Introducing Teaching Startup: Getting Started

Everything You Should Know About Starting Your Own Company in 10K Words


So summer is winding to a close and that's kind of disappointing. I never feel like I'm squeezing an entire summer's worth of fun into what seems like an increasingly small window of time. Didn't summer used to be like end of May to beginning of September? Now it seems like it's three weeks in July, and for most of that time it's either 100 degrees or thunderstorming.

But I did get something accomplished this summer, and it came from an unlikely place.

On the digital shelves of Amazon you'll find my latest book, Teaching Startup: Getting Started. It is, as the cover proclaims, "everything you should know before starting your own company." It's a free book, because it needs to be, and it's a quick, easy, comprehensive-but-enjoyable read through each stage of startup and what and who you need to get through each one.

Go get it. Right now. There are no strings.

A couple of things this book isn't.

Notice I didn't say "everything you NEED to know," because this book isn't it. You can't possibly know everything you need to know before you start a company. If you did know all that, your hourly rate would be off the charts. But this a rough sketch of the startup universe. It's meant to tell you how long the race is and what the markers are, as well as what you should be bringing along with you.

And notice I didn't say "before starting your FIRST company," because the book isn't just meant for first-time entrepreneurs. It took me several years and several starts, including a couple exits, before I felt like I had the lay of the entrepreneurial land. Sure, I wish I had read this book before I started my first company. I also wish I had read it before I started by fifth company, or before I joined my first startup. Or for that matter, before I took my first job.

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How Numbers Can Wreck Your Startup

Sometimes the data is lying


I'm about to commit heresy in certain startup circles. So let me state first that I'm a devoted numbers guy, I believe wholeheartedly in the measurement of progress. I get chills when the numbers I've decided will determine the success of failure of my pursuits happen to point towards fortune. And I get all cranky when they dip, or even worse, when they don't move at all.

This is true not just of startup or business or money, but anything. Let's talk health. I track my runs, their length, my speed, the miles I run in a month, and maybe you do this too. But I also track everything else, my weight, my calorie intake, my caffeine intake, my shoe tread -- at one point I had a stat for how I felt at the end of a run, and I was seconds away from deciding that the data point for that metric should be an emoji, like, "After my run, I feel = (poop)"

I inched back from that precipice.

But if there's one thing I've learned from a lifetime of setting goals, establishing metrics, tracking progress, and recording the results of myriad experiments, it's that sometimes the numbers don't mean anything, and in rare cases the numbers will straight up lie to you.

Now, I'm not talking about tracking the wrong data, what's more commonly known as vanity metrics. Anyone with six months in marketing or old enough to remember eyeballs as a metric will tell you to watch out for stats that make you feel good but really just mask imminent doom.

I'm talking about those moments when all the numbers are off. I'm talking about gut over brain, heart over head, and the fact that most people don't tell you often enough that an entrepreneur has to be right when everyone else is telling them that they're wrong, and those naysayers have the data to back them up.

Yeah, I know. Me, the data guy, telling you not to trust the data.

Your results may vary, and this is a stunt that should only be performed by professionals on a closed course under heavy adult supervision. Don't try it at home.

But sometimes you have to ignore the numbers.

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Rerun: The Late Shaft

Talk Shows Battle Like It's 1993


Over vacation I'm reading The War for Late Night by Bill Carter, the 2010 recap of the massive dustup of NBC Late Night when they replaced Leno with Conan and then reversed it. Then I found this piece I wrote while that was going on. Turns out I was right. How come no one ever asks me about these things?

When people approach me in the local supermarket or at the Jazz Dance studio and ask me how I got to be so damn funny, I usually have three answers:

1. Screwball Teen Comedies
2. Gatorade
3. David Letterman

Then I chastise my entourage for letting the general public wander into the Joe Zone.

Beyond the obvious implications of the rule-of-threes and non-sequiturs in that list, my answer has a lot to do with upbringing. I was exposed to funny at an impressionable age. I was a little kid during the time when the edge of television began its transition from Little House on the Prairie to Janet Jackson's wardrobe malfunction.

Somewhere in there, TV grew up, and during its dorky teen period, shows like Saturday Night Live and Late Night with David Letterman were pushing the envelope. "Lord and Lady Douchebag" may seem almost quaint today, what with the smack usage and hooker references, but back then, it was sophomoric humor aimed at adults, meaning it struck a huge chord with kids and teens as taboo we could kind of get away with.

