The Highs & Lows of Bootstrapping

“Bootstrapping is the only way to keep your company yours. You appreciate each little win that much more, and every stumble stings a bit more.”

So says Richard Hull, co-founder and CEO of, in response to Jason Fried’s Inc Magazine article on “How to Get Good at Making Money”.

As someone who now has successfully launched two businesses with no outside funding, I attest to Hull’s sentiments. Building something from the ground up takes courage, it takes guts, and it’s risky. The fear of failure, of not making any money, of having an idea crash and burn – it’s what keeps so many people thinking about entrepreneurship instead of actually taking the leap and making things happen.

Knowing that the time and money invested, from the very beginning, is your own, also naturally connects you that much more with every aspect of your business. In another recent Fried article on, Jason talks about hiring their first assistant at 37 Signals, and how difficult it was even to give up the smallest of tasks.

Why? Because from the very beginning, Fried had been involved in (literally) every business decision, down to what brand of toilet paper belonged in the bathroom. And while it’s important to let go, anyone who’s started their own business can attest to Fried’s following statement:

“I understand that it’s silly to believe that every small decision needs to run through you. But it’s such a primal instinct when your business is your own baby”.

On the contrary, every stumble hurts that much more – every client you don’t land stings a little bit, leaving you wondering, “What could I have done better to have earned the business”?

It’s this rush, both the highs and the lows, that may terrify me, but also excite and motivate me to do great things. It’s incredibly empowering to know that you’ve conceived of an idea and have been able to turn that idea into something that people will pay for.

I still get nervous hitting the SEND button when emailing a proposal to a client. My heart still races before stepping on stage to speak at an event. It’s not because I lack confidence, it’s because I care (a lot) about what I do and I take pride in everything I’m a part of. My work matters to me, just as it should to you.

And if it doesn’t matter, it’s time to stop doing it.

At the end of the day, the question isn’t whether or not you should seek an investor for your startup, and it isn’t a question of whether or not you should start your own business.

At the end of the day, it’s finding a career that ignites this similar passion and excitement within you. Whether it’s bagging groceries or running a Fortune 500 company. If you don’t feel personally invested – if you don’t get excited by your successes and a little hurt when you miss the mark, somethings missing.

And once you discover what does excite you, inspire you, motivate you, and maybe even scare you a little – hold on to it as tight as you can. Because regardless of pay or benefits, loving what you do is all you could ever ask for and more in a job description.

(Photo credit)

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8 Responses
  • Jason Mollica Reply

    Once again your posts send another jolt into my brain to do what you have done/continue to do. Thanks again for your wisdom as always, bud.nJason

    • Matt Cheuvront Reply

      Thanks as always, @twitter-21574752:disqus – It’s an ongoing adventure, that’s for sure!

  • C.J. Adams Reply

    Great post, Matt! It goes along very well with Sam’s “Scratch Your Itch” post from a few days ago.

    • Matt Cheuvront Reply

      Thanks, @twitter-21690425:disqus Loved Sam’s recent “Scratch Your Itch” post.

  • Purple Panda Reply

    Yes! Still trying to get my freelancing (business?) under the way. Thanks for the inspiration! n

    • Matt Cheuvront Reply

      If there’s ever anything I can do to help or if you just want someone to bounce ideas off of, don’t hesitate to let me know!

  • Cameron Plommer Reply

    I agree with you when you say stop doing work that doesn’t inspire you.nnI also thinks it’s the job of management to create such an environment. As an individual there is only so much you can do to make any job enjoyable. nnBut managers have the real power and can make the lives of their employees so much better by making simple tweaks.

    • Matt Cheuvront Reply

      Agreed – managers do have the ability to shape a culture that encourages staff to be involved and personally invested. Allowing for creative freedom instead of micro-managing.

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