How to be an entrepreneur…with a job

by jeffhilimire on February 23, 2011

I love entrepreneurs.

I love being one. I love working with them. I love events like last week’s Startup Riot where you get to spend a day with 50 startups.

I love the way an entrepreneur looks at a problem and sees a solution from an angle most people couldn’t see. I love how entrepreneurs say, “bad economy? What does that matter to me, I’m about to change the damn world.”

I love the passion that only an entrepreneur can have for his/her idea. The blind, all-consuming, never-quit passion.

I’ve been thinking a lot lately about how someone that doesn’t have their own company, but rather works at a company, can still embody that entrepreneurial spirit.

Here are a few tips on being an entrepreneur…with a job:

1. Work at a place that inspires you. If you can’t do that…

2. Make the place you work inspiring. Be inspiring. Find ways to make change. Get on committees at work that will allow you to change the vibe. Get involved in projects you care about.

2.5 But only work at a place that will allow you to do this. Don’t settle. Putting lipstick on a pig isn’t going to solve your problems.

3. Make the impossible possible. Entrepreneurs always think they can solve a problem. Make that your first reaction. “Huh, I bet I can figure out a way to do THAT.”

4. Cluster with people at your company that you enjoy, that will challenge you, that have the same vibe you are looking for. The best startups typically are a group of entrepreneurs working together, not in silos.

5. Be flexible. The ability to change the way you think and work if there is a better way is a quality of successful entrepreneurs and will serve you well no matter where you work.

6. Find mentors. I had an amazing advisory board at Spunlogic and continue to have mentors that guide me. Sometimes entrpreneurs find mentors with their investors. You can probably find some both inside and outside your company. Everyone should have mentors.

7. Celebrate.  When you have a startup and you get your 1st customer, you celebrate.  When you get your 100th customer, you celebrate.  Typically at a company you work for, especially large companies, people forget to celebrate.  At a startup each sale represents your lifeline.

8. Be positive.  I have never met a successful entrepreneur that wasn’t positive.

9. Have ideas.  Pitch new service lines or products to your company.  Invent new ways to get stuff done.  You’d be surprised how infrequent people do this at a company.

Here’s a great video from Grasshopper to get the juices flowing.  Now go out (or in) and be an entrepreneur.

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  • http://blog.weatherby.net Anonymous

    Or you could find a job that is not very challenging and be an entrepreneur changing the world at nights and on weekends until you get the startup to the point that it is all consuming. Do the thing your company does not want to focus on. Just sayin.

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  • http://www.linkedin.com/in/tonykinard @TonyKinard

    Be Curious. Investigate. Wonder why something works or doesn’t work, in the way it was meant to as well as ways it wasn’t.

    Share. Fear not. Don’t worry about nay sayers and critics who like to shoot down new ideas. Also let go of your inner critic. I often wonder how many brilliant ideas have gone unheard because of a fear of ridicule. The way I see it, for all the silly ideas you can throw out there, it only takes one to make you brilliant and memorable. ;)

  • http://www.jeffhilimire.com Jeff Hilimire

    True @lance, you can do it that way. But you can also kick all sorts of ass at your current company while still trying things on the side. The reality is (in my opinion) that 99% of the population isn’t cut out to take the risks associated with starting your own thing. However, a lot of people want to be inspired and passionate about the place they work. They want to be entrepreneurs but might not have the stomach for it. But they have many of the other qualities.

    What I’d like to see is more people trying to bring that kind of passion and change to the place they work, and if it can’t happen, probably time to move along.

  • http://blog.gleep.org/ andrewwatson

    This is what I’ve been doing now for quite some time – as you can tell from my massive caffeine addiction…

    It’s not easy – in fact there are a number of pitfalls. Your day job has to be ok with what you’re doing. This can be tricky. Some employers are ok with it as long as your not competing with them and your long nights don’t interfere with your work. I actually left a job at a massive F500 company because of trouble with the HR department and an anonymous committee of executives that wanted to review the potential conflict of interest that my startup represented.

    That was not fun.

    If you can do it… do it. Be careful about how you do it. Be prepared to stop sleeping.

    You’ve never felt so alive!

    Also, Thanks for writing this Jeff. It can feel kinda lonely being a day-job entrepreneur. :)

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  • http://www.kendrickdisch.com/ Kendrick Disch

    I’ve discovered the hard way, unfortunately, that many bosses frown on entrepreneurial ambitions. That’s why I’m working hard on item #1.

  • http://www.jeffhilimire.com Jeff Hilimire

    Yeah you’re right AW, being an enterpreneur inside a company can be tough.

