Name: Desmond “Des” Duggan
Hometown: Aspen, CO
Undergrad: Washington University in St. Louis, School of Engineering
Majors: Systems Engineering, Computer Science
Activities: Varsity rowing, Beta Theta Pi fraternity, WUTE (WashU Tech Entrepreneurs Club), Cheap Lunch @ Engineering School
1st Job: R&D Software Engineer >> R&D Associate Manager @ Accenture Labs
2nd Job: Product Manager @ AppDirect
Current Job: Senior Product Manager @ AppDirect
Internships: The Motley Fool, Accenture, Cultivation Capital
Heading to WashU as a freshman, Desmond “Des” Duggan had been exposed to and was captivated by the world of engineering. As a sophomore he was introduced to consulting. In the following years, Des straddled the line between the two paths enjoying both. Because of his philosophy of “The harder you work, the luckier you are,” Des picked up internships and jobs in both arenas and shifted his job search to include geography. He had always imagined he would live in Chicago, but had a desire to live in the Bay Area. Des was ultimately offered positions in both locations. Using mental models and through the realization that if he didn’t figure out how to tell his own story that others would tell it for him, Des landed the perfect first job out of college at Accenture’s R&D Labs. Here, he shares stories of sacrifice, intense dedication and discipline, and the rewards he reaped in return — both in his professional and personal life.
Where were you born and raised?
I was born and raised in Aspen, Colorado. Growing up, all I could really think about was shredding powder, acing my video game campaigns with my friends, and memorizing the phone number to Domino’s Pizza. I was not very athletic and I was pretty shy, but I would say I had a very standard childhood. What I love about growing up and Aspen, in retrospect, is that there is a culture of appreciating nature. For example, The rite of passage at Aspen Middle School is going on a long hiking trip with everyone in your eighth-grade class. During that hiking trip, one goal is to spend 24 hours by yourself in nature. The teacher drops you off somewhere and picks you up the next day.
Did you grow up with brothers and sisters?
No. I am an only child. My parents were divorced when I was pretty young. They live very different lifestyles. My mom was playing golf and skiing, living this more luxurious lifestyle, whereas my dad lives on a ranch with my stepmother. They have very different approaches to life. I think out of that I developed this extreme sense of empathy, because I was trying to understand why my parents were each a certain way. At the same time, I found myself in the middle of a lot of conflict growing up. I consider myself a diplomat, and I take pride in being able to resolve almost any conflict.
As a child, what did you want to be when you grew up?
I didn’t put a lot of thought into it, to be honest. Because I was shy and because I was into video games and electronics, I think I knew that I would end up doing something with science, math or engineering.
What was your first job?
My first job was at the Aspen Public Golf Course as a bag drop, which is the person who accepts the bags from people’s cars, puts them on a cart and cleans and puts away clubs as golfers come back from the course. It was a very humbling job to some extent. I also worked at the coffee shop in town making and serving ice cream.
How did you get to WashU?
When I was applying to college, I probably did what every high school student does these days. I looked at the ratings in every magazine and tried to figure out the best possible school that I could get into. Then, a buddy of mine was visiting WashU while I was visiting Duke. We called each other that weekend and he pitched WashU to me. He told me it was a great school, a beautiful campus with lots to do and that I would really fit in. At the same time, I did the same thing to him with Duke. Long story short, I ended up going to WashU and he ended up going to Duke.
How did you choose engineering?
I was lucky enough to recognize at age 15 that I like technology. Another job I had in high school was working at a computer repair shop. I fixed computers and processed a lot of returns for broken hard drives and did. When I was probably 10 years old, my dad gave me his old Windows 95 desktop computer. I spent an afternoon deconstructing the whole thing, pulling the capacitors off and shocking myself, exploring every part of the computer. I had a natural affinity for it, so when presented with a choice, I just followed my intuition on it.
Systems engineering felt right to me because it was effectively applied math and it wasn’t so restrictive.
What did you major in?
I majored in systems engineering and computer science.
Why did you choose systems engineering and computer science?
After I was accepted to WashU, I got the booklet from the engineering school explaining the different majors. I didn’t really get excited about mechanical engineering or any of the “hard” engineering programs, not difficulty-wise, but hard sciences like mechanical, electrical and hardware. Systems engineering felt right to me because it was effectively applied math and it wasn’t so restrictive. I took on a second major in computer science my sophomore year after I took a couple intro courses.
