Run the Numbers

In this episode, CJ sits down with Dr. Julie Gurner, the author behind the Substack Ultra Successful, to explore how top CEOs, CFOs, and entrepreneurs manage their ambition, goals, and self-talk. They examine if being hard on yourself necessary for success and Dr. Gurner shares helpful reframes that can be used to overcome negative self-talk. The conversation delves into the concept of “haunting agitation,” a term she uses to describe the hunger and ambition driving high performers. Building on this, she introduces the idea of empirical guardrails to keep one’s ambition in check. Dr. Gurner also breaks down the difference between “motivated” individuals and those who go “all in,” explaining how full commitment can lead to exponential growth. They touch on the surprising power of seemingly “boring” and discuss what the “build in public” movement gets wrong. Lastly, they talk about the art of saying no to opportunities that, while tempting, may distract you from your core focus. Tune in for expert advice on channeling your drive toward meaningful success.

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

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SPONSORS:

Mercury is the fintech ambitious companies use for banking and all their financial workflows. With a powerful bank account at the center of their operations, companies can make better financial decisions and ensure that every dollar spent aligns with company priorities. That's why over 100K startups choose Mercury to confidently run all their financial operations with the precision, control, and focus they need to operate at their best. Learn more at mercury.com.

Mercury is a financial technology company, not a bank. Banking services provided by Choice Financial Group and Evolve Bank & Trust®; Members FDIC. 

NetSuite provides financial software for all your business needs. More than 38,000 thousand companies have already upgraded to NetSuite, gaining visibility and control over their financials, inventory, HR, eCommerce, and more. If you're looking for an ERP platform ✅ NetSuite: https://netsuite.com/metrics and get a customized KPI checklist. 

Maxio is the only billing and financial operations platform that was purpose built for B2B SaaS. They're helping SaaS finance teams automate billing and revenue recognition, manage collections and payments, and put together investor grade reporting packages. 🚀 Request a demo at www.maxio.com/runthenumbers for 10% off your first year.

Leapfin is accounting automation software that automatically prepares and posts reliable journal entries. High-growth businesses like Reddit, Canva, and Seat Geek choose Leapfin to eliminate manual tasks, accelerate month-end close, and enable accounting leaders to provide faster insights to help their companies grow. To automatically standardize your revenue data with measurable business impact, check out leapfin.com today. 

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.

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FOLLOW US ON X:

@cjgustafson222 (CJ)

@DrGurner (Dr. Julie Gurner) 

SUBSTACK:

mostlymetrics.com (Mostly metrics)

drgurner.substack.com (Ultra Successful) 

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TIMESTAMPS:(00:00) Preview and Intro(02:56) Sponsor - Mercury | NetSuite(05:28) Overcoming Negative Self-Talk(08:51) Reframing Fear as Excitement(13:26) Haunting Agitation(16:59) Sponsor - Maxio | Leapfin | Planful(20:06) Being in Your Business Versus on Your Business(23:58) The Impact of Haunting Agitation on Relationships(26:51) Moving Goal Posts and Setting up Metrics(30:52) Hitting the Goal Versus the Feeling of Forward Momentum(32:09) Alan Greenberg’s PSDs and What That Means(35:15) The Motivated Versus the All-in(41:02) Hangups for Motivated People(43:02) The Sunk Cost Fallacy(45:23) The Worst-Case Scenario Question(48:02) “Protecting Downside” Versus Having a Plan B(49:12) The Rewards of Going All-in(52:02) The Strategic Advantage of Boring(55:48) What the “Build in Public” Movement Gets Wrong(57:13) The Art of Saying No to Good Opportunities(59:28) Overcoming People Pleasing(01:02:03) Wrap

In this episode, Joseph Floyd from Emergence Capital joins CJ to dive into the venture capital firm’s latest benchmarking report, offering insights into the enterprise software space. Compiled from over 650 responses from Emergence Capital’s portfolio and additional seed firms, the report covers a range of companies from pre-seed to pre-IPO. Joe discusses key trends in AI adoption, highlighting the contrast between companies incorporating AI and those actually generating revenue from it. The conversation also touches on efficiency metrics like net dollar retention rates, and whether the rule of 40 still holds relevance. Joe sheds light on the struggles faced by companies in the "messy middle," grappling with slower growth and burning cash. Other topics include the lengthening time between early-stage funding rounds, the shift in fundraising dynamics, and why some founders are rethinking their need for venture capital altogether. Tune in for a comprehensive look at the current state of enterprise software and the challenges ahead.

