Photo Credit: Chez Andre on Flickr.

Entrepreneurial Priorities if You Don’t Want to Despise Yourself at Age 80

With the exception of a general, “We’re hiring” post a few days ago, my site has been largely neglected for the past year. It’s not that I don’t want to write. I do. And it’s not like I don’t have things to say because, if you know me, I do. I really do. And it’s not even that what I’d like to say isn’t all that important…. because it generally is.

I feel the need to write today, however, because it directly relates to why I don’t write as much as I used to. And it directly relates to why I, in the eyes of the typical startup founder or venture capitalist, am not a great entrepreneur. In their eyes. I’ll admit that I’m a terrible day to day running a business guy. I’m a terrible “take care of the basics” like health care and witholding taxes” guy. I’m actually a pretty decent entrepreneur though. Put me on the phone with a prospective client, and I can speak their language and close a deal. At the end of the day, being an entrepreneur is all about making money so you can live to play another day.

Or is it?

It’s also about life and lifestyle.

I feel really compelled to write about this because, though I sorta took a mental break from the tech startup world for a bit while I focused on my job and my new life back in on the east coast (and, you know, survival and keeping a roof over my head), I’ve dipped my toes back into the water.  I am as alarmed today as I was two years ago about the entrepreneurial scam that is peddled by basically everyone.

There’s an entrepreneurial scam?

Funny you should ask! Yes. And it goes something like this: “If you’re not willing to give 24/7 to build your startup or company, you shouldn’t be an entrepreneur”.

Jason Calacanis, famously, said in one of his listserv emails on September 27, 2008, eight days after the market crash of September 19, 2008 and two days after the FDIC seized Washington Mutual Bank, that the sign of someone (paraphrasing here) worth being hired/invested in in the startup world is the person who will gladly come in on Sunday. This was the actual passage from that email:

Hold an optional off-site breakfast meeting on a Sunday and see who shows up: If folks don’t show up for you to grow/save the company on a Sunday for a two hour breakfast, they probably aren’t going to step up when the sh#$%t really hits the fan. You need to know who the real killers on your team are and you need to get close with them now. Again, it’s fine to have 9-5ers on your team–if you’re the Post Office. You can’t have them at a startup company. Note: if you reading this and saying I’m anti-family, save it. Folks don’t have to work at startups and some of the hardest working folks I’ve met have families and figure out how to balance things.

UGH. So much wrong with this sentiment. This sentiment screams, “I am what I do” and that is simply the most self-loathing sentiment you can have. It is neither something to be proud of nor is it healthy mentally or physically. I have a lot of respect for entrepreneurs who will go to the Farmer’s Market on Sunday morning. Or who take their kids to the park. Or who go to brunch with their husband/wife/girlfriend/boyfriend. Not so much for the person who opts to work instead of doing these things.

Here’s what that mentality of roughly 2003-2008 got me. It got me a career, yes. It also got me a divorce and years of my life I will never get back. At nearly 38 years of age, that is a lot to bypass in the service of the almighty dollar, ego, prestige and “fame” (whatever the fuck that means).

While I worked my corporate 9-5, I was coming home and then working another 8 hours on client works, building a company or other nonsense. I neglected my son (who fortunately still loves me to death) and my wife, at the time, by working every night until 3am just to pass out exhausted and wake up at 6:30am to go to work again.

Those lost opportunities to be present were squandered because I bought into the charade that if I work longer and harder, I’ll succeed more and have a better life. Rubbish, hogwash, nyet, NO!

After my ex-wife and I split, I naturally did some soul-searching. Work wasn’t our only problem. But I’d say it was a contributing factor to all the problems I could see. I decided to do a 30-day “work cleanse”… For 30 days, work normal business hours – 9-5, 10-6, whatever… and then put my work down and find something to do to occupy my time. That was a hard thing to do since my work was my identity and my habit. However, after 30 days, I realized I was feeling more energized. I got more sleep. This enabled me to focus better on my work when I was doing it. It helped me get things done faster. I felt more alive.

