Run the Numbers

Mark McCaffrey, the CFO of GoDaddy, joins CJ to talk about the evolution of one of the most recognizable brands on the internet from domain registration to a full-service platform for small businesses. Mark sheds light on GoDaddy’s role in the entrepreneurial micro-startup ecosystem and how, after 21 years, GoDaddy has grown to 21 million customers. He describes the trends he’s identified in the formation of micro businesses, their adoption of AI, their survival rates, and why churn caused by failing small businesses doesn’t affect GoDaddy as much as you think it would. He also talks about the metrics that matter, what he tracks, what he discloses, and how he uses this to pursue customers with intent. He also explains how to not lose sight of the micro when the macro is so big, and lists the two things every company in the tech industry needs to do to achieve long-term success. Spoiler: one has to do with customer relationships.

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

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SPONSORS:

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.

Brex offers the world's smartest corporate card on a full-stack global platform that is everything CFOs need to manage their finances on an elite level. Plus they offer modern banking and treasury as well as intuitive expenses and accounting automation, bill pay, and travel. Brex makes it easy to control spend before it happens, automate annoying tasks, and optimize your finances. Find out how Brex can help you make every dollar count at brex.com/metrics.

Vanta's trust management platform takes the manual work out of your security and compliance process and replaces it with continuous automation. Over 9000 businesses use it to automate compliance needs across over 35 frameworks like SOC 2 and ISO 27001. Centralize security workflows, complete questionnaires up to five times faster, and proactively manage vendor risk. For a limited time, get $1,000 off of Vanta at vanta.com/metrics.

Tropic is an intelligent spend management solution that consolidates your spend data and processes into one unified offering, enabling insights and decisive action. It doesn’t just show you where the problems are—it helps you solve them. From spotting hidden optimization opportunities, like duplicative spend, to automating those painful procurement workflows, to giving you the best market data that turns every vendor negotiation in your favor. Tropic combines smart insights with real human expertise to keep you ahead of the curve. Visit tropicapp.io/mostlymetrics to learn how.

NetSuite provides financial software for all your business needs. More than 40,000 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 ✅, head to NetSuite https://netsuite.com/metrics and get the CFO’s Guide to AI and Machine Learning.

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. Whether it's multi-element arrangements, subscription renewals, or complex usage-based contracts, RightRev takes care of it all. That means fewer spreadsheets, fewer errors, and more time for your team to focus on growth. For modern revenue recognition simplified, visit rightrev.com and schedule a demo.

—

FOLLOW US ON X:

@cjgustafson222 (CJ)

—

TIMESTAMPS:

(00:00) Preview and Intro

(01:54) Sponsor – Planful | Brex | Vanta

(06:16) GoDaddy and the Entrepreneurial Micro-Startup Ecosystem

(07:40) The Origins of the GoDaddy Name

(09:08) GoDaddy’s Business Model and its Evolution

(11:45) The Strategic High Ground of Starting with the Domain

(12:58) Definition of a Micro-Business

(15:32) Sponsor – Tropic | NetSuite | RightRev

(19:15) The Mostly Metrics Domain Name

(21:50) Unsuccessful Businesses and Churn at GoDaddy

(27:07) Surprises from GoDaddy’s Data

(29:20) Customer Trends in Openness to AI

(30:45) Determining Which Metrics Matter and Which to Disclose

(34:31) Pursuing Customers with Intent

(35:44) When and How Mark Introduces a New Metric

(38:25) ARR Versus Bookings

(39:25) Retention Trends

(41:06) Two Things to Do in the Tech Industry for Long-Term Success

(45:47) How the Power of Relationships Led Mark to GoDaddy

(49:08) Long-Ass Lightning Round: Excel Spreadsheets

(49:44) Three Rules for Every Young Professional

(51:02) Finance Software Stack

(52:11) Craziest Expense Story

Welcome to the first episode on The Business of Mostly Metrics.

The CFO became a CEO. Pretty wild. The CEO of me.

During this series we’ll cover the following topics:

* Writing your story in reverse, which is what today is about

* How I lost $209,640 of my own money trying to start a marketplace business

* Quitting a job to be able to keep writing, leaving a million dollars of equity on the table, and getting my first CFO job

* Decoding my timeline from 0 to 50,000 subscribers and the tactics I used along the way to keep stacking wins

* How I monetize my business across sponsorships, paid subscriptions, and events

* Starting the podcast and climbing the guest ladder

* Where this might all go next

* And if you’re,, lucky I’ll tell you how much this business makes

So let’s go back through all these things that I’ve done to get to this point.

