S1 E8 | How to Pursue What You Want (Not What You “Should”) with Jeff Simnick (Berkeley Haas)

Jeff Simnick

In this conversation, Jeff Simnick (Haas '20) shares his journey from healthcare investment banking in Chicago to pursuing the joint MBA/MPH program at Berkeley Haas School of Business. He discusses his transition from traditional healthcare to digital health product management, emphasizing the importance of authenticity in business school applications and pursuing what you want rather than what you think you should do.

Jeff provides detailed insights into his application process, including his memorable six-word story essay about eating Vaseline during a marathon and his decision to take the GMAT three times to achieve a 730 score. He highlights the value of Berkeley Haas's unique culture, extensive internship opportunities through the dual degree program, and the career coaching resources that helped him navigate his transition into tech. The conversation concludes with his philosophy about following your genuine interests rather than perceived obligations, which he learned during business school.

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  • [00:00:00] - Introduction to Jeff Simnick
  • [00:01:10] - Background and Chicago Upbringing
  • [00:04:10] - Discovering Healthcare Interest at UChicago
  • [00:06:40] - Career Move to Kaiser Permanente
  • [00:08:10] - Why Business School Felt Inevitable
  • [00:10:40] - Tech Friends' MBA Skepticism
  • [00:16:00] - Application Process and Resources
  • [00:20:10] - Berkeley Haas Culture and Fit
  • [00:22:40] - The Six Word Story Essay
  • [00:30:00] - Authenticity in Applications
  • [00:34:10] - MBA/MPH Program Benefits
  • [00:42:00] - Rapid Fire Questions
  • [00:51:00] - Philosophy of Following Your Wants

Background and Chicago Upbringing

My life story is that I grew up in the northwest suburbs of Chicago in a classic suburbia town called Lake Zurich. To your point, I was nerdy, sad, and lonely most of my childhood. I had a normal-ish childhood and was always super academically driven. I just worked hard in school and was always also drawn to economics and business and the financial world, which is ultimately why I decided to go to the University of Chicago in undergrad instead of Northwestern, which were my final two choices, because the University of Chicago had such a stellar economics reputation and I was pretty certain that that was what I wanted to do.

So I left the suburbs and moved into the city, which is not very geographically far but is quite culturally different, especially Chicago. While there I met lovely people like you, studied economics major, statistics minor, studied abroad in Vienna, lots of classic college shenanigans. And the biggest thing while there is that I discovered an interest in the healthcare industry.

Discovering Healthcare Interest at UChicago

Primarily through the clubs, like the undergraduate investment banking group The Blue Chips, if you remember that organization, and they rejected me. Well, I got into the better one, I got into EER Consulting, so that was great. And then between that and also a community-oriented, volunteer, mission-driven student group that I was also involved with called the Community Service Leadership Training Corps, that spent a quarter studying healthcare systems locally, nationally, and globally. I just got a lot of exposure and got interested in it, which brought me to a career in healthcare investment banking afterwards at a boutique called Juniper Advisory. They focused on hospital and health system mergers and acquisitions, so it was a really interesting role given how specialized the firm was. They focused a lot on rural standalone hospitals across the country that can no longer stand alone. As you may know, rural hospitals are struggling in a big way and therefore need to consolidate. So lots of going to small towns in Wisconsin, Iowa, Kansas, and helping those hospitals find partners to stay alive, which, in those communities, the hospital is often the largest economic driving force. So super interesting work.

Investment banking was not what I wanted to do forever, and then having spent 24-ish years at that point in and around Chicago, minus the study abroad, I wanted to move. And then, being a healthcare geek, I had always heard about Kaiser Permanente out in primarily California, but also Georgia, the Mid-Atlantic states, Hawaii, and some other spots, because they are a super unique healthcare model that people don't really see in the United States very often, and also very successful at it, and received lots of praise inside and outside the industry. So I wanted to go work for them. I left the banking job, left Chicago, moved to Oakland, California, to join.

Career Move to Kaiser Permanente

I joined their corporate development and strategy team, where their headquarters are based out of, and did kind of similar in-house investment banking and consulting stuff for another two, two and a half years, and really enjoyed being at a mission-driven company.

There were a few years there where you were riding my coattails, between that and business school, and then at that point I was going to go to business school.

Why Business School Felt Inevitable

As somebody who had less guiding resources in the business world, who didn't have family or very many friends that had gone through business school, it always seemed like the way to get the business stamp of approval. Especially in those early years after undergrad, I wasn't feeling incredibly confident in my skills or career ability to succeed in a corporate environment. There were many long conversations about just workplace early career anxiety, and all that led me to picture business school as this way to get all of the confidence and skills and knowledge to succeed.