By and large, this 30 day drill has become my lifestyle now six years later. I typically still work Monday through Friday, 9 to 5. I avoid after hours work or weekend work if I can help it. Though I still take side work, one project at a time in digestible portions, because… a little extra cash every month is nice. But, today, I spend time with my girlfriend, cook dinner sometimes, and do stuff that is fulfilling to my life (usually!) instead of investing all my energy into something that will ultimately fade away.

My greatest fear is that, in my latter years, I will look back on my life with regret, building something that doesn’t last while sacrificing the things that really matter on the altar of snake oil salesmen. You are not what you do. Your time spent does not define your character.

In the words of Trent Reznor Johnny Cash, three months before his wife’s death and seven months before his own:

What have I become 
My sweetest friend 
Everyone I know goes away 
In the end 
And you could have it all 
My empire of dirt 
I will let you down 
I will make you hurt

I Fired Myself

If we’re friends on Facebook or Twitter, you know about my new job in Baltimore. Technically, it’s not a new job yet, as I don’t start until February 4. However, it’s a new job and a return, for the first time since 2006, to a more corporate (if laid back) working environment. I’ve only worked for one company in that period of time, and I was a founder. That, of course, is the hugely successful WP Engine. However, I left that role in October of 2011. I still didn’t have the motivation to not work for myself.

A little about this new role, however, since I brought it up. I feel it’s necessary in proving the point I want to make.

Corporate Culture

Agora Financial, as a division of Agora, Inc. was named the 2nd best place to work in Baltimore in 2011 by the Baltimore Sun. As an adopted Austinite, that label carries a high standard. In Austin, “business casual” is cutoff jean shorts (“jorts”) and a tech swag tee shirt with sandals. In Austin, the chic commuter rides a scooter or bicycle. Maybe even walks. In Austin, drinking a beer is not something simply saved for off-hours. In fact, many companies keep a refrigerator stocked with beer because, hey, the workforce can be more relaxed, efficient and productive if given certain leeway. Thankfully, none of us are drunks… maybe.

At Agora, I found a company that matched this sort of comfort level I’ve come to expect. When I flew up for an interview (and job interviews have been something I’ve not really had to do seriously since 2002), I emailed Mark, the Art Director and my point of contact, and very politely suggested I wouldn’t be arriving at their headquarters in a tie. Manage expectations, and such. Mark’s response was simply, “That’s fine. Business casual works”.

Business casual can mean many things. It’s sort of a catch all phrase that means different things to different people based on different companies policy ideas. So I wore some decent dress pants, a button up shirt and a vest with no tie. The team had sandals, jeans with holes, and hoodies and plaid-pattern button up shirts. I felt like I was in Austin!

Ideology

But company culture was just one aspect. The work they do perfectly fits who I am practically and ideologically.

You see, Agora is a publishing company first and foremost. I’m a publisher. I’ve written a book and worked with traditional book publishers. My first startup was a publishing company with, at our peak, 350 blogs. Agora’s model is different than those models, but they’re publishing. They are creating content that, hopefully, long outlives us.

They are a policy research publishing company. Those who know me know that I love policy, I hate politics. When I engage in politics, it’s usually from the lens of policy. Agora provides research analysis and white papers based on their policy research in a subscription format. So there’s also a revenue model. And they’ve been highly successful at doing this, historically through newsletters, for years. It’s a proven model, and they are a proven company.

In addition, their policy analysis generally comes from a libertarian (small “l”) perspective. As a left-leaning small-l libertarian, I enjoy this aspect of what they do (even though I suspect most of my colleagues and most libertarians as a whole are right-leaning small-l libertarians, I suspect that we all agree on a framework of responsibility and limited government in individuals life, and diverge on other less-important minutiae).

I was hungry for this job. It was a dream job for me. Join a company doing things I loved, in areas I loved, with tools (WordPress) I loved, with a style of corporate culture that I loved. When they made me an offer, I didn’t hesitate to accept and fire myself from my own company.

I fired myself!

Having the Balls to Fire Myself

Most people aspire to stop working for the man, and start working for themselves. There are entire classes at universities and colleges about entrepreneurship, and to be sure, entrepreneurship is the mode of decade.

The other night, I had the opportunity to guest lecture for an capstone course on digital entrepreneurship for American University. It was online and you can hear my story and lecture here. This course is a culmination of all the classwork done in this program and is largely a practicum of everything learned to that point. The lectures are a series of lectures from guests that give the students inspiration and motivation about their futures while they work on their individual projects.

