Run the Numbers

CJ Gustafson
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Oct 11, 2025 • 47min

How to Crush Your Keynote (Even If You’re Dying Inside)

Get ready for conference season with tips on nailing your keynote speech—like choosing the perfect walkout song! Discover what AI startups are really spending money on and the struggles of measuring AI ROI. The hosts dive into SaaS pricing strategies, including bundling AI features for higher prices. They also discuss quirky insights from late-night reads on sports and economics. Plus, hear about the fascinating architectural history behind Amsterdam's narrow houses and its relation to pricing dynamics.
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5 snips
Oct 9, 2025 • 1h 3min

From Take-Privates to AI: Mapping the New Market Cycle with Scott Voss

Scott Voss, Managing Partner at HarbourVest, explores the evolving landscape of private and public markets. He highlights the rise of mega ventures like SpaceX, contrasting them with traditional firms. Voss dives into the surge of take-private deals, explaining the strategic pivot companies make when escaping quarterly pressures. He discusses the vital role of private credit as a market player and its implications for liquidity. Lastly, he sheds light on how AI deals are reshaping investment strategies, marking an exciting new phase in private equity.
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8 snips
Oct 6, 2025 • 58min

From Credit Karma to Notion: CFO Rama Katkar on Leading Finance Through Every Growth Stage

Rama Katkar, the CFO of Notion and former finance leader at Credit Karma and Instacart, discusses building modern finance functions in fast-growing tech companies. She dives into Notion’s innovative pricing strategies and the importance of nurturing free users to drive growth. Rama shares insights on navigating M&A during turbulent times and outlines her forecasting framework for product-led growth. She emphasizes aligning product metrics with financial outcomes and the value of clear storytelling in finance.
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Oct 4, 2025 • 57min

SEO’s Collapse, Job Hunt Grind & Cone King Bob

The conversation dives into the decline of traditional SEO, questioning if AI Engine Optimization can rescue traffic woes. The hosts tackle the relevance of the T2D3 growth model in the era of fast-paced AI startups and their dubious revenue claims. The tech job market is brutally competitive, with tips for candidates buried under heaps of applications. Board members are described as quietly disengaging as growth slows, and the trio humorously critiqued LinkedIn faux pas, making for a lively discussion on the state of modern business.
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Oct 2, 2025 • 57min

Running a Company Like It Could Go Public Tomorrow with CFO Chad Gold

Chad Gold, CFO of FullStory and a veteran in SaaS finance with previous roles at G2 and SalesLoft, shares his insights on operating like a public company. He discusses why companies are staying private longer and the impact of private credit on CFO strategies. Chad dives into evolving pricing models, emphasizing the influence of sales incentives on revenue quality. He also reflects on valuable lessons from his retail days at Home Depot that continue to guide his decision-making in SaaS today, blending operational rigor with intuition.
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Sep 27, 2025 • 56min

Prompt Anxiety, Sad Dinners, & the $8B Question

Dive into the quirks of startup culture with tales of sad LinkedIn dinners and baffling AI-driven UX trends. Explore the eyebrow-raising case of a $613M company pushing for an $8B valuation and whether referral programs are a sustainable growth strategy or a marketing trap. The hosts debate the implications of 'prompt anxiety' in software and the ethics of disclosing AI-generated content. Plus, learn about Arnold Schwarzenegger's surprising comedy debut and how Reese Witherspoon cleverly uses her book club to fuel her media empire.
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Sep 25, 2025 • 1h 19min

Cowboy Forecasting: The Power of Fast Informed Estimates on the Back of an Envelope

Kevin Drost, CFO of New Era ADR and former chief strategy officer at Reverb, blends his music background with finance insights. He champions 'cowboy forecasting,' a simple yet effective method for early-stage startups that can outperform complex models. Drost explores the disruption of traditional legal pricing through flat fees and faster dispute resolution. He emphasizes the importance of every team member understanding finance, and he shares valuable lessons from his journey, including the benefits of starting a business young.
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Sep 22, 2025 • 51min

The Hidden ROI of Generosity: Meghan McKenna on How Human Connection Closes Deals

In this insightful discussion, Meghan McKenna, founder of Females in Finance and a seasoned banker, delves into the power of human connections in finance. She emphasizes a people-first approach, highlighting how genuine relationships trump transactional mindsets. Meghan shares her thoughts on the evolution of banking, the rise of modular fintech, and the crucial role of personal connections during the SVB crisis. With candid career reflections and networking insights, she inspires finance professionals to prioritize authenticity and build trust.
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16 snips
Sep 20, 2025 • 58min

996 Workweeks, Exploding AI Bills & The SaaS Payback Problem

Kyle Poyar, a growth and market analyst with a knack for SaaS economics, delves into the exploding costs of AI and the impact on company culture. He tackles the unsustainable 996 workweek trend fueled by rising expenses, explains why usage-based pricing can entrap customers, and discusses the challenges of recouping customer acquisition costs. Poyar also introduces the 'cracked engineer' archetype and draws parallels with subscription models in unexpected places, shedding light on the complexities of today’s market.
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17 snips
Sep 18, 2025 • 1h 13min

“90% of VCs Are Neutral to Negative Value”: Kyle Harrison on the Evolving Game of Venture Capital

Kyle Harrison, General Partner at Contrary and writer of the Investing 101 Substack, shares keen insights into the shifting landscape of venture capital. He discusses the varying incentives between capital agglomerators and cottage keepers, emphasizing how fund size influences strategy. The conversation dives into the ethical complexities of funding rival AI projects and the impact of dilution on founders. Harrison also examines the blurred lines between hype and real business value in AI, highlighting the power of narrative in shaping market perceptions.

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