Travis Truett is the founder of Ambition, a sales productivity platform based around teams. Here Travis talks about having a healthy disrespect for authority, motivating millennials in the workforce, and his experience firing customers.

Travis, tell me what your path was like to becoming an entrepreneur.

Calling it a path is a bit of a stretch. I definitely hit a few forks in the road.

I’d say a healthy disrespect of authority led me to where I am now. In college I skipped most of my classes to work, and try new things. I had a corporate internship, and was working on all these side-businesses. Early on I realized that I wanted to be in control of my own destiny.

When I graduated from college, instead of jumping into a job, I listened to some very wise mentors of mine. They told me if there was anytime to travel and do something crazy, it was right after college.

I spent two years traveling. I worked in Europe as a climbing instructor in the fall and summer. Then I’d move out West to Utah or California and work as a ski instructor in the winter and spring. I was living the bum life.

At some point I got pretty restless with it. That’s when I joined up with some buddies from college to start a company.

The three of us were business guys. None of us were technical. We had this idea, but nobody knew how to move forward with it. Our solution was to outsource it, and we found a firm that could build it for $12,000.

Now remember, I’d been living like a bum for the previous years. I had no money in the bank. In order to fulfill my portion, I surrendered my life insurance policy, sold my class ring and put all my assets on the line. I didn’t know any better.

As you can probably surmise, 10 weeks later all of our money was completely wasted. It was an epic, epic failure. I was playing the role of project manager for the first time, and we had absolutely no idea what we were doing.

“The number one reason startups die, is because they run out of money. You can blame it on a lot of things, but when there’s no money, it’s over.”

It fell apart; however, two very special things happened. It solidified my belief that entrepreneurship was for me—even though I was as broke as I’ve ever been in my entire life. I was so inspired as I was during that 10 weeks as a project manager—I knew I could never go back. The second critical thing was that if I was going to stay in technology, and be a leader in technology, I had to learn to program.

The best managers know what it is like to be in the trenches, and build, and get down and dirty when they have to

I devoted a couple of years—every second of every evening and weekend to learn how to program. Eventually it started to pay off. Fast forward three and a half years, and here I am.

You were teaching yourself to program after college?

Yeah, that was after college.

There was an intern I had worked with at a previous startup. He told me when you look at a computer for the first time, you either want to take it apart and learn how it works, or you want to play games and talk to girls on it.

Unfortunately, I was in the camp that was playing games and talking to girls. If I could go back in time, I’d learn how to program from the get go.

I went to college and wasted four years. It wasn’t until I was two years out that I started learning to program.

What is your main language?

I’m really a one-language type of guy. I mainly work with Python, but also the web stuff—HTML,CSS and JavaScript.

I’d like to dive in and learn C, Lisp and everything in-between. Unfortunately, I spend less time programming now, and more time running the business. It is fun, but I genuinely enjoy the engineering bit of it. Hopefully there will be a time when I can get back to building.

Ambition Team Page
The Ambition sales team page shows stats like the team score, record and highest player score.

There just aren’t enough hours in the day.

No, there’s not.

We need to cure sleep. Once we cure sleep, I’ll be good to go.

I like something you said earlier—having a healthy disrespect for authority. Could you elaborate on that?

The best example I have would be my last real job.

I was living in California, and was at the end of my stint of being a bum. There was a ski shop I’d been working in for a couple of months.

We had a manager—she had the whole store on lockdown. Everything had to go through her, and she ran the place with an iron fist.

One day corporate decided to come and pay us a surprise visit. They asked all the employees what are some ways we can improve the business. Most employees, especially in a ski shop, just nod their head. They just want to get out and ski.

I was like, “It’s funny you asked.” Then I rattled off about 20 things I thought could be improved. It got back to my manager, and she reprimanded me for speaking out of turn, and did not follow the chain of command.

I just quit right there.

That is the only time in my life that I’ve just quit on the spot. You know, I’d like to believe that I’d have a tremendous amount of respect and humility for the right organization and the right authority figure. My experience in both the corporate world and at a grocery store tell me that I don’t do well with complacency, authority and people that like to manage.

I’ve never done well with people that like to be a manager, but not a leader.

I can sympathize with that.

Let’s talk a little bit about Ambition. How does it work? Tell us about it.

Absolutely.

Ambition came about through a random conversation with two of my cofounders. We all have varying levels of sales experience. Brian had done enterprise sales at HP, while Jared and I had worked in the retail space.

We were working on a startup called Fire Plug, which was in the news space. We were frustrated one day. We needed to build something that we could actually sell—something that was B2B, and where we could build the relationships that we know how to build.

“If you learn how to go door-to-door, spending 12 hours a day in the hot sun, and having people say “No” to your face, then sending out an email is nothing.”

We came to this epiphany that fantasy football was one of the most exciting moments in the sales office. Everybody gets so fired up, and it is always a great time. There are 23 million Americans that play fantasy football.

What if we could take the paradigm behind fantasy football, where employees form teams and compete week-to-week across seasons, and apply that to the workforce?

