My Career has Been a Process of Trial & Error – Part 4

Click here to read part three of “My Career has Been a Process of Trail and Error”


After business school, I got to work on two development projects — a beautiful 3,000 acre resort project in Napa Valley and a sleek 42-story condominium building on the Dallas skyline. Simultaneously, I was working as the first employee of a startup that my bosses were partners in (one of the benefits of working for a small entrepreneurial firm). Five years in, after the Dallas project finished, and the startup stagnated for a variety of reasons, all of the sudden I found myself in a seemingly perfect situation — I was making good money without much responsibility. I quickly became bored to death. I had no real purpose and I was no longer learning. I realized that being challenged was just as important as making money. I felt the need to take a risk and either start a business or figure out a way to buy one. Going out on my own would expose my weaknesses, but would also give me the opportunity to become a stronger professional. Regardless, just thinking about it made me feel inspired, nervous, and more alive, which I thought was reason enough.

My sister runs a small physical therapy company that her and I contemplated buying on several occasions. We met with the owner a few times, but ultimately decided not to move forward. I had developed a good rapport with him though, and a couple of months later he suggested I reach out to his son, celebrity chef and entrepreneur, Duff Goldman. He was interested in taking on a partner to help manage his businesses. I jumped on a plane to LA for a marathon weekend where he gave me the overview of all his various interests, including TV, appearances, books, license deals, bakeries, and other ventures. We had a common vision for a partnership, felt like we could work well together, and were able to make an agreement fairly quickly. That was two and a half years ago, and so far it has been the best career experience of my life. It checks all my boxes: I’m challenged, I have upside, I’m learning, I have autonomy. I work with an interesting, smart, diverse array of people. I’ve gotten to shape the company and help improve it in tangible ways.

Even though, I am lucky enough to work in a fun industry, it is still work. I hear a lot of people say their dream is to open their own bakery or cake shop. Sometimes I get the impression that people think my job entails sitting around eating and ogling at beautiful cakes. While I do some of that, the other 99% of my time is spent responding to emails and phone calls, sitting in meetings, making to-do lists and spreadsheets; managing investors, employees, lawyers, consultants, and vendors; and dealing with HR problems, legal contracts, insurance, accounting, budgets, and compliance. Most of what I do isn’t very glamorous; in fact, it can be granular, complicated and sometimes boring. Progress doesn’t come easily, but when it does it’s extremely gratifying. I love the process of collaborating with my coworkers to build a better company. Getting on a career path that I’m excited about took a long time, and that’s just the first step. Now, of course, I feel the urgency to make progress.

The most important things I’ve learned about figuring out what to do for a living is that experimentation is key and to put any job in perspective, you need something to compare it to. I would add that beyond thinking about specific functions or roles, it’s worth considering what other variables might be more relevant, like company size, culture, compensation (amount and type), flexibility, stakes (are lives at risk?), status, degree of influence, breadth of responsibility (9 to 5 or 24/7), etc. The list is different for everyone, but the only way to figure out which variables matter most is by exposing yourself to different ones. The best thing I ever did was to get real world exposure to a number of different companies and work environments early on. Not only did it help me figure out what career characteristics would be more likely to make me happy, but it also helped put different positions in perspective. The only way to develop that perspective is through a process of trial and error.

My Career has Been a Process of Trial & Error – Part 3

Click here to read part two of “My Career has Been a Process of Trail and Error”


I learned a lot in that job, including the fact that consulting wasn’t what I wanted to do with my life and that, instead, I wanted to be in a principal role. I wanted to be in position to drive the process, not just advise on it. I wanted to make decisions and live with the results. I switched to a small real estate private equity fund. I was learning, the atmosphere was casual, and the people were smart, but down to earth. There was little to no bureaucracy. I felt at home in a company culture for the first time in my career. Among other things, I learned the importance of fit.

Although it was a great experience, I realized that working directly for the two fund managers, there wasn’t much potential for growth so a couple of years in I applied to business school. I wasn’t sure if I wanted to go, but I also didn’t know what I wanted to do long term, so I thought having an MBA would create options. My world broadened. I met great people. I was reevaluating my career path yet again — career panels, interviews, conversations with classmates, around and around. The truth is, most people in business school don’t know what they want to do for a living, which is exactly why they go to business school to begin with.

I had a great professor in college that emphasized the importance of ownership. That stuck with me. I liked the idea of running a business. Of having more control over my work life, getting to set the priorities, and living with the consequences of my decisions. Living with results has always been more palatable than living with the subjective assessments of other people. I also liked the idea of building something, something that could continue to exist (and I could make money on) even after I was no longer involved with it (the opposite of billing for your time). I also knew I wasn’t an “expert personality”, I would never be able to compete with the quants and engineers. I am much more interested in how the parts fit together, seeing the big picture, and thinking about where to go next and how to get there.

After looking into several different paths, I once again concluded I wanted to be an entrepreneur, but didn’t have any great ideas. So, once again, I decided that the real estate industry would offer the best opportunity for me to continue moving in an entrepreneurial direction as an employee.

My Career has Been a Process of Trial & Error – Part 2

Click here to read part one of “My Career has Been a Process of Trail and Error”


I chose my major through a process of elimination — I knew I didn’t have the science chops to be a doctor. I was interested in psychology, but when I learned there was a required lab that was out of the question. My father complained about aspects of the legal profession, including the hourly billing model. I’ve always preferred subjects that are clearly applicable to the real world, so I naturally gravitated towards business.

I was fortunate to have a several internships in college, the last of which, at Arthur Andersen, landed me a full-time offer in business consulting. My first day of work was September 10, 2001. After 9/11, the economy took a major hit, and the end of that year brought accounting scandals of epic proportions. Arthur Andersen found itself at the center of the imbroglio, and after 89 years in business, the entire company imploded under the weight of a criminal indictment by the Department of Justice (of which it was later exonerated). KPMG acquired the practice I was part of so my coworkers and I were spared layoffs, but that experience taught me to see risk differently. I learned first hand that the idea that bigger companies are less risky is pure fallacy. While working at those firms, I also realized I didn’t want to be on a 20 year pre-determined path, and found all of the layers of bureaucracy to be uninspiring, to say the least. I realized that ending up in a career I wasn’t inspired by was a different type of risk, to my personal happiness.

I was interested in entrepreneurship, but didn’t have any ideas I deemed worthy of pursuing. I looked into different obvious possibilities, like becoming a franchisee, and other less obvious ones that came about, like importing marble from India. I ended up accepting an offer to work at a smaller consulting firm specializing in market analysis for real estate development projects. I was drawn to real estate because it is a highly fragmented industry, which to me meant opportunities for entrepreneurs. It is also tangible, something I desperately wanted after my immersion in forensic healthcare reimbursement audits. The fact that I could actually help create something that people would use was extremely appealing. I also saw it as a good opportunity to experience working at a smaller firm. Maybe consulting wasn’t the problem, maybe firm size was the variable I needed to test.