Yeah, it may have nerded me up for a life of... whatever it is I do. But it kept me away from the smack and the hookers. The unfortunate side effect for me was a brimming fascination with this entertainment universe, a lifelong study of the mechanics of fleeting fame. I don't really dig the Sex Pistols, it's not my bag, but I've read and watched everything I could get my hands on about their story, which is far more fascinating than their art or their music, which is crap.

It's why I watch Survivor, not because I'm curious about the relational dynamics of putting 20 strangers on an island to compete against one another, but I'm a sucker for the relational dynamics of putting 20 strangers on an island to compete against one another with a camera crew.

Late Night with David Letterman skewered that entertainment universe. In those early years, the jokes were awful and the sketches were unwatchable, but it was meant to be that way, because the target was rich. The Top Ten Lists were only funny when they tackled fame and notoriety. And all along as Letterman worried about becoming what he mocked, he found he could do little to stop it.

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Rerun: The Bigness

This will turn your world upside down, but it's mostly about Big Country


You're not seriously going to attempt to write a column about Big Country, are you?

Yes. Yes I am.

Big Country. The Scottish musical quartet that barely mattered some 20-odd years ago.

The same.

You're going to attempt to write a column about them?

Not attempt. Consider it in the can.

That's nuts.

It is not.

So... is it going to be semi-ironic?

No. It's straight-up. I did a column on Living Colour once. It got huge play.

But they had just reformed and released a new record.

Not relevant.

Neither is Big Country! Do we go back to the 20-odd years ago thing or...

Look. Big Country would have and should have been as big as U2. They're more talented musicians and they excelled at layering a huge, important sound over huge, important lyrics. 1983's The Crossing is -– song for song -- a beautiful, sprawling record that stands up there with War and The Unforgettable Fire. In fact, War and The Crossing were both produced by Steve Lillywhite. "Just a Shadow" from 1984's Steeltown should have been their "With or Without You." It's haunting, beautiful, and lush with an explosive vamp at the end.

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Rerun: Parent of the Year

On further review, the lack of personal space on the planet is somewhat shocking


NOTE: I wrote this in 2009, a nice little piece on surviving vacation rerun while I'm out on vacation. It gets better as the kids get older that's for sure.

Disney does it right.

If you're at a certain age and have produced a certain number of offspring, this is a phrase you'll hear over and over again from friends, and acquaintances. What's more is you will eventually utter it yourself. Trust me on this one. No one has fought the idiosyncratic sport-shirt, beer-gut, lawn-care, SUV-point-and-drive, Baby-Bjorn, organic-cruelty-free-strained-peas model of parenting harder than me. I'm like Don Quixote in a Van Halen (Roth) T-shirt, still berating what we used to call "the yuppies" even though anyone under the age of 30 never knew the term and if I explained it to them would point a cruel digit at me and shrug, "Dude. That's so you." Whatever.

This last month marked our second annual family trip to Disney World. And it's the kind of thing where you don't really hear about it in your day-to-day, but when you bring it up, everyone you talk to is either just returning, about to embark, or in the planning stages. Advice zips around the room, and it's usually spot on, but no one ever tells you how to deal with the single biggest flaw in the Disney system. Because despite the irresistible magic, the total commitment to quality, and the unabashed cheeriness and helpfulness of the staff, Disney World can not conquer their one major issue.

They still have to let people into the park.

Nothing crushes the feelgood experience of a day at Disney World like other people. And this isn't true of everyone, I can point to the lady who helped my daughter get the courage to ride a ride, or the nice woman who left an attraction to catch up to me and the boy and return the autograph book he had unknowingly dropped. In fact, one of the great things about Disney World is all of the world of hope hoohah rubs off on the vast majority of paying customers.

But those exceptions will wear on you, man.

So let me help you through this experience. Let me get you through a day at Disney World, which might also get you through a day at any shopping mall at Christmas season, or even your office on a busy day, by identifying the three universal types of people you will invariably encounter during the experience, and giving you the tools to deal with them.

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Rerun: Laughing In The Face of Death

Another Look At Humor As Your Best Defense


So I'm on vacation this week but I thought I'd keep the content rolling with some blasts from the past that still hit home today.

I just did a piece on humor in the election cycle, but I did probably a much better piece when I focused on how I use humor in my personal life to get me through the worst of times.

I wrote this for Intrepid Media back when my grandmother passed away back in 2011. It's much more personal and quite a bit funnier, which always seems to happen.

laughing in the face of death
potentially stupid, definitely necessary

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Why I'm Voting For the Giant Meteor

Don't Forget Your Sense of Humor


Now, more than ever, we're all going to need a healthy sense of humor.

