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

Wendy Laxton – Fund Accounting Explained: Why Grant Money Gets Spent Wrong

In this episode, James Kennedy sits down with Wendy Laxton, founder of Laxton CFO Services, to unpack the “modern” version of fund accounting – how nonprofits manage restricted vs. unrestricted funds, align grant requirements with real-world operations, and avoid credibility-killing misallocations. Wendy shares how the 2008 recession unexpectedly led her into fractional CFO work, why niching down to nonprofits was a defining move, and what she’s learned from guiding organizations through system complexity – from overbuilt ERPs to intentionally “resetting” in QuickBooks and rebuilding structure over time.

Listen Now »
Merushka Chetty

Kerry Peters – Microsoft MVP Exposes the #1 ERP Mistake Companies Make

In this episode, James Kennedy sits down with Kerry Peters, Microsoft MVP and Co-Founder of New View Strategies, to unpack why so many ERP implementations fail – and how businesses can finally get the financial clarity, process efficiency, and operational visibility they were promised.

Kerry shares how her unique blend of corporate controller experience, ERP expertise, and a passion for business process has helped hundreds of companies turn struggling implementations into scalable, high-performing systems. From a publishing company with 21,000 general ledger accounts to organizations stuck in endless month-end closes, Kerry explains the root causes, the fixes, and how to prevent the pain in the first place.

She also reveals how she unintentionally built a thriving fractional CFO practice – simply by helping companies bridge the gap between software, people, and process.

Listen Now »
Merushka Chetty

Shane Bender – Agency Finances Are BROKEN – 3 Blind Spots Killing Your Profits

In this episode, James Kennedy sits down with fractional CFO Shane Bender, founder of Bender CFO Services, to dig into the financial realities of running a marketing or digital agency. Using his love of weather models as a metaphor for forecasting, Shane explains why most agency owners are flying blind on margins, cash flow, and growth targets – and how better data, simple models, and discipline can turn chaos into clarity. From client-level profitability to weekly cash planning and “smarter” goals, this conversation is a practical roadmap for agencies that want to grow without blowing up their finances.

Listen Now »