I spent the past two weeks on vacation, eating delicious food, relaxing in the sun, and enjoying my favorite band. I also managed to make my way through two books that came highly recommended from colleagues at TheLadders: Delivering Happiness and The Intelligent Entrepreneur.

Delivering Happiness chronicles Zappos CEO Tony Hsieh’s career from Harvard dorm pizza joint to CEO of a multi-billion dollar e-commerce joint. From the story of LinkExchange, his first company, through to the sale of Zappos to Amazon for $1.2Bn, Hsieh communicates his life philosophy that is ultimately summarized with a final chapter on the “science of happiness.” In it, he describes three types of happiness: pleasure, passion, and higher purpose, that range from the most ephemeral to the most permanent. Hsieh says the following about a higher purpose:

“The higher purpose type of happiness is about being part of something bigger than yourself that has meaning to you. Research has shown that of the three types of happiness, this is the longest lasting…Based on the findings of the research, the proper strategy would be to figure out and pursue the higher purpose first…”

Hsieh closes the book with a series of questions aimed at challenging the reader to take a long hard look at how he or she is spending their time. Here are a few:

“What is the net effect of your existence on the total amount of happiness in the world each day?
What inspires you?
What is your higher purpose?”

The Intelligent Entrepreneur tells the story of three Harvard Business School graduates from the class of 1998 who found success as entrepreneurs: Marla Malcolm, co-founder and CEO of bluemercury, Chris Michel, founder and former CEO of Military.com and Affinity Labs, and Marc Cenedella, founder and CEO of TheLadders (and my boss). Author Bill Murphy Jr. distills out of their stories common themes that culminate to a list of “ten rules” of successful entrepreneurship (which you’ll have to read in the book). If you’re a wannabe non-technical entrepreneur like me, this book is required reading. The three stories are inspiring and Murphy’s analysis is well thought out and concise. Like Hsieh, Murphy ends the book with a series of questions, challenging the reader to take a critical look at what motivates him or her:

“So now it’s your turn: Why are you here? How do you define success? Why, finally, do you want to become an entrepreneur?”

Since graduation two and a half years ago, I’ve thought often about this last set of questions, but the stories of the three entrepreneurs in The Intelligent Entrepreneur, and the language that Hsieh provides in Delivery Happiness, help frame my thinking in a different light. I’ve structured the remainder of this post into sections that best express my current thinking on these questions.

Alone on the mat

I used to wrestle in high school (pause for laughter). I was not the most talented, nor the strongest, nor the quickest. Wrestling is an individual sport – perhaps the most individual sport. It requires commitment both on and off the mat - I cut 5-10 lbs every season and had to maintain that weight for the length of the season, while burning more calories than ever in the most intense workouts of my life. This meant dinners of salads and peanut butter sandwiches, snacks of hollowed out hard-boiled eggs with cottage cheese inside, and many hungry nights. On the mat there is only you and your opponent. Nothing else. You win and lose by the extent of your commitment at that precise moment and all the moments leading up to it. Bouts are won and lost by the slightest of additional effort, when you can’t possibly put any more effort forward. When you lose, that pain is yours alone to carry, and when you win, that glory belongs to you and you alone.

What I see in entrepreneurship is an opportunity to extend this dynamic into my professional career. Entrepreneurship is an individual sport. Other people are critical to your success, but at the end of the day, the entrepreneur is responsible for selecting those people, and getting the very best out of them. In The Intelligent Entrepreneur, you’ll read about how Marla, Chris, and Marc, faced significant odds alone. Sometimes they won and sometimes they lost. In every case, they won and lost by the quality of their own decisions, and had the opportunity to identify how those decisions could be made better in the future. Confounding factors like “my teammate didn’t pass me the ball” or “my teammate passed the ball at just the right time” don’t exist in wrestling, and they didn’t exist for Marla, Chris, or Marc. Their success is theirs alone, as are their failures.

