How I Got Here: Episode #12

Mike (00:05):

Welcome to How I Got Here, a podcast from The Garage at Northwestern, exploring interesting journeys of young professionals working at exciting companies, and the role that entrepreneurship played in getting them there. My name is Mike Raab, and I love dissecting non-linear and non-traditional career paths and the lessons that we can all takeaway from those who forged them. In this episode, I’m joined by David Olodort, a data analytics manager at Flexport in San Francisco. Earlier in his career, David got involved with a student run business and quickly realized the benefits of having hands-on experience running a company.

Mike (00:36):

His work running a student storage company gained him an unsolicited offer to intern at a startup over the summer, which translated into a full time job offer after school. In this conversation, we discuss the importance of diverse experiences, how to approach your job search, and how to think creatively about opportunities. I hope you enjoy this conversation with David Olodort.

Mike (01:06):

David, thank you so much for being here with us today.

David (01:08):

Thank you for having me. It’s my pleasure.

Mike (01:10):

Of course. Happy to have you. I thought we could start with taking us back to when you were a freshman entering college. What was your major and what did you think you were going to do after school?

David (01:22):

I was a mechanical engineer for two days. I joined Northwestern, really excited about working in mechanical engineering, and then I realized you can join industrial engineering and you don’t have to study thermodynamics, and fluid dynamics, and organic chemistry and all these other areas that I realized I really love still basic science, but I liked more of the application of it towards practical settings and in the business setting. Following into industrial engineering was perfect for me. It was a great way of applying … I often refer to it as essentially economics with an engineering bent, how to optimize and better quantify the business logic that is floating out there.

Mike (01:59):

Yeah, that makes a lot of sense. It sounds like first of all, that has to be one of the quickest major switches in history. Two days in. At that point where you realized you’re interested in industrial engineering over more of the hard sciences of mechanical engineering, did you know what you wanted to do after school at that point? I mean, it was a far ways away. Were you just in exploration mode?

David (02:24):

Very much so. Throughout high school I’d taken on different internships in more of the research and engineering space, and that was when I began to realize that I didn’t want to do as much of the academic experience within engineering, or deeper research, but I wanted to be more business and customer facing, but I didn’t yet know what that meant. When I arrived to Northwestern, I also had no idea what the words consulting or investment banking really meant. I soon learned afterwards a lot about those industries, as well as many of the other professional industries.

David (02:55):

But I knew really almost from the beginning that those didn’t strike me as something I really wanted to do personally. That’s why I very much suggest people to always take a variety of internships, especially in college. It’s a very safe way to explore and find out what you don’t like, which is much easier and more valuable than what you do like.

Mike (03:12):

Right. That makes a lot of sense and I completely agree with you. I think it’s important to be plastic and flexible in what you think you want to do after school. If you take an internship in that field, and it does not excite you and you don’t think you want to continue, then try something else. I think that’s great advice. It sounds like you were most interested in kind of getting practical hands-on advice rather than … Not rather than, but-

David (03:42):

I’d say rather than, yeah.

Mike (03:42):

Okay, I was going to say rather than-

David (03:43):

No, actually, [crosstalk 00:03:45]-

Mike (03:44):

… classes and stuff. How did you seek out getting hands-on experience in the business and application world that you were interested in?

David (03:54):

I took to heart some good advice from actually a mentor in seventh grade, all the way back in middle school which was, “Don’t wait. Just dive in and start getting involved with a bunch of things.” And you can always peel back, and I tried to do that at Northwestern, as well, too. I ended up finding some activities that really meant a lot to me. I certainly encourage folks to try a lot in college. Get out there, see what’s there, and then realize what really is both most valuable and what you most enjoy and do those.

David (04:20):

For me, that was an organization in Northwestern called Northwestern Student Holdings at the time, now Student Holdings. There’s different versions of it at other schools, as well, too, and essentially we were a student business group running real businesses, starting and running them, not just creating a pitch deck and saying, “Oh, I’d like to do this idea.” But then actually taking the money within organization and trying to make it real. That was by far the most transformative experience for me at Northwestern. More so than all my classes combined.

