Millionaire Interview 296, Part 2

Here’s our latest interview with a millionaire as we seek to learn from those who have grown their wealth to high heights.

If you’d like to be considered for an interview, drop me a note and we can chat about specifics.

This interview took place in October.

My questions are in bold italics and their responses follow in black.

This is part two of a long interview. In case you missed the first part, you can find it here: Millionaire Interview 296.

Let’s get started…

INVEST

What is your investment philosophy/plan?

I would describe myself as “cautiously aggressive”.

I am cautious in that I have primarily invested in index funds, with occasional positions in a few individual equities that I knew well. I am aggressive in that I have always been heavily (completely?) indexed towards equities, and even within equities I overweight small cap/mid cap knowing that they have more volatility.

I have done that primarily because my horizon was long enough that I felt I could weather ups and downs and stay the course in exchange for the traditionally higher returns.

I am also a relatively calm investor. When 9/11 happened, I bought everything I could the day the markets re-opened. During the financial crisis of ‘08-’09, I again bought whatever I could. In 2020 as Covid intensified, I poured money into the market as it dropped.

I would not say that I am a market timer, just someone who can usually spot emotional selling. Keeping a long term horizon is helpful. I actually somewhat wonder what I will do when my horizon isn’t, in fact, so long term.

I also try to keep history in the back of my brain as I contextualize decisions. A great example would be current mortgage rates and the cost of debt financing. It’s so ridiculously cheap right now that I refinanced both of my properties and even took some money out at the same time.

While I very much yearn to be debt free (mainly for emotional & cashflow reasons), it’s hard for me to get my head around paying down a 3% (or lower) 30 year fixed note vs other alternatives. In fact, I went the other way and even opened up a line of credit I can use against my life insurance policies in the event I am able to find some undervalued assets somewhere (real estate or otherwise).

One of the common questions/debates on this blog is the use of financial advisors. I have had a financial advisor for the past 20 years. Initially, it wasn’t worth it.

I switched about 15 years ago, and with the new one I have had ups and downs, but mostly ups. We have had several debates over the years about fees, but it came to a head a few years ago as low-cost robo-investing became readily available. At the time, my investment portfolio was reaching close to $1M and fees were over 1%. After several back and forth’s, he begrudgingly reduced his fee when faced with an ultimatum and we got to a healthier place which felt more equitable.

However, the process demonstrated to me that you have to find a healthier way to align, and unfortunately you need to advocate for yourself. I probably let my frustration grow for too long, and should have reached a framework agreement earlier. He has since gone out of his way to provide value added services that have been helpful to me and partially justify his fees.

I also realized that I was going to need to have this conversation every time I hit a milestone, and that I didn’t want to have to monitor that. As a result, I opened up a Vanguard account and started diverting more of my after-tax investing that direction. My investment stream with my advisor continues, but is frozen at current levels. Most incremental investment funds are going towards the lower cost option at Vanguard which I expect will get similar returns but with lower fees. I kind of like the blended approach.

What has been your best investment?

I would have to say education.

I was so unbelievably lucky to graduate with a bachelors degree and no debt as a result of my parent’s generosity. They were both the first people in their families to go to college, and they worked really hard carrying multiple jobs to pay for their schooling. However, their agreement with us was always “four years on us, anything else is on you”. What a gift!

Graduate school was 100% on my own and I went into debt for that degree. I tested out of a year of grad school by pursuing the advice of a friend (eliminating 101 type classes), which saved me a lot of money. I completed my graduate studies in 16 months, and pushed the limits of what was allowed. That speed saved me a bundle, and accelerated my time to payback.

That educational investment doubled my starting salary. It also helped me create a network, and exposed me to a community that I count amongst my closest friends to this day. It allowed me to have a trustworthy roommate who was willing to pay rent so that I could buy my first house.

I had to cajole my way into a down payment, budget the heck out of how I could make it work, and then execute while I was traveling all over the place. That home increased 65% in value over a 3 year period, which on a cash on cash basis was almost a 2,000% return as I put very little down with an FHA loan. Selling that property wiped away my student loan debt and my car loan. I finally made it to a positive net worth (barely)!!!

Amazing that I didn’t need taxpayers to write down my student debt, isn’t it?

What has been your worst investment?

