EP211: Personalized Wealth Strategies with John Shanley

Defining Investing Success: Goals, Asset Allocation, Diversification, and Consistency with John Shanley, CFP

On The Girl Doc Survival Guide, Christine interviews John Shanley, CFP, Partner and Managing Advisor at Connecticut Wealth Management, who shares how he connected with founders Dennis Horrigan and Kevin Leahy, and sought a fiduciary approach where client and firm interests align. Christine discloses Shanley is her family’s advisor and frames the episode for physicians who want to plan better, referencing Dr. Adam Rubin’s points on compounding. Shanley says successful investing starts with defining personal goals and understanding yourself, then building an integrated plan that includes taxes, estate, charitable intentions, and risk management like disability coverage. He discusses asset allocation (stocks for long-term growth, bonds for stability), diversification as accepting uncertainty, and cautions on private equity due to illiquidity and “too good to be true” promises. He contrasts investing with gambling, emphasizes minimizing downside, staying disciplined through market cycles, starting now even if late, and concludes: “Get organized before you get fancy.”

00:00 Meet John Shanley

00:37 Finding a Fulfilling Career

01:19 Fiduciary Values and Serendipity

02:58 Why Physicians Need a Plan

04:14 Define Investing Success

06:00 Personalized Planning Beyond Rules

07:11 Staying the Course

09:37 Asset Allocation and Diversification

11:47 Private Equity and Lockups

12:44 Asymmetric Risk and Consistency

14:34 Starting Late Still Works

15:31 Money Mindset and Psychology

16:42 Final Takeaways

This content is for educational purposes only and is not intended as personalized investment advice. The information provided does not present a complete picture of every material fact related to the companies, securities, and industries discussed. The information provided will not be updated any time after the date of publication. The owner of The Girl Doc Survival Guide is a client of the firm. Their participation does not constitute an endorsement of our services, and all discussions are focused on business insights rather than personal financial matters.

Founded in 2010, Connecticut Wealth Management, LLC (CTWM) is a registered investment advisor (RIA) that provides holistic financial planning, tax planning, and investment advice for high-net-worth individuals, including business owners, executives, and multigenerational families. Registration with the SEC does not imply a certain level of skill or training and does not imply the endorsement or approval of the qualifications of Connecticut Wealth Management and its representatives.

Transcript

Christine Ko: [00:00:00] Welcome back to The Girl Doc Survival Guide. Today I am very pleased to be with John Shanley. John Shanley, CFP is a Partner and Managing Advisor at Connecticut Wealth Management. He is dedicated to personalized attention and developing individualized wealth plans, proactive solutions, and thoughtful strategies for maximizing efficiency. He implements firm-wide portfolio strategies and innovative technology solutions. He has a Master's of Science in Financial Services and previously taught at Elms College. Welcome to John. 

John Shanley: Christine, thank you for having me. I'm honored to be here, and I'll try my best to live up to all your esteemed guests.

Christine Ko: Can you start with a personal anecdote? 

John Shanley: Yeah, I'd love to. Christine, I've heard you say this a lot before, the importance of finding something you love and that provides a deep sense of fulfillment. When I was growing up, I never wanted to be a financial advisor. I really stumbled into this career. I was very lucky where early on, I just fell in love with it, especially the technical aspects: market history investing principles, [00:01:00] taxes, estate insurance, all of that stuff. It just scratched an itch that nothing really has before or since done for me. I was lucky where I found a career I was very passionate about, but I was also able to find an environment that let that passion grow. Without that environment, I don't know if the passion would've been enough. So that gives you a little bit of a sense of my journey to where I am today. 

When I first started my career, I worked for a really large corporation, and they were wonderful. But there were moments in that journey where I felt like client interests and firm interests sometimes collided, like you were serving two masters. So as my career went along, I was lucky enough to run into Dennis Horrigan and Kevin Leahy, the founders of Connecticut Wealth Management. Right from the get go, they were just speaking exactly the same type of language that resonated with me, like we were rowing in the same direction; our interests were aligned.

Christine Ko: How did you meet Kevin and Dennis? 

John Shanley: Probably a little bit of happenstance. I knew what I wanted out of my career, so I just reached out and tried to connect with as many people as I could. The [00:02:00] financial advising community, especially a fiduciary approach to financial planning, it's actually a relatively small community. I reached out to Dennis 'cause he was actually part of a local organization of financial planners. I had coffee with Dennis, and we instantly connected. He really did speak all the right words, very genuine. He's a very genuine guy. When I found the right group, I just did everything I could to make sure that I was working with them. 

