Entrepreneur · Motivation

Why are you doing this?

Jimmy Jacobson Full Stack Developer and Cofounder at Wedgies.com

June 24th, 2014

Being an entrepreneur can be tough. What motivates you? What gets you up in the morning? Why are you doing this?

Jimmy Jacobson Full Stack Developer and Cofounder at Wedgies.com

June 24th, 2014

I would love to hear what everyone thinks about this.

I've worked at some great companies as an employee. Like Overstock.com and Zappos.  354 days of the year I was happy, challenged and worked with other great people pushing new ideas and products forward. But there was always one day that I dreaded. The annual review.  This was the day when my managers would compare me to a checklist that was usually decided upon by the HR department of what made a good software developer.  It always seemed to ignore the parts of the projects I was the most proud of. 

Hackathons and Startup Weekends were my gateway into Entrepreneurship.  I discovered that the things I loved to do had a name and a job description.  I do this because my career path isn't to be an engineering manager at a large software organization.  Being an entrepreneur gives me the opportunity to develop and use the skills that make me happy.  Even when it's really hard.

Steve Douty CEO of Nexo, Inc.

June 25th, 2014

Way back when I was interviewing for jobs out of college, I remember answer a question like "What motivates you in life?" with "I want to make a difference."  It sounded smart, important and I truly did want to become a CEO one day - but I didn't really understand what it meant.

Now on my sixth startup, I do understand much more about what I was trying to say. (I did chuckle at Dimitry's comment about world peace.) It doesn't have to be on a grand scale - but if you start a company, you can actually choose how you want to make that difference. You can pay attention to how companies and people are struggling and find solutions that make things better for them. And, if you've found the right problem, hired the right team and directed the right work - you get rewarded.

The potential financial rewards are obviously great. There is also the feeling that your company was able to have a positive influence people's work and/or personal lives. Back in the 90s, BSG helped pave the way for client/server computing and Hotmail made email simple. In the 2000s, Moxie Software helped the employees of large companies collaborate in a different way and now with Smaarts we're changing the nature of enterprise security.

Not everything you touch will be successful - VCs have a track record of one home run out of 20 companies, and maybe a few singles. But I've learned more from failure than from success. So if you have an appetite for learning, starting a company is one of the fastest paths to sating it. And if you keep trying, your hard work combined with a measure of good luck will pay off.

Plus, you actually do have some control over the culture of the company - because you will hire people you love to work with, and they will do the same, and so on. When you're dumped into the middle of a huge organization, that ship has sailed and half of your job is understanding it, playing the game and avoiding getting trampled by it. Regardless of the pablum on their web sites, 99% of large companies are not entrepreneurial. (For fun, take a look at employee reviews on Glassdoor.)

The happiest people I know have more than just money in their pocket - they feel like they've made some sort of positive change or contribution, no matter how large or small.

Brandon White CEO of Zeuss, Inc.

June 24th, 2014

It's simple, I can not imagine doing anything else. I love to build things that solve problems and I'll be dead someday and may not get the chance to do it so I take advantage of every waking minute.

The tough part of being an entrepreneur is the fun of it for me. Every day you wake up with an adventure ahead of you, you get a chance to put your head on the pillow at night having possibly made or created something you had no idea about when you woke up. I go to sleep looking forward to waking up.

Once you have been an entrepreneur a while you realize that even the toughest times will pass into good times, the impossible becomes possible because you imagine it. Getting through the tough times is simply about having "courage" and "persistence". Courage is not about not being scared, it's about being scared but doing it anyway. Persistence is about keeping going even when you think you can't. The satisfaction of getting through things far outweighs any of the negatives, at least for me.

Mike Masello

June 25th, 2014

Thank you for putting this thread out there.

