Playing the Long Game

Bootstrapped Web
Playing the Long Game

We kick off our new format with Ian Landsman. Ian is the founder of Userscape and Helpspot. He has been working in the bootstrapped world since 2004. On today’s episode we discuss what it means to “play the long game.”

We share our plans for Carthook and Audience Ops. Ian offers his personal view on the long game and what it means to him. We discuss all the aspects of making decisions for the long term in business.

The topics we covered today are below:

  • How to find “long game” ideas
  • How money can force a commitment
  • How to hire the right people
  • Brian’s long term plan for Audience Ops
  • Brian on Zero to Scale
  • What the term “scaling” means
  • Selling a one time product vs. selling a recurring service
  • Jordan’s long term plan for Carthook
  • Venture capital vs. bootstrapping
  • JD Graffam’s business approach
  • The “long game” from an investment perspective

Resources Mentioned Today:

Ian’s Twitter


Bootstrapped FM


Audience Ops

JD Graffam

As always, thanks for tuning in. Head here to leave a  review in iTunes.

[78] Changing the Course of Our Businesses

Bootstrapped Web
[78] Changing the Course of Our Businesses

Welcome to Episode 78 of Bootstrapped Web.  Today we are both very excited to bring some major updates in our businesses.  It’s very fortunate that we both are finally able to discuss these topics in detail, as both have to come close in the last couple of weeks.

Both of these announcements break the typical mold of what we have historically considered to be a “Bootstrapped” business.  In this way, they are going to change the trajectory of not just their respective businesses, but also of the entrepreneurial journey that Jordan and Brian will embark upon in the future.

These last few months have been great learning lessons for us, and we are excited to share these lessons with you.  The tagline of the show “This is the show for you, the founder who learns by doing” certainly applies to these latest developments in the business, and we hope that some of these insights help you bring your businesses along to the next level too.

If you liked today’s show,  Brian and Jordan would appreciate if you could leave a review in iTunes.