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Cash Flow, Control, and Company-Building with Ivan Makarov of Andreessen Horowitz

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Oct 16, 2025

Guest

Ivan Makarov

In this discussion, Ivan Makarov, Operating Partner at Andreessen Horowitz and former VP of Finance at Webflow, shares invaluable insights on building finance functions in startups. He highlights critical points like when to transition from outsourcing to hiring in-house finance, the evolving role of early finance hires, and the importance of cash management. Ivan also warns against common fundraising pitfalls and emphasizes the need for strong audit readiness. Plus, he dives into how modern finance tools enhance operations and the necessity of protecting against fraud.

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ADVICE

Hire Based On Complexity, Not Revenue

Hire an in-house finance leader based on complexity, not revenue thresholds.
Bring finance in early for regulated, international, marketplace, or hardware businesses.

insights

INSIGHT

Business Operators Beat Pure Accountants

First finance hires today are often business-focused, not pure accounting hires.
Outsourced accounting plus a strategic operator is now a common, efficient setup.

insights

INSIGHT

Finance, FP&A And Ops Converge

Finance roles now merge FP&A, BI, and RevOps into a single function at startups.
Founders expect finance hires to use AI, build agents, and handle broad operational tasks.

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From Operator to Operating Partner

06:36 • 4min

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When to Hire In-House Finance

10:40 • 3min

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First Finance Hire Today vs. Ten Years Ago

14:08 • 5min

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What Founders Want in Early Finance Hires

19:07 • 2min

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Mapping Finance Tools to Financial Statements

21:05 • 4min

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Ideal Candidate Profile and Hiring Trends

24:38 • 3min

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Evolution of Financial Operations and Roles

27:54 • 4min

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First Year Priorities for New Finance Leaders

32:09 • 3min

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Audit Readiness and Choosing Auditors

35:06 • 1min

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Why Cash Management Is the Top Priority

36:27 • 3min

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Early Cash Controls and Bank Risk

39:23 • 2min

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Protecting Against Fraud and Phishing

41:31 • 2min

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Fundraising Pitfalls: Bad Metrics and Preparation

43:14 • 4min

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409A Frequency and When to Update It

47:20 • 3min

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Common Finance Tech Mistakes

50:29 • 1min

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Buying Finance Tools Earlier and Finance Hygiene

51:44 • 3min

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AI's Impact on Finance Labor and Workflows

54:48 • 4min

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What Makes a Successful Finance Offsite

58:21 • 4min

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Closing Remarks and Farewells

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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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

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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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#RunTheNumbersPodcast #StartupFinance #VentureCapital #CFOInsights #Leadership

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