Startup to Last

Topics this week:

• Tyler is considering going to Founder Summit in Ashville this fall.
• LegUp Health signed a partnership deal with Pando Labs.
• LACRM is on a hiring spree.
• LACRM has a new thriving wage.
• We discuss whether video testimonials are a good idea.
• Tyler heard a podcast which made fun of LACRM's design, and this resulted in him getting some design coaching.
• We discuss how Rick can structure a partnership agreement with his first hire.

This is our annual retro/goal-setting episode. Here's what we cover:

Personal updates from 2021

• Tyler
  • Goal from last year: ✅Spend more time with family and friends once vaccinated
  • Other updates
    • Started exercising
    • Froze embryos
• Rick
  • Goals from last year
    • ✅ Get sleep under control
    • ✅ Adjust to being a dad
  • Other updates
    • Wasn't good about exercising
    • Has only been on one date with Sable

Professional updates from 2021

• Tyler
  • Goals from last year
    • ✅ Get marketing to a point where if can be delegated
    • ❓ Design a new appointment scheduler product
    • ✅ Biggest worry: Growth leveling off
    • ❓ Want to learn: Re-learn how to iterate and move fast
  • Biggest disappointment: Losing a developer right when the product team was building momentum
  • Biggest learning: Wants to be a product designer
  • Other updates:
    • Fewer management responsibilities
    • Signed biggest client to-date
    • Full-funded the treasury
• Rick
  • Goals from last year
    • ❌ Get to $10k MRR. 
    • ✅ Automate/delegate so service can be scalable. 
    • ✅ Biggest worry: Being able to scale service. 
    • ✅ Want to learn: Learn more coding, especially working with API data and generating dynamic emails.
  • Biggest disappointment:  Not being able to work on LegUp Health full time
  • Biggest learning:  Sharing the journey at LegUp Health is better than going solo 
  • Other updates:
    •  Tried bringing on another friend as a Marketing contractor, but he decided to take a full-time job before he ramped up 

2022 Personal themes/goals

• Tyler
  • Plan for travel as part of relationship
  • Build more schedule flexibility so things can be done without needing willpower (e.g. exercise mid-day)
• Rick
  • Reprioritize daily personal health habits (write/exercise before family wakes up, daily calorie tracking)
  • Spend more quality time with Sable (have a date most weeks) and Oliver (take on errands)

2022 Professional themes/goals

• Tyler
  • Theme: Spend more time working, but on my own terms
  • Make space to do more individual contributor design work
  • Other things
    • Release 3.9 design
    • Two blog post-worthy releases per quarter
    • By end of year, have an equal balance of tech debt, core CRM, strategy, and product-led growth work on the dev team
    • Run the coding fellowship
• Rick
  • Support the growth of LeUp Health
    • 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 
    • Prioritize both performance and people
    • Be a team player
    • Deliver on my responsibilities

Biggest worry

• Tyler: Growth slowed in 2021. Will it come back?
• Rick: Retaining JD for the long term

What do we want to learn?

• Tyler: More professional visual design
• Rick: First principles of leading others (e.g. influence, motivation, habits, trust, negotiation, communication, and decision-making)

Predictions

• Last year
  • Tyler: ❌ San Francisco will become a good place for early-stage startups again
  • Rick: ❓ Asynchronous video will become big in professional settings
• Next year
  • Tyler: The world will be less interested in speculative bubbles (NFTs, meme stocks, etc.)
  • Rick: VR headset use is going to become as common as playing a Wii

This is our last episode. Thanks to everyone who has listened and supported us over the last couple years. We're going to miss you 😢

Topics in this episode:

• Rick accepted a new job. What does that mean for LegUp Health?
• Rick finished migrating his help site to Webflow.
• Rick notified his free users that the free service is shutting down.
• Tyler talks about compounding and what it means for thinking about the future.
• We discuss how it might be harder to start a company these days because there are so many success stories that are hard to live up to.
• We discuss Datafetcher.com as a nice no-code tool.
• We discuss the build vs. buy tradeoffs.

