So today, everyone has a side hustle, or so it seems.

Almost everyone in sales seems to be into real estate, either “multi-family” real estate or getting their broker’s license. Or other so-called “passive” income streams that really often take many hours to manage. And so many folks are coaches, selling courses, and more.  Others are very hands-on advisors, spending many hours per month at startups other than the one they work at.

And many founders and CEOs don’t like it.  They may tacitly support it, but I don’t know too many that like it. 

Aren’t they already being paid to do a full-time job?  Isn’t it inherently a distraction if it’s anything more than an hour or two here?  Don’t they seem to be working on their side hustle on LinkedIn with even more enthusiasm than their day job?  Well, maybe.  But the new generation in tech seems to have normalized the side hustle.  I don’t see things going back to the way they were.  Everyone wants “multiple revenue streams”, even if that means doing none of them as well as they could if they focused.  And really, side hustles got even easier once we all became distributed and worked on Zoom.  Who will really know?  You don’t have to constantly duck into a conference room or phone booth to take a call for your other gig anymore.

And with anxiety over job losses at a recent high, many will get some comfort in having a second income stream

But what about at the VP level?  Especially a VP of Sales, working on a big number, and with presumably, a big upside and OTE?  If a VP of Sales has a $500k+ OTE and a big team to manage, does it even make sense to sell courses on the side?

The survey results are in and they’re interesting.  Over 4,000 of you voted. And most think it’s either fine or at least OK for a VP of Sales to have a side hustle:

When I started in “tech”, there was an unwritten but often spoken rule.  Once you had something, once you had scale, then go help one other startupJust one.

As a CEO, serve on one other board.   As a VP, be an advisor to one other.  One other was great, if it was a good one.  You’d be challenged, gain perspective, and see how others are approaching things.  That was the rough rule.  Spend a few hours a month helping one other good startup.  As you can see below, for example, Peter Gassner, CEO of $30B Veeva, also serves on the board of $20B Zoom.

Perhaps it’s only natural that’s expanded from a few hours to a second job, and from helping one other startup to learn to … being an advisor to 4-10 or more.  And in some cases, really to being both a VP and running a second senior job at the same time.

What I do know is just this.  I’ve benefitted a ton from learning new things from others, from serving on some boards, to advising a bunch of unicorns and more.  But past a certain point, it’s hard for me to be truly great at something when I’m doing more than one thing. 

I can be good doing more than one thing, but not truly great.  I think most founders think that way, too.  Being truly great requires a 110% commitment IMHE. But more and more of the rest of your company … doesn’t think that way.  Especially in a world where many VP tenures don’t even last 24 months.

It’s a new world.

And one interesting real-world example.  Peter Gassner, CEO of Veeva, also serves on the board of Zoom, as noted above.  He was granted 1,202,720 shares to serve as an outside director.  Those shares today are worth $70,000,000 (!).  Wow.  But he owns about 13% of Veeva as the founder-CEO.  Those shares are worth about $3 Billion today.   As founders, maybe do one of these for sure.  Being on the board of Zoom, I am sure, has been an amazing experience, and a good one to learn from.  But I’m also confident Peter would never let himself get distracted.  That’s $3 Billion in value from the day job, vs a “mere” $70m from the board seat. 😉

In any event, many leaders now are going to have significant side hustles.  So here’s my rule: Disclose it.  Tell your boss.  Make sure they know.  It also sort of covers your rear on some level.  If you’re reluctant to disclose it … maybe that’s a sign.  Too many folks hide their side hustles, either fully or partially.  Hmmm.


A few thoughts on both sides of the “issue” from founders, VPs and more in the great comments here:

“All those answering yes are VPS with side hustles or who hope to one day have side hustles🤣. Depends on the size of the company. Big company old-school do-nothing-but-think-I’m-valuable-VPS….sure. Under $20m revenue and still needs to get their hands dirty VPS…no way if it’s competitive (in sales and requires hours. Owning an airbnb, doing a podcast, coaching a team, volunteering or trading cards – that’s a hobby and a side-hustle and very much encouraged). But something similar that is essentially a second job? No. We may be wrong, we just won’t support that here. ”

— Tony Knopp, CEO and co-founder, TicketManager

“Fantastic Poll.. But, so many people voted “No, not OK?”  This makes me nervous.. encouraging a world where individuals have a high cost of living but absolutely no diversified income streams for themselves and their families. Their life and mental security, then, based on statistically one of the world’s least stable jobs (VP Sales lasting an average of 1 year tenure). I don’t wish to see more people in increasingly bad financial standing this year. I hope that a great VP of Sales is a high bandwidth individual who possesses the capability to keep multiple ‘hustles’ concurrently successful. Be that including their businesses and personal relationships. Diversify your income streams. Build your personal brand. Secure your family.”

— Ash Takher, Former VP of Sales at Optimizely, TikTok, SAP

“A VP of Sales should have a large variable component. The more time spent unlocking revenue for the business, the higher the commissions earned by the VP. I’ve thought about various side hustles, but they all require more effort and yield less money per hour than if I just dedicated more hours to my current job. Side hustles make sense for fixed income earners. Otherwise, chase those uncapped commissions!”

— Micheal “MJ” Paradiso, RVP at Yext

“No way. It sucks as a boss having to try accommodate an employee who has passion working outside of your company. In fact, I try to avoid anyone altogether who is not going to give 100%. In SaaS and in small businesses in general, the competition is too difficult to do things half-arsed especially for someone in sales who most likely will be put in conflict of interest situations just by associating himself/herself to an external opportunity. Same holds true for developers.”

— Anfew Lentii, CEO TOPP Tactical Intelligence

“Considering most VP of Sales are axed around 18 months. You should have a side hustle. I wish I had been told to do this a long time ago. Don’t put yourself in financial distress because you were sold on the next unicorn; that is just a donkey on its last leg.”

— Dwayne Ernest, GTM Strategist

“Problem with any of these situations is if things are going well then it’s not an issue. if things go sideways at your main gig, or if it looks like you’re even a little behind, the side gig can and will be used against you. it might not be the cause of poor performance but try explaining that to your boss/team. GL”

— George Avetisov, Founder & CEO,

“The reality is that everyone today has a side hustle. If the VP is delivering and it has zero impact on his work then why not. One of the most interesting polls I’ve seen lately.”

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