Broke Again At 49, And This Time There Is No House To Blame

After stretching for the nicest house I could barely afford in 2023, I ended up living paycheck to paycheck for six months. It was stressful enough that I picked up a part-time consulting gig to shore up liquidity. Thankfully, stocks and real estate kept rebounding after a rough 2022, and the broke feeling faded.

I promised myself I would never feel that way again.

Three years later to the dot, I am broke again. And this time I cannot blame a house.

A Severe Miscalculation In The Capital Call Timeline

Earlier this year I wrote about the difficulty of investing in traditional venture capital as you get older. These funds take 10 to 12 years to return capital. Commit today and I am 59 to 61 before I see the money come back.

Which is exactly why I see the next five years as my last hurrah for aggressive venture investing. After that, the math stops working on a human timeline.

So in March 2026, I asked the general partner of a top venture capital firm if I could invest in their new AI fund. He graciously said yes. I asked the operations person handling my onboarding how much I could invest, and she told me anywhere between $100,000 and $1 million.

As a San Francisco resident since 2001, I feel every new tech advancement viscerally. I have also become an AI maximalist who wants to own the very technology that may disrupt my children's futures, potentially for the worse.

So I committed the maximum: $1 million. Go big or go home has been my ideology since 1999, when I first joined Wall Street.

My invitation to their previous fund in 2024 had gotten lost in the mail. Opportunities like this do not come around often. Better to say yes and figure out the details later, I told myself.

There Was Just One Big Problem

I did not have $1 million liquid. Not even close as dual unemployed parents who make a pittance as an author and substitute pre-school teacher.

But I have been a limited partner in traditional venture funds for over 15 years, so I made what felt like a reasonable modeling assumption. The fund would call roughly 20% – 30% of committed capital in year one, 20% to 30% in year two, another 20% to 30% in year three, and the remainder across years four and five.

That math gave me a budget I thought I could handle.

YearWhat I BudgetedWhat Actually Happened
2026$200,000 – $300,000$460,000 and counting
2027$200,000 – $300,000?
2028$200,000 – $300,000?
2029 – 2030$50,000 – $200,000?

Six months into the fund's closing, a whopping 46% of committed capital has already been called. And there are still several months left in the year.

I am now tapped out. I cannot meet another capital call without selling existing assets and paying capital gains tax. Let’s hope the fund takes a breather for at least a month.

Why Being Forced To Sell Feels Like Losing

This is a bigger problem than it looks on a spreadsheet.

My investment philosophy for the past 14 years post FIRE has been to buy and hold forever and minimize taxes. Selling one asset to fund another asset is not wealth creation. It is wealth transfer, minus a 20% long-term capital gains haircut, plus the 3.8% net investment income tax, plus California state tax.

In my bracket, including State, that is roughly a 33% toll on every dollar of gain I am forced to liquidate. What a waste of money.

I would rather grow my net worth by adding new capital, not by shuffling it from one pocket to another and handing the government a tip along the way.

I'm also not blameless here. I have mismanaged capital calls before, most memorably when I missed a $20,000 call because it got buried in my inbox. I wrote an entire post about how to manage capital calls better going forward.

Do VC Funds Have Covenants That Limit Capital Calls?

This is the question I should have asked in March. So let me answer it for you now, since almost nobody explains it before you decide to invest in traditional venture capital.

Hard annual caps are rare. In most limited partnership agreements, the General Partner (GP) has broad discretion to call capital whenever an investment opportunity appears. That is the entire point of a blind pool. You are paying them to move fast when a hot company opens an allocation, and a covenant that says “no more than 25% per year” would kneecap them in exactly the moments you want them aggressive.

What the Limited Partnership Agreement (LPA) does contain, and what you should actually read:

Investment period

Usually three to five years. The GP can only call capital for new investments during this window. After it closes, they can still call for follow-ons, management fees, and fund expenses. This is your real outer boundary, not a pacing schedule.

Notice period

Typically 10 business days, sometimes 10 calendar days. That is all the warning you get before having to wire the funds after a capital call. Know this number cold, because it defines how fast you need to produce cash.

