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 December.
My questions are in bold italics and their responses follow in black.
Let’s get started…
OVERVIEW
How old are you (and spouse if applicable, plus how long you’ve been married)?
I’m 56 and my spouse is 71.
We’ve been married 29 years.
Do you have kids/family (if so, how old are they)?
We have two daughters (I say that I married my wife and the kids were preinstalled. Haha!)
They are 34 and 33, both married to great guys, and have provided us with amazing grandchildren.
What area of the country do you live in (and urban or rural)?
I live in a semi-rural area outside a suburban city.
What is your current net worth?
As of today, our net worth is conservatively $3.2 million.
I say “conservatively,” because I’ve removed assets that we’ve moved into trusts from the list, and because the real estate is not marked at “retail” Redfin or Zillow numbers, but rather what I believe we would net after paying all the fees, taxes, etc. I don’t update the real estate numbers often (maybe every couple of years).
What are the main assets that make up your net worth (stocks, real estate, business, home, retirement accounts, etc.) and any debt that offsets part of these?
Assets:
- $975k – Traditional IRAs
- $515k – Roth IRAs/401(k)s
- $655k – Rental Properties
- $750k – Primary House
- $200k – Vacation House
- $110k – Short term loans
- $370k – Savings
Liabilities:
- $74k on vacation home (at 2.75% mortgage rate)
- $301k on two rental property mortgages
Net Worth: $3.2M
We have a stake in a couple of small businesses, but it’s way too difficult to estimate their value, so I don’t include it.
I am also not including depreciating assets like cars (we have three cars, no auto loans).
EARN
What is your job?
I work in enterprise software sales for a Megacorp as a director-level individual contributor.
I’ve been in software for decades, and this job is the culmination of a wild career that bounced around quite a bit, starting as a financial analyst, then founding my own software company (with my wife), then going into real estate for a decade, only to come back to IT, my true passion.
My current role is mostly advisory and strategy.
What is your annual income?
The past several years I’ve been in the $400-$450k total earnings range. This includes base pay, bonus, and Restricted Stock Units (RSUs), as well as contributing the max to my company’s Employee Stock Purchase Program (ESPP).
My wife has been retired for the last couple of years, but she has “mailbox money” to the tune of a small pension and Social Security benefits.
With a couple other small income streams (including my wife’s “buyout” from a business transfer that will come to us over the next several years), we will likely end 2023 with gross income in the $550k range.
Tell us about your income performance over time. What was the starting salary of your first job, how did it grow from there (and what you did to make it grow), and where are you now?
After graduating college in 1990, my starting salary for a job as an economic assistant was $23k. And boy was I thrilled, because I knew I only had six months to start paying my student loans back!
I graduated with around $11k in student loan debt, including Guaranteed Student Loans (GSL) and Parental Loans for Undergrad Students (PLUS) loans. My grandmother co-signed for my PLUS loans, and there was NO WAY I wasn’t paying those loans back ASAP!!
The Discover Card had just come out while I was in college, and I applied for one, received it (their standards must have been quite low), and charged my final semester’s tuition and books on the card, maxing it out. I think I owed about $5-$10k in credit card debt at graduation.
Naturally, I bought a new car and added another $12k of debt to the pile. I think at my nadir, I had a net worth of about -$35k with car, student, and credit card debt.
Given that stressful financial backdrop, I lost my very first “real” post-college job after six months due to downsizing during the recession of the early 1990s. It took me three months to find another job as a financial analyst, which made losing my first job a blessing in disguise.
At my second job, I was promoted yearly and met my future wife! I started making $19k, then got promoted after 3 months to $27k, then $35k, with more salary increases of about $9-$10k annually until I was making about $75k. In the early 1990s, this was good money!
My future wife, being 15 years older than me, was making quite a bit more money. In fact, she continued to out-earn me until about five years ago. This was not a problem at all to me; I was enjoying living a life that was “advanced” compared to most of my peers, in a detached home with kids at the tender age of 25! (My wife says that I was “prematurely mature,” and I must agree.)
During the last 3 years of my “corporate” career, my wife and I were both working a side gig founding and running a web software company. We eventually decided to make a go of it, so I quit my day job (yikes!) and took the plunge. My wife (the larger breadwinner) went to part time the exact same day! Our income dropped by over 60% in one fell swoop.
We ended up building the company to about 15 employees, had a loyal client base, and sold our company to a competitor a few years later. On paper, I don’t think I ever made over $75k annually until the year we sold. It was more of a passion project, in retrospect, but I learned a lot that would serve me later.
Now that the software company was sold, what to do? My wife and I both enjoyed the idea of flipping houses, so we got our real estate licenses. This was while also doing an “earn out” from the software company we sold to. We transitioned into real estate, intending to flip houses, but we ended up in sales. That career lasted ten years for me and longer for my wife, and we had the good fortune to build another nice business that continues to this day. My personal income varied wildly during this time, bouncing between $80k and $180k.
