Mostly metrics: Run the Numbers Podcast

The CFO Rule for AI Forecasting: “It’s Not Zero” | Dan Griggs

CJ Gustafson — Thu, 29 Jan 2026 10:02:50 GMT

In this episode of Run the Numbers, CJ sits down with Dan Griggs, CFO of Intercom, to break down how finance leaders should think about pricing, forecasting, and resource allocation in the AI era. Dan explains why “it’s not zero” is his guiding forecasting principle, how Intercom landed on 99 cents per AI resolution for Fin, and what it means to build an AI product that could eventually cannibalize a successful SaaS core. A candid look at managing uncertainty while still making bold bets.

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SPONSORS:

Brex is an intelligent finance platform that combines corporate cards, built-in expense management, and AI agents to eliminate manual finance work. By automating expense reviews and reconciliations, Brex gives CFOs more time for the high-impact work that drives growth. Join 35,000+ companies like Anthropic, Coinbase, and DoorDash at https://www.brex.com/metrics

Metronome is real-time billing built for modern software companies. Metronome turns raw usage events into accurate invoices, gives customers bills they actually understand, and keeps finance, product, and engineering perfectly in sync. That’s why category-defining companies like OpenAI and Anthropic trust Metronome to power usage-based pricing and enterprise contracts at scale. Focus on your product — not your billing. Learn more and get started at https://www.metronome.com

RightRev is an automated revenue recognition platform built for modern pricing models like usage-based pricing, bundles, and mid-cycle upgrades. RightRev lets companies scale monetization without slowing down close or compliance. For RevRec that keeps growth moving, visit https://www.rightrev.com

Rillet is an AI-native ERP built for modern finance teams that want to close faster without fighting legacy systems. Designed to support complex revenue recognition, multi-entity operations, and real-time reporting, Rillet helps teams achieve a true zero-day close—with some customers closing in hours, not days. If you’re scaling on an ERP that wasn’t built in the 90s, book a demo at https://www.rillet.com/cj

Tabs is an AI-native revenue platform that unifies billing, collections, and revenue recognition for companies running usage-based or complex contracts. By bringing together ERP, CRM, and real product usage data into a single system of record, Tabs eliminates manual reconciliations and speeds up close and cash collection. Companies like Cortex, Statsig, and Cursor trust Tabs to scale revenue efficiently. Learn more at https://www.tabs.com/run

Abacum is a modern FP&A platform built by former CFOs to replace slow, consultant-heavy planning tools. With self-service integrations and AI-powered workflows for forecasting, variance analysis, and scenario modeling, Abacum helps finance teams scale without becoming software admins. Trusted by teams at Strava, Replit, and JG Wentworth—learn more at https://www.abacum.ai

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LINKS:

Dan on LinkedIn: https://www.linkedin.com/in/dan-griggs-0970181/

Intercom: https://www.intercom.com/

CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/

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

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RELATED EPISODES:

Inside Rocket Companies: M&A, Metrics, and Mortgage Moats | Brian Brown

https://youtu.be/ttedn4AULt8

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TIMESTAMPS:

00:00:00 Cold Open

00:01:03 Intro to Dan Griggs and Intercom’s AI Pivot

00:02:45 From Ice Cream to SaaS: Early Finance Lessons

00:04:19 Learning the Business by Living the Operations

00:06:26 Why Operational Reality Shapes Better Forecasts

00:08:00 “It’s Not Zero”: Forecasting the Unknowable

00:10:09 Scenario Planning, Ambiguity, and Psychological Safety

00:11:23 Sponsors — Brex | Metronome | RightRev

00:14:43 Keeping a Mental Model of Key Business Metrics

00:16:15 Using Mental Math to Sanity-Check Forecasts

00:17:28 Core Ratios Every CFO Uses to Vet Decisions

00:19:13 The Burn-the-Boats Moment for Intercom’s AI Pivot

00:20:53 Why AI Was an Existential, Not Incremental, Bet

00:22:21 Which SaaS Categories AI Can Fully Replace Work

00:23:04 Why Finance Hasn’t Had Its AI Moment Yet

00:23:39 Sponsors — Rillet | Tabs | Abacum

00:27:05 Why Fin Needed Outcome-Based Pricing

00:28:59 The Tradeoff Behind $0.99 Per Resolution

00:30:46 Why Support Conversations Vary in Complexity

00:32:01 What Drives the Unit Economics of AI Resolutions

00:33:08 How Intercom Chooses Models as Costs Fall

00:35:19 Replacing Generic LLMs With Domain-Specific Models

00:36:08 Selling an AI Product That Could Cannibalize the Core

00:38:50 Founder CEOs Versus Professional CEOs

00:41:47 Hiring Mistakes and Acting on Instincts

00:44:28 Intercom’s Finance Software Stack

00:45:49 The Craziest Expense Request

#RunTheNumbersPodcast #Intercom #AICustomerSupport #OutcomeBasedPricing #CFOInsights

How finance shows its value beyond being the “no” department | Maria Izurieta

CJ Gustafson — Mon, 26 Jan 2026 10:03:09 GMT

In this episode of Run the Numbers, CJ sits down with Maria Izurieta, CFO of Huntress, to unpack what it really means to lead finance as a connective tissue across the organization. Drawing on experience across VC-backed, PE-owned, and public companies, Maria shares how she balances impact versus perfection, builds trust through small wins, and helps teams move from transactional finance to insight-driven decision making. They dig into data transparency, centralized BI, partnering with sales and marketing on revenue, and why the best CFOs unblock friction instead of becoming the “no” department — all while bringing a deeply people-first lens to scale.

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SPONSORS:

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LINKS:

Maria on LinkedIn: https://www.linkedin.com/in/maria-izurieta-909a3b/

Company: https://www.huntress.com/

CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/

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

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RELATED EPISODES:

How the Best CFOs Lead Without Being the CEO | Ken Stillwell

https://youtu.be/O4cx9NBqQso

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TIMESTAMPS:

00:00:00 Preview and Intro

00:01:01 Maria’s Background

00:03:09 People-First Team Building

00:05:16 People, Process, Systems at Scale

00:07:13 Removing Friction Outside Finance

00:09:15 Data Transparency & Decision-Making

00:11:06 Sponsors — Abacum | Brex | Metronome

00:14:22 Forward-Deployed Data

00:16:21 Centralized Data vs. Silos

00:19:23 Finance as Data Steward

00:21:08 Cost-to-Price Feedback Loop

00:22:35 Curiosity Builds Credibility

00:23:43 Sponsors — RightRev | Rillet | Tabs

00:27:12 Trust First, Then Impact

00:30:27 Celebrating Small Wins

00:31:21 From Transactions to Insights

00:33:00 CFO at the Revenue Table

00:34:32 Educating the Org on Metrics

00:36:21 Customer-Level Margin Reality

00:37:13 Using Facts to Change Decisions

00:38:27 Ownership Mindset in Growth Companies

00:39:10 VC vs. PE vs. Public CFO Tradeoffs

00:41:02 Operating Inside Constraints

00:42:18 Finding Your Stage Fit

00:44:17 Building a Personal Advisor Network

00:46:43 Visibility and Women in Leadership

00:47:44 Work–Life Integration, Not Balance

00:48:45 Lightning Round: Biggest Mistake

00:50:10 Advice to Younger Self

00:51:36 Finance Tech Stack

00:52:01 Craziest Expense Story

00:52:44 Credits

#RunTheNumbersPodcast #CFOLeadership #ScalingCompanies #DataDrivenDecisions #ExecutiveLeadership

How the Best CFOs Lead Without Being the CEO | Ken Stillwell

CJ Gustafson — Thu, 22 Jan 2026 10:02:55 GMT

In this episode of Run the Numbers, CJ sits down with Ken Stillwell, CFO and COO of Pegasystems, to explore the realities of leading from the second seat. Ken shares hard-earned lessons from guiding Pega through the shift from term licenses to ARR and ACV, including how to rework sales compensation without losing trust or momentum. They discuss the limits of KPI obsession, the importance of directional clarity over false precision, and why private equity often drives sharper execution than public markets—and how to apply that discipline while still playing the long game.