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

—

SPONSORS:

NetSuite provides financial software for all your business needs. More than 38,000 thousand companies have already upgraded to NetSuite, gaining visibility and control over their financials, inventory, HR, eCommerce, and more. If you're looking for an ERP platform ✅ NetSuite: https://netsuite.com/metrics and get a customized KPI checklist. 

Maxio is the only billing and financial operations platform that was purpose built for B2B SaaS. They're helping SaaS finance teams automate billing and revenue recognition, manage collections and payments, and put together investor grade reporting packages. 🚀 Request a demo at www.maxio.com/runthenumbers for 10% off your first year.

Leapfin is accounting automation software that automatically prepares and posts reliable journal entries. High-growth businesses like Reddit, Canva, and Seat Geek choose Leapfin to eliminate manual tasks, accelerate month-end close, and enable accounting leaders to provide faster insights to help their companies grow. To automatically standardize your revenue data with measurable business impact, check out leapfin.com today. 

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.

Mercury is the fintech ambitious companies use for banking and all their financial workflows. With a powerful bank account at the center of their operations, companies can make better financial decisions and ensure that every dollar spent aligns with company priorities. That's why over 100K startups choose Mercury to confidently run all their financial operations with the precision, control, and focus they need to operate at their best. Learn more at mercury.com.

Mercury is a financial technology company, not a bank. Banking services provided by Choice Financial Group and Evolve Bank & Trust®; Members FDIC.

—

FOLLOW US ON X:

@cjgustafson222 (CJ)

@thejoefloyd (Joseph Floyd)

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TIMESTAMPS:(00:00) Preview and Intro(02:36) Sponsor - NetSuite | Maxio(04:55) Benchmarking Report Background(05:56) Incorporating AI Versus Making Money Off It(09:23) Investing in R&D for AI and How This Affects P&L(11:12) The Real Speed of the Evolution of AI(13:46) The Lasting Power of the Current AI Leaders(15:29) Sponsor - Leapfin | Planful | Mercury(18:53) Growth Versus Profitability and the Rule of 40(20:42) Why the Days of 150% NDR Are Gone(22:53) Why Mid-Stage Companies Are Hardest Hit(24:24) Subscription Based Versus Usage-Based GDR(25:42) Hybrid Pricing Models and AI(27:08) Gross Dollar Retention Rates Versus Net Dollar Retention Rates(27:50) Why Mid-Market Buyers Are Pulling Back(30:37) Impacts on $5 Million - $20 Million ARR Companies(35:04) The Growth Slowdown in $50 Million - $250 Million ARR Companies(37:43) Companies Quietly Shutting Down(40:12) The Effect on Employees(41:02) The Impact of Zombie Companies on the Economy(42:39) The LP-GP Relationship and Returning Capital(44:19) The Denominator Effect(45:27) Public Markets Versus Private Markets(46:26) Why Time Between Early-Stage Rounds Is Lengthening(47:29) Why Some Companies Shouldn’t Raise Venture(50:42) “The Secret Playbook” Refresh

In this episode, CJ interviews Philip Brenckle, CFO of West Shore Home, a company that's revolutionizing the way that people are remodeling their homes. Phil shares insights on the home remodeling market, an unconsolidated industry with a total addressable market (TAM) of $500 billion. He explains how West Shore Home is growing its TAM by meeting customers where they are, before shedding light on the company’s model and its direct-to-consumer component. Phil dives into the role of credit in home remodels and West Shore Home’s financing module. He also breaks down the average split between labor and materials, why the company chooses to work with W2 employees over subcontractors, and how they determine pricing. Additionally, Phil talks about how M&A is part of their strategy, the types of acquisition deals West Shore Home does, and why you should only work with great advisors, before giving tips on how to effectively build relationships with banking partners. 

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

—

SPONSORS:

Maxio is the only billing and financial operations platform that was purpose built for B2B SaaS. They're helping SaaS finance teams automate billing and revenue recognition, manage collections and payments, and put together investor grade reporting packages. 🚀 Request a demo at www.maxio.com/runthenumbers for 10% off your first year.