Once I decided to move away from real estate, I had the opportunity to jump back into IT as a CIO for a government agency. This was quite a shift for me by then, since I was used to being my own boss and working from home, but it was too good an opportunity to pass up! After a couple months of learning names and systems, I realized that this agency was very similar to the web software company I sold, with every line item in the budget simply being followed by more zeroes.
I worked at this government agency for four years, until the administration changed, and I was shown the door. Another seemingly bad thing that turned out to be a blessing in disguise! My highest salary at the agency was about $150k a year.
That led me to my current job at Megacorp, where I get to use much that I learned as a software developer, financial analyst, salesperson, and IT professional to help people make wise enterprise software decisions and formulate strategy. My current gig is remote with some business travel, much less than before COVID, and I’m enjoying the work. Once my RSUs began vesting about a year after I started, my pay range has been $400-$450k annually.
What tips do you have for others who want to grow their career-related income?
My best tip for those who want to change careers is to start a side gig in that field while you are currently employed! Don’t put extra pressure on yourself by quitting and then also having to figure out what you’re doing.
My wife and I started our software company from home, got customers, did all the work, from programming, to web design, to building and securing servers, to managing domains, AD servers, email, everything you need to make a company look professional. We knew what we loved to do, and we learned what we did not enjoy. Our first hires were people who complemented our strengths, made up for our weaknesses, or enjoyed the work we did not.
My second tip is to consider a career selling what you love. I honestly didn’t know about jobs like the one I have until I got it! I’m in “sales,” but not every sales job is the same. One consistent thing, however, is that there is no limit on your earnings in a sales career.
I’ve sold houses as a real estate agent, I’ve sold software as an entrepreneur, and am now part of an enterprise software sales team that operates globally. A great salesperson is a great consultant and strategist, one who listens to people and helps them get what they need and want. And if you’re passionate about what you’re selling and believe in the company and its products or services, it can be very rewarding.
Just think about it, that’s all I ask, especially for those of you who saw “sales” and thought “ugh.” (You know who you are!) 😉
What’s your work-life balance look like?
It’s been good lately.
Early in my career, I leaned too heavily into work. Starting a business was the most demanding thing I’ve ever done. We were teetering on the edge of shutting down multiple times when I was CEO of our small business, and I had personally guaranteed business loans (to the tune of about $50k) and had to make payroll every two weeks for over a dozen people. And I was working 60+ hours pretty much every week. Stress!
Now that I’m in the corporate world, it’s great to have a team (and not have to make payroll!). I’m intentionally working on helping others in my company look good, and that type of behind-the-scenes work can be done remotely. I have some business travel, which is annoying because it takes me away from my grandkids (who live down the road) and my wife/kids, but it’s leveled off.
All in all, a good balance right now.
Do you have any sources of income besides your career? If so, can you list them, give us a feel for how much you earn with each, and offer some insight into how you developed them?
My wife has a small pension and is currently collecting Social Security, having waited until age 70 to maximize that government-backed income stream. We’re banking that money while I’m still working and building up our cash reserves as we start the glidepath to my retirement soon.
The net income from our rentals is getting rolled back into paying off the mortgages. We have all excess funds going to pay down the property with the highest rate mortgage (which is currently only 3.375% but it’s an ARM and it’s set to adjust in February of 2024).
Nothing else of substance to report.
SAVE
What is your annual spending?
Here is where I deviate from most other ESI interviews! We can spend some money.
Our annual spending is about $180-$200k, and we’ve intentionally increased spending prior to my retirement to get used to this level.
What are the main categories (expenses) this spending breaks into?
Here’s what Quicken is showing for 2023 (I’m removing rental property expenses from the list, although they are the largest line item for me):
- Travel – $35k
- Family – $20k (parents, kids, grandkids)
- Charitable Donations – $15k
- Vacation home – $15k (had to buy a new HVAC this year)
- Food – $15k
- Home improvement – $15k (whole house generator)
- Household expenses – $15k (this includes legit household expenses plus a lot of “Amazon” purchases where I have no idea what it’s for!)
- Insurance – $14k (and set to go much higher next year with our Long Term Care policy premiums skyrocketing!)
- Farm expenses – $14k (I live on a farm and we’re adding infrastructure – some of this is deductible or depreciable)
- Property Taxes – $14k
- Autos – $10k (all three cars in the fleet needed some significant regular maintenance)
- Utilities – $9k
- Health & Fitness – $7k
Do you have a budget? If so, how do you implement it?
We have never had a budget. Our philosophy has always been to max out our retirement contributions, scooping up any company match, then pay extra on any mortgages or other debt.
We also have a philosophy to enjoy the journey that is life. My wife instilled this in me a while back. Enjoy your time now because tomorrow may not come. Take nice vacations with your family and create lasting memories. Indulge occasionally, as long as you’re meeting your overall goals and objectives.
What percentage of your gross income do you save and how has that changed over time?
This has varied wildly.
