409A Frequency and When to Update It

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.

—

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

—

RELATED EPISODES:

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

Portfolio Operations: This Is What You Actually Have To Do To Make Sure a Company Is Successful:

Brex COO/CFO Michael Tannenbaum on Taking Risks

996 Culture, Exploding AI Bills & SaaS Chaos

—

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

—

SPONSORS:

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

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

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.

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.

#RunTheNumbersPodcast #StartupFinance #VentureCapital #CFOInsights #Leadership

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com