Recycling provisions 

This is the one that catches people. Many LPAs let the GP redeploy early proceeds instead of sending them to you, or distribute them and recall them later. So your total wires can exceed 100% of your commitment, usually capped at 110% to 125%.

Here is why it exists. Management fees and fund expenses eat roughly 20 cents of every committed dollar over a ten-year fund. On my $1 million, that is $150,000 to $200,000 that never reaches a startup. Which means the portfolio has to return about 1.25x just to get me back to even. Recycling fixes that math by putting early exit proceeds back to work, so a full dollar of my capital is actually invested.

The GP has a second motive, of course. More invested capital means more total gains, a bigger carry pool, and better interim marks to show the next set of LPs. Both things are true at the same time.

The part that hurts is unpredictability. A distribution you already mentally spent can get recalled. Worse, you can owe capital gains tax on a gain whose cash is no longer sitting in your account.

Management fees on committed capital. 

Roughly 2% per year on the full $1 million, whether or not a dollar has been deployed. On a ten-year fund, that is another $150,000 to $200,000 of calls that have nothing to do with investing.

Side letters and Most Favored Nation (MFN) clauses

If you want pacing protection, this is where it would live, and it is generally reserved for anchor LPs writing eight-figure checks. A most-favored-nations clause lets you see and opt into terms given to other investors. Worth asking about even if you assume the answer is no.

One more wrinkle that explains bunched-up calls: many funds now use a subscription credit line. The GP borrows against LP commitments to close deals instantly, then calls capital later to repay the facility. This does not increase how much capital gets called, but it changes the shape of the calls.

Instead of a steady drip of smaller wires, you get fewer and much larger ones, arriving with less correlation to actual deal timing. The borrowing cost usually sits below the fund's preferred return, so it generally works in your favor during the J-curve. But if you are modeling smooth quarterly drawdowns, a sub line will throw off your cash planning.

The five questions to ask before you sign to become an LP

  1. What is your expected deployment pace by year, and what did your last two funds actually do?
  2. What is the notice period on a capital call?
  3. Do you use a subscription credit facility, and how does that affect call timing?
  4. What is the recycling cap as a percentage of commitment?
  5. What are the remedies if an LP misses a call?

Ask these over email so you have it in writing. A good operations manager will answer all five in a paragraph. A GP who gets annoyed by the questions has told you something useful too.

The problem is, if you're trying to gain access to a tier 1 VC firm, you want to come across as frictionless as possible. Therefore, read your onboarding docs carefully. They should answer most, if not all of these questions.

What Happens If You Miss A Capital Call

There is no version of me missing these calls, and here is why.

Default provisions in most LPAs are designed to be onerous. Depending on the fund, a defaulting LP can face interest charges on the unpaid amount, forfeiture of a meaningful chunk of their capital account, forced sale of their interest at a discount, and loss of all future participation in the fund.

But the financial penalty is not the real deterrent. The real deterrent is that venture is a small world. Default once and you are not getting invited into back to future funds. The invitation is the scarce asset, not the capital.

So I will meet every call. The only question is where the money comes from.

Four Main Ways Out

Not all is lost. I have a windfall sitting in my VCX position from 2023 to 2026, and the lockup is now over. But I do not want to sell shares right before the main event, which is the Anthropic IPO. Instead, I'm buying into weakness. Further, I already sold all my unrestricted shares, which means I already have a large capital gains tax bill coming due.

That leaves four doors:

A bridge loan from the Bank of Mom and Dad. Available, humbling, and a strange thing to contemplate at 49 years old. That said, I consulted with my dad before committing the $1 million, and he did mention he has spare funds in case I run out of money. This route will be the last resort.

Earn more online. More personal finance consulting sessions, more business development on Financial Samurai, more book work. Active income to cover a passive income shortfall. But since I started FS in 2009, I've always wanted to treat this site as fun first. Focusing too much on business bums me out.