Early on, I was saving enough in my retirement accounts to get the full company match – I think it was 6%. I was also paying off student loans, car loans, and credit card debt. I guess that counts as “savings.” But the “official” savings percentage was only around 6% initially up to about 12% when I left my first corporate job.
When we were entrepreneurs, we tried to contribute as much as we could in our SEP IRAs or solo 401(k)s, but when you make little income and roll most of your funds back into the business, there’s little left for retirement contributions. So those years were light in the savings department. When you’re building a company and taking almost no salary, it’s hard to prioritize retirement savings. I wish I had done more, though.
This year, we’ll save about 30-35% of our gross income, including maxing out my Roth 401(k), mega back-door Roth, paying extra on mortgages, and just plain saving in the savings account.
What’s your best tip for saving (accumulating) money?
First, read “Your Money or Your Life.” That book changed how I saw trading my life energy for “stuff.”
Aggressively pay off the highest interest rate debt first. Pay off credit cards, car loans, student loans, all before you pay extra on your mortgage (unless your mortgage rate is higher). The snowball effect is real!
It got to be a game when I knocked out my first credit card, then doubled up on the next, and the next, then started taking out student loans – first PLUS, then GSL, then my car loans, and finally my primary residence mortgage.
I never had an “emergency fund” until recently. I considered my credit limit minus my current card balance to be my “emergency fund” while paying off debt. Some people might not be comfortable with this method, but it worked for me. I couldn’t see saving three months of expenses in a savings account earning under 1% interest (at the time) when I had credit cards charging me 18% or more.
Once the debt load is reduced, and while you’re chipping away, keep an eye on lifestyle creep. I’m fortunate that my wife and I have similar values; enjoy today, but only as long as you’re saving along the way. If you set up automatic deductions for your company 401(k), max other benefits like ESPP, mega back door Roth (if available), HSA, etc., pay extra on your big debts like mortgages and auto loans, you can “earn” some fun money.
One tactic I employ is to quickly move lumpy funds out of my checking account. If I sell RSUs or get my bonus and receive a lump sum, the first thing I do when I see that fat checking account is transfer as much as I can over to my high-yield savings account. I like to keep my operating accounts lean, so I don’t start to feel too comfortable.
What’s your best tip for spending less money?
I’m not the one to offer advice here – haha!
I focus on the big things – housing prices, interest rates, and trying to only buy things that give me joy. We don’t clip coupons or drive all over the place trying to find gas that’s $0.02 cheaper than our nearby gas station. But I do keep an eye on mortgage rates, and I refinanced multiple times as rates went lower a few years ago.
I’m happy to report that I have no mortgages over 3.5%, including investment property mortgages. I also tried to get the lowest rate on auto loans, then proceeded to pay them off aggressively. I would get a five-year loan and typically pay it off in 12-18 months. I noticed those loans helped my FICO score, too.
Other than that, just focus on buying quality and maintaining what I have. If you’re comfortable trading your life force (time) for something that brings you joy, then go for it. If you’re not comfortable making that trade, skip it.
My father-in-law used to tell my wife that every gadget or gizmo was “one more thing to break.” So true!
What is your favorite thing to spend money on/your secret splurge?
Travel. I’ve discovered business class airline seats, and I’m in love! We only started flying business class once we reached FI, and it’s been a wonderful reward for all the work of saving and investing. We splurge on business class tickets, and we upgraded our coffee from Kirkland to Starbucks at home. I’ve recently discovered Turkish baklava and have bought and shipped it from Istanbul – totally worth it!
My wife enjoys buying stuff for our grandkids. Once they get a little older, I’m sure I’ll add that to my list of lifestyle inflation splurges, too! We’ve purchased a big all-inclusive tropical family vacation for us, the kids and spouses, and grandkids last year and had a blast! We recently booked another all-inclusive vacation for everyone this July. I can’t wait!
INVEST
What is your investment philosophy/plan?
My philosophy is to buy what I know (tech stocks primarily) while balancing that risk/volatility with sound conservative moves like paying off my primary house mortgage and building up a sizable cash reserve. We have no real “plan” in place, but we will decide on a purchase based on what we already have in our portfolio.
For example, we bought a couple of investment properties when we didn’t want to put any more money into the stock market. I consider our real estate to be bond equivalents, so we don’t invest in bonds (although that may change in 2024).
At this point, my new philosophy is to avoid the temptation to buy more individual technology stocks and instead buy broad index ETFs. It’s a work in progress.
What has been your best investment?
I bought Apple stock and I’ve had my company’s stock since well before I joined them as an employee. Those are my two best returning individual stocks so far. Microsoft and Amazon have also been quite good to us over the years.
I put myself through college and was the first person in my family to have a college degree. I filled out the college application, all the FAFSAs, applied for grants/scholarships/loans/work study, and squeaked by with a bachelor’s degree just as my credit cards were maxed out, working through the entire four years, including summer and holiday jobs that made me very happy when I could return to school. That investment turned out to be brilliant, although I’m not as certain of its return these days.
What has been your worst investment?
