Run the Numbers

Fintech Is Back: What’s Driving Valuations & Back-Office Convergence

Fintech is making a comeback, and the private markets are shifting fast. In this episode, we break down the biggest fintech moves—from Stripe’s $85B valuation jump to Klarna and Chime’s rumored IPOs—and explain why investors are paying up for some business models while discounting others.

Plus, we dive into a major shift in back-office software: HiBob’s acquisition of Mosaic signals a growing convergence between HR and finance, with implications for the future of ERP. Is the back-office stack consolidating into a new source of truth?

Topics we cover:✅ Why Stripe commands a 20x revenue multiple, and Mercury’s latest fundraise✅ Klarna vs. Chime: Who will get the better IPO valuation?✅ Affirm’s comeback—does it validate BNPL’s future?✅ The next evolution of back-office SaaS: HR meets FP&A

If you're a founder, operator, or investor in fintech or SaaS, this episode is packed with insights on positioning for the highest valuation.

🎧 Listen now and don’t forget to rate & review—first round’s on me if we ever meet in person.

This episode takes a deep dive into the business model of super app Grab as CJ interviews CFO Peter Oey. Peter introduces listeners to Grab and how it operates in Southeast Asia, highlighting the company’s journey from a ride-hailing service to acquiring Uber's operations in the region, expanding into food delivery, and even branching into banking services, all in one single super app. Peter explains why this model thrives in Southeast Asia and speculates on its potential in Western markets. He sheds light on the flywheel effect of branching into banking services, how they get customers to use Grab’s different products, and the advertising opportunities that exist for the platform. He also discusses how Grab has positively affected economic activity in the region and shares one customer’s incredible success story. The podcast concludes with insights into Grab's proprietary technology, including its unique mapping system, and advice for Western companies looking to enter the Southeast Asian market.

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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.

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.

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FOLLOW US ON X:

@cjgustafson222 (CJ)

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TIMESTAMPS:

(00:00) Preview and Intro

(02:15) Sponsor – Vanta | Tropic | RightRev

(05:54) Super Apps and Grab’s Business Model

(11:16) Why the Super App Model Thrives in Southeast Asia

(15:33) The Super App Model and Western Markets

(17:03) Sponsor – Planful | Brex

(19:16) The Role of Banking Services in Grab’s Business Model

(23:05) The First Step to Becoming a Fintech

(25:05) Getting Users to Use Multiple Grab Products

(30:31) The Advertising Opportunity for Grab

(32:14) Why Southeast Asia Is Overlooked as a Tech Hub

(35:30) Advice to Western Tech Companies Operating in Southeast Asia

(37:15) How Grab Increases Economic Activity

(40:51) A Grab Success Story

(41:45) Grab’s Proprietary Tech and Mapping System

(45:43) Long-Ass Lightning Round: A Forecast Accuracy Error

In this episode, CJ is joined by Kelly Mahncke, the CFO of USA Hockey, and the first CFO of a nonprofit to come on the show. They discuss the organization's business model and its revenue streams. Kelly emphasizes the importance of having a successful business whether it’s a nonprofit or not, and what she means when she says that there's no mission without margin. The conversation also covers USA Hockey's efforts to balance grassroots development with elite programs, the role of data and technology in enhancing operations, and the challenges of making hockey accessible to underprivileged communities. Kelly shares insights into the financial management of USA Hockey, including the for-profit and nonprofit aspects of the business, and how the four-year cadence of the Winter Olympics affects annual planning.

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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

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.

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FOLLOW US ON X:

@cjgustafson222 (CJ)

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TIMESTAMPS:

(00:00) Preview and Intro

(02:00) Sponsor – Tropic | RightRev | Planful

(06:23) The Companies Under the USA Hockey Umbrella

(07:50) Balancing Investing in Grassroots Development and Elite Teams

(10:01) USA Hockey’s Revenue Streams

(11:14) USA Hockey’s Data and IT

(13:07) Learnings from USA Hockey’s Data and Analytics

(16:38) Sponsor – Brex | Vanta

(19:10) Why Kids Should Try Different Sports

(20:03) Anecdotes About Hockey Players

(21:56) No Mission Without Margin

(23:40) The Most Surprising Line Items in USA Hockey’s Budget

(24:32) How the Winter Olympics Affects Annual Planning

(26:12) For-Profit Money in the Space

(29:14) The Business of Rink Ownership

(32:54) Making Hockey Accessible to Underprivileged Communities

(35:30) The For-Profit and Nonprofit Aspects of USA Hockey

(36:56) How Being a Nonprofit Impacts Hiring and Volunteers

(39:31) Lightning Round: Advice to Younger Self

(40:04) Technology at USA Hockey

(41:30) Finance Software Stack

(42:20) The Legacy Kelly Hopes to Leave

How Much Revenue Do You Need to IPO in 2024?

The IPO bar has risen—big time. In the 2010s, companies like RingCentral and Etsy went public with $100M-$250M in revenue. But today? You likely need $500M+ just to get a shot.