David (04:48):

The ways that I grew in that, there are many business lessons that I say, of having to learn how to hire and train a workforce, and how to manage people, especially manage those older than me in an organization, and finances. I could get into all those details and I think those are important and what was more important for me was how it galvanized me. How I think I came out of it with a much deeper appreciation for, and I now look for this in the teams that I hire in my current role, managing some data analytics teams, is a sense of ownership. I think that for me is one of the more important qualities of an entrepreneur, someone working in a startup space.

David (05:32):

Because you’re not working in a massive corporate company where there’s all these checks and balances and performance reviews and the bureaucracy of ensuring every little thing gets done. Things are going to slip through the cracks if someone doesn’t step up to do it.

Mike (05:46):

Yeah. Just to take a side tangent for a second, how do you identify someone or teams who take ownership as you mentioned?

David (05:54):

It’s a good question, because it’s very hard to do in interviews. The best way we can do that is having them talk through experiences and one thing that I look for is that spark that comes alive when someone is talking about experience. You can feel that they really, they dug in and they explained not why they did it for any external reason, but why they were doing it internally.

Mike (06:17):

I want to dive back to I think you were a freshman when you were getting involved with Student Holdings. You show up, how do you initially get involved, and what type of businesses or companies are being incubated and run there?

David (06:30):

The way that I got involved was we were running … The two businesses that I was assigned to, one was a transportation business to the airport. This is going to sound archaic now because Uber did not exist back then. Actually, this was a great business. It was highly profitable. I used it, other students used it, it was very successful. Chartering buses at set times, between airports and college campus, at the holidays. And that involved a lot of logistics, as well as marketing.

David (06:58):

This was my first foray into what is commonly called now guerrilla marketing, on campus, of plastering the campus with posters, and making funny videos, and getting the right kinds of social media postings and email campaigns to understand email analytics. This was very exciting. I think taking on this kind of work, and you could do this in any format on a college campus, learning how to market to customers is … One, it’s very important, if you want to learn how to grow a business or start a business. Especially if you want to start a business, because you’ll have to be the first marketer to do this.

David (07:29):

And I think the campus grounds are a great foray into this. Because one, it’s a very unique customer base where you are both the customer and the customers are also your peers. In some ways it’s very homogenous where it’s a bunch of students who are within the same four years. And in some ways it’s incredibly diverse where you have tons of different kinds of students who have different interests and needs and backgrounds and wants. It’s a really fun way, at the same time, because you can get fun with the marketing to learn how to market. That was one of the businesses, and then the other one which very much became my … Well, my business baby moving forward, and the thing I became so attached to, was BoxCo.

David (08:15):

We were a storage and shipping company, so at the beginning and the end of the school year and over some holidays, we would pick up students’ items, store them, and then deliver them back in the following year. I was a part of this throughout my time at Northwestern. I ended up leading part of the marketing team my freshman year, and then I ran the company in my sophomore year which is by far the most transformative experience I had.

David (08:37):

What I ended up doing as a sophomore was learning how to run this business and that involved managing a team of a dozen other peers, other students that were part of this management team, hiring and training a workforce of about 90 laborers, other college students, high school students in the area, locals, to help run this business, this very manual business. Figuring out all the logistics for warehousing, inventory, truck scheduling, pickups, and so on. The marketing again, of this, because there was a fierce competition with a couple of other competitors on campus, as well as the pricing and financing of this and making sure it was a profitable enterprise.

David (09:18):

There was a wide variety of experiences that I got to pull from, and I think that’s one of the benefits of joining, in this case, a small company essentially, rather than starting something fresh as I had been a couple of years previously, is for me it was much more about operating at that point, and growing, rather than starting. My sophomore year, I ended up growing it from about 340 customers to over 840 customers. It was less about, “Hey, does this idea work? Is there product market fit? And what exactly do we do in this scenario?” It was, “Hey, we know what we need to do, and now let’s just get much better at it.” There was a ton to do.