In fact, I'll go so far as to say that's what's wrong with the world right now, which is something I never do, because I'm constantly inundated with other people telling me what's wrong with the world right now. This happens mostly on Facebook, which is like the clearing house, everything-must-go, one-stop-shop for righteous indignation without trying very hard.

Look, I don't want to add fuel to the fire. I just maybe want to throw on a clown in a flame-retardant jumpsuit.

I'm sorry. Flame-CHALLENGED jumpsuit.

But see, that's part of the problem. One of the great things about humor is that you can get away with saying almost anything, provided the joke hits home. This has always been the case. You want to make fun of race, religion, and politics? Just make sure the punch line kills.

Comedians like Daniel Tosh can literally step all over everything. He has his detractors, but almost everyone thinks he's funny, even when he makes people uncomfortable. I use Tosh as an example because one of his best lines serves as a warning for anyone taking him too seriously:

"Your honor, the comedian clearly stated…"

Even so, Tosh is always one step away from being Michael Richards. He's Kramer, for those of you over 30, and for everyone else, he's that guy who snapped and just kept shouting the n-word from the stage of a comedy club about 10 years ago.

There's no coming back from that.

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Why Startups Need to Choose Their Target Market Carefully

Make sure you're solving problems for people who will pay to solve them


Yesterday, I had a cup of coffee with an entrepreneur whom I knew but hadn't previously spent a bunch of time with—our paths just never crossed until a couple weeks ago.

He's a technical entrepreneur, sharp as hell, but has spent his career hitting self-funded singles. Of course there's nothing wrong with that—he's doing well for himself. I'm just saying you probably don't know him.


His latest idea is legit. It's serious tech that he has architected and built himself. It plays off of technology that's already been adopted, but he's taking it in a unique direction. He's early with the idea, but current enough that what would've sounded crazy a year ago makes perfect sense today.

And, you know, good for him. I love that moment.

He just recently brought aboard somebody to handle business development and marketing. The time is right, because while his website does a fantastic job of explaining the how of his tech, it has precious little on the why. Classic tech entrepreneur go-to move.

As we talked and dove deeper into his grand plans, I realized that he's pulling all the right levers. Except one.

He told me he's starting his approach by creating a first use case—for entrepreneurs.


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Five Roles of Startup: Growth

Investor, Advisor, Mentor, Service Provider, Community


The five roles I'm discussing in this series are general, but intended to identify everyone inside and outside the startup's organization. You must have someone playing all five roles, and in the early days, two or more of these roles are probably going to be played by the same person.

Up until now, all of the roles we've discussed have been people you bring into the company. Here they are:

Vision -- Founding, Leadership, Management, Product, Future. These are your leaders, explainers, and decision-makers.

Build -- Design, Engineer, Perform, Deliver, Support. These people make the product.

Sales -- Salespeople, Marketing, Business Development, Public Relations. These people sell the product.

Operations -- Human Resources, Finance, Legal, Administration. These people make sure the company is running smoothly and efficiently.

If you lock down these four roles, you are well on your way to building a successful startup that has a very good chance of having a long life. I will say, in all seriousness, that you can stop there, as long as you keep the best people in these roles.

However, if you're building a startup with an intent to be not just good, but amazing -- world-changing, dominating, life-altering, that kind of thing -- you're going to need boosters for your rocket, so to speak.

Filling this final role is what brings a business up to the speeds that we normally associate with the startup stories we see and hear about in the press. But just because you chase growth doesn't necessarily mean you're going to launch your startup into the stratosphere, up there with Google, Facebook, Uber, and the kinds of companies that grow to be worth billions of dollars.

Ultimately, how far you go depends on both how good you are and what you want out of your journey. You don't have to hit a home run -- a triple or a double is what you might want to aim for -- but regardless of how far you want to get, you're going to need to fill this final role.

Growth is the role that propels a startup beyond the limitations of the talent and resources within the company itself. Most of this role is filled with people who don't work for the company directly, but partner with the startup as a key member of the extended team.

The Growth people provide additional resources, including money, advice, connections, services, education, and more, usually in exchange for something else. That something else can be a piece of the startup, a percentage of the revenue, or even cash payment.

Two things to remember about the Growth team. 1) It should be relatively small, no matter how big your startup gets. 2) The individuals on this team should be temporary. Those aren't hard-and-fast rules, but it should be in the back of your mind that almost every member of this team will eventually be replaced, either by someone new or by no one at all because you no longer need what they provide.

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Five Roles of Startup: Operations

HR, Finance, Legal, Administration


The five roles I'm discussing in this series are general, but intended to identify everyone inside and outside the startup's organization. You must have someone playing all five roles, and in the early days, two or more of these roles are probably going to be played by the same person.