Ambereen Toubassy, the CFO of Airtable, has experience as an advisor, an investor, and an operator. In this episode, she joins CJ to talk about how this experience informs her role as a CFO. The two delve into the complexities of navigating investor feedback and how to take criticism without getting defensive. They also discuss how to build the right advisory network, red flags to watch for, and the importance of scaffolding your weaknesses with external expertise. The episode also highlights the value of specificity in the role of a finance leader. Ambereen shares insights from her extensive career, including her time at Quibi, explaining what she learned from this moonshot idea that didn’t work out as hoped and her approach to balancing fiduciary duties with the human side of leadership.

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

—

SPONSORS:

Brex offers the world's smartest corporate card on a full-stack global platform that is everything CFOs need to manage their finances on an elite level. Plus they offer modern banking and treasury as well as intuitive expenses and accounting automation, bill pay, and travel. Brex makes it easy to control spend before it happens, automate annoying tasks, and optimize your finances. Find out how Brex can help you make every dollar count at brex.com/metrics.

Vanta's trust management platform takes the manual work out of your security and compliance process and replaces it with continuous automation. Over 9000 businesses use it to automate compliance needs across over 35 frameworks like SOC 2 and ISO 27001. Centralize security workflows, complete questionnaires up to five times faster, and proactively manage vendor risk. For a limited time, get $1,000 off of Vanta at vanta.com/metrics.

Tropic is an intelligent spend management solution that consolidates your spend data and processes into one unified offering, enabling insights and decisive action. It doesn’t just show you where the problems are—it helps you solve them. From spotting hidden optimization opportunities, like duplicative spend, to automating those painful procurement workflows, to giving you the best market data that turns every vendor negotiation in your favor. Tropic combines smart insights with real human expertise to keep you ahead of the curve. Visit tropicapp.io/mostlymetrics to learn how

MUFG is the largest bank in Japan and a global banking powerhouse with a focus on empowering Growth and Middle Market stage companies in North America and Europe. MUFG provides comprehensive banking services for VC-backed, PE-backed, and public companies with revenues starting at $40M. The bank combines its global capabilities with deep operational understanding to help companies accelerate their growth trajectory. Contact group head Bob Blee at [email protected] to find out more.

NetSuite provides financial software for all your business needs. More than 40,000 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 ✅, head to NetSuite https://netsuite.com/metrics and get the CFO’s Guide to AI and Machine Learning.

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. Whether it's multi-element arrangements, subscription renewals, or complex usage-based contracts, RightRev takes care of it all. That means fewer spreadsheets, fewer errors, and more time for your team to focus on growth. For modern revenue recognition simplified, visit rightrev.com and schedule a demo.

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.

—

FOLLOW US ON X:

@cjgustafson222 (CJ)

—

TIMESTAMPS:

(00:00) Preview and Intro

(02:25) Sponsor – Brex | Vanta | Tropic

(06:55) What Ambereen Has Learned from Being an Investor

(10:53) Dealing with Investor Feedback

(18:09) Sponsor – MUFG | NetSuite | RightRev | Planful

(22:54) Tips for Not Taking Feedback Personally

(24:12) When to Bring Founders into Meetings with Investors

(25:52) Scaffolding Your Weaknesses

(30:59) Whether or Not to Pay More for Great Advisors

(34:12) How to Identify the Right Banker or Consultant

(35:13) Banker and Consultant Red Flags to Watch Out For

(39:11) “In the Particular Is Contained the Universal”

(42:42) How the Specific Plays a Role in the Job of a Finance Leader

(46:46) Quibi, the Moonshot Idea That Didn’t Land as Planned

(50:16) Fiduciary Responsibility When Things Don’t Go as Planned

(55:00) Long-Ass Lightning Round: A Career Mistake

(55:48) Advice to Younger Self

(57:14) Finance Software Stack

(58:26) Craziest Expense Story

In this episode, Dashlane’s David Lapter, a five-time CFO, joins CJ to discuss the challenges of steering high-growth companies. He breaks down the common blind spots that CFOs face, why many double down on their strengths and avoid their weaknesses, and how the Eisenhower Matrix helped him tackle his own gaps. David also gives his take on competitors and his philosophy of differentiating your org from theirs without demonizing them, as well as how they can be used for motivation. David shares insights on building high-functioning teams, when teams should move from overlapping responsibilities to more defined roles, how to simplify your OKRs to be more effective, and the nature of the ideal HR-CFO relationship. This episode is packed with valuable takeaways for finance leaders navigating the complexities of high-growth environments.

