BTU #152 - Financial Planning & Entrepreneurship (Aaron Milledge)

"About three years prior to leaving active duty, I started using the same planning process we use in the fighter business - you start with the target and move backwards. You fill in all the gaps - your assets, the threats, contingencies, and limiting factors. After multiple iterations of this planning process, you should start to see some patterns emerge about what your passions are and what you’re equipped to do. .”- Aaron Milledge

Subscribe on: iTunes | Stitcher | Google Play            Enjoy the episode? Review us on iTunes!

Why to Listen | Sponsors | Selected Resources | Transcript & Time Stamps | Comments

Aaron Milledge

is the Co-Founder & Chief Compliance Officer of Targeted Wealth Solutions, an independent Registered Investment Adviser that provides comprehensive wealth management across all stages of their clients’ lives. Aaron started out at Emory University, after which he served as a Fighter Pilot in the U.S. Air Force for over 12 years. After his service in the Air Force, he founded Targeted Wealth Solutions. He holds an MBA from Indiana University's Kelley School of Business.

Why to Listen: 

Many guests on my show in the past have advised those on Active Duty to take care of their finances so that they have the time they need to find their ideal career. Well, today’s guest, as a financial advisor, has made it his profession to help people take control of their finances. He talks about financial advising as a career path, as well as what it has been like to start his own company.

Our Sponsor: 

  • StoryBox - People trust each other more than advertising. StoryBox provides the tools and supports businesses need to take the best things customers say about them, and use them to drive more sales and referrals. StoryBox offers a 10% discount to companies employing veterans of the US Armed Forces.
  • Audible is offering one FREE audio book to Beyond the Uniform listeners. You can claim this offer here, and see a list of books recommended by my guests at

Selected Resources: 

Transcript & Time Stamps: 


Today is Episode #152 with Aaron Milledge. Special thanks to Ben Grisamore for introducing me to Aaron. I really enjoyed this interview. One of the reasons I think you should listen is that in countless interviews I’ve done for the show, veterans have advised that the best thing you can do to prepare for your transition is to start taking some financial responsibility. Most of the people that I’ve talked to have said that it took longer than they anticipated to find their first job. So the more you have saved up, the more freedom you have to wait for that perfect position.


In the first part of this interview, Aaron talks about his career as a financial advisor. He talks about what that’s like as well as about what veterans can do to get a firm foundation in their finances as they’re transitioning out. I think it’s the first time I’ve had this career path on my show so we really dive into what it looks like to be a financial advisor. In the second part of the interview, we talk a lot about entrepreneurship because Aaron started his own financial advising company so we talk about what that’s like.  


If you haven’t had a chance to leave Beyond the Uniform a positive review on iTunes, I would greatly appreciate it. It would mean a lot to me since it really helps us get the word out about the show. So with that, let’s dive in to my interview with Aaron Milledge.


Joining me on this snowy day from Erie, Colorado is Aaron Milledge. Aaron is the co-founder and Chief Compliance Officer of Targeted Wealth Solutions which is an independent registered investment advisor. Aaron started out at Emory University after which he served as a fighter pilot in the US Air Force for 12 years. After leaving the military, he went on to found Targeted Wealth Solutions. He also holds an MBA from Indiana’s Kelley School of Business.


How did you approach your decision to get out of the military?

I went through Emory’s ROTC program during college. That experience played a big role in my decision to leave the military. There were multiple factors which is the case for a lot of people. At that point, I felt like I had achieved what I wanted to in the aviation world so this was an opportunity to try something new.  I was passionate about starting something of my own in the financial services industry. But of course it wasn’t an overnight decision. It was a choice that I spent about three years shaping and refining. I started think about what life after the Air Force would like for me and my family. The trade-offs from a health care perspective were large. I had two kids at the time and my daughter had some special needs that would have been difficult to get covered outside the military. So as such, we took a hard look at our family’s balance sheet and it indicated that we would need to supplement our income if I decided to get out of the military. So that something else ended up being me staying in the Air Force Reserves. That added a little more income and preserved health care and retirement benefits. I would encourage folks that want to get off duty but will need to supplement their income to think about doing something similar.

I’m a standard television advertisement for one weekend a month, two weeks a year. Obviously, to have those benefits of healthcare and those accruing retirement points is great. But you also have access to a part of the military that had previously been closed off. For instance, I’ve now worked in Space Command which I had no previous experience in. So from a personal development aspect, it’s a great opportunity.


It seems like being in the Reserves has provided you with the opportunity to maintain a connection with a community that has meant a lot to you.

Absolutely. You talked in a previous episode about the intangibles that military experience provides you. The security, value of service, and direction. It’s difficult to leave that security and jump right in to the civilian sector. So I think your insight is spot on.


How would you explain what your company Targeted Wealth Solutions does?

