Business Bootstrap with Tyler King

How to bootstrap a small business with Tyler King, co-founder of Less Annoying CRM. Tyler also shares his interesting journey to entrepreneurship, and insights into how he bootstrapped the launch and growth of his software business.

Tyler King - EntrepreneurTyler King is the co-founder and CEO of Less Annoying CRM, a bootstrapped SaaS (Software as a Service) company that helps small businesses succeed. He majored in Computer Science at university, had successful career in IT, and a side gig as a guitar player on a heavy metal band, but had not aspirations then of starting his own business back then. But the impact of surviving a layoff in 2008 got him thinking about starting his own business. In 2009, he founded what is now Less Annoying CRM with his brother Bracken King.

Tyler is also the co-host of the Startup to Last podcast.

Tyler lives in St Louis, Missouri.


Business Bootstrap with Tyler King: 

  • Please share the brief story of what led you to launching Less Annoying CRM?
    • Defining moment – layoffs in 2008 at company he worked for at the time.
  • You launched in 2009, then transitioned to full-time in the business in 2013. What were some of the challenges you faced with building this business (consulting part-time) on the side and how did you overcome them?
  • Why did you move to St. Louis? 
  • Why did you win the Arch Grant (Less Annoying CRM won the Arch Grants Global Startup Competition, which supports innovative and scalable businesses based in St. Louis.)
  • Why were you awarded the best place to work in St. Louis for young professionals?
  • Did you purposely decide to bootstrap your small business and be 100% self-funded or was it out of necessity?
  • Why do you believe bootstrapping and self-funding is a better approach than seeking loans or investors?
  • How does bootstrapping alter the way you launch and grow a small business? What are the disadvantages and advantages?
  • Why do you believe venture capital can prove limiting?
  • How did you fund the initial development?
  • Did you take an MVP approach to developing the product?
  • Hired an employee first, instead of paying yourself to join full time. (Part of this decision influenced by your personal life situation at the time.)
  • Why do you think more founders should look to run companies for life versus selling? Why do you want to run Less Annoying CRM for the rest of your life? Do you nonetheless develop the business such that it could operate without you?
  • Why the focus on customer service?
  • Not passionate about CRM, but passionate about the business. Please explain.
  • Why did you decide to partner for this business? How do you make your partnership with Bracken King (his brother) work? Are you the majority partner?

Episode Host: Henry Lopez is a serial entrepreneur, small business coach, and the host of this episode of The How of Business podcast show – dedicated to helping you start, run and grow your small business.


Books mentioned in this episode:
[We receive commissions for purchases made through these links (more info)].

Other Podcast Episodes:

You can find other episodes of The How of Business podcast, the best small business podcast, on our Archives page.


This episode of The How of Business podcast is sponsored by LinkedIn Jobs. Get your first posting FREE!

LinkedIn Jobs

We have received compensation from this sponsor partner. We only accept sponsorships from companies who we believe provide products and services that are valuable for small business owners.

Leave a Reply

Your email address will not be published. Required fields are marked *