How I Got Here: Episode #1

Mike Raab (00:06):

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 Rapp and I love dissecting nonlinear and non-traditional career paths and the lessons that we can all take away from those who forged them.

Mike Raab (00:24):

In this episode, I’m joined by Connor Regan who currently works in global product policy and operations at YouTube and has served in a number of different product marketing manager roles at Google since graduation. As a college student, Connor took on 11 internships during his time in school at a variety of companies from startups to incubators, to consultancies and tech companies. In addition to working on multiple student startups.

Mike Raab (00:47):

Connor’s strategy of seeking out diverse experiences instead of maniacally focusing on a singular path stands out in a world of increasing specialization. I hope it gives you something to think about.

Mike Raab (00:58):

One quick note, this recording has a few glitches due to an unstable internet connection, but it should hopefully not be too distracting or confusing. That said, I hope you enjoy this conversation with Connor Regan. All right. Well, Connor, thank you so much for being with us here today.

Connor Regan (01:19):

Yeah, thanks for having me.

Mike Raab (01:21):

I thought a good place to start would be if you could take us back in time to when you were just starting college, what you were studying and what you thought you wanted to do after graduation.

Connor Regan (01:33):

Yes. A couple of years back now. I started at Northwestern studying economics. Fairly early on, realized that, while I was interested in economics and found a lot of value in the study, I might’ve had the wrong intentions in choosing econ. I received a lot of guidance that said if you want to go into business and you go to a school like Northwestern, where there’s not a business program, you can only study economics. That is the option.

Connor Regan (02:10):

I was fresh out of high school. I had no basis on which to refute that, so I kind of I went with it. While I did like econ, I started to realize, actually, there’s a lot of paths to business. Maybe more paths to business than there are to most other things. You can, in some ways, actually, I think, take weird paths to where they end up, sometimes have the most interesting contributions because they did the uncommon path there.

Connor Regan (02:48):

For me, I ended up finding learning and organizational change in the school of education and social policy as a bit less conventional, but interesting approach. Basically, the way I describe it is the bringing together of psychology, sociology, a bit of business, all mashed into one. For me, that was super valuable.

Mike Raab (03:17):

Got it. So, your intention was always to, even though you switched from econ to learning and organizational change, to still, at graduation, work in some business or strategy role or something like that.

Connor Regan (03:27):

Yeah, exactly. I thought from the beginning that I wanted to be a consultant. At Northwestern, I think there are many students who … You come into a place like Northwestern and you have no idea what consulting is, but you hear consulting a lot. Oh, well, I guess I need to be a consultant. I was definitely in that group. Certainly, no shade on consulting. I actually think someday I might want to still do consulting. But again, already, I can see a theme here of a default. That was it for awhile.

Connor Regan (04:07):

Then, as I started gaining like what I would call real working experience, taking ships, even joining student groups where I was learning the art of business by doing it, instead of just reading about it or watching narratives play out on TV or whatever, I realized that there are a ton of things in this world of business that you can do. So, over time that shifted.

Connor Regan (04:32):

There were times that I was deadset on consulting, like I said. There were times when I was like, okay, I’m going to a startup. I’m going to get in on the ground floor of something. For a while, I played around with creating my own startup. Many a path I explored, I suppose.

Mike Raab (04:50):

I want to dig into a lot of those paths, but the first one, because it seems the most unique, and I think I haven’t seen this anywhere else. But if someone were to look at your LinkedIn, the number of internships you had as a college student is very impressive. Can you talk about what your thinking and strategy was to have so many internships? Maybe describe a few of them, and if they were all similar or if they were very different?

Connor Regan (05:16):

Yeah, absolutely. There was indeed a strategy there. I think when I arrived at Northwestern, like many students do when they arrive at college as a freshmen, regardless of where they go, this kind of … I used to be a big fish on my high school campus and now, I’m in this pond that looks very different than the pond I was used to. I think that hit me hard. I think it hits many people in that way.

