Unusual Expense Requests and Business Humor

In this bucket list interview, CJ speaks with Larry Roseman, the CFO of Thumbtack, who shares his deep understanding of running marketplace businesses at scale. They explore Thumbtack's business model and monetization strategy, discussing the customer acquisition cost for both service providers and homeowners. Larry explains why going broad rather than niche can be fundamental for marketplace success, offering a counterintuitive view to that of many marketplace experts. He also talks about the flywheels Thumbtack has developed over time and the company’s shift towards becoming a proactive operating system for homes instead of a reactive marketplace. Additionally, Larry offers valuable insights on value creation from a CFO's perspective, emphasizing the importance of making NPV-positive decisions and the strategic role of the CFO in guiding big business decisions. Hear about the crises that Larry has seen in his career and his advice to “never waste a good crisis”.

If you're looking for an ERP head to NetSuite: https://netsuite.com/metrics and get a customized KPI checklist.

—

SPONSORS:

NetSuite provides financial software for all your business needs. More than 37,000 thousand companies have already upgraded to NetSuite, gaining visibility and control over their financials, inventory, HR, eCommerce, and more. If you're looking for an ERP platform ✅ NetSuite: https://netsuite.com/metrics and get a customized KPI checklist. 

Maxio is the only billing and financial operations platform that was purpose built for B2B SaaS. They're helping SaaS finance teams automate billing and revenue recognition, manage collections and payments, and put together investor grade reporting packages. 🚀 Request a demo at www.maxio.com/runthenumbers for 10% off your first year.

Leapfin is accounting automation software that automatically prepares and posts reliable journal entries. High-growth businesses like Reddit, Canva, and Seat Geek choose Leapfin to eliminate manual tasks, accelerate month-end close, and enable accounting leaders to provide faster insights to help their companies grow. To automatically standardize your revenue data with measurable business impact, check out leapfin.com today. 

Planful is a financial performance management platform designed to streamline financial tasks for businesses. It helps with budgeting, closing the books, and financial reporting, all on a cloud-based platform. By improving the efficiency and accuracy of these processes, Planful allows businesses to make better financial decisions. Find out more at www.planful.com/metrics.

Mercury is the fintech ambitious companies use for banking and all their financial workflows. With a powerful bank account at the center of their operations, companies can make better financial decisions and ensure that every dollar spent aligns with company priorities. That's why over 100K startups choose Mercury to confidently run all their financial operations with the precision, control, and focus they need to operate at their best. Learn more at mercury.com.

Mercury is a financial technology company, not a bank. Banking services provided by Choice Financial Group and Evolve Bank & Trust®; Members FDIC.

—

FOLLOW US ON X:

@cjgustafson222 (CJ)

—

TIMESTAMPS:(00:00) Preview and Intro(02:31) Sponsor – NetSuite | Maxio(06:13) How Thumbtack Makes Money(09:30) Being Broad as the Key to Marketplace Success(12:31) Charging for the LTV(13:45) The Evolution of the Marketplace Industry(16:21) Sponsor – Leapfin | Planful | Mercury(19:40) Thumbtack’s Two North Stars(21:31) CAC and LTV: Supplier versus Household(23:59) Flywheels versus Network Effects(25:52) Thumbtack’s Evolution: Reactive to Proactive(29:09) Thumbtack’s North Star Metric(32:34) Making the Right NPV Positive Decision(36:43) Helping the C-suite Size Up Big Bets(39:20) Learnings from Crises(40:44) Share-Based Compensation(45:37) Long-Ass Lightning Round: CAC Framework Regrets(50:33) Finance Software Stack(51:53) Craziest Expense Story