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

—

SPONSORS:

Vanta's trust management platform takes the manual work out of your security and compliance process and replaces it with continuous automation. Over 9000 businesses use it to automate compliance needs across over 35 frameworks like SOC 2 and ISO 27001. Centralize security workflows, complete questionnaires up to five times faster, and proactively manage vendor risk. For a limited time, get $1,000 off of Vanta at vanta.com/metrics.

Tropic is an intelligent spend management solution that consolidates your spend data and processes into one unified offering, enabling insights and decisive action. It doesn’t just show you where the problems are—it helps you solve them. From spotting hidden optimization opportunities, like duplicative spend, to automating those painful procurement workflows, to giving you the best market data that turns every vendor negotiation in your favor. Tropic combines smart insights with real human expertise to keep you ahead of the curve. Visit tropicapp.io/mostlymetrics to learn how

NetSuite provides financial software for all your business needs. More than 40,000 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 ✅, head to NetSuite https://netsuite.com/metrics and get the CFO’s Guide to AI and Machine Learning.

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. Whether it's multi-element arrangements, subscription renewals, or complex usage-based contracts, RightRev takes care of it all. That means fewer spreadsheets, fewer errors, and more time for your team to focus on growth. For modern revenue recognition simplified, visit rightrev.com and schedule a demo.

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.

Brex offers the world's smartest corporate card on a full-stack global platform that is everything CFOs need to manage their finances on an elite level. Plus they offer modern banking and treasury as well as intuitive expenses and accounting automation, bill pay, and travel. Brex makes it easy to control spend before it happens, automate annoying tasks, and optimize your finances. Find out how Brex can help you make every dollar count at brex.com/metrics.

—

FOLLOW US ON X:

@cjgustafson222 (CJ)

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TIMESTAMPS:(00:00) Preview and Intro

(01:52) Sponsor – Vanta | Tropic | Netsuite

(06:18) Identifying Blind Spots

(10:44) Hiring to Fill Your Blind Spots

(14:21) The Eisenhower Matrix and Prioritising Your Blind Spots

(17:15) Sponsor – RightRev | Planful | Brex

(20:58) The Traps of Execution Mode Syndrome

(26:37) David’s Philosophy on Speaking About Competitors

(31:09) Tips for Communicating How You’re Differentiated

(33:02) How Competitors Can Motivate Teams

(39:46) When to Move from Overlapping Responsibilities to More Defined Roles

(46:50) Simplifying OKRs

(52:16) The Urge to Copy the Goal Setting of Other Companies

(54:56) Should HR Report to the CFO?

(57:57) Long-Ass Lightning Round: A VAT Mistake

(01:00:21) Advice to Younger Self

(01:03:32) Finance Software Stack

(01:06:14) Craziest Expense Story

This is the CoreWeave IPO breakdown. I studied their S1 filing so you don’t have to.

What we’ll cover:

* What CoreWeave does

* Their business model

* Their financials

* Key themes heading into IPO

* Investors

* Bull, Bear and Base cases for the stock

This is not investment advice.

In this episode, CJ interviews Hanan Aharoni, CFO of Operative, who is an expert in operational excellence, particularly in private equity. Hanan shares insights on managing acquisitions and overcoming silos, inefficiencies, and decision paralysis in the process. He highlights the importance of having a clear org chart and a unified leadership team before discussing the critical role of culture in successful integrations. He breaks down how to spot inefficiencies, consolidate systems, and optimize costs without stifling innovation. He also sheds light on how the private equity model differs from the venture capital model in terms of allocating resources, managing debt, and being prepared for an exit or sale. This is a masterclass in private equity operations.

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SPONSORS:

Tropic is an intelligent spend management solution that consolidates your spend data and processes into one unified offering, enabling insights and decisive action. It doesn’t just show you where the problems are—it helps you solve them. From spotting hidden optimization opportunities, like duplicative spend, to automating those painful procurement workflows, to giving you the best market data that turns every vendor negotiation in your favor. Tropic combines smart insights with real human expertise to keep you ahead of the curve. Visit tropicapp.io/mostlymetrics to learn how.NetSuite provides financial software for all your business needs. More than 40,000 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 ✅, head to NetSuite https://netsuite.com/metrics and get the CFO’s Guide to AI and Machine Learning.

