You spent three years at BCG pre-MBA, and then another four years at the firm, leaving as a Principal to join Motorola as the Director of New Multimedia Products. Were you looking to leave consulting at the time? What other opportunities had you considered, and what set this apart?

I felt in my gut that I didn’t want to be a consultant for the rest of my life. I wanted to work in a company that was growing quickly or aspired to grow quickly, and I wanted to not have a strategy job.

I had a perspective that if you are going to do strategy-oriented work, it’s probably better to work at McKinsey or BCG or Bain than to do it on an internal basis at a company itself, because you tend to not be able to take many risks in your recommendations, and sometimes the projects aren’t as interesting.

My goal was to be able to build a little bit of operating experience as a result of leaving, and I wanted to work at a company that was growing. I figured that this was an investment in the long term, so it wasn’t a matter of getting the perfect job or getting the perfect salary – or even the perfect company. It had a lot more to do with working in a growth industry and being able to diversify some of the experience that I had gotten at BCG.

After Motorola, you spent over three years with United Airlines as Managing Director, Mileage Plus. Clearly, the role influenced your career going forward (we’ll talk about that later), but how did you become interested in the travel industry?

I’ve always been interested in travel. I think many people would probably say the same thing. I’ve done a lot of travel in my life. I had gotten exposure to some of the loyalty programs – frequent flyer programs and hotel programs – as a result of traveling for BCG, so I was really curious about the psychology of how those loyalty programs worked and why people make different purchasing decisions. So it felt like a pretty good move to go in that direction.

I was particularly interested in United at the time because they were evaluating spinning Mileage Plus off into a separate business altogether, and I thought that was an opportunity to be part of what could have been an iconic shift in the company. When a big change like that is coming up, it’s helpful to have people who have very versatile skills, so I probably got a little bit more responsibility as a result of going to United, and I had a nice P&L responsibility there.

How did that opportunity come about?

It’s a little bit crazy – I was interested in working in experience design and product design, and the job I had at Motorola was basically to do the assortment planning and figure out which phones Motorola should be building in the future, and I wanted to continue in that vein. I was introduced to a woman who had recently joined United from Disney, and she was responsible for improving the customer experience at United. She told me there was an acute need at Mileage Plus and introduced me to some of the folks there, and I thought it would be an exciting, higher risk, higher return opportunity.

When I left United, I had been there for three years and had some commercial success. The scope of my responsibilities had changed a fair bit, and I felt like we had done a good job of building out an effective team. Those things were quite different from the experience I would have gotten at BCG. I felt I had put points on the board for United as well as for myself, and I was looking at the upcoming years and thinking that they might not be as exciting as my first three years. This is partially because I tend to get a little restless in general, but also because United had merged with Continental. When two big companies merge together, there are a lot of career opportunities, but a lot of it has to do with politics and cost-cutting and process-oriented things. I’ve always been interested in building new businesses or launching new products, and when you’re merging two companies you just don’t have the capacity to do those types of things.

You left United Airlines to join Groupon as Vice President and General Manager of New Business, where you stayed for a little over a year. What did you learn from that role?

I had a great experience. Groupon was still pre-IPO when I joined. Obviously, the company has invited a lot of scrutiny and opinions. One thing that is independent of any of those opinions is that they built a company extremely quickly, and they were in the market for people who could build additional businesses. That felt like a pretty good match for what I was doing. I think that if I had been invited to go work at Groupon in a Sales position or with the daily deals business, it wouldn’t have been as attractive. But the role that I was invited to do there was to basically use the existing platform to go out and build new businesses. I felt it was worthwhile to get some credibility at an e-commerce company, and a company that aspired to grow by 50% every year instead of by 5% every year. I thought that even in the worst case scenario, I would be practicing a new sport altogether and I would learn something as a consequence of being there.

It worked out really well in that regard, and I had the chance to help build two new businesses from scratch in a year and a half. I think that if I had launched Rocketmiles – my current business – right after BCG or right after I left United, it wouldn’t have been successful. Part of the success that we’ve had is a function of my understanding what a fast pace really feels like, and also interacting with a different set of people than you tend to find in a consulting firm or in a gigantic corporation. I know how to do some big company stuff, but I’ve also had the chance to work with people who have started things from scratch – which is a different skill set altogether.

As you mentioned, you left Groupon in 2012 and cofounded Rocketmiles, a startup travel rewards program that was acquired by the Priceline Group in February of this year. In a 2013 interview with “Inside Flyer,” you said that Rocketmiles was, in some ways, an idea you had been thinking about your whole life. How did you know it was the right time to leave and fully commit to Rocketmiles?

You never really know for sure. It’s kind of a matter of a feeling more than anything else. I had gotten some stuff done at Groupon that I was proud of having accomplished. I felt like if I was ever going to do it, then this was the right opportunity to do it. I had the right combination of a good idea and a good team. I decided I was going to budget a year to give this a go, and the worst case scenario would be that I would have an interesting life experience. The best case scenario would be that I would build a successful company and a good experience for my team.

In the first year, what were the biggest lessons, and what pitfalls did you experience?

First, I think you need to be a little bit irrational to be an entrepreneur. The numbers suggest that you are going to fail, and if you’re in your mid-30s and you’ve got a decent-paying job, it’s not a rational economic decision to be an entrepreneur. If you don’t realize that, you’re bound to be disappointed. I’m also a bit idealistic. I’m sure every entrepreneur thinks that their idea is brilliant enough that it’s practically going to sell itself, and everybody’s going to find it, and you probably won’t have to do any marketing at all. That’s not the case. I think we’ve got a really good product that is relevant for a lot of people. I feel proud whenever anyone makes a booking with us. But there’s a ton of work that you have to do to engender trust in your customers, and that just takes hard work. I think we had a good idea, but the marketing aspect is hard work.