Leapfin is accounting automation software that automatically prepares and posts reliable journal entries. High-growth businesses like Reddit, Canva, and Seat Geek choose Leapfin to eliminate manual tasks, accelerate month-end close, and enable accounting leaders to provide faster insights to help their companies grow. To automatically standardize your revenue data with measurable business impact, check out leapfin.com today. 

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.

Mercury is the fintech ambitious companies use for banking and all their financial workflows. With a powerful bank account at the center of their operations, companies can make better financial decisions and ensure that every dollar spent aligns with company priorities. That's why over 100K startups choose Mercury to confidently run all their financial operations with the precision, control, and focus they need to operate at their best. Learn more at mercury.com.

Mercury is a financial technology company, not a bank. Banking services provided by Choice Financial Group and Evolve Bank & Trust®; Members FDIC.

NetSuite provides financial software for all your business needs. More than 38,000 thousand companies have already upgraded to NetSuite, gaining visibility and control over their financials, inventory, HR, eCommerce, and more. If you're looking for an ERP platform ✅ NetSuite: https://netsuite.com/metrics and get a customized KPI checklist. 

—

FOLLOW US ON X:

@cjgustafson222 (CJ)

—

TIMESTAMPS:(00:00) Preview and Intro(02:50) Sponsor - Maxio | Leapfin(05:59) West Shore Home’s TAM(09:07) Growing the TAM(12:52) The D2C Nature of West Shore Home(16:24) Home Remodels and Credit Financing(18:53) Sponsor - Planful | Mercury | NetSuite(21:22) How Credit Works at West Shore Home(23:45) The Cost of a Financing Module(28:56) W2 Employees Versus Subcontractors(31:01) The Split Between Labor and Materials(34:31) Determining Pricing(37:31) M&A and Consolidation in the Home Remodeling Industry(42:29) Structures West Shore Home Uses for M&A Deals(45:29) Why You Shouldn’t Cut Corners on Great Advisors(48:58) Tips for Working With Bankers(52:10) Long-Ass Lightning Round: Extreme Ownership(55:08) Finance Software Stack(56:29) Craziest Expense Story(57:55) Closing Statistics on the Home Remodeling TAM

Amanda Whalen, CFO of Klaviyo, joins CJ in this episode for a deep dive into the roadshow, the IPO process, and ringing that bell. Amanda reflects on the company’s bold decision to go public last year, despite a challenging macroeconomic environment. She shares the factors that guided the management team's timing, the valuation criteria they used to determine the offering price, and how they prepared for it. Amanda provides insight into the IPO journey, discussing everything from choosing a banker to prepping for earnings calls and building the book for investors. The conversation also explores the evolving CFO role and what Amanda means by the term "CFO plus”. She offers valuable insights on what distinguishes great CFOs from good ones, along with tips for recruiting and developing top talent. Tune in to find out why good CFOs are like dolphins, why you should look at your career like a bingo card, and hear other practical advice and entertaining anecdotes. 

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

—

SPONSORS:

Leapfin is accounting automation software that automatically prepares and posts reliable journal entries. High-growth businesses like Reddit, Canva, and Seat Geek choose Leapfin to eliminate manual tasks, accelerate month-end close, and enable accounting leaders to provide faster insights to help their companies grow. To automatically standardize your revenue data with measurable business impact, check out leapfin.com today.

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.

Mercury is the fintech ambitious companies use for banking and all their financial workflows. With a powerful bank account at the center of their operations, companies can make better financial decisions and ensure that every dollar spent aligns with company priorities. That's why over 100K startups choose Mercury to confidently run all their financial operations with the precision, control, and focus they need to operate at their best. Learn more at mercury.com.

Mercury is a financial technology company, not a bank. Banking services provided by Choice Financial Group and Evolve Bank & Trust®; Members FDIC.

NetSuite provides financial software for all your business needs. More than 38,000 thousand companies have already upgraded to NetSuite, gaining visibility and control over their financials, inventory, HR, eCommerce, and more. If you're looking for an ERP platform ✅ NetSuite: https://netsuite.com/metrics and get a customized KPI checklist. 

