SaaS Interviews with CEOs
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Daily 15-minute interviews with SaaS founders, exploring the data behind today’s fastest-growing SaaS companies. Hear how SaaS CEOs launched their startups and grew them into real businesses – from bootstrapped MVPs to 10,000 customers, pre-revenue to pre-IPO.
Recent Posts
Podcast•Feb 26, 2026•28 min
From $187M Ecommerce to $5M ARR SaaS: Spresso's Post-Bankruptcy Pivot to Enterprise Software | Jared Yaman
In this episode, Jared Gaiman, co‑founder of Boxed and current CEO of Spresso, recounts the rise of Boxed from a $187 M e‑commerce business to its Chapter 11 filing and subsequent pivot to a $5 M ARR SaaS model focused on enterprise software for e‑commerce logistics. He shares hard‑won lessons about the pitfalls of competing with giants on thin margins, the shift away from growth‑at‑all‑costs toward capital efficiency, and the importance of founder equity and secondary liquidity. Gaiman also discusses how Spresso is leveraging technology and AI to deliver more efficient fulfillment solutions, and reflects on the broader evolution of startup financing and founder wealth creation.
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Podcast•Feb 12, 2026•22 min
Bootstrapping to $50M ARR in Vertical SaaS | Vantaca's HOA Software Playbook
In this episode, Ben Currin, CEO of Vantaca, explains how the company bootstrapped a vertical SaaS platform for HOA management from under $1M ARR to $50M ARR, first reaching $5–10M without external funding and then scaling tenfold after a minority...
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Podcast•Dec 24, 2025•25 min
Founder Uses Genius Playbook to Hit $1M Revenue with No Employees
In this episode, Andrew Fennell, founder of Standout CV, shares how he turned a freelance CV service into a bootstrapped SaaS that now attracts 18 million organic visitors, generates $30K MRR and over $1 million in lifetime revenue—all without venture funding. He...
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Podcast•Dec 17, 2025•25 min
Bootstrapping Through War to $6M ARR: A SaaS Founder Story
Vlad Malanin, a surgeon‑turned AI scientist, details how SpeedSize grew from $400K to $6M ARR by leveraging AI‑driven media compression, a usage‑based enterprise pricing model, and a partnership‑first go‑to‑market strategy with AWS and IBM. He explains the land‑and‑expand sales motion...
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Podcast•Nov 26, 2025•0 min
Bootstrapped to $82M: How Callum Mckeefery Built Reviews.io From His Kitchen Table
In this episode, bootstrapped founder Callum McKeefery details how he and his wife grew Reviews.io to $12 M ARR and sold it for $82 M without outside funding, emphasizing a SEO‑driven viral loop, high revenue per employee, and a non‑equity compensation model...
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Podcast•Nov 21, 2025•0 min
He Used AI to Generate $6m Revenue at Dreamstories by Selling Childrens Books
In this episode, Ricardo, founder of DreamStories.ai, explains how he built an AI‑driven personalized children’s‑book studio that has generated over $3 M in sales and acquired more than 100,000 paying customers using profit‑positive Facebook ads. He details his acquisition strategy—keeping customer...
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Podcast•Nov 18, 2025•0 min
Lemlist Revenue Hits $40M: CEO Charles Breaks Down $25M Claap Acquisition Deal
In this episode, Lemlist CEO Charles Tenot reveals that the company has surpassed $40 million in revenue and outlines a strategic plan to reach $100 million by 2028. He breaks down the $25 million acquisition of Claap, explaining how the deal was financed...
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