The Kind of Entrepreneur Nobody Talks About

April 12, 2015

If you follow news about entrepreneurship, most stories you hear in the media and blogosphere are typically about two kinds of new companies:

  • Startups — usually tech startups — that land VC funding, then scale as quickly as possible

But there’s another option somewhere in between, a “hidden breed of entrepreneur,” as Andrew Wilkinson wrote recently on Medium. Wilkinson founded Flow, the task-management tool my team uses to stay organized. It’s an impressive app with a loyal user base (although frustratingly, you don’t hear about it as much as Basecamp or Asana), supported by a growing team… all without outside funding. Oh, and they’re not based in Silicon Valley, either.

Because he hasn’t sought out funding, Wilkinson explained, he’s sometimes branded a lifestyle entrepreneur, which isn’t exactly a compliment in startup land. But in truth, he’s one of the hidden breed, a bootstrapper who’s working hard, building a scalable business and making good money.

Options for running your own business

The middle ground of entrepreneurship

The startup world often dismisses this type of entrepreneur or simply forgets we exist. As I wrote about last year, convincing investors to put money into your business is touted as the holy grail of entrepreneurship. If you never get to this level, the startup cult would have you believe, you haven’t truly succeeded as an entrepreneur.

But what if growing a big, venture-backed company isn’t what you want? What if you’re not interested in trading your autonomy for funding and growing as fast as possible, even if it negatively affects the quality of whatever you create and, more importantly, your life?

“The siren call for many entrepreneurs isn’t money, it’s freedom,” Wilkinson writes. “The freedom to chart your own path, the freedom to build what you want with the people you love. Taking money, building a board, and raising rounds takes away that freedom little by little.”

Look hard around the web, and you’ll find other hidden entrepreneurs who feel the same way. Erica Douglass, who sold her web-hosting business for $1 million at age 26 and now owns two bootstrapped, profitable companies, sang a similar tune in a recent blog post about why so many funded startups fail.

“Tech companies, especially funded ones, tend to get a lot of press these days, but to me, the media isn’t telling the whole story,” she writes. “Sure, it’s great to write about the 0.1 percent of businesses that will have off-the-charts growth. But there are also plenty of interesting stories to be told about all the companies that employ people, serve happy customers, and make great money for their founders! From my perspective, it’s a lower-stress business to run, as well, which suits me just fine.”

As you might have guessed by now, I’m of this hidden breed, too. I started my content marketing business, Socialexis, as a freelancer, without intention to scale, but discovered a huge demand for blog management. Now we have a roster of clients and an amazing team to service them.

Which puts me in that middle ground that’s rarely talked about: I’m no longer a freelancer, but I’m far more interested in slow growth and doing awesome work than becoming the biggest and most profitable blog management company around. I still value my autonomy, but I also love working with my team, and, to be completely honest — because we don’t talk honestly about money enough! — scaling has also allowed me to earn more income.

Thinking outside the entrepreneurship box

There is another option here, a middle ground between stressful, VC-backed startup and laid-back, not-in-it-for-the-money lifestyle entrepreneur. And you can deviate at both sides of the spectrum, too: some funded startups like Treehouse work four-day weeks rather than pushing their employees toward burnout, and plenty of lifestyle entrepreneurs work hard to rake in the big bucks.

(For the record, while freelancers are often entrepreneurial, I think of them as their own category, and they have characteristics from each group: they typically bootstrap, work really hard, maybe outsource some tasks here and there, and earn a decent but not crazy-high income… but they don’t scale.)

As Wilkinson wrote, the folks in the middle ground “aren’t getting written up on TechCrunch, they’re just quietly building great businesses and cashing dividends in their little corner of the internet.”

If that’s you, take comfort in knowing there are others in that corner, too, working toward the same goals, with similar priorities. That corner’s actually a pretty great place to be. Any of these options are, really — so long as you’re pursing not what everyone tells you is hip or hot, but what truly makes you happy.