David (09:55):

I think that’s the other thing, going back to that earlier comment about sense of ownership, is if you can tell … You can tell in a conversation when someone is very passionate about whatever topic it might be. Often times actually, I know I’m skipping ahead, when I’m now interviewing folks for my team, managing, or actually I was doing this yesterday for another team that I don’t manage, just helping with some interviews, one of the questions I often always ask is, “What are you excited about learning next?” I don’t really care what they say, I care how they say it. And I care what they bring into that conversation.

Mike (10:29):

Yeah, that makes a lot of sense, and it sounds like it was a super valuable experience to you. I’m curious, though, coming in as a sophomore to actually manage and run this company, manage a team, all these operations and stuff, were you confident and comfortable in doing that? Did you have impostor syndrome? Were you okay delegating tasks? What was your mindset and how did that evolve throughout your experiences doing it? Then what did you learn based on mistakes that you may have made?

David (10:55):

It’s a wonderful question because I think I was too naïve and too young back then to have impostor syndrome, which I can chuckle a little bit about now because actually I very much have felt that in my last couple of years, managing in a much more serious endeavor now in my current job, and having impostor syndrome and working through that. And knowing that, I did not feel it back then. Back then, there was certainly times where I felt overwhelmed. I remember actually the first time I was meeting the chairman of our board, and I was late. I was late to the meeting, I made some mistakes and he wasn’t in a good mood.

David (11:27):

I came back to my dorm room and I just started crying a little bit on my bed. I remember sitting there thinking, “Wow, what have I gotten myself into here?” Luckily it turns out the chairman incredibly jovial fellow, very supportive, and I had the right people around me. But that was the first thing I did, was I began to realize I needed a support system. I was not good to begin with about knowing when to say, “I screwed up.” I think this is a common problem, especially back then because I felt, “Oh, I mistook taking on more responsibility and leadership as therefore having to be more perfect.”

David (11:59):

And in some ways it’s actually I think the opposite to some degree, or at the very least, there’s more of a responsibility to speak up and be transparent about where I needed help, where I made a mistake, and therefore set the right example for my team. As I was talking about earlier, I want to do that with my team, too. I want to make sure that they can be vulnerable in the right way, to have a physiological safety.

David (12:21):

These are all things that I think often times can get brushed over as like, “Oh, you need a really smart hard working team” and like, “Oh, it’s also nice if they’re good people and they can do this other stuff.” Sure, I need people who know how to do a particular task, or actually, can learn how to do a particular task and have the right kinds of capabilities. But this is much more fundamental, and if we go back to Maslow’s pyramid, the idea of physiological safety, same thing in a workplace, too, and what we’re doing. That was challenging for me.

Mike (12:51):

Right. In addition to having this very, as you mentioned, transformative experience with NSH, you also had some internships during the summer. Can you just describe briefly what those were and how they ranked in comparison to your position with NSH?

David (13:07):

Certainly. After my freshman summer, I worked at a small boutique consulting firm that worked with both non-profits and for-profits to help create campaigns for the non-profits sponsored by the for-profits. Frankly, did not learn much that summer. After my sophomore year, I worked at Medline Industries which is a large national medical manufacturer, and just North of Northwestern. That was in a much traditional, industrial engineering role. It was when I was still exploring, I was like, “Well, actually maybe I’ll go all in on this IE thing and see what it’d be like” and I enjoyed the quantification of the business that I was seeing around me. It was very tangible. I got to be in the warehouse. Pardon me, the manufacturing lines, and I’d go down and talk with the manufacturer and employees and understand what these numbers or these formulas I was working on would actually do in the real world.

David (14:00):

But I realized through that experience well, okay, I knew before I didn’t want to go into deeper engineering research or academia. I learned I didn’t want to do more of the technical application around the hardware side in mechanical engineering, and now I realized I also didn’t want to do more traditional industrial engineering, but I liked the concepts of it and how I was applying those frameworks. Then my junior summer, after my junior year, I worked at a company then called Context Media, now called Outcome Health.

David (14:26):

That’s the company I ended up actually joining after graduation. And that was the first taste of what I mentioned earlier in our conversation, about diving in and just doing it all. But when I joined, I joined, there was about 150 employees, as an intern. I have to say, that’s a beautiful size to join. Because by the end of the summer, I knew everyone’s name, including the people who’d been joining because the company was growing quite quickly, and I got to try a variety of experiences and projects. And it was also … The work I was doing was impactful and that was really fun.

