The long and lonesome journey of solo entrepreneurship



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[Above: I’m jealous of this on so many levels. Photo credit: a6u571n on Flickr (Creative Commons)]

I don’t tell anybody where I am going. I just go. Just me, a rental car and a gym bag full of clothes. And snacks.

Man. Seems like it was just yesterday.

November, 2008.

I am 24 years old.

I am working on a three-week job in Tucson, Arizona, when the three-day holiday weekend comes. Everyone gets to go home and go see their loved ones, etc. I’m single so I have no one to go home to…I decide to stay put in Tucson and enjoy the nice weather.

Only I don’t stay in Tucson…

On Saturday morning, I do a little research, hop in the car and go. I don’t tell anybody where I am going. I just go. Just me, a rental car and a gym bag full of clothes. And snacks.

Who can forget the snacks.

I make my way up north. If you’re unfamiliar with Tucson, it is at the very bottom of Arizona so this is a LONG drive up to the top. Beautiful weather throughout though. As day turns to night, I make my way through Flagstaff and, after coming close to hitting a deer that comes out of nowhere, I safely end up at my destination.

The Grand Canyon.

I spend the entire day on Sunday just walking around in awe. More than a few times, I sit and contemplate things. What life means. What happiness means. Things like that. I just sit there. And inhale fresh air. All by myself. Over and over again. I am incredibly happy.

I vow not to return for a decade or so. That is how special this day is to me. I don’t want to tarnish it by making it some kind of bi-annual Disneyland type of vacation spot.


I don’t pass another test after that…and I lose my job during the summer because I suck at it. It just isn’t for me. Plain and simple.

But I think building a website is…or might be.

Over time, while with this company, I slowly build Beernews organically but it is incredibly tough. The job itself is a bear, especially during “busy season.” I am going for my certification and spending way too many hours in books from which I have no interest learning anything. Every night, I arrive home from work or finish studying by 10 or 11 and hope to squeeze in an hour or two in which I can put together a couple blog posts.

One night during busy season in February, 2009, I crack under the stress of this schedule. The site is starting to take off, I am trying to pass certification exams and work is godawful. I tell my brother that I might put up a note on the site and take a month off from it. He tells me not to because I have a really good thing going and people won’t come back. I will lose what I have built.

So I follow his advice and juggle all three “jobs” so to speak.

I don’t pass another test after that…and I lose my job during the summer because I suck at it. It just isn’t for me. Plain and simple.

But I think building a website is…or might be.


I’m just toiling away. Day after day, I watch the sun set in the distance through this oak tree outside my window. Another day of life gone by. And another one. And another one.

When we are children, we start out way down the path of this golden road that those before us have paved. We don’t even realize it. Some go off of it in adolescence and who knows where they land. Some probably go on to do amazing things. Or maybe not. The rest of us? We behave, fall in line, get good grades, go to college, and follow the herd. We stay on this path in autopilot.

I never questioned why I was on that path until I went off of it.

The summer of 2009 is actually awesome because it is a breather from the stress. I move during the fall into an apartment near a couple of my best friends.

I then toil in what is something probably resembling depression for the better part of the next year. I don’t want to go back into anything similar to the previous work environment. Yet Beernews is nowhere near close to making money.

When I’m not casually looking into jobs, I try to teach myself to program because I want to turn Beernews into something big. I study PHP and learn how to read it (somewhat) but struggle with writing it from scratch. I eventually decide to look for developers to help me out.

This turns into a long and costly process. I work with probably no less than 30 developers on these little projects. They are just ideas. Some more ambitious than others.

But I have no clue what I’m doing at this stage.

The calendar turns to summer of 2010. I’m still in that same apartment. I’m just toiling away. Day after day, I watch the sun set in the distance through this oak tree outside my window.

Another day of life gone by. And another one. And another one. I imagine people partying at the beach and going to cookouts and all that. Time just passes. Without any progress. Really. On a personal or professional level. It is without a doubt the hardest time in my life. Long and lonely days, man. Sad days.

I really have no idea whether my friends are aware of the downward spiral at this point. They are there for me. They keep me company at night which is critical.

Somehow, I’m only motivated to work harder to dig myself out of this rut. I have put all my eggs into Beernews at this point and there is no turning back.

I finally hire a developer that I feel I can trust and away we go.