During this talk, I spoke specifically about the time I left corporate America and went out on a limb. It was 2006. I had been working on a side-project basis for over a year building up a WordPress-powered content network and when we finally took funding, I was employee #1 or #2, depending on who you ask. I couldn’t wait to leave my computer-fixing job and go do something I really, really wanted to do instead and get paid for.

I’ve heard stories like that from hundreds of entrepreneurs. Most never look back with any regret, despite the struggles and sometime-economic instability.

I have a view that whatever I do, I do it because I want to. It’s very easy to look and say that running a startup, building a product, starting a company or, in general, working for yourself is, in fact, the holy grail.

From Happiness to Happiness

My view is that the holy grail should be happiness and motivation derived from what you do. Sometimes that means taking a more unorthodox step and saying, you know what… being an entrepreneur is awesome, but it’s a vehicle to happiness, not happiness itself.

So effective February 4, 2013, Aaron Brazell has been terminated by Aaron Brazell.

I don’t know if I would have fired myself to go be a developer in some developer-happy company that segregates the developer from the product line. In other words, a lot of developer-oriented companies have developers as a means to an end. Product managers go talk to customers, develop goals, milestones, wireframes or storyboards, make decisions on initiatives with corporate executives and the developers exist to make that shit happen.

Some people like that. Some people don’t want to be a part of the politics and roadmapping. They work better with a framework that defines what their role and deliverables are. For them, that’s happiness.

For me, happiness is seeing the vision, talking about what it means – the pros, cons, feedback – iterating, being a part of the process of both scoping and building and then allowing the idea to flourish. It means building something toward an end. In the idea of a startup, it means building a product and moving it toward acquisition, IPO or even failure.

As a consultant, there was no viable end. Unless I’m committed to building out a team (I’m not), increasing a production pipeline (without a team, I can’t), or other such motivations, a consultancy looks exactly the way it does in 10 years as it did on day 1 – find clients, build something for them, collect money, wash, rinse, repeat. There’s no glorious ending. To me, that makes for an unhappy Aaron.

Agora provides an exciting platform, an an innate sense of entrepreneurship internally, that makes me happy. If I have an idea, I can try it. If I think something could really work well, I’ve got a green light to work on it. All within a good developer situation where I also have deliverables, and things to look at and solve. The combination of such makes Aaron a very happy person.

What Makes a Community?

I normally write articles that carry a bit of authority. I usually write what I know about and have a high degree of confidence writing. I don’t write often because I want what I do write to carry authority and be hard-hitting.

This is not really one of those articles.

I haven’t done what people like Alex Hillman has done in creating collaborative working environments for independent entrepreneurs at Independent’s Hall in Philadelphia.

I haven’t been an organizer and champion of city-wide entrepreneurship like Josh Baer has in Austin.

I haven’t fostered a product community like they have over at StudioPress with the Genesis Framework.

What I have done is work within the context of a thriving WordPress community of developers, users, consultants and advocates.

I have lived in a city that has made it’s name on entrepreneurship and arts in Austin.

I have helped and supported entrepreneurs in their quest to build products in DC and find ways of succeeding both with and without investment money.

Moving Back to Baltimore

For some weeks now, I’ve made it clear that I’ve decided to move back from Austin to Baltimore. In 2008, I left Baltimore because I saw awesome things developing in technology in DC. At the time, there were guys like Peter Corbett who was just beginning to do technology advocacy work in the Nation’s Capital. By 2009, iStrategyLabs would launch the first Apps for Democracy contest that challenged contestants to create web and mobile applications with civic intent. That would morph into similar contest like Apps for America, etc.

You would also see some organizations that would flare out dramatically because of business model, ideas, weak leadership, lack of community involvement, etc.

I would then move to Austin where I would see a city immersed in technology. Lots of money flowing. Lots of incubator action, such as the products and entrepreneurs who would be graduated from the Capital Factory incubator. I would see ATX Startup Crawl occur several times a year as guests would have the opportunity to move around town and visit some of the great startups like TabbedOut, InfoChimps, uShip and more. Thousands of people would come through these offices and see the great technologies and ideas being built, all while enjoying local Texas beers and eats.

