Running a Small Business - I never knew it would be this hard

Written by on Jul 11 2013
Running A Small Business

I can’t count how many entrepreneurs I’ve heard say, “Being a small business owner is hard.” What the hell does that mean? Really? I’m going to break down my struggles.

Running a small business with a business partner

No one warned me a business partnership (especially a 50/50 split) is like a marriage. Our personal struggles become each other’s burdens. When one of us is hurting, the other feels that pain. Our most important conversations are the ones where we don’t talk about business. I’ve realized my business partner is the person I turn to when I need to be pumped up from a bad mood, and I wouldn’t have it any other way.

Running a small business and having 3 “jobs”.

For the past five years, LessEverything has designed and built web apps for other people. During our “spare time,” we’ve built our own apps (Accounting Software, Time Tracking for Freelancers, and Project Management Software) and hosted several conferences and workshops. This “spare time” is found between paid client projects, at night while your family is sleeping, or first thing in the very early morning. These stolen moments are put towards our long-term goal of being a product company that generates revenue from the things we create.

Bootstrapping a Small Business

The Bootstrapping Dilemma

Bootstrapping sounds so honorable, so scrappy. Truth is, you’ll launch your product and it will just sit there, while you’ll be super busy with clients–the clients that pay your bills. Now if you’re lucky, your app’s users will be screaming out for new features and improvements. You’ll be dying to iterate on your product, but you’ll have a line of clients ready to pay you BIG bucks to work on their products.

At one point, LessEverything was billing at $120k a month for our consulting services. Awesome, right? We trimmed back our consulting work so we could work on LessAccounting, even though it was making $7k a month at the same time.

Bootstrapper’s Envy

You’ll become friends with people in the same stage you are in business. Some of your friends will make a choice to get funding, and they’ll raise millions of dollars. You’ll be happy for them but you’ll be working with no budget, and they’ll be traveling and spending money. You’ll be jealous of them, and question if you’re doing the right thing.

Marketing our products

When you’re absolutely slammed with “real” work, marketing your products will become the last priority. In reality, marketing is the most important factor in your success. Now remember that because you’re bootstrapping, you have no money to pay for advertising. You have no money because you’re working 20-30 hours per week on client projects and giving the spare time to building your product, so where’s the time to market? And actually, what is marketing? I like designing apps. So good luck with marketing.

Articles On Marketing

Having a family & running a small business

My wife and kids are the most important things in my life. Thinking about them can bring me to tears. Then why I am I writing this blog post on a Saturday morning while my kids are in the living room playing and laughing? Why am I choosing to write this over playing with them? Prepare yourself for feeling like you’re slighting someone with your time and attention. If you’re bootstrapping your company you will have little free time, and your time will be divided (work, family, and friends). I’m a shitty friend and I have no hobbies. I have to force myself to take time to walk around my neighborhood for 20 minutes a day.

So yes, “Being a business owner is hard.” Being a business owner is accepting a self-doubt. I do realize everyone has self-doubt but running a company is accepting a new, larger buried of self-doubt.

It’s living with the feeling that you’re about to screw it all up and sink the company over a stupid decision but not allowing that fear to paralyze you.

Running a small business is not a choice for me.

I could fill this paragraph with cliches, telling you that I want to be my own boss, I want to make a lot of money, I want to do things my way. But the truth is I don’t know any better. I grew up in an entrepreneurial family and if I wasn’t building LessEverything with Steve, I would be iterating on marketing, design, pricing and process with my Dad at our family car washes. I’m an entrepreneur because it’s in my DNA.


Hi I'm Allan,

I wrote the article you're reading... I'm one of the co-founders of LessEverything. I love my family more than breathing and I love creating videos about our family adventures.

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