So there were those components, and then I would also combine it with the fact that I did want to move away from quote unquote traditional healthcare into health tech and digital health. I wanted to make that transition, and likewise, even more so than not having great guideposts for business, I had even fewer guideposts for tech and what that looks like. So I knew I would need some help doing that. A combination of those, and then I would always hear great things. The business school sales pitch is pretty strong, and so I enjoyed it.

As a side note, on Friday I went to this Y Combinator event. They had their first health tech and bio summit. I just went because I was interested in the topic and wanted to stay fresh on everything and meet some interesting people. Halfway through I'm like, this is like a business school recruiting event. You're surrounded by young people full of big ideas and energy, and they're all selling how great the program is and the resources they have. It was kind of uncanny valley in how it shared a lot of underlying aspects of business school, but also a different take on it.

Did seeing tech friends succeed without an MBA make you doubt your decision?

I never felt doubt about its value. I saw their point, like it's not a must-have, it's a nice to have, and I do think that's true. You can still succeed without it, but to my earlier point of just having fewer guideposts or knowledge, I needed to get some skills, and my confidence is sourced from my education and my knowledge base.

There definitely is the group of people who found success in tech right out of undergrad and therefore questioned the value of business schools. But at the same time, it's hard to deny the stats and the facts when you look at where business school populations go and how successful they are. I knew that even if I was average, I'm going to be fine. So I had a ton of faith in the system, and from talking to Berkeley and all the interesting people, I knew I was getting access to something amazing.

In terms of the receptivity in the market and whether that's changing today, I can only speak from my perspective and vantage point, but I still think MBAs are extremely highly valued. There's an emphasis on them in recruitment drives I've been a part of, and they always bring a superior interview performance. Within the workplace they're more effective and vied a bit more highly. I don't know about the wider market, but I definitely think MBAs have an advantage against other people in the job hunt. It's not like there's a filtering criteria in tech where you need to have an MBA to be brought in, but it is a help. It's like a power-up, a boost.

A final thing I'll add is one thing I realized in business school. It's partially true with tech but especially with healthcare. The University of California Berkeley Haas has a very close relationship with the University of California San Francisco, and UCSF is one of the top medical programs in the country. They train all these brilliant researchers and physicians developing really cutting-edge medical technology. But one of the reasons they have such a close relationship is because they have these brilliant medical and health tech people launching crazy new breakthroughs, but they have no understanding and frankly no interest in the business side of things. They need Berkeley Haas as a pool of MBAs to come and pair up with their brilliant scientists.

That dynamic is actually real. There is this codependency where, and I bring that up because I do think that's replicated to some extent with tech. If you have a technical founder, they don't know or don't want to do the business stuff. There's a real need for it. Even the most talented people and companies in the world need MBAs, because you can be a Nobel Prize-winning scientist, but that doesn't mean you know how to run a company.

What resources did you use during the application process?

For the most part, a lot of self-research and a lot of attending the informational sessions and just meeting with people and talking. That's another big component: you have to put yourself into those rooms and you'll meet people and make connections. Even if you're the worst social person in the world, you learn by osmosis and monkey see monkey do, and you just hear how everything works. I didn't end up using a professional application coach, which I do think I regret in retrospect.

I started going to those events, and I knew I wanted to do healthcare and health tech, so I filtered all the business schools against that spectrum and then focused on five or six that rose to the top. It was Berkeley, Duke, Wharton, Stanford, and maybe NYU or Cornell that had the most interesting healthcare programs in my mind. I just focused on going to their info sessions. I got Manhattan Prep books.

It was all self-study, self-networking. I had friends and previous managers review essays, and I got letters of rec from previous managers. So that was really it.

I took the GMAT three times. My first one was maybe a 680, and then a 720, and then a 730, at which point I stopped.

So in your mind 720 wasn't high enough?

I just wanted to be as competitive as possible. One of the things I heard is that MBA programs need a signal for the average GMAT scores of other people, and so if you have a higher GMAT it'll help them bring up their average GMAT. That made a lot of sense to me, and I just didn't want to be excluded because I would be bringing down their average. Also, maybe just a lack of confidence, but I didn't think I had a very compelling career to that point and I was pretty young. I was three or four years out of undergrad. I just really wanted to have the best score possible.

