Today I have an update for you from a previous millionaire interview.
I’m letting three years pass from the initial interviews to the updates, so if you’ve been interviewed, I’ll be in touch.
This update was submitted in August.
It’s an especially good (and detailed) update which I think you all will really appreciate.
As usual, my questions are in bold italics and their responses follow…
OVERVIEW
How old are you?
My wife and I are both 40 this year. I feel younger at almost 40 than I did at 30 and I’m in the best shape of my life.
Last time I wrote one of these, I told you that 50 was only 13 years away and that it felt far too close for comfort. It has not gotten any further away.
We’ve been together 21 years and married 14… It doesn’t seem possible.
Do you have kids?
Two kids. Our son is eight and our daughter is five.
It’s hard to believe we have a second-grader and a kindergartner.
I had always been pretty adamant and dogmatic about not paying for private school. Yet here we are spending about $30,000 a year for two kids in private school. (Strong beliefs held loosely! LOL)
Something else that changed since the last update: we set up a gift trust, a custodial account, and a Roth for each of the kids.
Our eight-year-old has a net worth of ~$130,000. So does our five-year-old.
My wife and I did not individually clear $100,000 until we were 28 — our combined net worth crossed $200,000 for the first time in March of 2015. Our kids beat us to six figures by two decades, and neither of them has any idea.
What area of the country do you live in (and urban or rural)?
Still sunny SoCal, still wine country, still on the same five acres.
The last time I wrote here, the property was mid-transformation. It’s finished now (as much as a house is ever finished… maybe better said, it’s finished for now). We set out to transform our property into a resort we never have to check out of.
We’ve planted a vineyard since my last update. We did that in March of 2025. Our family wine brand will be called STOIC, with the tagline of “Virtue in a Bottle.” Each bottle will feature one of the famous Stoics. Marcus Aurelius showed up on our first bottle, which was a white-label cab from Napa that we gave away as Christmas gifts at our annual Christmas party.
On the back of each bottle, we will have a STOIC virtue and how we reinforce that as a family value:
Patientia (Latin for patience) is the quiet force behind every great wine. Vines wait years for their first harvest, and the wine then rests in barrel until time has done its work. In our family we teach the same virtue to our kids: think in decades, not days, and remember that good things come to those who can delay gratification. This is STOIC — virtue in a bottle!
I love me a good double entendre. Wine is a patience game: it’s three years in the ground from when you plant the vines before you have fruit that you can harvest, and then there’s another two years minimum in the barrel before you have wine that’s worth drinking.
What was your original Millionaire Interview on ESI Money?
Before I made it to the double comma club, I was ESI Scale Interview #33 in October of 2018, with a net worth of $806,918.
Then, with much enthusiasm and excitement, I was Millionaire Interview #201, published September 2020, when our net worth was $1,911,820.
And most recently I was Millionaire Interview Update 48, published December 2023, with a net worth of $11,408,379.
This interview makes it four appearances across eight years, which makes this less an interview and more of a longitudinal study. The good news is everything has continued to trend up and to the right!
I’ve personally been documenting my story across my old blog and now Substack since 2014, and in that time I’ve grown my net worth from ~$200K to ~$14.2M.
Is there anything else we should know about you?
Last time, I told you the theme of my life was accelerating timelines — hitting milestones far sooner than I’d planned.
That theme finished its run (for now). In the last update, I was 37 years old with a $10M goal already beaten, a business sold, and a stack of things still scheduled to happen to me.
What do you do when the timeline runs out of things to accelerate?
(If you run on dopamine like the rest of us humans, you find new things to chase.)
I fully exited my company. Then I had to answer a question I hadn’t been in a position to ask yet — what do I do now that I can divorce my decisions from the dollars?
That question is what this update is actually about.
So there is real money news below, and I’ll give you the numbers in the detail you came for. But I’m even more excited to tell you all what I’m building next!
THE SCORECARD
In my last millionaire update, I made three predictions. Before I tell you how the last three years went, here is how those predictions did.
