You wrote on your blog that a few years out of undergrad, you were disillusioned in your job, were rejected by several MBA programs, and couldn’t get a response to your job applications. Within a matter of four years you got a job with a startup (IMlogic), an MBA from Stanford University, and a job offer from Boston Consulting Group. How did you pull that off?
I think it was equal parts luck and hard work. I got the job at IMlogic through a lucky break, as a result of networking with friends and family. The opportunity was a little unorthodox at the time. The company had only 8 people in it and no shipping product; back in 2002 it wasn’t so popular to join such startups. It turned out to be a really good decision. The company did really well, and it was a great opportunity to wear a lot of hats, and I worked with great people and learned a lot.
The CEO of that company is still a friend and a mentor. Having a good mentor made all the difference in the world. He was accomplished, he was humble, he was very bright – I learned a lot from him. When it came time to apply to business school, he was one of my recommendations. I think that really influenced my ability to get into Stanford.
When did you decide you wanted to get into consulting?
I had always been in tech and had gone to school to be an engineer, so I thought it would be really nice to get into different industries and see if there was something I might like more than tech. I thought the idea of strategy consulting sounded cool and prestigious. I should have had better reasons for joining, but nonetheless it was a good experience. However, it ended up not being the thing that I wanted to do for the rest of my life.
The people who stayed in strategy consulting tended to be people who wanted to be advisors as opposed to operators. It’s sort of the big decision that many people will make in their lives: Are you an operator, or are you an advisor? When I got into consulting I realized I was more of an operator.
After 2 years and a promotion at BCG, a Raines International recruiter called you with an opportunity to be Vice President of Infrastructure for SunGard Availability Services. How did you decide you were ready to leave consulting, and what drew you to that particular role?
They say that after two years in consulting you’ve learned the foundations, and fundamentally I knew I didn’t want to go on to be a Partner. As great as BCG is, if you know you don’t want to be a Partner, you should pull the plug sooner rather than later and move on.
I had never considered SunGard prior to Raines International contacting me. I was looking at smaller startups, and SunGard is a large, private equity-backed tech company. It was an opportunity to manage the real estate investments for a data center company, as well as build out data centers, so it was a very interesting intersection between finance and engineering. It was a weird combination but simply amazing. To date it remains the best job I’ve ever had and the most fun I’ve ever had.
What did you learn from your role at SunGard?
One of the big things I learned was what it really meant to drive strategy. I did strategy consulting for two years, and while I understood it in the terms we would use at BCG, I didn’t really grasp how hard it is to get it right, even when it seems to make logical sense. And if you get strategy wrong, it is really hard to recover. Sometimes you might even get it right, but your timing with the market is off and that makes all the difference. Strategy is not just spreadsheets and a pat on the back after a series of good meetings. It is a really long-term decision that may cost hundreds of millions of dollars. That was my biggest takeaway from SunGard.
After a few years at SunGard, a connection from IMlogic helped you land a role at HubSpot as Vice President of Business Development and Partner Products. How would you describe your experience at HubSpot?
I’m working with an outstanding team, on an exciting product, in an exciting space. I was part of the senior management team for the first two years, and I think a lot of them are some of the best in the industry. And I’ve finally gotten to learn sales, which is something I’d never done. I want to be a successful all-around operator, and my boss is fond of saying “you either build it or you sell it.” I’ve built things but never sold them before now. I’ve had quota-bearing people report to me, I’ve taken sales coaching, and I’ve done several deals as part of my Business Development responsibilities. While there’s still a ton to master in sales, I now feel more confident in this function.
How would you compare the consulting culture to the private equity environment and to the startup world? How is your work-life balance?
Culturally, the three are very different. I don’t think I really knew what “culture” meant until now. A private-equity backed company is not a cultural fit for me. In most cases, it tends to be a lot of older folks who are skilled at financial engineering and squeezing marginal gains from a company versus innovating on products and solving new problems. While I like finance and operations optimization, I love building products more – so it wasn’t a great fit. I learned a lot and I don’t regret my time there, but I realize now that it’s not a perfect cultural fit.
In consulting, I really liked the people and even the work for what it ostensibly purported to accomplish, but I didn’t like the lifestyle. I think it’s unhealthy. I’m married with a kid now and I would never contemplate living that way, no matter how exciting the work is and how good the pay is.
A startup job is a good gig, I really like it. The downside is that you’re flying by the seat of your pants and doing multiple jobs that you don’t always have experience in. Sometimes there is not a lot of process, or you’re not sure whether the next round of funding will come in, so it can be stressful. At BCG I was stressed about performance, but here I’m stressed about successful outcomes. Is the company going to do well enough to keep going? I never had to think that way at BCG. And even SunGard was such a big company that it would’ve been difficult to really screw it up. In a startup you actually can potentially really screw things up.
