People have been asking me for a long time to write more on business topics, entrepreneurship, SaaS products, and running a consultancy. My writing is typically technical in nature, so this is a chance for me to write about the other intellectual area of my life: Getting people to pay me to do things for them.

I don’t have a grand plan for converting you all into buyers of my upcoming ebook (it doesn’t exist) or get you to sign up for my slick A/B tested drip campaign, er I mean mailing list for special early access to my “Be Awesome in 32 Hours” masterclass. Geez, maybe I suck at this “business stuff” after all?

I’m going to do this by borrowing a format Felix Denis used in his book “How to get Rich”. Before you involuntarily wince at that title, it’s an amazing anti-self-help book. It’s not a prescription or plan, just a humorous autobiography of sorts on how he got rich. Which incidentally wasn’t from selling get rich quick books.

So while I feel the advice I will be giving in these posts is solid. It is just how I did things.

This looks historic right?

A bit of history

I was raised by entrepreneurs. My father was a lawyer with his own small firm. My maternal grandparents owned a farm and a couple of Hallmark Card stores. My paternal grandparents were professional classical musicians and private music teachers. One uncle was super scrappy and owned a barrage of different endeavors over his years. And other more distant family members also owned businesses with varying degrees of success.

Maybe raised isn’t the right word. I was down right marinated in it growing up.

Working for yourself or owning a company wasn’t a foreign concept to me. I literally grew up in and around it, which I will readily admit is probably not your situation. I started off without any of the mental blocks around entrepreneurship I hear about from others.

I had always assumed I would be self-employed or start a company… at some point.

The problem was I was always fairly happy at my job. I worked at the World Company which was a private small to medium-sized media company. They owned several newspapers, a TV station, printed several other newspapers/magazines, and had one of the most innovate and successful small cable systems in the world.

Here in little old Lawrence, KS we were the second city in the US to have cable modems (1996), an early adopter of online news, early alpha testers of the DOCSIS standard, Video on Demand, and VOIP phones and went on to create and release Django to name a few things.

While my title and responsibilities at the company changed over time the best way to explain my role was as an internal technology consultant. Sure there were systems I spent more time “in charge of” than others (the ISP related systems), but it was a pretty rare week where I didn’t get pulled into some entirely unrelated meeting with another business unit to help smooth out some technology hurdle.

This experience proved to be the best graduate course in technology consulting ever.

I was always challenged, rarely bored, and compensated fairly well. So when Silicon Valley came calling it was, maybe to their surprise, a difficult sell.

Red phone seemed appropriate for how nuclear that conference call was…

That all changed with a single meeting…

Ok, I’m totally lying. It had been a stressful quarter and a crappy week. That meeting was just the last straw that put me into action.

I remember everything about that meeting. My usually awesome boss wasn’t so awesome dealing with the usually awful vendor who was particularly awful that day. I’m going to withhold most of the details to protect the innocent, i.e. my old boss who I still consider a friend and respect. That vendor can go fuck himself.

So what did I do? I ranted so well you would have thought Aaron Sorkin wrote it, dropped the mic, and walked out never to return right?

Bzzzt wrong answer. That would make for a much better story. They’ll never make a movie about my life, but if they do I hope Sorkin takes creative license to put that in.

What really happened

I went out with my best friend and commiserated about exactly how much our jobs sucked and how we should totally go out on our own.

Then I woke up hungover. And then I got laser focused on getting out on my own. I blocked out time in my schedule. I committed to it. I gave myself a year but managed to do it in just 10 months.

So how did I get ready? If you’re going to run your own business you have to be comfortable juggling several things at once, so I did most of these in some version of parallel:

Read every recommended book on business, sales and marketing I could get my hands on. Everything Seth Godin had written to date. If it was business related and on a Top 10 list around 2005–2007 I probably read it. I’ll put together a reading recommendation list in a future post.

Paid off my little bit of credit card debt.

Paid off my car loan.

Refinanced my house at a lower interest rate and for a longer term.

Spent more time helping in the Open Source communities I was a part of.

Wrote more blog posts.

Networking (the human to human, non-BGP kind).

Increased my savings as much as possible.

Increased my nights/weekends contract work.

You’ll notice a lack of the usual suspects. I didn’t mention a camping retreat to ideate with my spiritual advisor, a pitch deck, startup networking events, finding an office, trademark law, “crushing it”, or writing my business plan.

Small rant: Business plans are total bullshit. They aren’t worth the bits used to store the document. Don’t misunderstand me, you should have a plan. You should have thought deeply about all aspects of your business from acquiring customers, what choices you’ll face at various stages of growth, when you’ll hire, what might go wrong, to what sort of work you will and will not perform. Planning and thinking through situations are very important.

However, focusing on the layout and formatting of this “plan” based on some rule book you found at the library is a waste of time. It’s busy work of the worst kind. It eats up a bunch of time and has the added detriment of being utterly worthless.

If you find yourself reaching for a “business plan template”, just stop. No one is ever going to read it. Stressing over the wording and layout is just that, stress. Nothing more.