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SPONSORS:

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LINKS:

Ken on LinkedIn: https://www.linkedin.com/in/ken-stillwell-83a499a/

Pegasystems: https://www.pega.com/

CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/

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

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RELATED EPISODES:

How Finance Becomes a GTM Partner, Not a Bottleneck | Chris Brubaker

https://youtu.be/T2YjdoiJtFA

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TIMESTAMPS:

00:00:00 Preview and Intro

00:02:57 Sponsors — Tabs | Abacum | Brex

00:07:26 The Strategic Value of Being Number Two

00:08:46 Earnings Calls, Messaging, and Real-Time Judgment

00:10:41 Using Feedback to Sharpen Executive Communication

00:11:38 CFOs as Storytellers & Message Repetition

00:12:31 Managing Up: Reading the Room

00:13:59 Learning the Hard Way: Misreading Dynamics

00:15:18 Confidence, Aggression, and Early CFO Mistakes

00:15:58 Sponsors — Metronome | RightRev | Rillet

00:19:45 When to Email vs Pick Up the Phone

00:22:48 Tailoring Communication to Different Functions

00:23:23 Audience-Specific Messaging: “Why Me?”

00:25:24 Values vs Behaviors in Leadership

00:28:13 Why Big Changes Need Anchoring

00:31:14 Moving Pega to the Cloud

00:32:43 Rewiring Sales Comp for ARR & ACV

00:34:56 Sales Credibility Breakdowns with Customers

00:36:20 Economics vs Trust in Sales Teams

00:37:48 Balancing Field Feedback with Company Goals

00:39:17 De-Emphasizing New Logos to Fix the Sales Model

00:41:12 The Danger of Over-Obsessing on KPIs

00:42:51 Public vs Private: Incentives and Operating Discipline

00:45:57 Why Companies Go Private: Motivation Over Patience

00:47:29 The Shrinking Public Markets

00:47:57 Private vs Public CFO Mindsets

00:49:39 Meeting Investors Where They Are

00:50:16 A Risky Decision That Paid Off: Going All-In on the Cloud

00:51:29 Long-Ass Lightning Round

00:53:24 Ken’s Finance Tech Stack & Craziest Expense

00:54:39 Credits

#RunTheNumbersPodcast #CFOLeadership #ExecutiveCommunication #SalesStrategy #PublicVsPrivate

How Finance Becomes a GTM Partner, Not a Bottleneck | Chris Brubaker

CJ Gustafson — Mon, 19 Jan 2026 10:02:28 GMT

In this episode of Run the Numbers, CJ sits down with Chris Brubaker, SVP of Finance at Postscript, who’s helped build the finance function from the ground up. Chris shares how he partners with sales through deal desks, sets pricing guardrails, and makes sure finance helps close deals instead of slowing them down. They dig into his hands-on approach to automation using AI with limited engineering resources, how Postscript’s metrics evolved as the company scaled, when to trust internal data over benchmarks, and where teams get tripped up. Plus, a private jet accounting story—because of course.

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SPONSORS:

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LINKS:

Chris on LinkedIn: https://www.linkedin.com/in/wchrisbrubaker/

Postscript: https://postscript.io/

CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/

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

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RELATED EPISODES:

So You’re Looking for a “Strategic” CFO? Bloomerang’s Steve Isom on What That Really Means

https://youtu.be/cgHOtvG1Ces

The IPO Playbook: Expert Advice from Lee Kirkpatrick, Twilio’s Former CFO

https://youtu.be/PTKAUD7PSWU

The CFO Case for Probabilistic Forecasting With AI | Bruno Annicq

https://youtu.be/Dl8nDZPJMpE

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TIMESTAMPS:

00:00:00 Preview and Intro

00:02:22 Sponsors — Rillet | Tabs | Abacum

00:06:55 Interview Begins

00:07:36 First Finance Hire and Early Scale at Postscript

00:09:02 Usage-Based Margins, COGS, and the Twilio Parallel

00:10:31 Partnering With Sales and Building Deal Desk

00:13:16 Pricing Guardrails, Payback, and Deal Economics

00:15:35 How Deal Desk Evolves Over Time

00:16:01 Sponsors — Brex | Metronome | RightRev

00:19:44 Making Finance a Deal-Closing Partner

00:20:44 Automating Deal Desk With a Slack Bot

00:23:48 How Technical Finance Leaders Need to Be

00:25:17 Automating Without Engineering Help

00:27:12 Why Human Touch Still Matters in SaaS

00:27:53 Postscript’s Finance Tech Stack

00:28:30 ERP Migration and Month-End Efficiency

00:29:42 The Reality of Continuous Close

00:30:34 First Real AI Wins in Accounting

00:31:18 Experimenting With AI Forecasting

00:33:32 Metrics That Matter: Usage as a Leading Indicator

00:35:49 How Metrics Evolve as the Company Scales

00:37:41 Understanding the Product in a Usage-Based Model

00:39:27 Micro-Seasonality and Forecasting Volatility

00:42:21 How to Use Benchmarks Without Misusing Them

00:43:50 Long-Ass Lightning Round: A Costly Modeling Mistake

00:45:45 Advice to a Younger Finance Leader

00:47:05 The Private Jet Accounting Story

00:49:11 Credits

#RunTheNumbersPodcast #FinanceLeadership #DealDesk #UsageBasedSaaS #AIinFinance

The CFO Case for Probabilistic Forecasting With AI | Bruno Annicq

CJ Gustafson — Thu, 15 Jan 2026 10:02:47 GMT

In this episode of Run the Numbers, CJ sits down with Bruno Annicq, CFO of Wellhub (formerly Gympass), to unpack a practical finance playbook built around cash discipline, sustainable growth, and simplicity. Bruno explains how he rebuilt forecasting using an AI-driven, probabilistic ensemble model, moving teams beyond single-scenario planning. They also dig into his EMPOWER planning framework, usable OKRs, and why tighter alignment between finance, HR, and wellbeing is becoming a durable lever for long-term performance.

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SPONSORS:

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LINKS:

Bruno on LinkedIn: https://www.linkedin.com/in/bannicq/

Wellhub: https://wellhub.com/

CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/

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

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RELATED EPISODES:

“Run Toward a Tough Market” — Developing the Hard and Soft Skills To Be a Great Finance Leader

https://youtu.be/iNHbkcG7YEo

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TIMESTAMPS:

00:00:00 Preview and Intro

00:02:19 Sponsors — RightRev, Rillet, Tabs

00:06:43 Accidental CFO Origin Story

00:07:34 Consulting to Operations Pivot

00:08:12 Why Finance Clicked for Bruno

00:09:28 McKinsey Prioritization in Real World

00:10:02 Eisenhower Matrix and Prioritization

00:11:08 Investing in Non-Urgent Work

00:13:30 Lessons From AOL Reinvention

00:16:10 Sponsors — Abacum, Brex, Metronome

00:20:01 Career Growth Through Hard Problems

00:20:52 Broadening Skills Through Change

00:23:12 Five Core Finance Principles

00:24:02 Cash Is King

00:25:14 Driving Sustainable Growth

00:26:01 No Surprises and Forecasting

00:26:07 Finance as Business Enabler

00:27:22 Less Is More Philosophy

00:28:47 Hardest Principle: Less Is More

00:29:46 Deterministic vs Probabilistic Forecasting

00:31:11 Marketplace Volatility and Forecast Error

00:32:10 Ensemble Models Explained

00:33:37 Forecast Accuracy Gains

00:34:53 Building Models In-House

00:36:46 Why Explainability Matters

00:37:48 Empower Framework Introduction

00:47:47 Urgency, Compounding, Long-Term Thinking

00:48:10 Advice to Younger Self

00:50:06 Finance Stack and Expense Stories

00:52:51 Credits

#RunTheNumbersPodcast #CFO #FinanceLeadership #Forecasting #AIinFinance

Automation Outside the Tech Bubble | Jason Kong

CJ Gustafson — Mon, 12 Jan 2026 10:02:59 GMT

In this episode of Run the Numbers, CJ sits down with Jason Kong, General Partner at Base10 Ventures, to unpack the firm’s focus on “automation for the real economy” — software built for industries most tech investors overlook, but the world depends on. Jason breaks down what makes Series B investing uniquely hard, how he evaluates back-office and vertical SaaS opportunities, and where markets tip from niche to overcrowded. They also discuss Base10’s decision to donate 50% of profits to fund scholarships, plus a lightning round spanning fantasy football, shorting SaaS in 2022, and a venture take that might spark debate.