There are probably too many to count.

It could be the house I purchased during my first marriage that we sold for a major loss after the market corrected right before our divorce. I think I am one of those people that probably chooses to not focus on “the worst’s” and stack rank them. I have made money and lost money in real estate. Overall, I am probably slightly ahead. I have also been lucky to avoid really bad selloffs for the most part.

My worst investments have probably been “non-investments” where I was unable to act on opportunities I could see due to limited cash flow.

I also have had moments where I have caught myself thinking like a consumer too much. It took me a long time to really get into a mindset of questioning purchases and debating them as investments as opposed to expenses.

What’s been your overall return?

Hard to say.

Given my investment positions, I track relatively closely to the market. I may augment my returns a bit by buying on the dips and buying historically riskier asset classes (small cap), but over a long enough horizon my suspicion is that I regress close to the indices.

Recent market returns make us all look like investing rockstars, but I would estimate long term in the 9-11% range. Recent years have been higher.

How often do you monitor/review your portfolio?

Pretty much daily.

Even when the market was tanking and 6 figure sums could disappear on a given day, I checked it. Part of the reason I wanted to see the numbers is that I wanted to feel the pain, and imagine what that was doing to less disciplined investors or those with different time horizons. I don’t know what it says about me, but as I watch markets fall, my first thought is “how much can I afford to invest now?”

I missed the most recent bottom in 2020, but not by much. I think the market is up about 70% from where I doubled down in that correction. You can never perfectly time anything, but over a long enough arc you can sense market irrationalities one way or another and place some bets.

NET WORTH

How did you accumulate your net worth?

Like many other readers, I did it slowly. There has been no inheritance involved in my wealth creation, although it is likely I will receive one at some point in the future.

I already shared how I “paid” for grad school via some real estate luck (and it really was luck at that time). I have also shared how my career trajectory really changed my earnings profile. But along the road, the ball didn’t always bounce the way I wanted it. There were both personal and professional disappointments along the way that set me back.

I spent most of my 20’s working really, really hard. Moving for my career allowed my earnings to grow. But beyond just W-2 earnings, my career growth allowed me to get equity.

I learned to think like a CFO, recognizing that while my revenue and income may be good, through assets you can get leverage, and through leverage you can supersize your returns. It’s one of the most compelling reasons to be a real estate investor. As an employee, equity in your company is your piece of real estate where you get to participate in the growth of a much larger entity. My first equity grant at the VP level turned into a nice six figure sum. It was a good lesson on the value of fighting for that equity.

What would you say is your greatest strength in the ESI wealth-building model (Earn, Save or Invest) and why would you say it’s tops?

This reminds me of that riddle “What walks with four legs in the morning, two legs at lunch, and three legs at dinner?” The answer is “man” and the day is used as an allegory of human life as you go from toddler, to adult, to requiring a cane.

Similarly, at different times in life I have needed to excel at each of the ESI disciplines.

Initially I invested my time (and someone else’s money) in education. Then I went into debt (a form of investment leverage) for my graduate degree to be able to earn a higher salary. Once I started earning a salary, I had to save to buy that first house. Ultimately, investing in my first home allowed me to eliminate debt, which then meant I could start to save more, and invest again. It’s a cycle. You need to become adept at all three.

I would have to say “EARN” is probably the most natural for me, but “INVEST” probably wins by a nose. I would add that I very much view time as an investment asset as well. As such, I chose to step away from picking individual stocks (although historically I have done well when picking them), because the time investment required for consistent success is very high and would come at the cost of family time. I make similar choices on a frequent basis.

What road bumps did you face along the way to becoming a millionaire and how did you handle them?

By far the biggest financial hit in life was divorce.

I’ve run the numbers, and while everyone’s situation is different, I can definitively say that it cost well over a million dollars. Despite sharing time with our children evenly, the state in which I reside has laws that protect mothers more than fathers, even in cases of joint custody. That has many ripple effects.

Beyond the assets that were divided, there are ongoing impacts. One example is that my second largest expense cannot be altered or reduced (child support). I pay almost as much in child support as I do in housing. In turn, that requires a certain level of income to accommodate, which also impacts what kind of career choices you can make. I have had to turn down extremely enticing career opportunities (potentially life changing from a wealth creation perspective) as I couldn’t relocate without needing to choose between career and family. In that equation, there really isn’t a choice as no opportunity is more valuable than time with my kids.