When you weren’t in class, what else were you doing at WashU?
Early on in college I joined the Crew team. I had never been exposed to rowing growing up, but I went out for the team because I met this cute girl who invited me to go to practice with her. She is now my wife. I stayed on the Crew team for four years and I was president for two years. We practiced at least 20 hours a week and we were traveling quite a bit during the fall and spring semesters. That took a considerable amount of time. Outside of that, I joined a fraternity, Beta Theta Pi. I was a leader in the WashU Tech Entrepreneurs Club during my junior and senior years. I was a part of the engineering council, and I organized this thing called Cheap Lunch at the engineering school every week.
What did you do to goof around?
Aside from the usual adventures that you find yourself doing on the weekends, we loved tripping around St. Louis. After Crew practice on Saturdays — we had been up since 6 a.m. on a Saturday morning, having sacrificed Friday night to go to bed early and get a good night sleep for practice — so after rowing for three hours on Saturday morning we would feel a bit slap happy and find ourselves tripping around the city. We’d spend two or three hours eating brunch, hanging out.
When did you start thinking about life after graduation?
When I got into college I was at a time of my life where I had very intentionally started focusing on my career. There was a time in my younger childhood where I had maybe started falling in with the wrong crowd and I had been influenced by some people, so when I got into college I really focused on changing directions. Even during my freshman year, I was thinking about the future. I had some good influences and good mentors in my life at that point. My freshman year I studied chemistry over the summer and didn’t have an internship. The following year I got a sophomore engineering internship with a company in Washington, D.C., called The Motley Fool. At that point, I really started thinking about what it would look like to have a career in software engineering. At the same time, I was approached by Deloitte pretty early in college to join a mentorship program. Through that I got to meet a bunch of Deloitte managers and managing directors and see what their careers were like. That’s when I got exposed to consulting.
You changed directions; from what to what?
Having grown up in Aspen, there was a time where I had this narrow view of the world. I was content to be with my friends and not think more than a few weeks in advance. My life was good and I didn’t really have to work too hard to enjoy that. That switch happened gradually, but also pretty suddenly at the climax of that time. I started thinking further down the road and asking myself deeper questions, which focused me. What I was going to is a place where there was a lot more certainty and clarity in my life. I found that through relationships with other people and my career.
If you’re not putting yourself out there and you’re not hustling, you’re not going to be exposed to anything interesting.
Did you have a plan for life after WashU?
I didn’t have a plan. I knew opportunities available to me would not present themselves. I knew that I would only have those opportunities if I put myself into a position where they would come up. That goes along with the expression “There’s no such thing as luck, but the harder you work the luckier you are.” If you’re not putting yourself out there and you’re not hustling, you’re not going to be exposed to anything interesting. It’s going to be business as usual.
How did you get the Motley Fool internship?
I was starting to get interested in software engineering. At the same time, I was getting exposed to consulting. From that point on, I really had a hard time deciding which of those two I really felt more called to do and which one I was better at. For a long time I just straddled the line between engineering and consulting. I found myself enjoying the people in both arenas. In the consulting world at WashU, you find different clubs practicing for consulting interviews and mentorship programs. People would dress up and go to events together. It was very business focused.
On the other hand, I was a part of the engineering council, and I organized this thing called Cheap Lunch at the engineering school every week. I loved hanging out with engineers and talking about brainy problems and the things we were working on. That translated directly into my professional life. I worked a software engineering job my sophomore year and a consulting job my junior year. When I graduated, I took a job that was squarely in the middle of those two things.
How did you find out about internship?
I think I just Googled software engineering internships and found my way to The Motley Fool website. I dropped my resume in a bucket and heard back. It’s funny, because that rarely works out. I think I got incredibly lucky. If I was going to give any advice to students who are still in college, that is the absolute worst thing you can do. That’s the path that I took and things worked out.
The Deloitte mentorship program contacted you?
Yeah. They have a pretty strong presence on WashU’s campus. They reached out to a group of systems engineering majors. A few companies in the consulting world were really interested in having more engineers in their applicant pool. The program was a great thing to be involved with, because it really exposed me to what it was like to work in consulting. I got to talk to people who had been out of school for a couple of years who came from WashU. Those relationships were great because I was able to carry on conversations with them from year to year.