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. Whether it's multi-element arrangements, subscription renewals, or complex usage-based contracts, RightRev takes care of it all. That means fewer spreadsheets, fewer errors, and more time for your team to focus on growth. For modern revenue recognition simplified, visit rightrev.com and schedule a demo.

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.

Brex offers the world's smartest corporate card on a full-stack global platform that is everything CFOs need to manage their finances on an elite level. Plus they offer modern banking and treasury as well as intuitive expenses and accounting automation, bill pay, and travel. Brex makes it easy to control spend before it happens, automate annoying tasks, and optimize your finances. Find out how Brex can help you make every dollar count at brex.com/metrics.

Vanta's trust management platform takes the manual work out of your security and compliance process and replaces it with continuous automation. Over 9000 businesses use it to automate compliance needs across over 35 frameworks like SOC 2 and ISO 27001. Centralize security workflows, complete questionnaires up to five times faster, and proactively manage vendor risk. For a limited time, get $1,000 off of Vanta at vanta.com/metrics.

—

FOLLOW US ON X:

@cjgustafson222 (CJ)

—

TIMESTAMPS:

00:00 Preview and Intro

01:50 Sponsor – Tropic | Netsuite | RightRev

05:55 Hanan’s Impressive Career Rise to CFO

08:20 Overcoming Silos and Inefficiency When Scaling

10:46 Overcoming Inefficiency and Paralysis in M&A

15:50 Sponsor – Planful | Brex | Vanta

19:18 The Importance of Having a Clear Org Chart

22:07 “Vision Without Execution Is Just Hallucination”

25:33 Operational Excellence: Identifying Inefficiencies and Optimizing Costs

28:40 Acknowledging Biases

29:40 Using Industry Benchmarks

32:20 Balancing Optimizing Expenses and Preserving Innovation

35:16 Forming a Mitigation Plan

41:09 Areas Notorious for Inefficient Costs

42:56 Allocating Resources in a PE Model Versus a VC Model

45:57 How Debt Impacts How You Operate in PE

49:12 Tips for Finance Professionals Moving from VC to PE Models

50:48 Being Prepared for an Exit or Sale in a PE Environment

53:00 Long-Ass Lightning Round: A Massive Excel Spreadsheet Error

54:53 Advice to Younger Self: Fast Decisions

55:17 Finance Software Stack

55:55 Craziest Expense Story

Today’s guest went from being the CFO of a very large telecom company where he was meeting with ministers in Jordan to joining a team of just four people at a startup in Saudi Arabia. Abdullah Tahboub, CFO of Foodics, a cloud-based POS and restaurant management solution, joins CJ to talk about this leap and explain why he wishes he had joined the startup world sooner. The conversation delves into the differences between corporate and startup CFO roles. Abdullah also explores the rapid digital transformation in the food and beverage industry in the Middle East. He outlines Foodic's business model and evolution from cashier systems to payments, becoming a comprehensive fintech and SaaS company. He provides insights into the crawl-walk-run process of this business and how he balances growth in both the SaaS and payments aspects of the org.

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SPONSORS:

NetSuite provides financial software for all your business needs. More than 40,000 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 ✅, head to NetSuite https://netsuite.com/metrics and get the CFO’s Guide to AI and Machine Learning.

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. Whether it's multi-element arrangements, subscription renewals, or complex usage-based contracts, RightRev takes care of it all. That means fewer spreadsheets, fewer errors, and more time for your team to focus on growth. For modern revenue recognition simplified, visit rightrev.com and schedule a demo.

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.

Brex offers the world's smartest corporate card on a full-stack global platform that is everything CFOs need to manage their finances on an elite level. Plus they offer modern banking and treasury as well as intuitive expenses and accounting automation, bill pay, and travel. Brex makes it easy to control spend before it happens, automate annoying tasks, and optimize your finances. Find out how Brex can help you make every dollar count at brex.com/metrics.

Vanta's trust management platform takes the manual work out of your security and compliance process and replaces it with continuous automation. Over 9000 businesses use it to automate compliance needs across over 35 frameworks like SOC 2 and ISO 27001. Centralize security workflows, complete questionnaires up to five times faster, and proactively manage vendor risk. For a limited time, get $1,000 off of Vanta at vanta.com/metrics.