I bought EFAX back in the 1990s, and I think that stock lost about 95%. Luckily, I only had a couple thousand dollars in it. One of my close friends still teases me about that debacle. At least I didn’t put money in pets.com – haha!
We also invested in a startup not run by us (big mistake!) and that $10,000 investment went to zero. We never bet more than we could afford to lose, but it still sucks when you see your investment head toward zero.
One other category of bad “investments” – loans to family. My advice is if you loan money to a family member, assume it’s a gift. Then you won’t be surprised (and disappointed) if it turns into one over time. If it gets paid back – found money!
What’s been your overall return?
Over the last 12 years, my net worth compound annual growth rate (CAGR) is 12.5%.
This includes all savings and investment returns – I don’t separate those. I just tally every account balance up monthly and then look at the overall number.
How often do you monitor/review your portfolio?
Way, way too much!
Since I’m closing in on retirement, I’ve been obsessed with Monte Carlo simulations and my sequence of return risk (SORR). I have all my stock holdings in an Excel retirement spreadsheet, and I refresh that page a couple of times a day when working from home.
Once a month, I go into all my accounts and update balances on my monthly tracking page, my “official” numbers. I update all financial accounts monthly, but only update property value estimates every couple of years. I find more comfort with very conservative numbers.
NET WORTH
How did you accumulate your net worth?
My wife and I were both in debt when we met. She probably had a positive net worth because of her house (maybe $30k), but that was about it. We both saved in retirement accounts regularly, at the very least enough to get every penny of matching funds.
We focused on automating in every way we could, mainly to avoid the credit hit and penalties from forgetting to pay a credit card balance monthly or being late with a car payment. Those junk fees and high interest rates can destroy your momentum!
We focused on paying off debt. I mentioned our snowball plan before – pay off the highest interest rate loan balances first, and then double down on the next one.
Our big accomplishment was eventually paying off our $417k mortgage on the house we’re now living in. It took years…and years…and years, but with that albatross gone, our savings have been in turbo mode! I can now max out my work retirement accounts, adding $65k+ of after-tax money to those Roths, and survive on my diminished paycheck until I get to quarterly RSU vestings. That savings adds up fast.
We’ve bought and sold a couple of primary residences, making good money on one and losing money on another. We did a few property fix-and-flips and pretty much broke even.
Where we have really seen real estate positively move the net worth dial is buying and holding investment property. We waited until we had a 25% downpayment to avoid Private Mortgage Insurance (PMI) and get the best investment mortgage interest rates available. We were also in the real estate business as agents, so knew when we found a good deal. If you buy a property and put enough money down so the payment is no more than the rent you can collect, after several years you’ll see rents going up faster than your expenses with a fixed-rate mortgage. Just be sure to have a cash reserve for repairs and unexpected vacancies!
Since 2016, our tech heavy investment portfolio has really taken flight. The volatility can be nausea-inducing, but overall, it’s been a great investment. I’m lucky in that tech is the one area where I feel comfortable making individual stock selections, and picks like AAPL, MSFT, and others have done nicely. Moving forward, my plan is to de-risk slowly and move into more ETFs that cover a broad swath of the market, like VTI.
My wife’s father passed away and left us some assets that we put in a trust for the children, except for about $250k, some of which we recently received in cash. These funds are added to our savings, making it more than we normally carry in cash.
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?
Five years ago, I would have said Save is my strength, but I’ve noticed that the last five years of good Earnings have really propelled us. It’s the combination of high earning and high saving in the last few years that have gotten us to financial independence (FI). We’ve done okay with Invest, but certainly could have done better. So that’s not a strength. I’m probably average on Invest.
Many people in the Millionaire Money Mentors (MMM) forums have pointed out that a prodigious savings rate and good earnings can help make up for boneheaded investment decisions. I am proof of that.
What road bumps did you face along the way to becoming a millionaire and how did you handle them?
Most bumps were self-induced and involved quitting jobs and striking out on our own. We didn’t focus on saving when we were bootstrapping companies, and we lost several years of potential savings and growth.
In 2009 we were going through a very lean time in terms of income, and were scared to put money in the stock market, so we lost momentum by not saving and by having too much money on the sidelines. We were doing some hard money lending, but those 8-10% returns carried the overhead of serious due diligence, as well as being nearly impossible to keep money invested. One or two of the projects were finishing up constantly, and when the cash was returned it would sit in savings until we redeployed.
I bet we didn’t make more than 5-6% during that time, and we missed out when the stock market was recovering. We returned to the warm embrace of Mr. Market by 2013-2014.
Another road bump involved my wife and me both having the same income source, essentially putting both career eggs in the same basket. We really enjoy working together in our businesses, and made that choice knowing the risks, but I can tell you it’s a lot easier when we have different income sources. There’s a compound effect when you separate income sources, too, that can really drive the E of ESI.
Like most folks, 2022 was a solid road bump on our financial path. We lost net worth for the first year since I started tracking in 2012. We stayed the course, continued to max out our retirement accounts, continued to save, and as of today (end of the year 2023), all is good again. Whew!
