What It’s Like To Be A Startup CEO – The Backstory

Posted by Jessica Alter /July 19, 2012 / FounderTalk, Uncategorized

This FounderDating Guest Post was written by Paul DeJoe as part of our FounderTalk Series. He’s a serial entrepreneur, hard at work on Ecquire - lead management software - and well known for his recent post on Quora: What Is It Like to Be a Startup CEO?  

Since a Quora post I made a couple months ago about what it’s like to be a startup CEO, I’ve received over one thousand emails from entrepreneurs across the World and have done about 50 Skype calls. They were motivated to connect because it felt like they met someone who understood them. So, when FounderDating reached out to me they asked if I could elaborate on some of the times that shaped my post and that I alluded to so that entrepreneurs could get a sense of my experiences, I said yes. Immediately, three immediate specific experiences came to mind that are etched in my brain forever.  I hope this helps you in some small way and let this post serve as evidence that things are never as bad as you think.  

Tough to Sleep

At the time it was happening, I was convinced that the lowest point I would ever feel with Ecquire was when I was sleeping in my truck. If you think sleeping in your car is bad enough, try having to balance worrying about being robbed, the angle which would shield the most glare from the lights, realizing the only place to park is in the parking lot of your new employer and getting sleep so I could actually do my job.

Ecquire had been at a stand still and I was living with my brother in Arizona to save on costs.  There was at least 6 months worth of development that had to be finished before I could sell anything.  I couldn’t justify enough work to be full time at Ecquire or justify giving myself any money from the little that we had.  An opportunity came up to be an interim CFO and VP of Product that I had to take in order to pay both myself and to put money back into Ecquire to keep it running. Unfortunately, it was on the East Coast and I didn’t have time, money or the luxury of getting out East and finding a place to stay before I could take the job.  I had to start as soon as possible.  I told people I was staying with friends but I was either rolling out a sleeping bag in my office if it was late enough and no one was around or I was sleeping in my car outside the office if people were working late.  I made sure to set my alarm for around 4:30 in case anyone was coming in early.  I’d go to the YMCA do a workout and get a shower then go eat breakfast with someone new every day.  I’d be in the office by 8AM every day.  I did it for a week until I found an apartment but I was never more productive and focused. Every minute of the day had to be calculated and it forced me to look for efficiencies and improvements all the time.  The times that suck are the closest thing we have to a time machine.  You never forget these times but normal days come and go.  

Normal for you is different than normal for other people. There’s people that will read this and find it completely ridiculous. Indeed, the people that I care about and love the most find it ridiculous. I certainly don’t claim to be a successful entrepreneur but it feels like the characteristics of those that are successful answer each challenge with hard work and doing whatever-it-takes – even if it means sleeping in your car.

Difficult to Talk to Friends

When I thought that the lowest point was behind me, I heard from my brother that a few close friends and relatives were talking about me when I wasn’t around and saying, “Why doesn’t he just man up and get a real job?”  That statement was on constant replay in my head and I said it to myself a few hundred times when I first heard it.  It was debilitating.  It wasn’t that they said it that bothered me, that was actually understandable. What bothered me was that it felt like they might be right.  And when you let that thought creep into your head it manifests in no time. The people that we love have powerful influences over us because we want them to be proud of us and don’t want to disappoint them. I put my headphones on and ran for 40 minutes and with each step I took that comment rang in my head.

I was never more motivated to finish what I started than after hearing that.  I still repeat it to myself every day.  I thank God that I heard it.  I realized that you can choose to get excited at the challenge when something overwhelming or impossible is staring at you or you can let it paralyze you. All you have to do is put one foot in front of the other and you’re on the path to conquering it.  That’s how the “adrenaline junky” side of me comes out and what other entrepreneurs I’ve talked to use as motivation.  This is what they live for: Doing what others won’t and say can’t be done.  Choose to let criticism motivate you.  

The most challenging thing is that the people you’d normally share your challenges or fears with don’t understand the concept of “I’m gonna create something huge with nothing and I don’t care if I die trying.”  If you share your challenges with them it feels partly like admitting they were right for telling you to “get a real job.”  I’m a stubborn entrepreneur, so that doesn’t sit well with me. There’s also a feeling of, “I can do it myself” and you always want to be a leader among your team.  be calm and collected so sharing that you’re scared shitless most nights of the week doesn’t do much for confidence. So, there are few people to really talk with. But this is part of the territory; we can’t really complain.  

What Have I Done?

And even though I can say these things and know they’re true, the real lowest point I had was when my parents came into the living room and sat down next to me during Christmas of last year.  I thought they were going to tell me that one of them was sick because I had to have that talk with them before and they had the same look.  Without any context, my Mom just started crying and said, “We’re so worried about you, Paul.  You don’t have any money or any stability.”  I FELT AWFUL.  This was undoubtedly the lowest point along this journey.  There’s not much worse than realizing you’re putting your parents through physical anguish and seeing the feeling of helplessness and worry on their faces. I sat there for a minute – utterly devastated.

But then I had to kind of laugh and my response was “You don’t have to worry about me.”  I said,  “I get more out of life than anyone else I’ve ever met. I’m having a great time, I’m not gonna die and I’m not gonna go to jail. This might scare you but I’m actually not afraid to die, I’m petrified of being bored and knowing what’s gonna happen tomorrow.  You’ve given me every opportunity in the World to chase my dreams and most of my motivation is to make you proud.”  

Equire did raised a round of financing not long after that and has paying customers giving us great testimonials.  The greatest feeling I’ve had since we started down this path happened last month when I saw my dad. I told him we created 5 jobs.  He didn’t have to say anything, he was proud.  

Staying the Course

So, stick with it. When things are really tough remember what matters: 

  • The people you love and that love you.  
  • Being true to yourself and passionate about something worth pursuing everyday. Your health.  
  • Leaving something better than when you found it.  Being grateful for what you have.  

And, of course, remember my low points and that I’m still standing.

Work hard and be nervous if people (even those that love you) don’t tell you you’re crazy.  Make your own luck and, as always, email me any time if I can ever help you with anything at paul [at] ecquire [dot] com.