This is everything I've written here or elsewhere over the last few years. You can search, filter by publication, or choose from some highlights below.
HIGHLIGHTS

How to Find a Mentor

Everyone Should Have At Least One

8.3.15


Last week, I wrote this very well-received article for ExitEvent about how any startup community needs a deep bench of mentors. While that was my main point, I also got into what makes a mentor great and how to go about choosing one.

I made it clear that a great startup mentor doesn't necessarily have to have one or more large exits. They just need to have experience with -- and passion for -- what you're trying to do.

Their main goal is to impart to you what they did to get to where they got.

I got mostly these two questions back:

1. Can you mentor me? (Appreciate the thought, but no, I've got a few right now)

2. How do I go about finding a great mentor for me? (Uhhhh…)

Good question.

Here you go.

Now, I'm not talking about JUST startup mentoring here, I'm talking about success in any discipline. Yes, that mostly follows a startup or small business or career theme, because those are what you most need mentors for.

You want to get in great shape? You need a book and/or the Internets. You don't need a mentor for that. If you have to have one, they charge about $50 an hour at your local gym. I don't recommend that, but whatever is going to get you off the couch. It's your money.

So this is about finding the right person to advise you on getting your business or your career or your life's passion in order. And for that last one, I'm not talking about your personal life. For that, you need a whole other thing. I like the church, but that's me. I went to Catholic school.

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Teaching Startup Debuts Episode 1 of The Show

Bringing Startup to Everyone

1.10.17


Yesterday, my side/giveback project Teaching Startup debuted the first episode of The Show, an online TV series dedicated to bringing the concepts of startup and entrepreneurship to a broader audience by making it more accessible.





It's been a long time coming. And we're pretty hyped about the results, even though we know we have a long way to go.

On The Show, we talk about startup without droning on about startup. Sure, we talk about startup, in fact, we do that a lot, and you'll definitely learn something. But we also talk about stuff that's far more interesting.

Pop culture? Of course. We don't do our jobs 24/7. Neither should you.

Sports? Yeah, look at us. It's in our DNA.

Parenting? No better way to learn about being an entrepreneur.

Humor? If you're not laughing, we're not doing our job.

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Want To Win? Learn to Hate Losing

8.6.15


As I'm writing this, I'm sitting in a casino hotel room having come back up from losing a ton of money in just a couple hours. I feel like crap. If you were my friend I'd call you right now and whine for an hour.

But there's nothing I can do about it. My friends are all downstairs having a great time. Some are winning, some are losing. Nobody wants to hear my freaking sob story, and at this point, I'm the cooler. So I'm upstairs pounding away at my keyboard in hopes of turning this rage into something useful for you.

Consider this a very expensive article. But you deserve it.

I definitely don't have a gambling problem. In fact, I have the opposite of a gambling problem. I have risk aversion. I love numbers and I play the odds. I count cards in blackjack. I play the pass line and the come line in craps. I never touch roulette, slot machines, or basically anything else in the casino where there's a big house edge.

When I'm winning, I'm on top of the world, and I walk away up almost every time. When I'm down, which usually happens when I start losing right away and can't get even, I hate myself, I blame myself, and when my pre-determined stake for that session is gone, I walk away and go upstairs to sulk for a few hours.

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The Art Of Getting Acquired

8.13.15


Look, I'm not going to come right out swinging and make some kind of grand proclamation on this, but I think it might be time for the Triangle, or for that matter any startup hub that isn't Silicon Valley, to start seriously taking a look at acquisition as a legitimate exit from day one.

I know what some of the blowback is going to be from this modest proposal. Something along the lines of acquisition being a cop-out which ultimately hurts the startup community and the very idea of entrepreneurism itself.

I get that. Purism. Rock on.

But that's a view you get when you look at acquisition as a by-product of entrepreneurism and not as what it should be—a goal.

Not THE goal, but A goal.

If you never think about acquisition, you naively limit your options to either going public or creating a lifestyle company. Don't get me wrong. Both of those are valid paths. I've walked both several times.

But here, there and everywhere that isn't the Valley, the amount of money you need to raise to get to the public markets is nearly impossible to scrape together. Further, valuations are reaching astronomical levels, with Valley unicorns, those companies landing $1 billion-plus investments at multi-billion dollar valuations—Uber, AirBnB, Pinterest, SnapChat, etc.—increasing at an alarming rate.