I nailed the first one, but in fairness, I wrote that last update at the end of September of 2023, so I had a pretty good idea of where my income was going to land. And I missed two projections because my timing was off on a single event (I didn’t think we’d have a liquidity event until 2026, but it came a year early).
Again, the recurring theme in my life is accelerating timelines. I may not get the timing or the exact number right, but I believe a planned life is a higher-probability path to a prosperous life.
NET WORTH
What is your current net worth and how is that different than your original interview?
- September 2023 (last update): $11,408,379
- July 31, 2026: $14,230,354
That’s +$2,821,975, or +24.7%, since the last update.
Debt: none. No mortgage, and we pay the credit cards in full every month.
⚠️ But the 24.7% is not the interesting number.
The interesting number is that for the last ~12 years I’ve been able to compound my net worth at a rate of 45.75%.
Twelve years ago, the number it was compounding from was ~$200,000. That is the entire story of these four interviews in one line. (Mind Blown 🤯)
What happened along the way to make these changes?
Last time, I left you with a cliffhanger. I’d rolled $2,500,000 of my proceeds into the acquiring company’s stock instead of taking cash, and I told you I expected it to be worth “$7,500,000 to $15,000,000 by 2026, which also corresponds to an anticipated liquidity event.”
It is now 2026. Here’s what happened.
On April 1st, 2025, a top-tier global private equity firm bought out our prior sponsor. I handed in my required two-year notice the same day the wire hit my account. Nine months later, on December 31st, 2025, I fully exited (after successfully negotiating an early release from my notice period) — six years and eleven months after I formed the company with $267.42.
The $2,500,000 roll became $6,442,653. (Excludes my salary, bonus, and distributions received during the same period.)
Across the full cycle — salary, bonuses, profit distributions, three liquidity events, and the final equity — I personally extracted $14,379,237 from a business I started with $267.42 and never put another dollar in (it was completely self-funded after that).
Four things I want to say about that number, because a number like that gets misread.
- The gain was on paper for a long time, and paper is not money. For the last few years I’ve carried a growing seven-figure position in a private company I no longer controlled, subject to somebody else’s exit timing. I got very comfortable saying “we’re worth X” while knowing that X had a wide error bar and no liquidity.
- A large part of that number is still not in my hands. Of the $6,442,653, less than half came to me in cash. The remaining $4,000,000 is a note, and $200,000 of it is tied to an earn-out. The note pays out on the earlier of its five-year anniversary date or the next change of control: another private equity firm, a strategic buyer, or an IPO. So when you see “$6.4 million,” understand that a meaningful chunk of it is a promise with a date range attached. That is what an exit actually looks like. It is not always a wire transfer right away.
- The government got paid. I’m not going to publish the tax bill in this post — but I’ll say that it was substantially less than most people would guess for a liquidity event in the multiple seven figures. That gap isn’t luck, and it isn’t a loophole; it’s the product of a decade of obsessive, proactive tax planning and strategy. I’ve been writing that up in detail in my tax-strategy series on Substack.
- Rolling equity forward (and trading up for a larger compounding machine) is the single highest-leverage financial decision I have ever made. I was trading a big slice of a small pie for a small slice of a much larger one — and then letting a much better-capitalized machine compound on my behalf. You concentrate to build wealth. You diversify to preserve it. I was still in the building phase, and Charlie Munger would remind us:
Don’t interrupt compounding unnecessarily.
There’s one more thing, and it changed the shape of everything after it. My exit came with a five-year non-compete, scaled to the value of the proceeds I received. Before I started any of what I’m building now, I had consulting engagements lined up — $40,000 a month for about twenty hours a week, plus equity I’d estimate would have been worth $5,000,000 or more, plus performance comp on top of that. I deliberately structured all of it to comply with the non-compete.
The firm turned them down anyway.
It stung.
It was also the best thing anybody did for me this year. The twenty hours a week those contracts would have consumed are exactly the time I’ve spent going deep on what I think is the opportunity of a lifetime:
AI is the first technology I’ve seen that converts consumers into creators — it unlocks human potential — and I have never been more optimistic about the future because of it.
The $40,000 a month was real money. The attention turned out to be worth more.