We’ll break down how IPOs evolved from the SaaS boom to the 2021 mega-deals (think Coinbase, Snowflake, and Airbnb), the 2022-23 freeze, and why 2024’s IPO class—Reddit, Klaviyo, Instacart—looks different.

Plus, we’ll preview 2025’s biggest potential IPOs, including Stripe, Databricks, and Deel. What’s the new rule? If you want to IPO, bring half a billion in revenue—or a damn good reason why you deserve to be public.

Visit mostlymetrics.com for more analysis like this

Serial CFO Michael Bayer, who is currently the CFO of Wasabi, joins CJ to share wisdom from his long career. He talks about his journey from being a “CF-no" to becoming a “CF-go” while emphasizing the importance of strategic investment to fuel hypergrowth companies. He breaks down the epochs of growth that a company goes through as it scales from driving revenue to focusing on cash flow. He highlights the significance of order of magnitude thinking and hiring for future needs. Michael also introduces his “rock-turning” exercise for identifying and addressing issues when joining a company, and shares his three guiding principles: speed is God, best ideas win, and if you’re not making mistakes, you’re not trying hard enough. The episode concludes with an insightful story about Van Halen's "brown M&M" clause, and what finance leaders can learn from it.

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SPONSORS:

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

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FOLLOW US ON X:

@cjgustafson222 (CJ)

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TIMESTAMPS:

(00:00) Preview and Intro

(02:16) Sponsor – RightRev | Planful | Brex

(06:02) The Reason for a Sloth Background

(08:31) A Company’s Epochs of Growth

(12:52) Staffing for the Different Epochs of Growth

(17:08) Sponsor – Vanta | Tropic

(21:29) The CF-No Versus CF-Go Mentalities

(23:42) The “Rule Of” Metric: EBITDA or Cash Flow

(27:05) The Rock-Turning Exercise

(29:12) The First Rock Michael Turns Over

(30:26) Forming Relationships Before Solving Problems

(32:08) The Time Factor in Becoming a Good CFO

(36:01) Michael’s Three Simple Rules for Being a Great CFO

(38:45) Creating Space for the Best Ideas

(41:18) What It Means to “Rent Capital”

(47:25) The Brown M&M Story

Erica Gessert, CFO of Upwork, and former Senior Vice President of Finance & Analytics at PayPal, joins CJ for this episode. They discuss Erica's experience with forecasting models at PayPal, emphasizing the need for adaptable models that change with economic conditions. Delving into her role at Upwork, Erica explains the company’s approach to customer acquisition costs, the significance of network effects in marketplace businesses, and Upwork’s take rate strategies. The conversation covers Upwork’s investment in R&D, how the company maintains platform trust in the face of bad actors, and the impact of AI. Apart from explaining how Upwork gained 20 points of EBITDA in just three quarters, Erica also sheds light on their North Star metrics, how they balance growth and profitability, their approach to M&A, and her experience reporting to Masayoshi Son during her time at Sprint.

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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.

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.

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.

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FOLLOW US ON X:

@cjgustafson222 (CJ)

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TIMESTAMPS:

(00:00) Preview and Intro

(02:30) Sponsor – Planful | MUFG | Brex

(06:17) Budgeting at PayPal

(10:23) Forecasting Methodologies at PayPal

(13:15) The Impact of the Calendar on Forecasting

(15:01) Forecasting and Macroeconomic Indicators

(16:29) Planning Will Take as Long as the Time You Allot for It

(17:56) Surprising Insights About Freelancers

(19:26) Sponsor – Vanta | Tropic | RightRev

(24:55) Upwork’s Customer Acquisition Cost

(27:59) Freelancers and AI Adoption

(29:07) Network Effects in Upwork’s Model

(31:14) Upwork’s Take Rate Strategies

(34:49) R&D Investing at Upwork

(38:36) Selling Trusted Transactions

(41:12) Upwork’s North Star Metrics

(42:59) Recognising the Potential of AI

(44:05) How Upwork Gained 20 Points of EBITDA in Three Quarters

(45:29) Balancing Growth and Profitability

(46:41) Upwork’s M&A Strategy

(48:35) Long-Ass Lightning Round: A Big Career Mistake

(50:55) Reporting to Masa from SoftBank

(52:49) Advice to Younger Self

(54:18) Finance Software Stack

(54:55) Craziest Expense Story

Hey everyone, welcome back to the show! Last week, our report and podcast on the state of private markets went absolutely bonkers. So, we’re building on that momentum today and giving you even more private tech company headlines.

The goal? By the end of this episode, you’ll feel like you have a backstage pass to the best companies before they hit the public markets—and you’ll sound like the smartest person in the room next time you’re talking to colleagues (hopefully not over Microsoft Teams, because let’s be real, that thing sucks). Honestly, the U.S. government should ban Teams before they ban TikTok. But I digress.

