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. — SPONSORS: Mercury is business banking built for builders, giving founders and finance pros a financial stack that actually works together. From sending wires to tracking balances and approving payments, Mercury makes it simple to scale without friction. Join the 200,000+ entrepreneurs who trust Mercury and apply online in minutes at https://www.mercury.com RightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. For RevRec that auditors actually trust, visit https://www.rightrev.com and schedule a demo. Tipalti automates the entire payables process—from onboarding suppliers to executing global payouts—helping finance teams save time, eliminate costly errors, and scale confidently across 200+ countries and 120 currencies. More than 5,000 businesses already trust Tipalti to manage payments with built-in security and tax compliance. Visit https://www.tipalti.com/runthenumbers to learn more. Aleph automates 90% of manual, error-prone busywork, so you can focus on the strategic work you were hired to do. Minimize busywork and maximize impact with the power of a web app, the flexibility of spreadsheets, and the magic of AI. Get a personalised demo at https://www.getaleph.com/run Fidelity Private Shares is the all-in-one equity management platform that keeps your cap table clean, your data room organized, and your equity story clear—so you never risk losing a fundraising round over messy records. Schedule a demo at https://www.fidelityprivateshares.com and mention Mostly Metrics to get 20% off. Sage Intacct is a cloud financial management platform that replaces spreadsheets, automates workflows, and keeps your books audit-ready as you scale. It unifies accounting, ERP, and real-time reporting for finance, retail, logistics, tech, and professional services. With payback in under six months and up to 250% ROI, and eight years as the customer-satisfaction leader, Sage Intacct helps you take control of your growth: https://bit.ly/3Kn4YHt — 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 — RELATED EPISODES: Is taking a company public even worth it? | Fullstory’s Chad Gold https://youtu.be/zSD8y9dr4Vg So You’re Looking for a “Strategic” CFO? Bloomerang’s Steve Isom on What That Really Means https://youtu.be/cgHOtvG1Ces — 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 This is a public episode. 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