I felt more like, when I got to 730, it was such a small increase. From 690 to 720, that's a pretty big jump, and I wondered if I could do another big jump. When I did a smaller jump, I thought, this kind of looks like I'm topping out here, so it's not worth it to go through the pain of it once more time.

You're right, I'm a perfectionist, I guess, but I want the best.

Berkeley Haas Culture and Fit

One of the things that drew me to Haas was I got a similar, much more happy in California vibe, but a similar energy to the University of Chicago in terms of culture and spirit and kind of unabashed dorkiness, or like you're proud of it. And a bit of countercultural, I guess, where Chicago is like not like the other top schools, and Haas is kind of like not the other business schools. I don't know how popular of a saying this is, but it did always stick with me. A professor once used: Berkeley Haas is where the suits think you're hippies and the hippies think you're suits.

I bring that up because in the application process, Haas is known for heavily relying on their essays and their interviews more than scores, and having fun and wacky essay questions, which is also super true of the University of Chicago. They're infamous for their weird essay questions. Berkeley Haas, at the time - I think they've changed it now - but it was tell us your six-word story, an allusion to, I think an apocryphal Ernest Hemingway story where it's like baby shoes for sale, never worn. And the prompt was to lead with the six-word story and then expand on it in two or three paragraphs after that.

That was another big thing that got me off guard, is how short business school essays are. You just have to get to the point. And then in terms of writing it, I just jotted down ideas. The biggest thing for me in any writing process, and what's true of business school, was doing the word vomit and getting it all out and then refining it, refining it, refining it, maybe throwing up one more, two more times, different words. The editing is what matters, and you just have to get something on paper that you can then start playing with and moving words around and stuff. So I definitely did first drafts for all my essays.

The Six Word Story Essay

My six word story was: ran 22 miles and ate Vaseline. I like the six word story because I just reflect on who am I and what values do I want to convey to the school of what they're getting. Grit, perseverance, humor, humility. I was also just trying what possible stories could I do that would be of interest. I figured that was a pretty good hook because part of the prompt's question is can you draw in people's attention.

I wrote about this terrible, hilarious experience I had running my first marathon. Jules got me into running; she is the one that convinced me to start doing marathons. My first marathon, the Chicago marathon, I was on Mile 22 and just raced and disgusting and in pain and struggling. I saw people on the sidelines handing out goop, when goop is this gel that's a nutrient-rich energy gel with electrolytes and sugar and all the things you need to stay alive. I'm like, oh thank God, goop. So I ran over and I took a big scoop of goop on my hand and put it in my mouth, and the person handing out the goop just looked horrified and then started laughing hilariously. As I took two steps, my mouth just got coated in waxy Vaseline and I couldn't breathe and I was choking on Vaseline and I had to spit it out and clear my mouth. I looked back and him and all his friends were laughing at me because they were handing out Vaseline for people. The reason I thought people were eating it is they were putting it on their lips, so I thought people were taking it and eating it, but they were just taking it and putting it on their lips. I thought it was food and it wasn't food.

That's the story I wrote about because I feel like I communicated those values. One of my final lines is, this is what you're going to be getting: you're going to get somebody who runs marathons for fun, still has a good laugh about it, and then just finishes the last four miles. That's who I'll be. I'll probably mess up at Mile 22 and then finish the race at Mile 26, and you can count on me to do that.

It was short and concise. It also speaks a bit to, I didn't do anything crazy in my career at that point. I guess investment banking at a boutique and then working at a major healthcare system, but I wasn't setting up solar power energy in the developing world or Forbes 30 under 30. I think you can still craft a really compelling story with relatively mundane accomplishments, as long as it's true to yourself.

Was that the first story you thought of, or did you actually have multiple six-word stories?

I think I had a few other ideas for a six-word story. I maybe wrote one of them, I'd have to look back into my draft. I did the initial getting thoughts down for a couple different stories and then realized that one was the best. Some of the other ones talked about more impressive things than running a marathon, at least in my mind from a career perspective, but I did settle on that one because that one felt the most true and strong, even if it wasn't the biggest thing. All the other stories were bullet points on my resume, so it wasn't really adding anything new because I already put the coolest things I did on my resume. I wanted to round out those bullet points with character, and they didn't need to hear about XYZ merger that I helped with.

That reminds me, when Haas does it, they have students, current students, call to tell you you got admitted, the ones that are helping out the admissions team. They said, you know, you got admitted, and they're like, we loved your essay, it was so funny it made us all laugh, we were passing it around the office to give everyone a laugh. That's the kind of essay you want to write, the essay where people want to pass it around and like, oh my God, look at this.