We’re an independent registered investment advisor. We’re former combat aviators that help business owners and veterans plan and realize their financial goals. We approach the traditional financial advising industry a little bit differently than a lot of people do. I think that gives us a lot of latitude to work within and get folks set up on a path to financial success.

I’ll give you an example of someone who was a recent client of ours. He is going to be getting out of the military and starting his own business. The majority of advisors I’ve come across in the past have gone through a process of having clients input numbers into a system and the coming back with some sort of result about that person’s financial health. But entrepreneurs have very different financial needs. So what I do is take a look at the resources that that a client has access to and their predicted burn rate. We can then provide advice based on that. So we crafted a series of checkpoints for the client to check in with moving forward.


I really love that idea of checkpoints. I think it’s so helpful to have landmarks that you can check back in with and see how you’re doing.

Yes, when you’re in the middle of it, it can be difficult to rationalize your way out of it. But these checkpoints can be helpful in doing just that. I think it helps folks to make a plan that is backed up by these checkpoints, analysis, and common sense. I think this can add real value to people that may be struggling with uncertainty.


Do you work with just with people in the Denver area or with people remotely as well?

We actually prefer remotely. We started Targeted Wealth with a focus on military folks. So we spent a lot of time building out our tech stack in a way that would allow us not only to reach compliance needs but also allow us to reach our clients remotely. So truth be told, we prefer working with people remotely on their timelines.


In the work you’ve done with veterans, are there misconceptions about finances during the transition?

I think veterans are some of the most engaged and well informed clients. I think there's a misconception that if someone has educated themselves and done well in their career, they don’t need to go to a financial advisor. I think the counterpoint is that engaging with an unbiased financial advisor can be very beneficial.

I think there’s also misunderstandings regarding employee benefits that you’re used to having in the military. So it’s a question veterans face of how they’re going to replace those in civilian employment.


How do you charge clients?

It’s completely based on what they’re looking for. There are typically two pathways. The first is under asset management and financial planning. That’s about creating a plan to keep the train on the tracks from a financial planning perspective. We also have an hourly financial planning session that we offer to clients based on what specific advice they are seeking.


A typical mindset for veterans is wanting to figure everything out for ourselves. What I really appreciate about what you’re saying is how helpful it can be to consult an outside perspective from time to time.

Right and we love the unknown unknowns. To that point, we’ve always been surprised that you have these professionals who are very specialized in a particular area and can provide great value to you. We’ve found some really great opportunities where professional providers can crack the whip for clients and make sure the left hand is talking to the right hand. They can provide expertise that is extremely valuable.


What was the genesis of Targeted Wealth Solutions?

It’s been a long time coming but it has been packed in to more discreet time frames. When I was first flying for the Air Force, you didn’t need an advanced degree to promote so everyone based their life plans around that. Later that changed in that the Air Force said you did need a Master’s degree. That pendulum has now swung back and forth several times. I was at a point where I wanted to go back to school anyway. My dad, who was a career changer and business owner, told me that I might find value in getting an MBA. So I decided to go back to school.

After I finished my MBA, I realized three things - one that I had no desire to work for a huge corporation, two that I really enjoyed the quantitative aspects of finance and three that I had no idea where I wanted to end up or how I should get there. From there I reached out to my network and talked to anyone I could - investment managers, bond traders, and financial advisors. Anyone that had a role in finance that I could possibly be interested in. It worked to build a rough foundation for me. In 2012, three years prior to me leaving active duty, I started using the same planning process we use in the fighter pilot business. You start with the target and move backwards. You fill in all the gaps - your assets, the threats, contingencies, and limiting factors. After multiple iterations of this planning process, you should start to see some patterns emerge about what your passions are and what you’re equipped to do.

I had a bias against financial advisors from the get-go because of bad experiences my parents had. But if my parents, who are business owners, went to a financial planner that offered them a full spectrum solution that was in their best interest, I think they would have felt differently. So, I arrived at this place with some divine intervention. I realized that there was an opportunity in the financial planning industry that was an intersection of my professional and personal interests.


What does your day-to-day look like?

When you interviewed Wes Gray - everything he talked about had some similarity to what I typically do in a day. I’m a big fan of Wes and Alpha Architect so a lot of what he mentioned resonated. The verb that he used - grind - is a tactical word in the fighter pilot business and there’s an interesting parallel because guys like to romanticize this particular tactic and make it something it’s not. So when used in the right ways with well defined objectives - it’s great. But sometimes you can end up on the back foot with not a lot of accomplished. So I mention that because I think many entrepreneurs can get into a “grind” mentality where they feel like they’re getting a lot accomplished but they’re not. This might be more pronounced with veteran startups. But if you don’t have a clearly defined end state, then you’re just “grinding” for the sake of the verb.

