Don't Be Above the Job

Sometimes, an entrepreneur just has to go to work


I'm going to put an angel on one of your shoulders and a devil on the other. You'll have to figure out which is which.

I've been hearing this a lot lately: I want to be an entrepreneur but I have to put food on the table. Or pay off insane college debt. Or I'm starting a family.

First off, let me say I totally empathize. From where you are, this looks like cliff diving.

Then let me say, stop it. Do both.

Look, not a lot of people are going to tell you this and if it gets back to me I'm going to deny it and paint you as a filthy liar. Your word against mine. But yeah, go ahead and take a job or keep your job, and keep working on your idea.

Balancing a job and entrepreneurship is one of the hardest assignments you can take on in life. The stakes are high and it's not going to be the fun kind of made-for-TV startup experience. It's going to suck. It's going to be lonely and scary. It's going to be later nights and earlier mornings and slimmer chances and shorter runways than even your average entrepreneur complains about.

But if you're going to do it, you've got to do it. Now.

If you don't do it now, then when will you? When you retire? Let me tell you something, slick, you're not gonna be that limber.

A lot of startups have been spun out of career jobs that became day jobs that ultimately wound up the rear-view. In some ways, it's like getting a free head start, because most of the time, these entrepreneurs end up disrupting an industry they've been toiling away in for years.

But even when that's not the case, they have years of “this is not how I want to spend my career” lessons driving them on the business front, the operations front and the cultural front. But none of this is to say that the corporate world is inherently evil or bumbling or unworthy of your time. In fact, the corporate world and the startup world are symbiotic, and there are very good reasons for this.

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Random Five: Acronyms


Hey, look. I'm just trying to inject more humor into my blog and into your world. The main reason I'm doing this as a post, as opposed to just a tweet, is so that you'll comment below. Please do.

1. FOH
3. FML
5. WFH

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Random Five: Fifty Dollar Bill Suggestions


Hey, look. I'm just trying to inject more humor into my blog and into your world. The main reason I'm doing this as a post, as opposed to just a tweet, is so that you'll comment below. Please do.

1. David Lee Roth

2. John McClane

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Contrarian To a Fault

Nobody Calls It Playing Angel's Advocate


You know that stupid job interview question where the interviewer asks you what your biggest weakness is? It's a punchline at this point -- I've even asked it recently just to see the reaction I'd get from the candidate. I don't recommend this however, as it's neither as insightful or as funny as it looks on paper.

In the past, I'd always had an answer for this question, and it wasn't the standard:

• I work too hard.
• I'm a perfectionist.
• I care too much.

My answer was honest and ugly.

“I'm contrarian to a fault. That's not to say I disagree with everything anyone says. In fact, the opposite, I'm a swell team player. But if you push me in a direction I don't believe I should go, I will vehemently push back. Hard. Just because. Even if I know I'm going to lose.”

This answer was solid for three reasons:

1) I got to use the word “vehemently” correctly in a sentence.

2) There was rarely any follow up, because the interviewer was really just expecting me to choose one of the above BS answers so they could jump on it.

3) If the company I wanted to work for was worth working for, this was the right answer.

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Why I Suck At Investing


After the acquisitions of both ExitEvent and Automated Insights over the last couple years, my life has taken a few strange turns. Nothing earth-shattering and nothing I wasn't prepared for; Inbox fills up pretty quickly, lots more unsolicited contact, more people know how to pronounce my name.

That last one is nice, but it's always been pretty simple. Pro Tip: All the Os are long.

One recent turn that sort of threw me for a loop was when I sat down last week for an hour-long interview about my investment strategy.

Because I've never really thought about it.

Well, let me walk that back a bit. I'm not new to investing. I've been investing in my own endeavors since college, and in other companies for the last 10 or 12 years. There's just a lot more inbound now. And with inbound comes questions. My answers to these questions usually raise eyebrows, not because they're necessarily contrarian or zany, but because they're honest. And maybe because I always feel like I get asked the wrong questions when it comes to investment strategy.

Q: “How did you get started investing?”