Tropic is an intelligent spend management solution that consolidates your spend data and processes into one unified offering, enabling insights and decisive action. It doesn’t just show you where the problems are—it helps you solve them. From spotting hidden optimization opportunities, like duplicative spend, to automating those painful procurement workflows, to giving you the best market data that turns every vendor negotiation in your favor. Tropic combines smart insights with real human expertise to keep you ahead of the curve. Visit tropicapp.io/mostlymetrics to learn how

—

FOLLOW US ON X:

@cjgustafson222 (CJ)

—

TIMESTAMPS:

00:00 Preview and Intro

02:27 Sponsor – RightRev | Planful | Brex

06:10 Abdullah’s Bold Career Move & Why CFOs Avoid Risks

09:56 Being a Corporate World CFO Versus a Startup CFO

16:03 Digital Transformation in the Food and Beverage Industry

17:54 Sponsor – Vanta | Tropic

21:38 Food & Beverage and Tech in the Middle East and North Africa

24:24 The Evolution of Foodics’ Business Model

31:35 How Lending Works in This Industry

34:55 Balancing Growth in SaaS and Payment Revenue Streams

37:21 Forecasting for Payments

40:30 Staffing for Both SaaS and Payments

42:27 The Most Difficult Part of Adding Payments

45:34 Long-Ass Lightning Round: Dealing with Underperformers

47:39 Advice to Younger Self

48:22 Finance Software Stack

49:03 Craziest Expense Story

State of the Private Markets delivers an insider’s look at the forces reshaping the pre-IPO landscape. In this episode, we break down the latest valuation surges and hiring trends, spotlight key moves from tech giants in security, HR tech, and legal automation, and dive into company updates from Wiz, Harvey, and Deel. We also cover major fundraising rounds and notable executive shifts that signal where the market is headed. Tune in for an in-depth analysis of the trends and shifts driving today’s private markets.

Thanks to our sponsor Netsuite. Visit netsuite.com/metrics for the CFO’s guide to machine learning.

Jim Cook, Netflix co-founder, former CFO of Mozilla, early employee at Inuit, executive coach, and author of Substack Cook’s Playbooks, returns to the podcast for the third time. In this episode, he breaks down the evolution of the role of CFOs from traditional scorekeepers to more strategic and operator roles, before looking ahead at what’s to come. This episode is packed full of helpful advice about transparency, building trust, authenticity in your executive role, and why “fake it till you make it” is actually bad advice. Looking at the future of the CFO role, Jim explains why he believes there will be no need for both COO and CFO roles in an organization, the biggest mistake a CFO can make at this time, and how CFOs should be adapting in order to succeed in this next era.

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SPONSORS:

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.

Brex offers the world's smartest corporate card on a full-stack global platform that is everything CFOs need to manage their finances on an elite level. Plus they offer modern banking and treasury as well as intuitive expenses and accounting automation, bill pay, and travel. Brex makes it easy to control spend before it happens, automate annoying tasks, and optimize your finances. Find out how Brex can help you make every dollar count at brex.com/metrics.

Vanta's trust management platform takes the manual work out of your security and compliance process and replaces it with continuous automation. Over 9000 businesses use it to automate compliance needs across over 35 frameworks like SOC 2 and ISO 27001. Centralize security workflows, complete questionnaires up to five times faster, and proactively manage vendor risk. For a limited time, get $1,000 off of Vanta at vanta.com/metrics.

Tropic is an intelligent spend management solution that consolidates your spend data and processes into one unified offering, enabling insights and decisive action. It doesn’t just show you where the problems are—it helps you solve them. From spotting hidden optimization opportunities, like duplicative spend, to automating those painful procurement workflows, to giving you the best market data that turns every vendor negotiation in your favor. Tropic combines smart insights with real human expertise to keep you ahead of the curve. Visit tropicapp.io/mostlymetrics to learn how.

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. Whether it's multi-element arrangements, subscription renewals, or complex usage-based contracts, RightRev takes care of it all. That means fewer spreadsheets, fewer errors, and more time for your team to focus on growth. For modern revenue recognition simplified, visit rightrev.com and schedule a demo.

