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Watch out for no-man’s land on the road to bootstrapping a start-up

This article discusses the no-man’s land in which bootstrapping startups often find themselves.

Many service companies, including our own, would love to follow in the footsteps of successful people like Jason Fried and David Heinemeier Hansson at 37signals, or Ryan Carson at Treehouse—transitioning from a client-services company to a products company, through bootstrap funding.

And it’s understandable! Who wouldn’t want to work on something that you own, love and fully control, and be in a situation in which your earnings are no longer a direct function of your available time?

But getting there requires, in most cases, the willingness to make up-front personal sacrifices—serious personal sacrifices—dedicating yourself consistently and with discipline to the goal, for what can seem like a long time. And the demands during this time can seem unreasonable, or even impossible.

Attempting to make that journey without the willingness or ability to make the necessary personal sacrifices, one can find oneself in a no-man’s land, which is worse than being a fully-engaged client-services company. And that’s the subject of this article.

Been there, done that

When I started Makalu Aerospace, back in 1997, and bootstrapped its initial growth through personal savings and part-time consultancy, I remember five years of nothing but dedication to the destination.

There was no distinction between weekdays and weekends, no holidays, no shopping, getting around by bike (didn’t own a car) and otherwise minimizing our costs—and living off personal savings, as the company didn’t become profitable until around the fifth year.

It was an extended period of intense effort. In fact, the only five-year period in my life, during which I possibly worked harder was my time spent at Georgia Tech. Interestingly, though, it didn’t at the time really feel like a sacrifice. Pretty much the only thing I wanted to do was reach that destination.

My own experience is consistent with that of every person I know who has built a successful company, as well as nearly all those I’ve indirectly observed.

Categorizing available time

Before looking at what success, the road to get there, and what we’ll call “no man’s land” look like, let’s start by conceptually chucking how we spend our time into four broad categories.

  1. Product work This is the time we spend getting our products to the point where they can fully fund the running of the business, or at least to the point where it looks like an acceptable risk to go all-in and make the final push. In my experience and observations, this is a huge effort, which in and of itself could otherwise be considered a full-time job.

  2. Client work This is the time allocated to the client work that generates the bootstrap funding. Based on your cash flow needs, a target time allocation can be calculated. That target allocation can be minimized by minimizing the company’s running costs, which in most cases is dominated by salaries. It’s important to realize, though, that in practice the target allocation is not perfectly manageable. Clients’s effort and scheduling needs rarely align neatly with the objectives of the bootstrapping company. And since clients are paying you money, they have to come first in the priority chain.

  3. Fixed personal commitments This is the time required for fixed personal commitments. Filing tax returns, auto maintenance, family obligations fall into this category. These can be minimized by simplifying your life. For example, you could sell off any rental properties that require a lot of energy and overhead. These fixed commitments (and their scope for simplification) extend to financial obligations, since they affect the salary requirements. This component tends to grow with age, as young single people become married, start families, and collect the inevitable baggage life tends to add.

  4. Discretionary personal time This is free time, spent in activities like hobbies, social activities, reading, playing, vacations, leisurely weekends, etc. This is the part that can be hard to give up, especially when there are spouses or close friends affected. These activities also have financial implications.

What success tends looks like


p>Once you’ve reached your destination, and have built a successful company, the situation hopefully looks like this:

The business can be maintained (if a conscious effort is made to arrange it so), such that enough time is available for a healthy balance of fixed and discretionary personal time.

Life is good, and you can start to blog about your company’s “four-day week” policy.

The hard road to success

In my own experience, as well as that of every successful business owner I’ve known, success only comes after an extended period looking something like this:

It’s critical that enough time is consistently allocated to product work, so that continual progress is made, and at a level and pace sufficient to overcome the drag that leads to the loss of momentum, motivation and inspiration.

Here’s what this phase usually looks like:

  • The product effort is exceptionally big, as you’re having to do everything yourself—design, development, maintenance, support, and marketing.
  • The product effort has to be made, no matter what, in spite of disruptions from the dynamic nature of client needs.
  • The founders must simplify their lives, so that the personal fixed requirements are minimized.
  • The founders must minimize their personal and work expenses, minimizing the bootstrap funding, thereby minimizing the required client allocation.
  • The founders sacrifice much, if not all, of their discretionary free time.

This can be a difficult and challenging period, particularly on the personal and social relations of the founders. 85% of your life could be spent working—as effectively you’re running two distinct business, and having to do all aspects of both (and a good job, to boot!)

And if it feels like working to you, or if it’s unsupported by your spouse or close friends, then it can be very, very tough.

Having your cake, and eating it too—just doesn’t work

If you choose to start down this road, but can’t or won’t make the necessary sacrifices, then you can end up in a “no-man’s land” situation that looks like this:

In this situation:

  • Insufficient and inconsistent time is given to the work of the products, and as a consequence, enough progress isn’t made to get past the drag that kills momentum, inspiration and motivation. In the words of Jason Fried, “Inspiration has a half-life.”
  • You’re losing money, from the opportunity costs of what you otherwise could have earned in a situation of full-time client engagement.

It’s frustrating to be in no-man’s land. You still have the dream in mind, but you feel it, along with your momentum and motivation, slipping away, day by day.

Time for reflection

If you find yourself in no-man’s land, it’s important to recognize it, and deeply reflect on your objectives and priorities. You don’t want to stay there. If you’re not committed to the destination, it’s ultimately the road to nowhere.

Published inBusiness


  1. Very interesting, and sobering, take on what it means to run a bootstrapped startup. The pie charts will vary depending on age and commitment, so if you’re fresh out of college the pie charts will look a little more in your favor even if you still have some split in obligations in some aspects of your life (even worse if you have student loans). I can’t imagine how hard it would be to manage all that with a couple kids!

  2. Hey Matt,

    Just wanted to say that I completely and agree with the struggle you are writing about. I actually posted on the same topic today:

    Keep up the work! Greg

  3. August August

    Hi Matt,

    Impressive that you’ve hold on for 5 years until the company makes some profit. For me seems like forever to wait for 5 years for profit.

    Now I’m starting a bootstrapped company while doing regular job. The problem is that the regular job consumes 12 hours of my day and leaves me almost no time to dedicate to my company.

    I’ve read a lot of articles about startups in the web but yours seems the most realistic ones. Thanks for sharing it with us.

  4. Top-notch article. I’m very grateful for your insight into this scenario. I’ve felt this now and again over the years but was never able to properly articulate it (I don’t think I ever tried but there were times I wondered how to get my momentum back).

    Thank you, Matt.

  5. Thank you Matt! What resonated with me was the concept of minimizing opportunity lost. Really powerful stuff. Looking forward to the new book – Money for Something.

  6. I’m bad enough at managing – or being realistic about – my time, as it is. But I’m currently standing, with a couple of keen colleagues, on the precipice of this service-to-product transition so something has to break. It’s go/no-go time right now, I think it’s going to be a hell of a ride.

    Here’s to it…

  7. It is hard to add to the quality of the above comments, but I’ll say that this is one of the better pieces of insight I have yet come across. It’s one of those powerful enough to help one steer ahead more carefully or in a better direction — at least for me. Thank you for posting it.

  8. Hey Matt, great summarizing article and consistent with the startups I know. I wonder when (if ever) I will reach the destination scenario 😉

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