Jon Khaykin

hey, i'm jk πŸ‘‹ Β· san francisco, ca

On a mission to live a fun, interesting, meaningful life, and help others do the same.

"You're under no obligation to be the same person you were five minutes ago."
β€” Alan Watts

// what i'm doing now

I'm living my mission by building software that solves my own problems (e.g. IPOs.fyi), training to become a therapist, consulting, and investing in startups improving our health and reducing toil and suffering.

// how i got here

I chased founder status. I started a healthcare technology company and shut it down due to lack of PMF. I wasted a lot of time in the β€œidea maze” trying to find a startup idea that would be successful. I then met a co-founder and started an AI company in the employee benefits space. We built a product, raised money, and got customers. I had achieved my dream of running a VC backed company but something felt wrong. On the outside things were going well but on the inside, I was the unhappiest I’d ever been and it started to affect my mental health, my marriage, my relationships, and much more. While doing cold outreach for my business, I accidentally stumbled upon a therapist that changed my life (at the time I believed therapy was BS – ironic, eh?) and it became clear to me that I was chasing the wrong things and was wrong about the ingredients of what I wanted in my life. So I decided to leave and figure out what living a meaningful life meant to me.

Before all of that, I led engineering teams at Affirm building the next generation of financial technology within the new product accelerator. We built the first version of the Affirm Card and a crypto product. Prior to that, I led the Solutions Architecture function defining and building new technology and integrations for the biggest retailers in the world. It was a blast going from 400 to 2400 employees in 3 years! Before Affirm, I spent 1.5 years at Engagio (acquired by Demandbase).

I graduated from UC Berkeley with a major in Cognitive Science (Computational Modeling and Data Science).

// my pillars of wellbeing

  1. 01Physical health: gym, dojo, and high protein vegetarian diet
  2. 02Purpose: reducing suffering
  3. 03Family: time with my wife and daughter and extended family
  4. 04Spirituality: God, meditation, calmness and awe, nature
  5. 05Social health: friends and fun
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// work with me

  • β†’ Therapy. I'm a Marriage and Family Therapist Trainee (Supervised by a LMFT, License No. 96390) completing my practicum at One Life Counseling Center. Reach out β†’

  • β†’ Consulting. I sit at a rare intersection: I've built AI products, started companies, and I'm training to become a therapist. I work with health founders on AI, product, GTM, and more. I currently have space for 2 more clients. Let's talk β†’

Warmly, jk signature Jon Khaykin