In this episode of Run the Numbers, CJ Gustafson sits down with Larry Contrella, General Partner at JMI Equity, to unpack how JMI invests in software without financial engineering or roll-up strategies. Larry explains how the firm builds conviction through founder relationships, long-term partnership, and a product-and-brand-first view of durable growth. They discuss how JMI supports companies through scaling, why operating partners keep returning, and how underwriting looks different in mission-driven sectors like K–12 and nonprofit tech where customers are schools and communities, not Fortune 500s. Larry’s background as a competitive runner at Penn ties the conversation together with a clear ethos: patience, discipline, and playing the long game.

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LINKS:

Larry on LinkedIn: https://www.linkedin.com/in/larry-contrella-160a8a25/

JMI Equity: https://www.jmi.com/

CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/

Mostly metrics: https://www.mostlymetrics.com

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So You’re Looking for a “Strategic” CFO? Bloomerang’s Steve Isom on What That Really Means

https://youtu.be/cgHOtvG1Ces

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TIMESTAMPS:

00:00:00 Preview and Intro

00:02:49 Sponsors — Mercury | RightRev | Tipalti

00:06:41 Joining the JMI Conversation

00:07:13 College Running and Team Dynamics

00:08:13 New York Marathon Story and Career Intersection

00:11:04 Competitive Drive and Patience With Founders

00:12:54 Building Long-Term Partnerships and Underwriting Credibility

00:15:27 Growth Equity as a Long Sales Cycle

00:15:48 Sponsors — Aleph | Fidelity Private Shares | Sage Intacct

00:18:44 Fund Planning, Deal Pacing, and Board Commitments

00:20:59 Sourcing Philosophy and Developing Investors Over Time

00:22:09 Hustle as the Only Sustainable Edge in Sourcing

00:24:14 Early Sourcing Tactics and Information Arbitrage

00:26:06 Reputation, Experience, and Breaking Into Competitive Deals

00:29:42 Organic Growth Over Roll-Ups and M&A Discipline

00:32:51 Brand, Product Leadership, and Paying for the Best Businesses

00:33:29 Bloomerang and Brand-Led Growth in Nonprofit Software

00:34:46 Why JMI Operators Keep Coming Back

00:36:28 Collaborative Leadership and Giving Constructive Advice

00:38:20 Using Data Without Slowing Decisions

00:39:20 Transparency, Alignment, and Knowing Where You Stand

00:40:31 Why JMI Invests in K–12 and EdTech

00:42:07 Mission-Driven Businesses and Talent Advantage

00:43:24 Monetization Models in Nonprofit SaaS

00:45:40 Conviction Bets and Product-Market Fit Stories

00:48:49 Rethinking TAM and Expanding Markets Over Time

00:50:40 Lightning Round: Sourcing Stories and Lessons

00:52:58 Traits of Great Founders and Changing Beliefs

00:54:20 Closing Thoughts and Outro

#RunTheNumbersPodcast #GrowthEquity #B2BSoftware #FounderRelationships #PrivateEquity

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