Startup to Last

Other topics this week:

• Rick officially launched a "give back" program
• Rick decided not to post internship openings until post-parental leave.
• Rick wants to start a group focused on reaching local consumers.
• Tyler is planning an at-home retreat.
• Morale is a bit low as covid drags on.
• We discuss a specific UI decision LACRM is facing.
• We discuss aligning what you want to have happen with what will actually happen.

Other topics this week:

• How Robinhood's recent controversy applies to Rick's business model.
• Rick received his first cancelation.
• Twitter acquired Revue.
• Rick is working on a low-code solution to an automation issue.
• Tyler is close to closing a deal with an enterprise client.
• We discuss how to handle security audits (e.g. SOC 2 compliance) with enterprise customers.

Other topics this week:

• Less Annoying CRM hit $3 million ARR, and the tweet about it got a lot of engagement.
• Rick paid out referral rewards to his clients.
• Rick explains his buyer journey exercise.
• Rick reflects on the value of customer appreciation.
• Tyler has been a guest on several other podcasts.
• We discuss how to react when a competitor launches.
• We discuss the idea of building buffer into everything we do, and how it relates to the startup to last philosophy.

Other topics this week:

• Tyler reviews what he learned from last week's DDoS attack.
• Rick has planned out the year and feels good about his ability to get it done.
• Rick is allocating 50% of his time to promotion and 50% to automating his product.
• Tyler is about to start teaching a design course.
• LACRM is close to finishing a migration to Webflow.
• We discuss Clubhouse.
• Tyler is getting a Peloton.
• Rick is experiencing anti-depressant withdrawal syndrome.

Other topics in this episode:

• Trump and his group of domestic terrorists are trying to overthrow the government and it sucks.
• What a Democrat-controlled government means for healthcare
• Rick's business is extremely seasonal.
• We give financial updates from 2020.
• Rick is working on some tooling changes: Twilio, Front, and knowledge bases.
• Don't be envious of other people.

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.

Other topics:

• Tyler realized he might have more revenue growth next year than he originally thought.
• Rick is learning that things don't die down immediately after open enrollment, and that's making it hard to do end-of-year planning.
• Tyler has been thinking about what the approach might be when LACRM re-opens the office.
• Rick is meeting his intern for the first time in-person.
• Rick switched to Notion and is loving it.
• Tyler has a marketing approach that he wants feedback on.
• We discuss whether companies should donate money to charities.

Other topics from this episode:

• Rick is finished with open enrollment and walks through some metrics.
• Rick is expecting his first churn from customers who signed up earlier this year.
• Rick realizes that word of mouth happens at specific moments in time, such as when someone leaves their job, gets married, or has some other life event.
• Tyler is learning more about his strengths and weaknesses.
• Tyler is overwhelmed with interviews.
• Tyler is preparing a presentation on recruiting and diversity.

I would like to apologize for my lack of creativity in the sentence structure above. It's the middle of December and it's pitch black outside even though it's not even 6pm, so it just seems like writing up interesting show notes is not a great use of my time when I could instead be eating fast food and watching Netflix. Thanks for understanding.

Other topics we covered this week:

• Advent of code
• The Less Annoying CRM design fellowship is finalized.
• Rick has a few different channels that are showing traction including Instagram DMs and getting referrals from other insurance agents.

Here are some of the other topics we discuss:

• Slack was acquired by Salesforce for a bunch of money. Like, a whole lot.
• Stripe launched a new "Treasury" product.
• Tyler finished his end-of-year planning.
• Rick has been bouncing between projects.
• Google Search Console has been broken for Rick.
• My first million is a good podcast.