BTU #149: Marines to Finance & COO @ Alpha Architect (Patrick Cleary)

"Sometimes veterans looking into getting into finance or operations are apprehensive. They think, ‘Oh I don’t know finance.’ But operational readiness, readiness checklists, training teams, supervising - these are all things that are going to be transferable around the world. And quite frankly, often times, civilians are not exposed to these things as much as veterans are. So there’s certainly an opportunity to get involved in a field like this, you just have to understand that you do have transferable skills..”- Patrick Cleary

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Patrick Cleary

is the Chief Operations Officer at Alpha Architect . He started out at the University of Pennsylvania, after which he served as a Platoon Commander in the U.S. Marine Corps for four years. After his active duty service, he received his MBA from Harvard Business School, worked as a Project Leader at the Boston Consulting Group, and worked at the global business service provider, Algeco Scotsman Group.

Why to Listen: 

This is a must-listen-to episode. Patrick covers so much ground in this interview - we talk about choosing a team that is lean and mean; we talk about his experience not being sure of what to do for 5-6 years, wandering from business school to consulting to ultimately finding a place he passionately calls home; we talk about work and life balance and how to think about this as an entrepreneur; and we talk about finance and entrepreneurship. There is so much great advice in this interview!

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Selected Resources: 

Transcript & Time Stamps: 


Today is Episode #149 with Patrick Cleary. I hope all of you have had the chance to listen to Episode #134 with Wes Gray who told the inspiring story of how he went from the Marine Corps to starting Alpha Architect, a company that I came across in the Wall Street Journal in an article talking about the company as one of the fast growing and impressive investment funds in the universe. My guest today was introduced to me by Wes. Patrick works at Alpha Architect as well and I think this is a really inspiring interview.


We talk about so many things - we talk about choosing a team that is lean and mean. We talk about Patrick’s journey about not being sure of what he wanted to do for about five years. He went from business school to consulting and ultimately found a place he calls home. We also talk about work/life balance - this is probably the best discussion of work/life balance I’ve had on the show. We talk about finance and entrepreneurship. Regardless of your interests, this interview is a must listen.


Stick around after the interview as I’m going to be trying something completely new.  I’m going to do a debrief and talk about what stuck out to me from the interview. I would also invite you to share what you enjoyed about the interview in the show notes so we can get a discussion going. I know we can extract even more value from this interview by sharing our takeaways. And with that, let’s dive into my interview with Patrick.


Joining me today from Philadelphia, PA is Patrick Cleary, the COO of Alpha Architect. Patrick started out at the University of Pennsylvania after which he served as a Platoon Commander in the Marine Corps. After leaving the military, Patrick earned an MBA from Harvard Business School. He then worked as a project leader for the Boston Consulting Group and worked at the global service provider Algeco Scotsman.


How would you explain what it’s like to be a Chief Operations Officer and Chief Compliance Officer of a financial services firm?

It’s really all about attention to detail. You’re basically like a lieutenant that is responsible for everything and aything that the unit does in terms of day-to-day operations and in compliance matters. And I’ll give you an example - we’re in a highly regulated industry and there’s all sorts of rules and regulations. I’m responsible for making sure we do all of that stuff. And we have an infrastructure built up to make sure we’re filling out all the necessary forms and submitting the right documents. That’s kind of at the granular level - it’s kind of like an inspection level. And then there’s a more macro level aspect which is making sure we’re ready for the operations of the future.


Have you always been so detail oriented?

No, actually. The reason I joined Alpha Architect was because of the team. I wanted to be in a small team of veteran entrepreneurs. I wanted to be part of a lean and mean entrepreneurial venture. So I enjoy the job but I’ve found what is much more important has been finding the right team.


How would you describe Alpha Architect?

It’s basically a billion dollar asset manager in a garage. Imagine a very lean start-up environment - we’re all cheap bastards and drive crappy cars. We have a yucky office and bad Folgers coffee. We’re a no frills operations but we work towards being transparent and lean, values that we learned in the Marine Corps. We’re an asset manager, we manage money on behalf of investors.


What does a typical day look like for you?

One of the benefits of entrepreneurship is that there really isn’t a set schedule. If you’re thinking about entrepreneurship, you will work your tail off but there’s not necessarily a set schedule. During the workday you’re constantly firefighting so what I like to do in the evening is outline my top three priorities for the next day. I work very closely with various forms of legal council. In that role, I’m cycling back and forth with documents between those different groups. There’s also an inspection and compliance check aspect to make sure we’re making trades and contacting clients in an appropriate manner.