Maxio is the only billing and financial operations platform that was purpose built for B2B SaaS. They're helping SaaS finance teams automate billing and revenue recognition, manage collections and payments, and put together investor grade reporting packages. 🚀 Request a demo at www.maxio.com/runthenumbers for 10% off your first year.

—

FOLLOW US ON X:

@cjgustafson222 (CJ)

—

TIMESTAMPS:(00:00) Preview and Intro(02:07) Sponsor - Leapfin | Planful(04:28) The Right Time for a Business to Go Public(09:55) Reasons to Go Public(12:01) Preparing to Go Public(14:41) Earnings Calls(17:54) Sponsor - Mercury | NetSuite | Maxio(20:44) Evaluating the Initial Offering Price(23:47) Deciding Factors When Choosing a Banker(27:33) Advisors You Work With During an IPO(29:57) How Dual Voting Shares Work(31:26) Building the Book for Investors(33:26) What to Expect From a Roadshow(35:44) The CFO Plus Role(38:00) The Qualities of Good CFOs(39:24) Recruiting and Developing Talent(42:47) Recommended Career Detours and Specialties(46:39) Long-Ass Lightning Round: Big Mistakes and Advice(49:25) Finance Software Stack

After requests for another pricing episode, CJ sits down with returning guest Jason Kap, the founder and CEO of Blue Rocket, a long-tenured Microsoft leader, and an expert in pricing and packaging. Together, they take a deep dive into the evolution of software pricing, tracing its journey from the early days of buying hardware and software together to buying software separately, and all the way through the eras to the emergence of SaaS and today’s usage-based and hybrid models. Jason provides a detailed look at the shifts in the industry, including the rise of application service providers and outsourced infrastructure. As they discuss the current landscape, they highlight the importance of transparency and value abstraction. Then they look to the future with advice on how CFOs can navigate pricing in the new era of AI. Packed with practical insights, this episode offers a comprehensive guide for anyone looking to understand the past, present, and future of software pricing and packaging.

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

—

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.

Mercury is the fintech ambitious companies use for banking and all their financial workflows. With a powerful bank account at the center of their operations, companies can make better financial decisions and ensure that every dollar spent aligns with company priorities. That's why over 100K startups choose Mercury to confidently run all their financial operations with the precision, control, and focus they need to operate at their best. Learn more at mercury.com.

Mercury is a financial technology company, not a bank. Banking services provided by Choice Financial Group and Evolve Bank & Trust®; Members FDIC.

NetSuite provides financial software for all your business needs. More than 38,000 thousand companies have already upgraded to NetSuite, gaining visibility and control over their financials, inventory, HR, eCommerce, and more. If you're looking for an ERP platform ✅ NetSuite: https://netsuite.com/metrics and get a customized KPI checklist. 

Maxio is the only billing and financial operations platform that was purpose built for B2B SaaS. They're helping SaaS finance teams automate billing and revenue recognition, manage collections and payments, and put together investor grade reporting packages. 🚀 Request a demo at www.maxio.com/runthenumbers for 10% off your first year.

Leapfin is accounting automation software that automatically prepares and posts reliable journal entries. High-growth businesses like Reddit, Canva, and Seat Geek choose Leapfin to eliminate manual tasks, accelerate month-end close, and enable accounting leaders to provide faster insights to help their companies grow. To automatically standardize your revenue data with measurable business impact, check out leapfin.com today. 

—

FOLLOW US ON X:

@cjgustafson222 (CJ)

—

TIMESTAMPS:(00:00) Preview and Intro(02:26) Sponsor - Planful | Mercury(04:51) Hardware and Software Sold Together(08:11) Software Sold for Hardware(11:48) The Origins of the Enterprise Agreement(15:44) Sponsor - NetSuite | Maxio | Leapfin(18:42) Application Service Providers(23:00) The Evolution of AWS, Google, and Salesforce(27:06) Outsourced Infrastructure and SaaS(33:54) Adobe as the Prime Example of Moving to SaaS(36:32) The Financial Implications of Transitioning to SaaS(38:46) Shelfware in the Next Wave(41:01) Usage-based Pricing(44:25) The Hybrid Model(48:29) Tips for Billing and Overages(52:14) Predictions for the Next Wave: How to Price AI(54:18) Wrap

