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1:22:59ENDan Fougere on Building Datadog’s Sales Motion and Protecting PriceGuest Dan Fougere · Host Harry StebbingsThe former Datadog CRO explains qualification, enterprise sales, discount discipline and the people behind a repeatable process.
1:23:01ENPhil Carter on Growth Loops and Consumer Subscription EconomicsGuest Phil Carter · Host Harry StebbingsThe growth advisor explains acquisition, retention, paywalls and pricing, and why sustainable consumer subscriptions require more than buying traffic.
1:24:54ENJason Lemkin on SaaS Investing, Churn and Seed ValuationsGuest Jason Lemkin · Host Harry StebbingsThe SaaStr founder revisits successful and disappointing deals, explains his diligence process and assesses the economics of seed investing.
52:52ENGirish Mathrubootham on Freshworks Pricing, Products and ScalingGuest Girish Mathrubootham · Host Harry StebbingsThe Freshworks founder shares lessons from self-service software, a multi-product strategy, executive hiring and investing in Indian startups.
1:03:31ENPeter Wagner on Venture Cycles, Founders and Price DisciplineGuest Peter Wagner · Host Harry StebbingsThe Wing founding partner reflects on decades of investing, the Snowflake round he did not lead and the risks of capital-intensive businesses.
1:01:37ENDoug Adamic on Sales Discovery, Pipeline Quality and Why He Resists DiscountingGuest Doug Adamic · Host Harry StebbingsThe Brex revenue leader explains how he connects customer outcomes to urgency, coaches sales teams and builds a repeatable process.
30:53ENMark Cuban on Cost Plus Drugs, Hiring and Healthcare PricingGuest Mark Cuban · Host Harry StebbingsIn a 2022 interview, Cuban describes the pharmacy’s early pricing model, his self-funded venture and his views on the US healthcare system.









