Looking back at 2022 and forward to 2023

Startup to Last

Personal updates from 2022

• Tyler
  • Goals from last year
    • ✅ Plan for travel as part of relationship
    • ❌ Build more schedule flexibility
  • Other updates
    • Figured out personal finance plan with Shelly
• Rick
  • Goals from last year
    • ✅ Reprioritize daily personal health habits
    • ❓Spend more quality time with Sable (have a date most weeks) and Oliver (take on errands)
    • ❌Writing goals

Professional updates from 2022

• Tyler
  • Goals from last year
    • ❓ Spend more time working, but on my own terms
    • ❓ Make space to do more individual contributor design work
    • ❌ Release redesign of LACRM
    • ❓ Two blog post-worthy updates per quarter
    • ✅ Shift product priorities to be more focused on growth/strategy and less on low-impact customer requests.
    • ✅ Run the coding fellowship
  • Other updates
    • More of a CEO, less of a manager
    • Growth was bad, but not as bad as expected
    • Product team got more focused
• Rick
  • Goals from last year
    • ✅ 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

2023 personal themes/goals

• Tyler
  • Take more vacation and make up for it with extra work days
  • Start working towards my rich life: Renovate the house
• Rick
  • Get weight below 200lbs
  • Write a newsletter most Sundays (at least 27 Newsletters)

2023 professional themes/goals

• Tyler
  • Reap the rewards we sowed in 2022 (marketing projects and product team productivity)
  • Get back to decent growth: +$36k ARR per month
  • More of a sense of urgency on the dev team
  • Three major product wins
    • Redesign
    • Finish all "first round" growth projects (Zapier, API platform, event invites)
    • Close the gap between us as other CRMs (email logging and/or kanban view)
  • If there's a recession, minimize impact on customers and employees
• Rick
  • Retain JD for another year
  • Double the client base again (~200 clients)
  • Build v1 of LegUp Benefits and get to $1k MRR

Biggest worry

• Tyler: Product relevance - Have we lost ground in the CRM market
• Rick: Personal and family health

What do we want to learn?

• Tyler
  • How to communicate how decisions are made better
  • How to simplify policies so they are easier to understand
• Rick
  • How to build a SaaS via contractors and self-taught coding (i.e. without giving up equity)
  • Further expertise in digital advertising and data
  • Best practices for effective leadership (in the home, neighborhood, and workplace)

Predictions

• Tyler
  • Generative AI will advance, but not break through in 2023 (it will still seem more like the future than the present at the end of the year)
  • Binance and/or Tether will collapse, and Bitcoin will end the year down
  • The recession will get worse
    • S&P500 will be down over the first half of the year
    • There will be more tech layoffs in 2023 than there were in 2022
• Rick
  • Big swing back to co-location as a working requirement
  • AI gets embedded into workflows for millennials