I’m not sure when exactly but one day it hits me like a ton of bricks that I am an entrepreneur. Probably the combo of learning about new startups and realizing that a human being is depending on me to keep paying him so that he can eat and stuff. Because of this, the next several months are a solid (and somewhat enjoyable) learning experience. I no longer feel like I’m completely alone even if I am in terms of equity. I am still struggling in some ways but at least I feel like I have a purpose each and every day.

Several months pass after this epiphany before another problem comes up. Well, two of them.

My developer quits. And then I run out of money.

It’s April, 2011.

I decide to finally throw some Google Ads on Beernews while I figure out how I’m going to start making actual money from this thing I’ve spent over three years building.

I receive an email saying the site doesn’t have the same “streamlined look” it once did.

Thanks, bud.

It feels great to make even a few hundred dollars that first month after making nothing for the first three-plus years.

The developer quitting turns out to be a blessing because the time I would normally spend working with him goes into building up the business side of Beernews. And that business is growing.


I burned through some cash and wasted a lot of time but I came out a much better person than I was heading into those four years.

January, 2012.

I am now 27.

Since May, I’ve been making money on Beernews and it’s pretty much at a point now where I can count on the equivalent of an entry-level salary every month. It is growing and will only get better from here. While I’d say I’m far from being “made,” I would say that I have “made it.”

Like when Tom Hanks finally gets past that huge tide in Castaway.

I’ve since taken up more development work myself and learned how to do a fraction of the things that I hired all those developers to do. I must be smarter now than I was in 2009! I am making the occasional phone call and working with a bunch of advertisers. I’m still writing fresh content every day and doing a lot of content curation.

More importantly, I started living again this past summer.

Living. Yeah. That.

I started running and ran the equivalent of a half marathon one night in September, for example.

I actually go out a lot now, too, though I still spend long days at home working on Beernews. I still miss the collaborative work environment quite a bit.

This is the first time I can remember sitting down and reflecting on the big picture since…well, probably…

The Canyon.

Beernews turns four years old on February 29th.

I’ve learned a lot since that first post. I burned through some cash and wasted a lot of time but I came out a much better person than I was heading into those four years. I don’t take a dollar for granted the same way I did when I had a consistent paycheck coming every two weeks. I have a much better appreciation now for how human beings provide value to one another and reward each other. And I got a better education than I ever did in college and it was a hell of a lot cheaper, too.


Every day, I engage with people who comment on my work right after I finish it. I am making immediate connections with people who benefit from what I do and it rules.

Here are a few lessons (or realizations) that I’ve taken away from the experience with respect to entrepreneurship and even life, in general.

1 – It is a miracle that I am alive.

And according to the CDC, I only have around 78 years to celebrate this miracle (or now about 50 years to go). There is no guarantee that I will even make it that long. How am I best taking advantage of this miracle? I am working my ass off while I’m young, hungry and foolish. Setting a foundation on which I hope to be living very comfortably within the next few years. One on which I can potentially raise a family in several years. By the time I’m 30, I want to consider whatever work that I’m doing at the time to be 100% play. And I want to travel A LOT over the next few years.

[Edit: I'm using the term miracle to describe my overall existence, in general. It isn't meant to imply I almost died at any point. Also, this doesn't mean retirement! And running a website gives me the flexibility to live in different places. I don't mean travelling to sound like a vacation. Though I haven't taken one of those in several years.]

The first phase of conquering life is figuring out what you want to get out of it so start there.

2 – I’m doing what makes me happy.

…Or…at least working comfortably so that I’m not dreading each day. I don’t consider what I do to be “work” as much as I will admit I spend a lot of time doing “it,” however you want to categorize “it.” In order to discover what made me happy for work, I didn’t drop my old job…I spent an hour or two every night exploring what I thought could be a new one. I’m not 100% happy sitting at a computer for as long as I do each day though I’m on the right track.

3 – I believe in Maslow’s Hierarchy of Needs.

I suspect that a lot of entrepreneurs spend a disproportionate amount of time trying to fulfill the top of the pyramid when the lower tiers are crumbling beneath it. It is definitely possible for some to go top down but you need to spread your time out between self-actualization and your personal life. Spend time with family and loved ones. Do the dating thing. Be in a relationship. Have fun. Live. Laugh.

Don’t skip over those personal layers. Can’t stress that enough.

4 – Work-life balance is essential for personal AND business relationships.

You have to take good care of yourself to be able to take care of others. It is great to “live for others” and be charitable, etc. You have to be a little selfish sometimes though. This goes for health, relationships…you name it. Work-life balance is a fancy buzzword that gets thrown around but there is a lot of truth to it. Your employer (or you if you are a self-motivated workaholic) isn’t going to create that balance for you. YOU HAVE TO STEP BACK AND TAKE THE INITIATIVE TO DO IT YOURSELF.

