Prior to business school, you helped start an import/export business in Chile, followed by helping to launch a new retail business in Madrid for General Motors Europe. Was business school always part of the plan?

I moved to Santiago, Chile when I was 22, and at that point, I just wanted to learn Spanish and experience a new culture. I probably would have done anything (teach English, etc.) but I ended up convincing someone to let me work for free and help him start an import/export business. We imported parts for cars…it was about the least sexy job you could have, but this guy gave me a chance, and I ended up having this amazing experience. I learned Spanish really quickly – which is honestly probably what inspired me to start a language learning company years later – but he also convinced me that getting sales experience early on in my career was really important. During my time in Chile, I ended up meeting an executive for General Motors while I was trekking through South America, and he offered me a job as a District Sales Manager in Madrid. I was 24 by that point, and it sounded fun to live in Madrid, get an expat assignment, and to continue to learn how to sell. I ended up doing that for three years.

It was actually between Chile and moving to Spain that I decided I wanted to go back to business school. It wasn’t in my plan when I graduated undergrad (I was a little bit sick of school at the time), but I had just had this very interesting experience in Chile, and knew I was about to go do something else really interesting. I thought it would make a good business school story. Also, at that point in my career, I was incredibly sales-oriented – I was selling container loads of overpriced car parts to people who didn’t speak my native language. I could sell ice to Eskimos, but I wanted to get some of the harder skills that business school offers in the study of finance, analytics, etc.

What drew you into consulting post business school? At Booz & Company, you primarily advised consumer and media clients. Did you seek that out, or was it something that just happened?

I’ve always had a strategy with how I approach my overall career, and at that point, I had already gotten sales experience (to the point where I thought I was too salesy) and had strengthened my analytical skills in business school. Next, I decided that I needed to generalize my industry knowledge because up until then my career had been very industrial with my automotive experience. If I did want to go into media, technology or any other industry, I thought relevant experience would be a hard sell, and that consulting would be a great way to rebrand my industry focus based on which projects I liked best. Throughout my first few projects I managed to befriend a partner in media – so I guess opportunistically I chose media, but strategically I was going for anything but automotive. After a few projects, I was able to curate my own history, so to speak, with a focus on media, pulling from projects with CPG, media, and spirits clients in New York.

You left Booz & Company after three years to join Virgin as a Director of Corporate Development. Were you looking to leave consulting at the time?

When I started at Booz, I was very focused about how this would impact my overall career. Within the first week I had a personal CRM set up and I started cataloging every recruiter who contacted me. I’d get voicemails every Friday and would keep track of who called. I actually started interviewing for jobs at the end of my first year, even though I didn’t want to leave at that point – I wanted to get promoted first, to increase my market value. But I proactively and strategically wanted to develop a network of recruiters to be able to utilize when I did want to leave, and the recruiter who got me my first interview at Virgin was someone I had actually already known for a year and a half through that process. I passed on a lot of lousy jobs before the one at Virgin came along.

What set the opportunity at Virgin apart from others you had looked at?

Truthfully it was getting to work at Virgin itself. I had read Richard Branson’s Losing My Virginity right before business school, and he was, and still is, a hero of mine. So at the time, when an opportunity at Virgin came up, I wanted the job more than anything.

As for the process, I’d had over 30 interviews with Virgin, and they had stopped returning my recruiter’s calls (I even paid for my own flight and hotel for my last round of interviews). This may not be a lesson for everyone, but when I was told I likely wasn’t getting the job, I called Virgin’s then CEO and said, “I think you’ve made a mistake. I’m perfect for this job.” She gave me an offer an hour later.

At Virgin, you helped conceive, fund, incubate, and launch Virgin Hotels. What was that experience like, and what were some of the largest differences you noticed in your transition from consulting (culture, responsibilities, etc.)? What did you leverage from consulting in your new role?

