Previous guests include Guy Kawasaki, Brad Feld, James Clear, Shu Nyatta, Ida Tin, Elizabeth Yin, Polina Pompliano, Evgenia Plotnikova, Anna Khan, Minnie Ingersoll, Sridhar Ramaswamy, Mac Conwell, Danielle Strachman, Jake Gibson, Wes Kao, Brian Requarth, Vivek Sodera, Eric Siu, Amit Garg, Nischal Shetty, Pranav Pai, Nir Eyal, Paul Shapiro, Nick Huber, Rob Walling, Andrew Dsouza, Fabrice Grinda, and 300+ incredible guests.
Life Self Mastery Podcast is an interview based show where I interview online entrepreneurs who started their businesses and scaled up their businesses to improve their lifestyles.
Previous guests include Guy Kawasaki, Brad Feld, James Clear, Shu Nyatta, Ida Tin, Elizabeth Yin, Polina Pompliano, Evgenia Plotnikova, Anna Khan, Minnie Ingersoll, Sridhar Ramaswamy, Mac Conwell, Danielle Strachman, Jake Gibson, Wes Kao, Brian Requarth, Vivek Sodera, Eric Siu, Amit Garg, Nischal Shetty, Pranav Pai, Nir Eyal, Paul Shapiro, Nick Huber, Rob Walling, Andrew Dsouza, Fabrice Grinda, and 300+ incredible guests.
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/