What exactly did you do in the mentorship program; was it helpful?
It was just an opportunity to learn more. I think you need a posture in college of just being a continuous learner and having a certain intensity about it. Deloitte would host several events over the course of each semester. They would bring all the students together and all the mentors together to socialize in that setting. I think the mentorship aspect of it was great because you’re talking with someone who very recently was in your shoes. It’s useful to have someone who is going to level with you and tell you what things are actually like. It’s so easy, especially at a place like WashU where everyone is so competitive, to compare yourself to other people and start creating these perceptions of what you think jobs are like when the reality is that it couldn’t be more different from what you imagined.
Did you have any other internships?
I interned with Accenture my junior year. I found that internship through one of the WashU hosted career fairs. I was talking to a number of companies at the same time, but the Accenture internship panned out. Interestingly, my original offer was to work in the Accenture Chicago office, but in my last interview I had made a point to talk about a parking app I was working on at the time with a few grad students. The idea was to put cameras overlooking a parking lot and use some computer vision algorithms to detect if parking spots were available and publish that info in a parking app. This turned out to be a critical juncture for me because the interviewer thought I might be a good fit for Accenture Labs, the R&D outfit of the company out in the Bay Area. I might have had a few options on the table, but I was really excited with this opportunity because it was in Silicon Valley. Having spent the previous two years thinking about technology, San Francisco was clearly a place that was really exciting, and the Bay Area was the epitome of that. That was really exciting to me.
When I started thinking one or two steps out, my path started becoming a little more clear to me.
How did your internships translate into your job search?
I think my biggest takeaway was you have to pursue things that excite you. I enjoyed my internship with The Motley Fool doing software engineering and software development. I learned quite a bit, but it didn’t excite me.
In contrast, I was really excited about what I worked on during my junior internship. I loved the vision for what my organization was doing. The people I was working with were super sharp. That was what really what drove me. At the same time, I think I started being a little more strategic in thinking second and third order. I started thinking about internships as the start of the story that you’re telling in college. I began asking myself where my internship would lead next, and once I get there, what do I do after that? When I start thinking one or two steps out, my path started becoming a little more clear to me. I had stronger resolve for wanting to be in the Bay Area where technology was. I started optimizing for those variables and trying to plan out what my life would look like.
Did you have job search target criteria?
I guess I started realizing that although I was very ambitious, I had other things in my life that I was optimizing for. When I was a senior in college, I was in a very serious relationship with my girlfriend at the time, now my wife. I knew myself and I loved being an athlete. Having spent four years on the rowing team, I was in incredible shape by the time I graduated college. I knew what it looked like to be really financially and professionally successful, because I grew up around people who spent their entire careers in New York or San Francisco and retired in Aspen, Colorado. I was starting to optimize for balance across all these different areas.
Accenture was not my be all, end all, but I knew I would be happy enough and it would get me to the Bay Area, where I could think about what was going to happen next.
Maybe I was optimizing for overall happiness, where happiness is a function of a number of different variables. How healthy are you? How emotionally stable are you? How professionally successful are you? That’s the lens I started looking at my life and my career through.
Accenture was not my be all, end all, but I knew I would be happy enough and it would get me to the Bay Area, where I could think about what was going to happen next. I had the right balance of things in my life at the time.
How did you approach your job search?
Coming out of my junior year internship, Accenture gave me an offer by mid-October and they gave me two or three weeks to accept. At that point I was interviewing with Deloitte and a few other consulting firms. I had an offer from PWC for their Chicago cyber-security group. I was interviewing with Google and a few technology companies in the software world. I had a feeling I was going to get a job offer from Accenture, so I had confidence going into interviews, which was extremely helpful. Building that kind of confidence going into interviews is so challenging because you’re worried about what people think of you and you’ve got to perform.
I was really stuck between software engineering that was pure software development and trying to go be a strategy consultant with Deloitte or McKinsey or Bain.
I was really stuck between software engineering that was pure software development and trying to go be a strategy consultant with Deloitte or McKinsey or Bain. I interviewed across the board in those two different fields to see what it might look like. That was super useful, because I think you learn a lot when you interview. The interview questions that you get asked are actually pretty representative of what that job is going to look like. If you like it, chances are you probably got the job. That was one of the observations I had. Interviewing is a tool to get exposure to what different fields look like.
