The 7 Habits of Highly Effective Mediocre Entrepreneurs

I’m pretty mediocre.

Particularly as an entrepreneur. I’m ashamed to admit it. Many of the readers here are great visionaries. I’m not even being sarcastic.

I have reason to believe Larry Page reads all of my articles. Elon Musk prints out my articles and tapes them to his bathroom wall just in case he forgets to bring a book in there. Kanye and Kim discuss over breakfast the merits of the points I bring up.

I’ve started a bunch of companies. Sold some. Failed at most. I’ve invested in a bunch of startups. Sold some. Failed at some, and the jury is still sequestered on a few others.

I'm not being false humble (I think. Maybe I am). My podcast is good but it never climbed to the heights of a Joe Rogan or anywhere close. My books have sold copies but never changed my life the way I see the books of many of my friends change theirs.

I've been doing Standup Comedy for almost five years. I'm having fun. Not sure the audience is! I'm probably pretty mediocre.

My feeling, based on my own experience, is that aiming for grandiosity is the fastest route to failure.

For every Mark Zuckerberg there are 1000 Jack Zuckermans. Who is Jack Zuckerman? I have no idea. That’s my point. If you are Jack Zuckerman and are reading this, I apologize. You aimed for the stars and missed. Your re-entry into the atmosphere involved a broken heat shield and you burned to a crisp by the time you hit the ocean. Now we have no idea who you are.

(below: lots of results for "Jack Zuckerman")

If you want to get rich, sell your company, have time for your hobbies, raise a halfway decent family (with mediocre children, etc), and enjoy the sunset with your wife on occasion, here are some of my highly effective recommendations.

THE SEVEN HABITS OF HIGHLY EFFECTIVE MEDIOCRE ENTREPRENEURS

PROCRASTINATE

In between the time I wrote the last sentence and the time I wrote this one I played (and lost) a game of chess. My king and my queen got forked by a knight. But hey, that happens. Fork me once, shame on me. Etc.

Procrastination is your body telling you you need to back off a bit and think more about what you are doing.

(I was supposed to write this book. But I procrastinated so much that the publisher finally said "no" (after I wrote "The Power of No" for them). The reason I procrastinated? I realized I was horrible at asking people for things.)

One time I was procrastinating on joining the board of a company. Something just felt funny. They were eager to get me on and they kept telling me, "we're putting out the press release today."

Eventually they did! And suddenly I was on the board. A year later they were out of business. I lost money. I lost opportunities.

I procrastinated but maybe a bit too long. But it was a lesson. The next time I got an offer like that and I started procrastinating I told the company "no" (after they were calling me for about two weeks wondering where I was).

Procrastination is the best signal. Don't ask "why am I procrastinating?" Just listen to it.

When you procrastinate as an entrepreneur it could mean that you need a bit more time to think about what you are pitching a client. It could also mean you are doing work that is not your forte and that you are better off delegating.

I find that many entrepreneurs are trying to do everything when it would be cheaper and more time-efficient to delegate, even if there are monetary costs associated with that.

In my first business, it was like a lightbulb went off in my head the first time I delegated a programming job to someone other than me. At that time, I went out on a date. Which was infinitely better than me sweating all night on some stupid programming bug (thank you, Chet, for solving that issue).

(the right attitude for a procrastinator)

Try to figure out why you are procrastinating. Maybe you need to brainstorm more to improve an idea. Maybe the idea is no good as is. Maybe you need to delegate. Maybe you need to learn more. Maybe you don’t enjoy what you are doing. Maybe you don’t like the client whose project you were just working on. Maybe you need to take a break.

Maybe (this happens to me all the time) you got overly excited at first, made a bunch of random commitments, and now regret it so you are procrastinating. If so, welcome to my life.

There’s only so many seconds in a row you can think about something before you need to take time off and rejuvenate the creative muscles. This is not for everyone. Great people can storm right through. Steve Jobs never needed to take a break. But I do.

Procrastination could also be a strong sign that you are a perfectionist. That you are filled with shame issues. This will block you from building and selling your business. Examine your procrastination from every side. It’s your body trying to tell you something. Listen to it.

ZERO-TASKING

There’s a common myth that great people can multitask efficiently.

This might be true but not for someone mediocre like me.

And I have statistical proof. I have a serious addiction. If you ever talk on the phone with me there’s almost 100% chance I am simultaneously playing chess online.

The phone rings and one hand reaches for the phone and my other hand reaches for the computer to initiate a one minute game. Chess rankings are based on a statistically generated rating system. So I can compare statistically how well I do when I’m the phone compared with when I’m not on the phone.

There is a three standard deviation difference. Which means if "me on the phone" played "me off the phone", then "me off the phone would win about 997 times out of 1000.