It was our first “aha moment” as entrepreneurs. When we launched it, not only were people using it, but we were actually able to show improved numbers—monthly phone calls, sales and more. We realized it was time for—and I’m not a big fan of this term—enterprise gamification.

Most companies were complaining five years ago that millennials are not as diligent and disciplined as their predecessors. Now we’re coming and are starting to take over the work force. Businesses can either engage millennials and drive productivity, or they can complain about us and get the same results.

We decided to start building Ambition and sunset the previous startup, which was doing decently well.

We had a few acqui-hire offers, but we decided that Ambition was too promising. Even if we did the golden handcuff thing for a few years, we thought it might be a missed opportunity. We turned those offers down, and focused on how we could make sales environments more productive.

This Fire Plug news app—that was going to make money from ad revenue, but you wanted to actually be able to sell something?

Basically, yes.

Fire Plug didn’t really have a business model. It was the typical, let’s get a bunch of users and figure something out.

Again, it was doing well. I’m very passionate about the space. One day I do want to reawaken Fire Plug, but in the mean time we decided to play to our strengths. Not only our strengths as in who we are, and what we’re good at, but the strengths of being in Chattanooga, Tennessee.

You could make the argument that if you want to be a news startup, you should be in San Francisco or New York. If you want to be a B2B startup that sells to unsexy companies, Chattanooga is a perfectly fine place to do that.

I’m a huge fan of technology companies in the South, so I think it is awesome that Ambition is headquartered in Chattanooga.

I closely follow a lot of startups in Atlanta and B2B is where they are making money. They don’t have a million users, but they are making money with a few enterprise clients.

What are some of the other advantages and disadvantages of being a tech startup in Chattanooga?

I’ll say there are a lot of advantages to being in the Bay Area—the collision points in all of the coffee shops. You could meet this incredible developer who can solve a problem for you in about 10 minutes. You might run into an investor, and that could lead to funding down the road. Those things are big, and can’t be understated.

The top tech talent does gravitate toward San Francisco. If you need to scale a top-tier engineering team, I don’t think there is a better place to do it.

“The best managers know what it is like to be in the trenches, and build, and get down and dirty when they have to.”

Ambition Conference Room
Ambition CTO Wes Kendall and Data Scientist Erik Swanson talk in the conference room.

On the other hand, the Bay Area is incredibly expensive. The number one reason startups die, is because they run out of money. You can blame it on a lot of things, but when there’s no money, it’s over.

Ambition can operate in Chattanooga at one-fifth the cost of the Bay Area. At this point it just makes sense. The money we’re saving on rent can go toward having an extra sales guy or two.

Another thing is we don’t have to deal with all the distractions of the bay area. In Chattanooga, we don’t have all of the cocktail parties, or conferences, or hackathons every night like San Francisco does.

We get in the office at 8 a.m. work until 7 p.m., eat dinner, then we’re probably going to come back and work for a bit. There aren’t a lot of things pulling at us, so it is really conducive to getting a lot done.

We spend less money, and spend more time working. I’m certain that is going to make us more successful down the road.

Speaking of San Francisco, how do you split your time between Tennessee and California?

A lot of red eyes, and a lot of early flights. I’m an early riser, so it’s not that bad.

I’m in San Francisco right now. I got up at 4:30 a.m. and caught a 6 a.m. flight out of Chattanooga. I’ll be here for most of the workday. On Sunday, I’ll take the red eye home, and be in the office Monday morning.

Right now I’m trying to spend a few days in San Francisco each month. We have some customers out here that we’re talking to, but most of it is keeping investors up to date. I want them to know what is going on, what our growth looks like, and what struggles we’re having. Whether we’re doing good or bad, it is important that we stay on the radar of our investors.

As a company that makes tools for people that sell things, how did you get your first customers?

Our first customer was someone that we knew in Chattanooga. They had a huge sales team—about 400 people. We told them about the idea. They told us that if we built it, they would pilot it.

The pilot went well. We asked the company who are five other companies that could use this, and could get us in the door with. We’ve used that philosophy with everyone—customers, investors, friends and family.

It’s like a referral program?

Yeah, it’s like an informal, off-the-cuff referral program.

It has been very successful for us.

For startups, what are the key sales metrics they should be looking at?

Customer acquisition costs, lead times, and sales cycle lengths are so difficult to measure in the beginning. You’re still trying to find product, market fit.

To us, it all comes down to behavior. Where are you getting the most traction finding customers? Email, phone calls, a LinkedIn connection? Focus on one of those and see where that leads. Maybe it leads to a web demo or an in person meeting.

Focus less on the financial measurements, and more on simple conversions.

What makes a great salesperson?

It’s cliche, but it takes hustle.

I’m not sure if confidence is the right word, but it takes someone who is not afraid to hear “No.” In my opinion, the best salespeople are the ones that did door-to-door sales in college.

If you learn how to go door-to-door, spending 12 hours a day in the hot sun, and having people say “No” to your face, then sending out an email is nothing.

As a startup hiring salespeople is a bit different, you don’t want to find a sales person that is too strategic. At the end of the day you need someone who can wear several different hats. Maybe they need to try a few different mediums, maybe they need to start writing content and attaching it to some of the emails being sent out.

