EPISODE 71

Jess Chan built Longplay from an email and SMS agency into a strategic growth partner that has helped more than a hundred e-commerce brands generate hundreds of millions in revenue, and then she handed over the CEO title. In this episode she explains why, and makes the case that the hardest decisions in business are the ones nobody claps for. She talks about letting lucrative client relationships drift on purpose, taking pay cuts, and flatlining revenue for two years to fix the foundations, because a hockey stick for one year often means out of business in three. She breaks down her diagnostic approach to lifecycle marketing and why most people are solving the wrong problem extremely fast and extremely well, describes what she learned building a seven figure agency during the least profitable stretch of her business, and shares the moment she realized a company is like a kid who eventually has to stand on its own. Kevin and Jason open with Kevin's first startup, an embroidery business run out of a one bedroom apartment near UCLA, and the navel gazing loop every early founder falls into. Jess also gets into why she thinks she is better off than Elon Musk, why hurt people hurt people applies to founders more than anyone, the real trade-offs between agency and SaaS after building both, and how she uses AI to buy back space instead of running yesterday's playbook faster.

CHAPTERS

00:00 – Cold open: the founders whose companies become their jobs

01:05 – Henriksen Embroidery, LLC and the navel gazing trap

04:46 – What playing the long game actually means

06:26 – Turning down money on purpose

07:54 – Handing over the CEO title

10:52 – Why email was never the real problem

12:55 – Most people are solving the wrong problem

14:34 – The seven figure agency that wasn't profitable

17:04 – Success, balance, and why Elon sounds miserable

18:35 – Hurt people, hurt people, and that includes founders

20:15 – Agency vs SaaS: choose your hard

23:03 – What AI is great at and what still needs humans

25:37 – Using AI to buy back space

27:46 – The Founder Mode Top Five

LINKS

Connect with Jess Chan

Longplay • LinkedIn • X/Twitter

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Connect with Kevin

LinkedIn • X/Twitter

Connect with Jason

LinkedIn • X/Twitter