Imagine if I were talking on the phone and driving. (Which is probably why I am not allowed to drive in four different states). Or responding to emails. It’s the same thing I’m assuming: phone calls cause a three standard deviation subtraction in intelligence. And that’s the basic multi-tasking we all do at some point or other.

So great people can multitask but since, by definition, most of us are not great (99% of us are not in the top 1%), its much better to single-task. Just do one thing at a time. When you wash your hands, hear the sound of the water, feel the water on your hands, scrub every part. Be clean. Focus on what you are doing.

Often, the successful mediocre entrepreneur should strive for excellence in ZERO-tasking. Do nothing. We always feel like we have to be “doing something” or we (or, I should say “I”) feel ashamed. Sometimes it’s better to just be quiet, to not think of anything at all.

Out of silence comes the greatest creativity.

Not when we are rushing and panicking.

FAILURE

As far as I can tell, Larry Page has never failed. He went straight from graduate school to billions. Ditto for Mark Zuckerberg, Bill Gates, and a few others.

But again, by definition, most of us are pretty mediocre. We can strive for greatness but we will never hit it. So it means we will often fail. Not ALWAYS fail. But often.

I made so many mistakes in my first successful business I’m almost embarrassed to recount them.

One time I was trying to pitch Tupac’s mom that I should do the website for her dead son. I had a “CD” (what’s that?) of all my work.

I went to Tupac’s manager’s office and he said, “ok, show me what you got”. The only problem was: I had never used a Windows-based machine. Only Macs and Unix machines. So I honestly had no idea how to put my CD into the computer and then view its contents. And I had gone to graduate school in computer science. He said, “you have got to be kidding me”.

It was a $90,000 gig. It would’ve met my payroll for at least two months. It was a done deal until I walked into his office. I left his office crying while he was still laughing.

When I came back to my office everyone asked, “How did the meeting go?” I said, “I think it went pretty well.” And then I went home and cried some more. I roll that way.

(never got to do his website)

Ultimately, life is a sentence of failures, punctuated only by the briefest of successes.

But here's the key": Turn possible failures into experiments.

For instance, you want to make a brand new fashion line? Don't start an entire business yet (which could fail). Learn "the 10,000 experiment rule". This is the most important rule in surviving The Great Reset we are going through.

This rule says that if you do 10,000 experiments (or 1,000) you'll have an infinitely greater understanding of something than anyone else on the planet.

If you want to start a fashion line and you're confident, start by doing experiments. Maybe make Facebook ads with pictures of your clothing photo-shopped onto a model. Put a $100 budget behind them. See if there is a greater than 3% click-thru rate. To where? Doesn't matter. Just see.

If there is a greater than 3% click-thru rate then you might have a great idea with this fashion line. Come up with the next experiment (maybe a Kickstarter). Less than 1% and your idea is bad. You failed. But it only cost you $100 and a few minutes

So your worst case scenario is that you learned. You learned about fashion. You learned about Facebook ads. You learned about your audience, etc. Experiments are a way of short-circuiting failures so there is no worst-case scenario.

The more I failed the more risk averse I got. I learned how to do experiments. I live my life now by doing experiments (unfortunately for my wife who has to put up with me wearing pajamas all the time right now for an experiment I am doing).

Failure means you are "fragile". Experimenting makes you (as Nassim Taleb puts it) "anti-fragile".

BEING UNORIGINAL

I’ve never come up with an original idea in my life. My first successful business was making web software, strategies, websites for Fortune 500 companies. I wasn't the first to do this. I was the 100th.

In the 90s, people were paying exorbitant multiples for such businesses. My successful investments all involved situations where I made sure the CEOs and other investors were smarter than me. I wrote a TechCrunch article on this titled “My Angel Investor Checklist”. 100% of my zeros as an angel investor were situations where I thought I was smart. Where I thought I had identified an original ideas.

I wasn’t. I’m mediocre.

The best ideas are when you take two older ideas that have nothing to do with each other, make them have sex with each other, and then build a business around the bastard, ugly child that results.

The child that was so ugly nobody else wanted to touch it. Look at Facebook: combine the internet with stalking. Amazing!

Look at Airbnb: Hotels + "Access Economy". Or Andy Warhol: "Art + Pop Culture". Federal Express: "Mail + Cheaper financing for planes". Coolio's "Gangsta's Paradise": Hip-hop + Stevie Wonder's R&B song "Pastime Paradise".

(Stevie Wonder and Coolio)

Facebook wasn't original. It was about the fifth attempt at such a social network. Twitter: combine internet with antiquated SMS protocols. Ugly! But it works. Ebay, combine ecommerce with auctions. The song, “I’ll Be There”. Combine Mariah Carey with Michael Jackson. If Justin Bieber sang John Lennon’s “Imagine” it would be a huge hit. I might even listen to it.