Connor Regan (05:48):

But for me, I had this introspective, especially in that fall quarter, where I tried to think about, okay, I’m struggling in my classes more than I have in the past. I’m used to just everything being easy and all of a sudden, college is actually a challenge. I actually study for things now. There’s so much that I can dig into, and I’m kind of overwhelmed by all the things I’m saying yes to before I even can really do an analysis to determine what I should be saying yes to and what I should be saying no to.

Connor Regan (06:27):

My freshman year is when I started this crazy internship, I don’t even know what you want to call it, journey. I just found so much value in going and being in real working environments. In some ways, actually, especially as a freshman interning, I was given bits and pieces of really cool strategic projects. There was also plenty of stuff that was just intern work. The stuff you see in movies or TV or whatever. It’s not necessarily glorious, but I was part of real organizations doing real things, creating real products for real customers.

Connor Regan (07:05):

That’s how this started. To the second part of, were they all the same, what were the differences, pros, cons? Definitely a wide variation. In some ways, I think that affirms the decision to do multiple. A lot of people doing a crazy number just isn’t the right decision because there’s other priorities for them. I think for many people, that is the right call.

Connor Regan (07:32):

But I do think that doing a couple gives you an opportunity to compare experiences. If you get to the end of your time in college and you’ve only done one, that’s not necessarily a problem, but you will probably make extrapolations from that single experience that might not be valid because it’s the one that you have.

Connor Regan (07:51):

For me, being able to say, working at this, I worked at a startup incubator for a quarter. Then, working at a startup and seeing things from two different sides, that was super interesting, to be like, okay, these two are in a much more evaluative state, looking at startups and investigating them versus the really scrappy, trying to build something, folks inside a startup. Totally different vantage points. Being able to compare them, that’s where I found a lot of the value.

Mike Raab (08:21):

I think that’s so wise. It was 11 internships that you had during your time, right?

Connor Regan (08:28):

It was 11.

Mike Raab (08:29):

I think having a breadth and diversity of experiences is underutilized these days. Like you said, I think a lot of students pick one path and just dedicate themselves to go down it. But having those, whether it’s different types of companies or different stages or different day-to-day experiences, just to compare and cherry pick of, I like this about this experience but I don’t like this, makes you much better equipped to actually go down a path that is intentional.

Connor Regan (09:01):

Yeah. I think that’s so true. I mean, even to something as maybe each project is management styles or leadership styles. I think it can be easy to be like, oh, well of course I want a manager who’s collaborative, and I want a manager who really trusts me, or whatever.

Connor Regan (09:21):

But a classroom exercise, even if you are in management classes, and going back to what I mentioned before, I wasn’t in quote-unquote business classes. Even that understanding of what are the inner workings of an organization like? For many students, experience, real experience, the best way to actually get a gauge on that.

Connor Regan (09:46):

You Might realize, actually, I want a manager who lays things out clearly for me. Maybe if you don’t have a ton of exposure, you see that as micromanagement or something like that. Or, there’s not a lot of trust in how they manage their workforce. I think it’s much easier to be able to like walk those very fine lines when you’ve a couple different experiences yourself.

Mike Raab (10:13):

Right. Especially when you’re still in school and you have the safety net that you’re not dedicated to this job until you find another.

Connor Regan (10:19):

Right.

Mike Raab (10:21):

You also mentioned a couple of times working for student startups and starting your own company. Can you describe your experience with those things for me?

Connor Regan (10:30):

Sure. Yeah. Basically, this organization that I joined had a portfolio of companies. My initial experience was in joining a small startup, a student run startup, and learning from other students who were in higher positions of leadership.

Connor Regan (10:52):

For me, it was a great way to join and be under the wing of students as opposed to real adults, if you want to call them that. Folks who could really empathize with the position I was in as a student balancing many different needs. I still, as much as I prioritized real world experience, I did indeed take classes. I did indeed graduate. All of that had to be balanced as well.

