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Meet the veterans who bring their unusual discipline, perspective, and problem-solving skill to the world of game-changing start-ups.
I first met Joseph Kopser six years ago in Mosul, Iraq. He he was an Army major serving in a cavalry squadron at the time, and I was a reporter for The Washington Post.
Kopser, 42, who retired from the military last week, is now the CEO and co-founder of an Austin, Tex. start-up called RideScout--a smartphone application that aggregates all of a user's potential ground transportation options in real time, everything from buses and Zipcar to rideshare options with friends or strangers.
On Memorial Day, we remember members of our military who made the ultimate sacrifice. I've interviewed thousands of soldiers over the years. One thing they've told me repeatedly is that the best way to honor that sacrifice is to remember those who gave their lives--and to live lives worthy of them. Today, I'd like to start telling you about some veterans who do just that. These are men and women who become entrepreneurs, trying to change the world for the better.
Military training is often cited as good preparation for business leadership. People might know a few anecdotal examples of this, like the fact that Fred Smith was a Marine officer who observed the military logistics system before he founded FedEx.
Still, the more prevalent story seems to be of veterans who have difficulty transitioning to the civilian world--stories of PTSD and movies about returning veterans in crisis. (Indeed, I've written a lot about troubled veterans and even military suicide in the past. These are very real problems.)
However, veterans bring amazing advantages to to the entrepreneurial game--things like discipline, perspective, leadership ability, and the learned skill of seeing problems as opportunities--to say nothing of having accomplished ambitious goals with the weight of a gigantic bureaucracy on their backs.
It Started With Pentagon Traffic
Take Kopser, for example. A 1993 West Point graduate, he and his classmate and Army buddy Craig Cummings launched RideScout while Kopser was still on active duty, running the ROTC program at the University of Texas at Austin.
Kopser came up with the idea during a Pentagon assignment, when he had to figure out how to get to work efficiently within the Washington, D.C. traffic nightmare. Enter Cummings, who had left the military to become an investor and entrepreneur. Kopser recalled sitting on his back porch in Arlington, Va., telling Cummings about his daily commute.
"I live five miles from the Pentagon, and I could walk, ride, or drive, but...if something goes wrong, my whole day is ruined," Kopser said. He'd been up half the night before looking for a website or app that would show users their transportation options in real-time. No dice.
"So I explained RideScout," Kopser said. Soon after, Cummings called back.
"That is a billion dollar idea to change society as we know it," Cummings told him. "I'm going to give you the money to make it happen. Give me your USAA bank account number."
That was in early 2011. Today RideScout is in beta after its launch in Austin during SXSW, and has closed over $700,000 in seed financing. The plan is to expand to Washington, D.C. and Seattle by the fall.
An "Equal-Opportunity" Opportunity
It's not just officers, who are generally college-educated and a bit older than enlisted service members, who find great success in the entrepreneurial world when they're given the tools to succeed.
I talked this week with Dave Liniger, the founder of RE/MAX, the giant, international real estate company.
Liniger has a new book out, My Next Step, about his ongoing recovery from a medical condition last year that temporarily paralyzed him. What struck me from his early story was that he took the first steps toward founding RE/MAX while still on active duty in the U.S. Air Force in the 1970s.
"Even as an E-4 [senior airman, getting] hazardous duty pay, it was poverty wages," Liniger explained. "So, I had read a book on buying and fixing up houses and selling at a profit. That started my entrepreneurial career."
His first property was a $10,000 duplex that he bought with just a $500 down payment.
"I sold it in six months for a $6,000 profit. All of a sudden I made more money on one real estate investment than I did on my entire salary and three part-time jobs," he said.
Liniger had dropped out of Indiana University after three semesters, enlisting in the military in the 1960s. He served in Vietnam, and said the experience changed his life.
"The military was incredibly important to me and my success," he said. "As a farm boy growing up in Indiana, my parents instilled in me a very good work ethic, but when I went to college at 17, I had no goal, no idea where I wanted to be."
The Air Force gave him motivation. "I fell in love with it from the first day. It grounded me, gave me a sense of purpose," he said.
As we'll see in the second article in this series, which highlights my interview with Air Force veteran and "Godfather of Silicon Valley" Steve Blank, the military itself deserves a lot of credit for having created the antecedents of the phenomenal tech explosion we've seen in this country over the last half-century or so.
