Founder@50

In this episode, Jeremy Toeman engages in a lively conversation with Robert Plank, a tech enthusiast who transitioned from a computer science graduate to a successful entrepreneur. Robert shares his journey from his early days as a tinkerer to founding DFY Podcast, a company that helps creators manage their podcast content. He reflects on his experiences working at CSU Stanislaus and the pivotal decision to pursue entrepreneurship full-time.

In our episode we have a fun conversation about…

* The thrill of creating innovative software solutions and the journey from coding to entrepreneurship.

* Robert’s bold leap from academia to the startup world, and how he built a successful podcast agency.

* The secrets behind building a team and leveraging AI tools to enhance productivity and creativity.

* Jeremy and Robert waxing nostalgic about shareware and other 90’s era tech

As the conversation unfolds, Robert and Jeremy reflect on the importance of balancing technical skills with social skills, and the role of AI in modern content creation. Robert shares his philosophy on success, emphasizing the value of schedule freedom and the ability to pursue one's passions.

Tune in to hear some great stories from an inspiring tech entrepreneur.

In this episode, Jeremy chats with Ben Elowitz, who transitioned from early coding days at Microsoft to leading successful ventures such as Blue Nile and Fatbrain.com. Ben shares insights from their time at Bain & Company, where he learned to navigate the complexities of tech and telecom industries, including work with giants like Kaiser Permanente. We discuss pivotal moments, such as joining a startup at the dawn of the e-commerce wave, which later led to acquisitions by companies like Barnes & Noble.

Listeners will gain valuable lessons on:

* Discover the thrill of launching Blue Nile, the first online jeweler, and its journey to redefine e-commerce amidst giants like Amazon.

* Hear about Ben’s bold leap from Microsoft to the startup world

* Uncover some of the secrets behind Fatbrain.com's rapid rise and its acquisition by Barnes & Noble, marking a pivotal moment in e-commerce history.

* Experience the highs and lows of navigating capital markets during the dot-com boom and bust, and the lessons learned along the way.

* How we met via both selling startups (Dijit and Wetpaint) to Viggle, and our shared love for Nudgemail

* Find inspiration in the power of mentorship and the ripple effect of leadership, fostering a new generation of compassionate and skillful entrepreneurs.

As the conversation unfolds, Ben and I reflect on the ripple effect of leadership and the importance of fostering a compassionate and skillful generation of entrepreneurs. I call Ben the “VC Whisperer”, as he is an absolute master of helping founders make their visions not only business-ready, but investable-ready. Tune in to hear some great stories from an absolute mensch.

In this episode, we sit down with Robin Raskin, a trailblazer in the tech industry whose career spans from the early days of PC Magazine to shaping the future of CES. Robin shares her journey from an accidental entrepreneur to receiving a call from Bill Gates, offering a unique perspective on the evolution of technology and media. Her insights into the digital revolution and the future of AI are not to be missed.

Key Highlights:

* Robin's unexpected entry into the tech world and her first story for InfoWorld.

* The pivotal moment when Bill Gates called to discuss the future of personal computing.

* How Robin transformed CES events with innovative concepts like "Last Gadget Standing."

* The founding of the Virtual Events Group and its impact on the event industry.

* Robin's role as a connector in the tech world, bridging gaps between innovation and practical application.

* Her optimistic view on AI and its ethical implications for the future.

Tune in to discover how Robin's experiences and insights can inspire and inform your understanding of the tech landscape. Whether you're a tech enthusiast or a professional in the industry, this episode offers valuable lessons from a true industry leader.

In this episode of Founder at 50, Jeremy Toeman dives into the remarkable career of Sarah Rose, a visionary product leader who has navigated the ever-evolving landscape of technology and innovation. From her early days at Anderson Consulting to her pivotal role in the dot-com era with Mob Shop, Sarah's journey is a testament to the power of adaptability and foresight in product management.

Join us as Sarah shares her experiences in transforming ideas into impactful products, including her groundbreaking work at ModCloth, where she pioneered social commerce by integrating user-generated content into the shopping experience. Her story is one of serendipity, innovation, and leadership in the tech industry.

Topics Covered:

* The serendipitous start at Anderson Consulting

* Building Mob Shop (f/k/a Accompany), where they invented group e-commerce

* Pioneering social commerce at ModCloth

* Navigating product management without a playbook

* Insights on leadership and mentorship in tech

Discover how Sarah Rose has shaped the world of product management and continues to inspire the next generation of tech leaders. Tune in for an episode filled with insights, innovation, and inspiration.

In this episode of Founder at 50, Jeremy talks with Bob Gillbreath about his path from economics major to banker, marketer, founder, and now reflective entrepreneur. Bob shares candid stories of building companies, learning from failures, and finding purpose beyond profit.