Something from nothing

In 2010 I tackled Atlas Shrugged and The Fountainhead by Ayn Rand. Rand is a phenomenal story-teller, and though I may not see eye-to-eye with her on an economic or political level, I believe that there is a lot of good in her philosophy of the individual. From Atlas Shrugged:

“Whether it’s a symphony or a coal mine, all work is an act of creating and comes from the same source: from an inviolate capacity to see through one’s own eyes…which means: the capacity to see, to connect and to make what had not been seen, connected and made before.” – Ch. II, The Utopia of Greed, Atlas Shrugged

Starting out in business, I felt that it was important to work somewhere where I could have an impact. What I’ve learned over the past two and a half years is that having an impact is synonymous with creating something that you can look at and say, “I built that. Before there was nothing, and now there is something.That thing is there because of my effort, my ingenuity, and my willpower, and it is having a meaningful impact on other people.” While I believe that any career can afford you the opportunity “to see, to connect and to make what had not been seen, connected and made before,” entrepreneurship is, in my mind, the purest and most meaningful form of “creation” in business.

Bigger than me

Tony Hsieh’s notion of a “higher purpose…about being a part of something bigger than yourself that has meaning to you,” struck me in the context of my transition from investment banking to TheLadders. I’ve been fortunate enough to have had two very different professional experiences in a short amount of time. I spent a year in investment banking (you can find my thoughts on that experience here and here) and then 15 months at TheLadders. In my first role, I acted as an advisor, working with a number of different entrepreneurs to fulfill their visions. I was motivated to the extent that I felt like I had a part to play in those visions. My best days were spent sitting across from passionate entrepreneurs who were building something bigger than themselves.

Chris, Marla, and Marc started their businesses with nothing more than their own passion for building something bigger than themselves. Today, each one of them can look to hundreds of people who now share their original vision and higher purpose. Being a part of someone else’s higher purpose is meaningful to the extent that you can make it yours, shape some part of it, and then instill that purpose in others. But to be the source of that original nugget of higher purpose – to see your purpose shared by those around you, then those around them; to see something that you built from nothing taken by others as their life’s higher purpose – is truly remarkable, and is a testament to the awesome power of entrepreneurship.

I’m sure my thinking will evolve in the next few years, but for now I intend to do whatever I can to best position myself for my first entrepreneurial endeavor. In my mind, there is no better opportunity than the opportunity to create your own opportunity.

A few weeks ago I wrote about my experience in Investment Banking and compared it to my experience at TheLadders. I’ve spent one year in each role, which means I’ve only had one year to test the claims that I am about to put forward, so please help yourselves to some grains of salt.

There are no shortage of articles bashing banking, and their authors tend to claim that they tell it ‘how it really is.’

In reality, is can be a lot of different things to a lot of different people. The truth is that in a year of Investment Banking there can be as much value for the young business-person as there is pain, and so as much as I cry freedom for the startup life, I have a hard time recommending that college grads turn down their offers to join banks like Morgan Stanley or Goldman Sachs.

My former Banking colleague Mike Lavalle, who left shortly after I did to start his own business, wrote a great post on the value of Banking to an entrepreneur. I won’t try to speak as expertly to the process of founding a business (because I’ve never founded a business), but I’d like to add a few thoughts on my experience in Banking that I believe have contributed tremendously to a great first year at TheLadders.

Love The Customer

At TheLadders, we live and die by what we call our First Rule: Love The Customer. Our customers are the men and women of the US and UK who earn above $100,000 per year, and we have millions of them. At Morgan Stanley, our customers were the leaders of the most valuable technology companies in the U.S. Over the course of a year in Banking, I had one-one interactions with ~10-15 customers, but the depth of that interaction, and the incredibly high level of expectations for quality of interaction, helped me understand the importance of what I now call the First Rule.