In fact, the hardest thing about writing this kind of article, frankly, is the sheer number of great veteran-entrepreneurs who prove the point. I'm always eager to hear about more of them, so feel free to reach out to me here.
(Memorial Day is a day to remember the fallen. I'll be thinking in particular of two West Point roommates, Lt. Todd Bryant and Capt. Tim Moshier, who gave their lives in Iraq in 2003 and 2006.)

Because if you are a solo founder, you are always the smartest person in the room. As an investor, I want someone in there with you.
As a seed-stage investor, I get to see companies at the most formative stage of their development. One of the more interesting variables is the one-founder-versus-two-founders dynamic. I, for one, am a fan of the two-person founding team (or three-person, or four-person). In fact, it is now a requirement of our accelerator program that every company have at least two founders.
Why? Because when the 100 decisions that needs to be made that day bubble up to the top of your brain and the Top Five need to be prioritized, I want someone else in the room with you.
Because when you are a single founder, you are always the smartest person in the room and thus every decision is perfect.
I want someone else in the room. Every day.
So, how do you find a co-founder (ideally, one whose skills complement yours)? I would use the same technique you use (or used) to find your significant other. Seriously. The parallels are significant. Here are three thoughts I share with single-founder entrepreneurs:
- Know Thyself. If you are following my “complementary skills” angle you have to have a very good idea of who you are in order to find your co-founder. Not sure who you are? Ask around. Don’t be afraid-;this is crucial feedback.
- Network Like Crazy. Start talking to everyone who will listen about your idea and your desire to find a partner. Meetups, conferences, and entrepreneurial social events are perfect opportunities, as everyone there is by definition a potential candidate.
- Put the Dating in Founder-Dating. My partner, Dave Neal, and I dated for about three months. We met about every week in person and exchanged emails and phones call in between. We worked problems, found solutions, discarded ineffective ideas, and talked about everything we could think of. Most important, we talked about our failures.
As is the norm, there are websites and organizations trying to facilitate this process. It seems like we get asked every day to support some vehicle for matching up people. Think Match.com for geeks. www.cofounderlab.com, www.founderdating.com and www.startupwithme.com are all good online examples. Some of these sites also host face-to-face events that augment the online experience. Check them out.
As the start-up days turn into weeks, which turn into months, and you enter the classic “trough of disillusionment,” having a partner who inspires you, or covers for you when you have no mojo, or provides counter thinking, or tells you when you are off base is a gift. Of course, your partner gets the same in return.

Before you settle on a name for your company, check out these very simple yet brilliant thoughts on naming. Also, take the Ikea challenge!
As George Eastman, the founder of Kodak and godfather of the nonsensical naming trend said, "A trademark should be short, vigorous, incapable of being misspelled. It must mean nothing. If the name has no dictionary definition, it must be associated only with your product."
As Jason Calacanis, CEO of Inside.com and angel investor said, "If you go into a VC meeting with a crappy name, they will look at it the same way they look at you unshaven with a stain on your shirt. If you can't name your company well, you're simply not worth investing in."
So just for fun, take this quiz and see if you can tell if the word is a start-up or a piece of Ikea furniture:
1. Falster
a. A line of weather-resistant outdoor furniture
b. A bedside table
2. Clypd
a. An online exchange for digital advertising
b. A bedside table
3. Fruux
a. A cloud based platform for organizing contacts and calendar items
b. A shelving unit with sliding glass doors
Fun Fact: 19 of the top 25 U.S. websites have a name with two syllables or fewer.
Answer to all: (a.)

Indoctrination, vision, mission--you'll almost always find a little bit of cult-like mentality at the most successful start-ups.
If you ask 10 executives or business leaders what really motivates employees to do great things, you'll probably get 10 different answers.
Many will provide a generic response along the lines of employee engagement or emotional intelligence. Not that employees shouldn't be engaged or leaders shouldn't be self-aware, but let's face it, that's pretty baseline. It's not going to get your team fired up to go out and conquer the world.
Likewise, if you ask thousands of people what motivates them, you'll get some common responses. Many will say they want an environment where their work is appreciated, recognized, challenging--that sort of thing. But again, that's nothing to write home about.
If you want to really motivate your team, if you want them to jump out of bed in the morning excited to get to work and go to bed at night feeling like they've done something amazing, you're going to have to be a lot more creative.