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SPONSORS:

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LINKS:

Jason on LinkedIn: https://www.linkedin.com/in/jasonykong/

Base10 Partners: https://base10.vc/

CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/

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

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RELATED EPISODES:

Scaling to $1B+ Revenue: From ServiceNow to Samsara | Dominic Phillips

https://youtu.be/vBY6WZBMljw

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TIMESTAMPS:

00:00:00 Preview and Intro

00:02:20 Sponsors — Metronome, RightRev, Rillet

00:06:02 Base10 Background

00:06:41 Automation for the Real Economy

00:09:27 Vertical vs. Horizontal Software

00:10:38 Cash Flow and Durability

00:11:19 Product-Market Fit and ROI

00:12:56 Growth Limits Selling to Tech

00:13:19 The Size of the Real Economy

00:14:16 Sponsors — Tabs, Abacum, Brex

00:18:50 Base10’s Giving Model

00:20:30 Access, Education, and Tech

00:21:53 Purpose and Founder Alignment

00:22:51 Radical Transparency

00:23:56 Portfolio Focus and Strategy

00:24:05 Investing Ahead of Consensus

00:26:29 ERP Adjacency as Alpha

00:28:58 Lessons From Hedge Funds

00:32:29 Public Markets Reality

00:34:05 Public vs. Private Investing

00:34:48 The Series B Sweet Spot

00:36:49 A Bifurcated Series B Market

00:38:56 Fast Series Bs and 2021 Vibes

00:42:16 What Series B Looks Like Now

00:44:36 Back Office Automation

00:46:02 ERP-Centric Workflows

00:48:33 Long-Ass Lightning Round

00:49:36 Shorting SaaS in 2022

00:50:16 Fantasy Football and Investing

00:52:57 Career Advice That Surprises

00:55:03 A Contrarian Venture Take

00:56:22 Credits

#RunTheNumbersPodcast #SeriesB #RealEconomy #VerticalSaaS #BackOfficeAutomation

Scaling to $1B+ Revenue: From ServiceNow to Samsara | Dominic Phillips

CJ Gustafson — Thu, 08 Jan 2026 10:03:21 GMT

In this episode of Run the Numbers, CJ sits down with Dominic Phillips, CFO of Samsara, to unpack what it takes to scale a capital-intensive SaaS business from startup to public company in under a decade. Dominic reflects on his six-plus years at Samsara through hypergrowth, COVID disruption, supply chain constraints, a down-round survival raise, and an IPO at the very end of the 2021 tech window. Drawing on his earlier career at ServiceNow under Mike Scarpelli, he shares how experience across FP&A, IR, corp dev, and treasury shaped his approach to capital allocation, investor education, and analyst management. The conversation dives into asset-based pricing, selling into non-discretionary operations budgets, balancing hardware and software economics, and building credibility with a broad analyst base while scaling past $1B in ARR.

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SPONSORS:

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LINKS:

Dominic on LinkedIn: https://www.linkedin.com/in/dominicphillips/

Company: https://www.samsara.com/

CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/

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

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RELATED EPISODES:

“Steal Your Boss’s Job”: Calendly CFO John McCauley on Leadership, Ownership & Growth

https://youtu.be/VRpTNDIfzPY

From SMB to Enterprise: The CFO Scaling Playbook With Andrew Casey | Mostly Classics

https://youtu.be/kMuJ6gAuEpg

Driving revenue without selling | Greg Henry of 1Password

https://youtu.be/f5FsNoG8A3E

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TIMESTAMPS:

00:00:00 Preview & Intro

00:02:40 Sponsors — Brex | Metronome | RightRev

00:06:18 Interview Begins

00:06:46 Dominic’s Early Career

00:08:47 From ServiceNow to CFO

00:09:47 Joining Samsara

00:10:54 COVID, Burn, and a Down Round

00:12:40 IPO Messaging and Investor Education

00:15:50 Sponsors — Rillet | Tabs | Abacum

00:20:27 Hardware + Software Story

00:21:29 What Samsara Does

00:22:30 Data, AI, and ROI

00:23:23 Horizontal Platform and Verticals

00:24:27 Growth Drivers at Scale

00:26:09 Selling Into Operations

00:28:19 Change Management in Legacy Orgs

00:29:46 Non-Discretionary Budgets

00:33:02 Storytelling Lessons from Scarpelli

00:36:14 Managing Analysts

00:39:23 Earnings Timing Strategy

00:41:06 Metrics and Investor Trust

00:42:38 Investor Communication Channels

00:44:22 Investor Days and Long-Term Vision

00:45:37 Annual Planning Maturity

00:48:24 Forecast Accuracy and Cadence

00:49:28 The 1000-Day Strategy

00:50:40 Top-Line and Margin Targets

00:51:59 Capital Allocation by Function

00:54:46 Becoming a CFO

00:58:21 Lightning Round and a CFO Mistake

01:02:41 End Credits

#RunTheNumbersPodcast #CFO #ScalingCompanies #B2BSaaS #PublicMarkets

Hackers and Hidden Risks: Business Insurance Breakdown with Gordon Coyle

CJ Gustafson — Mon, 05 Jan 2026 10:03:13 GMT

In this episode of Run the Numbers, CJ Gustafson sits down with Gordon Coyle, a 40-year commercial insurance veteran, to demystify one of the most anxiety-inducing topics for founders and CFOs: business insurance. Drawing on decades of experience with startups, scaleups, and regulated industries, Gordon breaks down what leaders need to know about D&O, E&O, cyber, and general liability, why investor pressure is rising, and where “cheap and easy” online policies fail when real risk hits. Through real-world examples, they explore how claims arise, how defense costs erode limits, why cyber insurance is as much about response as reimbursement, and how to balance budget, risk tolerance, and peer benchmarks—treating insurance as a critical layer of protection, not a box-checking exercise.

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SPONSORS:

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LINKS:

Gordon on LinkedIn: https://www.linkedin.com/in/gordoncoyle/

The Coyle Group: https://thecoylegroup.com/

CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/

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

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RELATED EPISODES:

The Coyle Group - Business Insurance

https://www.youtube.com/@TheCoyleGroupNY

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TIMESTAMPS:

00:00:00 Preview and Intro

00:01:53 Sponsors — Abacum | Brex | Metronome

00:05:39 Interview Begins with Gordon Coyle

00:06:23 Gordon Coyle & The Coyle Group

00:07:21 Explaining Insurance on YouTube

00:08:40 Turning Education into Inbound Leads

00:09:40 Content as a Pull Strategy

00:10:53 Insurance Complexity for Tech Founders

00:13:28 Why Investors Require D&O Insurance

00:14:09 What D&O Covers and Why It Matters

00:15:50 Sponsors — RightRev | Rillet | Tabs

00:20:19 Who D&O Covers and Rising Investor Pressure

00:22:37 D&O Limits and Cost Tradeoffs

00:23:21 Panic Calls and Late D&O Purchases

00:24:39 How Defense Costs Erode Coverage

00:25:31 Common D&O Claims and Employment Risk

00:27:08 D&O vs E&O Explained

00:29:12 Cyber Insurance and Social Engineering

00:31:59 AI’s Impact on Cyber Risk

00:33:50 Real-World Ransomware Stories

00:34:17 Cyber Insurance as Money and Response

00:35:29 Business Email Compromise Scams

00:39:43 Why Tech Still Needs General Liability

00:41:16 What a BOP Covers

00:42:32 Convenience vs Proper Coverage

00:44:29 Surprising General Liability Claims

00:46:45 Insurance Costs for Startups

00:47:36 Higher Costs in High-Risk Industries

00:48:26 Balancing Budget, Risk, and Coverage

00:50:39 PEOs, Workers’ Comp, and EPLI

00:54:39 Choosing the Right Insurance Partner

00:56:42 End Credits

#RunTheNumbersPodcast #StartupFinance #BusinessInsurance #RiskManagement #CyberRisk

a16z’s Alex Immerman on How AI Is Redefining the Modern CFO | Mostly Classics

CJ Gustafson — Thu, 01 Jan 2026 10:02:23 GMT

[Original air date: June 19, 2025]