The prior three installments in the Five Roles of Startup series were all about getting product out and revenue in. With Vision we set up leadership, with Build we're getting the product made, and with Sales we're putting the product into the hands of customers, the lifeblood of your startup.

You might think that once those three roles are filled, you can just sit back, repeat the cycle over and over, and carve out a lifelong career with maybe a golf membership and a better car than you would have driven otherwise.

I'm here to tell you that you probably can.

You were expecting the opposite, weren't you? Come on, admit it, you thought I was setting you up to slam the door in the face of your dreams.

Sure. Fine. It's no guarantee, but if you can dominate Vision, Build, and Sales, keep your employees motivated as they grow more experienced, stay relevant and unique, keep out of hot water, and continually solve customer problems in a way that makes them happy, you can repeat the cycle until you retire.

No joke, I'm totally cool with you doing that. Chances are, however, that you won't be totally cool with that. At least not for long.

So the final two installments in the Five Roles series are about building a better, faster, stronger company, with less emphasis on the product. The role I'm going to talk about in this lesson is one you need to think about every day. And to be honest, you have to fill this role whether you want to be the biggest company in your industry or you just want to coast.

Operations keeps your startup afloat, tasked with making sure that your company is doing well today and that it's set up to do better tomorrow.

These people are the gears, the nuts and bolts, the heart of the company. These are the folks in charge of finding your employees, keeping an eye on the money, making sure you stay out of trouble, and otherwise helping everyone else focus on their job.

Again, there are probably dozens of specific roles that make up Operations, and the very term can mean different things to different people. However, most of the role breaks down into a few broad, necessary components.

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Five Roles of Startup: Sales

Salespeople, Marketing, Business Development, Public Relations


The five roles I'm discussing in this series are general, but intended to identify everyone inside and outside the startup's organization. You must have someone playing all five roles, and in the early days, two or more of these roles are probably going to be played by the same person.

So far we've covered the two roles in startup that focus on turning a great idea into a great product. The Vision people are your leaders, your explainers, your decision-makers, while the Build role defines the team that makes the product.

But even when your startup has built the most awesome product ever, someone has to actually get out there and sell it. And no matter how amazing your offering is, this is not an easy job.

Sales is the role that pushes your product into the hands of paying customers, but this means much more than exchanging money for goods or services. In fact, for most startups, sales is where the grand plans break down, because too few entrepreneurs understand the sales process, and even fewer put a priority on the Sales role.

A common misconception in startup is that once the product is built, the customers will come knocking at your physical and/or digital door, wallets open, ready to purchase. But the famous phrase "Build it and they will come," was never true, regardless of what you've seen in the movies. "Viral sales" is also a myth, in the sense that you have roughly the same odds of creating a viral smash hit as you do of winning the lottery.

Sales must devise a strategy, or a series of strategies really, for reaching your market, educating them, persuading them, negotiating with them, closing the deal, and retaining them. Then all of these events must happen in the shortest possible time frame at a perpetually lower cost, all while figuring out how to get existing customers to buy more product more often.

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Five Roles of Startup: Build

Design, Engineer, Perform, Deliver, Support


The five roles I'm discussing in this series are general, but intended to identify everyone inside and outside the startup's organization. You must have someone playing all five roles, and in the early days, two or more of these roles are probably going to be played by the same person.

In the first installment of this series, I defined what it means to play the Vision role in startup. These are your leaders, your explainers, your decision-makers. While the Vision role might seem the most important, the truth is that every one of the five roles is just as critical as the next.

To illustrate that point, someone has to make the thing you're going to sell. Build is that role, the people who design, make, test, move, and maintain the product. That's what we'll outline here. In future installments, we'll cover the three other roles: Sales, Operations, and Growth. You don't have to dig into all the roles now, but it helps to know what they are.

Build can be difficult because the skills required for this role totally change depending on what kind of product the startup sells. You need a completely different kind of expertise to build software as compared to soft drinks, or heart rate trackers as compared to heart medicine.

Furthermore, some startups don't even sell a product, they sell a service. For our purposes, however, a service should be treated as a product in most respects. A service startup should be trying to break new ground and invent new solutions to old problems, whether that's with consulting, photography, pet washing, or whatever.

So the concepts I'm outlining in Build are meant to apply to any kind of startup, regardless of the type of product or service.

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Triangle Startup: Five Years Into a 20-Year Plan


Just over five years ago, I held the first official (as in not a test run) ExitEvent Startup Social. A year after that, I started writing content three times a week under the ExitEvent byline. A year after that, I was negotiating my own exit from ExitEvent, assured that ExitEvent's future would be bright.

