Startup to Last

Looking back at 2022 and forward to 2023

Dec 31, 2022

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I'm Investing in My Personal Health

Sleep Medication

I'm Not Going to Set That Goal This Year

My Traffic Growth Is Up 33% Year Over Year

I'm a Cisco Tyler or Is That You?

I Will Teach You to Be Rich Podcast

How Index Funds Work - Is That Really the Problem?

Windfall CEO Award - I'm the Suck Up, but I've Done That

I'm Not Yelling, It's Just Treating People as Objects and They Know It

The Leadership and Self Deception Book Is the Answer

The Key Goals for Leg of Health

Is 2023 Going to Be More Execution Than the 100th Client?

Taking More Naps - That's the Key in KPI

Should I Make Up Deep Work to Do?

Is Your Passion for Designing the Right Thing?

Are You Going to Continue to Do the Coding Fellowship?

Are You Good at It?

RIBMAP - Growth Is Bad, but Not as Bad as You Expected

Do You Have Personal Goals?

Losing Weight, Significant Weight Is Very Different Than Being Healthy

We Need to Start Playing Video Games Together

Is There a Recession?

Leg Up Health Is a Masterclass in How You Cycles for Calm Company

01:01:23 • 2min

What Are You Doing Right Now?

01:03:09 • 4min

My Biggest Concern Is Personal and Family Health

01:06:51 • 3min

Is Machine Learning a Good Way to Build a CRM?

01:09:22 • 2min

01:11:37 • 2min

What Do I Want to Learn?

01:13:24 • 3min

Repetition Is a Big Thing

01:15:55 • 3min

Is There a Better Way to Communicate?

01:18:55 • 2min

Building SaaS via Contractors and Self-Taught Coding Without Giving Up Equity

01:20:35 • 2min

How Do You Know if You Learned This Third One?

01:22:33 • 2min

The Most Valuable Predictions for Next Year

01:24:11 • 2min

Do You Think Co Location Is a Good Thing?

01:25:53 • 2min

Is There a Future With AI?

01:28:19 • 2min

Do You Think AI Is a Speculative Bubble?

01:30:08 • 3min

AI Is Already Changing Meaning

01:33:36 • 2min

Is There a Future for Crypto?

01:35:08 • 3min

Is There a Recession in Cryptocurrency?

01:38:34 • 2min

I'm Out of the Housing Market Right Now

01:40:05 • 2min

The Best Hasn't Come

01:41:53 • 2min

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