In this episode, Alex Immerman, partner at Andreessen Horowitz, joins CJ to discuss the CFO role and how it’s changing in the era of AI. He explains what the components of a company’s AI agenda the CFO should own, how and where it should be leveraged in an organization, and why, if you’re preparing to go public, AI needs to be mentioned in your S-1. He breaks down how the financial landscape differs greatly between AI-native SaaS companies and traditional B2B SaaS companies in terms of retention curves and gross margins, and how this relates to the ever-important LTV to CAC metric. As someone who has worked with prominent CFOs and interviewed many for a16z’s portfolio companies, Alex also describes the qualities of a great CFO, and shares his favorite interview question, before discussing CFOs, CEO, and board dynamics.

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LINKS:

Alex Immerman on LinkedIn: https://www.linkedin.com/in/immerman

Andreessen Horowitz: https://a16z.com

CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/

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

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RELATED EPISODES:

a16z’s Alex Immerman on the Evolving Role of the CFO in the Age of AI

https://youtu.be/JIvHp-mlnzs

So You’re Looking for a “Strategic” CFO? Bloomerang’s Steve Isom on What That Really Means

https://www.youtube.com/watch?v=cgHOtvG1Ces

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TIMESTAMPS:

00:00:00 Preview and Intro

00:01:46 AI Margins Improve Dramatically

00:02:29 What Separates Great CFOs

00:03:29 Founder Mindset Drives Performance

00:05:31 Founder Intensity and Margin Expansion

00:06:57 Backing Unproven Bets Thoughtfully

00:08:29 Interviewing CFOs for Backbone

00:09:55 When CFOs Push Back on Strategy

00:11:25 CFO Trust With Boards and Investors

00:11:50 How CFOs Engage Investors When Hiring

00:14:44 Building Strong CFO Investor Relationships

00:16:18 Sharing Bad News Early

00:17:21 CEO Vision Versus CFO Validation

00:20:57 How AI Is Changing the CFO Role

00:23:56 Incumbents Versus AI-Native Finance Tools

00:26:24 CFOs Driving Internal AI Adoption

00:28:07 AI Impact on Customer Support Efficiency

00:29:26 Internal Leverage From AI Automation

00:31:29 Why Investors Care About LTV to CAC

00:34:00 LTV to CAC Across Business Models

00:36:26 Retention Curves Matter More Than Growth

00:38:16 Evaluating AI Gross Margins Long Term

00:40:04 Recipe for AI Margin Expansion

00:43:01 What Makes a Public-Ready CFO

00:44:47 Beating Guidance Drives IPO Performance

00:46:56 Growth Versus Profitability Has Rebalanced

#RunTheNumbersPodcast #CFOLeadership #FintechInvesting #AISaaS #VentureCapital

The Strategic Power of Investor Relations | Mostly Classics

CJ Gustafson — Mon, 29 Dec 2025 10:02:27 GMT

[Original air date: May 8, 2025]

When it comes to investor relations, an organization’s communication strategy should be a key instrument to support its business strategy. While this may seem obvious, so often we get this wrong. In this episode, CJ hosts a masterclass on investor relations with Samuel Levenson of the Arbor Advisory Group and Jon Neitzell of Andruil Partners, focusing on the strategic role of IR in driving company valuation. They cover what “audience opportunity” really means and what to do when you’ve attracted the wrong investors. They talk about metrics, KPIs, and OKRs, plus why management credibility and conveying conviction can make or break your IR strategy. They also discuss what has changed in the IR profession over time and what hasn’t (but probably should) before suggesting changes you can make to drive impact immediately.

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LINKS:

Samuel Levenson on LinkedIn: www.linkedin.com/in/samlevenson/

Jon Neitzell on LinkedIn: www.linkedin.com/in/jonathan-neitzell/

Arbor Advisory Group: www.arboradvisorygroup.com/

Anduril Partners: https://www.andurilpartners.ai/

CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/

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

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RELATED EPISODES:

Investor Relations as a Strategic Weapon: A Masterclass

https://youtu.be/ac9xmURhAqE

—

TIMESTAMPS:

00:00:00 Preview and Intro

00:02:22 Welcome to Sam and Jon

00:03:12 Linking Business Strategy and Communication

00:05:01 Proactive vs. Reactive Investor Relations

00:06:39 Tailoring the Message by Investor Type

00:08:05 Audience Opportunity and Ideal Shareholders

00:11:05 When the Investor Base No Longer Fits

00:12:21 Shifting Investors as Industries Change

00:13:16 Optionality Comes From Patient Shareholders

00:14:40 Conveying Conviction Through Credibility

00:17:03 Why Investor Days Build Trust

00:18:02 Metrics Versus Storytelling in IR

00:19:10 Choosing Metrics the Market Actually Rewards

00:22:30 Valuation Disconnects and Investor Confusion

00:23:17 Finding Metrics That Truly Drive Value

00:25:33 Avoiding Bad Capital Allocation Decisions

00:26:20 Disclose Versus Guide: Confidence Intervals

00:27:35 Knowing What You Don’t Know

00:29:33 Science Versus Art in Storytelling

00:33:11 When Algorithms Become Your Audience

00:33:56 Passive Investing Now Dominates Markets

00:35:16 Linking OKRs to Value-Driving KPIs

00:36:42 Closing the Strategy-Metrics Feedback Loop

00:38:07 When Investors Sense Operational Confidence

00:39:47 Why IR Becomes Strategy Consulting

00:41:28 Why IR Teams Stay Undersized

00:43:23 Sam’s Accidental Entry Into Investor Relations

00:44:34 Mentorship Over Formal IR Training

00:46:18 How Markets Outpaced IR Practices

00:47:01 Investor Days Go Virtual

00:49:34 Designing a High-Quality Earnings Call

00:50:41 Investor Days as High-ROI Investments

00:51:45 IR Websites as Investor Onramps

00:53:42 World-Class Investor Day Examples

00:54:20 Using AI to Prepare Investor Communications

00:56:19 Building a Proactive IR 2.0 Strategy

00:58:33 Why IR Requires Full Executive Buy-In

01:00:51 Data Transfers Conviction to Investors

01:03:31 Closing Reflections on Trust and Valuation

#RunTheNumbersPodcast #InvestorRelations #CapitalMarkets #ValuationStrategy #CFOInsights

Inside the Economics of Independent Creators | Mostly Growth

CJ Gustafson — Sat, 27 Dec 2025 10:02:22 GMT

Mostly Growth on YouTube: https://www.youtube.com/@MostlyGrowth

Mostly Growth on Apple: https://podcasts.apple.com/us/podcast/mostly-growth/id1842238102

Mostly Growth on Spotify: https://open.spotify.com/show/3KDtaLaXx1obFp5PUhZ6V3

In this year-end episode of Mostly Growth, CJ Gustafson, Kyle Poyar, and Ben Hillman reflect on what it actually takes to build a modern media business around newsletters and podcasts. They unpack CJ’s first year going full-time, comparing creative intuition versus metric-driven operating styles, and discuss what content truly drives growth. The conversation also covers distribution dynamics, the emotional reality of unsubscribes and burnout, and closes with a candid look at monetization, team building, and the tradeoffs between simplicity and scale.