I spent two weeks on the road with the CEO and CFO of a major consumer technology company for their IPO roadshow. We flew all over Europe and US, visiting scores of investors along the way. It was an amazing experience for me, and the level of exposure to two of the most successful tech managers in the world was unparalleled. My role as analyst was fairly rudimentary. I carried the bags, collected the presentations, and coordinated travel logistics. I didn’t care – I would have cleaned the toilet in exchange for the conversations I was lucky enough to have over the course of those two weeks.

Though I added very little tangible value to the transaction, I began to realize that for these customers, for these two weeks, I was the face of Morgan Stanley. The CEO and CFO spent more time with me than with anyone else at the firm over the course of their roadshow (typically an incredibly stressful time for the management team). My behavior and the level of service to which I committed may have had a substantial impact on our payout when all was said and done.

Though the dynamics of the customer relationship are dissimilar, the opportunity to perceive a very real ROI on the work I put into Loving the Customer in Banking helped make the acceptance of the First Rule at TheLadders a natural transition.

Details, details, details

I hate details. Throughout school I followed the mantra “work smart, not hard,” and would rarely check my work after completing it. Come to think of it, even my elementary school teachers hounded me about my attention to detail. A word cloud of my report cards from grades 1-12 would probably spit out ATTENTION TO DETAIL in big, big letters.

In Banking this attitude is tantamount to heresy. I had never before faced the kind of standards to which my work in Banking was held. Yes, it was painful – move this text box one touch to the right so that it is properly aligned with that chart, at 3am on a Friday – but it was incredibly useful. After a year of pain, not only am I now a compulsive checker, but my work tends to be better the first time around.

Managing Up

When you’re working 80 hour weeks, it’s no surprise that time management becomes a useful skill. What I had never heard or thought about was this concept of “managing up.” When you’re at the bottom rung of an organization, you cannot manage time without managing your manager. Your manager may not say it, but they expect to be managed. As an analyst in Investment Banking, this could mean the difference between a weekend in the office or a missed deadline (and therefore a very angry MD). I’ll let you decide which is worse. There is no better way to learn a lesson than to spend a weekend in the office thinking about it.

No matter where you spend your first year after college, much of that year will be spent learning how to send a fax, write an email, and staple large quantities of presentations together in a short amount of time (I discovered what collate meant after a very long afternoon at my first summer job).

One way to make sure you that you learn your lessons quickly is to make sure that those lessons are as painful as possible. Snark aside, should you choose to learn those lessons in Banking, you’ll have a hard time regretting it. I absolutely do not.

Today marks my one year anniversary at TheLadders. I came to TheLadders after one year in investment banking in the Morgan Stanley east coast technology group. Walking in the door on September 14th, 2009, I had very little idea of what I was getting myself into, and my role at TheLadders has morphed about four times in the last 12 months.

Looking back at my experience (or, let’s be honest, the lack thereof) and after fielding the question about 74 times from rising Juniors and Seniors in College, I thought I’d jot down a few thoughts on the similarities and differences between the two experiences. I don’t know if I’ve had anything like a “typical” experience in either case, so I won’t claim that these “lessons” are universally applicable. Still, to the extent that there exists, somewhere out there, someone who is exactly like me, this might prove helpful.

Lesson #1: there’s a difference between business and finance.

Though I knew very little else, one thing I knew for sure coming out of school is that I wanted to be an internet entrepreneur (yea, yea – me and everyone else). I was convinced that going into investment banking, particularly in the technology group, was the best way to get started. Banking promised to open doors, expose me to different types of technology companies at a high level, and teach me the basics of business and finance. Banking met almost all of my expectations.

This is probably obvious to anyone with as little as a few years of experience, but it took me a while to figure it out. Banking taught me how to read a balance sheet, value a company, and build an investor presentation. Banking did not teach me how to inspire and manage a team, how to learn about and build products for customers, and how to identify a market fit for those products. Finance, though an important and necessary part of business, is not business. Though I didn’t know it at the time, equating business with finance is like saying: if you know how to tie your shoes you can run a marathon.