David (15:00):

That was what sparked for me, or maybe cemented I should say, my interest in working in both the tech sphere, as well as working in the analytics space but I began to realize, “Oh, I really love this idea of now applying some structured logic, some ideas, some rules.” Essentially if then statements, but more complicated, to these business problems.

Mike (15:23):

Yeah, I appreciate that. But just to take a step back for a second, it sounds like you were super fortunate that your first couple of summer internships, you learned those were things that you didn’t want to do, and then your third one you got really excited about analytics and tech and startups. How did you get the opportunity to intern at Context Media/Outcome Health?

David (15:43):

Well, I feel fortunate in that, as well. Fortunate for being in the right place, but I certainly earned it. At the time, one of the founders of Context Media was on the board of Northwestern Student Holdings, the group that I was a part of. She’d been one of the co-founders years past, and I’d been giving a board presentation on my work in BoxCo. I remember getting email from our chairman a couple of days later, who said, “Oh, [Shada 00:16:08] would like to speak with you and chat.” I didn’t know what she was doing or anything about the company, and I was like, “Okay, sure.” We had a couple of good conversations.

David (16:15):

I wasn’t really certain, and then a couple of months later she called me again and just offered me the internship. I think we had a couple of interviews, or conversations, but it wasn’t really like an interview. I learned then you can be interviewing people even when they don’t realize it, in a good way. I certainly didn’t know that back as a college student. And that’s why I landed it.

David (16:36):

To me, I remember actually because frankly, and this might be applicable for many students, too, my outsized focus on my extracurriculars, on Northwestern Student Holdings, versus my academics. Well, one, it was clear in my grades which again, I wish I’d actually spent some more time on. But also, too, it then became clear to my parents. It was a point of contention. I will admit that being able to speak to well, it literally got me my job, was helpful. And of course, anecdotal, but I think it was important to show that there are many ways that you can be prepared for work outside of college and there are many ways that you can demonstrate those values and what you’ve gained out of it to others, beyond even just the resume, too.

David (17:24):

Because my resume bullet points for BoxCo, sure, they might have been impressive to me a couple of years before I realized I was going to be running a company that had hundreds of thousands of dollars in revenue, and hundreds of customers. But I don’t think that’s why Shada hired me, or I don’t think that’s why, as I said, I felt more prepared moving forward. I think it was the how I grew out of it and how I could speak to that and articulate that in the conversation.

Mike (17:50):

Yeah. To use your terminology, I would guess that Shada also saw that spark in you and that ownership of your work with BoxCo, and your excitement for it.

David (17:59):

Well, thank you, yes. And I think, again, being able to tell those stories is important. People talk about this as being a founder or a CEO and being able to tell a narrative. It’s true. But I think it’s very cliché, but you’re your own CEO. In some ways, that’s very true. Tell your own story. Whatever that might be. As I said before, I don’t really mind as much what people want to learn next. I just love to see that spark.

Mike (18:23):

And so you mentioned already that you ended up working for the company after school, as well. Did you get an offer at the end of the summer or how did that opportunity come about, to continue working with them?

David (18:33):

It was a moment of brief anxiety I’ll admit. I learned at Northwestern, I said at the beginning that there became two jobs. There was consulting and iBanking. Of course, there are more. I also then began to learn that, “Oh, if you do a good job in … If you do well in your junior internship, then you should get an offer at that company and you’ll be set and maybe you’ll want to interview elsewhere, but at least you’ll have one offer.”

David (18:55):

And I thought I did a pretty darn good job. I was always getting good feedback from folks and everyone knew my name and I was doing lots, and running around the office. And then I had my final interview, I won’t even call it an exit interview. Or sorry, final meeting with my boss, who was a more … Not a very traditional fellow. He just ended the meeting and there was no offer. Just, “It was great, this is wonderful. Have a good weekend.” I walked out and I was like, “Hmm. That sort of felt weird.”

