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Bootstrapper: Origins

Oct 18, 2016 | Financing Your Company

bootstrapper-origins “A bootstrapper isn’t a particular demographic or even a certain financial situation. Instead, it’s a state of mind.” — Seth Godin

I see all sorts of articles aimed at entrepreneurs who, for one reason or another, are not seeking venture capital and want to build their small businesses from the ground up. These articles are great resources and provide various ideas for apps and software to help turn a profit. We’ll explore technology for business again eventually, but this week we’ll explore the bootstrapper’s origin and mentality.

A Class By Themselves

Once someone’s gone into business for themselves, I’ve found that they operate in one of the two most popular ways to pursue their passions:

  • By taking on freelance or side work while working a day job,


  • By quitting their day job and going all in for themselves, by themselves.

And oftentimes one scenario can transition into the other.  

The “musts” for even a modicum of success are determination, basic knowledge, essential programs, the ability to carve out the time and coffee. Sure, it’s nice to have a cheer squad behind you to provide emotional or even physical support, but I’ve also seen people decide to become entrepreneurs after they were told they “couldn’t do it.” As long as you have the bare essentials to accomplish the work and the bare knuckle determination to get that work done, you can begin attracting clients and customers.  

Prepare For The Long Haul

Brinen & Associates originated from a bootstrapper’s dream.  Unlike some famous real estate moguls-turned-presidential candidates, I didn’t get a million-dollar loan to start my business from my daddy.  

My first solo attempt occurred during my off-hours about 13 years ago. By day I was a mild-mannered tax attorney. By night I was focusing on estates and estate planning. It took me two years of what some would consider “failure” to solidify my first client.  As you can imagine, I fought off a lot of doubt about trying to build a business while also trying to maintain a personal life and full-time job. It is not a one-size-fits-all endeavor. Several times over, I’ve seen that owners willing to make sacrifices are the ones that experience success.  

An Important Rule: No Poaching

As I built my clientele, I made it a point to never, ever steal clients from my employer. My loyalty to my employer at the time was absolute and lasted until the end of the business day. Then, I was operating on my own steam. Love them or hate them, employers are providing the revenue stream that helps you can keep the lights on during those late nights when you’re working on your own career.

I’ve seen how karma treats folks who steal.  

Who’s The Best Fit?

This isn’t a rule so much as an observation: The best candidates for bootstrapper-entrepreneurs are the ones with companies that are not capital intensive. These are people who can operate their businesses with a phone, laptop, some notepads and a coffee table.  

Sure, there are some exceptions to this: There are people who can brew beer in a bathtub after they come home from a long day as a desk jockey. But when those microbrewers are ready to expand out of their bathrooms or garages, they need space and the equipment. With those needs come some major outside funding.

When your needs are few and can fit inside a couple of computer bags, then you’ve got mobility – and that is priceless. I have a friend who is a salesman by day and also operates an online business selling custom and personalized baseballs for babies. There’s no overhead — it’s e-commerce — and he simply has to place orders with some import/export companies for raw materials. He’ll ship his orders on workday lunch breaks or Saturdays, whichever is more convenient.

Small business offices are becoming a thing of yesteryear, while temporary modern work spaces like WeWork can provide the organized, professional settings you need during public-facing and/or busy times.

It’s admirable, scary, exciting and even sometimes boring to create a business without venture capital or significant financial backing. Brinen & Associates was built this way and has helped several other small businesses get a similar start in the modern marketplace. Contact us to discuss your needs and plans for your small business.


Forming Your Company

Financing Your Company

Operating Your Company

Growing Your Company

Defending Your Company


Transactional and Corporate Law

Mergers and Acquisitions


I formerly worked as a satellite employee from my home state of New Jersey. I ended my employment with my former employer in 2016. In 2018, I was sued by my former employer for $1.1 million in Illinois State Court. I was referred to Brinen & Associates, LLC by a friend who is a client of the firm. Brinen & Associates, LLC came highly recommended. I contacted Joshua Brinen and then had a consultation at his office with his colleague Mark White. Together, Messrs. Brinen and White explained my options...

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