Startup Spotlight #111: Sail
Sail teaches emotional intelligence to transform men into world-class leaders.
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I got the chance to speak with Johnny Chen, founder and CEO of Sail, about what he’s working on at his startup and any advice he has for emerging entrepreneurs.
Sail teaches emotional intelligence to transform men into world-class leaders. They offer immersive programs that combine expert coaching, cohort-based learning, and live practice to help men level up as leaders.
Chen is the founder of Sail, an education startup that teaches emotional intelligence to transform men into world-class leaders. As a growth & product leader for the last 7 years, he's had the honor of working with brands like Hims & Hers, Ten Percent Happier, Simple Habit, Universe, Life360, and more. Previously, Chen ran product & growth at Ever (founded out of Atomic) and Scopely. He solo traveled the world for an entire year in 2019 while advising startups.
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Startup Spotlight: Sail
Problem: Emotional intelligence is the #1 determinant of success in leadership roles, yet men are 86% less likely to show empathy with others. Existing solutions are either too expensive (MBA schools, corporate training seminars) or have low retention and engagement rates (MOOCs, self-guided videos).
Market: The global MOOC market (massive open online course) is $8B, growing at a CAGR of 40%. Sail's cohort-based course is leading the next wave of online education.
Solution: Sail teaches emotional intelligence to transform men into world-class leaders. We offer immersive programs that combine expert coaching, cohort-based learning, and live practice to help men level up as leaders.
Team: Johnny Chen (CEO) is a product & growth leader who has worked with Hims, Atomic, Scopely, Ten Percent Happier, Life360, and more. Matthew Kochakian (CTO) is a full-stack engineer and designer who founded two mental health startups.
Recent Success:
Chen: We're incredibly fast at adapting quickly based on learnings from our experiments. We're building a new cohort-based model in the online education space, so there's a steep learning curve. Every experiment builds on top of the learnings from the previous experiment - we've tested program duration, cohort sizes, live vs self-guided learning, subscription vs upfront tuition models, and more. The results of our experimentation are an NPS of +76 and a 4.7 out of 5 stars rating on our programs.
Recent Struggle:
Chen: Founder impostor syndrome. The reality is that >75% of founders feel impostor syndrome on a regular basis, but because we're conditioned to think that founders have it all figured out, it's challenging for us to show vulnerability and admit we don't know it all. I felt this in the early days of the company when we were raising our first round when it seemed that everyone around me was raising successfully. To address this, I built a network of other early-stage founders to hear how they manage their impostor syndrome.
One of our company values is vulnerability, so it's important that I embody the value and show vulnerability myself by sharing my story with impostor syndrome.
Founder Advice:
Chen: Surround yourself with highly talented advisors, founders, and friends. My favorite aspect of the startup community is that almost everyone is friendly and wants to help. Don't be afraid to reach out to founders at competitor companies and ask to mutually share learnings. Set up recurring calls with founder friends who can keep you accountable (and sane) when the times get tough. Every founder goes through a similar set of challenges, and it's important to learn from others who have walked your path.
Three Cool Founders You Should Know About:
Chen: Here are three founders you should check out next!
Brian Martinez, Founder of Studio: Studio is a membership community designed to help independent creatives thrive.
James Li, Founder of Mighty Health: Mighty Health offers personal training and nutrition coaching for people over 50.
Teri Yu, Founder of Vibely: Vibely is a platform for positive communities to accomplish their dreams together.
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