The early sales people definitely need to be a bit more entrepreneurial, and shouldn’t be afraid to try new things. At the same time you don’t want someone, who doesn’t want to do the nitty gritty work and wants to sit back and look at Google Analytics all day. That isn’t going to get you anywhere.

What is the future of Ambition? What are your next steps?

Our product is solid.

The next step for Ambition is to focus on a few key integrations in the next 3 to 12 months. We’ve done SalesForce, Cisco and some of the more major ones. Now we need to knock out some of the integrations that cater to smaller teams, such as Google Apps and maybe a simple CSV uploader.

A big focus is going to be on gathering more data, and allowing companies to aggregate more data on our platform. That’s one of our cores strengths right now. Not only can you see SalesForce activity, but you can plug-in your phone system, and import a CSV that has arbitrary numbers to come up with an Ambition score.

We’re pretty bullish on the future. There are a few people in the sales productivity space, and it is definitely going to be a fight for market share. One out of every three employees is a millennial and in ten years it is going to be three out of every four. We are the first generation to grow up with the internet, and are the first to grow up expecting interactive, real-time experiences.

“Businesses can either engage millennials and drive productivity, or they can complain about us and get the same results.”

Right now the industry as a whole is growing 70 percent year-over-year. For most the word gamification has been played out, but in enterprise it is taking off, and larger companies are starting to realize they need to allocate a budget for this.

We just raised a couple of million dollars from V Angel, Google Ventures, High Line, Redpoint Ventures, Promus and a few others. They are excited to work with us and get us to the next level.

It is going to take a lot of mistakes and a lot of pain, but in a few years I think we’ll be the leader in the space.

Speaking of mistakes and pain. What are some errors you’ve made so far?

Crazy, I was actually having this conversation with someone today.

Sometimes the best deal you can make is to walk away from a big customer.

Early on we said “Yes” to more people than we could handle. It let them define our time and our scope. Obviously in the beginning you have to cater to customer needs, but we found ourselves spending 80 percent of our time doing maintenance work on custom things we should have never built in the first place.

That was not what a startup should be doing. We should have spent 20 percent of our time maintaining and 80 percent of our time building and onboarding.

Going further back to our first startup, me not being technical and trying to build a technical team was a mistake.

I’ve underestimated how long things are going to take. As a sales guy, it is easy to over promise. In previous lives it was easy for me to over deliver, but when technology is your bottleneck sometimes things take weeks or months. At times we’ve had to go back to potential customers and tell them that we can’t do what we said we were going to do. That’s always tough, but they are lessons learned, and we’re better for it.

If I sat down and made a list, there would be hundreds of mistakes. They’ll in my memoirs.

What happened with those early customers you were spending so much time on? How was that resolved?

One of the hardest things I’ve had to do in my life is let some of our customers go.

As a startup, that is the worst feeling in the world. We had to tell them that we could not scale the work that we’ve done for them, and that, quite frankly, we need to end this relationship. It hurt, and we had to watch our revenue drop.

One of the customers that turned down came back to us and asked “how do we need to organize our data, or what systems do we need to use to make this work?” Things like that are exciting, because maybe we are onto something that is going to change the sales team. We’re seeing relatively slow-moving companies start to see that it is worth it.

Thanks for sharing. I find that interesting, because you think startups need to get all the revenue they can.

Travis, who do you look up to?

Good question.

I have a lot of mentors back in Chattanooga. They are brick and mortar guys that decided never to play the investor game, never to play the publicity game, but have built billion dollar companies without taking a penny.

Specifically, I have three mentors: Ted Allen, Allan Davis and Barry Large. I also look up to guys like Randy Redberg who started Experts-Exchange with no investment money.

The Y-Combinator experience was pretty special. It was great to be able to surround yourself with people that have been making fantastic salaries with incredible benefits at some of the greatest companies in the world—those people that gave it up and decided to suffer for a couple of years working on a startup.

Also, the Y-Combinator partners that have already had incredible exits and are set for life, but decide to come back and do it again.

Anybody that hustles, I respect.

“One of the hardest things I’ve had to do in my life is let some of our customers go.”

Do you have any last comments or advice?

I’ve been privileged to speak at a couple of college classes, and one thing I like to talk about this imaginary line where you cross the world into entrepreneurship. In college I came close to that line several times, but always found a reason not to do it.

As I’ve grown older, I’ve realized that with every day that goes by, you’re going to come up with a reason not to do something. As cliche as it is, just cross that line, go all in. If you’re passionate about it, just do it.

For me it took a lapse in judgment to surrender my life insurance policy. You don’t need to do something that extreme. Just remember with every day that goes by, you miss the opportunity to do something crazy, and a startup is certainly crazy.

Where can people find you?

I have a small Twitter presence. You can find me @TDTruett. Feel free to email me, I like to pay if forward.

If you find yourself running a sales team, or are part of a sales team, checkout ambition.com. You can test-drive our product on the site, and if you’re interested we can spin you up a pilot.