What are you currently doing to maintain/grow your net worth?
Four things now, where last time there were two.
- Investing the proceeds. I’ve had liquidity events every year since 2021, when I sold the first 60% of my company. Those events have converted a concentrated private position into liquid capital, and the job has been and continues to be to deploy, grow, and preserve that wealth.
- Operating one small business that actually earns. A food brand — Born Chef, which started as an empanada business, added calzones, and has a restaurant on the way — pacing for ~$30,000 a month in revenue at robust double-digit net margins. I’ve got two chef partners, and I’m building everything that supports and automates the business with AI.
- Family wine brand — STOIC. Touched on that above. What I didn’t mention is that we also have a mission bottle in honor of my mother-in-law — it’s called “Ducks in a Row.” A portion of every bottle sold goes to support Hospice of the Valley, which serves Temecula Valley families and never asks the family to cover the cost of that care. Not a dollar. Whatever a family can or cannot pay is simply not part of the conversation. My wife sits on the board as well.
- Building software, which so far has earned nothing. This is the honest part, and it’s the whole next section. In fairness, I have only been building and shipping for the last three months and only recently launched two products into beta. That said, we have used AI to save about $20,000 on about $1,350 of AI spend so far in 2026.
EARN
What is your job?
I don’t have one… at least not in the traditional sense.
I’m supposedly retired as of December 31st, 2025. I’ve been referring to this chapter as my “first retirement.”
The big difference now is that I don’t have to work anymore if I don’t want to, but I’m a builder!
So I have self-proclaimed the title of Chief Opportunity Officer.
That’s the literal answer. The useful answer is that I’ve spent the last eight months on a one-person conglomerate — a portfolio of small, high-margin businesses run by one human with AI doing the work that used to require a team. The first five months were research, planning and ideation. I started building on May 7th.
The target I’ve written down is $10,000,000+ of revenue at $5,000,000 of profit — 50% blended net margin across the portfolio and an 80–90% net margin target for digital products, with a headcount of one (it’s what I call the new three-person company: me, myself, and AI).
The food brand (Born Chef) is an obvious exception to the rule, but I’m still building it to be AI native and highly profitable.
And the family wine brand (STOIC) is more of a passion project and for a good cause.
Most of it runs through one holding entity.
Here is a list of some of the things I’m building in my AI Factory:
- The food brand — earning. The only line in the portfolio that produces cash.
- A personal-finance platform — finished, in a closed beta with 50 real households.
- A Mac screen-capture app — finished, shipped, 125+ downloads so far.
- A multi-entity accounting system I built for myself — it replaced four QuickBooks subscriptions and runs our books for three separate entities (saving $2,000 per year).
What is your annual income?
It’s projected to be down substantially in 2026, but here is my full history back to 2005.
- 2025: $3,201,945 — the exit year
- 2026 projected: $450,000–$600,000
Now the part that matters more than the totals — the composition:
In 2023, 90% of our income was active, and 10% was passive. So far in 2026, 12% is active, and 88% is passive. Active income fell from $1,764,192 to $35,236.
I didn’t gradually wind down. It walked right off the cliff.
How has this changed since your last interview?
The bi-weekly paychecks and quarterly profit distributions stopped. So did the annual liquidity events. But we had been preparing for this as we built up our passive income, and we were/are prepared to cover any shortfalls from our balance sheet.
The number that keeps me sane is the same one Update 48 leaned on, refreshed: only about $100,000 of our spending is fixed and necessary (no debt, and the rest of our spending is all discretionary). When your fixed obligations are so small relative to your assets, a zero-income year is a choice, not a crisis.
Have you added, grown, or lost any additional sources of income besides your career?
Forty.
We currently track 40 active income sources, and only three of them are new this year: Born Chef, one coaching client, and the paid portion of my Substack.
Which is the point. Our income went 88% passive in the same year my active income fell to $35,236, and almost nothing new had to show up for that to happen. The sources were already there. They were built over the last decade, back when I had a paycheck to build them with.
SAVE
What is your annual spending and how has it changed since your interview?