What are you currently doing to maintain/grow your net worth?
I’m trying to figure out how to land this plane and retire soon! Haha! So my focus is to de-risk my tech-heavy investments while those stocks are near all-time highs and put the funds into broad market index ETFs with low fees.
I’m also maxing out my retirement options at work and saving my wife’s Social Security payments until I leave the W-2 world. I’d like to have at least two years of cash to cover expenses (less other income streams like pension and SS) in our high-yield savings account. That sequence of return risk has me nervous!
Do you have a target net worth you are trying to attain?
For some reason, I always thought I’d need $5M for the Chubby FIRE lifestyle I wanted, but I’ve since seen that other income sources can make up for cash in the bank. There’s recently been a “should pensions be considered assets” conversation in the Millionaire Money Mentors (MMM) forum, and I can see the value of both pensions and cash in the bank (although, for the record, I’m in the camp of “no, pensions are not assets, but are nice for cashflow”). Since my wife has both pension and Social Security income streams flowing, and since we paid off our house, we need less cash to cover the rest of the month’s bills.
I think where we are now, with a net worth of $3.2M and investable assets of about $2.3M, is sufficient for me to retire. That said, I am looking forward to breaking the $4M net worth barrier some time…hopefully soon. Once I get comfortable with no W-2 income, and once we get a reliable cadence of retirement living, I plan to give money away while I’m around to enjoy seeing it put to good use.
How old were you when you made your first million and have you had any significant behavior shifts since then?
I was 46 when our net worth crossed into seven digits.
Other than maybe a bottle of champagne, no behavior shifts.
Once we achieved FI (in the last couple of years), we did have some behavior shifts around flying business class and taking more epic vacations.
What personal habits and/or traits have you developed that have made you successful at growing your net worth?
My wife calls me “Tracker Boy,” and that tracking habit helps immensely. Seeing progress is important. My ritual of closing out each month in my retirement spreadsheet helps me see progress and also see where we might have concentration risks with our portfolio.
My wife and I are both competitive, and I feel that helps with our careers. We were not afraid to quit a job and start something new, even in a totally different industry.
Finally, being willing to jump in – “just do it,” as Nike says. Sometimes you just have to buy the stock, buy the property, quit the job, start the business, and stop analyzing the crap out of life. Just do it.
What money mistakes have you made along the way that others can learn from?
I would have bought more ETFs and fewer individual stocks if I had a mulligan. I’ve done well in a few, bombed in a few, and probably overall matched total market returns, all while adding stress and volatility. Not the best idea. I’m just lucky it has worked out.
I would have relentlessly focused on getting my retirement contributions up to the maximum allowed by law and kept them pegged there. I’ve done that since 2015 and the accumulation has been amazing.
I would have saved more in regular old taxable accounts – both savings and investment. It’s good to have options as you near retirement, especially when it comes to RMDs and retiring before your pensions/Social Security kicks in. I’m just lucky my wife is 15 years older than me and has activated those income streams already!
What advice do you have for ESI Money readers on how to become wealthy?
Follow the simple and plodding path to success that most ESI interviewees have already explained far better than I could.
Focus on the big things – affordable housing, reliable autos, staying out of credit card debt.
Automate savings, especially retirement savings.
Never leave a cent of matching contributions on the table – contribute at least enough to get all the match! And do that right now!
Follow a career path in something you’re passionate about. Consider sales as a path to turbocharge your earnings while also helping your customers become successful with your products or services.
FUTURE
What are your plans for the future regarding lifestyle?
My plan is to retire in the next year or two, then maybe find something in the personal finance industry (advisor, etc.) that I can do part-time, preferably helping young people get their act together and start building for the future.
We spend a lot of time with grandchildren. I see that continuing. Once the grands get a bit older, I want to help them with homework, take them on vacations, and otherwise spoil them mightily. Our kids are 100% onboard with this plan, and they will get to come along!
I have ideas for some retirement hobbies, but can’t allow myself to spend too much time thinking about that now. I already have a solid case of “senioritis” and can’t wait to graduate to the ranks of the Retire Early crowd! (My case will be barely early, but still good enough for me!)
What are your retirement plans?
One of my big retirement goals is to be able to maintain my spending level without having to cut anything. I might decide to reduce spending, but I have had a “scarcity mindset” about money, mostly from growing up without much, and I’ve managed to move to “abundance mindset” only in the last 3-4 years. I don’t want to go back to scarcity thinking, and my wife gives that a strong second! Therefore, the plan is to make sure we have enough income to maintain current spending.
We have budgeted for two nice vacations a year (one for my wife and me, one for entire extended family including kids and grandkids). Travel is so enriching and it’s something we want to help our grandkids discover.
I would like more time to sit down and read, to get better at chess, and to write. I really want to help young people with financial literacy. Turning that into a part-time job would be a dream!
Are there any issues in retirement that concern you? If so, how are you planning to address them?