David (19:25):

One, I learned then that you have to … You can never take your career path for granted. You have to speak up about it. Turns out, this individual, he didn’t mean poorly. He didn’t have that expectation. He wasn’t very experienced in this area, and so he didn’t know he was supposed to be offering, but I had to also speak up in the case. I started talking to [inaudible 00:19:42] like, “Hey, I think we should have a conversation about this. I would like to work here again. What do you think? You seem to be very happy with me.”

David (19:49):

And again, I think that was a very small, easy way of saying, “I need to speak up for myself.” I ended up getting an offer. I remember actually, they were growing so quickly, he tried to get me to drop out of college to join. I’m very glad I didn’t for a variety of reasons. I can’t cancel everyone and all their decisions but for the most part, I think it is … In this case, I will use the word prudent, prudent to finish out an educational career and grow.

David (20:14):

Turns out I joined a year later and it still had an amazing experience. It was certainly the right decision at the time. I wasn’t trying to be rash. But I did also interview at some other places senior year because I learned in the same vein of trying different internships, I wanted to see what else was out there, as well as then how would I compare it to? “Oh, now I got this offer from another company. How do I really feel about that versus this, the return offer?” It made me at the end of the day feel much more comfortable actually about going back to Context Media, because I’d interviewed at other companies, I’d gotten an offer from Capital One, and I realized, “Oh, for these variety of reasons this was actually the better opportunity for me to go back to Context Media,” and it gave me a lot more confidence to do that.

David (20:58):

I loved it. I got so involved. I was contributing a lot, I was growing, people seemed to be very happy with my work, I was getting very excited about it. And that led to a lot of great things, but it also led to work/life balance or the lack thereof for me. This came to a head a couple of times. I remember one time I burned out very hard, and I hadn’t really felt that sense before. I’d been working maybe 80 hour weeks, and I hadn’t been taken as good care of myself physically, and I was just focusing on work all the time. I’d go to bed Slacking my boss, I’d wake up Slacking my boss, I’d be doing fire drills all the time. “Oh, the CEO needs us in three hours or four hours.”

David (21:33):

And it’s a good short term high where I felt like, “I’m contributing, I’m doing great, I’m doing these things.” I certainly didn’t have the longer term perspective I have right now on both but the other thing I wasn’t doing, I wasn’t thinking about, “Am I investing in myself the right way?” And this goes back to my learnings from Northwestern Student Holdings early on. How much am I learning from this experience? How much am I just growing as an individual? What are the ways that my character’s developing? Who are the people that I’m meeting, the experiences? I wasn’t thinking about that fully. I was giving too much, in this case, to the company. And I needed to be more thoughtful about it.

Mike (22:08):

I think that’s such an important lens and perspective to learn early in your career about how to evaluate opportunities. You end up working at that company for about a year and a half, before you leave without having secured another job. Can you talk a little bit about that decision and what your job search process for your second role was like?

David (22:31):

The reason I left Outcome at the time, I could talk about for a long time. But in short, it was the company was imploding for fraud reasons, for fraud allegations. Things I was not a part of, but the executives were. And I knew I didn’t want to be a part of that place anymore. In fact, I’d actually been involved in a lot of the cleanup work that customers had been asking for, and it was incredibly stressful. It was the one time I’d ever snapped, and I broke down. I had a horrible moment, and that was when it really hit me, that I had to start taking better care of myself.

David (23:05):

Life hopefully is a very long marathon, and I cannot just sprint through it quarter to quarter, or day by day. It’s just not sustainable. Nor of course, a fun or healthy or positive way to live. But what I realized was at the end of the day, for a variety of reasons, it was better for me to leave at that time, and make that personal decision, than wait for another opportunity. Now, this is certainly a more unique instance, but I think it did teach me a lesson moving forward, which is sometimes that’s still the better decision. Which is to leave when you have the right kind of resolve, rather than wait for some external event or push.