Go back to work part-time. After going to the last YC Demo day, there are plenty of fantastic startups to help. San Francisco is in a boom loop with a ton of demand for people who understand distribution, marketing, and AI. But commuting to work and sitting in on lots of meetings aren't great, so work-from-home would be preferred.

Create a pledged asset line, sometimes called a Pledged Asset Line (PAL) or Line of Advance (LAL). I pledge a taxable brokerage account as collateral and draw against it when a call arrives, typically at SOFR plus 1.5% to 3%. No sale, no capital gains tax, no scramble. You repay when distributions land. Renting money at 7% to avoid a 33% tax hit on embedded gains makes sense. I didn't think of this until a reader mentioned it.

So far I have mis-budgeted by at least $160,000. By the time the year is done, the miss could be over $200,000 given how quickly AI companies are growing. The problem with a PA/LAL is that taking on new debt when FIRE is a non-starter. It's like going backwards, pushing you back towards the work cage.

The Desire To Be Challenged

I have to be frank. Committing capital I did not have was not entirely by accident. Part of me wanted the challenge of producing $1 million I did not have.

Being FIRE since 2012 has mostly been smooth sailing, thanks to an unrelenting bull market. There was 2018, a terrifying few weeks in March 2020, and a down 2022. Otherwise things have generally been good.

Smooth is wonderful for about three years. After that it starts to feel like being a boat in a harbor. Safe, maintained, going nowhere. Boring. It also feels a little too lucky, like being born on third base, which feels unfulfilling.

The 2023 house purchase was the last time I felt real financial pressure. Stressful, no question. Also exhilarating. It forced me into the part-time consulting gig, which paid well, taught me things, and introduced me to new people full of hope.

I came out wealthier and with better stories than if I had never stretched. The financial pressure pushed me out of my comfort zone, which I appreciate. This challenge is what I long for every few years. Because there's no better feeling than doing hard things and succeeding.

Manufacturing Scarcity To Create More Motivation

Manufactured scarcity is a hell of a forcing function. With no deadline and no consequence, I write a little slower, wake up a little later, grow my belly a little larger, and let good ideas sit in a draft folder for a year. It is far too easy to slack off in America, the home of abundance.

With a wire due in 10 business days, everything sharpens. I return emails the same day. I stop treating my site like a hobby that happens to make money.

Even my calendar in the morning gets looked at instead of ignored. And time with my children gets more precious, because there is less of it when work is actually pulling at me.

There is a line in that old Goo Goo Dolls song about bleeding just to know you are still alive. That is manufactured scarcity. After 14 years of financial independence, the edges go dull. A capital call is a cheap way to sharpen them.

Something may be slightly broken about me. But I would rather feel alive and mildly panicked than comfortable and slowly fading.

Just be careful. This only works if the downside is survivable. Take the challenge in a size you can afford to lose.

A Small Piece Of Good News

Just as I was finishing this post, I got an email from a venture debt fund where I am an LP. It is sending a distribution of over $11,200. This is on top of about $4,600 a week earlier.

Nearly $16,000 against a $160,000 shortfall is not a rescue. But it is the first good news of the quarter, and I will take it. Perhaps more distributions are forthcoming as well.

Time to survive the next six months and grind!

Readers, have you ever committed to something before you had the money, and then made it work? Do you find financial pressure motivating or purely destructive? And for fellow LPs, what is the fastest your fund has ever called capital?

Track Your Money Before The Wire Comes Due

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45 Comments
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Kirk
Kirk
10 days ago

Sam,
I understand your frustration, but wonder why on a few things.
 
Why Being Forced To Sell Feels Like Losing
Selling one asset to fund another asset is not wealth creation. It is wealth transfer, minus a 20% long-term capital gains haircut, plus the 3.8% net investment income tax, plus California state tax.

I know Warren Buffett is a fan of Buy and Hold, ride the turmoil and you’ll do great. However, under our current Administration, I don’t feel that is true any longer. I do a fair amount of buy/sell typically within a few weeks to a few months. This year has been quite profitable and I have substantial gains.