In this episode, CJ talks with Kingsley Afemikhe, CFO of Shield AI, a company pioneering the future of autonomous jets. Together, they dive deep into the defense tech industry, exploring the critical differences between autonomous vehicles and flight technology, and how innovative private tech companies like Shield AI are driving advancements in the sector. Kingsley provides an insider’s look into Shield AI’s business model, its customer base, and the intricate challenges of managing a hardware/software interface business in such a high-stakes field. He also shares his extensive experience in international deal-making, offering valuable insights into the art of navigating cultural complexities during negotiations and the importance of building a personal board of directors. The discussion wraps up with forward-looking thoughts on how AI could revolutionize careers, bringing a new wave of change to the industry and beyond. Tune in to hear Kingsley’s expert insights on the future of defense technology and its broader impacts.If you're looking for an ERP head to NetSuite: https://netsuite.com/metrics and get a customized KPI checklist.

—

SPONSORS:

Mercury is the fintech ambitious companies use for banking and all their financial workflows. With a powerful bank account at the center of their operations, companies can make better financial decisions and ensure that every dollar spent aligns with company priorities. That's why over 100K startups choose Mercury to confidently run all their financial operations with the precision, control, and focus they need to operate at their best. Learn more at mercury.com.

Mercury is a financial technology company, not a bank. Banking services provided by Choice Financial Group and Evolve Bank & Trust®; Members FDIC.

NetSuite provides financial software for all your business needs. More than 38,000 thousand companies have already upgraded to NetSuite, gaining visibility and control over their financials, inventory, HR, eCommerce, and more. If you're looking for an ERP platform ✅ NetSuite: https://netsuite.com/metrics and get a customized KPI checklist. 

Maxio is the only billing and financial operations platform that was purpose built for B2B SaaS. They're helping SaaS finance teams automate billing and revenue recognition, manage collections and payments, and put together investor grade reporting packages. 🚀 Request a demo at www.maxio.com/runthenumbers for 10% off your first year.

Leapfin is accounting automation software that automatically prepares and posts reliable journal entries. High-growth businesses like Reddit, Canva, and Seat Geek choose Leapfin to eliminate manual tasks, accelerate month-end close, and enable accounting leaders to provide faster insights to help their companies grow. To automatically standardize your revenue data with measurable business impact, check out leapfin.com today. 

Planful is a financial performance management platform designed to streamline financial tasks for businesses. It helps with budgeting, closing the books, and financial reporting, all on a cloud-based platform. By improving the efficiency and accuracy of these processes, Planful allows businesses to make better financial decisions. Find out more at www.planful.com/metrics.

—

FOLLOW US ON X:

@cjgustafson222 (CJ)

—

TIMESTAMPS:(00:00) Preview and Intro(02:39) Sponsor - Mercury | NetSuite(06:00) The Autonomous Vehicle Versus Autonomous Flying Market(08:13) Innovation in the Defense Industry(11:00) Who Is Buying Shield AI Products(13:47) Building a Career in Defense(16:04) How Shield AI Makes Money(17:54) Sponsor - Maxio | Leapfin | Planful(20:59) Putting Together Government Proposals(23:44) Managing Working Capital and Debt(26:25) The OODA Loop: Observe, Orient, Decide, Act(27:31) Other Key Leaders in the Defense Industry(28:31) Cross-Cultural Deal-Making(34:53) Raising More Money Versus Less(36:22) Selecting a Personal Board of Directors(39:11) Career Building and Volatility(40:29) AI Optimism and AI FOMO(44:09) Long-Ass Lightning Round: Insurance Mistakes(46:55) Finance Software Stack(48:31) Craziest Expense Story

In this bucket list interview, CJ speaks with Larry Roseman, the CFO of Thumbtack, who shares his deep understanding of running marketplace businesses at scale. They explore Thumbtack's business model and monetization strategy, discussing the customer acquisition cost for both service providers and homeowners. Larry explains why going broad rather than niche can be fundamental for marketplace success, offering a counterintuitive view to that of many marketplace experts. He also talks about the flywheels Thumbtack has developed over time and the company’s shift towards becoming a proactive operating system for homes instead of a reactive marketplace. Additionally, Larry offers valuable insights on value creation from a CFO's perspective, emphasizing the importance of making NPV-positive decisions and the strategic role of the CFO in guiding big business decisions. Hear about the crises that Larry has seen in his career and his advice to “never waste a good crisis”.

