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50:08ENDax Dasilva on Bootstrapping Lightspeed, Growth and Returning as CEOGast: Dax Dasilva · Moderation: Harry StebbingsThe Lightspeed founder explains how close customer observation shaped its product, why he returned to lead a profitable-growth transition, and what acquisitions left unfinished.
1:07:40ENSaam Motamedi on AI Valuations, Series B Risk and Backing FoundersGast: Saam Motamedi · Moderation: Harry StebbingsThe Greylock partner explains why he sees exuberant AI pricing, questions a universal Series A revenue threshold, and favors founder and market judgment over simple checklists.
45:11ENMark Roberge on Sales Hiring, Unit Economics and Moving UpmarketGast: Mark Roberge · Moderation: Harry StebbingsThe former HubSpot sales leader explains how founders can build a sales motion, align incentives and decide when enterprise customers are worth pursuing.
1:20:50ENJason Lemkin on SaaS Valuations, Private Equity and the Liquidity ProblemGast: Jason Lemkin · Moderation: Harry StebbingsThe SaaStr founder discusses slowing software growth, AI budgets, venture returns and why the next exit may be harder to find.
1:24:54ENJason Lemkin on SaaS Investing, Churn and Seed ValuationsGast: Jason Lemkin · Moderation: Harry StebbingsThe SaaStr founder revisits successful and disappointing deals, explains his diligence process and assesses the economics of seed investing.
59:47ENAaron Levie on AI Agents, SaaS Pricing and the Race Between Startups and IncumbentsGast: Aaron Levie · Moderation: Harry StebbingsThe Box CEO considers how AI might change business workflows, employment and software pricing, and why established companies and startups both have a chance.
52:52ENGirish Mathrubootham on Freshworks Pricing, Products and ScalingGast: Girish Mathrubootham · Moderation: Harry StebbingsThe Freshworks founder shares lessons from self-service software, a multi-product strategy, executive hiring and investing in Indian startups.
1:12:20ENDave Kellogg on SaaS Metrics, Sales Forecasting and Efficient GrowthGast: Dave Kellogg · Moderation: Harry StebbingsThe software executive explains why he separates acquisition, retention and margin, and offers practical ways to improve forecasting and customer relationships.
1:32:52ENJason Lemkin on SaaS, Venture and His 2024 PredictionsGast: Jason Lemkin · Moderation: Harry StebbingsThe SaaStr founder reviews a difficult 2023, reconsiders exit advice and debates what could change for startups in 2024.
55:24ENSteve Goldberg on Selling to CFOs, Reviewing Deals and Building Customer TrustGast: Steve Goldberg · Moderation: Harry StebbingsThe Salesloft revenue leader explains how to find a real champion, demonstrate business outcomes and make renewals part of the sales process.
1:25:06ENTooey Courtemanche on Procore's Long Road to Growth and the Work of LeadingGast: Tooey Courtemanche · Moderation: Harry StebbingsThe construction software founder discusses surviving a slow market, building a product platform, delegating and balancing a company with family life.
57:34ENChris Degnan on Building Snowflake's Sales Team from the First CustomerGast: Chris Degnan · Moderation: Harry StebbingsSnowflake's revenue chief explains prospecting, customer feedback, forecasting and his unconventional view of customer success.
50:31ENEd Sim on Seed Valuations, Inception Investing and Reserving for GrowthGast: Ed Sim · Moderation: Harry StebbingsThe Boldstart founder explains his early financing framework, the risks of excess capital and why follow-on discipline matters.
54:54ENJason Lemkin, Woody Marshall and Deven Parekh Debate Growth Investing and IPOsGast: Jason Lemkin, Woody Marshall, Deven Parekh · Moderation: Harry StebbingsThe investors examine valuation resets, structured rounds, profitability and the uncertain reopening of public markets in 2023.
1:12:29ENJason Lemkin and Rick Zullo Debate Venture Fund Size, Paper Marks and Founder RelationshipsGast: Jason Lemkin, Rick Zullo · Moderation: Harry StebbingsThe investors disagree over pitching and portfolio construction while examining how fund economics shape founders, boards and returns.
1:03:10ENJason Lemkin, Sam Lessin and Frank Rotman Debate the Future of Seed InvestingGast: Jason Lemkin, Sam Lessin, Frank Rotman · Moderation: Harry StebbingsThe investors disagree over startup financing, fund size and founder support while examining how seed prices and capital efficiency affect returns.
1:15:36ENJason Lemkin on Seed Investing, Due Diligence and the 2023 Venture MarketGast: Jason Lemkin · Moderation: Harry StebbingsThe SaaStr founder discusses early-stage valuations, founder support, growth financing and a conditional prediction for the 2024 IPO market.
54:18ENAlex Bouaziz on Building Deel, Global Hiring and Scaling OperationsGast: Alex Bouaziz · Moderation: Harry StebbingsThe Deel CEO discusses execution speed, remote teams, customer feedback and the trade-offs of rapid growth.
57:27ENJason Lemkin on SaaS Growth, Venture Funding and the 2023 ResetGast: Jason Lemkin · Moderation: Harry StebbingsThe SaaStr founder discusses capital efficiency, marketing, private valuations and limited-partner expectations during an uncertain venture market.
1:13:12ENDes Traynor on Intercom, Product Strategy and the Real Cost of GrowthGast: Des Traynor · Moderation: Harry StebbingsThe Intercom co-founder discusses defensibility, second products, enterprise buyers and the lessons he has learned as an operator and angel investor.
1:19:33ENDharmesh Shah on Culture Debt, SMB Strategy and Building HubSpotGast: Dharmesh Shah · Moderation: Harry StebbingsThe HubSpot co-founder discusses treating culture as a product, testing demand early and deciding when to build a second product.
1:13:37ENTen Hot Takes From a Bootstrapped SaaS Founder: Pricing, Retention, Tempo and the Middle of the FunnelGast: Patrick Campbell · Moderation: Lenny RachitskyPatrick Campbell, who sold ProfitWell for more than $200 million without outside funding, runs through ten operating topics, from team culture and bootstrapping to pricing, churn and freemium.
1:06:47ENStop Pushing Customers Through a Funnel: Georgiana Laudi's Customer-Led Growth PlaybookModeration: Lenny RachitskyHow to replace pirate metrics with customer research, jobs-to-be-done, measurable value milestones, and messaging that actually converts.