Last time I gave you “regular” spending, with the house projects carved out. This time you get the all-in number instead — every lifestyle dollar we spent, taxes excluded, straight out of the ledger:
- 2023: $502,798
- 2024: $493,609
- 2025: $501,260
- 2026 forecast: $334,269
Three straight years within $7,000 of half a million dollars. We had major expenses related to home-improvement projects in each year from 2021 through 2025.
2026 is the first year with minimal home-improvement spend (~$20,000), and the forecast says $334,269.
I mentioned above that only about $100,000 of this is fixed and necessary. Here’s the part I didn’t say: the rest is entirely discretionary — which is to say, entirely avoidable.
For context on the trend: fixed-and-necessary was about $60,000 in 2016 and $80,000 in 2023. We have added a five-acre property, a second child, and a decade of lifestyle to that base, and it has still barely moved. That is not an accident. It’s the thing we’ve been most disciplined about… avoid fixed expenses and maximize for optionality and flexibility!
A few lines worth naming:
- The house. Between buying it and finishing it, we’ve put $1,600,000 of cash into the property across 2021–2025. By an enormous margin, it’s the largest thing we’ve done with the proceeds. It’s also done! (for now 😂)
- Childcare: $32,042 forecast this year, down from $90,000 in 2022. Private school is cheaper than a full-time nanny plus daycare.
And one that isn’t really a line item.
The memory-making budget. Starting in 2024, we set aside up to $100,000 a year, allocated purely to making memories. Not travel exactly. Not entertainment exactly. Memories.
It is my favorite money to spend — and the reason why is at the very bottom of this post.
Other than the house and the memory budget, we continue to spend significantly less than we could.
I still preach the law of 50/50 — save half of after-tax income, spend the other half guilt-free. But when the income stops, a savings rate stops being a useful number. You can’t save a percentage of nothing.
So here’s the one that replaced it: burn against the portfolio. What percentage of our net worth do we consume in a year?
2.3%. $334,269 of forecast spend against $14,230,354 of net worth.
That’s what I watch now, paired with liquid net worth and passive income. If you’re anywhere near the end of your earning years, start tracking it today. It answers a question a savings rate can’t.
What happened along the way to make these changes?
The house is finished, so the one-time spending that dominated 2020–2023 has fallen off. Childcare is falling. Travel is rising to meet it, deliberately — the kids are at the exact age where they’ll still come with us and still think we’re cool, and that window has a hard close date.
The other change is that spending decisions now come out of a pile instead of a paycheck.
Same dollars, completely different psychology.
When you’re earning, spending feels like a percentage. When you’re not, every purchase feels like a full withdrawal.
ADDED QUESTION — What happened to health insurance when you walked away from the paycheck?
$22,560 a year for a family of four, on a high-deductible PPO through Blue Cross Blue Shield. And the part nobody believes: that’s about 40% less than I was paying for nearly identical coverage inside the firm that bought mine. I kick myself when I realize that I could have been paying less two years earlier.
INVEST
What are your current investments and how have they changed over the years?
The direction of travel since the last update is one word: simpler. I’ve been on a mission to simplify the financial web I created and significantly reduce the number of K-1s and 1099s we receive (started this in 2023, and we are down to 40 annual K-1s and 1099s related to private investments).
Last time we were 28% liquid and 72% illiquid, with a stated goal of 50/50. Today we’re 41% liquid, 59% illiquid.
Our standing rule since 2023 has been no new private/illiquid investments until we are at least 50% liquid. And all new and returned capital is deployed into liquid investments. As we approach 50%, I’m already mentally leaning toward increasing that to 75%. The one exception is if it’s a business we are an operator in, like the Born Chef food brand I bought into (I’m a 33% owner).
The breakdown, as of this year (snapshot is past the July 31st cutoff, so NW is slightly higher):
Once the $4,000,000 note pays, and holding everything else constant, that should put us near 70% liquid — unless one of the private positions or one of the businesses I’m building goes parabolic, which would be a good problem to have.
