Don’t Should On Me: Stop Giving Entrepreneurs Unsolicited Advice

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Snark alert!

If you’re averse to snark, now might be a good time to redirect your browser away from this post.  If you’re still reading I assume you have a penchant for snark consumption, and to you I say, welcome, friend.

If you’re an entrepreneur working on a start-up or a bold new project, I’m sure you’ve met someone–probably a total stranger and possibly in a bar–who thinks they know so much about your business they start telling you what you should do. On behalf of entrepreneurs everywhere I say: stop shoulding on me. And please keep your advice to yourself…unless, of course, I ask you for it.

unsolicited advice

Evernote CEO Offers Advice

Before I get into all the shoulding, I’d like to point out the obvious: being an entrepreneur is challenging. So much so, Evernote CEO, Phil Libin’s advice to aspiring entrepreneurs is, “don’t do it.” Phil points out there are four reasons many people he meets want to be entrepreneurs, all of which he says are wrong:

  • They want to make money;
  • They want to be in power as CEO;
  • They are bored and want to do something different; and
  • They want more flexibility in their schedule

According to Phil, the only reason to be an entrepreneur is to change the world. So, you need to have an idea the world is missing and will fill that void; it doesn’t have to be a really big idea.  If your motivation meets Phil’s criterion, he thinks this is the best time in the history of the world to be an entrepreneur. See Phil wax philosophical on entrepreneurship in the following video:

In addition to Phil’s take, thanks to social media influencer,  Steve Farnsworth, I recently discovered a great blog post titled, The Stockdale Paradox, written by globe trotter, Niall Doherty, which perfectly articulates the way I view the challenges of entrepreneurship.  According to Niall,

“Always take honest stock of your current situation. Don’t lie to yourself for fear of short-term embarrassment or discomfort, because such deception will only come back to defeat you in the end…You must combine optimism with brutal honesty and a willingness to take action.”

For me, these are words to live by.

Back To The Snark unsolicited advice

Ridiculous pic of Mark DesJardin, Founder, GroupRide(dot)Me Getting a Bike Fitting.

My buddy, Mark DesJardin, inspired this blog post; he called me after talking with our friend, Brian, also an entrepreneur, about the frustration of strangers telling him what he should do.  Mark started a website, GroupRide(dot)Me, for cycling enthusiasts to find other riders for group rides. While talking to Mark, he said the following about strangers offering unsolicited advice:

“Don’t should on me. Don’t use the phrase “you should.” Don’t tell me what I should do; especially when I never asked for your opinion. Instead say, “have you considered…” Find out what the entrepreneur already did in the way of research, testing, etc. before you offer unsolicited advice.”

I thought Mark’s comments were so funny-mostly because I could totally relate to his point – I decided to call a few other entrepreneurs and get their take. I called three other people and once I told them the post title they immediately started laughing, and said they agreed. Here are the comments they each shared with me:

“People say things like, “you think you could do THAT?!”  Don’t make comments that are projections of your own limitations and insecurities. Talk candidly about your successes and failures, so I can learn from them.” — Chuck Bush, CEO, Great Road Capital

My favorite is, “if I were you…”  Oh, I can’t stand that one! If you haven’t successfully raised money for a start-up or are not interested in investing in my project, I’m not terribly interested in your advice.” — Anonymous Entrepreneur (she chose to remain anonymous because she didn’t want to seem too snarky! Ha!)

And finally, there is my buddy, Alan Stewart, who recently left a law firm to start his own intellectual property law practice:

People always assume what my business is like and what my limitations are. It’s a professional services view-point vis-a-vis a sales point of view.  The most irritating thing people are doing is telling me how to focus my practice without understanding my planned focus. I want to be the best individual patent attorney money can buy; that’s it. So, please stop telling me I should be a corporate attorney and all this other crap.”

Bottom Line

All of my entrepreneur friends are open to engaging in meaningful dialog about ways they can enhance their business model or improve their skill set. But they are only interested in doing so with people who really care about them and their business, or who are truly interested in helping them take their venture to the next level.  So, please, before telling an entrepreneur what she/he should do try to see things from her/his perspective.

Has anyone tried to tell you how you should manage your business and it rubbed you the wrong way? I would love to hear about it in the comments section. Snarky and funny comments are most welcome!


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James Oliver, Jr.
Dad of twin babies. Founder of WeMontage and alum of the startup accelerator. Cheeky. ESTP. Golf nut.
James Oliver, Jr.


Dad of twins. Founder & CEO of @WeMontage Featured on the TODAY Show. ESTP. Cheeky. @kenanflagler MBA & @gener8tor alum. Golf nut.
Why divesity in tech matters via @nprmichel @npr - 4 hours ago
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  1. Gettysburg Gerry says:

    Haven't had anyone tell me how to run my business, but a lot of people telling me what I "should" and "shouldn't" do.
    Sorry James that was just too darn easy…

    On a serious note, I could really relate with Alan, his statement “People always assume what my business is like and what my limitations are." That happens with me often, and I just have to keep educating. Nicely done James, thanks for sharing.

  2. Excellent post James. I think two of the greatest skills in business are : 1) having the skill to know when to shut up and listen and 2) having the skill to know when to NOT listen. I also agree that someone offering advice on things they have no experience in is quite futile (to them). It doesn't bother me so much anymore (it used to) as I have acquired adequate 'tune out' skills while at the same time trying my best not to offend the person I am ignoring.

    Lastly, like you wrote, it is very easy for people to say you should do this and can't do that. I think that is largely in part to their own insecurity. Again, I have learned to take everything with a grain of salt.

    Again, great post my man. Best- MJ

    • James Oliver, Jr. says:

      That first paragraph of your response cracked me up! Thanks for the feedback, bro. Talk with you soon. Cheers!

  3. I think a lot of the "shoulding" stems from our natural human tendency to assume everyone else is like us, thinks the way we do, and has the same skills we do. You may assume I need help with sales and marketing in my business because that's where you struggled, but I may actually be great at sales and marketing (though I may stink at accounting — LOL!) Better approach is to ask "What is the biggest obstacle for you in your business?" and then LISTEN. Sometimes us entrepreneurs just need a sounding board. If I want advice, I'll ask, and if you can help, great!

    Thanks for the post, James: it is spot on! And I love the picture of your friend Mark on the bike! :)

  4. James Oliver, Jr. says:

    Doesn't that picture rock?!!

    Really glad the post resonated with you. Been getting a lot of similar feedback on twitter. Seems a lot of folks can relate.

    Thanks for commenting, Tara.

  5. Good post James and I totally agree with MJ's input. It is sometimes difficult to 'take it with a grain of salt" but it is wise to keep the emotions in check!

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