UP Case Study #3


Closed $250M+ deal and achieved financial independence.


  1. Create or help grow an economically valuable organization that fully internalizes costs
  2. Use resources created (wealth, knowledge, skills, etc.) to help life
    1. Donate excess wealth
    2. Accelerate sustainable energy implementation
    3. Spread effective altruism
  3. Maintain high level of health, fitness, and mobility for entire life
    1. Maintain a high energy level
    2. Maintain a low body fat (between 4% and 10%)
    3. Maintain lifelong ability to participate in sports (including, for example, riding mountain bikes)
  4. Attempt to live a long time within reason, given tradeoffs and probabilities
    1. Ideally achieve longevity escape velocity
  5. Optimize for intelligence, knowledge, agency and truth-seeking
  6. Make enough money to live comfortably
    1. Achieve financial freedom
    2. Take quarterly trips
    3. Own a cabin in woods
    4. Have $2.25-3.75M in net assets
    5. Take risks and accomplish things rather than just having a high salary
  7. Have meaningful relationships
    1. Spouse
      1. Improving her capabilities
      2. Making her happy
      3. Increasing her options for career success
    2. Friends
      1. Maintain long-term friendships with people where we level each other up
    3. Family
      1. See Mom at least once per quarter (on average)
      2. Have good relationship with Sister
  8. Have significant control over time (both internal and external agency)


  1. Type: Individual Annual UP -> Individual Variable UP
  2. Length: Ongoing, 3 years and 9 months as of this update
  3. Support:
    1. 42 UP Coach Calls + 61 UP Coach Tasks + 5 UP Assistant Tasks + 0 Other Personal Team Tasks = 108 Tasks
    2. 81 UP Coach Hours + 5 UP Assistant Hours + 0 Other Personal Team Hours = 86 Hours


This well-resourced, rational financial professional chose to do an UP to make life as awesome as possible. He was smart, married, and a workaholic. He was living a good yet extremely stressed life due to work commitments and emotional challenges. His UP on the whole was very high-level with minimal strategic and tactical support throughout.


The client’s UP included specialized coaching from a carefully selected coach, access to a team of behavior change experts and assistants, and use of 50+ digital behavior change tools. He set a number of short-term and long-term goals. His team included very ad hoc use of specialists including psychotherapists, doctors, and personal trainers.


Protocol Completion


Top 3 Successes

  1. Made several million dollars
    1. Received golden parachute payout worth $2.5M
    2. Received $3.5M in cash and expected $8M+ in equity from a $250M deal he arranged in under 500 hours
    3. Secured equity in a number of startups he helped build worth millions in expectation
  2. Built life and project management systems that helped him reclaim hundreds of hours of otherwise lost time
  3. Became extremely fit
    1. Originally lost 20 pounds of fat while gaining 10 pounds of muscle, gained it all back during COVID, and then lost nearly all of it again

Top 3 Failures

  1. Did not yet fully alleviate his perfectionism, imposter syndrome, self-doubt, and anxiety
    1. Did make substantial progress
  2. Did not yet fully determine what he wanted to do with the rest of his life
    1. Did set and pursue a short-term path and made moderate progress on determining long-term path
  3. Did not invest as much time as desired into his general self-development (including his UP)
    1. Did make moderate progress


  • It was a good but limited UP that was enjoyable for both the client and UP Coach and was relatively easy to design and execute
  • The client made substantial progress on his goals that exceeded his expectations
  • The client estimated a 5% impact on his overall goal attainment over the UP (30% over the first more involved year)
  • The UP Coach estimated a 5% impact on the client’s overall goal attainment over the UP (15% over the first more involved year) 

Client Summary

“UP significantly improved me and my spouse’s life and project management skills, allowing us to both increase our effectiveness substantially. The UP Coach was very helpful in the short and medium term goal setting process, which I had never done before and generally have an aversion to. I would highly recommend UP to anyone who is interested in improving their effectiveness.”