Jeff Wilser, BHP ’98, isn’t a typical BHP grad. He may have started on the path of a typical business grad, but that path veered into something quite different. Jeff is a writer, and has just published his third book. Most of his writing is on the topic of guys’ perspectives on relationships and culture. His website touts that he is, “likely the only person alive to have written for both GQ and The Knot.” He has made a number of TV appearances and frequently contributes to various magazines and newspapers. We sat down with Jeff, who currently lives in New York City, to find out more about his career path and what is on the horizon for him.
You have quite a variety of experience. Take me through your career trajectory.
I started in corporate finance at Intel and I realized early on that it wasn’t what motivated and challenged me. I actually had a spreadsheet with pros and cons of different career options, including being a history professor or a writer. I decided to try one more business before totally switching, so I went to Gap, Inc. in San Francisco as a senior analyst in marketing strategy. I stayed there for about a year and then moved to New York to get my Masters in Fine Arts (MFA), with a concentration in Fiction.
I didn’t really do any writing prior to that. The first short story I wrote was for my MFA application. There was only one tiny problem with Fiction writing: I wasn’t very creative. But I found that I really enjoyed non-fiction. My first paid job was writing about bars. It paid $12 a review. I lost money every review because my tab was more than my pay. It snowballed into nightlife writing. I got more editorial experience and was doing a lot of freelancing for other publications. I was mainly writing about pop culture, relationships and men’s interests. I was approach by a publishing company about writing a humor book about “man rules.” Also around that time, I was approached about starting a website that would be a resource for men getting married called ThePlunge.com. The publisher liked my voice and wanted me to write it. Then I started writing about that subject for various magazines. I just released my third book and am also doing some marketing strategy and analysis work for a company on the side.
At this point in your life, what do you enjoy doing the most?
Writing-wise, I tend to gravitate towards guys’ thoughts on relationships, but have enjoyed going outside of that this year, like talking about the world’s next super powers, or military history, or how California is exporting more wine to China. Writing gives you constant intellectual nourishment. I am enjoying more exploration of niche topics. I wrote an article about ancient monks this year.
You have made some bold career changes. Did you view those as risks? How did you overcome the fear of learning and doing something new?
I definitely viewed them as risks and it was actually part of the appeal. I am a bit of a risk seeker. I joined the Marine Corps when I was at UT. I liked the idea of testing myself. This was another way of testing myself. Sticking with the chosen path of finance would have been the safe and optimized path as far as money, but I knew it didn’t really jive in my gut with what I wanted to do. I knew at that gut level that the writing path squared with my deeper motivations, so I was able to ignore the risk and move forward. My business background also provided a safety net. I knew I would always be able to find another job in finance or marketing if I wanted to.
Tell me about the books you have written.
The first book I was approached about writing was The Maxims of Manhood: 100 Rules Every Real Man Must Live By. I don’t claim to be an expert. I just try to be entertaining. After I published that book, I was framed as a “man expert.” My second book was The Man Cave. Clearly that’s my Pulitizer-bait. Andrea Syrtash and I wrote a new book about how dating rules are all dumb, titled It’s Okay to Sleep with Him on the First Date: And Every Other Rule of Dating, Debunked.
I wasn’t prepared for people I knew actually reading my books. When my first book came out, people I hadn’t talked to in years were contacting me about it. That book was very personal. I included more than I would have if I had thought through who would be reading it. It was both cool and horrifying that people I knew – and my parents—were reading it and asking me about parts of it. It is very hard to write about relationships while you are in a relationship and I have made mistakes in the past, revealing maybe more than I should. I don’t do that anymore, but it is still awkward to write about my private life in detail. It is a major career hazard.
As someone who has never been married, what prompted you to start ThePlunge.com, a website for grooms, and why do you think people connect with your advice?
It was important to us to have a mission of brutal candor and be really honest. We felt like the other websites out there for grooms weren’t true to how guys think. The publisher actually really liked the fact that I wasn’t married. I wasn’t biased by my own experience and I wasn’t accountable to a wife and could be really honest. I do a lot of research and do a lot of interviews to try to instill grooms’ perspectives and voices into my articles.
I think people connect with the irreverence. A spoon full of sarcasm helps the wedding planning go down. The tone is different. I think guys can really relate to my voice.
How do you think BHP prepared you for all you have done?
It pushed me to ask questions, challenge myself, and do new things. I love that I have BHP as my background. My favorite class was advanced stats with Dr. Jay Koehler. He talked about how so much of the world is explained by statistics. It has influenced my writing. That business background—I hope—gives my writing more texture. It has been useful to have a business foundation. Having done business at the beginning of my career, it gave me more confidence to do something very different and really do what I wanted to do.
What is the most valuable thing you have learned in your career so far?
Say yes. It was especially important at the beginning of my writing career. I had a lot of wacky writing offers that didn’t make sense at first. I tended to say yes and that has opened surprising doors. Now I can look back at my career and see a through-line. The hub is guy’s perspectives on relationships and culture. While I was doing it though, it felt really random. I was open to rolling the dice on new projects, and there were a lot of positive ripple effects.
What is next for you?
I am working on a new book of personal essays about the awkwardness of dating as an adult, defined as being of a certain age when most of your friends are married. There is pressure when the rest of your friends are all married and have children. Also, more freelance writing for magazines.
Any words of wisdom for current BHP students?
I don’t know how wise this is, but I don’t think there is a chosen path that anyone has to follow. No matter what you are studying now or what your interests are now, that might change. Don’t be afraid to explore other interests. Even though it might not be the logical next step, it might pay off in the long run.