However, that is all offset due to having an account managed via a Financial Planner >> Tax Loss Harvesting. The losses on paper are greater than my gains! End result, hopefully, is to pay very little in Cap Gains. Something to consider, especially with your Financial background?

ASH01
ASH01
9 days ago
Reply to  Kirk

And isn’t LT capital gains 15% (plus the 3.8% if taxable income exceeds certain threshold)? Why starting at 20%?

Randy Pulliam
Randy Pulliam
9 days ago
Reply to  ASH01

When your AGI hits $613,000 (married) LT capital gains become 20%.

Frank
Frank
1 day ago

Sam, You do not have to make this public Regarding your question. %0 investments in Venture Capital Retired seven years go at age 53. Sold the education company my wife and I created and ran for 25 years. Put us in the top %.05 Faith ,family ,friends ,physical and emotional strength/peace is what I strive for daily. It is not what we hang on to, but what we can let go in life that matters. Too many idiots agonizing over money constantly Remember…………no one is rich in the cemetary Hope this helps

Frank
Frank
2 days ago

Dear Sam,

For the sake of your wife and family I hope your investments pan out. Most people underestimate how difficult it is to come back from heavy losses after age 50.
Please consider the trillions of dollars waiting on the sidelines eager to help orchestrate the mother of all crashes. A %50 correction is possible in my opinion. If/ when this occurs very few people will be protected from it. Historically, the %1 will desperately try to flee but there will be no place to run and hide. If somehow, everything works out perhaps it is time to focus on singles and doubles exclusively.(see below on venture investing)

Harvard Business School (Professor Shikhar Ghosh): Classic research conducted by HBS Senior Lecturer Shikhar Ghosh famously breaks down the “rule of thumb” in venture capital portfolios. He notes that if you define failure as liquidating assets where investors lose most or all of their capital, the baseline failure rate is 30% to 40%. However, if failure means failing to see the projected return on investment, the failure rate shoots up to 70% to 80%. [1, 2]

Sophia
Sophia
4 days ago

Maybe consider a heloc in the meantime? Lately I have been cash poor investing in alternatives for fun. Hoping next year I can force myself to spend more in the fun bucket.

reader
reader
7 days ago

At what age will you stop investing in VC? I’m younger than you, and I already feel like I don’t want to tie up so much money in VC investments that usually have such a long time horizon. I don’t know how people stay motivated in their 50s+ unless they are trying to create a legacy.

GREGORY
GREGORY
8 days ago

Why isn’t it all mostly the same? You’re using income that you receive, and pay some tax rate on, so if you had all the cash, then you either hadn’t invested it, or you did and now you have to pay a tax rate on those gains. I’m not nearly as adept at these things, so please don’t take it the wrong way.

Chris
Chris
8 days ago

You’re definitely running the knife edge between risk and reward much more than I would be comfortable with, and I hope this works out for the best for you. There is absolutely no way I would take on this kind of exposure, so it’s interesting to hear that you find this exhilarating and don’t seem to have regrets. Even more surprising is reading in the comments that others share this need for “adventure”. I guess we’re all built differently, and that’s OK! Hope you’re able to knock it out of the park with this one!

Brian Gibb
Brian Gibb
6 days ago
Reply to  Chris

100% No thanks but good luck!

Alex Crossman
Alex Crossman
2 days ago
Reply to  Chris

I thought the same, i am a long time financial samurai reader and reaching back a few years Sam looked at interest rates, muni bonds, RE and lower risk investments a lot more than he does today.

I read the investment and it looked messy and risky on almost every point.

Part of me wonders if this is late stage bull market normalized risk taking on his part.

Gavin
Gavin
9 days ago

Hi Sam, I’m a long time reader and have always found your posts interesting and thought provoking. All that said, this particular post just misses the mark. You are nowhere close to broke so equating being broke to having to possibly sell some existing investments to meet capital calls is tone deaf at best.

I know you got the same type of feedback when you wrote about having to live “paycheck to paycheck” a few years back so I must say that I am surprised that you have chosen to go down this path again. It’s fair enough if you wrote this post to encourage debate and discussion but please know that you’ve already successfully done that with other posts where you don’t present yourself as struggling financially.

