Startup to Last

In this episode, we talk about Less Annoying CRM’s producthunt launch, and a lot more.

Here's the full topic list:

• Tyler takes a look back at LACRM's growth history, and explains their new approach to growth.
• Tyler explains how the recent Product Hunt launch went.
• Rick has cleared a lot off his LegUp Health plate and is starting to focus on new types of work.
• LegUp Health had its first partner meeting.
• April was a record month for LegUp Health.
• LACRM has their designer back with more hours than ever.
• Rick is looking to target CPAs as customers.
• The LACRM coding fellows have started.
• We discuss how to deal with the low points of being an entrepreneur.

In this episode, we discuss some changes to LegUp Health, the end of Tyler's sabbatical, and more.

Topics in this episode:

• Tyler is back from his sabbatical
• LACRM is getting ready to launch a major redesign
• Rick gives updates on how the LegUp Health/Benefits plan has changed
• Because of the changes, we renegotiated Tyler's compensation and involvement in the company
• Tyler talks about the difference building a product that customers don't expect to use regularly vs and every-day productivity tool.
• Rick gives an update on working with a marketing coach
• We talk about Seeyafuture.me

Come on, you know what we're talking about. It's all anyone is talking about. Sorry, we don't make the rules.

In this episode, we talk about the very early stages of building LegUp Benefits, and a bunch of other stuff. 

Topics:

• Rick has hired a marketing coach for LegUp, and we discuss how to get the team talking to each other more instead of having everything flow through Rick.
• Tyler gives some reflections on leaving LACRM for 6 weeks, and the early days of his sabbatical.
• Tyler describes a new positioning idea at LACRM.
• We discuss the early work on LegUp Benefits including customer validation and learning a new tech stack.
• Rick gives an update on his new group insurance efforts.
• We talk about Silicon Valley Bank even though we don't have anything to say that hasn't already been said.

 In this episode, we talk about how bootstrappers can win against companies that have raised massive amounts of money.

Full topic list:

• We give an update on the compensation negotiations we discussed last episode. We've agreed on terms for Tyler to work for Rick on LegUp Benefits!
• Rick had his first annual offsite and shares a ton of great learnings.
• LACRM had a great month in February. There was absolutely nothing to learn from it.
• LACRM's major redesign is getting closer.
• Rick has streamlined bookkeeping and other financial tasks to save time.
• Tyler is thinking through when it makes sense to do custom work for a large client.
• We tackle a listener question: How do bootstrapped companies compete with funded competitors.

If you’ve been following along, you know that Tyler is about to temporarily join Rick’s startup to help build their new app. In this episode, we talk about the compensation proposal Rick just came up with. 

Full topic list:

• Rick already has a new group insurance client after deciding to give that a shot in the last episode.
• JD is visiting Rick in Utah next weekend.
• Tyler is having success with delegation, and finds himself with a lot of unstructured time on his hands...
• ...and Tyler is having to re-learn what to do with unstructured time.
• LegUp Health got hit with a bunch of spam contact forms.
• Tyler is planning the new office layout for LACRM.
• Apparently design debt is a thing.
• Tyler is having trouble getting started on the LegUp Benefits project. Side projects are hard.
• Rick brings up Youtube Premium, Quora, and NotionAI
• Big topic: We discuss the compensation proposal that Rick just sent Tyler.

 In this episode, we discuss what we do when a customer has security and compliance questions, plus, a whole lot more.