It will help you in the workplace, too.

5 – Support from friends and family is not the same as support from people who have walked in my shoes.

We need both types of support. Period.

6 – I would never do the solo entrepreneurship thing again nor would I ever advise anyone else to do it.

You need a partner to keep you in check on your ideas and progress. If you must go that route, network with other entrepreneurs and hold weekly meetings where you set goals that you have to meet, etc. Don’t go completely solo. DON’T!

7 – Education in entrepreneurship is valuable.

Just like you would have a hard time accounting without an accounting degree, there is a science to being an effective entrepreneur. I had never heard of minimum viable product until late 2010. I wish I had back in 2009. I would have saved a ton of time and money.

8 – Research is important for pinpointing where the best opportunities are in the marketplace.

I started Beernews because I wanted a reliable source of beer information so the customer I have today (a.k.a. a reader of the site) is essentially the same as me, just four years ago. I experienced the pain point firsthand back then. So, for me, it was easy to see the opportunities. If you are a serial entrepreneur that doesn’t necessarily live and breath the thing you’re trying to fix, that is tougher.

I did do a lot of research as well before starting Beernews. I subscribed to RSS feeds and learned as much as I could for several months before starting the site.

9 – Never give up.

If you have the guts and drive to try and start a business, there is something special about you. You are making (or are going to make) big sacrifices in order to gain freedom and live a unique way of life. You are willing to work hard upfront to maximize your happiness for the longhaul.

Kudos to you. Seriously.

Is it not working out so far? Consult with everyone and everybody. Experts, customers and so on. Maybe you can pivot. Maybe you can fundraise. Maybe you need to go back to work and get more experience and make more cash. And work on your startup at night.

Do what you have to do but don’t give up!

10 – People have served as better resources than whatever else I was using at the time.

You would be amazed how much of a difference that a single phone call may make in your life. Network with people. Pick up the phone. Write an email. Send a tweet. It’s easy.

11 – Direct feedback from the people I am serving/helping feels awesome.

I used to work behind a desk for a company that served companies that served companies and individuals. I had no sight to that last tier of people. The end-users. The people that actually benefited from my work. I never met them or had a clue how useful my work was to them. Or if they even looked at. It sucked.

Every day, I engage with people who comment on my work right after I finish it. I am making immediate connections with people who benefit from what I do and it rules.

12 – The world seems a lot smaller to me now.

I never felt “accomplished” before becoming an entrepreneur. Even when I was working at a big company, making good money, I didn’t. For example, I looked at a company like CNN as this giant machine that was so much bigger and badder than other media sites. Now I realize that CNN is just a wheel with thousands of cogs called people. People like me that wake up in the morning, eat breakfast, drink coffee and then punch the keyboard mercilessly for the rest of the day (or whatever it is that you do). It just isn’t as a glamorous news source to me as it once was now that I realize that anyone with the chops can do just as good a job reporting on a subject.

And the thing with these big wheels like CNN is that they are incredibly inefficient and vulnerable to super cogs called entrepreneurs. We’re seeing that unfold before our eyes. Not to pick on CNN, just an example.

13 – It is less about the things I do or consume and more about the company I keep.

I’m no longer a snob. Or try to be one. I don’t go out of my way to buy Budweiser or go to MacDonalds but I can enjoy a Bud Light if that is what we have in the fridge and I’m spending my time with good people.

14 – I appreciate that I am a constantly developing and dynamic individual.

Knowing “who I am” is less about pigeonholing myself as a thing (like an entrepreneur) and more about accepting that who I am today is very different from who I will be in three years or who I was three years ago. I just try to be very open-minded about new experiences and trying new things.

15 – Sharing my experiences is an important element of my personal growth.

Like what I’m doing now…

16 – I don’t think there is anything I can’t do in this life now.

There is probably more than that but I’ll stop there!


Ah, the Canyon.

Someday, I’m going to get back and when I do, hopefully I’ll have someone by my side. Hell, maybe a family, too. Inhaling that fresh air again. Reflecting on life the way I am now and the way I did in November, 2008…

…that or I’ll be too preoccupied watching a little one and making sure they don’t fall off a cliff.

It is a journey of journeys.

Don’t try or pretend to live every day like it is your last.

Don’t expect to enjoy each and every moment going forward.

Just figure out what you have to do to be able to enjoy as many of those moments in your life as you possibly can.