Connor Regan (11:21):

That’s where I started, the company that I joined was called Project Cookie. The name, it gives you a sense for what we did. We basically were a late night cookie business. We sold to students primarily at the two main libraries on campus at Northwestern.

Connor Regan (11:45):

In a lot of ways, this was a business that probably could only thrive as a student business. We were profitable, not massively so. No one was taking vacations on the non-existent salaries that they made. This wasn’t absolutely, primarily a learning experience.

Connor Regan (12:04):

But at the same time, it was also a real experience. Real customers, who were students, who were cash strapped, were spending money on our products. If our products weren’t good, they would stop. That’s how the real world works.

Connor Regan (12:20):

Same thing on the other side, the human capital side. If we weren’t treating the students who made those cookies and sold those cookies and did the inventorying and all of that, we didn’t treat them well and value them, they also would quit.

Connor Regan (12:38):

The pressure of the realness is part, I think, of what drove the learning. Is me realizing, if this is the late night student-run business, that means I might [inaudible 00:12:50] at 1:00 AM. We’re out of Oreos or whatever it is.

Connor Regan (12:55):

It seems silly talking about. But if I didn’t do … I couldn’t just say, “Uh-huh (affirmative), I’m asleep.” I have a midterm in the … If I didn’t do something, then real customers would be like, “What the heck? I just placed an order.” Or, “I’ve been waiting.” I think that for me was really important.

Connor Regan (13:16):

Moving on to the broader part of your question, that was the start, when I realized being part of something that’s small is giving me the opportunity to wear many caps.

Connor Regan (13:29):

Technically, I had a role. If I’m being completely honest, I don’t remember what that very first role’s title was because there were four of us running a business. That’s part of a startup is, yeah, you might have a title, but you’re probably doing quite a few things more than that title. That was super valuable. That’s what sparked my interest in joining a quote-unquote real startup.

Connor Regan (13:52):

I did a couple internships and startups that were doing a bit more than baking and selling cookies. But that foundation, though, of there’s not necessarily a lot of infrastructure here, there’s not necessarily a lot of support, so I could build it myself. That was exciting. I think that sparked an interest that then I explored over the following years.

Mike Raab (14:20):

Yeah. That makes a lot of sense. I’m curious, because obviously, you joined this group that had this portfolio of companies, but you also had gotten all these other internships. It would seem that you’re very good at either interviewing or convincing people that your work is good or finding ways to get opportunities or open doors for yourself. What do you think that is about yourself? What was your strategy in finding all these opportunities actually landing them?

Connor Regan (14:53):

That’s a tough question because I think inherently, we assume when it comes to processes like interviewing and applying for jobs, that there is a singular path. I’m going to optimize my resume so that it looks like the resume I think they want to see.

Connor Regan (15:14):

I think I, like many people, overanchored on, well, I’ll just … some juniors and seniors and ask them to coach me on what a resume should look like. That is a good place to start is find folks who will help give you a sense based on their own experiences of how you should be approaching this.

Connor Regan (15:40):

But to your question more directly, I think you do also need to stand out. If we all had the exact same resume and we were all were using that same group of seniors and just replicating them, that’s also not very compelling for most employers. Really being you, in a lot of ways, I think it actually is as simple as just really being you.

Connor Regan (16:06):

An example. In the beginning of my time in high school, not college, had gotten involved in this organization called … Best Buddies is a sister organization of Special Olympics. Basically, all kinds of career development, social development and friendship programs for people with intellectual and developmental disabilities. By the time I got to college, I had been doing this for five or so years. I always talk about Best Buddies when I interview. Because when I talk about it, people can tell that I really enjoy it and like it, and that it’s real.

Connor Regan (16:46):

Especially when I was much lighter on experiences, if I talked about other things, they might be able to read, you’re saying these things because they sound good or they sound right. But I made sure to talk about things that I knew the passion would show on my face and my inflection beat was real.

