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

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