A: “A rock band.”

So yeah, that just sounds stupid. But I've touched on this before. Forming a rock band is a very good startup learning experience. You put together a diversely-talented founding team, you spend a ton of time perfecting a product, and then when you're ready, you throw dollars on top of time and make a run at it. I did that sophomore year. Twice.

Towards the end of my college career, I started to apply the same concepts to other pursuits that were a little more based in reality. After college, I founded and funded two companies that went nowhere. Then I joined my first actual startup and got an idea of what the process actually looked like.

Total A-ha moment.

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A Sneak Preview of Teaching Startup

It's Time To Democratize Entrepreneurship


So I've got a new project, although “new” is kind of a misnomer. I came up with the idea for Teaching Startup at roughly the same time I came up with the idea for ExitEvent, back in 2009. I registered both domains within a week of each other, but ExitEvent had so much early momentum that Teaching Startup quickly made its way to the back burner.

I spent the next five years building ExitEvent and Automated Insights to acquisition. I sold ExitEvent in late 2013, and Automated Insights was acquired in early 2015.

So the time for Teaching Startup is now. This is not a startup and I'm not going anywhere. The website is bare-bones, the vibe is still very much evolving, and most of the talk is behind closed doors and will stay there for another few months. But if you're reading this, there are three things I'd really like from you right now, if you would oblige:

1) Join Teaching Startup as an early-adopter by getting on the mailing list. I'm not even going to start sending emails for a while, but you'll be in the front group.

2) Follow Teaching Startup on Twitter @TeachingStartup. This is where I'll update the progress as things come together over the next few months.

3) Like the Teaching Startup Facebook Page. This is where you'll be able to provide early feedback.

A little backstory — While I'm just about out of ExitEvent after a decent handoff and incredible growth on the part of American Underground, I'm still full-time building Automated Insights to the next level. We were acquired by a private equity firm and great things are expected of us. We're still a startup, for all intents and purposes. I've still got a lot of startup left to do, probably even more than before we were acquired.

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The Triangle In 10 Years: A SXSW Recap

Why Austin is Raleigh and Durham 10 years from now


Last week I was in Austin at South by Southwest, speaking about automation and the future of sports analysis on behalf of Automated Insights. Kind of a whirlwind trip—I got in Friday night and left Monday morning, not even taking advantage of my favorite South By, the music part.

I call SXSW Music my favorite part (and sometimes the “real” part) because it was my first experience with the festival way back in 2000, when digital was dial-up and interactive was creepy chat rooms.

It was back then when I first made a connection between Austin and the Triangle, and it held true on my most recent trip: Austin is Raleigh and Durham 10 years from now.

Back in 2000, it was a more generic “the Triangle,” before the individual identities of Raleigh and Durham as centers of commerce really took hold. And by that, I mean Raleigh was still trying to be Atlanta and Durham was just trying to figure out Durham, before American Anything or even the new ballpark.

But even back in 2000, and then again during a second trip to SXSW in 2009, and then this one in 2016, the connection wasn't hard to make. Austin is a great example of a city grown around tech and startup in a place that isn't Silicon Valley. It blends quality of life with a progressive, experimental attitude. It attracts young people without alienating families. And it's a really, really good place to start a company.

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Beware Startup Dark Mode

Blinders Can Kill You


Startup can be exhausting. It can seem like a grind. And in some ways it is. It's mentally and even physically demanding. But it isn't a treadmill, and this is where entrepreneurs should avoid making the mistake of slipping on blinders and tuning everything else out.

I see this a lot. I see founders and startup management teams get so locked into their growth hacking and two-week-sprints and launch dates that they fall into dark mode, ignoring everything and everyone in their path.

This is especially true with technical startups, mostly because dark mode is standard operating procedure for technical teams. In fact, most technical companies hire project managers, whose main job, if they're any good, is to keep everyone, including customers and company management, away from the developers.

So naturally, when a startup is so small and tightly linked, everyone starts to follow the devs down into dark mode. It's not quite stealth mode, it's more about isolation than secrecy, and when they get there everything outside of the next release just stops.