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SPONSORS:

Pulley is the cap table management platform built for CFOs and finance leaders who need reliable, audit-ready data and intuitive workflows, without the hidden fees or unreliable support. Switch in as little as 5 days and get 25% off your first year: https://pulley.com/mostlymetrics

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LINKS:

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

CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/

Growth Unhinged: https://www.growthunhinged.com/

Kyle on LinkedIn: https://www.linkedin.com/in/kyle-poyar/

Slacker Stuff: https://www.slackerstuff.com/

Ben on LinkedIn: https://www.linkedin.com/in/slackerstuff/

https://www.growthunhinged.com/p/deep-research-for-gtm

https://www.growthunhinged.com/p/2025-state-of-b2b-gtm-report

https://www.mostlymetrics.com/p/presenting-the-state-of-the-agentic-financial-stack

https://www.mostlymetrics.com/p/the-great-ai-arr-illusion

https://www.mostlymetrics.com/p/presenting-the-2025-tech-stack-report

https://www.mostlymetrics.com/p/download-the-annual-planning-bible

https://www.growthunhinged.com/p/how-to-sell-annual-plans

https://www.growthunhinged.com/p/get-recommended-by-chatgpt

https://www.growthunhinged.com/p/gtm-vibecoding-ideas

https://www.growthunhinged.com/p/how-to-use-ai-agents-for-marketing

—

RELATED EPISODES:

We get roasted for swag and drop some GTM gold

https://youtu.be/uubf_8al95w

Do vanity plates bring serious business?

https://youtu.be/Cm1rubFb-kg

Pricing in the Real World: Babies, Bots, and Billing

https://youtu.be/T1cjFSZR0k0

—

TIMESTAMPS:

00:00:00 Preview and Intro

00:01:52 Sponsors — Pulley | Metronome

00:04:12 Action Figure Swag and Year-in-Review Setup

00:05:47 Going Full-Time and the First-Year Reality Check

00:07:24 Writing Schedules, Creative Work, and Time Optimization

00:09:16 Writing Speed, Craft, and the Myth That Time Equals Quality

00:10:51 Perfectionism vs. Throughput in Newsletter Writing

00:13:03 Creator Burnout, Motivation, and Engagement Anxiety

00:14:08 Playing the Long Game vs. Obsessing Over Metrics

00:15:42 Best Work of the Year and High-Leverage Content Bets

00:17:55 Big Research Reports as Career-Defining Projects

00:19:19 When Memes Outperform Deep Work

00:19:52 LinkedIn Algorithms vs. Content Quality

00:20:51 Writing for the Feed vs. Writing to Think

00:22:03 Optimizing LinkedIn Profiles for Credibility

00:23:47 Subscriber Growth, Audience Quality, and Churn Reality

00:27:20 Reports and Research as Growth Engines

00:28:37 Tactical “How-To” Content That Actually Converts

00:30:21 Tactical Value Beats Sounding Smart

00:30:40 Building a Team and Scaling Beyond a Solopreneur

00:32:05 Simplicity vs. Scale in Early Business Decisions

00:35:37 Avoiding Boredom and Shiny Object Syndrome

00:37:12 Balancing Writing, Consulting, and Energy

00:37:54 Making the Leap Financially as a Creator

00:39:01 Subscriptions vs. Advertising as the Real Business Model

#MostlyGrowthPodcast #CreatorEconomy #IndependentCreator #NewsletterBusiness #YearInReview

Capital Spoilage and Leakage: A CFO’s Guide to Finding What’s Lost | Mostly Classics

CJ Gustafson — Thu, 25 Dec 2025 10:02:24 GMT

[Original air date: June 5, 2025]

How can finance leaders identify where their capital is silently going to waste and where it can be better used to drive growth? In this episode, CJ interviews Russell Lester, the CFO of Tropic, where capital allocation is both the product and the mission. Russell introduces the concept of “spoilage”, deployed capital that fails to deliver its intended value. He also talks about “levers”, positive actions that force multiply your efforts, and “leakages”, headwinds or detractors that sap momentum. Russell believes it is the job of the CFO (or “Chief Alignment Officer”) to proactively go looking for these levers and leakages. He then explains how he uses his “center of the table” framework to redeploy the freed-up capital to fuel growth. Russell also covers how to address misalignment, what helicopter skills are and why you need them, what a data safari is and why you should take one daily, and why every CFO needs a spend management tool.

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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

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.

Sage Intacct is a cloud financial management platform that replaces spreadsheets, automates workflows, and keeps your books audit-ready as you scale. It unifies accounting, ERP, and real-time reporting for finance, retail, logistics, tech, and professional services. With payback in under six months and up to 250% ROI, and eight years as the customer-satisfaction leader, Sage Intacct helps you take control of your growth: https://bit.ly/3Kn4YHt

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.

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LINKS:

Russell on LinkedIn: https://www.linkedin.com/in/russell-lester-aa98463/

Tropic: https://www.tropicapp.io/

CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/

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

—

RELATED EPISODES:

Wasted Capital and Where to Find It The CFOs Guide to Spoilage Levers Leakages

https://youtu.be/xOby7CcdljI

—

TIMESTAMPS:

00:00:00 Mostly Classics: Russell Lester on Capital and Alignment

00:00:48 Sponsors — Tipalti | Aleph | Fidelity Private Shares

00:04:07 Russell Lester Joins the Show

00:06:45 Capital Spoilage and Wasted Spend

00:08:34 Why Spoilage Goes Unnoticed Inside Companies

00:10:16 Creating Accountability for ROI

00:11:08 Spoilage Beyond Tools and Software

00:13:04 Strategy Drift and the Sunk Cost Trap

00:14:14 Sponsors — Sage Intacct | Mercury | RightRev

00:17:44 Levers and Leakages: A Framework for Momentum

00:19:27 Identifying Levers Across the Funnel

00:21:48 Efficiency Levers Inside the P&L

00:23:31 Common Spend Leakages in Practice

00:24:21 The Center of the Table Framework

00:26:47 Budget Ownership vs Corporate Stewardship

00:28:49 The CFO as Chief Alignment Officer

00:31:31 Trust, Tact, and Executive Leadership

00:33:35 Helicopter Skills for Finance Leaders

00:35:41 Curiosity as a CFO Superpower

00:36:02 Data Safaris and Asking Better Questions

00:38:16 Breaking Down Net Dollar Retention

00:40:32 Navigating Data Overload

00:42:16 Building a Single Source of Truth

00:43:03 Intelligent Spend Management in Action

00:44:44 Capital Allocation as the CFO’s Core Job

00:46:04 How Spend Management Drives Growth

00:49:14 Why Companies Delay Spend Tools

00:50:49 A Career Mistake with Investors

00:52:49 Auto-Renewals: Revenue vs Leakage

00:54:07 Advice to a Younger CFO

#RunTheNumbersPodcast #CFOLeadership #CapitalAllocation #FinancialStrategy #SpendManagement

From CFO to Founder: Inside the Making of Mostly Media | Paul Stansik Interviews CJ

CJ Gustafson — Mon, 22 Dec 2025 10:02:44 GMT

In this special, table-turning episode of Run the Numbers, CJ Gustafson steps out of the host’s chair as Paul Stansik—Operating Partner at ParkerGale and author of the Hello Operator newsletter—takes over the interview. What began as a planned discussion on annual planning best practices quickly evolves into a candid deep dive on Mostly Media, CJ’s growing niche B2B media business, and the thinking behind his own operating plan for the year ahead. Fresh off exiting his CFO role in January 2025, CJ walks through the origin story of Mostly Metrics, how it scaled into a broader media platform, and what it’s like being “the boss of me” for the first time. Paul presses on the real questions—growth opportunities, monetization, and strategic tradeoffs—making this episode a transparent look at how a modern, metrics-driven media business is built and run.