This takes until about noon. During lunch, I always try and go out with a coworker. I don’t pack a lunch because I like to use that time to build relationships. In the afternoon, I’m usually focusing on big blue arrow initiatives. For example, the FCC regulates us and comes out with guidance about what firms are going to be inspected on. Typically the FCC will inspect every firm in the industry about once every three years. So I take that guidance and figure out ways that our program can be improved. I re-write our processes and manuals to make sure we’re in compliance. That’s typically an “average day” for me but that can always change.


I love that description and it’s interesting for me because coming from submarines, I remember going through checklists and not thinking they would ever be applicable again. And yet you are describing a similar process that goes on in the civilian sector.

Absolutely, and veterans looking at getting into finance or operations are sometimes apprehensive. They think, ‘Oh I don’t know finance or cybersecurity.’ But operational readiness, readiness checklists, training team, supervising - these are things that are going to be transferable around the world. And quite frankly, often times, civilians are not exposed to these things as much as veterans are. So there’s certainly an opportunity to get involved in a field like this, you just have to understand that you do have transferable skills.


What time do you leave the office and do you find yourself working after leaving the office?

Yeah, I’m kind of a workaholic. I don’t have any hobbies, I’m kind of a loser to be honest. Usually around 5 o’clock I find myself needing to step away from my computer. My wife lives in DC so I spend Monday through Thursday here and then work remotely on Fridays. So on days when I’m away from the family, I usually head to the Crossfit gym after work and then try to work for another hour or two. I’ll wrap up around 9:30 or 10. Then on Fridays, since I’m with the family, I try to make it a lighter day and leave work around 3 or 4.

Like I said earlier, the beauty of working for an entrepreneurial firm is that there is no set schedule. Obviously you do have to be online when the markets are open but as long as your work is getting done, you can shift your schedule. I love that.


That’s great that you are able to work harder Monday through Thursday when you’re away from your family and then have a lighter schedule and be present with them when you’re home.

Yes and I will say that the main driver for the geographical separation between myself and my family is the team I chose to work with. For a service member looking to transition, you have to be aware of what a team values. If you’re looking at a position and you would be the only one on the team with kids and everyone else works six to midnight, try to get additional data points before you accept that position to make sure you are able to maintain work/life balance. Because every firm will tell you, ‘Of course we’re family friendly, of course you can set your own hours.’ Thankfully at Alpha Architect, the team values family and downtime.


If someone is looking to find more of a work/life balance in their civilian career, how can they make sure they’re addressing those questions during the interview process?

There’s a lot of ways you can go about it. I try to connect with people that are already in that company and talk to them about it. Also, during the interview, ask smart questions of the interviewer. Be transparent and just ask direct questions. People will usually give you a direct answer. Also don’t be afraid to reach out to veterans. Nine times out of a ten, another veteran isn’t going to turn down a five or ten minute phone call with you. Don't just limit your search to only the company you’re interested in but others as well.


Do you have any advice about finding work/life balance?

It took me five years to find the answer to that question. There’s things you can do like setting clear boundaries and having clear communication. But I think the key to work/life balance is that it all goes back to the team. If you have a good Platoon Commander, it’s going to be a much more enjoyable experience. It’s also absolutely essential that you’re interested in the job. I can’t tell you how many veterans I met at HBS that would work hard to get amazing job offers but they weren’t excited at all about the job. Don’t shortchange yourself. Have tactical patience to wait for a job you’re excited about. I think as veterans we’re used to just sucking it up and getting through it. But that’s hard to do for 3, 5, 10 years. So really have that tactical patience that allows you to find a job you’re excited about. I’ve never had a conversation with my boss Wes about work/life balance and that’s how I know I have good work/life balance.

And another key to work/life balance that nobody talks about in business school is to maintain a living standard that allows you to have that tactical patience to wait for the right position. If you go to business school and rack up a bunch of debt and then buy a huge house as soon as you get your signing bonus, it’s difficult to have that flexibility. You’re chaining yourself into a lifestyle that isn’t going to allow you to have that tactical patience. I can’t tell you how many peers I saw at Harvard make this mistake. They want work/life balance but their cash burn is $15,000 a month. If you’re in the military, you’ve a great life on not that high of a salary. So think about that when you take on a lot of living expenses.


