Hi, I'm Dave Shepherd.

Welcome! This is my online home and what follows below is a bit about me and what interests me.


Sports and Activities

These tend to change about every two years, but I love the challenge of learning how to do something physical. This is what has me excited now:

  • Beach Volleyball - I wish i passed as well as I hand set
  • Surf - I'm a big guy on a shortboard. Not a lot of turns
  • Golf - Struggling to stay a single-digit handicapper
  • Surf skate - so much fun to rip around a bowl


My favorite topics are economics, psychology, history - especially the American Revolution, biographies, and a bit of fiction.

The four books that had the biggest impact on me are 1984 by George Orwell, A New Earth by Eckhart Tolle, The E-myth Revisited by Michael E. Gerber, and the 4-Hour Work Week by Tim Ferriss.

The book that I've gifted to the most people is Traction by Gino Wickman.

Favorite Things To Do

  • Fly fishing - Is there anything better than walking the banks of a small river?
  • Camping - the more adventurous the better
  • Travel - I just like new experiences and practicing Spanish
  • Podcasts - Up First, Planet Money, What Bitcoin Did, Pivot, Making Sense, Stephen Livera Podcast
  • The Factual - the best news source without wasting your time on news entertainment

Work Experience

I spent 10 years at HubSpot that culminated in being the Country Manager for Australia and New Zealand. I was responsible for a $50 million dollar business that included Sales, Marketing, and Customer Success teams.

When I started at HubSpot we had $15 million in revenue and when I left we were at $1 billion. It was an amazing ride and learning experience.

While most of my time was spent leading very successful direct and channel sales teams, I had two memorable challenges that taught me the power of perseverance and passion: (1) I got demoted after my first year as a sales manager; and (2) I built a new culture of success for our 70-person office after finishing Q1 at ~70% of our target. I can't explain how bad things were and how much "trouble" we were in.

What's next

After taking a sabbatical that started in August 2020, I'm looking to take on the biggest challenge I can think of: starting a new business.

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