In this episode of Run the Numbers, CJ Gustafson sits down with Ivan Makarov, Operating Partner at Andreessen Horowitz and former VP of Finance at Webflow, to explore what it takes to build a finance function from scratch inside a fast-growing startup. Ivan shares lessons from the trenches—how to decide between outsourcing and hiring in-house, what makes a great first finance hire, and why early-stage companies often run out of cash before they run out of ideas. He also dives into fundraising pitfalls, audit readiness, and the tools that make up a modern finance stack. Beyond the spreadsheets, Ivan opens up about the shift from operator to venture partner, the value of helping founders avoid his past mistakes, and what makes an offsite actually work.

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LINKS:

Ivan Makarov on LinkedIn: https://www.linkedin.com/in/ivansmakarov/

Andreessen Horowitz: https://a16z.com/

CJ on X (@cjgustafson222): https://x.com/cjgustafson222

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

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Webflow’s VP Finance Ivan Makarov on Understanding Startup Equity:

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Brex COO/CFO Michael Tannenbaum on Taking Risks

996 Culture, Exploding AI Bills & SaaS Chaos

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TIMESTAMPS:

(00:00:00) Preview, Intro

(00:01:18) Meet Ivan Makarov of Andreessen Horowitz & Episode Setup

(00:02:39) Sponsor – Tipalti | Aleph | Rillet

(00:06:51) From Webflow to Andreessen: Becoming an Operating Partner

(00:09:19) When and Why Founders Hire Their First Finance Leader

(00:12:52) Hiring Early in Complex or Regulated Industries

(00:13:58) The First Finance Hire in 2025 vs. 2015

(00:15:46) Sponsor – Fidelity Private Shares | Mercury | RightRev

(00:19:02) The Many Hats of Finance Leaders & The Rise of RevOps

(00:24:55) What Founders Look For: Startup DNA and Work Ethic

(00:26:05) Grind Culture, Return to Office, and New Expectations

(00:28:20) From BizOps to RevOps: How Finance Roles Are Evolving

(00:31:57) The First 12 Months of a Finance Leader’s Playbook

(00:35:05) Choosing Audit Partners and Avoiding Hidden Costs

(00:36:32) Why Startups Really Fail — Running Out of Cash

(00:39:16) Cash Controls, Banking Diversification, and Fraud Prevention

(00:43:48) Fundraising Red Flags: Metrics, Definitions, and Diligence

(00:47:50) 409A Valuations, Equity Clarity & Candidate Questions

(00:50:09) The Modern Finance Tech Stack & Gen 3 Tools

(00:55:05) AI’s Impact: Replacing Labor, Not People

(01:00:00) Offsites, Team Building & The Future of Finance Leadership

(01:02:28) Wrapping Up: Reflections, Gratitude & Closing Credits

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SPONSORS:

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Rillet is the AI-native ERP modern finance teams are switching to because it’s faster, simpler, and 100% built for how teams operate today. See how fast your team can move. Book a demo at https://www.rillet.com/metrics

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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

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#RunTheNumbersPodcast #StartupFinance #VentureCapital #CFOInsights #Leadership

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