In this episode, we sit down with Ben Clark — former Amazon and KPMG leader, and recently exited founder — to break down how he built a fast-growing tech company with zero outside investment.

Ben shares the real strategy behind scaling through frugality, strong foundations, and hiring the best people, even when resources are limited. He talks about facing “cliff moments,” managing engineers, and making smart decisions when your needs grow faster than your team.

If you’re a founder trying to grow without funding, struggling with talent allocation, or navigating the early-stage grind, this episode gives you the mindset and tools to move forward with clarity.

In this episode of Fearless Founders, Ike returns to share what he learned building his second startup — and why the journey wasn’t any easier the second time around.

He breaks down the right time to raise funding, how early-stage founders can avoid common mistakes, and why managing engineers is more about clarity and communication than technical expertise.

From navigating the psychology of a second-time founder to building culture, dealing with stress, and staying focused on customer value, this conversation is packed with practical insights for anyone growing a startup.

Tune in for a candid breakdown of funding, leadership, engineering management, and the realities of building in the AI era.

In this episode of Fearless Founders, we dive into one of the most confusing decisions every founder faces — when to raise money and whether you should raise at all. Benoy and Ike break down the realities behind VC funding, from understanding if your business truly needs outside capital to navigating the distractions, trade-offs, and loss of control that come with investor expectations.

You’ll hear candid insights on identifying the right moment to take “other people’s money,” what VCs look for at each stage, how product-market fit dramatically changes the fundraising equation, and why some of the most successful founders bootstrapped their way to millions.

A practical, honest conversation on funding, focus, and scaling — and how to keep your head clear while managing engineers, growth, and the pressure to fundraise.

Why Prioritization is Your Superpower: A VC's Guide to Getting Funded and Scaling Smartly

In this packed episode of the Fearless Founder Podcast, we sit down with Benson Metcalfe, Managing Director and CEO of 2.0 Ventures, to gain a rare look inside the investor's playbook. With a career spanning high-level operations (Three Form, Saltstack), strategy consulting (Bain & Company), and private equity, Benson shares the core principles that guided him to launch his own $40 million venture fund.

Benson reveals the three critical pillars he and his team at 2.0 Ventures use to evaluate Seed and Series A companies, with the founder at the top of the list.

Inside this episode, you will learn:

1. People (The Founder): Beyond a "big vision," learn why coachability, gratitude, and true goal alignment are non-negotiable. Benson explains how a "vision exercise" helps him assess a founder's self-awareness and willingness to pivot.

2. Problem & Product: We discuss why your product must be a specific solution to a well-defined market problem and why 2.0 Ventures strictly avoids "pre-revenue" deals—traction is everything.

3. Financials & Forecasts: The path to turning VC money into massive returns.

• The Superpower: Benson reveals why he believes prioritization is the single most important skill for a CEO, using the "time, resources, scope" framework he learned at Bain. Learn how to say "no" to distractions and why a lack of focus is a "plague" in business.

• Embracing the Role of Salesperson: Every founder, regardless of background (engineer, product lead), is a full-time salesperson—selling the vision to investors, recruits, and customers daily.

• The Biggest Failure Risk: The one behavioral trait that ruins a founder's opportunity post-funding is the fear of sharing bad news. Benson advocates for a "red is good" culture of radical transparency, noting: "You learn more about yourself in recovery than you do in perfection."

• Process Over Results: Why focusing on a repeatable, scalable process (even when results fall short) is more important for long-term growth and building a truly durable company.

Benson emphasizes that founders should approach fundraising with the confidence of a peer, rather than a subordinate, to build a truly collaborative relationship. Don't miss this essential masterclass in scaling from a seasoned operator turned venture capitalist.

The Three Pillars of VC Investment:Essential Founder Advice:

Zero to $10MM ARR Without Funding - 2 Strategies to Consider

In this powerhouse episode of the Fearless Founder Podcast, we host Ryan, the CEO of Chiirp, who details his extraordinary, unconventional journey from dropping out of high school and fixing windshields to building a profitable, bootstrapped software company now pushing $10 million in ARR.

If you want to scale a business while maintaining profitability and avoiding the typical VC path, this episode is your blueprint. Ryan reveals the two fundamental strategies that made his zero-to-eight-figure growth possible: The 10X Mindset and Scaling Authenticity.

• Ditch Incrementalism: Ryan explains why striving for 2X growth is a trap. Instead, founders must adopt a "revolutionary standpoint" and ask: "How do I do something ten times bigger?"

• The Uncomfortable Advantage: Learn why bootstrapping—operating under pressure—is crucial to designing a profitable model, as discomfort forces your brain to create systems that don't rely on "throwing money at problems."

• The Comedian's Rule: Ryan shares the best advice he ever received from actor and comedian Pauly Shore: You must sell yourself first. "Nobody cares about your opinion... until they care about you as a person."

• Your Story is Your IP: See how Ryan converted his personal founder journey into a 45-minute video that became his perfect, automated sales pitch, ultimately selling $2 million worth of training and forming the core technology behind Chiirp.

• The Secret to Loyalty: Discover how the CEO’s willingness to be "in the trenches" and take the pain is the only way to earn loyalty, proving that "leadership requires pain."

Don't miss this masterclass in profitable scaling from a founder who proves you don't need a traditional background—or even outside investment—to build a multi-million dollar tech company.

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.