I would see awesome projects like We Are Austin Tech highlight influencers in that community (including myself) come up.

And I watched Baltimore grow as a technology community to the point where DC entrepreneurs started paying attention to their up and coming little brother 45 mins up I-95. I watched from afar as Dave Troy would put his heart and soul into building Baltimore as a center of entrepreneurship and tech. I’d watch as Greg Cangialosi would build his Blue Sky Factory marketing firm out and have a successful acquisition, all while continuing to personally invest more in the Baltimore scene.

I even watched great tragedies like the systematic destruction of Advertising.com by Aol.

I watched this all over the last 4 years and realized Baltimore was coming into it’s own. It had successes. It had failures. It had investors. It had bootstrap. It’s still not entirely cohesive, but from my seat, it looks promising.

So I’ve decided to move back to my home and put my money where my mouth is and see if I can take what I’ve gleaned from DC and Austin and apply it here in Baltimore. I may be one of those failures. Or I may not be, but I’ve got to try.

What Makes a Successful Community?

In the last few weeks, I’ve had several conversations with Baltimore business owners and entrepreneurs, and I’m finding a common question and point of discussion: What makes a successful community? The answers and opinions are intriguing. Again, I can’t say my opinion carries any authority. What I can say, however, is I’ve been in a bunch of communities and witnessed elements of success.

Some folks think a successful business community requires investors who are willing to commit their time and money. Anyone who has gone through the fundraising process knows that hands on investors are the best kind. If a VC or Angel investor can help a portfolio company supplement resources (human capital or otherwise) through their network, they bring quite a bit of upside to a startup. Investors who wire money and never pay attention to their portfolio companies, expecting the founders to execute according to plan, are in my opinion bad investors.

So in this light, some entrepreneurs here in Baltimore find the lack of investment money or engaged investors as detrimental to the community.

On the flip side of the coin, some entrepreneurs seem to be thinking that the mark of a good startup community is going to be in the number of entrepreneurs who are able to successfully bootstrap. There is some validity to this claim as well. The more you can do on your own, the less of your company you’re giving away (as I noted in the “Valleyboys” segment of this article a few weeks ago).

However, there is also value in bootstrapping and taking money, if the situation is right.

Other folks I’ve talked to feels the value is in the number of people attend professional meetups compounded by the sheer number of meetups. In Austin, we have a vibrant meetup community. From the Austin WordPress meetup to Austin on Rails to Austin Lean Startup to Refresh Austin and the list goes on.

My opinion is that a city startup community is built on all these things. It’s not money, really. Money will follow success. Perhaps Baltimore needs to have an IPO or high profile acquisition that allows the company to continue to operate and hire in Baltimore to put them on the map and in the conversation. I don’t really think it’s that, per se, but that certainly helps.

It would help if the State of Maryland was more business-friendly to small businesses, as Texas is. People come to Texas, and more specifically Austin, from California and New York because the environment is notably friendly to small business. More business would be created in Maryland with better business policy. It might even attract out of state growth.

Beyond that though, meetups are important but meetups don’t create value if the conversations end at the meetup. The idea of building something – a prototype – as you might get out of a Startup Weekend is good… if it continues afterwards from prototype to business product.

But I think the biggest thing that makes community grow is collaboration and the willing to share ideas without being defensive, sharing resources without being possessive, sharing physical space without being prohibitive. It takes more that an entrepreneurs flying solo behind his Macbook Pro in a coffee shop, but it takes less than structured office space with prohibitive managerial org charts.

It doesn’t take sacrificing lifestyle on the altar of work, but it does take entrepreneurs willing to gut out ideas by working with other entrepreneurs and customers and transparently sharing war stories of success and failure while helping to mentor others new to the space.

It does takes the karmaic “pay it forward” approach without fiefdoms and regional rivalries to ensure that a rising tide raises all ships. What you put in to other companies you have no direct stake in, but can help with informal advice (when solicited) makes for a circle of life that encourages a community to exceed expectations and move from one level to the next. Mentorship is not an ROI term, but it is critical to the ecosystem.

Am I off-base in my thinking here?