Startup to Last

This week, we talk look back at 2020, look ahead to 2021, and make some predictions.

Show Notes

Looking back at 2020
Note, many of the goals mentioned here were set in our 2019 recap episode.
  • Personal accomplishments 
    • Rick 
      • 2019 Goal: Get to a point where he and his wife feel comfortable having kids - ✅ Not only are they ready, Rick's wife is pregnant 🎉
      • 2019 Goal: Increase level of play - ✅ He's been playing basketball, skiing, playing water sports, etc.
      • Had success writing his newsletter almost every week.
    • Tyler 
      • 2019 Goal: Get a dog - ✅ His name is jolo and he's an idiot.
      • 2019 Goal: Exercise three times per week - ❌ Things were looking good until covid hit.
      • Got married and bought a house.
  • Business accomplishments 
    • Rick 
      • 2019 Goal: Grow to $10k MRR - ❌ But did even better by focusing on one business and investing in the long term.
      • LegUp Health makes more money than it spends.
      • Built the LegUp Health product with no-code and low-code.
      • Shut down his old business, Group Current, while maintaining a strong relationship with his co-founder.
    • Tyler 
      • 2019 Goal: Continue product team's momentum - ✅ LACRM put out meaningful product improvements regularly throughout the year.
      • 2019 Goal: Write code once per week - ❌ Didn't even come close.
      • 2019 Goal: Average 50 paying users/month from the referral channel - ❌ Had the right input, but didn't get the results.
      • Launched a major redesign.
      • Made it through the pandemic despite a couple terrible months.
      • Raised prices.
      • Hired two new people.
  • Biggest disappointment 
    • Rick - Not spending enough time with customers, friends, and family.
    • Tyler - Had to fire an employee.
  • Biggest learning 
    • Rick - The difference between earning 10% of a business vs 100%.
    • Tyler - The role of an entrepreneur vs. the role of a CEO.
Discussing big picture goals
  • Why are we entrepreneurs? What drives us? 
    • Rick - He's good at it, he likes it. It's the best pathway to freedom.
    • Tyler - Trust, building things, creating a great place to work.
  • What do we want to accomplish over 10+ years 
    • Rick - $10mm ARR, 20% profit. Become the one-stop shop for consumers finding healthcare. Build a full benefits platform for employers.
    • Tyler - Turn the one successful product into a suite of products for small businesses. Be more than a CRM.
  • What do we our roles to be long-term? 
    • Rick - Build a management team. Stay involved in product marketing.
    • Tyler - Manage the product team and innovate on the product as an individual contributor. Be CEO, but mostly have non-product things delegated to a management team.
Expectations for 2021
  • Personal themes/goals 
    • Rick - Get sleep under control. Adjust to being a dad.
    • Tyler - Spend more time with friends and family once the pandemic is under control (knock on wood)
  • Professional themes/goals 
    • Rick 
      • Get to $10k MRR.
      • Automate/delegate so service can be scalable.
    • Tyler 
      • Get marketing to the point that it can be delegated.
      • Design the new appointment scheduler product.
  • Biggest worry 
    • Rick - Being able to scale service.
    • Tyler - Growth leveling off after the benefit of the price increase wears off.
  • What do we want to learn? 
    • Rick - Learn more coding, especially working with API data and generating dynamic emails.
    • Tyler - Re-learn how to iterate and move fast.
Predictions
  • Our predictions from last year 
    • Rick - An all-in-one solution will emerge in the no-code space ❌
    • Tyler - Startups raising money from non-VCs will become more mainstream (sort of happened, but still in progress)
  • Next year 
    • Rick - Asynchronous video will become big in professional settings.
    • Tyler - San Francisco will start a new era of opportunity for early-stage startups.

What is Startup to Last?

Two founders talk about how to build software businesses that are meant to last. Each episode includes a deep dive into a different topic related to starting, growing, and sustaining a healthy business.