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[Escape Velocity] – Episode #44 – Mike McDerment @ Freshbooks

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When I launched my company Clarity.fm in 2010, I gave a live demo to an audience showing how the service works.

It was my Steve Jobs moment.

From stage, I demonstrated how Clarity enabled me to call high-profile, successful entrepreneurs and get business advice from them over the phone instantly.

For the live demo, I had to call someone notable… someone the audience couldn’t reach.

I called Mike McDerment, the CEO of FreshBooks, a super successful accounting SaaS.

Mike was my example of a successful CEO.

He’s smart, committed to growth, and has scaled FreshBooks from humble beginnings in his parent’s basement back in 2004…

…to a team of over 300+ employees, raising over $75M in funding and earning over $50M+ annual recurring revenue.

Now it’s a pleasure to hand him the microphone once again by inviting him on the Escape Velocity podcast to share his infinite wisdom about leadership and growth in the SaaS space.

If you’ve ever wondered what kind of a CEO you are (or could be), then you need to hear this interview.

In this episode, we’re discussing:

  • The 3 types of CEOs (which one are you?)
  • The 3 core functions of a CEO
  • The 3 stages of leadership growth in a scaling SaaS
  • Why Mike hired an external COO with shared responsibilities
  • Dealing with inevitable growth
  • Scaling a remarkable culture
  • How a CEO’s gut instinct is your best weapon… if you train it!
  • Building an executive board
  • Why Freshbooks resisted VC investors for over 10 years
  • How to train and sharpen your CEO mind
  • Pattern recognition as a method of business intuition
  • Why he thinks Freshbooks, at 16 years old, is still in its infancy

Even now, there is still glorification of the struggling startup.

“Dude, I’m launching a startup, then I’ll be my own boss and escape the 9-to-5!”

But as any business achieves the success it sets out for, many founders struggle to morph into the person they need to be to lead a growing business at scale.

That’s why I think it’s incredibly important that you hear the experiences of CEOs like Mike and the inevitable steps that they had to take as their companies grew.

It’s better to learn this in advance before you back your business into a corner.

So I encourage you: put your earphones in and fire up the episode. It’s eye-opening.


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