I agree with a lot of the sentiments above.  I've always loved my job, but like you those dreaded annual reviews where everyone has to fit the same template were a spirit killer. What brought me here was an experience where I worked day and night for a year on a web redesign, and when it launched it doubled the company's sales overnight.  The forecasted impact was about 1/10th that.  Despite this I was told I wasn't good at my job.  It was by far the most successful project (talking $$$) in the company's 7 years of existence.

I don't ever want to be in that position again.  Being an entrepreneur provides the opportunity to be rewarded for risk and effort that you just can't get as an employee.  You can chart your own path.

The most difficult part is I do/did really enjoy the team environment.  So that's another motivator to succeed is to get to a point where you have team members to bounce ideas off of, share in successes, etc.

Dimitry Rotstein Founder at Miranor

June 25th, 2014

1. Because I tried working at a big company, having an inferior superior, working when THEY want me to, not when I want to, with 14 vacation days a year pending permission... it's just not for me. I was miserable and level-7 depressed all the time. Entrepreneurship is an emotional roller-coaster, they rightfully say, but even at the lowest points I'm no worse than at that big company, except that over there that low was a flat line, rather than a point.

2. Because I hate my neighbors with their barking dogs, booming music, night parties, and petty jerkness (if there isn't such a word there should be). My only hope is a house with no neighbors around, but I can't afford anything like that on a programmer's salary, at least not without seriously lowering my standards of living. I'm not desperate enough to become a monk or go living in the woods like Tarzan, so my hope is to become sufficiently rich to escape.

3. Oh yes, and world piece :-)


June 24th, 2014

Because being busy all the time means I don't have to cope with social awkwardness!

Kind of joking, but workaholism should be kept in check I now recognize.

Real answer, you must be the change you want to see in the world.

Steve Douty CEO of Nexo, Inc.

June 25th, 2014


Thanks for the heartfelt comment. The only thing I would add is that you can either create a company yourself, or apply your skills to an early-stage startup that you relate to and that will appreciate your willingness to speak up and shine a light on the truth. 

The best people I've ever hired were those that were always in my face and challenged me and knew that I valued their willingness to "tell it like it is."


Gaurav Chawla Founder

June 25th, 2014

The only way to guarantee a great future if to invent it. My view is, own a problem, and do the best possible to solve it the way you would want it solved. And not wait for someone else to solve it. Great leaders create great companies where motivated employees work with a sense of purpose. I was always inspired by how great leaders rally amazing people to work with them not for them. Its not about management and employee, us vs. them. In modern corporations, power is not in the hierarchy. Just giving money and title to employees doesn't guarantee you that great people will be motivated enough to do their best work. After money is taken off the table, the drive comes from purpose. It is responsibility of a good true leader to find that purpose and create a team of people who are behind that purpose, not the possibility of earning a lot of money at some point. For me its this purpose that gives me the drive. Its the possibility of impact that my work can have on the people and world around me. If I can leave the world a little better than I found, I would die very happy.

Eric Sullivan CEO at FoundationLab

June 25th, 2014

Jimmy, my company was built to help entrepreneurs validate and bring products to market by acting not just as dev's and designers but as strategic partners. Which is extremely gratifying. You have someone who is extremely passionate about an idea but lacks a lot of the experience they need which going through the process can take making a lot of mistakes which in turn burns cash. Helping them to alleviate these mistakes and do things right the first time it's a lot of education for them on the fly but is very rewarding throughout the whole process.

Shobhit Verma Ed Tech Test Prep

June 25th, 2014

I have to share my favorite story here. It has haunted me for years.

To pick a sun. - By a mathematician friend of mine.