Bitcoin: I’m out of the direct position. I held roughly 8 BTC at a net basis of about $29,000 after years of selling calls and puts against it. That’s closed (at a nice profit). My only crypto exposure now is through the iShares Bitcoin ETF (IBIT), and I’ve sold short puts against it — which is the same thing I was doing with the coins: getting paid to hold a view, and agreeing to buy more if it comes to me at a price I like.
And the part I’d rather skip: two of my investments died in 2025, and I didn’t get a vote on either one.
In July 2021, I put $50,000 into Bowery Farming, a vertical-farming company I believed in. It went bankrupt. The equity went to zero.
Around the same time, I had $250,000 in a real-estate debt fund playing in San Francisco’s ultra-luxury market. For fourteen years it paid its 8% and never missed. Then the market turned, it stopped distributing in March 2024, and it liquidated down to a fraction of what I’d put in — a realized loss of $136,525.
So in 2025 I harvested both: $186,525 in realized capital losses, landed against gains, which saved roughly $69,200 in tax at my California long-term rate.
You don’t have to make it back the way you lost it.
What happened along the way to make these changes?
The concentrated bet is over. That changes everything about how I allocate.
For the seven years prior to 2026, 90% of our net worth growth came from one asset.
I said it earlier in this interview and I’ll say it again: you concentrate to build wealth, you diversify to preserve it.
I was concentrating.
Now I’m preserving, and preserving is a very different sport — it’s boring on purpose, with most new investment going into a personalized direct-indexing strategy (vs. a standard ETF to capitalize on tax-loss harvesting).
ADDED QUESTION — How do you keep track of all of this?
(Adding this one because it’s the question I get asked most often, and because the answer is the most interesting thing that happened to me since the last update.)
For over a decade now, I have pulled together a detailed financial report every single month. Like many of you reading this, I did this in Excel.
Over time, my financial life grew in size and complexity. My Excel workbook ballooned to 76 sheets and was supplemented by personal-finance apps for plumbing (data aggregation), while Excel remained in place for manipulation and presentation, but even it was falling short.
The apps never learned what actually moves the needle: tax planning, the savings rate treated like the lever it is, the true cost of every position. So when I finished selling my company, I built the tool I couldn’t buy at any price.
The machine had outgrown itself, and regardless of complexity, I felt every personal-finance tool missed the mark. I was tired of half-solutions, and I needed more than a data aggregator and more than a spreadsheet to manage the balance sheet, cash flow, plan versus actual, tax planning, private investments, and the true cost of every position net of every dividend and premium it ever paid me.
My entire career was building enterprise Financial Planning & Analysis (FP&A) systems — the budgeting, forecasting, and variance machinery big companies run on. So after I exited, I built the household version: Ledger of Life. One encrypted book per household. Balance sheet, cash flow, plan versus actual, income by source, private deals and public markets in the same view.
Every number in this interview came out of it. The net worth figure, the allocation table, the income series, the 40 income sources, even the fact that my liquid/illiquid split is 41/59.
It’s in a closed beta with 50 households, and I built it because I needed it. And then I decided to make it available to others. (It’s US and Canada only for now — that’s as far as the bank and brokerage connections reach.)
MISCELLANEOUS
What other financial challenges or opportunities have you faced since your last interview?
The opportunity: AI actually changed everything. In roughly three months, I built eight things that would previously have required a team and a funding round. At last estimate, I’ve spent 500 hours, and the human-labor equivalent from my AI team is 7,200 hours.
Across the various human roles:
If you are a competent operator sitting on domain expertise, the cost of turning that expertise into a product just fell through the floor.
And almost nobody is taking advantage of it. Less than 1%, by my estimate. More than half the people on this planet have not interacted with an LLM even ONE time.
If you’re reading this, you already have the two things that matter: you know something valuable, and you’re willing to learn a new tool. The barrier stopped being the technology about two years ago.
ADDED QUESTION — What’s actually been hard about “retiring” at 39?
I call it my first retirement, and the phrase is doing real work in that sentence. I never intended to retire in the traditional sense. This was leaving corporate America for the second time — I left once to start my own firm, sold it as planned, and ended up back inside a billion-dollar company. I’ve described myself my whole career as a square peg trying to fit through a round hole. I knew that chapter couldn’t last; I gave myself up to five years, and I hit the ejection button at about four.