A lot happened in the tech market this week when it comes to valuations, efficiency metrics, and overall financial performance, so let’s get into it.

* X (Formerly Twitter) Profits Surge, But Revenue Tells a Different Story

* Deel’s Breakneck Growth and Market Positioning

* Clay’s Valuation Jump Raises Eyebrows in the Data Space

Hit subscribe, share this with your favorite estranged family member, and give us five stars (it would mean a lot to me).

mostlymetrics.com

In this episode, CJ is joined by Kapil Agrawal, CFO at Outschool, former CFO of Poshmark, and former Global Head of Pricing and Finance Business Partner at Uber. Kapil shares insights on Uber's pricing strategies and the use of promotions to drive customer growth. He discusses the multiple North Star metrics used at Uber before explaining his role in changing the company’s take rate. He also talks about his role at Poshmark and how he raised the company’s gross margin. The conversation explores the advantages and challenges of marketplace models versus subscription models and highlights the potential of combining both. Also covered is the significance of high-quality decision-making as a leader and the role of hard work in achieving this.

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SPONSORS:

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.

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)

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TIMESTAMPS:

(0:00) Preview and Intro

(02:50) Sponsor – MUFG | Brex | Vanta

(07:15) Discounting and Promotions at Uber

(09:26) Pros and Cons of Acquiring Customers with Promotions

(13:48) How Uber Determined the Promotion Term of Nine Months

(14:33) Promotional Launch Strategies Across Different Uber Platforms

(17:49) Sponsor – Tropic | RightRev | Planful

(21:10) The Multiple North Star Metrics at Uber

(24:31) Retention for Drivers Versus Passengers

(25:25) Tackling the Competition for Drivers

(27:20) Changing Uber’s Take Rate

(31:55) Raising the Gross Margins at Poshmark

(37:53) Moving from Buyer and Seller Cohorts to User Cohorts

(39:20) Poshmark’s Take Rate

(42:46) Intro to Outschool

(43:20) Transaction-Based Models Versus Subscription-Based Models

(45:04) The Role of Capital Allocation

(47:22) Combining Transaction-Based and Subscription-Based Models

(49:45) Being Judged on the Quality of Your Decisions

(54:00) Hiring: Generalists Versus Specialists

(56:06) Long-Ass Lightning Round: A Price Cut Regret

(57:34) Advice to Younger Self

(58:44) Finance Software Stack

(59:28) Craziest Expense Story

In this episode, CJ interviews Nigel Glenday, CFO, COO, and board member at Masterworks, a company that allows investors to buy shares in high-value artworks. He sheds light on the art market and Masterworks’s business model. They discuss the intricacies of art as an asset class, its historical significance, and its potential as an investment. Nigel explains the process of securitizing art, comparing it to other unique asset classes like racehorses and athlete contracts. He highlights the importance of data in valuing art and the company's approach to managing a large portfolio of art investments, before discussing the evolution of Masterworks' business model. The episode provides insights into the unique aspects of this asset class and the innovative ways Masterworks is scaling its business.

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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

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)

—

TIMESTAMPS:

(00:00) Preview and Intro

(02:23) Sponsor – Vanta | Tropic

(04:53) Overcoming the Thomas Crown Affair

(06:22) Finance Within the Art World

(07:34) The Most Expensive Piece of Art Ever Purchased

(09:15) The History of Art as an Asset Class

(10:51) The Data-Rich Nature of Trading Art

(12:46) The Performance of the Art Market Compared to Other Markets

(15:37) Emotional Dividends in Art Investing

(17:13) Sponsor – RightRev | Planful | Brex

(20:55) Securitizing Anything with a Cash Flow

(24:45) Securitizing Art

(27:28) Determining When to Sell

(30:03) Museums: Owned Versus Loaned

(30:55) Masterworks’ Revenue Streams

(34:21) How Masterworks Services Their Investors

(36:06) Data and How It Informs What Masterworks Buys and Sells

(41:55) Evaluating the Value of the Art

(43:04) The Trading Market

(44:59) The Scaling and Evolution of Masterworks

(49:24) Long-Ass Lightning Round: Auto-Renewal Contract Mistakes

(50:43) Advice to Younger Self: No Style Points

(53:52) Finance Software Stack

(57:31) Craziest Expense Story: Defend Your Spend

This is our inaugural State of the Private Markets, a monthly series where we’ll deliver the most compelling valuation, hiring, and revenue insights on pre-IPO candidates. Think of this as your backstage pass to the companies shaping the future before they hit the public markets.

Today we will cover:

* Valuation: The most valuable private tech companies

* Hiring: The fastest hiring companies

* Layoffs: The companies shedding headcount

* Sector specific highlights: This month we check in on Foundational Models, Fintech, and Autonomous Driving

* Company spotlights: This month we check in on DataBricks, Anduril, and Canva

* Fundraising: Recent rounds you should know about

* Execs: Pre IPO CFO hires