Connor Regan (17:02):

I guess my guidance to students would be, of course, you want to look at models that you can emulate people that are landing in the place that you want to land in. But you need to balance that with also that introspection I mentioned before. Looking and figuring out, what is important to me? And can I double down on certain things that by investing in things I’m already good at, or I’m already part of? Really making real commitments to things. I’ll be able to talk about those experiences in a way that is very authentic and compelling.

Connor Regan (17:43):

I think that, when it comes to interviewing, that’s maybe the biggest goal is to come across as someone who really means what they say. A lot of interviewing is trying to suss out how much of what you put in your resume is real. How much of the impression that I got when I read the single page do I really think is there and authentic? I think that is the best way to show someone this is really me.

Mike Raab (18:10):

I couldn’t agree more. I think there are two important points there that you emphasized. One is being authentically yourself. But the second is also differentiating yourself by doing the things you enjoy and are interested in, not just what you’re quote-unquote supposed to do. Or what, as you mentioned earlier, the default is. I think that’s great advice.

Mike Raab (18:35):

I know you also were involved a bit with The Garage at Northwestern. I’m curious what some of your takeaways or the highlights of learnings from working with other student entrepreneurs over there were for you?

Connor Regan (18:51):

Yeah. Working with students who were studying different things than I was was definitely one of the standouts. In particular, I worked on this startup that, at the time, was called 89 Robotics. We were building the first indoor drone intended for use, our very first concept was as a pet monitoring drone, so that you could check on your dog or cat while you were away from home. Which, the concept has evolved quite a bit.

Connor Regan (19:31):

But all that to set up is I was working mostly with folks who were hardware engineers or software engineers. Not more business-y people like myself. Some of the memories that stand out to me are applying a little bit of … How do we validate the market needs when we think about this really cool technical concept?

Connor Regan (19:59):

I might not have learned to think as much like an engineer if I weren’t working directly with engineers. I think that goes in multiple directions. If you, as a student, are listening to this podcast and you’re in engineering, it might be good for you to go and find some non-engineers to try and learn from.

Connor Regan (20:18):

That was a big one for me that The Garage just, very easy. The other thing is that there was a speaker series or a dinner series. The real value, besides the food, was getting to hear real entrepreneurs who worked on totally random things. Not necessarily where the industries that they were in, the thing that I was like, oh my gosh, you work at Google. I have to go hear you because I know I want to work at Google. Something like that.

Connor Regan (20:54):

One of the ones that really stands out in my mind, I’m pretty sure the woman who spoke was the CEO of a nannying company or something like that. I have no nannying. I’ve never been a nanny. I’ve never babysat anyone. But for whatever reason, that talk really stands out to me.

Connor Regan (21:13):

I think in some ways, that’s, again, part of the vastness exposure to business models, markets, consumer needs that maybe you yourself don’t know anything about because they aren’t your consumer needs. There’s not a market that you yourself is in. Being exposed to so many different ways of thinking, just bleed over effects.

Connor Regan (21:36):

Now, I could never have predicted it at the time, but I ended up in my first job out of college working at Google on a privacy and security team building a product for kids and families. I’m sure there were some takeaways that weren’t super conscious, but I had had these gears turning from some random talk from the CEO of a nannying company. That then, when I’m going out and trying to market to moms and dads, I’m able to tap into that knowledge.

Connor Regan (22:09):

I think like the exposure to things that maybe at the moment don’t slot perfectly into some master plan, I think there’s a lot of value in that kind of learning.

Mike Raab (22:20):

I agree. I think we’re seeing a strong theme here of exposure to diversity of ideas, experiences, and people has been a strength in your career. Speaking of, you mentioned when you graduated, you landed a role as an associate product manager, APM, at Google. Can you describe what the recruitment process was like and how you both picked, but also landed that role?

Connor Regan (22:45):

Sure. Yeah. I actually was an associate product marketing manager. The programs were are, one, even in name, very close. And actually, in how they’re set up, are quite close. But essentially, it’s a rotational program designed for new grads.