Staying away from my prior mental state of “scarcity mentality” once I stop getting W-2 income is paramount. I need to feel comfortable with our multiple streams of income. It’s going to take a while.
I’m also looking forward to getting past the dreaded “sequence of returns risk” (SORR) timeframe – the first 5-10 years of retirement. Once we clear that hurdle, I’m looking forward to increasing our gifting and charitable contributions.
MISCELLANEOUS
How did you learn about finances and at what age did it “click”?
I was an economics major in college, so I understood finances in theory. However, it didn’t “click” for me personally until I read “Your Money or Your Life” back in the mid 1990s. After reading that book, I really doubled down on reducing spending, paying off debt, and looking at every purchase in terms of trading my life energy for stuff. I was probably 26 or 27 at the time.
I discovered that we could actually have a decent retirement after I was tracking our numbers every month. I ran some crude projections based on estimated savings, conservative investment returns, and other sources of income. It dawned on me that we would have over $100k/year coming in. Liberation! That was probably around 2013 or 2014, so I would have been mid 40s.
In terms of retiring EARLY, I didn’t see that as a possibility until I discovered ESI Money and read dozens of interviews. I found other websites and consumed a lot of FIRE content from J.D. Roth, Mr. Money Mustache, Gen Y Finance Guy, and many others. It inspired me to double down on my tracking. These folks knew their numbers, and I should know mine, too.
My retirement spreadsheet has dozens of pages and many different “back of the envelope” calculations to see when we have enough for me to retire. I discovered the New Retirement website and their retirement modeling tool a few years ago and have used it since. (My opinion – totally worth the premium subscription!) I also used the Fidelity retirement tool.
After many, many, many combinations and permutations and Monte Carlos, I’ve become more comfortable with my plan to Retire Early (RE). If 57-58 can be considered early to some of the people reading this who are targeting 38-40 to FIRE, haha!
Who inspired you to excel in life? Who are your heroes?
My parents inspired me in their ability to provide me with a great childhood on a limited income. We never went hungry, but we had powdered milk and “old folks cheese” on the menu often.
My grandfather (who I never met) was an inspiration because I saw pictures of him in the army during World War II and heard stories of how he fought with the tank destroyers at the Battle of the Bulge. He paid a price for this country, and I salute him and all our military and veterans.
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 think everyone knows by now that I love “Your Money or Your Life.”
Another favorite is “The Millionaire Next Door.” I read it and thought how cool it would be to be one of them. Each story was different, but there were themes we could learn from (just like these ESI interviews). Inspirational!
“Cashflow Quadrant” by Robert Kiyosaki is another favorite book of mine. The E-S-B-I quadrants and how they worked was another powerful concept.
Those are my favorite personal finance books. A wonderful book about business strategy is “Crossing the Chasm.” Great lessons about positioning your product or service to branch into new markets. I think it has applicability to your personal career growth, too.
Do you give to charity? Why or why not? If you do, what percent of time/money do you give?
We support an orphanage in Ghana. And we give to local animal shelters and the Red Cross.
I plan to give more once we’re past the SORR phase of retirement and any scarcity-mindset demons are banished.
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?
Our plans are to give each daughter half of our assets.
My real plan is to give most of it away while I’m around to enjoy seeing the difference it can make to children, grandchildren, and causes that we support.
That is a work in progress, and I’ve gotten many great ideas from the MMM community.
MI-400 says
Great story! Thanks for sharing. I too look forward to getting past the SORR risk. I have done a lot to mitigate that risk which I’ve talked about on MMM with a treasury ladder. In the short time I’ve been retired the market has done incredibly well.
Look forward to hearing more as you make the transition into the retirement club. No OMY syndrome!
MI-404 says
My reply got stuck below. Here it is for you, Mr. 400!
You know me too well, MI-400! OMY syndrome may be an issue, but for now I have several projects I want to complete prior to retiring – and we’re actively completing them. I’m still in the 2025 camp, although you know I started in the 2026 camp, then moved up to 2024, and now back to 2025. It’s a journey. 😉
And I do believe it’s better to overpad a bit than to fret about not having enough. See the above interview for my Scarcity Mindset issue. My wife agrees 100%. Ha!
MI-402 says
Your career journey really stood out to me. You had a wide variety of experiences! I bet it was stressful at the time, but you must have learned so much!
If you could do it all over again, do you prefer the variety of careers or would you prefer to stick it out in one field?
MI-404 says
What an interesting question! While it was stressful to start at ground zero in my thirties, and again in my forties, I really enjoyed the experience.
One thing I wish I had known about earlier is enterprise technology pre-sales careers. Early on, I detested selling, even when I had to sell for my small business to survive. I’d rather be sitting there writing code and building systems. Now I realize that the opportunities in sales are really unlimited, and if you truly believe in your company and its offering, it can be fun. And rewarding!
If you look at my salary history, it was only in the last five years or so that I started making really, really good money for my HCOL area. I could have done that earlier in my career and this might have been my “retirement” interview instead.