He lied to her. . He told her that he was going out, to pick a handful of clouds and sew a cap for her. Actually he was not. He was going to pick a sun.
As if there are many suns. But back then, there were. The days were too dazzling then, and there were no nights. He was unsure of which one to pick. He chose the closest one.
She never suspected it. Once or twice, when he talked about it, she asked him, what the need was. There was no answer, because there was none at all. Why bring a sun so close, and where is the space to keep it? Even he knew there was no need. It is just one of your games, she said to him.
Sometimes in the night, she awoke at the sound of his footsteps pacing the hall. Thinking
and restless, that was him. She never suspected, she was drowsy in love.
Then one dawn, he set out. He had his bag of tools with him. He went up to the tower, that he had built over the years, secretly and in silent devotion. All this time, He had it hidden from her, so that he could give her a surprise, when it was fully done. That day, he thought , he would wait a little longer and make the surprise a bigger one, with a sun under his arms.
He went up to the top floor, and took the kite out. Within moments, the kite was a flag of victory, .ascending in full glory ,while its metal edges shone in the shower of daylight. He started pulling the string, which was superfine and almost invisible.
Then it happened. Making a brilliant swirl, the kite caught the edges of the sun. Then it wrapped itself around it., just as a cunning snake would do. He felt the sun coming closer to him. He was happy, elated, satisfied.
But what he didn’t know was that he would spend an eternity there. Because the moment he caught the sun, he had died. The sun was not coming to him, nor was he approaching it. It was an illusion. Instead he was destined to revolve around the sun , slowly , and for ever. One full year for one round. He didn’t know he had died..

She could not believe he had died. It was impossible. She was angry that he could lie to her so badly. But when she saw him, there ,-- a dead man making his rounds, she cried out loud. She just hoped that he will come to life. She couldn’t pray, they had no gods back then.
She hoped in vain, and she watched him changing shape. Nothing of his dark agile frame remained. He won’t be able to dart like lightning, jump over the backyard fence , and catch her unawares. Never again .Instead he had grown obese, like an orange.
She watched in silence, as she saw his surface getting rough and rocky. She saw floods
ice , and oceans carving out of his once strong torso. She saw ugly and unshapely land masses jutting out of the swelling confusion.
She had stopped loving him, and she could not continue this for a dead man. And when she saw moving jellies, running about in the oceans, dividing themselves and joining each other, in random pairings, she was filled with disgust. Yet a trace of a hope remained. Maybe she would see him alive. Then she would ask him one question that occupied her since he left. What was the need?

As time went by, she saw huge mammoth like creatures roaming the surface of his Lover. She saw insects, fish, and tigers. She was now prepared to leave him for ever. Then something caught her attention.

Out of the dust of the body, she clung to, loved and cherished, and which was now a rotten trash hole, there arose some figures resembling him. They were much shorter than him, but equally graceful. She was shocked to see her own image in the figures that followed. The long flowing hair, the pouting lips, the delicate smooth gestures. She saw them making love, unabashedly, in rain, in caves, in open wide spaces, as if it all belonged to them She looked at herself, a round silvery object, -- a cosmic waste. She felt an attraction towards them, an attraction very different, from what she felt towards her Lover. She felt that she should stay and watch over them. It was a feeling she never had before.
There were Men and Women, once again .

But then, suddenly, a fear of the worst kind gripped her. As she lay in quiet guard, she discovered that some of the Men are not sleeping. She could see them, moving restlessly along the verandah, thinking about the dawn. Some were taking a cold bath, removing the odor of the feverish love-slumber, still hanging loosely over their beds. She knew their intention, and tried to distract them. She made crisscrosses of her own shadows, and tried to instill the magic she once practiced on Him. She hid and reappeared. Sometimes she weaved her unearthly innocence into the face of their lovers, still asleep. Sometimes she succeeded in making them turn to their rooms, the smell of honey-suckle and olives, greeting them to their bed and putting them at ease. They would then go to sleep.
For some, the seduction works. For the unfortunate ones, it doesn’t. Her tricks are a nuisance for them. They have set their faces towards the unknown dark, and are tugging at the rope of future, with grim resolve. They are just waiting for Her to pass away from the horizon. Then, at the crack of dawn, they would pick up their bag, and stealthily move out of their homes. They have a mission. They have the sun to pick.