Why “Against the Wind” by Bob Seger is a Perfect Analogy of my Life as an Entrepreneur

I’ve been an “entrepreneur” for a very long time. If you want to count shoveling snow for dollars when I was a kid, or my brief stint trying to start a baseball card shop with my cousin when I was 11, then I’ve been doing this for well over 25 years. By the time I was a sophomore in college, I had already experimented with everything from Amway to selling computers using classified ads. I even tried investing in a psychic hotline, so yeah, I’ve tried quite a bit. It wasn’t until I started my first web design business from my college dorm room that I really found my passion.

Since then I’ve been involved in more web projects and products than I can remember. I’ve owned and bootstrapped a web development firm with several employees, raised seed and venture money for web startups, built products that have succeeded and products that have failed. The other day I found myself telling someone my “entrepreneurial” life story. I went through all of my successes, challenges, and failures. It was both exhilarating and depressing at the same time.

The next day I was shuffling my playlist on my iPhone and “Against the Wind” by Bob Seger and the Silver Bullet Band came on. This is by far one of my favorite songs (and if you’ve never heard it, do yourself a favor and go listen to it; you can thank me later). As I was listening, and re-playing my previous conversation in my head, it became incredibly clear just how much this song could be my theme song as an entrepreneur, and maybe yours too.

It seems like yesterday
But it was long ago

So, yes, it’s hard to believe that so much time has passed since I created my first website, but I find this to be typical of everything I work on. Rome wasn’t built in a day, and neither will your business, product, program, or sales funnel. I often find myself working for long stretches only to look up and realize that I’ve been heads down for six months or more. Sure, lots of things happen in between that time, but everything takes time. It often goes by a lot faster than I’d like.

Janey was lovely, she was the queen of my nights
There in the darkness with the radio playing low

Janey was my mistress, that is, she was the idea or project that I spent my nights and weekends with. I would get so obsessed with Janey (whatever it was at the the time), that I would literally spend all my time with her, especially late into the night, in the darkness, coding away, listening to Green Day and Nirvana.

And the secrets that we shared
The mountains that we moved

I learned more from doing than I’ve ever learned in a book. Someone can tell you how something should work, or what system to use, or how something should be done, but you most likely won’t listen to them. Until you get your hands dirty and do something yourself, you’ll never truly learn the secrets, and that’s not necessarily a bad thing. Actually building something, instead of just thinking about them, is another incredibly powerful notion. Did I move mountains with the products and projects that I worked on? Probably not as much as I would like to think they did, which leads us to the next line…

Caught like a wildfire out of control
Till there was nothing left to burn and nothing left to prove

Naïveté, yep, I was filled with it. I was 22 years old and I was out there telling experienced business owners how to run their companies. I was using my limited worldview (centered entirely around web development, SEO, and online marketing) as the basis of my expertise. I knew little to nothing about running a business or what customers actually wanted, all I knew was what seemed to be working for a handful of other clients and online business. I thought I knew everything, and I wasn’t afraid to tell people about it. I got lucky quite a bit, and my clients had plenty of success, but I made the mistake of confusing knowledge with wisdom, the latter only coming with years of experience, trial, and error.

And I remember what she said to me
How she swore that it never would end

I had some good times back then. I had some great clients. I even got to work on some very cool projects. But this line is about commitments, and the harsh reality that every entrepreneur will face when things don’t quite play out the way you we’re led to believe they would. Whether it’s the project that grows out of scope and the client stiffs you, or the product you spend 6 months building for a partner that is supposed to resell it for you and never does, promises will get broken, and you will get hurt. People may say to you, “Hey, it’s just business.” But as an entrepreneur with a small team, it’s hard not to take things personally.

I remember how she held me oh so tight
Wish I didn’t know now what I didn’t know then

Ignorance is bliss, or so they say. I remember when I was young and idealistic. I gave people the benefit of the doubt. Oftentimes a simple handshake was good enough for me to kick off a small project for someone. I wasn’t a complete idiot, I had contracts in place for development projects, web hosting, and employee agreements. But even with those in place I got screwed, a lot. I had multiple contract designers who used unlicensed images that came back to bite me years later, I had to take a subcontractor to small claims court just to recoup a fraction of what I paid him, and several times I needed my attorney to threaten lawsuits to have people honor their contracts. These experiences have all made me highly skeptical, and I don’t particularly like it. They changed my worldview and how I size up people now. Unfortunately it’s hard to forget what it’s like to get burned.

Against the wind
We were runnin’ against the wind
We were young and strong, we were runnin’
Against the wind

The life of an entrepreneur will always be an uphill battle. Someone will always seem to have more money, more momentum, and more experience than you. It can be frustrating and demotivating. You will constantly fight market forces and there will almost certainly be someone with the upper hand. But when we’re young, we push on because we’re strong, idealistic, and frankly, we don’t know any better. That’s what I did.

And the years rolled slowly past
And I found myself alone

Not to get too dark here, but the longer I ran my web development company, the more I started to hate it. Everyday seemed the same and we couldn’t break through the plateau. I was the sole owner, so while I had plenty of friends, family, and employees to talk to about “the future”, nobody was as tapped into the business as I was. My life, my career, and my purpose, were all wrapped up in the success or failure of this business. It was lonely.