Connor Regan (23:04):

The value, we really are going to hit on this, this main theme over and over again, is that I got exposure to multiple things and it was built in. The fact that these programs exist and have existed long before I came to discover them is a testament to the fact that I’m not some pioneer in get diverse experience.

Connor Regan (23:27):

But anyways, so you mentioned the APM program. You start in a role for 18 months and then you are required to switch into something new. That was of great value for me.

Connor Regan (23:42):

Third big piece and what drove to apply to these programs and eventually accept an offer from one of these programs, is the focus on structured network building. I think for a lot of students leaving college, sometimes you’re able to predict it. Sometimes, I think it surprises people. But there’s a lot less structure in the real world than there is in college. When the quarter ends, there’s not a process for deciding, well, what classes am I going to take next quarter? A lot of those things that you start to take for granted as a student are gone.

Connor Regan (24:30):

For me, I valued a lot that I had this smooth transition into a way less structured working world and rotational program helped with that for me. For the record, for those listening, these are beyond product marketing and product management. I know of rotational programs in HR and finance, and they’re also beyond the tech industry. If something like this sounds interesting to you, I think it’s worth doing an investigation to see if something like that exists in the industry or company you want to work in.

Mike Raab (25:06):

Yeah, I agree. Can you just touch maybe briefly on all of the roles that you’ve had while at Google and where you are today and what you’re working on?

Connor Regan (25:15):

Sure. As I mentioned, I started in this … This is actually also an interesting one. The rotational program was in the marketing organization and my role was as a marketer. But in my very first role, I did a lot more than marketing. That’s something that I’ve realized actually is an element of many roles, that the job title does not reveal even a frack of all of the things that the actual job entails.

Connor Regan (25:55):

In that role, I was building a program, a product, if you want to call it, for kids and families designed to help keep kids safe on the internet. The insight that was driving was that people were feeling disempowered when it came to technical concepts like encryption and fishing and malware, because they felt foreign. My goal was to find a way to really bring these technical concepts down to earth a bit and make them more accessible and find a way to make them engaging as well.

Connor Regan (26:36):

I love that. It’s super interesting. But then, this is going back to what I mentioned before. Then, I was forced to leave, because that’s part of the program. I was loving it. I was one of those people who was like, oh, I could actually do this longer. Do I have to leave? While I still love that team and I catch up with members of that team all the time, I am glad that I was forced to go do something different.

Connor Regan (27:03):

This is not going to sound surprising for anyone who’s been listening. I decided to do something totally different. Again, back to that diversity of experience thing, I moved across the world, halfway across the world-ish, to essentially get a global working experience because I had not studied abroad as a student. Right when I graduated, I regretted it. It was like, why didn’t I do this? An opportunity presented itself to go and work abroad.

Connor Regan (27:36):

I moved to Amsterdam and joined Google’s Northern European retail marketing team. I was working on hardware products from Google and Nest. [inaudible 00:27:49] Nest cameras and thermostats and all of that. Completely different than privacy and security. Again, found a ton of value.

Connor Regan (27:57):

I had never been conversations with retailers where we are trying to actually sell something. When I was working in privacy and security, we weren’t selling anything. It was a very different world, and yet my title was the same.

Connor Regan (28:12):

Again, going back to what I mentioned before, and I think this is … I remember being a college student and looking at LinkedIn and trying to read between the lines and figure out what do people actually do based on these titles. That can be really hard because I was an APM in both of these experiences. In one, I was selling Chromecasts and the other, I was building a game for kids.

Connor Regan (28:36):

Anyways, we’ll move on from that one. I had a great experience living abroad. In a lot of ways, I think the value was even more so on the personal development and the professional development front. I loved that experience.

Connor Regan (28:51):

Then, the last one and current role that I’m in, again, there’s a bit of a story in the transition. This one comes from a more [inaudible 00:29:05]. About a year and a half ago, June 2019, there was a hate and harassment incident on YouTube. A queer journalist was being repeatedly harassed. In my view, YouTube didn’t do enough to take a stance against that.

