Corbett Barr

Lifestyle Business Weekly

How Flexible is Being an Internet Startup Founder?


(photo by alexdecarvalho)

Ah, the current popular career option for millions of dreamers out there. Let’s assume for this article that I’m talking about legitimate software developers or people selling real items online.

I’m not talking about the “internet marketing” or “social media consultant” home-based businesses that so many hucksters are pushing these days. It seems as though people who jumped from being daytraders in the late ’90s to real estate flippers a few years back are suddenly all internet marketing geniuses. Interesting phenomenon, but it’s a topic for another post.

Let’s examine the potential flexibility for people who start a legitimate internet startup. By that I mean companies which seek venture capital or bootstrap to real revenues. I spent the past three years working on such a company, where we built an email prioritization service and were funded by high-profile VCs.

As a founder of this type of business, you probably won’t be alone. Most people choose to involve other founders. That means you won’t be making the decisions by yourself. Also, if you have venture capitalists involved, you have them to answer to, as well as a board of directors. These people will expect a lot from you, as they are investing valuable time and money in your company.

Another constraint on your flexibility will be the customers you acquire and software you’ve built. After launching your service, your customers will demand prompt support. The software you’re providing to them will have to be running 24/7. As a founder, you will have the ultimate responsibility for keeping things running smoothly. You may have employees to help, but you’ll likely be right there with them when things go badly.

The prevailing attitude (in Silicon Valley California, at least) is that only workaholic-led startups succeed. Whether or not this is true, that will be what your investors, partners and advisors expect of you. Being a complete workaholic will obviously make your time at the company rather inflexible.

Most people who fall into the Silicon Valley workaholic category believe that they will eventually be totally rich, at which point they will be able to stop working altogether. That belief is what powers them through years of 80-plus-hour workweeks. That’s great for those who succeed, but painful for the majority who don’t.

Another option (one I’m trying out myself) is to take an extended mini-retirement between startups if you can afford it.

There are alternatives to the typical breakneck pace that many startups adopt. And, truthfully, if you really enjoy what you’re working on, you won’t mind if your life is out of balance for some time.

There is a growing school of thought, captured by 37Signals’s book “Getting Real,” which proposes a much different approach. The idea is that you can build a successful company without sacrificing your health or living at the office, and that workaholics actually lower your chances at success.

This new school of thought offers much greater flexibility to the entrepreneur, but also requires a different structure than typical. Most of these flexible companies are bootstrapped. This is necessary because it eliminates demanding investors and lets the founders retain greater control.

The founders of these new breed companies must have closely aligned visions of how the company will value work/life balance. The company will often have to supplement revenues for a period of time by accepting consulting gigs. Also, these companies favor contracted labor over employees because there is less overhead associated with using contractors.

This post is part of a series about the flexibility of entrepreneurship. What are your thoughts about entrepreneurship and career flexibility?

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Corbett Barr

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  1. Hey Corbett: Good to hear from you! I agree with you that the prevailing common wisdom is that if you are not putting in 80+ hrs/week you are not start-up material. I don’t agree with it. There are times when you need to put in the hours – no doubt. But over all start ups are a marathon, not sprints. Especially if they are being bootstrapped. I am doing 4. Insane, I know! But I only do what I am good at. For the rest, I either outsource or find partners who complement me. Seems to be working for now! Look forward to your additional posts. – Ruby

    • Hi Ruby. Thanks for the comment! I know there are plenty of people out there who agree with you about taking the marathon-not-a-sprint approach. I know it has worked for you in the past. Best of luck with your current ventures. If any of them are as useful as Accelcia, you will surely have a winner on your hands.

  2. Hey Corbett, nice post. I’d say that as the cofounder of a startup, my time is flexible – almost completely so. It’s just that there’s so little of it.

    I can show up at the office any time, and I usually don’t get here til 9-11. With the amount of work we have, though, before that I’m working at home from 8am anyway. I love being able to climb or surf (if I’m that lucky) in the afternoons (when I don’t have calls or meetings, that is), but I’m usually here until 8 or 9 at least. I get to show up any time I want on Saturdays and Sundays, too.

    I actually much, much prefer long, hard, flexible hours to a soul-stealing 8-6 corporate schedule. And, at the most fundamental level, it isn’t about the money (though higher up the stack it certainly is) – it’s about the act of creation, of bringing something new into the world, of building something people want.

    I fully love it, but from my perspective it’s impossible to do for decades without at least “mini vacations” in between. Mexico sounds amazing; I’m angling for a little sailboat and the South Pacific.

    • Fantastic examples, Luke. I’m glad you’re able to make your schedule work around other activities. Do you find that you’re more productive when you get to take some time during the day for surfing, climbing, etc.? I totally agree about preferring long flexible hours to the “soul-stealing” corporate life. Even better, why not short flexible hours? At a minimum, try to fit in some extended downtime in between ventures.

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Happy ! Thanks for reading.

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