January 8, 2025

Why Most Founders Fail at Fundraising

In this episode of the Gross Profit Podcast, host James Kennedy sits down with Jason Shapiro, CEO and Founder of eighty2i. Jason shares his insights on how being a teacher – and a background in finance – ended up cultivating his passion for coaching founders.
The Gross Profit Podcast
The Gross Profit Podcast
Why Most Founders Fail at Fundraising
Loading
/

Show Notes

In this episode, James sits down with Jason Shapiro, CEO and Founder of eighty2i. With a unique blend of experience in teaching and finance, Jason shares how his journey cultivated a passion for coaching founders and empowering them to achieve their entrepreneurial goals.

What You’ll Learn:

  • The Teacher’s Edge: How Jason’s background as an educator influenced his approach to coaching founders and teams.
  • Bridging Entrepreneurial Gaps: The common challenges that hold entrepreneurs back and how eighty2i’s unique model provides hands-on solutions.
  • The Power of Radical Transparency: Why actionable feedback and candid advice are essential for business growth.
  • Sweat Equity in Action: How eighty2i’s flexible, tech-enabled support empowers founders to scale with confidence.

Episode Highlights:

  • “Entrepreneurship is inherently a team sport, and founders often need a co-pilot to help navigate the complex terrain of growth.”
  • “We don’t sugarcoat our advice because honest feedback leads to real change.”
  • “The best businesses start with sweat equity—yours and the people who believe in your vision.”

About eighty2i
Eighty2i takes the concept of a co-founder to the next level by offering flexible, tech-enabled strategic support across all functional areas of a business. Their team of seasoned operators provides hands-on assistance in RevOps, Finance, Private Equity, and Marketing, making entrepreneurship easier for founders, their teams, and their investors.

Key features of eighty2i’s approach include:

  • Flexible Collaboration: Clients can adjust the level of input in real-time.
  • Candid Advice: No sugarcoating, just actionable feedback that drives growth.
  • Sweat Equity Model: A commitment to working alongside founders to help them reach their full potential.
This podcast is tagged under:

The Gross Profit Podcast

More Episodes

Merushka Chetty

Aldo Aprile -Why Restaurants REALLY Fail

In this episode, James Kennedy sits down with Aldo Aprile, CPA and founder of Aprile CPA, to explore why every fractional CFO needs a close partnership with a tax expert – and why savvy business owners should plan taxes year-round, not just at filing time. Drawing on Aldo’s upbringing in a Peruvian family restaurant, his stints at GE, AmEx, PF Chang’s and more, they dig into restaurant prime-cost math, setting performance incentives, and the critical tax-planning moves that can save entrepreneurs tens of thousands each year.

Listen Now »
Merushka Chetty

Christophe Gantzer – Swiss Expert: Your Supply Chain Will Fail

In this episode, James Kennedy sits down with Christophe Gantzer, fractional CFO and co-founder of Clear Edge, to unpack the seismic shift in ESG and sustainability reporting across Europe – and what it means for Swiss and EU businesses alike. Drawing on his 20+ years in finance and his unique perspective as a French expat in Switzerland, Christophe explains the new CSRD/ESRS framework, how non-financial KPIs are now a finance function imperative, and why risk management must expand to cover environmental and social “debts.” Along the way, he shares real-world examples – from chocolate price shocks to cyber-risk parallels – that illustrate why CFOs can no longer sit on the sidelines of sustainability.

Listen Now »
Merushka Chetty

Scott Clements – The Outsourcing Secret NOBODY is Talking About!

James Kennedy welcomes Scott Clements, co-founder of Park Financial LLC and seasoned fractional CFO, to explore how he’s built a coast-to-coast advisory practice using online tools, joint ventures and strategic partnerships. Drawing on his unique journey – from EY auditor to high-school math teacher and back into finance – Scott reveals how he leverages technology and referral networks to serve clients nationwide. He also shares the systems he uses to manage feast-or-famine cash flows, balance in-house versus outsourced talent, and position his firm for steady, sustainable growth.

Listen Now »