How the hell do you get out? I'm not a wizard. I can't do that kind of math.

Let's settle down a bit and take the ridiculous out of the equation. The path to going public is still fraught with danger. It's unbelievably hard to get to $1 million in revenue. It's much, much harder to get to $10 million and nearly impossible to get to $100 million. Nevertheless, it's a good goal. It's a much better goal if capital is nearby, cheap and easy—or if you have a track record of big, successful exits.

What are two things we lack here, Alex?

read the rest at: http://exitevent.com/article/the-art-of-getting-acquired-150813


The Ballad Of the Company Man

Startup Is For Everyone, So Why Doesn't Everyone Think So

9.15.15


Last Wednesday, I was at the outdoor patio of a local bar in the middle of our area's startup hub, enjoying a few beers with an entrepreneur I'm advising. Kind of ground zero for startup talk.

We were preparing for his second fundraising cycle, so we were slinging around startupy terms, but after a couple beers and playing off the excitement we were both feeling around what he was building, the conversation became less numeric and more fun.

That's when the dude two stools over spoke up.

“Hey, I don't mean to be eavesdropping on your conversation, but I just want to say the way you guys are talking is pretty cool. I wish I was a part of something like that.”

Or it was something close to that (beers). My first reaction was kind of a warm glow -- that guy just made my day. Then my annoying side kicked in and I responded.

“So… Why aren't you a part of something like that?”

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How To Make Great Decisions

Step 1: Everything Is An Experiment

9.8.15


One of the most difficult skills for anyone to get their head around, let alone master, is solid decision making. But it's one of the key elements for success in any pursuit. Some skills you can fake, like leadership (not kidding, you can fake this all the way up to the end). Others you can farm out, like coding.

Decision making? You've got to have it, and you've got to be good at it. No, you've got to be great at it. It's one of the few metrics that directly correlates to success, where you can look back on your decisions and, to dumb it down completely, if you made nine good decisions out of 10, you're probably at 90% of where you want to be.

Probably. There are caveats to everything.

The problem is there's no good way to learn, practice, or measure the process of making good decisions. It's not something you can read in a book to learn (uh-oh), complete a series of exercises or quizzes to practice, and there's no scale by which you can quantitatively measure the results.

Although I could create that. The Procopio Decision Matrix. You got a Q out of 13! I'm calling the patent on that right now.

In all seriousness, the most difficult part of decision making is being honest with the criteria and honest with the post-mortem. We rarely tell the truth to ourselves and about ourselves at either end. No one likes to admit that fear and emotion play a huge part in the criteria, and no one likes to dwell on their failures. It's not even healthy to do that.

Then there's the question of what makes a good decision a good decision in the first place. There are all kinds of conventional philosophical cautionary tales here -- “Damned if you do, damned if you don't,” “Rock and a hard place,” “Should I stay or should I go,” and “If you choose not to decide, you still have made a choice.”

If that last one sounds vaguely familiar, it's because it's the only discernable or memorable lyric from Rush's Freewill, and it's probably copped from Ayn Rand or Camus or something very deep and intellectual.

But take a breath. It's not as convoluted as it sounds. There are maybe five or six steps to consider when you want to make good decisions. Those include identifying and mitigating all the little risks, defining success and failure and at which point you should throw in the towel, and learning to live with and recover from failure.

However, the first step is by far the most important. It's also how you get started, so I want to focus directly on that.

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What Two Exits In 15 Months Has Taught Me

There's No Such Thing As Luck in Startup

2.16.15


Almost five years ago, I walked into Robbie Allen's brand new office in a horrible mood.

Robbie and I had been meeting regularly at various Starbucks across the Triangle, and we had recently started discussing whether or not it was possible to automate content for websites for each of the NCAA Men's Basketball programs, based on nothing more than StatSheet data. I loved these meetings. They were about automation, artificial intelligence, technology, writing, and sports – basically how I built my career mixed with how I spent my free time.

Robbie noticed my mood immediately. So I explained, with much animation, that I had just come from probably the worst meeting of my life –- a meeting that was supposed to have been about finalizing the funding of a project that I had been working on for close to a year.