Financially, divorce leaves you with the following financial headwinds:

• Division (reduction) of assets at time of divorce
• Legal fees
• Alimony payments
• Child support payments
• Reduction in career opportunities (if you have kids and aren’t mobile)
• Elimination of tax arbitrage opportunities (i.e. you can’t move to a lower cost or lower tax jurisdiction without sacrificing your family time)
• Reduction in child tax credits with joint custody

Now, with all of that said, I am unbelievably fortunate. My ex-wife is remarried to a good man who is good to my kids. Having an ex who is amicable and supportive is a huge advantage. Our schedules vary tremendously from month to month, and we work together to balance between our households which has enabled some career progression.

I know many others who have gone through my situation and are still, years later, unable to talk to each other or even be civil. I struggle to understand that, especially when you have children and you are both fully committed to their well being. Life is too short to waste it being bitter.

Ultimately, when you look at the impact of divorce through the lens above you can do your own NPV calculations on its financial impact. However, my calculation is not a stretch at all, and frankly may be conservative. That is the financial reality.

Outside of the financial impact, all of us are in better places and thriving, and you have to balance that and not solely view it through the financial lens.

What are you currently doing to maintain/grow your net worth?

I continue to save and invest, fully funding every tax deferred account as a priority (including my HSA), and then flowing to taxable accounts.

I also invested in life insurance policies when I was younger primarily to have another tax deferred vehicle where I could accumulate assets. I know these are controversial to many, but this was really driven by not having access to many tax deferred vehicles and recognizing that the costs of these insurance vehicles were offset by the tax shelter over time.

Before I was even 30 I no longer qualified for a Roth IRA, and at the time the 401k max contribution was something like $10K. Insurance was one of the few tax shelters available to a high earner without his own company.

A few weeks ago I used the cash values of those policies to open up a line of credit that, when exercised (for pretty much whatever I want to use it for), would basically charge LIBOR. With that capital, I am investigating some real estate ideas, but admit I am a little reluctant as I do not enjoy being a landlord and would need to outsource pretty much everything for it to work. If any readers have advice in this area, I would surely welcome it. Valuations do not feel very attractive to me right now.

The other big question for me right now is, ironically, my career. While the journey has been amazing, I find that it is becoming a bit more of a grind. While part of me fantasizes about just walking away, I would regret not seeing this one through to an exit. The satisfaction of climbing the corporate ladder and gaining membership in the C suite required a lot of energy, and upon arriving it hasn’t lived up to my hopes.

Given the considerable equity I have, the exit will be material and could take another 2-4 years. That is probably the single biggest financial decision I can make right now, but those 2-4 years could be long years.

As I find my mind wandering to a vision of a less scheduled future, I am starting to spend more time educating myself on ways to develop passive income, whether that be through dividend stocks, real estate investments, or potentially some other venture.

If I do end up pulling the trigger, I will need to make sure I have stable income & insurance for the next few years until the kids leave the house. Their college educations are pretty much fully funded in 529’s that I count as theirs, not mine.

Do you have a target net worth you are trying to attain?

Not really.

When I was younger, I thought $3M would do it.

As life progressed, I thought maybe $5M was right.

Now, I just think about what cashflow I need for what kind of lifestyle.

I think $5M is a “pretty good” number in terms of a long retirement, but I have a chance to make it to $10M+ with a little bit of luck and depending on how long I choose to work.

I should add that the numbers I am referencing above are “liquid” numbers, not net worth as traditionally defined. While I certainly have assets that could inflate my net worth (cars, artwork, etc), I really think of net worth as an intermediate value leading to a cash flow metric which is ultimately more important.

How old were you when you made your first million and have you had any significant behavior shifts since then?

I was about 33 when I crossed the mark the first time, but then divorce put me back under. The second time I was 37/38 I believe. The 2nd million came a lot faster.

The biggest behavior shift is that now I really think about finances through the lens of time. The FIRE movement certainly caught my attention and imagination. I always said I wanted to be able to retire (whether I do or not) by the time I am 50. As I approach that milestone, I think I will be able to do that by then if there aren’t any major (negative) surprises. However, I will need to start elevating my passive income game pretty soon to feel comfortable pulling that trigger.