Key themes from the conversation:

Early career lessons in banking and the moment he realized he needed work with real differentiation

Discovering digital marketing in its infancy and pioneering early campaigns at Procter and Gamble

Launching an agency, scaling it to hundreds of people, and selling to WPP during the dot com boomBuilding Ahalogy, a Pinterest marketing startup, surviving near collapse, and pivoting into influencer marketing before it went mainstreamRedefining success after exits by creating a holding company for service businesses and focusing on personal growth, mindfulness, and ego development

Bob also shares how he now uses AI as a thought partner in journaling and self-reflection, and why he believes his most important job today is learning to be a better human being.

Jeremy Toeman sits down with Dave Feldman to trace a career that spans the dawn of the commercial internet to today’s AI-fueled creative experiments. From pioneering exploring the Web using Mosaic to leading UX design projects at Yahoo/AOL, Google, and others, Dave shares insights on the evolution of product design, the challenges of founding startups, and the importance of team dynamics. Along the way, they dig into:

* Lessons from building in Web 1.0 and Web 2.0 eras

* The power of side projects in sparking career-defining moments

* How a move to Berlin shaped his career and personal growth.

* The evolving balance between tinkering and instant AI tools

* How product curiosity fuels resilience through industry shifts

Tune in for an engaging conversation filled with wisdom and humor, offering valuable advice for aspiring designers and entrepreneurs.

In this episode of Founder@50, Jeremy Toeman sits down with Neha Tiwari, whose career spans the golden days of Web 2.0 in San Francisco to leadership roles at CNET, IGN, YouTube, and Fandom. Neha is a gamer, storyteller, and media executive who now runs her own consultancy helping highly productive people get even more done.

She shares how she built a career that bridges creative vision with business results while championing underrepresented voices in gaming and media. She’s also the only person who can go toe-to-toe with him on quoting Arrested Development and somehow weaving them into everyday conversation.

The conversation ranges through candid reflections on leadership, inclusion, and finding the right balance between career ambition and personal values.

We cover:

* What made the Bay Area’s Web 2.0 scene so special and why trust in tech felt different then

* Her path from Cal’s Media Studies program through internships at TechTV and Current TV

* Lessons learned at CNET, Revision3, Justin.tv, IGN, and YouTube Gaming

* Why diversity in leadership is essential for creative and business success

* Building her consultancy during the pandemic to support women, BIPOC, and mission-driven brands

* How empathy, integrity, and cultural context can transform storytelling

* That there’s always money in the banana stand!

Whether you work in media, gaming, or are navigating your own career pivot, Neha’s story blends inspiration, practical insights, and sharp industry perspective.

In this episode Jeremy Toeman sits down with peer, mentor, and parenting friend Leslie Fine. Leslie is a behavioral scientist turned product leader/coach who’s been a Chief Scientist at Crowdcast and a VP Products at Salesforce. They discuss…

• How Leslie’s background in behavioral economics shaped her approach to product and team building

• Lessons from building B2B products that prioritize user empathy over feature bloat

• Why she believes understanding user psychology is the most underrated skill in tech

• How becoming a founder later in life helped her apply decades of experience with a fresh perspective

• The importance of asking better questions in product discovery and leadership

• What she’s learned from navigating high-growth environments and finding the right problems to solve

You’ll also hear how Leslie applies frameworks from behavioral science to everything from hiring to startup pivots and why slowing down might be the fastest way to get it right.

In this episode, Jeremy Toeman talks with Michael Stern, Managing Director at Kintegral Asset Management, about his journey from a programmer in a Los Alamos chemistry lab to being a startup founder to socially driven investor.

• How early work in chemical modeling led to DE Shaw, startups, and eventually socially responsible investing

• What happened when Michael had to choose between product market fit and personal values

• How he helped expose corporate fraud and turned it into one of his biggest trades

• Why he invests in story driven startups like Pi-Lit and Street Smarts VR• Why investing in stories matters more to him than spreadsheets and how he finds purpose driven startups with real world impact

• How his firm uses data and algorithms to generate market outperformance while maintaining strict environmental and social standards

You’ll also hear what climbing Mount McKinley taught him about discomfort, drive, and decision making and why he believes success means doing work you never have to apologize for.

In this episode, Jeremy Toeman catches up with longtime friend Tami Arnowitz who shares how she transformed five distinct careers into a consulting business that blends mission, strategy, and heart.

• How she moved from product management to mortgages to launching Good Questions Consulting

• Why each career shift was guided by values like autonomy, meaning, and flexibility

• How she helps Jewish nonprofits apply business thinking to mission-driven work

• What it means to reinvent yourself while raising four kids and staying relentlessly curious

• The power of saying yes before you're ready and the “oh well” mindset that helped her navigate risk and change• What she learned managing everything from baby product lines to market research and vocational education strategy

You’ll also hear how Tami leverages her Columbia MBA, coaching skills, and lived experience to guide organizations toward clarity, confidence, and better questions.