in Startups

The things an entrepreneur will never tell you

We always glorify the struggle of the entrepreneur. Late nights, poor diet and little contact with friends. It’s cliche because it is real but we gloss over just how big of a toll it really takes.

Last week I was having a drink with a recently exited entrepreneur. His last exit was a biggie at $700m+. It seemed to be amazingly well executed from the outside but as we dug in to his story over a few hours I was amazed at how much I could relate to all the ups and downs and how tenuous his hold on success was the entire time.

Here are my top things that a young (first to fifth time) entrepreneur never tells you when they are in the thick of it, and they are the things you will never understand until you are there. Not everyone deals with each of these things, but the more I talk about it openly the more strongly I feel that it is the norm, not the exception.

The focus is debilitating

“He/She is focused!”, “Man, they are hustling!” — you see an someone in action, executing rapidly and firing on all cylinders. You feel like you go to sleep and when you wake up the entrepreneur has already taken it to the next level. How do they do it?

When you start operating and you can feel the business working you get overtaken by a myopic focus that drives you from one thing to the next. You can see everything in the path in front of you: Obstacles, opportunities and a sense of momentum. To maintain such intense focus though you have to take your focus off other things, and everyone has to choose. Health, friends, family, hobbies. Nobody de-prioritizes any of these things but the problem is you don’t realize which decisions you have made until they are well behind you.

Entrepreneurs can end up wracked with guilt and wishing they had done things differently.

The focus is what gives you the highest highs, but drags you in to the lowest lows. Every win seems gigantic and every loss feels equally consequential and that is because of that myopic focus– you only see a few things in front of you and it takes a lot of maturity to be able to focus on the longer term.


The lows are real

No matter how many highs you get, most entrepreneurs feel some incredibly low times. Almost universally we put on a very positive public face and you would rarely know, but the more time you spend with fellow entrepreneurs after they have left their latest startup, they are more open about talking about those dark days.

For some of us it makes it feel impossible to get out of bed, sometimes you just can’t bear another meeting. Some founders get angry and lash out, others just hit the bottle way harder than they want you to know.

These dark periods can last an afternoon or they can last a week. They are only multiplied by the unshakeable focus I talked about above. The focus narrows even more and an obsession with certain metrics or ways out of the trough can develop.

A manic nature develops and you start to seek the next high. You come out of the low with a focus on something that you know will give you the high you need and you drive towards it harder than most normal people would.


You feel alone and you are alone

I think a big reason founders move to San Francisco or the Bay Area is because you can at least find hundreds of thousands of like minded people. You feel just a little less alone while you are single handedly taking on the world.

You learn quickly that you can’t take your problems home because one day you are up and one day you are down, or you might be both on the same day. It doesn’t feel fair to put that on your partner, and if you did they would eventually get tired of it after years of constant ups and downs.

You toughen up and you bottle it up. You are afraid to really talk about things because you can’t afford to open the bottle– it might knock off your focus and set your company back. That’s a no-no.

The best investors in the world know that entrepreneurs have this loneliness and they take time to give you a safe space to vent. Almost nobody else can give you this safe space and it takes a lot of work on both sides to develop a level of trust that allows it.


Failure isn’t an option

Failure is OK. We all know that. It’s a powerful learning tool and it is a required piece of the long term success of an entrepreneur.

Holy shit it is scary though.

You are paying salaries, the people you are paying have families and they rely on you. Your investors backed you for a lot of reasons, but you feel like you have to deliver for them.

Your customers are relying on you.

You WANT to succeed this time, you don’t want to have to go through another cycle looking for a success.

It feels overwhelming and it weighs on you. We try to relax and blow off steam, but the feeling that it’s all on you doesn’t go away.


Nobody tells you it is going to be easy, but I think a few of us are surprised by just how much of a toll building a startup can take. Maybe it is hard because it was just never meant to be easy? Who knows.

Keep at it.


  1. Jevon – awesome post.  It really is the highest of highs, and the lowest of lows.  Great heads up for those who don’t really appreciate what they are getting themselves into.

  2. Dude! You’re not supposed to tell people about these things! Argh .. I wish at least one of those wasn’t true …

  3. The sad thing about all those stories is few entrepreneurs will want to write a story about how they had it easy, because it would sound like bragging.