All in all, though, I wouldn’t change it. Each stage had ups, downs, and many memorable adventures. Thanks for reading!
Mary says
Loved this interview and your approach to enjoying your money while also sharing the wealth with family and good causes. Thanks for sharing!
MI-404 says
Thanks for the kind words, Mary! My wife is to blame for opening my mind and loosening the purse strings. She is a prodigious accumulator of projects, and I’m the bookkeeper. Ha!
I had a convo with my wife years ago about life, and she said that life is one journey where you should be in no hurry to arrive at the destination. Profound and pretty funny! Ever since then, I’ve seen time flying by and we are determined to add memorable experiences to every single year. It’s a stretch sometimes, but always worthwhile.
MI-404 says
You know me too well, MI-400! OMY syndrome may be an issue, but for now I have several projects I want to complete prior to retiring – and we’re actively completing them. I’m still in the 2025 camp, although you know I started in the 2026 camp, then moved up to 2024, and now back to 2025. It’s a journey. 😉
And I do believe it’s better to overpad a bit than to fret about not having enough. See the above interview for my Scarcity Mindset issue. My wife agrees 100%. Ha!
MI-349 says
What a great story, I enjoyed reading it! Thank you for sharing. Love your generosity – I donate to similar types of causes and know the difference they make is significant. I also think your targeted retirement age definitely qualifies as “early.”
MI-404 says
Thanks, MI-349! I’m not as generous as I would like to be, but I do enjoy how much good my US dollars can do in Ghana. A good friend of mine introduced me to the orphanage, and 100% of the funds go directly to the kids. You can’t beat that bang for the buck!
When I was younger, I wanted to be retirement-eligible by age 50. Well, life happened, and my new number looks to be age 57. Quite frankly, I’m happier now than I can remember ever being, so I’m in no hurry to rock the boat. I’m sure my dad would consider my retirement age young. My grandfather worked into his late 70s, my dad retired at 63 for medical reasons, and I want to leave the workforce on my own terms. I’m looking forward to seeing how it plays out.
Financial Fives says
You sound like a very fun person to be around, just from your writing! I like how you go against the grain on spending. Life is meant to be enjoyed and you never have tomorrow promised, so thanks for being a successful reminder of that.
I’ve always wondered about jobs with RSUs as a ticket to FI. Without being in IT, how would you recommend someone find the right role or company with those kinds of benefits?
MI-404 says
Thanks for the kind words, Fives! I am trying my best to have fun along the way. We have a big family vacation planned for next month (10 of us!), and my wife and I are currently thinking about booking a trip to Europe for just the two of us in September or October, but we won’t know for sure until August. So that is requiring a level of spontaneity that I’m not used to. Gotta exercise those different mental muscles from time to time!
MI-404 says
I forgot to answer the RSU question! RSUs are a staple of publicly traded companies, so any company listed on the stock exchange should offer employees restricted stock units (RSUs) as a component of overall compensation. It’s far more common in tech companies, I’m sure, due to the fact that you can pay less cash compensation (salary, bonus) and sprinkle in stock to round out the compensation.
If you’re looking specifically for stock, whether RSUs or options, I recommend applying to publicly traded companies and making sure they list it as part of their comp plans. ESPP is another nice perk. That’s where you can buy company stock at a discount at certain times. You have money withheld from your paycheck, then get a discount on the stock (typically a discount!) when you are cashed out of the ESPP and it converts to shares.
Best of luck!
M says
Interesting story—you’ve certainly done quite a lot! I have two questions for you:
First, as you look at your early years of retirement, which funds are you thinking of
tapping into to cash flow your expenses? Much of your assets are tied up in your
real estate investments and you are too young to tap into your retirement accounts
without hassle/penalty. Will you as a couple be tapping into your wife’s retirement
accounts?
Second, is maybe more personal. We have all heard about the “go-go”, “slow-go” and
“no-go” years. With the age difference between you and your wife, its likely that the
two of you will find yourselves physically in different time-periods. In fact, this may
be a reason to retire earlier…..but curious about how are you thinking about navigating this?
Enjoyed this interview and your candor. All the best to you both!
MI-404 says
Thanks, M! Sometimes it feels like I’ve done a lot, and other times it feels like not enough. I just *might* have one more “career” in me, this time related to personal finance. We shall see. On the advice of my MMM friends, I’m giving myself permission to postpone any decision on that until I’m out of the W-2 world for a bit. 🙂 Although I have started to research the educational requirements for a CFP and have located several prospective firms nearby. And have scheduled a meeting/lunch with a friend who’s in the biz. (Shhh!)
In terms of how to cashflow early retirement, you are correct. We will be taking mandatory RMDs from my wife’s IRAs the year she turns 73, which is next year. (gulp!) She also has mailbox money in the form of a pension and a decent Social Security check. We’re also actively paying off one of the rental property mortgages and are likely to stop paying any extra principle on the second one due to its great interest rate (3.25%!). That will free up a nice chunk for us to live on.