The other change is that I realize the happiness that can come from financial security is finite. Meaning, whether I have $200M or $400M it would make (almost) no difference in how I live. However, the peace that is provided between $1M and $2M is material. You reach a point where there are diminishing returns, and neither your time on this planet nor your happiness is extended by adding an extra zero to your net worth beyond a certain threshold.

What money mistakes have you made along the way that others can learn from?

When I think about what I would do differently, only a few things come to mind and I think I have already exhausted the point of choosing your spouse well.
Overall, I spent most of my 20’s and 30’s with very little cash on hand. Opportunities would appear, and I had no ability to invest as I was so tight on cash because I was 100% loaded on real estate, the market, or tax-deferred investments.

I mentioned earlier how I tried to invest after every major crisis, and while I did, it was not nearly as much as I wanted. Had there been $200K more in cash reserves at each event, my net worth would be materially higher. But much like in the game of Monopoly, you can only buy assets if you have the resources to do so. I underestimated the importance of cash(flow) early in life and for many years.

Another one that comes to mind is investing in raw land. I bought some land when I was younger, and it was in this gorgeous area that I very much fancied as a retirement/vacation location. I held on to it far too long with that dream in mind and over the years paid a lot in property taxes etc that I shouldn’t have. In hindsight, that was an emotional decision and I could have used that money much better elsewhere. I was thinking about a dream, and not about my reality. Those carrying costs sneak up on you.

What advice do you have for ESI Money readers on how to become wealthy?

I would go back to one of my earlier points and say “know thyself”. Determine what wealth means for you first and foremost.

Recently I have become more active in my church, and my wife works for a non-profit organization that does tremendous work. I could be financially much wealthier than I am today if I had made some different life decisions that were non-financial, but I wouldn’t like myself and would face regrets that could not be remedied. Wealth was less important than time with my kids.

While I was always financially savvy, I pay a lot more attention now to TIME and HEALTH. Aging parents struggling with their health really humbles you, and makes you realize that money cannot truly solve some of life’s challenges. So, measure your wealth wisely and don’t let it solely be determined by numbers following a dollar sign. I am wealthy beyond measure in family, friendships and faith. I also invest a lot more time in ensuring that physically I will be able to enjoy my future.

FUTURE

What are your plans for the future regarding lifestyle?

I want to step back and define my next chapter. Assuming things go as desired, I’d like to get to a liquid net worth north of $3.5-4.5M, and evaluate. On our current trajectory, I can be there with or without an equity event at my company. If there is an equity event, it likely adds $1M+ to that number. If that equity event happens, I will likely take a sabbatical and spend a few months seeing how life feels without a hyper-programmed, goal-oriented lifestyle.

Once I do take that step back, I suspect I’ll need a few months to just decompress. After that though, I will need something to pour myself into. Maybe a couple somethings.

Once the kids go to college, it is likely that my wife and I will move. She moved to my state to be with me while we raise the kids, but college is only a few short years away, and when that happens I expect we will select a new home base (hopefully in a friendlier tax environment). Whether we work or not is TBD, but if we do work, it will be something from which we derive tremendous satisfaction and won’t be a financial decision. I could see us working just to have some health benefits perhaps.

What are your retirement plans?

Retirement likely involves either snowbirding for a few years, or potentially a move overseas for a period of time.

We don’t anticipate working for money, although I could see us doing something to keep us busy that maybe provides health benefits.

I have a long list of things I would like to learn, and there are a lot of bodies of water that remain to be fished.

The world is out there, beckoning….

Are there any issues in retirement that concern you? If so, how are you planning to address them?

Like everyone else, healthcare. We will need to get insurance for an extended period before Medicare kicks in, but there may be a chance that health expenses will be lower if we move overseas. We don’t have this one figured out yet.

Another one is aging parents. We are blessed to have both sets of our parents still alive, but they are aging and not all in the best of health. While the allure of the overseas retirement calls, duty to the people who raised us calls as well. We will need to balance between those priorities for a while.

Lastly, I worry more and more about the macroeconomic health of the US economy and currency. With all of our assets USD denominated, I think there is a decent chance that the value of the dollar dramatically decreases in coming years. I would like to find a way to hedge against that in an organic way. Potentially real estate overseas, or some other asset that wouldn’t be subject to the currency risk that $30T, $40T and even $50T in national debt introduces.