Topics in this episode:

• Tyler shares his experience at Big Snow Tiny Conf
• Tyler is getting ready for a sabbatical which means delegating a lot of work to other people
• Rick talks about gather customer profiles at LegUp Health
• Rick explains what "aged leads" are
• We discuss whether or not it makes sense for Rick to go after group health insurance clients
• Tyler talks about an LACRM company tradition
• LACRM launched their Zapier integration!
• Tyler is preparing to do more design work
• We have some rants and shoutouts
• We talk about what to do when a lead asks for security certifications and/or asks you to fill out a questionnaire 

Topics this week:

• Tyler is going to work with Rick to build the new LegUp Benefits SaaS product
• Rick has officially transitioned LegUp to 2023
• Rick talks about how Airtable Interfaces are useful
• Rick talks about an annual retreat with JD, and we discuss rituals and traditions
• Tyler is going to Big Snow Tiny Conf
• LACRM launched their new API, and are almost ready to launch Zapier integration
• We talk about the value of podcasting

Personal updates from 2022

• Tyler
  • Goals from last year
    • ✅ Plan for travel as part of relationship 
    • ❌ Build more schedule flexibility 
  • Other updates
    • Figured out personal finance plan with Shelly
• Rick
  • Goals from last year
    • ✅ Reprioritize daily personal health habits 
    • ❓Spend more quality time with Sable (have a date most weeks) and Oliver (take on errands) 
    • ❌Writing goals

Professional updates from 2022

• Tyler
  • Goals from last year
    • ❓ Spend more time working, but on my own terms 
    • ❓ Make space to do more individual contributor design work 
    • ❌ Release redesign of LACRM
    • ❓ Two blog post-worthy updates per quarter
    • ✅ Shift product priorities to be more focused on growth/strategy and less on low-impact customer requests.
    • ✅ Run the coding fellowship
  • Other updates
    • More of a CEO, less of a manager
    • Growth was bad, but not as bad as expected
    • Product team got more focused
• Rick
  • Goals from last year
    • ✅ 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  

2023 personal themes/goals

• Tyler
  •  Take more vacation and make up for it with extra work days
  •  Start working towards my rich life: Renovate the house
• Rick
  • Get weight below 200lbs 
  • Write a newsletter most Sundays (at least 27 Newsletters)

2023 professional themes/goals

• Tyler
  • Reap the rewards we sowed in 2022 (marketing projects and product team productivity)
  • Get back to decent growth: +$36k ARR per month
  • More of a sense of urgency on the dev team
  • Three major product wins
    • Redesign
    • Finish all "first round" growth projects (Zapier, API platform, event invites)
    • Close the gap between us as other CRMs (email logging and/or kanban view)
  • If there's a recession, minimize impact on customers and employees
• Rick
  • Retain JD for another year
  • Double the client base again (~200 clients)
  • Build v1 of LegUp Benefits and get to $1k MRR

Biggest worry

• Tyler: Product relevance - Have we lost ground in the CRM market
• Rick: Personal and family health

What do we want to learn?

• Tyler
  • How to communicate how decisions are made better
  • How to simplify policies so they are easier to understand
• Rick
  • How to build a SaaS via contractors and self-taught coding (i.e. without giving up equity)
  • Further expertise in digital advertising and data
  • Best practices for effective leadership (in the home, neighborhood, and workplace)

Predictions

• Tyler
  • Generative AI will advance, but not break through in 2023 (it will still seem more like the future than the present at the end of the year)
  • Binance and/or Tether will collapse, and Bitcoin will end the year down
  • The recession will get worse
    • S&P500 will be down over the first half of the year
    • There will be more tech layoffs in 2023 than there were in 2022
• Rick
  •  Big swing back to co-location as a working requirement 
  •  AI gets embedded into workflows for millennials 

Topics in this episode:

•  LACRM is having a good December
• Rick is feeling lots of momentum
• Rick gives an update on LegUp Health's growth
• Rick is reading the Warren Buffet bio: The Snowball
• Tyler explains LACRM's new approach to bug triage
• Rick is thinking about how hard to push for in-person
• Tyler describes a new shorthand: Following daylight
• Rick realizes he's learning a lot about digital marketing
• We discuss how it's good for businesses to be boring and complex
• Ricks suggests having "certifications" for new hires
• We discuss Webflow Logic
• Rick is going on a date!
• Tyler is trying to decide how to prioritize big bets vs. small bets at LACRM.