Over the weekend I had the chance to sit down and interview someone who is technically my boss, founder of Wall Street Oasis, Mr. Patrick Curtis. Though, most of you probably know Patrick as the orange bearded monkey that goes by WallStreetOasis.com on the forums (real original).

The overlord of WSO is actually a pretty nice guy, and was kind enough to share his professional path from investment banking to private equity. In part one of this two part series, Patrick details how he broke into investment banking in a post 9/11 world and his time at Wharton MBA.

Enjoy, and make sure to read part two as well

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MF: So that WSO users can get some background on you, let’s start off by talking about your past investment banking experience as an analyst.

Patrick Curtis : I broke into investment banking in 2002 through OCR at Williams College (yes, our mascot is a Purple Cow). It was actually a pretty tough year (kind of like now), since recruiting was right after 9/11 and a lot of banks just cancelled OCR and/or scaled way back on the number of positions they were looking to fill. So I think I was lucky, to say the least. There was no Wall Street Oasis back then and I barely even knew what to expect during interviews.

I think the two most important facts I learned as an analyst was:

1) I do have a breaking point

2) It could always be worse.

Before Rothschild I thought I had an incredibly demanding schedule: 5-7 hours of homework every night, sports in high school followed by more challenging academics and sports at Williams. The reality is that I always had enough free time to get it all done and do well.

I remember a few months into my analyst stint we had a particularly brutal week – I had slept 3-5 hrs each night and had been in the office every waking hour. Then on Friday there was a “fire-drill” at 5pm that included a ton of work that needed to get done by Monday – this was all unexpected. It didn’t hit me until that point how tough the job was – both mentally and physically. It can mess with your head when you never know when you would have time off or when you’d suddenly get staffed on a Friday afternoon ruining any chance of having a day off.

Do not get me wrong, my two years at Rothschild were extremely rewarding (professionally) and I learned an incredible amount. I worked with some great people in the restructuring group, got to close on several live deals, etc. By the end of the first year, however, I realized that no matter how tough or competitive I thought I was, the machine will take every last ounce of will you have if you let it.

I have no regrets, but I knew I couldn’t survive for a third year so I started looking into private equity by year two.

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MF: What about your transition to Private Equity?

Patrick Curtis : I made the move to private equity primarily because it sounded interesting (invest in companies across a variety of industries), the pay sounded great and it would give me a chance to move back to Boston to be closer to more family and friends…plus, I knew I would completely burn out if I stayed a third year in banking.

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MF: What was the most important part of your private equity experience?

Patrick Curtis : As some of you know, my move to Boston and working for Heritage Partners was a short one. I was called into the office for my first review five months into the job, and fired on the spot- I was shocked and confused (a few days before Christmas – happy holidays!).

I was determined to stay in private equity in Boston and over the next three months I had a ton of interviews and had basically secured several jobs…except for one thing: I would not sign the release form and take the $10,000 Heritage offered me. Since I wouldn’t sign (because I didn’t know why I was fired), they would only “confirm that I worked there”…try getting a job in PE with that reference. I lost so many “in the bag” offers that a recruiter I was working with at one point flatly stated, “You’ve been blackballed from the PE industry in Boston.” Not a fun three months.

Long story short, I ended up at Tailwind Capital in NYC (yes, still in PE), thanks to a former co-worker at Rothschild vouching that I was a good analyst – he was a pre-MBA associate there at the time as well.

About a year after I was in NYC I started reading some PE news about Heritage and how some of their biggest investments we going bust – investment professionals went from something like ~20 down to ~5. So I quickly realized that I was just the first out in a long line of firings (bad diligence on my part).

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MF: When did you get the idea for WSO?

Patrick Curtis : I actually got my idea for WSO (initially iBankingOasis.com) when I read a Top 30 Entrepreneurs Under 30 article one night. I thought to myself, what can I start now that may give me some independence in the future. All I really knew was iBanking at the time so with the help of one of my friends from MIT who was a coder, we set up iBO back in 2006 and it grew from there.

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MF: Why leave PE to risk it all on a website?

Patrick Curtis : Why not? We’ll all be dead in 60 years anyways. I plan to enjoy the ride as much as I can.

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MF: So took the idea and left the industry to go to Wharton MBA, how was your experience there?

Patrick Curtis : My experience at Wharton was great – I especially enjoyed all the support my classmates and entrepreneurial programs gave me. They knew my goal was to make WSO into a real business that I could run full time. I got great advice from so many of my classmates that really helped transform the business and I really think that is why we have come so far.

Besides also being a much-needed break from investment banking and private equity, the environment is less about grades and more about true learning. I felt like I could take out whatever I wanted from every class and I really didn’t care about my grades. I still did well, but the beauty of grade non-disclosure and not recruiting is that I had the freedom to really build WSO while going to class.

Part two tomorrow will discuss more about WSO and it's future, so definitely stay tuned