Rebirth / Welcoming 2022

The rumors were true. Startup to Last is back, and we're starting out with a recap of 2021 and a look forward to 2022.

This is our annual retro/goal-setting episode. Here's what we cover:

Personal updates from 2021
  • Tyler
    • Goal from last year: ✅Spend more time with family and friends once vaccinated
    • Other updates
      • Started exercising
      • Froze embryos
  • Rick
    • Goals from last year
      • ✅ Get sleep under control
      • ✅ Adjust to being a dad
    • Other updates
      • Wasn't good about exercising
      • Has only been on one date with Sable
Professional updates from 2021
  • Tyler
    • Goals from last year
      • ✅ Get marketing to a point where if can be delegated
      • ❓ Design a new appointment scheduler product
      • ✅ Biggest worry: Growth leveling off
      • ❓ Want to learn: Re-learn how to iterate and move fast
    • Biggest disappointment: Losing a developer right when the product team was building momentum
    • Biggest learning: Wants to be a product designer
    • Other updates:
      • Fewer management responsibilities
      • Signed biggest client to-date
      • Full-funded the treasury
  • Rick
    • Goals from last year
      • ❌ Get to $10k MRR. 
      • ✅ Automate/delegate so service can be scalable. 
      • ✅ Biggest worry: Being able to scale service. 
      • ✅ Want to learn: Learn more coding, especially working with API data and generating dynamic emails.
    • Biggest disappointment:  Not being able to work on LegUp Health full time
    • Biggest learning:  Sharing the journey at LegUp Health is better than going solo 
    • Other updates:
      •  Tried bringing on another friend as a Marketing contractor, but he decided to take a full-time job before he ramped up 
2022 Personal themes/goals
  • Tyler
    • Plan for travel as part of relationship
    • Build more schedule flexibility so things can be done without needing willpower (e.g. exercise mid-day)
  • Rick
    • Reprioritize daily personal health habits (write/exercise before family wakes up, daily calorie tracking)
    • Spend more quality time with Sable (have a date most weeks) and Oliver (take on errands)
2022 Professional themes/goals
  • Tyler
    • Theme: Spend more time working, but on my own terms
    • Make space to do more individual contributor design work
    • Other things
      • Release 3.9 design
      • Two blog post-worthy releases per quarter
      • By end of year, have an equal balance of tech debt, core CRM, strategy, and product-led growth work on the dev team
      • Run the coding fellowship
  • Rick
    • Support the growth of LeUp Health
      • Structure a partnership and financial plan that enables JD to go full-time
      • Grow the business to 400 clients
      • Fully automate the new user onboarding experience
    • Help scale Windfall the right way 
      • Prioritize both performance and people
      • Be a team player
      • Deliver on my responsibilities
Biggest worry
  • Tyler: Growth slowed in 2021. Will it come back?
  • Rick: Retaining JD for the long term
What do we want to learn?
  • Tyler: More professional visual design
  • Rick: First principles of leading others (e.g. influence, motivation, habits, trust, negotiation, communication, and decision-making)
Predictions
  • Last year
    • Tyler: ❌ San Francisco will become a good place for early-stage startups again
    • Rick: ❓ Asynchronous video will become big in professional settings
  • Next year
    • Tyler: The world will be less interested in speculative bubbles (NFTs, meme stocks, etc.)
    • Rick: VR headset use is going to become as common as playing a Wii
Rebirth / Welcoming 2022
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