From a lifestyle standpoint, hours are long but not crazy long, and it’s more flexible. My work is always on my mind, but I think that happens to a lot of people regardless of industry. You have to learn to disconnect and recharge. One thing I do is avoid checking anything digital after 9pm. I’m pretty good at taking walks at work away from my desk so that I’m not constantly staring at my screen. I think the workaholic culture isn’t specific to startups, and it takes discipline to set boundaries.
What are the key criteria to determine whether a particular startup will be a great career move? How can one filter out the “bad” opportunities and feel confident that a startup will be a step forward?
Truth be told, I don’t think there’s a great formula on this. If there were, you could just invest in those companies rather than joining them. Frankly, you should just go into a startup expecting it to fail, because that’s actually the most realistic outcome. Then ask yourself, “If this fails, do I still want to do this?” If you’re doing it because you want multi-million dollar outcomes, then you’re delusional because that’s a highly unlikely outcome. If you’re doing it because it’s a great team, the product is interesting, the space is exciting, and you’re going to learn something that you’ve never had a chance to learn before, those are good reasons to do it.
Once you have all that figured out, pick companies that are backed by good VCs – that’s usually a sign they know what they’re doing. Go with a management team that has been successful at least once before. At least one person on the management team should have experienced an exit. If nobody has seen an exit before, they’ll have to learn everything the hard way, and that’s tiring.
You created a blog, curiousjuice.com, to share some of the career advice you’ve been given over the course of your career thus far. What would you say are the two most important lessons you’ve learned from former bosses?
One piece of advice is, “Don’t be cynical.” It seems really obvious, but it’s really important as a manager or a leader of any kind. You don’t have to be perenially happy and positive, but being cynical can bring people down in ways that you may think is funny, but it’s not.
The other advice is, “Don’t be in a rush to become a manager.” There’s something amazing about being an individual contributor, whether it’s carrying a sales quota or designing a product – you’re the person that’s driving the company. You may be driving a small part of it but you’re actually driving it. Management has so much overhead, and they make decisions that steer the company, but they don’t drive it. You shouldn’t be in a rush to get to that point. In the last ten years I, and probably a lot of my peers, have been obsessed with titles and salaries. But really the higher the title and the more the compensation, the further you’ll be from driving the ship. You’ll be in a bureaucratic layer steering it, and I don’t think that’s always fun.
I’ve learned some things through my own experience as well, like understanding the politics of decision-making. Any large group of humans will have politics. That’s just life. It’s not bad, it’s not that people are evil, but you do need to know how to work in it and how to play the game. Anyone that decries that and says “no, I want to work in an environment that is devoid of politics and is a pure meritocracy” is delusional – it doesn’t exist. So that’s one of the more profound things that I’ve learned over the last couple of years.
On your blog, you say you’ve had the good fortune to work for companies that were devoted to the success of their employees. As current consultants consider roles outside of consulting, how should they evaluate that a company will invest in their success?
Consulting firms in particular tend to be really good at developing talent, because their primary asset is their people – that’s what they sell. The training at consulting is unbelievably good. It’s the main reason I don’t regret my time at BCG. The training they gave me is the best I’ve ever received. Huge, huge props to them. There are other companies with formal rotation programs and mentor programs, and they don’t just pay lip service to it, they really use it to build leaders. HubSpot’s sales team does really good sales development, for example.
Look at the company’s website and talk to former and current employees and ask about training. If they just tell you “oh yeah, once a month we have to go to a class,” then you know it’s bogus. But if they say “it’s an intense immersion for the first month, and you have tests and exams and periodic certifications, and you really use the product,” et cetera, then you’ll know the company is committed to training.
What is next for you?
Frankly, I don’t know that my next move is going to be with a company that is super well-funded or with a highly experienced management team. It might be that the company’s mission and product are just so connected to me that I’m like “to hell with it, I really want to do this, I’ll sink five years into this. And as long as it pays at least x, then we won’t be destitute,” and that’s it. And then I’m not really set up for disappointment.
As far as a long-term plan… I have a completely unrealistic, financially unviable long-term business plan for a startup. So I probably need to make some money before I do it. Another idea is to go back to grad school, maybe teach mathematics at a community college. I know it’s a little trite to say that… it sounds like I’m in Good Will Hunting or something. These are just two ideas. Neither is going to pay well, but it may be fulfilling in other ways.