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SPONSORS:

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LINKS:

Paul on LinkedIn: https://www.linkedin.com/in/paulstansik/

Hello Operator: https://hellooperator.substack.com/

CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/

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

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RELATED EPISODES:

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

https://youtu.be/pOj4JwGUTSo

Grindr’s $0 CAC Secret from the CFO Who Launched Disney+ | Vanna Krantz

https://youtu.be/ijFIMmtpLNw

Scaling to $1B+ Revenue: From ServiceNow to Samsara | Dominic Phillips

https://youtu.be/vBY6WZBMljw

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TIMESTAMPS:

00:00:00 Preview and Intro

00:02:10 Sponsors — RightRev | Tipalti | Aleph

00:06:23 Episode Setup and Context

00:07:22 Why This Episode Exists

00:08:44 The Origin Story

00:10:03 First Signs of Traction

00:10:26 Memes, Early Growth, and “Big Ballers”

00:12:01 Defining the Brand Feel

00:13:28 Leaving a Job to Write

00:15:07 Writing His Way to CFO

00:16:26 Sponsors — Fidelity Private Shares | Sage Intacct | Mercury

00:19:01 Growth Tactics That Worked

00:21:31 First Monetization Moment

00:22:13 Balancing CFO Life and Media

00:24:06 Going All-In on the Business

00:25:02 A CFO Lens on Media

00:28:09 Asset Businesses vs Cash Flow

00:31:35 How the Business Makes Money

00:32:42 Revenue Compounding Over Time

00:33:29 Scaling to $3M

00:34:08 Partnerships and Buying Cycles

00:36:19 Building the Core Team

00:39:09 Adding Recruiting to the Mix

00:41:01 Strategy for the Next Phase

00:42:03 Boredom, Discipline, and Craft

00:43:08 Defining the Core Audience

00:46:09 Staying in the Game

00:47:22 Advice for Creators

00:49:15 Brand, Fun, and Value

00:52:08 Following the Momentum

00:53:14 Finding Your Unique Edge

00:55:19 Enjoying the Build

00:56:25 Closing and Outro

#RunTheNumbersPodcast #creatoreconomy #mediabusiness #cfoperspective #buildinpublic

AirPods as Recurring Revenue, Direct Mail’s Revival, and Other Growth Predictions | Mostly Growth

CJ Gustafson — Sat, 20 Dec 2025 10:02:21 GMT

Mostly Growth on YouTube: https://www.youtube.com/@MostlyGrowth

Mostly Growth on Apple: https://podcasts.apple.com/us/podcast/mostly-growth/id1842238102

Mostly Growth on Spotify: https://open.spotify.com/show/3KDtaLaXx1obFp5PUhZ6V3

In this episode of Mostly Growth, CJ Gustafson, Kyle Poyar, and Ben Hillman unpack a wide-ranging set of predictions and observations about where go-to-market strategy, AI, and pricing models are headed next. They discuss why what ChatGPT says about your product may become a core marketing KPI, the resurgence of direct mail and physical touchpoints in an AI-saturated world, and why “almost as good as a human” is a dangerous positioning for AI-driven products. The conversation also explores AI monetization paths through advertising, the risk of an AI infrastructure timing mismatch leading to a broader financial pullback, and what historical parallels like railroads and the Sears catalog can teach us about today’s buildout. The episode closes with real-world pricing lessons, from energy-as-a-service solar subscriptions to the surprisingly massive standalone economics of Apple’s AirPods, tying together how distribution, perception, and monetization shape durable growth.

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SPONSORS:

—

LINKS:

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

CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/

Growth Unhinged: https://www.growthunhinged.com/

Kyle on LinkedIn: https://www.linkedin.com/in/kyle-poyar/

Slacker Stuff: https://www.slackerstuff.com/

Ben on LinkedIn: https://www.linkedin.com/in/slackerstuff/

—

RELATED EPISODES:

996 Culture, Exploding AI Bills & SaaS Chaos

https://youtu.be/qhrxDL0gsRo

The Layer-Cake Playbook for Vertical SaaS Growth | with Roland Ligtenberg

https://youtu.be/yPxWvhPISKo

OpenAI’s Impossible Math: $500B or Bust?

https://youtu.be/L6PLnvjcnpk

From Birding Apps to Billion-Dollar Bundles: The Future of SaaS Growth

https://youtu.be/mzITrIP70Ok

Where Did All the Middle Managers Go?

https://youtu.be/LvN7RzmApPU

—

TIMESTAMPS:

00:00:00 Preview and Intro

00:01:40 Sponsors — Pulley, Metronome

00:04:00 Welcome Back And Consumer Friction

00:05:29 Insurance Middlemen Frustrations

00:07:07 Explaining Newsletter Businesses

00:07:58 Family Perceptions Of Work

00:09:05 GTM And Growth Predictions

00:10:19 Trust And Objectivity In ChatGPT

00:12:01 ChatGPT As Marketing KPI

00:14:14 Direct Mail Marketing Comeback

00:15:56 Tech Buying Media Assets

00:17:52 Fake Subscribers And Email Lore

00:19:03 AI Quality Over Automation

00:22:11 AI Healthcare And Ad Models

00:24:40 Advertising Fuels AI Economics

00:25:40 AI Boom Versus Bust Timing

00:27:49 Infrastructure Before Killer Apps

00:30:21 Railroad Economics And Real Estate

00:30:46 Solar Subscriptions And Pricing

00:32:50 AirPods As Recurring Revenue

00:34:57 Show Outro And Credits

#MostlyGrowthPodcast #GrowthMarketing #AITrends #GoToMarket #StartupStrategy

Running the Long Game in Growth Equity | Larry Contrella

CJ Gustafson — Thu, 18 Dec 2025 10:02:16 GMT

In this episode of Run the Numbers, CJ Gustafson sits down with Larry Contrella, General Partner at JMI Equity, to unpack how JMI invests in software without financial engineering or roll-up strategies. Larry explains how the firm builds conviction through founder relationships, long-term partnership, and a product-and-brand-first view of durable growth. They discuss how JMI supports companies through scaling, why operating partners keep returning, and how underwriting looks different in mission-driven sectors like K–12 and nonprofit tech where customers are schools and communities, not Fortune 500s. Larry’s background as a competitive runner at Penn ties the conversation together with a clear ethos: patience, discipline, and playing the long game.

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SPONSORS:

—

LINKS:

Larry on LinkedIn: https://www.linkedin.com/in/larry-contrella-160a8a25/

JMI Equity: https://www.jmi.com/

CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/

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

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RELATED EPISODES:

Is taking a company public even worth it? | Fullstory’s Chad Gold

https://youtu.be/zSD8y9dr4Vg

So You’re Looking for a “Strategic” CFO? Bloomerang’s Steve Isom on What That Really Means

https://youtu.be/cgHOtvG1Ces

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TIMESTAMPS:

00:00:00 Preview and Intro

00:02:49 Sponsors — Mercury | RightRev | Tipalti

00:06:41 Joining the JMI Conversation

00:07:13 College Running and Team Dynamics

00:08:13 New York Marathon Story and Career Intersection

00:11:04 Competitive Drive and Patience With Founders

00:12:54 Building Long-Term Partnerships and Underwriting Credibility

00:15:27 Growth Equity as a Long Sales Cycle

00:15:48 Sponsors — Aleph | Fidelity Private Shares | Sage Intacct

00:18:44 Fund Planning, Deal Pacing, and Board Commitments

00:20:59 Sourcing Philosophy and Developing Investors Over Time

00:22:09 Hustle as the Only Sustainable Edge in Sourcing

00:24:14 Early Sourcing Tactics and Information Arbitrage

00:26:06 Reputation, Experience, and Breaking Into Competitive Deals

00:29:42 Organic Growth Over Roll-Ups and M&A Discipline

00:32:51 Brand, Product Leadership, and Paying for the Best Businesses

00:33:29 Bloomerang and Brand-Led Growth in Nonprofit Software

00:34:46 Why JMI Operators Keep Coming Back

00:36:28 Collaborative Leadership and Giving Constructive Advice

00:38:20 Using Data Without Slowing Decisions

00:39:20 Transparency, Alignment, and Knowing Where You Stand

00:40:31 Why JMI Invests in K–12 and EdTech

00:42:07 Mission-Driven Businesses and Talent Advantage

00:43:24 Monetization Models in Nonprofit SaaS

00:45:40 Conviction Bets and Product-Market Fit Stories

00:48:49 Rethinking TAM and Expanding Markets Over Time

00:50:40 Lightning Round: Sourcing Stories and Lessons

00:52:58 Traits of Great Founders and Changing Beliefs

00:54:20 Closing Thoughts and Outro

#RunTheNumbersPodcast #GrowthEquity #B2BSoftware #FounderRelationships #PrivateEquity