Christine Ko: That's nice. It's funny, I think, how much sometimes, maybe unfortunately, life is by chance. It's serendipity. It seems somewhat random, like lucky that you reached out to him. Lucky to be able to reach out to him and then have coffee. 

John Shanley: Christine, I couldn't agree more, and I think it's both unfortunate, but also maybe the beauty of life, in terms of how just uncertain it all is. It sometimes reminds us all to live in the moment. My job is to plan for the future, but planning for the future is also making sure you do live in the present, 'cause we don't know what tomorrow is gonna bring in all the various sense of the words. The good, the bad.

Christine Ko: Yeah. I should say this, in full disclosure, John [00:03:00] is my family's financial advisor. Kevin Leahy was in the past. Earl Glusac, one of my colleagues, was the one who early on in my career introduced Kevin.

Adam Rubin, who I spoke to a couple weeks ago, really wished that he had thought about investing earlier on in his career, which I was lucky to have had Earl talk to me about early on. In case there are other relatively young physicians or even older ones who don't know yet how to be planning for the future, I thought it would be good to have you come on. So that's how this happened. Full disclosure, john and I have had a lot of conversations about money, and John knows how little, actually, I know about investing because I just leave it to him. 

John Shanley: Not at all. I should say, too, I listened to the podcast you have with Dr. Rubin, and if anybody hasn't listened, they should, because his insights to compound interest and time, he said them better than I ever could. I'd highly recommend people listen [00:04:00] to that. It was very well done. 

Christine Ko: Yes. Adam said that he really wishes he had started investing earlier because of that power of compounding over time. That's what Adam wished he had known earlier. What do you think everyone should know about investing successfully? 

John Shanley: It's a wonderful question, and I would first start by saying you wanna understand, How do you define success? The way you define success, I'm saying the broad you, and how I define success may be very different things. That can be very applicable with something like investing. Because if you turn on the news today, and let's say you watch Bloomberg News, which I love, their definition of success is wildly different than my definition of success, right? I define success by how can I help my family reach its long-term objectives, the short-term objectives. If you turn on Bloomberg, it's more about what's gonna happen today or what's gonna happen tomorrow.

So the first thing I would say is the way you can be a successful investor is understand, what does success look like for you? Define it.

The other thing I would share is that there was a book I read [00:05:00] years ago, Christine, it's called The Money Game. It's a book from the 1960s, a famous investing book. In that book, the author said, If you don't know who you are, the markets are an expensive place to find out. When I read that years ago, it hit me, and it still hits me to this day because I think for most investors, they look at the idea of investing their hard-earned money, and it can feel sometimes scary. Markets are complex, there's constantly different news flow. You don't know whose advice to trust. So the way we think about investing successfully is by really knowing, What are your goals for today? What are your goals for tomorrow? What are the things that keep you up at night? What are your passions? And then all the other technical stuff. What does your tax profile look like? What is my estate? My charitable intentions? If we can define what a successful life looks like for you, it's a lot easier then to define what is a successful investment life. You're the person driving your financial picture. The investments are just a spoke in the wheel. It's just a part. And if you don't have the full picture, investing successfully, in our eyes, is very hard to do. 

Christine Ko: That makes sense because I'm sure everyone does have different goals.

John Shanley: It's a common thing in our [00:06:00] industry, rules of thumb. Rules of thumb can be great, but a common rule of thumb is, When you're investing, you should get more conservative as you get older, right? That's a very common rule of thumb. But I would say that rule of thumb is not very useful. We have clients who are in their nineties that are very aggressively invested because they're not investing for themselves, they're investing for future generations. It could also be completely flipped. If we have a young 40-year-old investor, they may invest conservatively 'cause they just cannot ride through the ups and downs of what markets might give them. So investing done successfully really is personalized to who you are. There's some principles that will apply to all of us, but the way to be successful as an investor is to know yourself and to craft a plan based on that.

You need to make sure that all of the aspects of your financial life are intertwined in a smart way. Kevin Leahy, the CEO of our company: he's a financial planner at heart. He said something along the lines of it doesn't matter how great of investors we are if one of our clients became disabled and could no longer work and they didn't have the right type of disability coverage, those investment successes meant nothing. That would be a catastrophic risk for somebody's financial [00:07:00] plan. It all works together. If you have all those aspects tacked together, or you work with somebody that can tack them together for you, then it's just about timeframe and consistency.

