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September 5, 2025

Kyle Gasaway – How We Got Acquired by IBM Using Only QuickBooks

James Kennedy welcomes Kyle Gasaway, founder of Unicorn Group, to unpack the myths and realities of ERP implementations and why many startups don’t need them nearly as early as they think. Kyle shares candid lessons from years as a Big Four auditor, controller, and startup CFO – covering failed NetSuite and Sage Intacct rollouts, QuickBooks-powered exits (including an IBM acquisition), and his framework for keeping finance stage-appropriate. He also explains how fractional CFOs can maximize value through equity strategy, pricing discipline, and simplicity in systems
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  • 45.09 min
  • 2025-07-21
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Show Notes

James Kennedy welcomes Kyle Gasaway, founder of Unicorn Group, to unpack the myths and realities of ERP implementations and why many startups don’t need them nearly as early as they think. Kyle shares candid lessons from years as a Big Four auditor, controller, and startup CFO – covering failed NetSuite and Sage Intacct rollouts, QuickBooks-powered exits (including an IBM acquisition), and his framework for keeping finance stage-appropriate. He also explains how fractional CFOs can maximize value through equity strategy, pricing discipline, and simplicity in systems!!!

About Kyle Gasaway

A CPA and former KPMG auditor, Kyle is the son of two CFOs and has spent his career straddling public accounting and high-growth startups. After seeing too many companies over-invest in back-office systems too early, he founded Unicorn Group, a fractional CFO firm dedicated to helping Colorado founders and funders build strong financial foundations from seed through Series B.

What You’ll Learn

  • ERP Pitfalls: Why 75% of ERP projects miss expectations, and why “stage-appropriate” systems matter more than shiny software.
  • QuickBooks to Exit: How clean reporting and Excel modeling – not ERP – enabled multiple successful exits, including an IBM acquisition.
  • Equity & 409A Valuations: How assumptions drive outcomes, and why founders must actively manage their valuation narrative.
  • Pricing & Retention: Balancing growth with customer lifetime value and avoiding churn traps.
  • Fractional CFO Value: Equity, pricing, and system simplicity as the three areas that can unlock or destroy shareholder value.
  • Colorado Focus: Why Kyle works exclusively with local founders and the importance of aligning people with businesses they believe in.

Episode Highlights

  • “ERP at the wrong stage is toxic Kool-Aid. Keep it simple until you truly need scale.”
  • “Knowing the bare minimum for an audit is gold. You don’t waste time on noise.”
  • “IBM didn’t care that we were on QuickBooks. They cared the reports were accurate.”
  • “Retention is the real growth metric. Selling at all costs creates churn disasters.”
  • “Equity isn’t just compliance – it’s strategy. Manage your 409A, don’t let it manage you.”

More About Kyle’s Role

Through Unicorn Group, Kyle partners with pre-seed to Series B companies to deliver fractional CFO leadership:

  • Reporting cadence & financial modeling
  • Pricing and retention analysis
  • Equity management strategy
  • Stage-appropriate tooling and process design
    His goal is to maximize shareholder value while keeping finance lean, simple, and growth-ready.

Resources Mentioned

  • QuickBooks – still king for early-stage SaaS
  • Bill.com – Kyle’s go-to for AP/AR
  • Carta – equity management and employee engagement
  • Justworks (PEO) – streamlined payroll & compliance
This podcast is tagged under:

The Gross Profit Podcast

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