Inside Rocket Companies: M&A, Metrics, and Mortgage Moats | Brian Brown

CJ Gustafson — Mon, 15 Dec 2025 10:02:48 GMT

In this episode of Run the Numbers, CJ Gustafson sits down with Brian Brown, Chief Financial Officer and Treasurer at Rocket Companies, to unpack how Rocket has built a differentiated, full-stack fintech business far beyond its mortgage roots. The conversation explores Rocket’s approach to long-tail monetization, the strategic importance of mortgage servicing, and how recapture rates become a durable competitive advantage in volatile rate environments. Brian shares lessons from leading complex M&A transactions, managing a business that reacts in real time to macro signals, and building a finance organization that prioritizes storytelling, strategy, and cross-functional thinking over pure accounting prowess. The result is a wide-ranging discussion on what traditional financial services companies can teach modern SaaS and fintech leaders about metrics, brand, and disciplined execution.

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SPONSORS:

—

LINKS:

Brian on LinkedIn: https://www.linkedin.com/in/brian-brown-3aa37a8a/

Rocket Companies: https://rocket.com/

CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/

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

—

RELATED EPISODES:

From $500M Losses to $500M Profits: The CFO Who Helped Major League Baseball Win off the Field

https://youtu.be/7xw9qY2w5C4

—

TIMESTAMPS:

00:00:00 Preview and Intro

00:02:30 Sponsors — Sage Intacct | Mercury | RightRev

00:05:55 CJ’s Rocket Mortgage Fanboy Moment

00:07:13 How Rocket Mortgage Actually Makes Money

00:12:06 Investing in Brand Trust for Infrequent but High-Stakes Decisions

00:15:17 Mortgage Servicing as a Long-Term Relationship Engine

00:17:17 Sponsors — Tipalti | Aleph | Fidelity Private Shares

00:20:40 Why the Long Tail of Customer Relationships Is Underrated

00:23:01 Recapture Rate and Why Mortgage Loyalty Is Broken

00:25:23 Lower CAC Through Lifetime Value and Repeat Borrowers

00:30:55 Financial Storytelling as a CFO’s Real Job

00:33:03 Why CFOs Must Sell the Story, Not Just the Numbers

00:40:49 Public vs. Private M&A and Why Public Deals Are Harder

00:45:21 Redfin Acquisition Thesis and Top-of-Funnel Strategy

00:52:18 Being Swarmed by Merger Arb Funds Like Taylor Swift

00:55:18 How Rocket Forecasts in a Volatile Interest Rate Environment

00:58:04 Weekly Forecasting, Scenario Planning, and Avoiding Forecast Fatigue

01:00:32 Finance Teams as Business Consultants and Strategic Partners

01:02:23 Why CFOs Need a Seat at the Strategy Table

01:04:19 Long-Ass Lightning Round: A Leadership Mistake and Building Teams

01:05:58 Leadership Lessons on Team Size and Accountability

01:07:33 Advice to Younger Self and Slowing Down

01:08:49 Finance Software Stack and AI Tools

01:11:31 Lessons from Working with Dan Gilbert

01:16:58 Craziest Expense Story

01:17:55 Outro

#RunTheNumbersPodcast #CFOLeadership #FinanceStrategy #MergersAndAcquisitions #FinancialStorytelling

Mall Santas, Chicken Fingers, and Why Focus Wins | Mostly Growth

CJ Gustafson — Sat, 13 Dec 2025 10:02:24 GMT

Mostly Growth on YouTube: https://www.youtube.com/@MostlyGrowth

Mostly Growth on Apple: https://podcasts.apple.com/us/podcast/mostly-growth/id1842238102

Mostly Growth on Spotify: https://open.spotify.com/show/3KDtaLaXx1obFp5PUhZ6V3

In this episode of Mostly Growth, CJ Gustafson and Kyle Poyar explore the hidden mechanics behind focus, competition, and value creation across both consumer culture and B2B SaaS. They unpack why point-solution companies like Untuckit and Raising Cane’s can outperform diversified rivals, examine how competition actually strengthens category demand, and break down the gray zone of mid-market venture exits where founder incentives and investor expectations diverge. The conversation ranges from private equity roll-ups to the realities of cold-calling returning as a top-performing growth channel, to pricing transparency, algorithmic price discrimination, and how everyday behaviors—from mall Santas to $12 club water—reflect deeper strategic forces. It’s a fast, practical look at how operators can stay focused, understand market pressure, and avoid chasing the wrong game.

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SPONSORS:

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LINKS:

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

CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/

Growth Unhinged: https://www.growthunhinged.com/

Kyle on LinkedIn: https://www.linkedin.com/in/kyle-poyar/

Slacker Stuff: https://www.slackerstuff.com/

Ben on LinkedIn: https://www.linkedin.com/in/slackerstuff/

—

RELATED EPISODES:

Building AI-Native Software With No Rules | Christopher O’Donnell

https://youtu.be/Fr1027kZyC0

SaaS Founder or Pop Star? CJ Gets Schooled

https://youtu.be/LMZq_DwVmkY

The Layer-Cake Playbook for Vertical SaaS Growth | with Roland Ligtenberg

https://youtu.be/yPxWvhPISKo

The One Use Case for Venture Debt That Most Founders Never Think About

https://youtu.be/XxH_Y9OH_i0

—

TIMESTAMPS:

00:00:00 Preview and Intro

00:01:42 Sponsors – Pulley | Metronome

00:04:02 Mall Fashion & Nostalgia

00:05:50 The Modern Mall Santa Reinvented

00:06:52 Untuckit & the Platform vs. Point Solution Debate

00:08:31 The Power of Category Focus

00:09:56 Obsession, Craft, and the Raising Cane’s Lesson

00:10:46 Germany’s “Hidden Champions”

00:12:44 Competition: When to Care and When Not To

00:14:05 OpenAI, Gemini & the “Code Red” Mindset

00:15:34 Competition to Category Education

00:17:00 Pricing Pages as Competitive Battlegrounds

00:18:05 VC Deck Theater & Competitive Grids

00:18:54 Rise of B2B Newsletter Advertising

00:19:48 Awkward Exits: The Venture “Gray Zone”

00:21:46 Founder Life-Changing Exits vs. VC Math

00:23:04 Why Secondaries Exist (and When They Help)

00:24:58 Why $100–500M Is the Most Common SaaS Exit Range

00:26:14 Structural Misalignment in Venture Exits

00:27:20 How Much Secondary Is Too Much?

