When (or when not) to Side Hustle


In my last email, we talked about the great Oracle of Omaha himself, Warren Buffett and how you could inject a little of his approach into how you run an agency. The second part of a Buffett-like approach is the “putting all the eggs in one basket, and watch the hell out of that basket.” The idea being that you should make fewer investments, but go big when you do and give it all you got.

No Side Hustles?

Have you ever come across a book and learned all you really wanted to know from the title alone?

I’ve had a few meet that criteria and quite honestly the best book I’ve never read is called “Don’t Start a Side Hustle” by Brian Page. Why this resonates with me so well is that for so many years I asked myself, “why are so many owners trying to get away from the agency business?” I’ve seen agencies (typically smaller ones) add all sorts of side projects to their product spectrum from t-shirts to food, to softwares and more.

I have to imagine that many of these side ventures weren’t successful. Many side hustles turn into a second time suck that hurts both the agency and the side hustle. The reason to side hustle as a business decision, good or bad, comes down to the why. Here are reasons on both sides of the coin when it comes to the idea of side-hustling or not.

Good Reasons

  • It’s a strategic pivot based upon a clearly identified opportunity with a solid plan for success.
  • You have achieved a successful, profitable, and sustainable agency model and your time is better put to use elsewhere, lest you get in the way.
  • It’s part of an experimentation process towards a grander vision for the business. Jeff Bezos had to solve selling and distributing books before he could solve anything and everything at your doorstep.

Not So Good Reasons

  • It’s a distraction from solving the fundamental challenges in your agency business.It feels better to work on a new idea, rather than a source of stress.
  • You got dragged into it vs being part of a bigger plan.
  • You’ve grown tired of selling time, anything that isn’t that sounds amazing.

Clearly not all side hustles are bad. It might not make Mr. Buffett happy, but sometimes you just have to scratch creative or passionate itches.  In fact many owners, started their agency as a side-hustle. There is likely a fine line between a pivot and a side-hustle.

At this point, out of principle, I can’t read Mr. Page’s book. But I’d like to think what he meant to title the book as, he just ran out of word space, “Only Start a Side Hustle If It’s For a Good Reason or It’s An Expansion of Your Current Strategy and Vision.” Or perhaps another way to think about it, you have to earn your side hustle.

I’ll ping him and see what he thinks.

An Agency Story – Featured Episode

Episode graphic for "An Agency Story" podcast with Jeff Gapinski - title Surge - Hosted by Russel Dubree - picture of Jeff in the lower right corner smiling.

Jeff has quite the agency success story and I suspect it will only get better. He’s invested heavily into the growth of his business, and more importantly his people.

Want to start a side hustle or are you in a hustle but think you might be doing it for the wrong reasons?

I’ve helped several owners align their side hustle to their main business or helped them navigate why they don’t need one in the first place. Just reply to this email and we’ll chat about it.


“The Backboard”

P.S. Christmas is in 60 days.