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13 Replies to “The Kind of Entrepreneur Nobody Talks About”

  • Carrie Smith says:

    This is SUCH a good point, and a topic that needs to be discussed a lot more. It’s a category I find myself dabbling into as well, now that I’m not just a freelancer anymore. My only hurdle is that I don’t have a “title” to call myself, or a specific category that’s properly defined. Not that I want to be in a category, but it’s something to hold on to and to share with others when they ask what it is that I do. Any thoughts on this? What do these in-between-ers call themselves? Bootstrapping entrepreneurs? Small biz owners? Nothing quite fits yet.

  • Great article, Alexis. What would you say about freelancers who sell beyond what clients buy? For instance, writers selling books, hosting podcasts, coaching, doing webinars, etc., from their sites. Or is that a title other than freelancers, which is why you make the distinction between freelancers and entrepreneurs? Curious …

    • Alexis Grant says:

      Hi JP!

      To both your question and Carrie’s question above, I’m not sure it really matters what everyone calls themselves! I think you and Carrie are probably describing bloggers, or entrepreneurial bloggers/writers. I think the difference between that and this middle ground category is scaling — building a business where you have a team of employees, one that doesn’t rely on you doing the work to run.

      But no matter what we call ourselves, we’re all carving out our own unique careers =)

  • True, Alexis, and thanks for the reminder that it’s not necessary to call anyone by a certain name. I am one of those people who wants to tidy everything into neat little boxes! 🙂

    Love the idea of working with a team one day … that’s my 10 year plan (or maybe five?). Thanks again for another inspiring post. Much appreciated.

  • Kevin Kermes says:

    Phenomenal piece, Lexi!

  • Erin says:

    Great post, Alexis. Besides the fact that I don’t want to run a traditional company with everyone sitting in one office, I worked for software start-ups during the first dotcom boom and saw how much control the founders gave up in return for funding, and the corners they cut when the focus was only on growth as fast as possible to satisfy your investors. (Check out the show Silicon Valley for a humorous take on this).

  • Saya Hillman says:

    Amen amen amen! When I read “The siren call for many entrepreneurs isn’t money, it’s freedom,” in his post, I couldn’t nod fast enough. Thanks for spotlighting this topic, Lexi.

    In my early years, though I was successful in that I had clients and could pay the bills, I always felt unsuccessful because I didn’t have a ‘real’ office, employees, investors, a home in an incubator, slick business cards and tshirts, etc. Well, eleven years later, I’m still standing and many of my peers who had all of above have folded.

    Always makes me think of Covey’s imagery: you don’t want to climb the ladder of success only to find it’s leaning against the wrong wall.

  • Anshu says:

    Finally, someone wrote about us too.
    It really drives me nuts that IT companies with years and years of losses on their balance-sheet get written about in the press just because some big-shot VC funded them with X million dollars. On the other hand, people who are building up a viable, successful business from scratch by working hard, re-investing profits and being disciplined and smart about their expenses are ignored as the small fishes, not worthy of any attention. Its like organic growth, real profit, paying customers don’t matter anymore. I’m often terrified by those episodes of Shark Tank where people exchange 20 – 50% equity of their business for few thousand dollars. I would think long and hard before signing off any part of my business to someone else…If I do that, it will be for a very good reason. A few thousand bucks aren’t going to cut it.

  • Andrew Marshall says:

    Lovely article Alexis!

    It’s good old quality vs quantity debate. I always say I aim for quality but with enough quantity; sure we all want to grow but at a rate that keeps things manageable and fun!

    It’s not really worth doing if it’s not fun anymore…

  • Sarah Lusby says:

    Epic piece Alexis – Shared 🙂

  • Kashif says:

    The definitions of startups, and entrepreneurs, are pretty messed up these days. People, who were called self-employed professionals, are now known as entrepreneurs, their businesses – startups.

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