how her work at eMarketer (love the little red graphs!) positioned her as a thought leader in social media marketing. We talk through pivotal moments that shaped her career, including her collaboration with industry giants like John Battelle and her contributions to the groundbreaking publication, the Industry Standard. Other highlights include:
* How Debra’s first job at Advertising Age magazine laid the foundation for her illustrious career in digital marketing.
* Her role as a demographics analyst at eMarketer allowed her to pioneer social media research, leading to a 17-year tenure in the field.
* Shared insights on the challenges and opportunities presented by AI in marketing, drawing from her extensive experience in the industry.
* Hear the story behind Debra’s decision to launch Sonata Insights, a venture that combines her passion for music and marketing.
In our chat we Debra also shares her vision for the future of marketing in the age of AI, offering valuable insights for entrepreneurs and marketers alike. Whether you’re a seasoned professional or just starting out, Debra’s journey from the oboe to Sonata offers a wealth of knowledge and inspiration.
Get full access to Founder@50 at founderat50.substack.com/subscribe (https://founderat50.substack.com/subscribe?utm_medium=podcast&utm_campaign=CTA_4)
8 Dec 2025
Tom Matta: from Pittsburgh to Paradise
In this episode of Founder@50, Jeremy sits down with Tom Matta, a dynamic entrepreneur whose journey from the steel mills of Pittsburgh to the sunny shores of Hawaii is nothing short of inspiring. With a background in material science and engineering from Carnegie Mellon, Tom’s career took a fascinating turn as he pivoted from metallurgy to the world of startups. From his early days at Capital Technologies to his pivotal role in the early days at Carta, Tom’s story is a testament to the power of adaptability and vision.
Tom’s career is a tapestry of diverse experiences, from his internship at a US Steel melt shop to co-founding StatEasy, a media platform for high school sports. His journey through the tech landscape includes stints at Booz Allen Hamilton and his current role at Forecastr, where he continues to innovate in the financial planning space. Along the way, Tom has crossed paths with industry icons like Henry Ward and Manu Kumar, learning invaluable lessons that have shaped his entrepreneurial spirit.
* Discover how Tom’s internship at US Steel led him to pursue an MBA and ultimately shift his focus to tech and entrepreneurship.
* Learn about Tom’s experience at Capital Technologies, where he worked on groundbreaking microwave-assisted hydro processing technology.
* Hear how Tom’s role at eShares (Carta) saw him grow from the 12th employee to a key player in a company with over 2,000 employees.
* Explore Tom’s insights on the importance of finding product-market fit, as learned from his startup StatEasy.
* Understand the impact of mentorship from industry leaders like Manu Kumar and how it influenced Tom’s career trajectory.
As Tom shares his journey, listeners will find a wealth of insights into the world of startups, tech innovation, and the art of pivoting in one’s career. Whether you’re an aspiring entrepreneur or a seasoned professional, Tom’s story offers a fresh perspective on navigating the ever-evolving landscape of business and technology. Tune in to hear how Tom’s experiences and connections have shaped his path, and perhaps find inspiration for your own journey.
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