How did you make a decision and say “yes” to Accenture?
It’s interesting, because I always imagined myself living in Chicago. I definitely struggled to make a decision, especially having offers at both PWC and Accenture. Going into my senior year of college, I was really analytical. I just sat down and started putting this decision through all of the different decision frameworks that I could think of. I looked at the pros and cons of each, a SWOT analysis of each of these things. I started scenario planning. What would it look like for me to go to work for PWC in Chicago? What was that going to give me? What would it look like if I went to the Bay Area? What opportunities would each present?
I really thought about the options using a number of what are called mental models, or different ways to think about a problem. I think the output from that ended up making the decision pretty clear for me, because a dominant variable and my decision-making was wanting to be in the Bay Area. I was really excited by technology and what we could do with software. I was a leader in the WashU Tech Entrepreneurs Club during my junior and senior years, so I was one of the people at WashU who was trying to get a Silicon Valley thought process into the university. That was extremely dominant.
At the end of the day, when I hadn’t firmed up whether or not I like software engineering or consulting more, the Accenture job was right in the middle of those two. The combination of it being in the Bay Area, technology, and a non-committal answer to whether I wanted to be a software engineer or a consultant, Accenture hit the sweet spot for me.
I have a few mental models. One is variable optimization, which is where you list out all of the variables, assign weights to each of those and then put in your input in. You can compare options pretty easily with that model.
Which mental models were most helpful?
I have a few mental models that I use all the time and I love. One is variable optimization, which is where you list out all of the variables, assign weights to each of those and then put in your input in. You can compare options pretty easily with that model. That was basically what I studied in college, systems engineering, like when you’re programming and optimizing four combinations of linear problems.
I also thought regret minimization was really useful. Regret minimization is this concept of minimizing regret in the decisions you make. A good example would be that I had two job offers in hand at the time: PWC in Chicago and Accenture in Silicon Valley. I think I would have regretted not going to the Bay Area, because I was excited about technology and the energy in Silicon Valley is palpable. I had been exposed to that during my internship. I think I would have majorly regretted not going there.
The worst thing I think you can do is during the fall semester of your senior year is spend all of your time studying and then taking 15 minutes for interview prep in interview season.
What interview prep was most helpful for you?
Practicing with other people is really useful. I generally am one of these people who works independently. I had a very hard time practicing or preparing for interviews with other people. I didn’t do it as much as I should have. I think I made things harder on myself by not understanding that earlier. Preparing with other people adds a certain intensity to your practice, especially for consulting interviews where you have to do a role-play with someone super smart and who is five years older than you are. Getting in a room and practicing with somebody who can keep you sharp is super useful. In the software world, I think that matters a little bit less, but it is still useful. There are tons of resources on the internet for practice problems in both software and consulting.
The point of going to college is to educate yourself and to get yourself a job. The worst thing I think you can do is during the fall semester of your senior year is spend all of your time studying and then taking 15 minutes for interview prep in interview season. It’s acceptable during your fall semester of senior year to let your studies take the back seat in terms of time to prepare for interviews. You should be putting in five or 10 hours per week preparing. It’s a big deal. It really is one of the situations where preparation pays off big time.
If you don’t prepare your own story and you don’t know how to speak to your story, then other people will fill it in for you.
Any other interview prep that was extremely helpful?
Yeah, there is. I started thinking about this a lot more recently, but I started doing this in my later years in college too — and that’s thinking about your story and the story that you are trying to tell. It’s one thing to be prepared for these interview questions, because companies are trying to assess whether you have the skills and whether you have the cultural fit with the job that is available, but I think there’s a certain amount of leeway there. If you think about it from the interviewer’s perspective, they’re trying to hire as many rock stars as they can. They want people who are going to totally crush it. When I think about rock stars who I have been exposed to, they’re really good storytellers and they really know how to tell their own story.
Being able to tell your story puts you in a better position when it comes to the interview, because you know where you come from and you know where you’re going. That brings confidence and it uplevels the conversation a little bit. If you don’t prepare your own story and you don’t know how to speak to your story, then other people will fill it in for you. We naturally label people as being x, y, and z. Those are going to be stereotypes and archetypes of you, and you don’t want that. You want to be able to tell your own story and be able to control that part of the conversation.