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

—

SPONSORS:

NetSuite provides financial software for all your business needs. More than 37,000 thousand companies have already upgraded to NetSuite, gaining visibility and control over their financials, inventory, HR, eCommerce, and more. If you're looking for an ERP platform ✅ NetSuite: https://netsuite.com/metrics and get a customized KPI checklist. 

Maxio is the only billing and financial operations platform that was purpose built for B2B SaaS. They're helping SaaS finance teams automate billing and revenue recognition, manage collections and payments, and put together investor grade reporting packages. 🚀 Request a demo at www.maxio.com/runthenumbers for 10% off your first year.

Leapfin is accounting automation software that automatically prepares and posts reliable journal entries. High-growth businesses like Reddit, Canva, and Seat Geek choose Leapfin to eliminate manual tasks, accelerate month-end close, and enable accounting leaders to provide faster insights to help their companies grow. To automatically standardize your revenue data with measurable business impact, check out leapfin.com today. 

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.

Mercury is the fintech ambitious companies use for banking and all their financial workflows. With a powerful bank account at the center of their operations, companies can make better financial decisions and ensure that every dollar spent aligns with company priorities. That's why over 100K startups choose Mercury to confidently run all their financial operations with the precision, control, and focus they need to operate at their best. Learn more at mercury.com.

Mercury is a financial technology company, not a bank. Banking services provided by Choice Financial Group and Evolve Bank & Trust®; Members FDIC.

—

FOLLOW US ON X:

@cjgustafson222 (CJ)

—

TIMESTAMPS:(00:00) Preview and Intro(02:31) Sponsor – NetSuite | Maxio(06:13) How Thumbtack Makes Money(09:30) Being Broad as the Key to Marketplace Success(12:31) Charging for the LTV(13:45) The Evolution of the Marketplace Industry(16:21) Sponsor – Leapfin | Planful | Mercury(19:40) Thumbtack’s Two North Stars(21:31) CAC and LTV: Supplier versus Household(23:59) Flywheels versus Network Effects(25:52) Thumbtack’s Evolution: Reactive to Proactive(29:09) Thumbtack’s North Star Metric(32:34) Making the Right NPV Positive Decision(36:43) Helping the C-suite Size Up Big Bets(39:20) Learnings from Crises(40:44) Share-Based Compensation(45:37) Long-Ass Lightning Round: CAC Framework Regrets(50:33) Finance Software Stack(51:53) Craziest Expense Story

In this episode, CJ sits down with Eric Newcomer, who runs “Newcomer," or newcomer.co, the largest independent media outlet focused on venture capital. They delve into the art of crafting fundraising announcements, particularly from the CFO’s angle when pitching a company’s raise to the media. The conversation explores the unique appeal of venture capitalists as a subject matter and some of the big stories and personalities that Eric has featured. The discussion also covers the fascinating trend of media companies morphing into VCs, VCs morphing into media companies, and the reasons behind this. Eric sheds light on how a good fundraising announcement should work, how this relates to a company's efforts to attract talent, and how and why to build relationships with the media when not fundraising. Drawing from Eric’s vast industry experience, hear his perspectives on what makes a story compelling and shareable, lessons from his own media business, and his insights on all things venture capital. 

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

—

SPONSORS:

Maxio is the only billing and financial operations platform that was purpose built for B2B SaaS. They're helping SaaS finance teams automate billing and revenue recognition, manage collections and payments, and put together investor grade reporting packages. 🚀 Request a demo at www.maxio.com/runthenumbers for 10% off your first year.

Leapfin is accounting automation software that automatically prepares and posts reliable journal entries. High-growth businesses like Reddit, Canva, and Seat Geek choose Leapfin to eliminate manual tasks, accelerate month-end close, and enable accounting leaders to provide faster insights to help their companies grow. To automatically standardize your revenue data with measurable business impact, check out leapfin.com today. 

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.