David
David
9 days ago

Too bad you were locked up on VCX and couldn’t take advantage of that crazy run-up.

Jeremy
Jeremy
9 days ago

This is too funny. Great post. I’m 45 years old and did the same thing. I’ve been feeling bored lately, having built too much liquidity to try hard at work (I’m self employed). As a result of being too liquid I’ve been taking time off, letting my body go a bit, relaxing at the gym, not pursuing as many deals. So, I manufactured the scarcity that has driven me in so many years prior. I committed a large amount to various VC funds. They made capital calls. Now I’m (short term) cash poor again and it feels great. I’m reinvigorated at work to find more deals. I feel alive again. Such an odd feeling isn’t it?

Michael
Michael
10 days ago

Hi Sam, in a previous article, you mentioned taking profits to pay for a better life (https://www.financialsamurai.com/practice-taking-profits-to-pay-for-a-better-life/). Why are you hesitant to do so in this situation?

Geoff Elmore
Geoff Elmore
10 days ago

This is now my favorite article that you have written. Exceptionally informative as well as interesting and entertaining. Well done.

Vinay
Vinay
10 days ago

I read your weekly articles. I remember you saying you missed the VCX boat on the last $10k email, which would have allowed you unrestricted shares. Can you help clarify – if you had other unrestricted / restricted shares from VCX from earlier tranches. I remember everything prior to that max $10,000 allowed in Mar’26 just weeks before VCX got listed was to be 6 months restricted before trading.

Vinay
Vinay
10 days ago

Oh nice.. I did not realize the multiple accounts. I was lucky to invest that $10,000 as I got the email, I just had my annual bonus from work come a few days earlier that week and I had conviction to expect a quick premium just reading everything you had posted and generally online on VCX. So got a little over 500 shares and I did sell it during the initial spike at its peak, at average $530/share.. I still have 2,000 plus shares from prior investments that I built on from early 2025 that I plan to keep long term.. hopefully it can 10x in next 5 years or so.. its at 3x.. but curious as I am not seeing much public info on VCX unlike other CEF’s or ETF’s out there to really research more on my end.. Is that because VCX is not sharing as much and just doing the bare minimum.. I don’t get any useful info like for the top holdings compared to Mar’26 when it listed or any updates per se.. not to say, i haven’t seen any articles at all – Financial Samurai has been useful with how you explained your rationale on NAV and the big Anthropic IPO could be a catalyst.. but still feels like less out there.. I use stockanalysis.com for all my research.. I presume you have heard of it.

Jamie
Jamie
10 days ago

Oh my this has been so fascinating. I learned several things I hadn’t heard of before. Recycling caps, pledged asset lines, line of advances, and funds using subscription credit lines and how the size and timing of calls may not line up to real world deal timing. I would have a very hard time with that type of investing. I don’t like unpredictability and would likely just end up sitting on too much cash b/c I’d want it liquid and ready to transfer at a moment’s notice. And then I’d likely end up losing out on larger gains by keeping too much in cash for too long. But maybe less so based on the accelerated calls timing you’re seeing. So much is moving so fast with AI. It’s exciting to watch but also nerve wracking. I’m glad you find some of the added financial pressure exhilarating. If it was all stressful it just doesn’t seem like it’d be worth it. Thanks for sharing so many insights.

John
John
10 days ago

Sam, thanks for this. Your writing on venture capital is some of your best work. This is probably the murkiest of all investments for most of us. Keep up the good work. Health to you and your entire family.

–John

Martin
Martin
10 days ago

This maybe a really dumb question. Is a HELOC on one of your properties out of the question ?

Stephen
Stephen
10 days ago

A fund manager is very unlikely to put you in default for missing a capital call. It’s operationally more burdensome for them to put your in default, plus they will get questions from prospective LPs what their default rate is and they will want to say 0% in their DDQ meetings. Their investor services team in most instances will send you a reminder that you haven’t paid and you can simply wire in the cash late. They are going to be much more concerned about their large institutional LPs paying on time than a HNW investor.