Christine Ko: Yeah. I have to say, I'm a little embarrassed to confess this right now, very irresponsible. I do feel this about myself in not paying attention to financial stuff. But that's why I leave it in your hands. And very happy to do that 'cause I don't like thinking about this stuff, unlike you who finds great joy thinking about it. And I will say I had forgotten, but early on, Kevin set us up with disability, made sure that we had it, that he agreed with what we had, and we met with people who went over it.

I don't know if I ever told you this, but actually early on, before we were with you guys, we actually lost a lot of money, what felt like a huge sum to me at the time. We started working with you guys, and you guys pointed out that maybe that wasn't the best investment. So we pulled out of that and lost a fair amount of money, [00:08:00] but it was the right thing to do, I think. One of the reasons I don't like to think about this kind of financial stuff is because I think it's very complicated. Even though there are some very accessible concepts like compounding, asset allocation, diversification; to implement them, I think, takes skill but also time.

John Shanley: Exactly. Time is our most valuable resource. I would actually model you and Peter as wonderful investors. Your intentionality. You could spend your time looking in investments and following taxes and all that type of stuff. Or you could spend time with the things that matter most to you in your life. Family, friends, vocation, all of those types of things. You're intentional about that. And I think that's actually beautiful in so many different ways. You have your things you're passionate about, and you excel at, and we're lucky enough where we have our passions and things that we would excel at. So, I think you're being maybe a little hard on yourself. You're, you've done very well, Christine, in your money journey. 

Christine Ko: I think that the one thing [00:09:00] that I've done right that goes along with our conversation is that we've been consistent over a good amount of time now, so then the compounding comes into effect.

John Shanley: If I could just even add to that, Christine. You've invested now for a long period of time. In that period of time, you've seen some really poor market events. You've lived through some lows, and you've lived through some highs. And, throughout that journey you both stayed really strong investors. You didn't sell out at the wrong time or try to chase the next hot investment. And again, that doesn't always sound all that exciting, but that is where the success lies, in making sure that you're able to ride through those ups and downs and stick to your plan.

Christine Ko: Having talked to Adam and hearing him talk about compounding, at the same time I had listened to this podcast, Diary of a CEO, DOAC, and he had talked to Tony Robbins, a highly successful business person. One of the questions to him was, What are your tips for investing successfully? He didn't talk about what someone's goals are. I think the [00:10:00] goal was make as much money as possible. 

John Shanley: Yes. Absolutely. 

Christine Ko: Maybe that's a lot of people's idea of what investing successfully is. Anyway, he talked about asset allocation, asymmetrical risk reward, diversification, and needing private equity to do that. I wanted your thoughts on it.

John Shanley: Yeah, there's a lot in there. Many people have heard of this idea of asset allocation. At the highest level, asset allocation is just the mix of stocks and bonds you have in an account. The way I tend to think of it is, we buy stocks so you can eat well; you buy bonds so you can sleep well. Stocks are gonna be what drive strong returns over the long term. The short term price of that is you're gonna have wild up and downs. Bonds are gonna be much more stable and they provide that ballast to the portfolio. That distinction between stocks and bonds, it sounds so simple, but we would argue that's the decision we need to get right, because you could create the nicest investment portfolio, but if you cannot stick with that asset allocation through the goods and the bads, all of it has gone to waste. [00:11:00] So you need to find a strategy that is going to be able to help you meet your financial goals, that you can stick with. That's what asset allocation done right is.

The next aspect of that, you define your asset allocation building a diversified portfolio. To me, diversification is just admitting to the truth, that the future is uncertain. Today, it's ever more uncertain. Things change constantly. There's a never ending news cycle. So instead of trying to guess what is the next hot investment or the best place to be, diversify. When you make investment choices, make sure that you're not just trying to swing for home runs because you don't wanna strike out. You do not wanna derail your financial plan by making a large investment mistake. So on those two fronts, we do believe that you need to correct the right asset allocation, and you need to build a diversified portfolio.

Now private equity, which I know Tony Robbins has talked a lot about recently. Private equity can be a wonderful compliment to a portfolio. Private equity is public equities, which most of us invest in. It's just they happen to not have a public marketplace where you can buy or trade. They can very well [00:12:00] be a compliment to a portfolio. The one caveat I would say is that you wanna always approach these things with caution, right? Whenever you invest in private investments, you cannot turn around for the most part and change your mind tomorrow. They're gonna require you to lock up your funds for a long period of time. For many investors, that makes perfect sense. If your financial plan shows that you can tie up some portion of your money, that can work great into your portfolio.

