Alex Shartsis from Skyp on Winning Outbound in the Age of AI Email

I am thrilled to have Alex Shartsis, the founder and CEO of Skyp, a bootstrapped AI email platform powering personalized outbound for sales teams at leading companies. In this episode, Alex Shartsis, founder and CEO of Skyp, shares insights on building a bootstrapped GTM software company, writing outbound that actually earns replies, and winning a crowded category against far better-funded rivals. Discover how one conference-outreach play packed an enterprise pipeline with 130 leads in a single quarter, why a $20M exit can beat a $20M raise, and what most people still get wrong about AI-generated cold email in 2026. Timestamps 00:50 What a great sales team actually looks like 02:48 Why Alex bootstrapped Skyp instead of raising VC 07:42 The payback math: when a $20M outcome beats a $20M raise 10:32 Outbound in 2026 — personalization that works vs. slop 15:05 Do follow-up emails work? (why he ignores your first one) 18:02 Email + LinkedIn + phone: the multi-channel workflow 22:42 AI coding tools for non-technical founders & GTM leaders 27:54 Pricing: why Skip refuses credit-based pricing 33:51 Winning a crowded category against better-funded rivals 37:59 Personal brand & newsletter as a GTM engine 41:39 Rapid fire: favorite business book 43:08 What he'd do differently building Skyp Alex's Links LDN/ X – https://www.linkedin.com/in/shartsis/ Website – https://skyp.ai/ My Links Podcast: https://lifeselfmastery.com/itunes Newsletter: https://partner-grow.beehiiv.com/subscribe YouTube: youtube.com/lifeselfmastery Twitter: https://twitter.com/rohitmal LinkedIn: https://www.linkedin.com/in/rohit857/ Course: https://www.udemy.com/course/outbound-sales-mastery/