What’s It Like To Be An Entrepreneur?

I get asked some version of this question, often in the form of “I’m thinking about becoming an entrepreneur”, every day. It’s awesome to me that lots of people are asking this question but it’s really hard to answer with a simple, short response. I’ve been pointing people at a number of resources to help them get a feel for what being an entrepreneur is like and two that I’m involved in top the list.

The first is the book Do More Faster: TechStars Lessons To Accelerate Your Startup that I wrote with David Cohen in 2010. There are a bunch of reviews up on Amazon – mostly good – that capture the spirit of what we were trying to convey. Whenever I’ve aimed it at someone who asks what it’s like to be an entrepreneur or wants to learn more about what’s in the mind of an entrepreneur, I usually get the feedback that it’s useful. What surprised me early on was the feedback from early employees at startups who told me it helped them understand what the founders of their company were going through. I recently skimmed through it again just to make sure it still felt fresh to me and it does.

The second is Startup Weekend. If you’ve never done a Startup Weekend, it’s an incredible simulation of entrepreneurship. In 54 hours you’ll go through the experience of starting a company from scratch, surrounded by others doing the same thing. You’ll compress a lot of the activities into a weekend, especially dynamics around team, idea, and trying to get something out the door quickly. It’s valuable for existing entrepreneurs as well –  if you are an entrepreneur looking for smart people who want to get involved with startups, it’s a great recruiting ground. I’ve known and supported Startup Weekend from the very first one that was held in Boulder in 2007 and joined the board last year to amp up my involvement.

While there is no substitute for jumping in the deep end and starting a company, I believe both our book and the experience of Startup Weekend are great ways to get a deeper perspective of what it’s like to be an entrepreneur.

What are some of the things you point people at to answer this question?

  • James Mitchell

    Some good blogs on what it is like to be an entrepreneur include:

    You Really be a Startup Entrepreneur?”

    Mark Suster


    “Should I
    Become an Entrepreneur?”

    Jeff Bussbang



    Po Bronson


    High Stakes, No Prisoners: A Winner’s Tale
    of Greed and Glory in the Internet Wars

    Charles H. Ferguson


    The 11
    Harsh Realities of Being an Entrepreneur


    on “The 11 Harsh Realities of Being an Entrepreneur”


  • warpaul

    Marc & crew have done an amazing job w/ Startup Weekend and your book is definitely the bible for startups. I also like this Quora response, which garnered 1,600 up-votes, because it’s cuttingly depictive of what it’s like to be a founder (or CEO) of a startup… http://www.quora.com/Startups/What-does-it-feel-like-to-be-the-CEO-of-a-start-up

  • Yasi Baiani

    Brad – you are absolutely right. Startup Weekend is a great experience to test the water and see how it is to be an entrepreneur, bring a team together, and lead everyone to launch a product and market it to others all in 54 hours.

    I attended Boston Startup Weekend a few months ago with an idea that I had for a while. I was fortunate that 17 people showed interest in working on my project. After selecting 7 people to work on the product, we were able to crank and build the basic version of ActivePepper (www.activepepper.com), which is a location-based mobile and web platform that helps active individuals find the right sports partners and activities based on their availability, location, and skill level.

    Startup Weekend was a great experience for us and our company is live since then. Two of the people on the current team are from that Startup Weekend. We are making a lot of progress both with the product and business. Our experience of being entrepreneurs so far has been great and exceptionally rewarding. We encourage everyone to give it a try.

  • Frank Miller

    Being an entrepreneur is about having a good idea and executing, period. If you don’t have a good idea and you’re not spending 95% of your time building and selling it, none of the rest matters. While I am interested in many of these books and blogs, they seem to me like those self-help, motivational books. They might make you feel better, but they’re not going to get you there. You need a product you can sell, simple as that.

    • Totally agree that they won’t get you there. But for someone who isn’t spending 95% of their time building and selling their good idea, there are lots of ways to better understand the dynamics.

  • The word entrepreneur wasn’t always as cool as it is now. I’ve found that many people, including myself were entrepreneurs before we realized it, by running sole proprietorship or small brick and mortar businesses. So maybe people are really asking “What’s it like to be a founder of a (potentially) high growth startup”, since that is pretty much what people consider entrepreneurs these days.

    Actual entrepreneurs are everywhere, they cut your lawn, cut your hair, and cut your taxes. But their story doesn’t garner many movie rights.

  • an internship or job experience at a startup will also give you a great inside view on entrepreneurs and how they run their businesses. There are lots of lesson to learn from these type of experiences

    • Awesome suggestion – we do a ton of that in Boulder and you are right on with this suggestion.

  • My answer to this is to mention A Tale of Two Cities, specifically the ideas that interweave this tale of enterprise, revolution, poverty violence and love between London, Paris and the new America

    It opens “it was the best of times it was the worst of times”, and for my money that is what the ride has been like thus far.

    @msuster describes this as an emotional roller-coaster – absolutely!

    This is the city of dreams:

    “I see a beautiful city and a brilliant people rising from this abyss, and, in their struggles to be truly free, in their triumphs and defeats, through long years to come,”

    This is the social enterprise:
    “I see the lives for which I lay down my life, peaceful, useful, prosperous and happy”

    and Cartons closing words are the “apologia meo”:

    “It is a far, far better thing that I do, than I have ever done; it is a far, far better rest that I go to than I have ever known.”

    To me this means – It is better to try and to die trying – than not to live – these are the choices that must be made.

  • Until you either have significant skin in the game, or are earning a living from the venture, it is just a MBA exercise.

  • When I approached my mentors on this subject, they provided the following response: You don’t *think* about becoming an entrepreneur. You *are* an entrepreneur when you have an internal burn (whether that is an idea or vision) that will not leave you and haunts you. Being an entrepreneur is not a profession, it is a calling.

    • Well said. I talk a lot about that in my book Burning Entrepreneur.

  • Jai

    “Do what you like to do” = “Entrepreneur”

  • Startup weekend – a ton of fun – went to the one in Portland back in april.

    Startup weekend as simulation of a real startup – I dunno. After having worked at 3 startups – startup weekend was unlike any of them 🙂

    I think the weirdest thing about startup weekend was that there were teams (including the one I was on) with >10 people. This was just weird .. fun … great people ..but still a little weird.

    Startup weekend as a place to recruit – yes! One of the guys (sw dev) on our team recently quite his day job ..after getting a taste at startup weekend.

    • Good point – I don’t mean that it’s exactly the same, but rather there are tons of elements of a startup all crammed into a weekend.

  • DJ

    I tell people it requires a high tolerance for ambiguity.

  • The interesting aspect of being an entrepreneur is WHEN your realize you are one. I started with an idea of writing down computer problems businesses have and the solutions. After a few months, a business person said I should write a book. Nice, did not think about that, but here goes. Next, a person told me, “It’s not about your book, it’s about the content, which can become a seminar, workshop, DVD, webinar, etc.” Oh man, the shackles are off the brain now. This process took a number of years for me, I’ve heard of stories of other entrepreneurs having a similar situation of taking multiple stabs at doing something and then looking back and saying, “Oh yea, that’s what I am now!” So while Brad does the Founder thing, I’m doing the “Dog Sitter” or “Personal Trainer” approach. Oh, and more 50+ year olds start businesses than 20 somethings, so if Brad were aware, he’d counter the “The 30 Under 30” bias in entrepreneurship and get the word out. https://www.createspace.com/3403435 😀

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