In this episode, we sit down with David, CEO of Whippy.ai, to explore how his bootstrapped AI startup scaled to $5M+ ARR by solving real-world automation challenges rather than chasing hype. David shares his journey from winning a World Series of Poker bracelet to founding multiple startups, culminating in Whippy—a platform that blends voice, SMS, and email automation with functional AI agents. We dive into what customers actually resonate with in AI sales pitches (hint: it's not fake human-sounding cold calls) and why building around tangible business problems—like automating the bottom 50% of recruiter tasks—has been key to Whippy's product-market fit.

We also get tactical for sales reps and founders. David reveals how he evaluates SDR talent (spoiler: experience matters less than hustle), why $99 AI tools often fall short without adoption support, and how to build AI products that drive ROI rather than just demos. Whether you're trying to hire top sales talent, scale an AI-driven product, or break into the tech industry, this episode is packed with playbooks on AI sales messaging, founder-led GTM strategy, and building sustainable startups without VC pressure.