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.

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.