The hard part surprised me: it wasn’t the money and it wasn’t purpose.
It was being left out of the team I’d been so heavily involved with. A company that goes from $300 million to a billion in three years — 27 acquisitions in 36 months — is chaos. I was in the middle of it, and then one morning I wasn’t.
It got easier. And untangling it taught me the one thing I’d say to anybody walking out of a company they built:
I don’t miss the company. I miss the team.
Those are different things, and it took me months to tell them apart.
The identity question everyone warns you about mostly answered itself: I’m a builder. That’s what I was underneath the titles all along — that, and being a conduit of opportunity for other people. Sending the elevator back down. Being someone’s first believer. I run on the idea that belief is capital that compounds, and that the goal is to create more value than you extract.
The difference now is that nobody’s permission is required. My filter is simple — a pain, a problem, or a passion — and when someone asks what I’m up to, I can run down the list for five minutes and there is nothing on it that isn’t building. I even moved my office into the home gym, all 500 square feet of it. The joke in our house is that I had to leave employment to finally get the corner office.
So here is what’s actually hard, one year in: the discipline problem inverted. I see so much opportunity in what AI makes possible that the risk is no longer running out of things to do — it’s a one-dimensional life.
I set guardrails when I left: I work 9:00 to 3:00, and the rest belongs to my wife and kids. I’ve mostly held them — except the last six weeks or so, when launches pulled me back into sprint mode. There’s an ebb and flow to building, and I accept that, in sprints of four, five, six weeks — not as a lifestyle. But I can get obsessed when I’m building, and my wife would tell you the sprints are real.
Because the math on the other side is brutal and simple: the kids are only going to be five and eight once (as my close friend Paul would remind me: you only get 18 summers and 18 Christmases). I want them to see me build, and I want them to see a great husband, father, friend, and athlete at the same time — proof that a multi-dimensional life is possible.
That you can have it all. Maybe just not all at once in the beginning. But certainly over time.
Overall, what’s better and what’s worse since your last interview?
Better:
Time. I control 100% of my calendar for the first time in my adult life, and it is exactly as good as I hoped. My kids are eight and five, and I am there — not “present,” actually there — at school drop-off and pickup, their sports practices, school events, etc.
“F*ck you money” is still real and it is still the best purchase I’ve made. Every decision I make now is divorced from whether I need the money, and I don’t think you can appreciate the weight of that until it’s gone.
And the building is fun again. Nobody’s approval to get, no P&L to defend, no BS meetings.
I’ve believed that it has been the best time to be alive since I graduated high school, and that belief has only strengthened over time. As Peter Diamandis would say:
The only day better than today is tomorrow.
The future is filled with opportunity not just for my household but for the rest of humanity. I truly believe that.
Worse:
I can’t think of anything that’s gotten worse. To be honest, my personal philosophy is that life skews positive up and to the right over time.
What are your plans for the future?
Financially: keep marching to 50/50 liquid/illiquid, then reassess. Every new dollar goes liquid. No new private commitments until we get there — and the note, when it pays, does most of the work.
We said last time we didn’t intend to move the goalpost. Then in 2024 I wrote a post literally titled “Moving the Goalpost from $10M to $25M” — so let me be precise about what actually moved, because it isn’t what it looks like.
The goal didn’t move. The forecast did.
$25,000,000 is a target I’m not pursuing. At $14,230,354, compounding alone makes it close to inevitable inside 5–10 years, before counting any X-factor from the things I’m building.
Extrapolate further, and I don’t think $50–100 million is out of the question in my lifetime. But those are projections, not goals — I’m not pursuing them the same way I did to get to my original $10M goal.
The number I actually manage is spend. For the first five years after active income — starting in 2026 — we set the budget around $300,000 a year (you can see above we’re already forecast to run a little over it). Deliberately conservative: partly to mitigate sequence-of-returns risk, partly because retiring before 40 means underwriting this lifestyle for another sixty years — my goal is to live to 100 or older.