Topics this week:

• Rick is canceling his CRM subscription.
• Tyler is considering where his newsletter fits into his overall plan.
• Based on our conversation last week, Rick has new clarity around the future of LegUp Health.
• Tyler explains how LACRM came up with their long-term product roadmap.
• Rick is going through continuing education.
• We discuss some touchy feely things related to the passage of time.

Topics from this episode:

• Less Annoying CRM is back to remote-first because of the new wave of the virus.
• LACRM had a new developer start this week.
• Rick is thinking about how to simplify his business. Specifically, what can he cut?
• We discuss what it means to be a calm company. Or is that even the goal?

Topics from this episode:

• Tyler hit 2,000 Twitter followers, and we discuss how Twitter is a hits-based business which doesn't suit Tyler's strengths.
• Rick gives an update on his personal website and newsletter optimization efforts.
• Rick reached the first page on an important search term.
• Less Annoying CRM is tweaking the format of help articles to appeal more the the easily distractible internet user.
• Rick has finished his javascript course.
• Tyler discusses the LACRM product roadmap.

Topics this week:

• Tyler had fun with a once-per-year football bet, and Rick had to put in a full day of dad duty.
• Tyler is considering taking the ShiftNudge design course to get better at design. He also purchased a license to Tailwind UI so he can copy from better designers.
• LACRM is tweaking it's policy that everyone at the company must do an hour or support each week.
• Rick reflects on the value he gets from both writing and reading personal newsletters.
• LACRM is tweaking it's policy around employee conversation, partially based on a conversation we had on this podcast a couple weeks ago.
• Tyler's Mixergy interview is live.
• Now that Rick has a sense of what is and isn't working at his business, he wants to simplify which will mean cutting some current complexity away.

Topics this week:

• Rick launched LegUpBenefits.com.
• We discuss Rick's new no-code tool: Outseta.
• Less Annoying CRM has a new developer starting next month.
• Tyler has refined his approach to writing internal documentation, and Rick makes a fantastic analogy.
• Tyler's co-founder/brother will be in town next week.
• Rick wants to keep practicing coding so his skills don't deteriorate.
• Rick is taking a break from podcasts.
• Tyler wants Rick's help to teach the coding fellows about no-code use cases.
• We discuss Rick's notes on Anything You Want which leads to a conversation about whether startup utopias are real.

Topics this week:

• Rick took some time off, but is wondering if he earned it.
• Tyler wrote five blog posts in one day, and wonders if this should be the new approach to blogging.
• Rick decided to wait for Memberstack updates before taking on a coding project he was planning.
• Rick is using Outseta for his next technical project to diversify away from Memberstack. He plans to have the done in the next week.
• Rick is still waiting to decide how to handle the API vendor that closed down his account.
• Tyler is diving into design and is interested in improving his skills.
• Tyler has found a couple promising use cases for his new iPad which he mostly hates.
• The big topic for this week: What are ways a company can fairly share profits with employees? Specifically, is it better to pay current employees more, or hire more people to spread the wealth around.

Topics in this episode:

• Tyler was interviewed to be on Mixergy, but didn't think he did a great job.
• Rick is adjusting his routine now that he has a kid to take care of.
• Rick enrolled in a new javascript course to hone his skills.
• Tyler's previous positive results converting website visitors to his newsletter have turned to failure. No one is signing up.
• Tyler attended Less Annoying CRM's first leadership team meeting.
• Tyler had his first person finish building a website based on his online course.
• Tyler (geez, enough with updates from Tyler, right?) is thinking through putting a limitation on LACRM.
• Tyler (seriously, stop) took a day to help his dad with a new project.
• Rick had a big coding win and finished two projects...
• ...just in time for one of his API vendors to close down his account, so the projects don't really work anymore. We discuss how Rick should respond.