What was the best advice you got during your application process?

It was something along the lines of don't present yourself necessarily as the best, present yourself as you actually see yourself, and don't try to overinflate things. To be authentic is the biggest thing. By that I mean it's okay if you don't really know what you want to do. A lot of it isn't about letting them know you're the best or that you know exactly what you want to do, but that you understand how it works. Part of the application is that you don't necessarily need to be the best and you don't necessarily need to know exactly what you're doing or say you're going to become the next business tycoon. It's more about that you have ideas, you're smart and driven, and you want to explore those ideas, and business school provides XYZ resources in terms of networks and educations and contacts and programs that you can take advantage of.

It's how will you take your ideas and the resources the school has and spend your time wisely to refine whatever thesis and theories you have and take one, two, three steps ahead in your career that you otherwise would not be able to. It's really more about how you need or want business school as a series of stepping stones to get to where you want to go than it is trying to convince them that you are going to be the next biggest thing.

What are the benefits of the MBA/MPH program?

It was worth it. I don't think I could have moved from healthcare Corp Dev to digital health product management without it. There was so much I didn't know, and it's such a different skill set and world. So a few caveats. One, I was actually in this awesome program that Berkeley offers, which is a dual MBA/Masters in Public Health, where you're embedded fully in the full-time MBA class but stay an extra semester in order to also get a Masters in Public Health. That was really cool, because basically we had a cohort of 25 people within the program who were also "duals," as we call ourselves, focused on the MBA/MPH. It was nice to have this built-in squad who are all focused in the same sphere as you and get along. Berkeley Haas sometimes I feel like is missed as being really, really great for healthcare. This program is one of those reasons. It's extremely popular and just turns out amazing opportunities for people.

As part of that, I had two and a half years, which gave me a second summer internship, which was wonderful. To my earlier point about trying different things and exploring your thesis, it very much helped me in internship hunting to focus on one thing one summer and a second thing the second summer to compare and contrast, and then continue along that line. I would say the biggest and most helpful thing for me was being exposed to and being able to learn from so many different experiences in such a short amount of time. Because I had the two summer internships, I did a fall school year internship, and then through coursework I worked directly with three different companies on semester-long live projects. So within two and a half years, I was embedded within six to eight different organizations, and that ability to see how product works across different organizations is amazing. You just learn what's the same, what's different, what works, what doesn't work, how can you be effective, and you start to realize the underlying patterns across work and business styles when you run through all these different organizations.

A similar thing happens in all other aspects of business school. I probably talked to 100 product managers over my time there, just smart, connected people who are successful, and was able to hear what they're saying, hear what their best practices are, compare, contrast, adjust it, and then formulate my own opinion on it. So that was just wonderful. The other component is having people to process all this information with and also to support you, because it's scary. When you're surrounded by a couple hundred people who all took the leap of faith with you, it's very reassuring, and you all help each other get through the uncertainty of it all, because it is kind of scary to give everything up and plunge into the unknown. So you're surrounded by people who can help process it with you, both your classmates as well as professors at Haas. They have full-time career coaches who are there for you and are always there to talk about your career, and you actually get them forever after graduating, which is another great benefit.

One in particular, Natalie, whose praises I will always sing, super helped me in moments of doubt. There were a few times, in particular my first year internship. The first offer I got, I was applying to healthcare M&A, consulting, and banking internships as a safety in case I couldn't get a product role, because I was too scared. The first offer I got was from Ernst & Young and their healthcare M&A team, basically doing exactly what I was doing before business school, and Natalie was there to push me to say no and to keep going and to get through to the end. So just having those people to drag you and be confident on your behalf when you aren't confident, and when you're feeling the tug towards safety again, is huge. So I think it's mostly the vast amount of options that you have and a support team to help process it all, and all of that just really helped me get to where I am.

Oh yeah, without a doubt. I'm very happy that I moved into product in tech. I do think showing up and doing things even if you don't necessarily think they're worth it, like just going to cover letter writing workshops or "tell me about yourself" workshops, all of these things that might feel like 101 or business for dummies, it helps to practice. Some people think they don't need it, but you can always use more practice. One of the things too is people go and then don't give it a sincere effort, and that's kind of a waste of time. If you're not actually going to try your best and improve yourself, which is hard because you're in a room full of strangers and they're trying to be smarter than they've ever been before, and when everyone else might not be on the same level as you, then you feel weird. So showing up and just giving it a real effort is huge. There were so many times I'd walk into a room with the career coach for the first time and I'm like, I have no idea what to expect, I don't know what the rules are for this environment that I'm entering, but I just kept an open mind and figured I could figure it out. It kind of becomes fun at some point.