Today, nearly three years after that exit, I'm pretty thrilled with how far the Triangle startup scene has come. Four years ago I was asking how Raleigh was going to play with Durham. Three years ago I was asking if Chapel Hill was ever going to wander off campus and if Charlotte could get out from the shadow of big banking. Two years ago, Wilmington and Asheville were still far off outposts, may as well have been Tattooine.

Not all of those questions have answers, and not all of the answers are answers that I'm 100% in love with. But there's no question that where we are today, five years from that first official meetup, is a far, far better place than where we were in 2011, when I was still going to entrepreneur events and asking the only other entrepreneur there where the hell everyone else was.

So in 2016, it's safe to say that the Triangle is on Year Five of a startup renaissance that began at roughly the same time ExitEvent kicked off (coincidentally, I have a knack for being in the right place at the right time).

Over those five years, you can look at all sorts of numbers and statistics on the Triangle and draw any number of conclusions about the health and strength of the startup ecosystem. Almost all of the numbers are trending up, so almost all of the conclusions are positive.

But if you know me, you know I'm an 80/20 guy -- Let the numbers do 80% of the work and then flesh out the remaining 20% with good old human intuition and common sense. So I went and did what I do a lot, I talked to a bunch of people.

Here's what I can tell you:

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Five Roles of Startup: Vision

Founding, Leadership, Management, Product, Future


One of the truest descriptions of an entrepreneur is a person who has to do a lot of different things at the same time. The term for this has always been "wearing a lot of different hats." I don't like this term, mostly because it implies that you have to take your leader hat off to put your builder hat on.

The truth is you have to stack several hats on your head at once. Like Bartholomew Cubbins.

On any given day, an entrepreneur must be a leader, a builder, a salesperson, an accountant, and do several other jobs. As the company grows, you can hire other people to do some of these jobs for you. Hopefully, the people you hire will be better at these things than you are.

If you think about all the things an entrepreneur has to do, it can be overwhelming. Maybe you're an expert at one or two of them, or maybe none of them, and that's OK. Maybe you're good at a few others. Maybe you stink at finance, or sales, but if nobody is paying the bills or bringing in money to pay those bills, your company is not going to last long.

I'm not going to talk about every job at once. Much like when I wrote about the Five Stages of Startup and broke the timeline down into a simplified roadmap, I'll reduce the dozens of jobs an entrepreneur needs to do down to five basic roles you have to fill.

The five roles I'm discussing are general, but intended to identify everyone inside and outside the startup's organization. You must have someone playing all five roles, and most of the time two or more of these roles are going to be played by the same person.

First off, here are all five roles (with links where the lesson has been published), because before you dig deeper into any of them, you should be aware of what they all are:

Vision -- Founding, Leadership, Management, Product, Future. This is the one I'm talking about now. There is also:

Build -- Design, Engineer, Perform, Deliver, Support

Sales -- Salespeople, Marketing, Business Development, Public Relations

Operations -- Human Resources, Finance, Legal, Administration

Growth -- Investor, Advisor, Mentor, Service Provider, Community

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Five Stages of Startup: Level 5 -- The End

Exit, Failure, Graduation, Next, Giving Back


The five stages of startup I'm discussing are not THE five stages of startup. They're just landmarks, broken down and generalized into something that we can all hopefully use as a guide, not gospel.

This is the final stage of the generalized startup timeline, and with this, we've now covered the entire roadmap, from humble beginning to glorious end. Level 1: The Jump is the period of time when you have a great idea that will become a great product. Level 2: Start is when the company is formed, it figures out how to operate, and launches that great product. Level 3: The Journey is about running and growing your company and selling your product. Level 4: The Grind covers all the ups and downs along the way.

But all good things…

The End can happen a few different ways. There are happy endings, horrible endings, and endings where you just shrug your shoulders and move on.

You shouldn't really do a lot of planning for the end. Your goal is to build an incredible business, one that you want to work on every day for the rest of your life. But let's face it, you're an entrepreneur, and you might find that there are other ideas you'd like to pursue -- ideas that may be totally different from the one that got you where you are today.

If you've done your startup right, there will be several knocks of opportunity at your door, people who want to buy everything you've built, and you'll need to listen to most of those offers. If you've done it wrong, failure -- inevitable, heartbreaking failure -- will come calling instead, and that's a call you've got to answer too.

Oh, and I need to tell you that you can do everything right and failure might just show up anyway. He's kind of a jerk.

Regardless of how you close the curtain on your startup, the end is also a new beginning, and you'll need to know how to start over.

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