You went directly to business school after active duty. What advice would you give to someone that wants to get into finance?

The GI Bill opens so many doors. Everything I learned at HBS, I could have learned with a library card and a couple hours a week. I got a great education but the concepts themselves were not revolutionary. The advantage of a school like that is that you gain access to an exceptional network. And for me, it was the same with undergrad. I know Wes Gray from our undergraduate years at the University of Pennsylvania.

So the benefit of Penn wasn’t my class in finance - I got a C+ in my finance class. The benefit was that I met people like Wes there. So if you’re interested in business school, consider the school’s network. If you can get into a Top 5 school, I would say definitely go for it. But for a 50-100 ranked school, it might not be such a good idea. I’d also say look at different business schools and understand what differentiates them. For example, some schools might be great at placing veterans in real estate finance. So do the research to know what that school specializes in. Finally, I’d say look at what successful people are doing three or four promotions down the road. I was at Boston Consulting Group and learned a ton there. On a lot of the projects that I worked on, I noticed that people in the C-suite weren’t those that went to fancy schools. They might have gone to Penn State, gotten an accounting degree and dedicated their career to getting really good at accounting. So I would say don’t put so much faith in the school. The school can connect you to a great network but I really think it comes down to grit. The people that have the grit and are enjoying the work, those are the ones that are going to succeed. The school or degree doesn’t end up mattering so much. Also look closely at the degree. For example, do you really need an MBA or could a CFA help you get to the place you want to go. That could save you tens of thousands of dollars.


What lead you to consulting?

You know that example I gave of the MBA student that was miserable and not excited about their future position? That was me. First off, consulting is a great place to go if you want to learn. I chose consulting because I didn't’ know what the heck I wanted to do. What’s appealing about consulting is that you’re learning very quickly. For me that was a good next step but I knew it was going to be demanding and that work/life balance is tough. Once I had gotten that core skill set, I knew it was time to go. I was at BCG in total for almost four years.


How did the opportunity at Algecocome about?

I knew I wanted to leave consulting. Like a lot of veteran friends of mine, I wanted to do a couple years in consulting and then leave. But I still didn’t know what I wanted to do. BCG has a great program where for three months, they'll give you your full pay and you can just take the time to figure out what you want to do. A friend of mine at Algeco said ‘Hey join this strategy group here. We’re doing a lot of interesting things.’ That was a natural fit for a lot of consultants who go from consulting to an internal consulting group. So to be honest, I took the easy way out. The job sounded good and the pay was good. But when I took a step back, I knew I wasn’t really passionate about it. I didn’t exercise tactical patience to wait for a position that I was really passionate about. I was only at Algeco for about six or seven months. Then when Wes called and I learned more about Alpha Architect, I knew that was what I really wanted to do.


Is there any way you could have shortcut the learning process as far as finally figuring out what you wanted to do?

You’re never going to know an oven is hot until you put your finger on the stove and you learn your lesson. Trial and error is definitely part of the process. I’ve learned more at Alpha Architect than I did in four years at BCG. The only place I’ve learned more was in the Marine Corps. Entrepreneurship is such an amazing educational tool because it puts what you’re good at and what you’re not good at five inches in front of your face. It’s a very dynamic ecosystem that I think is well suited for veterans. I would advise people to try something that is a little risky and a little outside your comfort zone. Huge corporations or consulting firms offer a bit of a safety net. But in an entrepreneurial setting, that's not there. So your learning is really accelerated.


Can you think of a time when you faced a setback in your civilian career and what you learned from that?

There’s a great book that I would encourage everyone to read. Extreme Ownership by Jocko Willink.It talks about how it’s not important who messed up but rather figuring out how to get better. Early in my time at Alpha Architect, I got here and I was really excited about working here. I planned on applying a Marine Corps structure to our processes and get everything squared away. But I didn’t take into account the civilians that worked with me that might find a Marine Officer revamping the way they do business as somewhat abrasive. I didn’t recognize this in my leadership style. We didn’t have any glaring failures but I was talking to Wes about 18 months in about how I was having difficulty getting traction with the team. And I realized that I needed to adapt my leadership style to be a better fit for the team.

