Entrepreneurshit. The Blog Post on What It’s Really Like.

Posted on Nov 18, 2012 | 172 comments

Entrepreneurshit. The Blog Post on What It’s Really Like.

It’s 4.50am. Sunday morning. And I couldn’t sleep. I have much on my mind since I just returned from a week on the road. 5 days. 3 cities.

Late night Mexican food. Beers. Airports. Delays.

I left on a Sunday. I had to miss a full day with my family, camping in the mountains. I returned home Friday night at 10pm – too late to see my kids.

I’m reminded of this feeling. It’s all too familiar. It’s what life was like as an entrepreneur. I didn’t sleep much back then. I was on the road much and I internalized much of the stress so that others didn’t have to.

And so it goes again. I’ve been on the road much of 2012 and part of 2011. According to the SEC we’re not allowed to market the fact that we’re fund raising, so I won’t. But for some strange reason they make you file your progress on fund raising, which is the widely picked up by the press. Go figure.

So it is now publicly known that we have closed $150 million in our 4th fund. Ok, well, it’s more than this but I’m not allowed to tell you specifics.  I plan to write about it early next year when we’re all through. We have a little more to go until the finish line. It has been a fascinating experience. But now you know why I’ve had many nights away, many airports and much time on the road.

And why I woke up at 4.50am. But this is nothing like the stress of being an entrepreneur. As I’ve written about before, You’d Have to be a Big Baby to Complain about Being a VC.

What’s it really like being an entrepreneur?

That was the topic of my keynote at Seedcon, an event hosted by the University of Chicago, where I am a  graduate of the MBA program.

Entrepreneurshit. The Truth About Building Starutps from msuster

I like to speak about this topic with first-time wantrapreneurs because if you read the tech press every day you’d get the impression that it all glamor. It’s not.

You’d imagine that every founder was getting rich. Actually, positive outcomes for founders are quite rare. You probably follow some high-profile entrepreneurs on Instagram and Twitter and see conference pictures of them in Davos, Mexico, Monaco or wherever. You might be psyched out into thinking you’re doing something wrong for being in your shitty little windowless office. Clicking on their glam party pictures. You’re not. You’re where you should be.

There is a difference between a Conference Ho and a successful entrepreneur. But it’s hard to know that from the press. From the Instagram and the Twitter.

As a startup founder you rarely have much money in your bank accounts. Neither in the personal nor business account. That’s stressful enough.

I recently had coffee with a young friend who just finished his first startup. It didn’t end how he would have liked. But he learned. And he’s young. And I’m certain he’ll bounce back.

He told me,

“I have $6,000 in my bank account. Throughout the course of last year I never had more than $8,000 in my account. 

I want to do this again. But I have to be careful. Maybe I need to do slightly later stage.”

He probably didn’t know but he has more in his account than most Americans so there’s that. He had raised nearly $500,000 from investors. Many are well known. He shut down his company gracefully and even thought it must have felt like a crap sandwich doing so I’ll bet his reputation is still solid with his backers.

Think about it – most entrepreneurs who manage to raise seed money or venture capital usually raise enough money for 12-18 months maximum. Many times it’s less. So at any given point you are likely operating with a maximum of 9 month’s cash.

And yet you have to ..

  • Recruit employees in the blind belief that the amazing job they’re quitting to join you will be worth it in the long run
  • Sign up customers who are paying you money for a service you can’t 100% guarantee is going to be operational for the full period that they’re expecting
  • Tell the press how great you are and hope that they aren’t publishing your obituary 9 months later rendering you a fool.
  • Tamp down the enthusiasm your naive family has about your “impending IPO” (honey, when can we buy shares? Uncle Morty wants to know) from “your successful daughter” (we’re so proud of her! she’s so successful! we always knew she would be. she was so precocious in high school. that’s my daughter – did you see her mentioned in the New York Times!) Shit, ma, stop sayin’ that. I don’t want you to have to eat humble pie with your friends next year!
  • Raise money. Need money. More money. Yes, please give me money. No, I don’t really know if I’m going to be able to return it. But without it I know I’m forked. I need it. So I’ll ask anyway and hope like hell I don’t have to avoid you at future cocktail parties. Quick – why don’t entrepreneurs celebrate when they raise money? Because they know that they’ve just signed up for much more obligation.