With that said, we try to break down our day into modules that we can work within throughout the firm. For a lot of traditional advisory firms, the firm operates in a silo. Each person has his or her book of clients and operates within that. But that is not the way that we do business. I think there’s a great benefit to the client when you get everyone interacting and on the same page.

My day starts pretty early - my kids are early risers. So we get up and play and get ready for school until about 7:30. A lot of that is by design because when I was on active duty, I missed out on a lot of family time so now I’m very deliberate about how I spend my time. After that, I catch up on financial news and handle any fires that have happened since I left work the previous day. That gets me to about 10 in the morning. At that point, we start dividing up our goals for the quarter and start tackling those. We try to come up with a limited number of factors that will allow to start working toward our goals. We spend time throughout the day working with clients, bringing them clarity surrounding whatever financial uncertainty they have. After all that, I have kind of a recap with Brandon and Ben who are two of the other advisors in the firm. It helps us get ready for the next day and is also the time where the ensemble comes together to solve any kind of client issues that have come up so that when we present a client with a proposed solution, it is something that everyone has had input on.


Do you have any thoughts on maintaining work/life balance?

I try to stop around 5 to make sure I have time for my family. Unexpected things pop up sometimes but generally I try to wrap up around 5. Typically the first things I’ll schedule are family events and then work around that. In the civilian capacity, you have the opportunity to create your work/life balance whereas in the military you largely don’t for various reasons. So I make it part of my structure to figure out what the next week and month will look like. The benefit of running a startup is that I have the ability to do this.

I think it’s difficult for people because in the military they are so used to putting the mission first so it’s feels very different to think about putting other priorities first. You do have to make a conscious decision to find that work/life balance. For me, I have fairly rigid start and stop times for my work grind time which is when my kids are at school.


If someone is thinking of becoming a financial planner, what are some signs that they might be a good fit for this profession?

There are so many nuances to the definition of being a financial planner but at the end of the day I think it’s vital that financial planners have the humility and approachability that allow people to come to you and bear their finances to you which can be very personal. If you’re genuine in your desire to help and you have a talent for analyzing this information, it’s a very rewarding career. You can really make an impact in someone’s life by helping them reach their financial goals.

Wes Gray mentioned that with startups, nobody is there telling you what to do. That can be very difficult for some people. As an independent advisor, we have a huge chess board which we operate within that but there’s not necessarily a checklist. So you have to be comfortable with creating your own checklist that is going to guide your operations. So from the startup perspective, if you have a passion and you’re comfortable with grinding toward an objective without anyone telling you how to get there, this could be a good fit for you.


I love that thought of self-knowledge because for some people that ambiguity is extremely motivating while for others it’s terrifying.

And I would throw out there that even if it terrifies you, I think that can provide insight even in a role at an established firm. Many roles are very self-directed. I ran into situations when I was doing informational interviews during my transition where I was at a smaller firm that just didn’t have the capacity to do a large formal training program for veterans. They would tell stories about how they had brought in very accomplished military members in the past that were then paralyzed in the civilian sector without that direction. So these employers were gun shy about hiring transitioning veterans. So if it terrifies you, it’s a good thing because then you can address that within yourself and during interviews.


Do you have any resources that you would recommend?

One of your previous guests mentioned budgeting for personal development and I’m a huge believer in that. I don’t have any specific books or seminars but I think it’s important to develop yourself in ways that are materially different than the military.

On the formal education side of things, I completed an MBA. I also completed some courses with the Charter Financial Analysis program. I took some courses with Breaking Into Wall Street with Financial Modeling. I also took huge advantage of Coursera including Intro to Data Science and Data Visualization. I was able to build up my bucket of personal development this way. Also blogs like Wes Gray’s blog. I also did Stanford’s Machine Learning course. I was happy if it helped me with future employment but I was also just interested in the content.


Do you have any parting advice for military members during their transition?

Starting earlier is better if you’re transitioning or even just exploring. Even if you’re not sure if you want to get out, just exploring what’s on the other side can be a great thought exercise. I recommend looking into the Veterans Mentor Network on LinkedIn as well as American Corporate Partners which I took advantage of and was hugely helpful to me. Specifically for veterans looking to get into finance, I recommend the Veterans Integration Program through Goldman Sachs. And then the internet has disrupted everything so just staying engaged and consuming material relevant to what you want to go into.


Aaron, thank you so much for your time, advice, and willingness to share your story.

Post Show Notes


I really love Aaron’s thoughts on budgeting for personal development. I’m a huge advocate of this. I think the thought of investing in yourself can be extremely valuable throughout your life.


I also thought it was really interesting to hear the perspective of someone that left the military after 12 years of active duty. It’s an interesting time to leave active duty and move into the Reserves.


I loved how he talked about planning ahead and the concept of using modules to focus yourself during the workday. If you enjoyed this episode, please share this with anyone you think would benefit from it. I will be back next week with another interview with a veteran who will chat with us about their civilian career.