The Learning

Being a technical guy, I had all of the geek aspects of my business handled. I needed to round myself more, so I spent all of my time that I might normally spend on playing with the latest tech and devoted it to marketing and sales research.

The conventional advice is to increase your knowledge and experience in areas that you excel in and farm out all work related to areas you aren’t great at. I understand the sentiment but have to disagree. At various points in my life I’ve devoted considerable effort to improving in areas I wasn’t naturally interested or gifted in and it has paid HUGE dividends.

If you are, on a scale of 1 to 10, a big fat zero at sales because you’re an introverted geek reading a couple of books on the subject can quickly take you to a 2 or 3. With a bit more work you can be in the 4 to 6 range without having to make sales your new hobby. Getting into the 8 to 10 range typically requires a lifetime, but isn’t that true of nearly everything in life?

Back to my point. Working for yourself, you end up wearing a bunch of hats, not completely sucking at them is a good thing. The really tricky part is to take them off at the right time and give them to someone new.

Assuming you’re moderately successful, you can start paying others to do these things for you at some point. So having some knowledge of the area is both useful in the short term as you get off the ground, but also in the long term as you now have to evaluate the next firm or person who will take over that hat for you. You did know you’re your own HR department too right?

The Financials

You may have noticed my financial items above weren’t the usual startup fare and look the part of a personal financial planning session. As you get started YOUR finances ARE the business’ finances.

I paid off or restructured all debt to reduce my hard monthly costs. I don’t remember the exact numbers, but let’s assume my non-optional (house/car/utilities/food) expenses were $2k/month and I wrangled it down to $1k/month over the course of my “get ready” year.

What did this do for me? This exactly doubled the runway of every dollar I made or saved for this upcoming journey. It’s old advice from Ben Franklin, but a penny saved is a penny earned.

Don’t get me wrong, I saved money in a good old fashioned savings account as well.

Financially this doubled my chances of being successful. Emotionally it greatly reduced my stress levels. Combine the two and this advice is the most important bit in this whole article.

You’ve heard “Cash is King” and it is. Working for yourself or running your own company is about one thing and one thing only, cash flow. Everything else is bullshit around the periphery.

So decrease your expenses and increase your savings as much as possible.

For those of you paying attention there are a ton of things NOT in my financial list:

No office

Absence of a $10–15k budget for branding or positioning

Lack of reams of fancy letterhead, envelopes, and business cards

No assistant (virtual or otherwise)

New home office furniture

Didn’t pre-order a bunch of swag

I didn’t get an office until @jacobian talked me into it about 1.5 years after I went on my own. Even then it was a small modest office. I also got a new desk earlier this year, after 8 years of being in business. Previously I was using the desk my grandmother got me for my first real computer back in the late 90s. It was black, functional, and fine.

The Networking

Geeks are often introverted and believe “networking” is hard or takes some special skills. It’s pretty easy, takes little effort, and you’re already probably doing it.

Writing a blog post on your favorite tech topic? That’s networking. Contributing a bug fix or mailing list post in OSS? That’s networking. Doing more contract work on nights and weekends? Touching base with former coworkers or friends? Drinks at the bar during a conference? Yep, that’s all networking.

All of these activities increase the chances of finding new work, new customers, or referrals. The more you put yourself out there, the more chances you have for a positive connection. Not to get too mathematical on you, but it’s basically lottery like probabilities. Buy one ticket? Small chances. Buy 100 tickets? Still small chances individually, but now you’ve got 100 of them.

The more touch points (aka tickets) you have out there the more likely you are to succeed.

Doing It

After doing all of the above for about 10 months, I started having to turn down side work as I simply didn’t have enough time to take on some of the projects that were coming my way. The third time I got an offer for a 100+ hour project, I took it.

I simply explained that I was booked for the next 2 weeks, but could begin then and signed the contract. The next day I put in my notice at the day job.

Why three? Three proved it wasn’t a fluke. If work of that size walked in the door with minimal effort, having the time to actually focus on getting work would make it rain. I’d be rich in 9–12 months, right?

Wrong, that contract went belly up in 3 weeks. You’re saying to yourself, “But Frank, it’s a contract you’re covered anyway so no biggie”. Extra super double-wrong. Sure I could have sued the company and probably won. Spending $18k in legal fees on a $20k contract and get paid in… oh… about 24–36 months.

Nice idea, but as I found out the promise of future minuscule legal success apparently doesn’t work as legal tender at the grocery store. Go figure!

Lucky I had that savings and cut down my expenses, right? Damn straight it was, otherwise my little foray into self-employment might have lasted a whole month! Instead with 6 months of expenses in the bank and half the expenses I used to have I had some breathing room to find some new clients.

A couple of weeks later I landed an even bigger client. And then a few smaller ones and I was off on this now 11+ year adventure.

More?

Did you enjoy or find this useful? Please reach out to me and if so I’ll write more on these topics. If you have a specific topic in mind even better!

Or if you want to just keep in touch I’m @fwiles on Twitter or you can learn more about my company REVSYS if you’re in need of serious technical help.