David (23:42):

I’ve talked about this now with some other friends in frankly, in some private equity roles, who know they’re unhappy in it for their own reasons. It’s not just the industry, their own management issues, that they know they’re unhappy in it, and yet there’s always another carrot. “Oh, we get this bonus here. Oh, but there’s this other deal coming up.” It’s always going to be true, in whatever instance. I knew I had to make that decision, and it was hard. The reason it was hard is I then felt very uncertain. I was like, “Oh no, I’m suddenly unemployed” and I’d always felt, I tied a lot of my, at that time, self-worth to that achievement.

David (24:16):

I like to think now I’ve diversified my findings or the roots of my self-worth beyond that. But at the time it was challenging. I ended up in a three month process of looking for a new job. A few things that came to mind there. One is it was very much about understanding my network of people who I knew, and more importantly who they knew. So many folks who a friend of a friend who wanted to help out. You’ll find that in your own searches. Let the computer do the work for you. Humans are very good at creative thought. We’re not, as these analog machines, we’re not great indices of all this information.

David (24:57):

LinkedIn is amazing, let LinkedIn figure out for you who knows who at this other company. Don’t ask someone, “Oh, who do you know?” Because I don’t know that my middle school classmate happens to now work at a company with someone else who you want to go talk to. I’d have no idea, but LinkedIn can figure that out for you, or other programs. Taking advantage of that and seeing what else was out there was important.

Mike (25:19):

Yeah. Obviously you end up at Flexport. How did you get connected to that opportunity and what about it attracted you?

David (25:26):

Very lucky to have good friends from Northwestern. One of my friends, Will Ginsburg was a part of Northwestern Student Holdings with me, and he knew another Northwestern alum, Avery Alchek, who was working at Flexport at the time. We connected and Avery was incredibly nice to help me land the job. The reason that I was attracted to Flexport was I joke that the days of BoxCo came back to me where I loved … What we talk about at Flexport is the atoms, not the bits, and that we’re moving real things. With software. But it’s a very tangible experience.

Mike (25:58):

It’s interesting that Student Holdings has effectively landed you both of your jobs after school. I have a feeling I know what the answer to this last question might be, but looking back, what advice would you give to yourself as a freshman? As far as thinking about a career and what activities to do, or how to think about planning your career as a college student.

David (26:20):

It’s a very good question. I think what will be important to me is I would want my earlier self to be more creative in thinking about the opportunities that are out there. I think you have the opportunity as a student now, in college, to run a business that isn’t profitable. Maybe you end up paying $100 a month to run that business, because that’s what your P&L is, but you learn so much throughout, or you try this new idea that someone wouldn’t fund otherwise.

David (26:48):

I would encourage folks to keep getting more creative with what’s out there, because it also then will encourage I think the realization that there are many more jobs out there, or even professional opportunities than one might think. But to realize there’s a lot of wonderful ways to earn a living and to make a living out of it, and frankly, I’m telling this advice to myself right now too, as I think about how can I attract even more fulfilment out of my own work? I don’t think I’m 100% there. I don’t think any of us ever do get there, but I think what’s important is to keep striving towards that and find work that matches even more of what I’m looking for. Learning and applying that early on in college I think is important. Otherwise, it can be hard to take the horse blinders off.

Mike (27:28):

I think that’s great advice. I could continue to talk to you and ask questions for hours, not only because you have great perspective and experience and advice, but you also have a great voice for radio or podcast.

David (27:40):

Well, thank you, Mike. It’s been a pleasure chatting with you, too. We could keep doing this. Let me know if there’s a sequel.

Mike (27:44):

Sounds great. Thanks so much for your time and advice, David. Good luck.

David (27:47):

My pleasure. Have a good one.

Mike (27:49):

Bye. If there’s one lesson I would takeaway from David, it’s the value of finding something to take ownership of and how that spark can open up opportunities in your future. Even if a startup idea you work on doesn’t yield a financial windfall, the lessons you take away and a passionate story you’ll be able to tell others will lead to unpredictable opportunities in your future. If you have an idea you’re excited to work on, I’d encourage you to just get started.

Mike (28:13):

How I Got Here is a podcast from The Garage at Northwestern, and is produced by Melissa Kaufman, Ben Williams, and Elisabeth Wright. If you enjoyed this episode, please rate and review us on your favorite podcast platform.