Running the Long Game in Growth Equity | Larry Contrella

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