How do you figure out your story; how do you tell it?
It’s very, very hard, especially at that age. I had a hard time in college doing this because I was so obsessed with what other people thought about me and with meeting the expectations of the people around me. WashU has such a go-getter attitude that it’s hard to disconnect from that for a moment to think introspectively. I read a book called “Mastery” by Robert Greene, where the author talks about how to think about and identify what your calling is and how to dominate in that calling and your profession.
This idea of finding your calling is really the beginning of being able to tell your story. You have to know where you come from and that has a context to where you are today, so you can think about what the next year is going to look like. Practically speaking, I think what that looks like is talking to your parents and friends, and thinking about the things that excited you when you were growing up. Was there a thing that you could spend hours doing without being interrupted? Those are the kinds of things that you’re looking for.
I have a couple examples of that. My dad was taking me around his ranch when I was about eight years old. We were walking across the field and there was a bunch of sage brush on the ground. Sage, if you don’t know, smells so powerful and so good. I suggested we take the sage and make soap bars to sell. My dad thought it was a really good idea. That’s an example of being excited about business in a way, and this idea of creating something and bringing it to other people.
Another example is when I was working at the computer repair shop. I just loved prying off the chips from the motherboard and looking at them. I would spend hours trying to figure out how all these pieces fit together. Eventually, that culminated with me building my own computer when I was in high school. There were those things that I look back on now and I think that’s totally me. That’s what I need to be doing.
Practically speaking, you want everybody you interact with to know your story, because stories are very memorable.
How do you weave your story into the interview?
Practically speaking, you want everybody you interact with to know your story, because stories are very memorable. You want to be remembered, so everybody who you talk to and who you are trying to make an impression with should know your story. They should be able to remember who you are when your name comes up in a big list of resumes — even if it’s just a little bit. There should be a spark of that story. Every time you go into an interview, you want to think about how you can tell your story. Maybe it’s when you get asked behavioral questions, you are putting little bits of your story out there and kind of weaving it into the question. That’s probably a little easier in the sense that you don’t have to go out of your way to inject it into your answers. You can think about it before and prepare an answer. Usually, when you get into an interview, the first question is to tell about yourself. That is a perfect opportunity to give a 30 second elevator pitch.
What is the best way to engage with recruiters?
Follow-up is critical. If you don’t follow-up, you don’t care. That’s not acceptable if you’re competing with other people for really coveted jobs. The follow-up is easiest piece to miss, but it’s so easy to do. Some people go as far as writing handwritten thank-you notes. I think that can be a little tricky, because it’s easy to come off as trying too hard. You’ve really got to know the people that you’re thanking and ask whether those people would really appreciate a handwritten note. I think a simple email after an interview is appropriate. It shows you have the follow-through and that you care. If you can tie in a personal question or personal point with that specific person, that goes a long way.
For a long time I had been living a set of adopted values and expectations. I wish what I had been told earlier is that you get to own your values.
What do you wish someone would have told you?
I got very lucky in my internships and that I ended up in the Bay Area. I think a lot of things clicked into place for me, but there was a lot of room for error. It wasn’t until I was well into my first job that I started thinking deeply about my values and owning my values. For a long time I had been living a set of adopted values and expectations. I wish what I had been told earlier is that you get to own your values. You have to own your story and what are doing and why. If you don’t own it, somebody else is owning it for you. Other people will create values for you, like the mom who really wishes the best for you but wants you to be doing this consulting job and making six figures coming out of college. Or your friend who is looking at a certain type of job in a certain salary and wants you to fit in with them, so you kind of go along with that. You need to take ownership earlier on so that you make fewer mistakes early in your career.
What should a student do, while at WashU, to figure out what they want or do not want?
Talking with people and establishing relationships is important. The classic wisdom is to go build your network. That’s true. You should be building a network with people you know, but I think specifically, when you’re in college, you should have this posture of wanting to learn. When you have that, it’s really easy to reach out to somebody who is a few years, a decade or five decades out of college and ask them for advice. You can learn a lot from doing that. Talk to the career center. Find people through LinkedIn and Facebook, go through your fraternity alumni archives, look up people and send them an email. I get emailed by students at WashU about the tech world often and I jump on the opportunity to respond. I like the idea of helping somebody get out here or helping them think through career problems that they’re thinking about. I just love doing that, and even if people don’t, I think most people would at least field questions if you ask.
