Read this for more context on our episodes

This podcast is an ongoing discussion about our startup journeys, which means if you’re a new listener, you’re entering in the middle of the story. That’s no problem! We’d recommend reading these quick facts about what we’re working on so you’ll understand what we’re talking about:

Last updated 10/9/2020

Rick Lindquist (LegUp Ventures) - @RickLindquist

  • Founded: 2019
  • Location: Salt Lake City, Utah
  • Team size: 1 employee not including Rick
  • Revenue: $2,000 MRR (monthly recurring revenue)
  • Products:
    • LegUp Health - A better way for Utahns to find, use, and manage their own health insurance plans.
    • Personal Newsletter - A weekly newsletter with new articles, book notes, and curated content in your inbox every Sunday.
  • Learn more about Rick in Episode 14 or by reading below.

Tyler King (Less Annoying CRM) - @TylerMKing

  • Founded: 2009
  • Location: St. Louis, MO
  • Team size: 19 employees including Tyler
  • Revenue: $240,000 MRR (monthly recurring revenue)
  • Product:
  • Learn more about Tyler in Episode 12 or by reading below.

Want to learn more about us? Keep reading...

What it means to “startup to last”

This podcast is about building a company to last. Not to sell. This mindset heavily influences our discussions. Knowing more about what it means to Startup to Last will help you follow our takes. For more on what it means to startup to last, check out this episode.

Our format

We try to release new episodes every other week. Most episodes follow this format*:

  1. Updates - We start with sharing updates on our businesses. We also share important personal updates when it makes sense. This can last anywhere from 15 to 30 minutes. In rare cases, our updates may take up the entire episode.
  2. Topics - Assuming updates don’t take up the full time, the remainder of the episode is dedicated to covering new topics each week. Most topics are driven by challenges Tyler and Rick are facing. But some topics are based on current events or requested by our listeners.
If you're interested in listening to some of our greatest hits, we've heard good things about these episodes:
  1. Episode #61 - Handling capacity for a seasonal business
  2. Episode #53 - Asking for too much info during signup
  3. Episode #8 - How to teach yourself to code a web-based application

* Sometimes we do special episodes with unique formats (e.g. Episode #46 on racism, Episode #18 with Ben Orenstein, and Episode #59 on no-code with Malia Jones).

More info on the hosts

Rick Lindquist is the founder of LegUp Health, a free health insurance agency that helps Utahns confidently find, manage, and use their own coverage. To learn more about Rick, check out his full story in episode 14. You can reach him on Twitter @RickLindquist. Here’s what you should know about Rick:

  • Grew up in North Carolina
  • Went to college at Duke University
  • Majored in Economics and Computer Science
  • Wrestled at Duke
  • Moved to Park City to ski bum after graduation
  • Met Tyler at a startup called Zane Benefits (which is now part of PeopleKeep) in 2007
  • Became the President of Zane Benefits after a mass layoff in 2008
  • Bootstrapped Zane Benefits to $4+ million in annual revenue in 2013/2014
  • After a regulatory threat in 2013, launched a new business called PeopleKeep
    • Raised ~$3M in venture capital to finance this
  • Wrote a book in 2014 which was published by Wiley
  • Merged Zane Benefits with PeopleKeep after confirming the legality of PeopleKeep’s approach and reaching product market fit in 2018. Milestones included:
    • $120K in monthly recurring revenue (MRR)
    • Profitable unit economics
    • 50+ user net promoter score (NPS)
    • Low churn for very small business segment
    • Numerous customer growth and product expansion opportunities
  • Was fired by the board in October 2018 when unable to align on long term compensation
  • Founded LegUp Ventures in May 2019, which owns and operates companies that empower underdogs. Current ventures include:
    • LegUp Health, Rick’s primary venture
    • RickLindquist.com, where Rick writes on various topics
    • Startup to Last, this podcast
  • LegUp Health is 100% self-funded and bootstrapped
    • Launched the company in February 2020
    • Launched the product in May 2020
    • Hit 10+ clients and ~$500 in MRR in August 2020
    • Currently focused on iterating the product and figuring out client acquisition
  • Likes:
    • Physical fitness
    • Continuous improvement
    • Sustainability (i.e. balance)
  • Dislikes:
    • Bullies
    • Victim playing
    • Intellectual laziness

Tyler King is the co-founder and CEO of Less Annoying CRM, a bootstrapped SaaS company that helps small businesses succeed. If you want to learn more about Tyler, you can check out his full story in episode 12. You can reach him on Twitter @TylerMKing. Here’s what you should know about Tyler:

  • Grew up in St. Louis, Missouri
  • Went to college at Washington University in St. Louis (“Wash U.”)
  • Majored in Computer Science
  • Became a web developer through side projects and internships
  • Played guitar in a heavy metal band called Embers Rise
  • Left his Masters program early to join a startup called Zane Benefits (which is now part of PeopleKeep) in Park City, Utah
  • Met Rick at Zane Benefits in 2007
  • Survived a lay-off with Rick in October 2008 and became head of product
  • Worked with Rick to pivot the business model to get to cash flow positive
    • Zane Benefits provided a software-enabled service to small businesses that allowed a company to reimburse its employees for individual health insurance tax-free
  • Had no interest at all in entrepreneurship prior to Zane Benefits
  • Got frustrated having the responsibility to lead Zane Benefits without the power to make key decisions (i.e. “board decisions”)
  • Founded what is now Less Annoying CRM in 2009 with his brother Bracken
  • Less Annoying CRM is a simple customer relationship (CRM) tool for small business people
  • Got the idea from working with insurance agents and Salesforce at Zane Benefits
  • Less Annoying CRM is 100% self-funded and bootstrapped
    • Launched the product at the beginning of 2010
    • At the beginning of 2011, hit 50 users / $6,000 in annual recurring revenue (ARR)
    • At the beginning of 2012, hit 500 users / $60,000 in ARR
    • As of the recording of Tyler’s episode, at 22,000 users / $2.6 million ARR growing at ~20% per year. 
  • Wants to run Less Annoying CRM for the rest of his life
  • Unique perspectives
    • Fan of bootstrapping
    • Thinks raising venture capital is limiting for a company
    • Thinks more founders should look to run companies for life versus selling
Broadcast by