Dave
Dave
10 days ago

Get a PAL/LAL that allows the funding of capital calls. Or worst case get a margin loan at a higher rate to smooth the timing mismatch.

And a sub line doesn’t increase your capital calls- just defers it and plebeian aggregates then instead of having a whole bunch of annoying ones that are administratively burdensome (and you should be paying less than the hurdle rate for the debt in most cases so it’s positive carry thru the J-curve)

Stewart
Stewart
10 days ago
Reply to  Dave

I was just going to suggest this. I have a SBLOC with Frec. Interest is 4.8% currently that is tax deductible if used for investments. This is how I manage capital calls and oil and gas investments without having to sit on a huge amount of cash. My rule is that I can only use what I can pay-down within a year, and it’s only used for investments. You have a fourth option.

Jim Johnson
Jim Johnson
10 days ago
Reply to  Stewart

Hi Stewart
What are your favorite oil/natural gas investments currently?

ASH01
ASH01
10 days ago

Yes I use this too. PNC just calls it a “Commercial Loan”. I recently used it when I bought a house for cash but wasn’t getting the cash equity from my old house I sold for another 2 months. The equity from my old house would pay for the new house in full, but timing wasn’t right. So PNC fronted the cash off my investments – it functioned like a “bridge loan” allowing me to make an attractive all-cash offer on the new house even though the cash assets weren’t really available without selling stocks.

KO
KO
10 days ago
Reply to  ASH01

I wish that I had done something like this before buying my previous home. The all-cash offer clinched the deal, but selling the highly appreciated stock created a huge tax bill. I hope that tax revenue is being spent effectively! Live and learn.

ASH01
ASH01
9 days ago
Reply to  KO

Sometimes I do dislike having some of assets at a wealth advisor and paying 0.75% AUM. BUT it was nice calling my account manager and he had the loan set up overnight, allowing me to jump on bidding the house. We would not have got it if not all-cash. I have alot of money at Vanguard too, but doubt they would have been able to set it up so quick. As soon as I got the equity from the house I sold I paid off the commercial loan in full. I was like “so this is how the rich use money to their advantage.” It was eye-opening to have 1M in cash available overnight.

Dave
Dave
9 days ago

At this point I try to use my distributions and realizations from my private to pay down my LAL (Morgan Stanley) on a regular basis. Effectively the profits and distributions eventually self fund new cap calls and the LAL is really just timing mismatch. However sales over the last 4 years have been slower than expected and especially in private credit and RE.

Heloc is another good way but it’s usually more expensive (at least for me).

Happy to go into detail on any of this or subscription or NaV facilities which can be good or bad depending on perspective and manager abuse

Dave
Dave
9 days ago

So I have a line that’s sofr + 150, but also have taken term loans with 5 and 7 year terms when rates were lower (both below 3%) that sadly mature this year and next year.

I go thru my FA when I set it up (same with my mortgage – 10Y I/O done in 2021, talk about great timing). And while I don’t normally suggest an FA, I work I. The industry and need to have one as I cannot buy individual stocks or securities in my current role, but they know my risk tolerance and we discuss my goals and I have a very discounted rate (and I get to invest in private as sponsored by my firm at no fees or carry). So overall I make out imo as they handle all my operational stuff and reminders/tax/estate interaction with my accountant and lawyers.

When I retire (soon?) I will self direct again (maybe?) unless the cost stays abnormally low.

Dan
Dan
10 days ago
Reply to  Dave

Sam, another great one. I waa wondering if you’ve ever ran a retrospective analysis to assess % returns in your VC bets vs the S&P or Nasdaq 100 net of all fees and where it has netted out over time? My sense is that there is a small chance to find lightening in a bottle with VC investing vs index, but the probability of catching it is likely <1%. Assume a NW north of $10m—Is that a bet worth placing.

Dave
Dave
9 days ago
Reply to  Dan

Return isn’t the right indicator on its own, have to assess the risk and diversity effect to achieve the return and basket of returns (and ability to get that exposure to be diversified) in my opinion.