The moment I’m comfortable — the liquid side compounding, passive income layering in — I’ll take it to $400,000 or $500,000 without ceremony. Raising that number is the only goalpost I care about.
The real plan isn’t a net worth number. It’s the one-person conglomerate: eight figures of revenue at a ~90% margin with a headcount of one. Not because we need the money. Because I want to find out whether it’s possible, and because the tools to try only started existing about two years ago.
I’m writing the whole thing down as it happens, wins and misses — the same way I published all my financial details and goals when I had no idea whether the plan would work. It didn’t feel like content at the time. It felt like accountability. It still does.
And we travel. Next up is Italy; we leave September 30th for three weeks. Flights and accommodations are booked. We indulged and got lie-flat business-class seats for the long flight from California.
Given that you have a bit more wisdom and experience, what advice do you have these days for ESI Money readers?
The golden rule hasn’t changed, and it never will: spend less than you earn and invest the difference wisely. The bigger the gap between earning and spending, the more powerful compounding becomes. It’s not rocket science.
But I’ve now said that in all three of these interviews, so let me add the three things this cycle taught me.
- Keep your fixed costs embarrassingly low. Ours went from about $60,000 in 2016 to about $100,000 today, and in between we added five acres, a second kid and a decade of lifestyle. That gap is the entire reason a zero-income year is a choice and not a crisis.
- Concentrate to build, diversify to preserve — and know which one you’re doing. I rolled $2,500,000 forward instead of taking the cash because I was still building. If I’d been preserving, the exact same move would have been a bad decision. Same trade, opposite answer, and the only variable is which phase you’re in.
- You don’t have to make it back the way you lost it. Two of my investments died and I didn’t get a vote on either one. The losses still went to work for me at tax time.
And one that isn’t a money rule at all: the grandest allocation problem in your life isn’t financial. It’s time. Money is the renewable currency. Time is the one you’re forced to spend down to zero, and nobody mails you a statement.
So here’s my question back to you: you almost certainly know your savings rate. Do you know your time allocation with anything close to that precision?
P.S. I should expand briefly on the fact that Ledger of Life is more than a personal-finance application. It’s a holistic system to manage the three major accounts.
You get one life. One ledger. Three accounts (sub-ledgers) fund it: Money. Health. Time.
The caveat: these are early v1s. Opt-in, off by default, and deliberately behind the Money sub-ledger. Money had a decade of spreadsheet reps behind it before I wrote a line of code — these two are earning their reps now. The Money sub-ledger launches first, but Time and Health become available in beta at launch.
Why build them at all? Because these pages are my first swing at giving that problem a ledger.
The Time ledger opens with a Memento Mori chart: one box for every month of a life. When a month ends, you fill its box in. Same close, different currency.
“One box for every month of a life — the only ledger you close by filling it in.”
“The fortune arrives 86,400 seconds at a time. This is the statement.”
One detail for the systems people: when both ledgers are on, the sleep tax on that second screen isn’t an assumption — it’s priced off my actual last 90 nights of sleep, pulled from the Health ledger. The books talk to each other.
The Health ledger is the earliest of the three. Apple Health export in, dashboards out — sleep, steps, recovery, body. No coaching, no streaks, no badges. A ledger. That’s deliberate ordering, not a philosophy against guidance: the intelligence layer comes to all three currencies later — first the books beneath it have to be true.
“The third currency gets the bank-data treatment: import, reconcile, trend.”
“Sleep is a third of the fortune, so it gets its own page.”
One more, because a ledger of months would be bleak if the months were empty. Every box on the chart can hold its memories, moments, and milestones — that’s me trying to bring the memory-dividends idea from Die With Zero to life, a book that shaped a lot of my thinking. The trip pays once; the memory pays every time you open the box. This is why the Time ledger exists at all:
“Memory dividends, on deposit — a birth, a milestone, a family trip.”
That’s the memory-making budget from the SAVE section, turned into a balance sheet. It’s why I stopped feeling strange about spending six figures a year on things you can’t resell.
You get one life. One ledger. Spend it on purpose.
Onward & Upward!