Early on in my first company I had an employee ask if it was a good time to buy a home. We had less than 6 months’ cash in the bank. I was pretty sure we were going to raise another round of capital. But not sure, sure. I mean you never know if your investors are REALLY going to keep backing you. And you can’t go around telling all of your employees your deepest insecurities about it or you’ll soon have no more of said employees.

Trust you? Yeah, I trust you. But why don’t you just give me the damn term sheet you promised so I can trust you even more.

You have secret doubts about your co-founder. She seems depressed. And she isn’t pulling weekends anymore like you are. I know, right? Total bullshit. She’s just not as committed as she once was. I don’t think she really believes any more. If I told my VCs would they then lose interest in our next round? Would they blame me? Would they back me or think I had gone off the rails?

So Facebook just announced that they’re going to compete with you. Apple announced that they’re shutting down your category. Salesforce.com just bought your main competitor. Your main competitor just raised $75 million and took all of the oxygen out of the room.

Far fetched stuff. If you’re not an entrepreneur. If you’ve been one for a while you know how much you fear every WWDC. Every F8. Or DreamForce. What announcements are going to crush you? [I wrote about what to do when this happens here.]

My biggest fear as an entrepreneur? I was worried that I was going to get married and be on the altar unemployed. “There’s my son. He should have been a doctor like his father!” Truthfully, that’s one of the things that kept me going. I didn’t want to disappoint.

I didn’t want to disappoint my parents. My wife. My employees. The press who trusted me enough to report on our successes.

I didn’t want to disappoint my customers. People seldom understand that when enterprise customers choose your software it isn’t just a purchase order. It’s a human being inside the buying organization who has trusted you. He went to his bosses and asked for budget. He beat down the other factions that wanted to choose your competitor. He has staked his reputation on a project to use the software of some shitty 2-year-old startup company because he believes! In you.

So you ask why on Earth being a founder is stressful?

No, it’s not as bad as working in coal mines. But it is quite the roller coaster and the stress is real.  Some people love roller coasters. Others prefer a smoother ride.

One of the most asked questions I get about being a VC who was formerly  an entrepreneur is if I ever miss being an entrepreneur? Do I ever want to go back to it?

Of course I do! How could you not want to go back to it. It’s addicting. It’s an adrenaline rush like no other.

I often answer this way:

It’s like sports. If you have a chance to be on court and shooting 3-pointers as the game clock is winding down OF COURSE you still want to be on the court. There is no comparable feeling from the sidelines.

Yet one day you wake up and you realize you can’t run as fast as the young guys. You can’t quite hit the 3-pointers as often. Yes, you have maturity that makes you a wiser player. But you realize that you can be more helpful as a coach.

And yes, I sleep better at night as a coach. And I’m happy as a VC.

Remember that if you choose to be an entrepreneur or to at least try – it’s stressful for everybody who does it. Your competitors have just as much angst as you do. You read their press releases and think that it’s all rainbows & lollipops at their offices. It’s not. You’re just reading their press bullshit. They have their secret doubts. And they’re in their offices reading your press releases and wondering why life is much easier for you. And they’re fighting with their co-founders and struggling to ship code on time.

As I like to say, “we’re all naked in the mirror.” We stare at our own imperfections. And then we go out everyday and see everybody else in their fine threads and wonder why it’s much easier for them.

Being an entrepreneur is about finding your inner self confidence.

  • To be constantly told “it won’t work” but to keep plugging away anyways.
  • To be kicked a lot and still keep standing.
  • To hide your demons so that you don’t scare the bejesus out of your employees.
  • To inspire others to join your cause when by all rational accounts they should not.
  • And having the cojones to have them join you anyways. Pottery Barn rule. You hire them, you own them now. As in your responsible for these lines on their future resume. Don’t fuck them up.
  • To swallow your stresses and insecurities and keep your optimistic game face on in the office. And on your home front. Maybe even try to believe it in your own head.
  • It’s about wanting the right speaking slot at an important conference and hounding the organizer until he lets you do it.
  • It’s telling your creditors that you need 60 extra days to pay. Please. Yes, most entrepreneurs will be nodding their heads right now. Not fun, hey? But that’s what it takes.
  • Firing? Hell, get used to it. It’s a necessity. You better be good at it. Develop a thick skin for it. Not put off the difficult fires. You don’t have the spare budget to suffer fools. Hire fast, fire faster.
  • Friday night in the office while others are at the bar. Sundays in the back of a plane. Center seat. Smelly dude next to you.
  • Investor emails. They are forwarding you yet another mother fucking link to an article about your competitors. And wondering why the hell are we not doing THIS like they are. Enough already!?! I told you not to worry about their move into Latin America. I promise you that won’t be a bit market for us. What? No, I’m not worried that they’re higher in the App Store charts than us. They’re paying for traffic. Paying I say! They can’t have a positive LTV on these downloads. You want me to throw around my money like that too, bro?