The truth is, what motivates individuals is highly subjective and situational. There is no answer that will work across the board. It often comes down to the unique characteristics of an eccentric geek, some crazy idea, and a team that's made to believe it can accomplish great things.
So, instead of the usual boilerplate fluff, let me tell you how someone like Mark Zuckerberg, Larry Page, or Steve Jobs somehow manages to build a cult-like culture of people that love their work and truly believe they can make a dent in the universe. And how you can do the same thing.
Be the courageous hero. Believe it or not, inside every one of us is a kid who once believed in superheroes and romantic tales. There's a part of each of us that wants to be led by a hero of sorts. If you truly believe in your own vision, then you owe it to your team to play that role. Just don't overdo it and go jumping off buildings or anything.
Give them a Holy Grail to search for. Perhaps the most important part of the equation is the cause itself, a product that solves some huge problem that nobody's been able to solve or enables people to do something really, really cool. Pretty much everyone wants to see loads of people using something they had a hand in. Besides, cults are never really about their leader but about the cause.
Hire those who want to take that journey with you. If you simply hire folks who can do a job, that's all you're going to get, even if they are really talented. What you want are people that fit a certain type that resonates with you and what you're trying to achieve. Granted, you're not looking for an army of clones; a little diversity is a good thing.
Show them the way. A group needs direction and discipline to fulfill its cause, strategy and planning to turn an idea into reality. You have to be able to fill the shoes of a good manager who can point people in the right direction and be there when they need guidance and encouragement. It's true that not every start-up founder makes the best CEO, but they're usually quite capable, at least in the early stages.
Draw them into your story. It's one thing to have a unique vision--it's another thing to be capable of connecting with folks in some emotional or intellectual way. That requires a certain leadership presence, a healthy ego, and perhaps a little bit of Kool-Aid. Your team needs to feel a sense of purpose, that they're an integral part of achieving some great mission. Perhaps indoctrination is too strong a word, but you know what I mean.
Make it up as you go. We hear the stories about Facebook, Google, and Apple over and over but the truth is that most start-ups don't score big on their first idea. Besides, even if you've got a great concept, your team's unique dynamic may evolve to a great extent on its own. So you've got to be open and adaptive. Pay attention, listen and learn, look for clues to the culture that makes the whole so much greater than the sum of its parts.
If you doubt that the culture of a start-up can be a lot like a cult on a mission, ask anyone who's been a part of one and they'll tell you. I've been there myself, more than once. There is indeed truth to the metaphor. They're not all like that, but some of the most storied and successful ones definitely are. I'd tell you which ones, but then I'd have to swear you to secrecy.

Steve Schlafman, principal at Lerer Ventures, offers tips for passing the smell test.
Passing investors' smell test takes more than just a great idea, said Steve Schlafman, principal at Lerer Ventures, on Wednesday during Internet Week.
It also means putting your best foot forward.
Here are three ways a start-up can do so:
Have a great track record--and a great team. "We like founders who have history of accomplishing stuff," said Schlafman. Oftentimes, founders are are high achievers who have been leading since they were young, perhaps as a class president or a coder.
If there are several founders then investors will evaluate their dynamic, taking time to examine things such as how long the founders have known each other and where they first met. Team chemistry is critical, stressed Schlafman, because the company's culture starts with them. Maintaining that culture means hiring the best people, especially in the beginning when start-ups are short on cash and resources.
Know your story. "Being able to articulate why and what you are building in a very concise way is super critical," said Schlafman, noting a company description is not enough. "It's like the whole Simon Sinek TED Talk: Why are you doing this? What's the purpose?"
Have a game plan. Entrepreneurs should also be able to explain their product, why consumers need it, and how it will be delivered.
"I am a seed investor, I am not investing in a PowerPoint presentation," Schlafman said. "I am investing in a founder, in a product, and I want to see that you can ship something. Or that you can prove to me that someone wants your product.
"You don't have to walk into my office and be like, 'Hey, we figured out all of the lifetime value economics of our business,' but I want to know how you plan to get the product into the hands of the people that need it most."
Make sure your action plan includes a means of distribution, which communities you'll target, and how you plan to expand your reach.
Speaking of customers, make sure you know yours, Schalfman concluded. "How much do they sleep? How much do they make? What do they do on the weekend? Understand how they purchase products."
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