Mercury is the fintech ambitious companies use for banking and all their financial workflows. With a powerful bank account at the center of their operations, companies can make better financial decisions and ensure that every dollar spent aligns with company priorities. That's why over 100K startups choose Mercury to confidently run all their financial operations with the precision, control, and focus they need to operate at their best. Learn more at mercury.com.

Mercury is a financial technology company, not a bank. Banking services provided by Choice Financial Group and Evolve Bank & Trust®; Members FDIC.

NetSuite provides financial software for all your business needs. More than 37,000 thousand companies have already upgraded to NetSuite, gaining visibility and control over their financials, inventory, HR, eCommerce, and more. If you're looking for an ERP platform ✅ NetSuite: https://netsuite.com/metrics and get a customized KPI checklist. 

—

FOLLOW US ON X:

@cjgustafson222 (CJ)

@EricNewcomer (Eric Newcomer) 

—

TIMESTAMPS:

(00:00) Preview and Intro(02:03) Sponsor – Maxio | Leapfin(05:37) What Makes Venture Capitalists So Intriguing to Cover(08:06) Big Stories and Personalities Covered on Newcomer(11:21) a16z’s Moves into the Media Space(12:37) Conflicts of Interest in the Media Space(14:45) The Convergence of Media and Investing(16:56) Sponsor – Planful | Mercury | NetSuite(21:35) How Eric Gets Tips and Scoops(23:07) How a Good Fundraising Announcement Should Work(26:17) Fundraising Announcements and Attracting Talent(29:33) “Off the Record” Relationships with the Media(36:05) Eric’s Database of Investor Profiles and the Value of Lists(42:12) Differentiated Competitive Moats for Companies versus VCs(43:31) Eric’s Decision to Monetize via Subscriptions(49:42) Regrets from the First Year of Eric’s Business(51:30) Building Newcomer’s Subscriber Base(52:25) The Next Big Thing versus Evergreen Content(56:15) Whether VC Is Bigger or Smaller Than Eric Expected(58:50) Wrap

In this episode, CJ interviews Bryan Morris, CFO of Demandbase, for an in-depth discussion on the complexities of OKRs (Objectives and Key Results). As the planning season for 2025 kicks into gear, Bryan shares his insights on setting the right OKRs, aligning them across departments, and explaining why they often lose momentum. He discusses his approach to tracking OKRs, the tools he uses, and his thoughts on making midyear adjustments. Bryan also talks about the value of weekly written executive team updates and formats for efficient meetings. Bryan, a strong advocate of personality tests, unpacks how they enhance talent management, before shedding light on the tough side of leadership and how to approach moving people out of the company when it’s not working. The episode wraps up with Bryan’s insights on a CFO’s decision-making power over an organization’s software stack, including the risks of tool consolidation and the hidden costs of poor tech choices.

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

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SPONSORS:

Leapfin is accounting automation software that automatically prepares and posts reliable journal entries. High-growth businesses like Reddit, Canva, and Seat Geek choose Leapfin to eliminate manual tasks, accelerate month-end close, and enable accounting leaders to provide faster insights to help their companies grow. To automatically standardize your revenue data with measurable business impact, check out leapfin.com today. 

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.

Mercury is the fintech ambitious companies use for banking and all their financial workflows. With a powerful bank account at the center of their operations, companies can make better financial decisions and ensure that every dollar spent aligns with company priorities. That's why over 100K startups choose Mercury to confidently run all their financial operations with the precision, control, and focus they need to operate at their best. Learn more at mercury.com.

Mercury is a financial technology company, not a bank. Banking services provided by Choice Financial Group and Evolve Bank & Trust®; Members FDIC.

NetSuite provides financial software for all your business needs. More than 37,000 thousand companies have already upgraded to NetSuite, gaining visibility and control over their financials, inventory, HR, eCommerce, and more. If you're looking for an ERP platform ✅ NetSuite: https://netsuite.com/metrics and get a customized KPI checklist. 

Maxio is the only billing and financial operations platform that was purpose built for B2B SaaS. They're helping SaaS finance teams automate billing and revenue recognition, manage collections and payments, and put together investor grade reporting packages. 🚀 Request a demo at www.maxio.com/runthenumbers for 10% off your first year.