I have no plans to tap my retirement accounts early, but I’m not too far from 59.5 right now (another gulp!) and would be free to do so then. I think all my Roths have marinated long enough (5 years) and are also available then. I’m using New Retirement to model the withdrawals and a few Roth conversions along the way.
I did plan to sell a rental property if I started running low on more liquid accounts, but I hope to not do so. The low basis of those properties (one of which was a 1031 exchange already) will have Uncle Sam salivating. I plan to run that analysis soon, but the plan is to hold the rentals and live off the rental income with one paid off and the other one cashflowing pretty well.
Your question about the practicalities of an age difference like my wife’s and mine as we head to retirement is something I’ve been pondering for many, many, many years. Lucky for me, she is in AMAZING shape. We run together nearly every day, she eats healthier than I do, and she takes her health seriously. I really just try to keep up with her (and I’m not kidding!). It is a factor in me thinking about retirement more seriously now that she is 71, mainly due to my mom starting to have health issues at around 72-73. My mom went from go-go to slow-go to no-go in about two years, and it was really hard to see. You never know what’s in store, which is another reason to enjoy the journey! I take that seriously, and have overpadded my retirement travel budget accordingly. Right now the grandkids keep us both in pretty good shape, too. 🙂
In New Retirement, I am modeling my final age as 95 and my wife’s as 100, and I still end up with a decade alone at the end. Not fun to consider. But until one of us runs into issues, we’re planning a couple of great trips a year, fun with kids/grands, and enjoying every minute we have together!
MI-296 says
The irony of the enterprise software guy being “404” is pretty epic. Nicely done on that front:)
While I have gotten a sense of your style on MMM, this was a great interview. Ironically, in my house we have gone the opposite direction on Starbucks vs Kirkland.
I echo your statements about the variety of roles in Enterprise software. Pre-sales can be a lucrative niche for those who are technically oriented but still enjoy people and seeing the benefit of solutions being created and implemented.
Well done!
MI-404 says
Haha! Thanks, MI-296. I’m glad my MI is not “interview not found.” 🙂 Being able to snag 404 was incentive for me to finally get my interview written, especially after I learned that my MMM buddy got the 400 slot. Let’s see who ends up with 420. __ ~~
I am going to have to learn more about this Starbucks to Kirkland coffee conversion of yours. Maybe it’s time for a new MMM thread. I’m a big fan of Starbucks Sumatra blend, and I find it much less bitter than the Kirkland brand. Maybe my taste didn’t fully recover after my bought with COVID. 😉
Enterprise software has such amazing career opportunities that I really never considered until I got here! I work with technical marketing folks, product specialists, strategists, solution consultants, our partner ecosystem, and more every day. All of us are “in sales,” but the nuances of each role are different. Very interesting stuff!
MI 343 says
I appreciate you sharing your story!
MI-404 says
Thanks, MI-343! The adventure continues. One day I’ll be doing my retirement interview and that should be fun, too.
M372 says
Wow really enjoyed this one, many similarities to my work experience and scarcity mindset. We are close in age, really curious about your programming stack of choice when you were running the software company. I’ve been on the Microsoft Bandwagon for life, recently really enjoying Blazor versus javascript frameworks.
Also curious how you made the leap to the sales job. I suspect running your own company you wore multiple hats, sales being one of them, but still wonder how you landed a true sales job. Would appreciate any insight as to how to make that transition as I have often thought about it as well, if for nothing else just to sort of spice up the work life a bit before winding it down in a few years.
MI-404 says
I’m glad you enjoyed the interview, M372! When I was a programmer and financial analyst, I started out with SAS for data analysis. I was also a Lotus 1-2-3 macro wizard, with my crowning achievement being writing macros that wrote and executed macros. At my tech company, we had Microsoft servers and spent a FORTUNE (at the time) on a SQL Server. So we wrote MS-SQL, used ColdFusion to create the websites, along with lots of JavaScript. Once you could create custom tags in CF, we were off to the races and built what I thought was an impressive codebase at the time (early 2000s).
You are correct – when you own a small company, you do it all. I was doing sales then, but didn’t like the process much at the time. It was only when I started in real estate sales that I understood the value of scripts, objection handlers, and creating simple ways to describe complex processes. That has served me very, very well. I just jumped into the deep end of the pool with real estate. Frankly, it was either that or go get a “real” job where I have to commute to work, and I was too used to working from home. Now, of course, there are many more options, including the job I’m in now. I’m so fortunate to have this gig, even though I look forward to leaving it behind in the not-too-distant future.
If you’re in a technical role at a large company, you can see if they will give you a pathway to career change into sales. I have a friend at work who went from solution consulting to being an account executive, basically moving from technical presales to account sales. He said the learning curve was pretty steep, but he had support from his boss. That is a possibility for you, if you are in that type of company.
If not, you can always start at the beginning – find a more junior sales gig outside your current company. Sometimes you have to take a step back to be able to take several steps forward. It has certainly been the case for me and my career.
Best wishes to you and I’m happy to discuss more on the MMM. You can always DM me there.