I was an investment banker for only 1 year before leaving to go to a hedge fund. Most investment banking analysts stay for 2 or 3 years, but my entrepreneurial itch was just too strong. My personality is such that I prefer doing work that is going towards making a possible investment, versus simply maintaining a relationship with a client. I also needed the freedom to work on my own ideas and not merely follow orders. Of course, I knew I would still be taking a lot of direction from the senior analysts and portfolio managers, but at least I could exert influence towards investment ideas.

I started searching for an opportunity after six months at the bank, and it took me another six months to make the transition. It took about 2 months of interviewing to get the hang of it, but most of my time was spent trying to set up the interviews in this very competitive market. I started by reaching out to my network, but I didn’t get very far. I also went to a head hunter, but again I found it very difficult to stand out. After four months of interviewing, I finally got into a rhythm and additional interviews came to me by chance (met someone in a bar, and met someone through a friend). It takes practice to understand what answers work well, to know what jokes get a laugh, and to learn what interviewers want to hear.

Around month 5, I interviewed at a large fund and I was told I was selected to come in because my resume was on the top of the stack of 100 resumes. The portfolio manager showed me the stack and said, “I don’t even know where to start. You are literally here by luck, so impress me.” I knew I had to do something different, and my typical round of stock answers and jokes wasn’t going to cut it, so I decided to take a chance.

Instead of talking about getting shares of stock in the Boston Celtics for my Bar Mitzvah, I said, “I am so obsessed with stocks, if you give me the chance to prove it to you by doing a case study, you will see some of the most creative, out-of-the-box thinking you have ever seen.” Now that is a big promise, but who wouldn’t take me up on that offer? After getting through the personality fit part of the interview, I was offered a chance to prove myself. I was given the case study Men’s Warehouse.

The good news was that I owned a Men’s Warehouse suit, so I already had my wardrobe picked out for my return visit. I spent most of my time going from store to store, interviewing Men’s Warehouse managers, counting traffic, and interviewing friends and family over survey monkey. I learned random interesting facts about the business that anyone would be interested in hearing and intertwined them into my pitch. For example, the average tuxedo is worn 70 times, but the payback is after only 3 wears. 70 wears is flat out gross, and so think twice about asking your friends to get matching vests for your wedding and let them wear their own tux.

The portfolio manager was so impressed that he gave me the job. All of the other candidates simply built a model, read the 10Q and 10K, read the transcripts, and wrote a report that could easily be found on the Internet. By taking a chance and making an incredibly bold statement and then backing it up, I was given my dream job. That type of behavior is exactly what they want to see – bold, confident, hard working, and no bullsh*t. That’s what it takes.