But I can't underscore enough that if something is too good to be true, it is. If it sounds too good to be true, always proceed with caution. Make sure you have a full understanding of the types of investments you're getting into, the risks, the rewards. That I think is just incredibly important before you jump into something like private equity.

Christine Ko: Okay. Yeah. And asymmetrical risk reward? 

John Shanley: Yeah. Really good concept. A lot of times when I introduce myself to people as a financial advisor, they say that investing feels like gambling in the sense that you just don't know what your money's gonna do, and you're just gonna lose it all. But I would argue that successful investing is anathema to [00:13:00] gambling, right? When you gamble, the odds are against you. You are most likely going to lose money when you gamble. The odds are against you. When you invest, the odds are in your favor. By being an investor, you are more often than not going to have long term returns. What asymmetric investing would look at is that you wanna try to make sure you're minimizing your downsides. You wanna minimize the chances of striking out and derailing your financial plan. Don't try to swing for the fences and look for that, one in a million type of lottery ticket. Instead, build a diversified portfolio, and that's going to give you the best chances of achieving your goals long term. So I could wrap up that whole area in one saying: Investing isn't about being brilliant; it's about being consistent.

Christine Ko: Meaning, consistently investing, putting money away. 

John Shanley: Spot on, consistent in your strategy. Believing in it even when markets don't necessarily do what we wanna do. Consistent in terms of staying invested, consistent in terms of continuing to save for the future.

Back to the conversation you had with Dr. Rubin, that to me is the beauty of compounding done well, when you give yourself a long timeframe [00:14:00] and you don't mess with it too much. Compounding is just almost like magic. You let things work in a disciplined manner and over long periods of time, it's gonna tend to produce really impressive results. The most important thing you can do is save for the future. Early on, sometimes you won't feel like the investments are doing all that much for you. But then time goes by, and all of a sudden your investments are doing so much of the lifting. It's almost like a flip switch where all of a sudden now compounding is doing so much of the work for you. A lot of that early work will help make the long-term savings.

Christine Ko: What do you do, though, if you hadn't started to invest, and you start later in life?

John Shanley: Yeah. I'm so glad you asked that, Christine, 'cause I do think sometimes when we talk about compounding, if you don't start early, it seems Is it all over, what can I do? But compounding can work no matter your timeframe. It just obviously works better when you have a longer period of time. But if somebody gets started later, I think what they need to just be mindful of is there needs to be intentionality around savings, intentionality around goals. So I think very much it's gonna be similar to people that started [00:15:00] earlier. It's just some of the math changes, and I think maybe there are gonna be opportunities to try to expedite some of your savings goals or reimagining some of your long-term goals. Definitely the game is not done if you don't start early. I know that many times when I speak to doctors, they feel like they're not getting started, or they're getting started much later than their peers. But there's so much working for doctors, and there's so much opportunity. So the best advice I could give is if you haven't started, start now, and you'll be happy in the future.

Christine Ko: When you mentioned earlier that a lot of people think that investing is like gambling. My mom really just thinks that. So I think I have that kind of thought in my head that, when we've lost money at different times 'cause of the market, not because of your guys' efforts, but just the market is poor. I've always been like, I didn't really think the money was there anyway.

John Shanley: Absolutely. Money is such a personal thing. We all have different experiences with money. We have different histories with money. The way we interact with money is different from person to person. So while there are definitely some broad truths about how you'd be successful, everybody's journey is [00:16:00] gonna be a little bit different because what they expect from money, how they interact with it, is gonna be vastly different. If you showed me somebody with the exact same financial resources, their financial plan could look mightily different just because what they expect from their money is gonna be different. So there's definitely a psychology behind money that goes very deep. And again, it's one of these things where, you know, I sometimes pinch myself where I'm like, I'm so lucky because not only are the technical aspects of this job so interesting, but then the personal side, you just get to experience life. Money is such a huge part of life. You get to experience life with clients. And again, I just count my blessings and however it came about.

Christine Ko: Yeah. I'm glad that we have you, that we know you. 

John Shanley: Thank you. 

Christine Ko: Do you have any final thoughts?

John Shanley: Go back and listen to the podcast with Dr. Rubin. That'd be my first one. That was wonderfully done. But if I only had one final thought, we're approaching tax time, so it's on top of my head. Get organized before you get fancy.

Christine Ko: Awesome. Thank you John. Thank you so much for your time. 

John Shanley: Thank you so much.