Topics we covered today:

• Rick finished his goal for February of automating the monthly emails at Legup Health.
• Tyler gives an update on his new small business advice website. How do you like that link building I just did?
• Tyler remembers how fast a project can move when you don't have legacy code slowing you down.
• We discuss a variety of tools used to build a content site, especially Webflow and ConvertKit.
• Tyler used Fiverr for the first time to hire a designer.
• We discuss multitasking for motivation.
• We both prefer creating content from our own personal voice rather than on behalf of the company.
• We brainstorm what's next for Less Annoying Business/

Topics discussed this week:

• Rick is learning more powerful no-code tricks with Zapier, and advancing his PHP knowledge.
• We discuss the best way to learn how to write secure code.
• Tyler is wrapping up a big project which involves setting deadlines. We discuss healthy vs. unhealthy deadlines.
• Tyler is brainstorming content marketing approaches which is tough because he's not an expert on the topics his customers are most interested in.
• We discuss Rick's learnings from Peter Drucker.
• We talk about the idea of running an online competition

More topics:

• We discuss the state of independent SaaS and what it means to have a very low payback period.
• Rick has installed a development environment and is learning to code again.
• Tyler is almost done getting ready to switch the LACRM marketing site to Webflow.
• Tyler is considering trying out Mixpanel.
• Salesforce is going more remote. What does that mean for San Francisco.
• We discuss Tyler's tweet thread about his internal dashboards.
• We talk about the Trends.vc report on competitor risk.

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.