Lesson #2: management and delegation does not equal talent development.

I had a fairly small group at Morgan Stanley – something like 20 people total. The head of our group was a great guy from whom I learned a great deal. The pool of analysts were managed by a “Staffer” who made sure we had roughly equal shares of work. The work was conducted on a project-basis – presentation for client x, analysis for client y. Naturally it made sense for each analyst to own a particular set of clients, and because my group was so small, we each got the chance to work closely with Managing Directors, who owned the relationships with those clients.

Managers at TheLadders spend more time on talent development in a day than I experienced at Morgan Stanley in a year. Analyst programs in investment banking are typically two years stints, at which point most analysts join Private Equity firms or Hedge Funds for better hours and higher pay. The big banks have a really hard time keeping people, and their HR teams have tried all sorts of things to up retention. Unfortunately for them, they are stuck in a vicious cycle.

Since analysts are in and out in two years, and likely only “all there” for 1.5 years (3 months ramping and 3 months of “senioritis”), senior group members have very little incentive to form long-lasting relationships/mentorships (in my last few weeks at the firm, one of the EDs with whom I worked most closely called me James…). Since they don’t typically take the time to develop long-lasting relationships/mentorships, nobody thinks twice about leaving after 2 years – and so the cycle continues.

Lesson #3: love what your boss is doing

When I joined Morgan Stanley, I could see myself as a Managing Director. That lasted about 3 months. There’s nothing wrong with that career path, but I realized quickly that it wasn’t for me. The best thing Banking did for me was put me across the table from CEOs at companies like TheLadders and Rosetta Stone. It soon became clear to me that the jobs of these CEOs was to create value where there was none, and that my job was to help move that value around. This is a worthy calling, but not one that I was particularly fond of.

When I lost interest in my boss’s job, and his boss’s job, and all the way on up to John Mack, I quickly lost interest in my job and started treating it as a means to an end – “I just have to get through my analyst years and then I can do whatever I want.” This attitude it toxic when you’re at the same time asked to give up your nights and weekends.

Lesson #4: “the only financial security you need is the confidence that you are learning more where you are than you could anywhere else.”

This lesson is in quotes because I have no place giving it. It’s certainly not true for all people in all professions, and I don’t even know if it’s true for me. I hope that I’m lucky enough for this to be true.

When I began evaluating opportunities post-banking, I sat down with a number of internet VCs and entrepreneurs and asked them what I should do over the next 5 years to get ready to be an internet entrepreneur. My plan was: go work for a growth capital firm to get exposure to lots of different early stage internet companies, make a ton of money, then in 5 years launch my own company with all the money I had saved.

I met with about 8 people. Every single person, VC and entrepreneur alike, said the exact same thing: “if you want to learn how to run an internet company, go work at an internet company.”

The first 7 times I heard this advice, I shrugged it off. It wasn’t until one VC continued to push me, and followed up with lesson #4, that the idea finally clicked. One year out of college, and I was already beginning to feel the weight of those golden handcuffs closing around my wrists. With lesson #4 I was able to break free of their grip, and haven’t once second-guessed the decision.

For the internet entrepreneur the math goes like this:

20 years working in Finance: $20MM

Probability of being successful: 80%

= $16MM

vs.

20 years working for a startup and changing the world: Priceless

Probability of being successful: 1%

= What’s 1% of priceless?

I wouldn’t exchange my experience in banking for anything. I learned a lot and met a lot of fascinating people. Most importantly, it led me to my current job, which is probably the one thing for which I would exchange banking.

When rising juniors and seniors ask me whether they should join a startup or go work for a bank, I tell them that they should go where they are going to learn more than they would anywhere else. The answer isn’t very helpful, but then again neither is the question, which brings me to lesson #5.

Lesson #5: There is no track to being a successful internet entrepreneur – nothing can possibly “prepare” you for creating something where there was nothing before.