    So the new debate might be, are you more likely to a) be able to get a startup off the ground and to profitability by end of year 1, or b) survive in a F500 company for a year trying to be an “intra-preneur”?

  • http://www.jeffhilimire.com Jeff Hilimire

    Checked out your site, you’ve got some mad skills! Some of your photos are crazy awesome…

    Oh, and yeah, working at a place that can inspire you is so key. So. Key.

  • http://blog.gleep.org/ andrewwatson

    Option A is hard/impossible if you have people depending on you for food and shelter and you don’t have a cash reserve from a previous exit. I think that’s what drives people into Option B.

    Unfortunately, I’ve had to scale back drastically on Option B to be fair to my employer so for now the debate is theoretical for me. The struggle is never far from my mind though.

  • http://comefortheride.com Wei Yang

    Is it really possible to have the entrepreneurial spirit and be a satisfied employee? To pull this quote by Oliver Wendell Holmes:

    “Man’s mind, once stretched by a new idea, never regains its original dimensions.”

    If you can do something you love, excel at it and possibly own it; why would you do it half-way by kicking ass for someone else and skip the ownership part? For entrepreneurs seeking partners, I’m sure this is a challenging question to answer as well.

    Of course, there are tons of people who take pride in doing a stand-up job at their companies but rule followers don’t usually think far outside the box.

  • Travis Bailey

    Heck… I just found out what an “intrapreneur” was… ;-) Happiness tends to be the key to most things in life… if you are going to spend one third of your life on something (like in the typical job), you should damn well make sure you enjoy it.

    BTW… thanks for having to bow out of Launch! This is awesome! :-)

  • http://www.kendrickdisch.com/ Kendrick Disch

    Thanks for the kind words!

    BTW, If you know any inspiring agencies looking for badasses maybe you could pass my name along? http://ow.ly/42bjG

  • Anonymous

    Entrepreneurs are often referred to as risk-takers. I think when you’re working for someone else, one of the best and simplest risks to take is asking a question. Don’t be afraid to challenge the status quo. If something doesn’t make sense and you have a better way, don’t be afraid to speak up – and be ready to back it up and take point if/when your idea gets questioned/accepted.

    Speaking from experience, a challenge you will face being an entrepreneur at your job is that people/groups/divisions/managers/etc. tend to get set in a way of doing things. It will be hard to convince them otherwise, and sometimes it takes a higher authority to get them to open their ears. The ability to tactfully go over someone’s head is invaluable for situations like this :-).

    And lastly, within those challenges are the best opportunities. A fresh perspective on a stale process is almost always a good recipe for innovative opportunities. If you have some time, socialize with similar business units and share each others processes and recent internal/external customer interactions. There are sure to be positive and productive take-aways.

  • Anonymous

    Entrepreneurs are often referred to as risk-takers. I think when you’re working for someone else, one of the best and simplest risks to take is asking a question. Don’t be afraid to challenge the status quo. If something doesn’t make sense and you have a better way, don’t be afraid to speak up – and be ready to back it up and take point if/when your idea gets questioned/accepted.

    Speaking from experience, a challenge you will face being an entrepreneur at your job is that people/groups/divisions/managers/etc. tend to get set in a way of doing things. It will be hard to convince them otherwise, and sometimes it takes a higher authority to get them to open their ears. The ability to tactfully go over someone’s head is invaluable for situations like this :-).

    And lastly, within those challenges are the best opportunities. A fresh perspective on a stale process is almost always a good recipe for innovative opportunities. If you have some time, socialize with similar business units and share each others processes and recent internal/external customer interactions. There are sure to be positive and productive take-aways.

  • http://twitter.com/moebius206 Nick Webb

    Amen. The risk is accepted by many entrepreneurs out of necessity. Faced with a stable income and secure future vs. unstable / no income and potentially a secured future of debt – but with happiness, I’ll take the bumpy road. There’s no other option for me.

    Ask me this again in 5 years, I may think differently :)

  • http://twitter.com/moebius206 Nick Webb

    Amen. The risk is accepted by many entrepreneurs out of necessity. Faced with a stable income and secure future vs. unstable / no income and potentially a secured future of debt – but with happiness, I’ll take the bumpy road. There’s no other option for me.

    Ask me this again in 5 years, I may think differently :)

  • http://twitter.com/moebius206 Nick Webb

    Amen. The risk is accepted by many entrepreneurs out of necessity. Faced with a stable income and secure future vs. unstable / no income and potentially a secured future of debt – but with happiness, I’ll take the bumpy road. There’s no other option for me.

    Ask me this again in 5 years, I may think differently :)

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