Hell, I send those emails. I’ll admit it.

Entrepreneurshit. It never ends. It’s not all glamor. It’s mostly not glamorous at all. It’s just something you have to do. Often because you’re unemployable. Your impertinence would get you fired in 2 days for telling your boss he’s a fuck wit. And it’s why you probably will quit on day 366 after the acquisition.

You’re unemployable. You’re an entrepreneur.

It’s not for everybody and you shouldn’t feel bad if you aren’t one of those that chooses this life. You’ll probably be healthier and wealthier. Despite the fact that only the Lotto winners get reported. Many more people play.

But if you do want to go for it, don’t wait. It doesn’t get easier later in life. It gets harder. You’re probably going to fail or have limited success. The math says so. So better that you try as young as you can when failure is easier to bounce back from. When you can wear it as a badge of honor.

I’m not ageist. I’ve backed several entrepreneurs in their forties. No problem. I’m just telling you that if you’ve never done it before and WANT to then the earlier you try, the better. That’s all.

Good luck. Enjoy the ride. I’ll be rooting you on from my far comfier seat on the sidelines. Secretly. Wishing. I were still in the game.

If you want to read more on the topic:

** Images from top were from this week’s travel. The left hand side was dinner, terminal 3, Chicago O’Hare. The right hand side was the view from my two-hour delay at Newark Airport. Nice view, actually.

  • Raph


    This is Raph, the co-chair of the Chicago Booth Entrepreneurship and Venture Capital group who moderated the Q&A portion of your talk. Thanks again for giving this presentation at SeedCon; I know that it was very well received by the participants.

    We’re planning another event in Las Vegas, wherein ~100-150 MBAs pursuing entrepreneurship from the top business schools in the country will be meeting for a two-day summit. Would you be interested in giving the keynote address on Friday, 2/15/13?

    The purpose of the event is to allow students from each of the top MBA entrepreneurship programs to hear from prominent entrepreneurs such as you, network, participate in a value-creation competition, and have fun.

    If this sounds like something you’d be interested in, and could let me know, I could provide any additional detail you may need.

    Thanks very much,


  • shivam

    yes please more articles like this and more time to read them, as much as i love the life of an entrepreneur it is basically a life where you always need more time, more money and more people ( customers, employees…..)

    and no matter how much i bit** about this life i will always be an entrepreneur ( hopefully you will read about me soon)

  • scandelmo

    Mark, one of your best posts! I am reminded of my favorite quote and why we respect the “the man [or woman] in the arena…” it’s the hardships in the attempt that defines success. Thanks!

  • mm41

    thanks for telling the real story, mark. embarrassed to say i actually teared up bc you hit on all the key emotions and truths that are inherent in this journey. and people rarely talk about them.

  • Hungry Globetrotter

    This is one of the best posts you have written and they are usually all very good. After a few hard weeks in the grind, it’s great to read it. Thank you for this!

  • http://www.bluecoastrecords.com/ Cookie Marenco

    glad I wasn’t the only one. I’m on my third startup. The last two were fine little lifestyle businesses. Re-living dorm room life and top ramen is tough at times, as is turning down investment for a bad deal. But it’s worth it to wait for the right people to be involved with and see a vision realized.

  • Raph

    This quote reminded me of your talk: “As a startup CEO, I slept like a baby. I woke up every two hours and cried.” — Ben Horowitz

  • Carissa Ganelli

    “You might be psyched out into thinking you’re doing something wrong for being in your shitty little windowless office.”