When you’re a veteran being transplanted into a civilian job, one of the best things you can do is demonstrate ownership. Take on challenges that you may not consider your turf. We were trying to do compliance checklists and they were not getting done properly. So I decided to walk other people through how to do the compliance checklists. Not in an abrasive way but in a guiding way. For me this was a revelation. It was a good wakeup call to me that I could improve my leadership to better fit the situation.

And I’ll give you one more small example. I’m a neat freak and I would ask guys in a nice way to take out their wastebaskets. But it was like pulling teeth telling grown adults to take their garbage out. I thought about it and then I sent an email to the team. I talked about I had worked for a Battalion Commander in Iraq who was very meticulous about keeping our building clean and neat. I got frustrated by it and didn’t understand why it mattered. But later I realized that the small victories and small wins had huge effects. The Marines at that unit took pride in their spaces. So I wrote this marathon email on why I was so inspired. I got a great response from from that email. It turned about to be really effective when I was able to share my perspective.


Are there any other resources that you would recommend?

I recommend the books We Were Soldiers Once...And Young by Harold G. Moore and About Face by Colonel Hackworth.

Read books about people that were challenged by difficult leadership situations. I can’t tell you how inspiring it is to read about people that when faced with a difficult situation, are able to change their actions in a way that shifts things. These books that talk about doing great things in times of adversity are always good to read about.

If you change your mindset from how can you help yourself succeed to how am I going to help this team and company succeed, you’ll be much better received by your team and it will put you in the mindset of helping those around you succeed. It makes for a better work environment all around.


Do you have anything else you’d like to share with our listeners?

One thing we touched on is that your network is bigger than business school. My best professional friend and business partner, Wes Gray, is someone I was drinking beers with in college. I still take time to invest in the relationships I made in the Marine Corps. Don’t let your relationships erode. It’s extremely satisfying to stay in touch with these people. Also if you want to be mentored on something, you want there to be someone you can reach out to and talk to. I think a lot of people in the military tend to focus on developing tactical professional skills. But I think that’s somewhat short sighted. I make a point to try and go out to lunch with someone here everyday because I want to hear what’s going on and gain insight. So make it a professional point to spend an hour a week to cultivate your professional network.


This has been exceptional. I’ve been inspired by what you’ve said and I know listeners will be too.

Post-Show Notes


Ok so was I right or was I right? I just found that to be an incredibly motivating interview. I think Patrick has a great perspective and does a great job of articulating a lot of things that will be helpful to you. Here are the things that stuck out to me. First of all, I love the thought of writing down 3-5 priorities in the evening for the next day. Cal Newport lays out a great system in his book Deep Work of looking at your calendar and clearing out your inbox at the end of the day. This gives your mind permission to unplug after the workday.


I loved the thought about going to lunch with someone from the office each day. Patrick is so open not only to mentoring other people but also to being mentored himself. He uses that meal to get conversations going and to really learn and grow.


I think Patrick lays out a great process for figuring out if a role is a good fit for you and asking smart questions during an interview to learn more about work/life balance at the company. Work/life in balance was one of my favorite parts of this conversation. I like that he says that it all goes back to finding the right team. He talks about having tactical patience and waiting for the right job. He talks about having the financial ability to allow yourself to wait for the right position.


I thought Patrick had a lot to add to the conversation about business school. I like that he mentioned that he could have learned all this with a library card but that it’s all about the network. I love that he puts it in perspective, too. He talked about how it all comes down to grift and picking the right tool for the job that you want to do.


I love that Patrick said that consulting is a great place to go if you want to learn and aren’t quite sure what you want to do. I agree that consulting is a great place to go that will give you that time to think more about what you want to do while learning a great deal about many different industries. I also like that Patrick mentioned that he’s learned more in two years at Alpha Architect than in four years at BCG. This shows what a great educational tool entrepreneurship can be. He described entrepreneurship as an ecosystem veterans can thrive in.


I really respected how Patrick described failure. He talked about adapting your leadership style to fit particular situations and taking on challenges outside your comfort zone. He also discusses how your network is bigger than your school and about how important it is to stay in touch with people and keep your network alive.


I’d love to hear what you thought of this episode. Please leave any comments you have about this episode below. I would love to get a conversation going among different members of our community.


Finally, if you haven’t had a chance to review us on iTunes, please do so! Not only does it make my grandmother think I’m doing sometime worthwhile with my life but much more importantly, it helps us get the great information provided by men and women interviewed on this program to as many veterans as possible.