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Why Startup Isn't (Just) About the Money


Last night I finally got to meet Jason Gilmore.

This may not sound like a big deal to you, although it should, but it's a pretty big deal to me. Jason is a talented filmmaker, and our paths finally crossed because NBC paid for him to come out to SXSW and compete as one of five finalists in a short film contest. I was there, as I've said too many times already, to speak about robot sports analysis.

That's robot analysis of sports, not analysis of robot sports, which would be much cooler.

The real reason meeting Jason was a big deal, however, is because I've actually known him for about 15 years, and we've never met face to face. Yeah, I'm at the age now where I can probably say that about a lot of people, more than a handful. But Jason is special is because he played a big part in my first startup, Intrepid Media, which I founded in 1999 as the first social network for writers.

I talk about Intrepid a lot because you always talk about your first startup a lot. But it's more than that. While I wouldn't call Intrepid a disaster, it was indeed a failure, and technically, it was a failure of the worst kind. By that I mean I stuck with it for 13 years, watched it explode, make a good deal of money, and then flatline.

Intrepid was always profitable, from day one, because it was a good idea. No, it was a great idea. But it was my first startup, and I was green, and while I didn't make any massive mistakes, I just wasn't the entrepreneur to push it over the edge. It should have been Medium meets Goodreads meets Kobo.

But, make no mistake, Intrepid was a success, just not for the reasons I was expecting.

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Automation, Dystopia, and the 80-20 Rule

Why Computers Aren't Going To Rule Us All


On Saturday, I'll be giving a talk at South by Southwest on the Automated Future of Sports Analysis. As a preview, here's something that's not going to make it into my talk, which is cool, because I've got about three hours worth of material to cram into 30 minutes (plus 30 minutes Q&A). I cut this because it's something I can now just touch on. I don't have to explain it at length anymore.

In 2016, most people get that automated content -- narrative created by machines from data that reads and sounds exactly like a human wrote it -- is not going to replace the human writer anytime soon.

Automated content, otherwise known as natural language generation, is a science that I've helped pioneer and advance over the last six years. For the first three or four of those six years, almost every time we would be interviewed, the journalist would stop recording, go off the record, and ask how quickly we'd be putting them out of work. In some cases, the question was actually part of the interview, and in rare cases, there was an agenda behind the question.

However, most of the time the question came up because we were blowing people away with the quality of the content. There was nothing to nitpick. The stuff we write is informative, descriptive, efficient, and in some cases even entertaining. In all cases, it inarguably sounds human.

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So You Want To Sell Your Startup

How To Start Assessing Company Value


Every company I've started or been a part of has had acquisition interest at some point. Some of those acquisitions went through, some did not. Of those that did not, the potential acquirer killed it about half the time. In each situation, I learned something new about valuation and the transaction, and I can now tell you, empirically, that there is no standard for either.

But I've been able to distill a few ground rules.

Acquisition comes down to one basic but extremely difficult question: What the hell is this thing worth?

Sure, you're always engaging in speculation or back-of-the-napkin math. If you've made a run at seeking outside investment, you've probably done the research and come up with a number, one that you can write on a piece of paper, then fold that paper over once, then slide it across a rich mahogany desk.

But chances are that number, no matter how much discovery was put into it, is about as relevant at throwing a dart at a dartboard and multiplying by a million.

Or a billion, as long as we're dreaming.

Pricing and value, whether it be for a product, a service, or an entire company, is one of the most difficult determinations an entrepreneur has to make. Too many times, it's usually glossed over into a figure that “sounds fair.”

But to me, the Rules of Poker apply. You have to make sure that you don't scare away the other player while at the same time maximizing the value of your hand. Oh, and keep in mind you don't have enough chips to bluff. No matter what figure you throw out there, you're all in. This is not an easy trifecta to pull off, but if you don't check all three boxes you'll eventually lose.

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Why Other People's Rules Suck and What To Do About It


Entrepreneurs hate rules. Good entrepreneurs break them. Great entrepreneurs rewrite them.