00:30:25 Business Blunders: Justin Bieber the PM

00:31:54 Voice Notes, Etiquette, and Chaos

00:33:23 Cold Calling Makes a Comeback

00:35:50 Catherine Jhung Still Cold Calls CFOs

00:37:44 Algorithm Pricing Labels & Data-Driven Pricing

00:41:11 Why Clubs Charge $12 for Water

00:42:40 Closing Credits

#MostlyGrowthPodcast #keepitsimple #focuswins #businessstrategy #operatorsmindset

From Amazon to Docusign: A CFO’s Guide to Building Durable Systems | Blake Grayson

CJ Gustafson — Thu, 11 Dec 2025 10:02:55 GMT

Blake Grayson, CFO of Docusign, joins CJ Gustafson to discuss how a company that redefined e-signature and became a verb is now navigating its next chapter in intelligent agreement management. Drawing on more than a decade at Amazon—where he helped forecast AWS and worked inside some of the company’s most operationally demanding businesses—Blake explains how financial discipline, operational depth, and clear narrative-building shape his approach as CFO. The conversation explores how to evolve a beloved product without diluting the brand, why pricing is as much about positioning as revenue, how to communicate go-to-market mechanics without losing the room, and why effective capital allocation accepts that not every big bet needs to land to shape the leader you become.

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SPONSORS:

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LINKS:

Blake on LinkedIn: https://www.linkedin.com/in/blake-grayson-3197043/

Docusign: https://www.docusign.com/

CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/

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

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RELATED EPISODES:

“Steal Your Boss’s Job”: Calendly CFO John McCauley on Leadership, Ownership & Growth

https://youtu.be/VRpTNDIfzPY

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TIMESTAMPS:

00:00:00 Preview and Intro

00:02:39 Sponsors – Fidelity Private Shares | Sage Intacct | Mercury

00:05:09 DocuSign as a Top CFO Tool

00:07:33 From E-Signature to Intelligent Agreement Management

00:09:09 Complexity Before and After a Signature

00:11:02 Cost of Poor Agreement Management

00:12:30 Agreement Oversight and CFO Risk

00:13:28 Pricing: Usage to Seat Models

00:14:12 Enterprise vs SMB Pricing

00:15:00 Sponsors – RightRev | Tipalti | Aleph

00:19:18 Simplicity, Tiers, and IAM Value

00:20:36 Forecasting New Products in a Renewals Base

00:22:13 Modeling Mix Shift and GTM Enablement

00:23:56 Faster Time-to-Value With Intelligent Repositories

00:25:06 Building GTM Muscle for a Platform

00:26:29 Launching IAM in Commercial First

00:27:31 Forecasting Growth vs Cost

00:28:41 Company-Wide Alignment on Priorities

00:30:02 Aligning Investor Messaging With Operations

00:31:20 Staying Focused on Long-Term Outcomes

00:32:27 Customer-First Decision Making

00:33:41 Transparency and What Not to Disclose

00:34:52 Asking Better Metric Questions

00:36:28 Avoiding Data Paralysis

00:38:52 Amazon’s Weekly Business Reviews

00:41:07 Bezos Meetings and the Silent Read

00:45:09 The “Question Mark Email” and Customer Anecdotes

00:50:22 Unit Economics of a Server and Early AWS Bets

00:53:42 Handling Nonpayment Risk

00:55:07 Operational Chaos: Perishables and Regulation

00:57:04 The “No Eggs in California” Story

00:59:31 Treating Escalations as Company Problems

01:00:59 Biggest Career Mistake

01:02:44 Advice to His Younger Self

01:06:34 Tools Finance Uses: Oracle, Bots, IAM, Salesforce, Workday

01:09:21 Wildest Expense Attempts

01:12:32 Closing Thanks and Credits

#RunTheNumbersPodcast #Docusign #CFOInsights #SaaSLeadership #AIManagement

Fire bad customers save great ones | Cassie Young

CJ Gustafson — Mon, 08 Dec 2025 10:03:09 GMT

Cassie Young brings hard earned lessons from a career spanning CRO roles, customer success leadership, turnarounds, and now investing as a General Partner at Primary Venture Partners. She talks about building and rebuilding go to market teams, why sometimes you should fire customers on purpose, and how churn is a lagging indicator that hides deeper retention issues. Cassie shares strong views on overrated metrics like NPS, the incentives that actually drive behavior inside a business, and the myth of finding one perfect KPI. She also brings signature Cassie isms like sunlight is the best disinfectant and the reminder that leaders often get stuck working in the business instead of on it offering practical insights for anyone trying to keep their SaaS metrics from going sideways.

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SPONSORS:

Sage Intacct is the cloud financial management platform that replaces spreadsheets, eliminates manual work, and keeps your books audit-ready—so you can scale without slowing down. It combines accounting, ERP, and real-time reporting for retail, financial services, logistics, tech, professional services, and more. Sage Intacct delivers fast ROI, with payback in under six months and up to 250% return. Rated #1 in customer satisfaction for eight straight years. Visit Sage Intacct and take control of your growth: https://bit.ly/3Kn4YHt

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LINKS:

Cassie on LinkedIn: https://www.linkedin.com/in/cassyoung/

Primary Venture Partners: https://www.primary.vc/

CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/

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

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RELATED EPISODES:

Getting fired 4 times made me a founder | Sam Jacobs of Pavilion

https://youtu.be/8X-JVOF-1A0

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TIMESTAMPS:

00:00:00 Preview and Intro

00:02:30 Sponsors Aleph | Fidelity Private Shares | Sage Intacct

00:05:21 Returning From Pavilion & GTM Summit Takeaways

00:06:49 What Makes a Great Executive

00:11:07 The Importance of True P&L Fluency

00:12:17 First Team Leadership vs Functional Loyalty

00:13:33 Reading the Macro Environment and Market Forces

00:14:29 Sponsors Mercury | RightRev | Tipalti

00:18:26 Applying First Team Leadership in Practice

00:22:24 Churn as a Lagging Indicator

00:24:23 Finding Real Leading Indicators of Renewal

00:25:30 Customer Value as the Only Path to Enterprise Value

00:26:52 Product Adoption Perception and Retention

00:29:16 Price to Value Ratio as a Predictor of Guaranteed Churn

00:30:37 The Ultimate Question What Gets Your Customer Promoted

00:32:33 How NPS Is Actually Calculated

00:34:56 Sailthru’s Minus 26 NPS and What It Signaled

00:37:31 Rebuilding Customer Trust Through Transparency

00:40:24 Why Net and Gross Retention Must Be Paired

00:42:51 Aligning the Executive Team Through a Unified Bonus Plan

00:45:18 Firing Customers When Misaligned Segments Drain the Org

00:49:35 Carrot vs Stick How to Motivate a Modern GTM Org

00:52:31 Why MBO Plans Fail CSMs

01:03:51 Why Time to Value Matters More Than Ever

#RunTheNumbersPodcast #CustomerSuccess #ChurnPrevention #GoToMarket #VentureCapital

From Birding Apps to Billion-Dollar Bundles | Mostly Growth

CJ Gustafson — Sat, 06 Dec 2025 10:02:45 GMT

Mostly Growth on YouTube: https://www.youtube.com/@MostlyGrowth

Mostly Growth on Apple: https://podcasts.apple.com/us/podcast/mostly-growth/id1842238102

Mostly Growth on Spotify: https://open.spotify.com/show/3KDtaLaXx1obFp5PUhZ6V3

In this episode of Mostly Growth, CJ Gustafson and Kyle Poyar bounce between sharp SaaS insights and delightfully weird internet culture. They start with an unexpected dive into competitive bird-watching apps, then break down recent software mergers like Superhuman + Grammarly + Coda and what they signal about scaling, cross-sell strategy, and private equity mechanics. CJ and Kyle explore why PE portfolios are becoming powerful distribution channels for AI solutions, how niche data “signals” are outpacing generic ones in sales, and share hedge-fund-style tactics for uncovering proprietary business information. The conversation rounds out with “business blunders” — from Y-axis chart crimes to clickbait headlines — and a lively discussion on Spotify’s pricing power and how companies should (and absolutely should not) communicate price increases.

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SPONSORS:

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LINKS:

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

CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/

Growth Unhinged: https://www.growthunhinged.com/

Kyle on LinkedIn: https://www.linkedin.com/in/kyle-poyar/

Slacker Stuff: https://www.slackerstuff.com/

Ben on LinkedIn: https://www.linkedin.com/in/slackerstuff/

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RELATED EPISODES: