Startup to Last

Topics discussed:Indie.vc is shutting downRick gives a revenue and churn update.Rick is preparing for the birth of his first child, but has one more big project to finish first.Tyler recaps the first week of results after launching Less Annoying Business last week.We discuss whether it makes sense to build an audience.Tyler is trying to get help with Elasticsearch from his online community.We discuss the long, slow SaaS ramp of death.

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" programRick 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 healthcareRick'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 2020Note, 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 goalsWhy 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 2021Personal 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.PredictionsOur 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.