I was a Principal in Virgin’s Leisure and Hospitality Group, and the structure there was like a private equity or “branded” venture capital firm. One of the first things I was asked to do was look at the hotel industry. We all got in the room Monday morning, and the CEO told me to start thinking about hotels, so I downloaded Marriott’s 10-K and started tearing it apart and building a PowerPoint. And that’s still what I do to date – get smart about something through research, build a story or thesis in PowerPoint, fill in everything I can with data/evidence, and use that to convince people – to buy products, buy equity, take the job offer, etc. Essentially, buy the idea. That’s just my personal sales style (everyone has their own), but it tends to work with Boards of Directors, just like it does with consulting clients, just like it does with teams when you need to convince 40 people that they should all want to do a certain thing in a certain way. So I would say the research skills of consulting translated perfectly into both venture capital and starting a company, as did structured thinking and communication – being able to pull people through a thought and crisply argue and articulate what you want.

The part that I wasn’t as prepared for was the amount of banker knowledge that was required in that corporate development / venture capital role. Consultants tend to be more focused on the P&L, whereas investors have more of a focus on equity value. I remember in my first couple of months at Virgin during the first deal I was working on, I put a free cash flow multiple on an EBITDA number – which means I was off by 30% in the valuation because it doesn’t account for taxes – and that was because I didn’t have the banking background. So it took me a bit to come up to speed on financial concepts, term sheets, and legal jargon. But now, I find all of that stuff very exciting – figuring out venture math around equity value, what’s going to really drive shareholder value. How things like top line growth, quality of revenue, strategic positioning will translate to more meaningful businesses.

In terms of the results you need to deliver, consulting and investing are very similar in a sense compared to being an entrepreneur. Here at Voxy, one the scariest days of my life was the day I realized I had to actually go do it all. I was so good at PowerPoint that I raised my first round of capital off of just an idea – so I had $600k in the bank, no tech guy, no product, and no prototype. I had nothing except me and this PowerPoint presentation, and then I quit my job and had to go make it all happen.

At what point in your career did you know that you might want to have your own company some day?

I pretty much always knew I wanted to be an entrepreneur. My dad was an entrepreneur and owned a chain of pharmacies. By the time I was 12, I had started a lawn-mowing business and was typing up brochures and distributing them all over the neighborhood to convince my neighbors to hire me.

You left Virgin in 2010 to start Voxy, a venture-funded learning platform that uses mobile and web technology to teach English to people in developing global markets. How did you get started?

A big part of being an entrepreneur is getting off the starting line and just making things happen…you might flail around a bit, but nothing is more important than forward progress. The critical skill of an entrepreneur is taking that first step because that’s the scariest and the hardest thing to do. It’s also the one that so many intellectuals and bankers and consultants would love to avoid, because why do that when you can think about the problem for a lot longer? But companies don’t get started by just consuming content and reading and analyzing and thinking about the problem, and then thinking through it some more. They aren’t built by just making a PowerPoint presentation. Companies get started by going to LinkedIn, finding a developer, and convincing him or her to leave their job to start writing code for you. Or when you get out and get your prototype in front of users and watch them use it. In the first months of Voxy, I would go out to Sunset Park (a Hispanic neighborhood in Brooklyn) and do paper prototypes with Hispanic immigrants. I would approach people outside of a church on Sunday afternoon and offer them 20 bucks to talk to me. Their ideas became the foundation of my first product.

How did you balance working on Voxy with your full-time jobs at first?

When you first become a consultant, you’re really overwhelmed and it takes you forever to do things correctly. Then you learn how to do everything much better and more efficiently. As I got more efficient in my job, I built in time to do job searching with the same intensity that I would pursue a typical consulting project. You have to keep some of the productivity gains you start to see over time for yourself and your longer-term career goals.

At Virgin it was the same thing – an intense job with super smart people, working 60+ hours a week. And then in my few hours of free time at home, I would pour over the Rosetta Stone 10-K and do all of the primary research for Voxy, just like I did with the Marriot 10-K at Virgin. I treated Voxy like a long-term consulting project that I did in my free time, every Saturday and Sunday 12 hours a day, and every night of the week. I didn’t go out at night. There’s always overlap, and I think you have to parallel process like that to make transitions smoother. Time allocation is just so important. You should also do something that you’re passionate about. This is not a knock on consultants by any means (many of them are my friends), but most consultants tend to be more intellectually and financially motivated, and those are great things in order to get rich and enjoy thinking…but alone do not lend as much to creating meaningful and long lasting businesses.

Who did you go to for advice when starting Voxy?