—

FOLLOW US ON X:

@cjgustafson222 (CJ)

LINKS:

Cook’s Playbooks

www.benchboard.com

Jim Cook on LinkedIn

—

TIMESTAMPS:

(00:00) Preview and Intro

(01:37) Sponsor – Planful | Brex | Vanta

(05:49) CJ’s Career Growth Since First Interviewing Jim

(08:35) Making Finance Transparent

(14:40) Sponsor – Tropic | RightRev

(17:07) The Influence of Bill Campbell

(18:57) How to Get to Trust Faster

(20:32) Letting Your Freak Flag Fly in Your Executive Role

(23:06) Is “Fake It Till You Make It” Bad Advice?

(25:25) Why CFO Tenures Are Getting Longer

(28:16) The Evolution of the CFO Role and Technological Capability

(32:45) Scorekeeping and Actuals Don’t Matter Anymore

(34:38) The Era of the Strategic CFO

(36:48) SaaS and the Operator CFO Era

(41:09) Jim’s Prediction on the Next Era: The CFO Architect

(49:47) The Biggest Mistake We Could Make in This Era

(51:48) The Era of, “I Need a COO and a CFO,” Is Over

(55:41) Where a CFO Will Spend Most of Their Time in This Next Era

Today’s guest, Arvind Kadaba, the CFO of Aidoc, started his career as a high-profile investor before transitioning into the role of a CFO. He joins CJ to share his career journey and discuss the challenges he faced in transitioning into an operational role. The conversation explores the “grass is always greener” mentality that drives career shifts, and how to find the right career fit. Arvind describes the evolving landscape of healthcare technology and AI. He emphasizes the need for innovation and how to choose whether to build, buy, or partner to achieve this, giving listeners a masterclass in portfolio theory for operators. He also gives helpful tips for balancing short-term and long-term investments and explaining long-term shareholder value to employees. The episode concludes with Arvind defending his contrarian views that not all businesses should be venture-backed and not all great businesses are tech businesses.

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SPONSORS:

Brex offers the world's smartest corporate card on a full-stack global platform that is everything CFOs need to manage their finances on an elite level. Plus they offer modern banking and treasury as well as intuitive expenses and accounting automation, bill pay, and travel. Brex makes it easy to control spend before it happens, automate annoying tasks, and optimize your finances. Find out how Brex can help you make every dollar count at brex.com/metrics.

Vanta's trust management platform takes the manual work out of your security and compliance process and replaces it with continuous automation. Over 9000 businesses use it to automate compliance needs across over 35 frameworks like SOC 2 and ISO 27001. Centralize security workflows, complete questionnaires up to five times faster, and proactively manage vendor risk. For a limited time, get $1,000 off of Vanta at vanta.com/metrics.

Tropic is an intelligent spend management solution that consolidates your spend data and processes into one unified offering, enabling insights and decisive action. It doesn’t just show you where the problems are—it helps you solve them. From spotting hidden optimization opportunities, like duplicative spend, to automating those painful procurement workflows, to giving you the best market data that turns every vendor negotiation in your favor. Tropic combines smart insights with real human expertise to keep you ahead of the curve. Visit tropicapp.io/mostlymetrics to learn how

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. Whether it's multi-element arrangements, subscription renewals, or complex usage-based contracts, RightRev takes care of it all. That means fewer spreadsheets, fewer errors, and more time for your team to focus on growth. For modern revenue recognition simplified, visit rightrev.com and schedule a demo.

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.

—

FOLLOW US ON X:

@cjgustafson222 (CJ)

—

TIMESTAMPS:

(00:00) Preview and Intro

(02:21) Sponsor – Brex | Vanta | Tropic

(06:59) Transitioning from Investor to Operator

(11:13) The Problem-Specific Nature of Being an Operator

(14:29) Sponsor – RightRev | Planful

(16:39) Personal Product Market Fit

(23:18) “All You Need Is One”

(25:46) How Arvind Decided to Switch Careers

(33:07) The State of Healthcare Technology in AI

(36:05) Innovation: Build Versus Buy Versus Partner

(37:36) Portfolio Theory for Operators

(44:36) Explaining Long-Term Shareholder Value to Employees

(47:50) Not All Businesses Should Be Venture-Backed

(53:38) Not All Great Businesses Are Tech Businesses

(57:03) Long-Ass Lightning Round: Cross-Functional Trust

(58:04) Finance Software Stack

(58:54) Craziest Expense Story