In this episode of Fearless Founders, CTO Keith Deutsch challenges the common misconceptions around AI, arguing why today’s generative models are mis-labelled and misunderstood. With decades of experience, Keith unpacks the realities of integrating these technologies, the architectural shifts required, and where founders often go wrong.

Gain practical insights on building the right technical team, using AI effectively, and scaling your product without falling for the hype.

In this Episode 32 of Fearless Founders, we welcome Ashley Leonard, a serial entrepreneur, tech innovator, and founder of Syxsense who has successfully exited three companies. Ashley shares his unconventional, what he calls “devious”—approach to testing product-market fit before building a product, along with hard-won lessons on scaling, resilience, and creating a business flywheel.

Tune in for candid insights on navigating setbacks, building revenue engines, and turning challenges into opportunities for lasting success.

In this episode of Fearless Founders, Ike & Benoy sit down with MIT-trained CTO Keith Deutsch, who has helped shape over 30 startups from the ground up. Keith shares hard-earned insights on building successful tech products, navigating founder blind spots, and avoiding costly missteps between version 1 and version 2. Whether you're a first-time founder or scaling your startup, this conversation is packed with lessons you won't want to miss.

In Episode 30 of Fearless Founders, we sit down with Adam Nugent, founder of Foresight Wealth Management, who scaled his firm to $1.4 billion in assets—only to lose it all.

Adam opens up about the collapse of his business, the emotional aftermath, and his journey through rock bottom toward personal and professional reinvention. From the pitfalls of chasing external validation to the power of rebuilding your identity, this conversation is packed with hard-won wisdom for every entrepreneur navigating risk, growth, and purpose.

In Episode 29 of Fearless Founders, Abby Martin a veteran HR leader, former Googler, and President of Amplēo HR shares her transformative insights on building high-performing teams. With nearly two decades of experience across big tech and startups, Abby lays out her 6.5 guiding “rules” for founders navigating leadership, scaling, and culture-building.

From debunking the “we’re a family” myth to tackling clarity, delegation, and tough conversations, this episode is packed with candid advice for startup leaders looking to grow without chaos. A must-listen for any founder serious about getting their people strategy right.

In this episode 28 of Fearless Founders, Brock Blake, co-founder and CEO of Lendio, shares the unfiltered reality behind building a $100M business. He walks us through five pivotal “fetal position” moments—those gut-wrenching lows that tested his resolve, leadership, and belief in the mission.

From near financial collapse to the emotional toll of high-stakes decision-making, Brock offers a powerful reflection on endurance, team loyalty, mentorship, and the role of personal well-being in entrepreneurial success.

In Episode 27 of Fearless Founders, we sit down with Fengmin Gong, a pioneering technologist and four-time exited founder, known for his instrumental roles in building companies like Palo Alto Networks and CipherOptics.

He shares his incredible journey from rural China to Silicon Valley, navigating research, entrepreneurship, and leadership across five startups. Learn how Gong transitioned from academia to business, built teams, and consistently delivered high-impact cybersecurity innovations. This episode is packed with timeless advice for technical founders and aspiring entrepreneurs looking to scale from idea to exit.

In this episode of Fearless Founders, Jeremy Glauser, a three-time exit entrepreneur, shares his journey of building and scaling multiple businesses. He opens up about the challenges of entrepreneurship, from navigating market timing to the emotional toll of setbacks.

Jeremy discusses how innovation often emerges from crisis, revealing how a major financial downturn nearly derailed his company and how a strategic pivot saved it. He also explores the balance between ambition and well-being, offering insights on resilience, leadership, and sustainable success. Don't miss this compelling conversation on overcoming adversity and thriving as a founder.