What questions or what type of person did you find most helpful?
People straight out of college are extremely helpful, because they just went through the job process. They are in their first job. The next cohort, from 5 to 10 years out — those people are probably really busy, so it’s very difficult to get quality time with them. It’s more challenging, but I think equally useful. I actually think it’s beneficial talking to everybody. I also love talking to older people who don’t have the weight of college expectations weighing them down. They’ve been through their lives and they’ve seen a lot of things. They have a lot of life advice because they’ve already been there.
What did you do at WashU that was extremely valuable or helpful?
For me, it’s pretty easy. I was on the Crew team, so I woke up at 4:30 in the morning five days per week for the entire year, except for holidays. It was a really insane commitment, frankly, in retrospect. I cannot believe that I did that. I made so many sacrifices by doing that, but I’m so incredibly thankful for having had the opportunity in college. Part of it was the mental and physical aspect of doing an extreme sport, where you are pushing your boundaries every day. You push boundaries you could have never imagined. You’re physically fit and you’re mentally strong because you know that you can endure difficult things. I think that certainly helped me mature. It also helped with discipline and time management. Probably more than that, there’s something extremely satisfying about investing in one thing and getting really, really good at it. It applies in the professional world too. I would much rather work with somebody who is best in class at one thing than somebody who is mediocre at everything. I think Crew gave me an opportunity to be really good at something. It’s really tantalizing.
How do you find your mentors?
Building relationships with mentors is really hard. It takes a lot of time and is really not obvious. There is no formula. I think you want a mentor in your company, in your profession outside of your company and just a mentor in life in general. With that framework, I want at least one mentor in each of those buckets. Very few people just ask someone cold turkey to be their mentor. But, if you meet somebody who interests you, you can make an effort to develop that relationship. That’s where you can start creating a mentorship relationship. At some point, if you get to know somebody well enough, you can ask them very intentionally and very explicitly if they will be your mentor. Other times, mentors don’t know that they’re your mentor — they’re just happy to offer advice. There’s this guy named Victor Chang, an ex-McKinsey consultant who writes great content about how to get consulting jobs. I would consider him a mentor of mine. I love the way he breaks down problems and I’ve learned so much through his writing, but I’ve never actually asked him to be my mentor.
When you have a list of values, it’s actually really easy to decide what to do.
What other wisdom do you want to share with current WashU Students?
The story thing is big. I think also what’s really important is in line with this idea of values and starting with the fundamentals. I think I skipped a lot of that, and now I’m playing catch up. For the last couple of years I’ve been playing catch up and taking ownership of those things. It’s important to ask yourself what you want for your life and why. Being able to actually answer that and buy into your own answer is so important, freeing and awesome, but also really hard. For me, one way to answer that question professionally is that I want to create value for a lot of people.
I think about the founder of Clif Bar, Gary Erickson. He had an opportunity about a decade into the start of the business to sell the company for $100 million. He would have split that half way with owners and would have netted $50 million from having built Clif Bar. He declined that offer because he thought that being in control of that company, being able to influence the the world and create value for the community, employees and people in the world through the company was way more than he could ever do by being a super rich philanthropist. That idea is really compelling to me, and that’s one of the things I would love to be able to do. So with that, if I could have answered that question 10 years ago, I would probably be in a different place because it really clarifies and refines what’s important to me. When you have a list of values, it’s actually really easy to decide what to do.
Any other wisdom?
I can’t say this enough — being able to tell your own story is an incredibly important skill. I think about pursuing these triathlons, which I do in my spare time. Two years ago, my wife and I did an Ironman distance triathlon. I was thinking about why I would put myself through the sacrifice of training for this 140 mile race. For me, it was two things: one thing is I saw the Ironman as an opportunity for me to be the best in the world at something. Both Audrey and I came in in the top 10 percent in the world in the year we participated. That’s an example of something I committed a huge amount of time and effort to, which paid off because I can say I am one of the best in the world at doing that thing. The other thing is that the Ironman made me feel alive. Physically, it’s so demanding. You don’t typically get an opportunity to push yourself like that. That’s not to say that everyone needs to go do an Ironman. That’s to say that there are lots of things that you can do with your time that create a lot of value in your life and make your life extremely meaningful.