I learned pretty early on to live by that code. And I should preface quickly here with the cautionary advice that this approach to life hasn't always worked out in my favor. I have a contrarian bent and a stubborn side that has probably kept me from hooking a few brass rings.

Not all rules suck. Most rules are good. There's this whole societal tipping point being kept in check by most of us adhering to a common agreement of not shitting all over each other to get ahead. But some rules are just stupid, and therein lies a lot of opportunity.

And a lot of heartbreak.

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Shmetiquette: Stop Bitching About Requests For Your Time


Not too long ago, my kids' school held a talent show, one in which my daughters were performing, so my attendance was mandatory. During the intermission, my 8-year-old son and I were walking around outside the hall, when a very pretty girl who had just performed a very well received song, smiled at my boy and said hello to him by name. She was definitely older than him, maybe 12 or 13, and a foot taller. He never looked up at her, but mumbled out a quick return hello as we walked past.

So naturally, a few steps out of earshot, I dove in.

“Who the heck was that?”

He was staring at his feet. “I don't know.”

“She knew you.”

Still staring. “A lot of people talk to me.”

Obviously, this is embarrassment and deflection coming from my still-baby-faced kid in the shadow of his old man, but it didn't make it any less funny.

That moment stuck with me, and now just about every time I get an unsolicited meeting request or introduction with no heads up, I think about my boy, and how that most awesome greeting from the way-out-of-his-league girl played a lot differently on his ego than it should have.

A lot of people talk to me, too. And usually it's not because of who I am so much as what they think I can do for them. This phenomenon, if you believe the conventional wisdom of the circles I run with, is actually somewhat of a plague.

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How To Start a Company With No Outside Investment

Here are the three ways I did it


I wear the customer-first badge. Proudly. I strongly believe raising money through customer sales is the best option, and in a lot of cases the only option.

In other words, I don't want to have to ignore a great startup idea because it isn't investable. I also believe that the vast majority of startup ideas aren't investable, at least not initially. They could be massive successes—they just shouldn't do it with VC money out of the gate.

That's not to say I don't believe in the VC model, far from it. I've been down that road half-a-dozen times now, and to be honest with you, it's been a totally different ride each time. And it's actually gotten better each time.

The most recent ride was (and is) with Automated Insights. We could not have done what we did and what we're doing without a capital infusion. But we were careful to do it the right way.

We were also very lucky, because while it's certainly clear that it's no longer impossible for an early-stage startup to raise VC in North Carolina, it is still highly improbable. And even when it happens, it usually happens when there are already customers, revenue and solid management in place—all of those things that make VC less necessary.

This is not the Valley, where you can go unicorn on a dream, if you're into that sort of thing.

So I'm customer-first, and you should be too. But as it is with a lot of entrepreneurial advice and punditry, everyone says customer first but no one actually tells you how to go customer first.

Thus, to right that wrong, here are the three ways I did it. These aren't the only ways, these are just the ones that worked for me, and I'm not going to advise you to do something I haven't already done.

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Winter Is Over

Time to Turn Dread Into Opportunity


A couple years ago, a fellow entrepreneur and I were lamenting the demands on our time, and how the big, important events in our lives tended to sneak up on us and catch us unprepared, because we were too busy keeping the plates spinning.

I get this. When you're an adult, you have to wing things. A lot of things. I'm down with that and I dig it. But that sage advice doesn't do much to alleviate the cold sweats when you've got a pitch tomorrow morning and you can't remember the talking points.

I hate that feeling more than anything in the world. It's the stuff of those nightmares when you get called on in class and you didn't hear the question. Plus you're naked.

It's not just work that suffers either. This conversation was in late January, I think 2013, and it came up that my friend had already slacked off on his New Year Get Back Into Shape Program. You know, the program we all map out on 12/31, ignore until the first or second weekend in January, then bail on before the end of the month.

So he asked how my New Year Get Back Into Shape Program was going and I told him I was actually cruising along quite nicely. In fact, I was almost done with it.

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