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FOLLOW US ON X:

@cjgustafson222 (CJ)

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TIMESTAMPS:(00:00) Preview and Intro(02:34) Sponsor - Leapfin | Planful(05:04) OKRs in Planning Season(07:55) Department OKRs Versus Company OKRs(10:04) The Pros and Cons Stretch Goals(12:19) When and Where Do OKRs Fail(16:28) Sponsor - Mercury | NetSuite | Maxio(19:52) Adjusting OKRs During the Year(21:50) Tools to Track OKRs(22:41) How Weekly Written Team Updates Work(24:53) Formats for Executive Team Meetings(28:20) Talent Management and the Benefits of Personality Tests(32:49) Soft Skills to Screen for When Hiring(33:45) Advice for Off-boarding People(37:25) CFOs and Company-wide Software Decisions(41:59) The Pros and Cons of Tool Consolidation(44:21) Hidden Costs of Choosing the Wrong Technology(45:40) Tips for Negotiating Software Deals(47:30) Long-ass Lightning Round: Wire Fraud Regrets(49:15) Advice to Bryan’s Younger Self(51:58) Finance Software Stack(52:36) Craziest Expense Story

In this mailbag edition, CJ introduces listeners to Run the Numbers’ first intern. Intern Charlie fills us in on what his internship entails and the nature of the early recruitment process for college internships these days. Then CJ answers questions submitted by listeners. He shares his thoughts on when to join a startup to maximize your equity outcome, where to pull cash from when you need to free up budget, what experience he believes is required to run a $100 million+ SaaS company, whether or not you have to sell to the enterprise to become a public SaaS company, and what he means when he says that the gross profit is where the race starts. CJ talks about his own career path, why he switched from consulting and private equity to operator and CFO, and what he wishes he had known about his skills and potential job paths when he was in college. This episode is full of advice and insights for college students and finance professionals alike.

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

—

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.

Mercury is the fintech ambitious companies use for banking and all their financial workflows. With a powerful bank account at the center of their operations, companies can make better financial decisions and ensure that every dollar spent aligns with company priorities. That's why over 100K startups choose Mercury to confidently run all their financial operations with the precision, control, and focus they need to operate at their best. Learn more at mercury.com.

Mercury is a financial technology company, not a bank. Banking services provided by Choice Financial Group and Evolve Bank & Trust®; Members FDIC.

NetSuite provides financial software for all your business needs. More than 37,000 thousand companies have already upgraded to NetSuite, gaining visibility and control over their financials, inventory, HR, eCommerce, and more. If you're looking for an ERP platform ✅ NetSuite: https://netsuite.com/metrics and get a customized KPI checklist.

Maxio is the only billing and financial operations platform that was purpose built for B2B SaaS. They're helping SaaS finance teams automate billing and revenue recognition, manage collections and payments, and put together investor grade reporting packages. 🚀 Request a demo at www.maxio.com/runthenumbers for 10% off your first year.

Leapfin is accounting automation software that automatically prepares and posts reliable journal entries. High-growth businesses like Reddit, Canva, and Seat Geek choose Leapfin to eliminate manual tasks, accelerate month-end close, and enable accounting leaders to provide faster insights to help their companies grow. To automatically standardize your revenue data with measurable business impact, check out leapfin.com today.

—

FOLLOW US ON X:

@cjgustafson222 (CJ)

—

TIMESTAMPS:(00:00) Preview and Intro(02:32) Sponsor - Planful | Mercury(04:17) Intern Charlie’s Role at Run the Numbers(07:42) When to Join a Startup to Maximize Your Equity Outcome(12:13) Equity at Different Stages of a Company(13:57) Where to Pull Cash From When You Need to Free Up Budget(15:22) Sponsor - NetSuite | Maxio | Leapfin(18:57) Path to Become CFO of a $100 million+ SaaS Company(21:36) Finding “Personal Product Market Fit”(26:53) Selling to the Enterprise to Become a Public SaaS Company(28:15) The Gross Profit is Where the Race Starts(29:47) The Cost of Goods Sold for SaaS Versus Physical Products(31:02) CJ’s Favorite Writers(32:40) What CJ Would Ask a Candidate in an Interview Process but Can’t(36:10) Common Threads in the “Advice to Younger Self” Question(38:04) CJ’s Advice to College Graduates and Junior Year Students