Connor Regan (29:25):

There’s a lot of complexity here. I am a proud Googler. I think Google really does live up to its mission of trying to … free and open platforms that benefit many people and this was a very hard call. Not at all dissing my employer here. But I did think in this case, we could have done it better.

Connor Regan (29:48):

I was like, well, I can either be frustrated or quit or make a ruckus, or I can just go and join that team and try to fix the things that I think are broken and really prioritize the community that, in my view, was not seen as important as it should have been. In that case, that’s the queer community.

Connor Regan (30:11):

That’s what I’ve done for the last little over a year, working on policy and operations in the monetization world at YouTube. Sorry, that was very long winded, but now you really have the journey.

Mike Raab (30:26):

No, it’s great. I love the stories of why you chose each thing next, the reasoning. But specifically, it must’ve been energizing to have this personal mission that you’re able to then go and influence your employer with so quickly.

Connor Regan (30:44):

Absolutely. I mean, I would encourage everyone to think about, is there something about the role that I might be taking or the role I’m applying for that I know I have a personal investment?

Connor Regan (30:57):

It doesn’t have to be I’m queer and I want to do good things for queer people. That one. But it can also be I really love math. I’m a nerd and I like math so much that I want to do a role that has a ton of quantitative work as part of it. But something that is genuine, where it’s not just like, this will be great for my resume. This is a good brand, or that’s a good title, or the pay rate is awesome. There needs to be at least something there that is that personal motivation.

Connor Regan (31:28):

Because even in that great role, there are going to be days where you’re like, I hate this. This is not fun. I just want to do something different or be on vacation. It’s the personal investment, I think, that that keeps you invested and performing well.

Mike Raab (31:44):

I totally agree that internal motivation of learning or enjoying what you’re doing lasts a lot longer than the external of this will look good on my resume. Wrapping up here, if you had one piece of advice for a young Connor who is in school and was ambitious and wanted to follow in your footsteps, what would that be?

Connor Regan (32:04):

I don’t think this will apply for everyone, but I think for those that it does apply to, I think you’ll know I’m talking to you right away. I think it’s important not to take yourself too seriously.

Connor Regan (32:14):

I was a very serious student. Most people don’t go around asking people, what did you think of me back then? Or that thing. But I think if I asked people, I do think I made a lot of trade-offs in pursuit of all these internships and all these whatever, that made me a bit ruthless in my prioritization. In some ways, I’m really thankful for that. I’ve landed in a place where I’m really happy. I like my job. I like my life. I feel like I have been and will continue to be successful.

Connor Regan (32:57):

But also, maybe I didn’t have to be so committed to a plan. I think I was really serious. That doesn’t mean I didn’t have fun. I miss Northwestern all the time. I loved being a student, being in college in general. It was great. But I don’t know, maybe I would have had even more fun if I were a little bit more flexible with my plan.

Connor Regan (33:24):

That’s not invaluable. That has a lot of meaning. Even meaning that you can turn into these professional types of achievements, too. There’s value in that personal stuff, in that stuff that doesn’t necessarily fit into some formulaic plan. Yeah, it’s all a balancing act.

Mike Raab (33:49):

I completely agree and I think that’s a good place for us to end. Connor, thank you again so much for being with us today.

Connor Regan (33:55):

Thanks a lot for having me.

Mike Raab (33:57):

If there’s one lesson I would take away from Connor, it should be obvious. His prioritization of gaining exposure to a diversity of experiences, ideas, and people has not only armed him with the knowledge of what he enjoys and is interested in, but has also opened up many opportunities for him. These diverse experiences have empowered Connor to be flexible in his career and follow the path that is most interesting and exciting to him, instead of what he refers to as quote-unquote the default. I hope Connor’s story inspires you to seek out diversity in your experiences and never fear trying something new.

Mike Raab (34:31):

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.