Instead, what actually happened was an unbelievably bizarre rejection, and four months of free work, planning, and negotiation had just vaporized.

Needless to say, I was now in shock and without funding. It wasn't the first time. The technology product firm I had founded just a couple years prior was doing over $1 million in revenue, and it had taken a lot of “No” to get there.

But this time I was furious, mostly at myself. A lot of trust went into that deal, and I got burned. Badly. In fact, I had turned down a lucrative consulting contract so I could work personally on this product, which was one I truly believed in.

Robbie listened patiently to all my rage and then told me that he had been thinking more and more about automated content, and he thought we should get started.

My mood shifted instantly. “Give me the weekend to come up with a design,” I said.

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How Much Should I Get Paid to Work At a Startup?

When To Go All In and When to Walk Away

1.11.16


One of the toughest questions I get about startup happens to also be one that I get the most often.

“How much of a pay cut should I expect to go to work for a startup?”

I got that very question again last week, from someone I had just met. I could tell within a few minutes of meeting her that she was sharp. She had the talent, she had the drive, and she had enough sense to be asking the right questions.

It wasn't her fault that this particular question has no right answer. She just didn't know that there was no right answer. A lot of people don't know that there is no right answer.

So of course I'm going to answer it. I wouldn't be me if I didn't try.

Note that this answer also works for: How Much Should I Pay People to Come Work At My Startup?

In one sense, startups are just like any other company out there. They pay what they can for the talent they need. But in most cases, startups don't have the means to be able to offer a cash package that's going to be competitive with established companies. So they offset this gap with equity.

There is no standard calculation for how this plays out, but there are a few rules of thumb.

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Can Anyone Learn To Be An Entrepreneur?

12.2.15


You can't learn to be an entrepreneur in a classroom.

At least, I don't think you can.

I've thought about this for years, from the very first time I joined a startup and flailed madly trying to get a lay of the land that was never going to materialize. That company went from zero to acquisition in three years, and it was the most uncomfortable ride in the world until I figured out I'd just have to make shit up as I went along.

Which, I now realize, ten startups and five solid exits later, is also not the answer.

But seriously, you can't learn to be an entrepreneur in a classroom.

I guess you can learn some of the nuts and bolts -- the legal stuff, the financial stuff, maybe some code -- but that's left brain stuff, and I believe the vast majority of learned entrepreneurism is right brain stuff.

Can you imagine a class on leadership? I mean, I know they're out there but how do they keep everyone from stabbing themselves in the eyeballs. How about motivation and persistence? Is that just a 90-minute slideshow of inspirational quotes on idyllic backgrounds set to Kenny G?

And something tells me that the decision to enroll in a decision-making class probably seals your failing grade.

I've been learning entrepreneurism for 20+ years, all of it by doing. And I don't recommend that path. It sucks. It's full of costly trial-and-error, painful mistakes, humbling failure, crippling stress, and general peerlessness.

Actually wait, I do recommend that path, to a certain extent. You have to go through all that to truly call yourself an entrepreneur. You just shouldn't have to reinvent the wheel. Like everything I look at, I see the entrepreneurial journey and I want to streamline, reduce friction, and add more intelligence.

I believe you can apply those concepts to teaching entrepreneurism. But first you have to identify the right student.

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What To Do When It All Goes To Hell

How To Deal With Failure or Loss

12.7.15


The first thing to do is to come to terms with how much this hurts. I don't care what anyone tells you, no one is immune to the pain and suffering that comes with failure or loss. No one. Sure, as you get older, gain experience, and go through the process a few times, it becomes easier to navigate, but there's still no Get Out Of Suck Free card.

If it doesn't sting, it wasn't worth having. If it was worth having, you're in a world of hurt. Let it happen.

The second thing to do is don't do anything stupid. Emotional reactions are good for your mental state, but they can be bombs, so try to let them happen in a vacuum. It's like you were told when you were a kid -- Go to your room, beat the crap out of a pillow, scream at the top of your lungs, use all the swears in one sentence if need be. That's all fine and good.

Do this as often and as long as you need to. Just keep your emotional reaction out of public, off of the Internets, and away from breakable objects and relationships.

But definitely talk to other people. You don't realize how much shit people have been through until you open up about your own. Talking about yours and hearing about others makes it easier.