Surrounded by strangers I thought were my friends
I found myself further and further from my home

What about joining a mastermind group? I did. I even had some mentors that were very helpful. In the end, though, I found much of the advice to be self-serving and not as useful as I would have hoped. The best piece of advice I got was that I needed to spend my time working on the business instead of in the business. This was incredibly tough for me. I was the best programmer we had. If I stepped away to grow the business then what would happen to our programming projects? I decided to try, and I got way out of my comfort zone.

And I guess I lost my way
There were oh so many roads

I started to take advice from a lot of people instead of trusting my instincts. I wanted to grow the business, though, so I started spending more of my time selling. When I landed some good size jobs, I decided to hire a sales guy. I also hired another contract programmer for the overflow work. I eventually took on a minority partner to add a broader range of marketing services to our repertoire. I thought I knew what I was doing, I was following everyone else’s advice.

I was living to run and running to live
Never worried about paying or even how much I owed

If you’ve never had to make payroll, then you can’t possibly imagine what it’s like. Sure, we had some good months, but there is a big difference between billing clients and having the cash in your bank account. I was working 70 hours a week. I was chasing down payments. I was trying to work on the business. I was cleaning up slack from developers. I was working on products to increase recurring income. When we were short on cash, we used our credit line. When the cash came in, we’d pay it back IF we didn’t have something else due. But I was growing the business. And to make money, you need to spend money, right? I tried not to think about it. I tried to keep the business growing and my employees paid.

Moving eight miles a minute for months at a time
Breaking all of the rules that would bend

It seemed like it was non-stop. And then 2008 came (and a few other surprises). I thought I felt lonely before. It was even worse now. Every two weeks the cash needed to be there for payroll. Every month there were payments to Dell leases, rent, bandwidth at our co-location facility, oh, and don’t forget health insurance. We started to run out of buffer space. The credit lines were creeping up. I would often have to take a cash advance on a personal credit card just to cover a bill here and there. We would delay payments on things as long as we could. I was past the point of no return. Closing up shop would have left me holding the ball. I felt completely trapped by my business, and I didn’t want to use the nuclear option (shh, don’t say the B-word).

I began to find myself searchin’
Searchin’ for shelter again and again

I started looking for other options. I had owned this business for almost 12 years. It was hard to imagine my life without it. It was part of me. But I had no choice. It was time to move one.

Against the wind
A little something against the wind
I found myself seeking shelter against the wind

I had two options, either shut everything down and work the rest of my life as an indentured servant to pay off the company’s debts, or negotiate my way out of it. Part of the reason why bankruptcy was never an option for me is because I couldn’t fathom the idea of not paying my bills. Then I had the pleasure of meeting with a banker/investor who explained to me the inner workings and risk calculations of business loans by big banks. At some point we all need to cut our losses, and this is true of banks as well. If I declared bankruptcy, then the bank would most likely have gotten nothing. However, if we negotiated a settlement, then at least they would get something. Plus the bank has already assumed that several of these loans would default, so they’ve built that into their earning calculations. They weren’t being hurt by this, but it could have killed me. So that’s what I did. I negotiated reasonable (and I do mean reasonable) settlements with all of my creditors, sold off my hosting and development clients, and liquidated unneeded equipment. It took awhile, and a lot of work, but I was able to finally move without any major issues.

Well those drifters days are past me now
I’ve got so much more to think about

I decided to go back to what I knew best and what I felt I was best at: building web products. So as I was winding down my web development business, I started to lay the groundwork for my next company, a social website for new parents. The two big differences here were that I was seeking seed funding to build it and I hired a CEO to run the company so I could focus on the technology and the product. I had a family, a wife and two kids. I had to think about the future and find a way to generate consistent income.

Deadlines and commitments
What to leave in, what to leave out

I worked on that new company for about 4 years. My team built an amazing product. Unfortunately we couldn’t get the traction or the next round of funding, but the experience and expertise I gained helped me land my next job as the VP of Product/Technology at a funded startup. So, yeah, I’ve got a lot of commitments and deadlines to worry about. I’ve got a mortgage and car payments. My kids are expensive, but worth every penny. I have to make a lot of decisions, and my decisions have consequences. But I feel like I have more control now than I did when I was young and jumping onto whatever the next shiny things was. And I know why now: because I know what to leave in, and what to leave out. I’ve learned what’s important, and what’s not. I’ve gained a tremendous amount of wisdom.

Against the wind
I’m still runnin’ against the wind
I’m older now but still running
Against the wind
Well I’m older now and still running
Against the wind

But I’m still an entrepreneur. When the ride I’m on ends, I’ll buy another ticket and move on to the next adventure. Sure, I’m older now, and being an entrepreneur is still an uphill battle, but I’m still running. I can’t imagine life any other way.


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2 thoughts on “Why “Against the Wind” by Bob Seger is a Perfect Analogy of my Life as an Entrepreneur”

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