I honestly didn’t really know who to go to at first, but part of being a consultant is being resourceful. One of the projects I did at Booz was for a drill bit manufacturing company, and I had to call all of these oil rig operators to figure out if they liked drill bit Type A or Type B. I would catch them in their pickup trucks driving across Texas and ask them what they thought of the certain type of drill bit, and then I had to piece together all of the information to try to make something cohesive. That’s still what I do today – pick up disparate data where I can. It’s all about being scrappy.

For example, I found my Chief Education Officer – literally the world’s expert in second language acquisition and an incredible asset to Voxy – through a VC who passed on Voxy in the second round of funding. She was advising them and happened to really like Voxy’s approach. I had already had conversations with 15 or so academics (I had even interviewed the grade school Spanish teacher of one of my friends) and reached out to her. She was clearly the best person I’d ever spoken to about English learning, and it took me two more years to get her, but it was worth it.

Off of that point, how did you select your executive team? What were you looking for specifically as you selected your executive advisers and board members?

Building your team is one of the hardest parts of starting a company, and I’ve tried every idea imaginable to win the war for talent… cold-emails, targeting bloggers using their info@ link on their site, meeting people at events, joining online communities, etc. I got my first two employees that way. My best friend is my co-founder, and he came in at around month eight, and as I mentioned before, it took me two years to recruit my Chief Education Officer, who has a Ph.D. in the subject matter that I needed. You also turn your team a lot in a startup. I’ve had multiple CTOs over the years, and I finally have a Chief Operations Officer who I love – a seasoned operating executive who has built many companies and managed many large teams. He can handle the scaling challenges we have now.

The other challenge is that in a startup, most people are working for free in the beginning. One of my first investors was Doug Levine who founded Crunch Fitness, and he told me when I started “no one who is as smart as you would ever work for you right now, because what you’re doing is so fundamentally high risk and likely to fail.” I would talk to him at least once a month about the progress and I’d say, “I got this great guy!” And he would say, “No, you didn’t, because if he was that great he would never work with you right now. You don’t have a company name, you don’t even have a product… why on earth would this guy come work for you at this point?” It was a fair point. But after a while, our mission really started to attract people – if there are two billion people that need your product or service, that’s a pretty good place to start. And learning a language is one of the most highly correlated variables to socioeconomic advancement, so that’s a good feeling too.

How instrumental was your Virgin experience to starting Voxy versus having pursued a startup directly out of consulting?

My Virgin experience was hugely impactful. It took more abstract elements, like advice, and the focus on one dimension of business like revenue and cost, and very much expanded my whole way of thinking in terms of larger-picture business and ownership of a company. There were so many venture-capital specific elements I learned, like understanding dilution, shareholder rights, the supply/demand fundamentals of early stage capital markets, how preferred equity can crush the common stock (which is all the Founder has), etc. And that knowledge became my secret weapon when pitching because I knew how to speak the language of the investors. You need that type of differentiation to set yourself apart from just being another smart business person. VC language was my trick, but if you don’t have that, being a programmer or having another unique skill to leverage is important.

You went from a team of one to a team of over 40, including seven people in São Paulo, and you now have $20 million in funding with your round B funding last July. What have been the biggest lessons, and what pitfalls have you experienced?

Being an entrepreneur is mostly about resilience. A lot of smart people that go to top business schools and top consulting firms are generally risk averse. There’s a good Conan O’Brien quote that says, “Success is a lot like a bright white tuxedo. You feel terrific when you get it, but then you’re desperately afraid of getting it dirty, of spoiling it in any way.” At the end of the day you fail so often with a startup. The biggest lesson I’ve learned from Voxy is that I’ve messed up absolutely everything at least once, and I’m still here, because I can either lick my wounds, sit there feeling sorry for myself, or I can get up, realize no one really cares about excuses and try to find another thing that will work. It’s all a huge trial and error and it takes mental fortitude to get through all those errors.

As far as pitfalls to avoid…there are so many. A big one is thinking you know all the answers. Consultants are all about structured thinking, but sometimes you can get so fixated on your idea by proving it to yourself a hundred times – in your office, in the shower, etc. – that you can convince yourself you’ve found the absolute right answer. You need to be flexible enough to realize, “Wow, I totally missed this, and now I have course-correct if I want to stay alive.”