    All I can say is THANK YOU for stating the above. Yes, I did think I was the ugliest girl at the party whom no one asked to dance because we’ve spent our time building our business vs. begging Techcrunch to write about us or attending SXSW. This despite the fact that we got (and turned down) a $1M term sheet, we launched 9/15 and signed a few (paying) clients in 2 weeks, and will have a bit of revenue this year.

  • Meri

    This is so true !! the process, the emotions, and expectations are 100 % what it is like to launch a start-up. It should be mandatory reading in all entrepreneur classes in the world.

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    Great post, thank for share! I will return this blog to read more useful posts. Thanks!

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    Its a very good post. I was very pleased to find this site.

  • nope

    This is a totally, completely, brilliant article. It sums up my life as an entrepreneur perfectly. But I love being on the ice with the game on the line and not up in the stands in a comfortable seat. Wouldn’t trade it for anything, even though it might kill me.

  • Robert Capelli

    knowing that we are unemployable is always great for the stress factor… very good read.

  • Filiberto_J

    Hi Mark, I’ve been reading your lines from back some time already, but this post is kind of special. it is like the voice inside my head…Great Article!

  • http://www.versioneye.com/ Robert Reiz

    Thanks for writing this. This article pretty much reflects my life as CEO at http://www.VersionEye.com but it still is much better then being an employee in a Bank!

  • just saying

    you should have started with this comment lol

  • David Szabo

    Hi Mark, just found&read your article. It’s really great how clearly you point out all the important aspects of being an entrepreneur. In my experience if any of those people who keep saying they’re “proud of me” and stuff just because I decided to become an entrepreneur (a.k.a. unemployable as you highlighted) would knew how I live my life, they’d think I’m crazy. Maybe they’re right. :)

    BTW I read in the comments about how does it feel having no money at all as an entrepreneur. Well, it’s the most inspiring thing ever, you don’t need to “create a sense of urgency”, your bills do that for you.

  • http://cariloop.com/ Michael Walsh

    I’m a bit late to the party…but still had a great time being here! Incredible article and insights, especially applicable on a day like today where I woke up at 3:45 AM to get into the office, catch up on everything from yesterday that I missed, and dive into another 16 hour hustle session. Thanks for sharing!

  • Aaron McLean

    Great read. Thanks to Gunter for sharing.

  • AKA ALadyWhatCanDoBusiness

    Yep! Is all I have to say. 10 years down the line here and just now talking exit for the first company whilst starting fund raising for the second. It’s the longest, hardest, most painful, unappreciated, experience imaginable but no other choice for those of us who are unemployable 😉 Do or die! What doesn’t kill you will make you stronger… ‘Wantrepreneurs’ should hear all the horror stories and maybe they will make less mistakes than us as a result. I am looking at ways of helping.

    I started my company whilst I was pregnant after losing my job. Maxed out a credit card to buy all equipment needed for a business concept and got on the rollacoaster. I have raised my child and built a highly successful and widely respected mobile marketing company,servicing some of the largest brands in the world (raised c$2m)… but not without continuous internal torment and physical exhaustion.

    Entrepreneurs do this crap – we are made strong to endure it. My daughter is 10 and beautiful and happy. Nuff respect! 😉

  • Shefa Weinstein

    Thanks for the post. You understand what is going on in our heads and its always great to feel a part of something bigger. But I will have to stop reading your posts on the late train home, people are looking at me when I randomly start laughing :)

  • John McMahon

    Lived these very words for 13 years before successful acquisition. To say it is not for everyone is to understate.

    I believe there is a lucky few maybe 10-20% of pure entrepreneurs (perhaps this number is growing with the times changing) who are perfectly suited to this lifestyle and have the right aptitude(s) to pull it off.

    Even then, luck, timing, location, and more luck and you see the odds stack up.

    Overall, speeding up the process is in your best interest, the one thing you can never make more of is time… the more chances you have to play, the better your odds of a win.

    Once you’ve built and sold a business, you sort of “go over the top” and gain new access/respect but mostly insight. And from that side of the wall I can say, again, speed it up.

    Learn fast by executing plans well.

    To help new companies do this, I’m putting together a mobile app for new entrepreneurs based upon lean startup methodology… a pipeline for new entrepreneurs into a plug and play business model system. http://starter.io