MISCELLANEOUS

How did you learn about finances and at what age did it “click”?

I think the “aha” moment for me was in college. As I said before, I wasn’t a great (or even good) student. I went to good schools and did the bare minimum to get by.

My sophomore or junior year in college one professor started his class by saying, “You will want and need to attend my million dollar lecture on September ___th. During that lecture, I will write a future dated check to any of you who attend in the value of $1,000,000 as a personal guarantee that you will be millionaires if you follow my advice”. He had me.

His million dollar lecture was the one many of us have heard about starting to save and invest early, as little as $2K a year invested annually for 40 years will get you there. But how he spoke about finance inspired me to learn more. He was the spark.

The other person who inspired me was my father. He grew up on a farm and didn’t have many of the opportunities I was given. But for a guy who barely made it through his education, he has done so well and taught me so much. He self taught himself about a variety of financial vehicles, self educated on legal frameworks that would benefit him and his family, and carved a financial path that is staggering considering he did not have a single personal finance class in his life.

Who inspired you to excel in life? Who are your heroes?

My father.

It’s hard to do him justice. He grew up working hard before and after school on a family farm. With the habits he developed as a child, and those that were instilled by his father, he would wake up routinely at 4 am, exercise, and be in the office before sunrise most days.

Beyond instilling a work ethic in his kids, he also instilled a moral code, a conscience, and a recognition that we are our brother’s keepers.

While Dad was a success in his career, he was an even bigger success in his love for his family and his devotion to his faith. Never one to brag, he just humbly went about being the leader he was. People would walk through walls for my dad because he was honest, direct, and believed in treating people well. He just made those around him better, and he wouldn’t let you rest until he felt you had nothing more to give or to grow.

Do you have any favorite money books you like/recommend? If so, can you share with us your top three and why you like them?

I am annoyed with myself that I cannot find/remember one of the books that I really enjoyed, which spoke to relationships with money. It had an eastern philosophy bend to it, and I read it in my 20’s and it really got me thinking about my relationship to money and what it represented. It was less tactically oriented, and more about the psychology of money and understanding your relationship (past, present and future) with what it enables. Unlocking that relationship and translating money into what it represents were core tenets. It helped me define money as freedom as opposed to possessions.

Beyond that, Rich Dad, Poor Dad was also one that got me thinking. I attended one of their seminars, which went an inch deep promising greatness at every turn if you just spent more, invested more, etc. The premise of the book was great, the downstream “advice” left a lot to be desired.

Millionaire Next Door should be required reading for most college students. Good, common sense advice on what wealth looks like and how it is created. A very large portion of the US population thinks that the 3% or the 1% really live like the .0001%. This book did an excellent job of demystifying the cumulative benefits of certain choices (and in many ways exemplified Atomic Habits).

Do you give to charity? Why or why not? If you do, what percent of time/money do you give?

We do give to charity, although probably not at the level we will in the future.

We primarily give to our church, but also to the non-profit where my wife works amongst a couple of others.

So far, I think our charitable donations have been modest (<5% of income/yr), but I do expect that to increase. We are also considering a DAF at some point, but that may wait until we see what, if any, tax law changes come in the next 12 months.

Do you plan to leave an inheritance for your heirs (how do you plan to distribute your wealth at your death)? What are your reasons behind this plan?

We do, but it will be coincidental. We have no explicit goal to provide multi-generational wealth, but would like to provide the tools for that to be created. It will require the input, effort, and prudence of our heirs to continue that legacy.

Whatever wealth is left at our death will eventually be distributed to our (my) heirs, but I have also opted to not give them access to all of it until they hit certain ages. As life gives them opportunities to acquire wisdom, my hope is that they find themselves increasingly knowledgeable about how to best use what comes their way.

It is also likely that when the time comes I will attempt to save a material amount of money for the education of grandchildren. I’d like to continue to ensure that our family is able to receive a college education, although what that will look like in 30 or 40 years is anybody’s guess. However, along with financing their academic education, I am hopeful that the broader life lessons involving hard work, grit, tenacity, kindness and fairness are instilled in them by their parents and me.