Then wait. It's going to take a while to get over the burn. Again, there are no shortcuts and people are all built differently. Some issues I get over immediately and others take forever. I never really know what the timeline is, and that isn't important. At some point I can function again. The sooner I understand this, the quicker I can get into recovery. I'll still be grieving, but grief and recovery periods aren't mutually exclusive.

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This Is What the Beginning of a Startup Looks Like

10 Years To Get To One Moment

1.21.16


Last night I played matchmaker.

After a couple weeks of wrangling the schedules of two particularly busy people I know well and respect, I finally sat down for a few beers with them. One of them has an idea and some means of getting it executed, the other has a ton of talent and an itch.

It took just minutes for these two personalities to gel and another half an hour for this idea to go from so-crazy-this-just-might-work to so-stupid-this-is-going-to-dominate. I got to sit back and watch it all happen.

Names changed to protect anonymity.

Floyd is looking to disrupt an industry that he's been working in for the past 10 years. He's become an authority and he's frustrated at how little progress is being made bringing his science into the mainstream.

Sarah is a techie who has dabbled in Floyd's industry as a hobby -- call it a fascination -- and before she got into tech she spent a few years out of college working at the fringes of Floyd's industry.

She didn't stay long because the industry sucked -- no innovation. So she's got ideas of her own, and getting to hear Floyd's thoughts on her ideas pushed just the right buttons, giving her the confidence to expand upon those ideas in a technical arena.

I have no doubt that Floyd's ideas will drive the company and Sarah's skills will push the tech to new limits. I got to sit back and watch and translate when necessary. It turned into a play-by-play of a startup formation and it was a beautiful thing.

Here's how it went down.

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Why That Startup Side Project Is So Important

Building The Startup Show

8.18.17





I'm so freaking lucky.

I realize how cool it is that I'm in a position where I can be so open about my side project(s) at any given time. I like to think I've earned that over a 20-year career of proving I can handle, and actually benefit from, doing two things at once.

In this episode of The Startup Show, Jon, Andy and I got into the really deep topic of side projects. I'm a big believer in the necessity of side projects, something between a hobby and a job, to fuel what it is your trying to do with your life. And if your "day job" is the right job, i.e. it's the roadmap to do what you want to do with your life, a second thing can't be anything but helpful to that first thing.

Over the last week I've realized a couple things. I've never been more convinced that Teaching Startup and The Startup Show can and will work and do big things, but I'm also more and more aware of how much I need to narrow my focus.

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The Startup Show: Doing Startup With Zero Ideas

It's not as crazy as it sounds

8.10.17





The latest episode of The Startup Show is the first in which we take an actual member question from our Talk board (in the member area of the Teaching Startup website, join now and use it please).

Dawn was let go from her job due to cutbacks. This is a great excuse for her to start her own company, which she has always dreamed of doing. One small problem, she doesn't have a single idea for a product, service, or anything else to sell.

This is actually not a problem. She served us up a great, universal entrepreneur's dillema.

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An uncomfortable but necessary discussion: The Startup Show talks sexual harassment

Because we need to move the conversation forward too

8.2.17





In Episode 5.2 of The Startup Show, we talk about sexual harassment in startup culture.

The recent incident at 500 Startups isn't the first time sexual harassment has made an appearance in startup culture. Far from it, just look at all the recent issues at Uber as a starting point. Nor do we think that this is something that will magically go away anytime soon.

It sucks, and we just feel like startup culture should, and more importantly COULD, be better than corporate culture in this regard. And we think the responsibility for that falls heavily on dudes like us.

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Introducing a New Re-Branded, Re-Imagined Startup Show

I spent the summer thinking about how to make Teaching Startup better

7.26.17





I don't want The Startup Show or Teaching Startup itself to be a local thing. I've been pretty adamant about that ever since ExitEvent, my last startup, couldn't get out of the local scene and expand nationally. But I also believe there are concepts we talk about on a local level that can inform at a national level.

What works for Raleigh and Durham can work for Des Moines, Mobile, Syracuse, even Austin.

In this first-ever "local" episode of the now rebranded The Startup Show, Jon Colgan, Andy Roth and I (no Chop this week), talk about everything from beer to religion to creative writing to west coast money and how they can influence and impact local economies, and how entrepreneurs can and should be at the heart of this.

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