POOR NETWORKING  

I had a party at my house before the lockdown. I thought I would have fun. It was nice seeing people. For about 20 minutes. Then I went to my room and only left in two minute spurts until the party was over.

Even when I want to, I seem really bad at returning calls, sending emails, keeping up with people. "Hey, how are you. Was just thinking about you!" I wish I were better at this. I want to be. I don't know why I'm so mediocre at this.

When I was running businesses I was often too shy to talk to my employees. I would call my secretary from downstairs and ask if the hallway was clear, then ask her to unlock my door and I’d hurry upstairs and lock the door behind me. That particular company failed disastrously.

But many people network too much. Entrepreneurship is hard enough. It’s 20 hours a day of managing employees, customers, meetings, and product development. And the buck stops here sort of thing. And then what are you going to do? Network all night? Save that for the great entrepreneurs. Or the ones who are about to fail. The mediocre entrepreneur works his 20 hours, then relaxes when he can. It’s tough to make money. Not a party.

DO ANYTHING TO GET A "YES"

Here’s a negotiation I did. I was starting stockpickr.com and meeting with the CEO of thestreet.com. He wanted his company to have a percentage of stockpickr.com and in exchange he would fill up all of our ad inventory. I was excited to do the deal.

I said, “Ok, I was thinking you would get 10% of the company.” He laughed and said, “No. 50%”. He didn’t even say “We would like 50%”. He just said, “50%”.

I then used all my negotiating skills and came up with a reply. “Okay. Deal.”

Great negotiators can easily walk away from a deal. If you can't walk away from a deal then you are just negotiating the terms of your future imprisonment.

But I'm mediocre. If I want a deal to happen then the best I can do is to try not show my desperation.

I’m a salesman. I like people to say yes to me. I feel insecure when they so “No” or, even worse, if they don’t like me. When I started a company doing websites we were pitching to do “miramax.com”. I said, “$50,000”. They said, “No more than $1,000 and that’s a stretch.” I used my usual technique: “Deal!”

But the end results: in one case thestreet.com had a significant stake so that gave them more psychological stake. And for my first business miramax.com was now on my client list.

So Con Edison had to pay a lot more for their website. I’m a mediocre salesman and probably a poor negotiator although I try to learn from the best. When I see a great negotiator I pay attention, remove ego, and even write down notes as quickly as I can about what made him or her great.

But because I rush for the "yes", I get more deals done, I get the occasional loss leader, and then ultimately the big fish gets reeled in if I get enough people to say “yes”. It’s like asking every potential partner on the street to have sex with you. One out of 100 will say “yes”. In my case it might be one out of a million but you get the idea.

POOR JUDGE OF PEOPLE

The mediocre entrepreneur doesn’t “Blink” in the Malcolm Gladwell sense. In Gladwell’s book he often talks about people who can form snap correct judgements in two or three seconds.

(sometimes people walk up to me and say, "I loved your book, 'Outliers'!" or " 'The Tipping Point' changed my life! Thank you for writing it!"and all I say is, "Thanks.")

My initial judgement is almost 100% wrong about people. I wish I were a better judge of people but I just can't fool myself anymore into believing I am.

But I KNOW this about myself. One time I was going into a meeting where a company was going to pitch me an investment.

I knew I didn't like the investment. I had done due diligence. There were a million red flags. I brought a friend with me and I said, "No matter what I say afterwards just yell at me, 'NO!"

During the meeting, the CEO of the company convinced me. This is the best investment ever. He answered all my questions. Did away with all the red flags. I wanted to invest! Let's do it!

I said afterwards, "I have to admit, I might have been wrong. This looks pretty good." My friend turned to me and yelled, "NO!"

Two years later, I just found out the other day that the company is out of business. I'm so gullible and easily convinced. But self-awareness is a good friend to the mediocre. List your weaknesses and don't try to stop them. It's hard work to fix yourself! Be aware and then find work-arounds (like bringing a friend you trust). That's what effective mediocre people do.

—

“I thought being mediocre is supposed to be bad?” one might think.

Shouldn’t we strive for greatness. And the answer is: “Of course we should! But let’s not forget that 9 out of 10 drivers think they are ‘above average in driving skill.'”

People overestimate themselves. Don’t let overestimation get in the way of becoming fabulously rich, or at least successful enough that you can have your freedom, feed your family, and enjoy other things in life.

Being mediocre doesn’t mean you won’t change the world. It means being honest with yourself and the people around you.

And being honest at every level is really the most effective habit of all.