Another thing is that the ups and downs associated with being an entrepreneur are much more severe than any other job I’ve had. Working at BCG is a hard job, and I worked hard at Motorola and United, but it pales in comparison to the ups and downs that you experience when you’re starting something from scratch. We had a couple of days two months after launch where we put up goose eggs and nobody made a booking on Rocketmiles. We sat there wanting to call our friends or our moms to make a booking just so that we didn’t have a goose egg. It was just heartbreaking to have those days. But as a result, you appreciate when things go better.

There’s something different about starting something from scratch. I had noticed it at Groupon with Andrew Mason, the founder. I think that there was a little bit of a caste system for people who were there in the beginning versus those of us who came later on. There is a different level of bond and a different level of empathy that goes along with what I just described: experiencing the days, two months after launch, when nobody made a booking on the site. That makes you humble and gives you a kind of empathy for what other entrepreneurs are going through.

In a 2014 interview with “Bootstrapping in America,” you said your strategy from a team perspective has been to hire the best folks. And you have mentioned before that it’s important to find ways to work with people who have different/better talents than your own. How did you select your team?

I think it was important to have some shared values, like the way you want to treat other people and whether you’re building a system of intrinsic motivation or extrinsic – financial – motivation. You need to make sure everyone has a common definition of success.

The second important thing was having people with different capabilities and different strengths than the ones that I had. I knew the travel arena well and had some relationships in that area. I was pretty good on the airline side of things and had some product muscle memory. But I had never built anything from scratch. My two co-founders had a little bit of travel experience, but they had experience starting companies from scratch. It’s just a different set of skills. One of the two co-founders, the Chief Technical Officer, was the best developer I had ever worked with. We had all worked together at Groupon and had gotten to know one another there, and had been through some good times and some tribulations there, so I think we had a pretty good sense for our working styles. Picking who you are going to work with is an awfully important decision.

And after that, in contrast to what big companies and consulting firms do, I really buy into the idea of inviting people to start doing the job before you hire them. You can do that in an interview process, or you can do that by inviting someone to be a contractor. I feel like you learn a lot more about somebody that way, in terms of both skills and effort level. So to fill out the rest of the team, for example, we had a designer who did some part-time work who is now our Head of Product. We had a guy who was writing some copy for us who now runs all of our Customer Experience team. In each of those cases, we had a chance to get to know them well on a rent-to-own basis. It worked out well. I think they would say the same thing – they had a chance to see what the work was like and what the culture was like.

Your team is spread out over several cities – how does that impact the culture of the firm?

My two co-founders are in different cities. If we had never worked together before, that would have been a very big detriment. But the fact that we had worked together before made it work. In the early days, I was spending quite a bit of time with them building the product, so I would travel to San Francisco or they would come to Chicago. I thought to have A-players was more important than having everybody in one building. That has made it hard from time to time, but overall it has worked.

The Priceline Group says it prefers its acquired companies (which also include OpenTable, Booking.com, and Kayak) to continue to function as independent entities. With that in mind, have there been any significant changes in the way Rocketmiles operates?

Priceline has a philosophy on this because they have been extremely successful with previous acquisitions. Their blueprint is to keep the companies really independent, and their belief is that you get a lot more out of the autonomy and the entrepreneurial spirit than you get out of the synergies of the companies working together. There are a few things around the edges – for example, we’ll get some hotel supply from Priceline Group – but other than that, we act completely independently. And I think that’s a good thing for the team.

Is there anything you wish you had known prior to the acquisition?

I think some of the fun of it is that you don’t know and that you have to make decisions rapidly. You have to give yourself a chance to fail and to fail five times before getting it right. The biggest thing that I learned that I would carry forward to whatever I do next would be around pace, and getting stuff out as quickly as we possibly can. We’ve hired a couple of consultants recently, and it’s fun to coach them to do less in PowerPoint. We should be pushing things out and testing them, rather than spending a lot of time thinking about them or doing surveys. In this world – a scrappy, ultra-competitive startup environment – getting stuff out there is always a better solution than spending a whole bunch of time thinking about it and making sure that you’re covered if things go wrong. We might be able to get six things done this month, and maybe none of them will work, but it’s better to know that now than to sit on it for two or three months, which is what tends to happen in larger companies.

What advice would you give to current Principals who want your job someday? How long should they stay in consulting? Is there anything you wish you had known back then?

I think consulting is really good as a way to build an analytical toolkit and communication skills. I think that the quality of the people you work with – both the raw intellectual horsepower and, in many ways, the creativity – is unsurpassed. But if you want to do something yourself and get your hands dirty, the very best thing you can do, in my opinion, is to find somebody five to ten years ahead of you, who maybe spent a year or two in consulting, and find a way to work with them. Soak it up for a year, and figure out whether you like the entrepreneurial environment. Put yourself in a challenging environment, independent of compensation or title, and just find people that you’d be interested in learning from, who will be hard on you and help you make the transition from trading in intelligence and communication to actually getting things done. The best advice, put simply, would be to reach out to the alumni network and find people who have gone out and done interesting things post-consulting. Find someone who is five to ten years ahead of you and tell them that you’ll do whatever they want you to do as long as it has real accountability.

Of all of your professional experience, what experience was most instrumental to your success at Rocketmiles?

I take something from all the experiences that I had. I do still think of my formative years at BCG as being an era that I was really proud of. If it’s a matter of setting a high bar and a definition of what good work is – that’s BCG. If it’s a matter of speed, I would say that I learned that at Groupon. It’s really hard for me to say that one of them was the most instrumental. They all served a different purpose, and they each represent a different phase of my life, so it’s hard to choose just one.