Rapid Fire Questions

Was there an interview question that took you by surprise?

I don't think so. I can't really remember my interviews. I think I repressed them. Nothing comes to mind, so I doubt it.

What stereotype about Haas do you think is true?

It's very queer. I think they have the highest percentage of queer students, which is awesome. And they are just a bit more laid-back, California relaxed, and definitely focus on more social impact industries than others.

Anything you would do differently on your application if you had a do-over?

I would get a coach. At the time I thought an application coach would put me into a clone of other people and also confuse my story, or take away from the authenticity of it. But actually, Jules, after seeing you go through the process, I realized it's the opposite, and coaches do just help you tell your story better. Well, if they're a good coach, of course. They help you find your true self and the true story that you want to tell, and tell it in the best way possible, not try to fit you into this mold of what an application should be. I definitely see the value, in retrospect, that I could have used somebody to help tell my true story better rather than turn me into a cookie cutter.

What do you say your biggest weakness is in an interview, and what is it actually?

Off the top of my head, and I don't know if this is cheating, but I do find it to be true. Some of the best advice I got in business school was that our strengths and weaknesses are usually the same thing. The weaknesses are just when you use your strength too much or too little, and I find that to be very true for myself. Take for example, I have a very co-creative, friendly approach to doing business and work, but if I do that too much, it comes across as uncaring, or just too laid-back. So that's one thing I struggle with, or not having an executive presence is another, where if I'm too approachable, it leads to my weaknesses. And similarly, like you mentioned, my perfectionism. If I'm too much of a perfectionist, it is crippling analysis paralysis and isn't helpful. So I do find that to be the truest take on weaknesses and strengths: they're the same side of the coin, just using them inappropriately.

In terms of what I actually say in an interview, I could give a real one. Here's one, and I hate this advice, but it's feedback I got at least two or three times in my career, so I'm like, either this is a trend or people just don't know what they're talking about. Early in my career, managers would tell me my work or analysis was missing the "so what." They'd say, oh yeah, this is a great deck, but it's missing the "so what." By that I think they mean the key takeaway, or the impactful insight. So I would say I'm really great at breaking down problems, telling you what's going on, and laying out reality for you, but it seems like I will often miss that innovative, original thought, which part of me wonders if it's just a BS thing people tell other people when they themselves don't know what's going on. But I do bring it up, because people say it, and so I do contribute that. I think that's one I've used before.

Another weakness, and this one I do use and is real, is that I feel like I am not a quick thinker. I am a slow, methodical thinker who does a lot, and I will often think of my best answer right after we move on from it.

If you had to pick a new mascot for your school, what would it be to fully represent Berkeley Haas?

I feel like it would be the capybara. I don't know if y'all know what capybaras are. They're adorable, they're so cute, the largest rodent in the world. One, they're a rodent. Two, they are cute. And three, they're internet famous for being just incredibly chill and self-confident with everyone. There's all these pictures of capybaras just hanging out with any animal. The capybara will just have birds and monkeys and things crawling all over it, and the capybaras are sitting there like stone-faced, like, yeah, this is cool. And then even a capybara sitting with a bunch of crocodiles, just chilling. Capybaras just get along with everyone, super chill, self-confident, just do their own thing, and are cute. I think I went to it because it's kind of bear-like, brown, taking from the original but chilling it out a little bit. It's probably not going to attack you.

Philosophy of Following Your Wants

The best advice I got in business school was advice that didn't sit with me right at first, but it was again from that career coach, who I think the world of. It's: do what you want to do, not what you think you should do. For me, for somebody who spent most of their life doing what they think they should do, that was very eye-opening for a few reasons, but primarily, when people think about doing what they want to do, at least for me, I'm like, that's indulgent in a bad path and will lead you down roads to Hedonism and gluttony, or just being a bad person if you do what you want to do. You should do what you should do because that's the righteous path. But inherent in that is the assumption that you are a morally bad person and that the things you want are bad.

I think people need to realize that what I want is actually all great things. I'm a good person and I want good things, and they're wonderful, and I should feel no shame in pursuing what I want. Subsequently, when you pursue what you want, instead of doing things that you are really bored or uninterested in, you'll follow these really beautiful, magical careers of mutual co-creation with people. You follow what you want to do, it energizes you in a much more powerful way, and odds are good that the things you want are also good for the world and good for society.