    So we only get stories about how starting a company is a roller-coaster that can wreck your life.

    Maybe there’s an easier way?

  4. The lows are VERY real!  Ironic that I discovered this post and blog this morning.  Yesterday my startup finally hit the very huge milestone of becoming a revenue producing entity!  I created something from an idea and someone actually handed  me their credit card number for it.  Big day, right?  Huge celebration?  Yeah, for about 5 minutes while playing around with reports on  But then I woke up this morning all torked up about my painfully low conversion rate.  Yeah, I got paid but all I can think about is how I should have hit this milestone months ago.  The lows are low and they rob you of the highs.  Stinkin’ high-robbing lows!

  5. You’ll find a couple of people who might say “I just got lucky”. I know one company like that. Early in the dot com boom they found something somebody needed, closed a $4M deal a few months in, sold to a dot com superstar, and exited the moment their shares vested. The CEO/founder was valued at close to $2B before the collapse, $800M afterward. The two lead developers each came out about $15M richer, all in the span of 3 years or so.

    But none of that made it easy. There were long hard days and nights. Days when the infrastructure nearly collapsed under the transaction load, most of the problems you see in any start-up. Still, compared to the ventures I’d been in it looked like an easy time. Nobody lost sleep wondering how they were going to meet the next payroll.

    Changing the world is never easy. Execution is never a walk in the park, and it’s never flawless. That laser focus, debilitating as it can be, is pretty much intrinsic. The way to manage it is to recognize it, manage it, try to keep some grip on the real world, and to carry on. Even if you wind up not changing the world, the only way to truly fail is to see the potential for change and then ignore it. To not even try.

  6. Very good. Dawned on me reading this great post that *bottling up* emotions can easily lead to *bottling up*.
    With the depression discussions surrounding high profile suicides by founders making their rounds I have to wonder how much alcohol plays in the equation considering its typically guised in social settings and could be a clue into the psyche of a founder with deeper issues than what appears to be apparent on the surface & behind the founder mask.

    Very good post & founders should share with spouses & others in their inner circle as a starting point.

  7. First startup, profitable the first day.  Rode that high for a long time.  Second startup, took 2.5 years just to get the first signs of revenue. Lots of lows.  What I found interesting about the lows in the second startup, was it was outside perception. Advisors that were incredibly smart, would tell us maybe to try something else.  Investors didn’t like our space or thought the opportunity was too small.  Competitors raising millions of dollars, felt like they were going to run us over.  At some point I realized I can’t control these outside variables, so stop worrying about them. Focus on what we can improve internally and go from there….

  8. I think some are easier than others,. I really have experienced some that felt pretty easy,. but the point of this is that when you look back you realize it wasn’t nearly as easy as you thought, and more often than not you made sacrifices that you didn’t realize you were making. 

  9. This is 1am at our office, I and my co-founder are working. This has become our routine for over 6 months now. Rest of the people who work in this building leave by 6pm.

    I just told one of our team member that he is out. Gosh, it was one of the most painful experience I had. The guy has a family to run, luckily he has quite few offers. This is valentine day, and a day before was launch of Pakistan’s first Metro Bus Service. People from all over Lahore were coming to see the celebration and try the service. My office is 200 meter from venue, I couldn’t go there.

    Took quite some time to learn how to focus. Still re-learning it every day, and yes I too see HIGH.Jevon, this is very powerful post. Thanks for writing.

  10. “At some point I realized I can’t control these outside variables, so stop worrying about them” — love that and it is the type of thing that takes time and maturity to realize!

  11. Great post Jevon. Lots to agree with. And for all of its hardships, I know entrepreneurship is still the right path for me.

  12. Thanks Jevon for the great and accurate article. We just passed the 3 year mark and I am still trying to keep the focus in the right direction and not take my eye of the ball. As Patrick said in the previous post: everyone has their opinion on what you should be doing. Plenty of critics that contribute to the lows but the the believers are the ones I try to focus on. Too many obstacles to list and perhaps it will make a great book some day.

  13.  Wow! You are in Pakistan? It will be great to hear more about startups from places other than the U.S.
    Well, glad to e-meet you, Waqas.

    And maybe this can help a bit:

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