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AllTopicsToday > Blog > Investing & Finance > Summer YOLO Fund: Permission To Spend More and Save Less
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Investing & Finance

Summer YOLO Fund: Permission To Spend More and Save Less

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Last updated: June 29, 2026 5:36 pm
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Published: June 29, 2026
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In anticipation of investing in a startup for YC Demo Day, I transferred $50,000 from my Constancy brokerage account to my Citibank checking account. This was proper after I had already transferred $56,100 to fill a brand new conventional enterprise capital fund name that I had dedicated to.

In a earlier submit, I wrote concerning the problem of committing to a brand new enterprise fund as you grow old. Ultimately, now that I am 49 years outdated, I’ve determined to simply maximize my family and friends allocation. Even when it’s a must to wait round 10 years to get your a refund and the charges are excessive, it is a tier 1 firm.

In different phrases, I used to be loaded, locked up, and able to deploy. The capitalist was sitting there with just one job. Discover your subsequent nice firm.

What I underestimated is how straightforward it’s to jot down a examine. Moving into the YC firm I truly needed at an inexpensive valuation turned out to be the troublesome half.

I used to be going to jot down a examine for $25,000 to at least one firm and a examine for $25,000 to a different firm. Nevertheless, the primary spherical was successfully full, and the second spherical was capped at $40 million. So I diminished my funding to $10,000.

All informed, I instantly had $40,000 in money and was fully free with nowhere to go.

And what higher time than summer season to be sitting on an surprising pile of money? So the Summer season YOLO Fund was born.

I by accident created the Summer season YOLO Fund utilizing $50,000 that was initially earmarked for angel investing in startups. One startup has been allotted $10,000 and has not but acquired a brand new SAFE doc settlement. So that you would possibly be capable to spend $50,000 as an alternative.

FIRE requires steady delayed gratification

After a long time of saving and investing most of my revenue on autopilot, getting permission to spend is a present.

To know why $40,000 in unspent money is such a psychological occasion for me, it’s a must to perceive how I acquired right here.

I knew I needed to FIRE by age 40 throughout the first three months of beginning my profession at a financial institution in 1999. I knew I could not maintain a 40-year profession of coming to work by 5:30 a.m. each weekday, leaving after 7 p.m., after which working a number of hours each weekend. So I made a decision to save lots of and make investments as a lot as humanly attainable and purchase my freedom early.

Since 1999, I’ve saved 50% to 80% of my revenue annually. Not as a result of I am a masochist, however as a result of I all the time had a transparent aim in entrance of me. Develop into free by the age of 40. purchase a home Assist your spouse plan her personal escape. I’ve a toddler. Be a stay-at-home mother or father for the primary 5 years of every kid’s life. Please assist pay for my dad and mom’ care. and so forth.

Ultimately, it seems that life is only one monetary quest after one other. When you clear one boss degree, the subsequent boss degree will load. Subsequently, turning off the gasoline on investments turns into an virtually unimaginable activity.

The issue is that I am coming into center age and most of my massive quests have already been accomplished. And if you cannot put your cash into the startup you need on the worth you need, your cash will simply sit there and ask what its goal is.

For the primary time in years, the reply is, “Let’s simply dwell somewhat.”

Angel investing is sort of a fantasy YOLOing

Let’s be sincere about what angel investing truly is. Losing cash on further steps and higher decks is YOLO.

You unfold out dozens of small bets on early-stage corporations, realizing full nicely that about 90% of them won’t yield constructive returns. Most rapidly go to zero. As an LP in varied conventional enterprise funds for almost 20 years, I’ve seen this energy regulation play out many instances. The fund is backing 60 startups, of which three to maybe 5 will generate 95% of the income. The remaining are both bagels or zombies with no means out.

I dressed enterprise informal and saved $150,000 a 12 months for this sort of high-risk, high-reward playing. One of many causes I preserve driving my 11-year-old automobile as an alternative of spending $100,000 on a brand new one is to maintain funding these very bets.

However here is the irony. Even when the plan to deploy this spherical to startups did not work out, the cash did not disappear. I simply modified jobs. It went from “perhaps funding an organization that lasts for generations” to “positively funding my children’ mango season.”

One in all them ensures a constructive return.

Why it is so laborious to spend cash even after a long time of saving

It is surprisingly, virtually comically, troublesome to cease spending cash, regardless that you’ve got spent a long time coaching your self to not.

Having saved over 50% of my revenue for 27 years, this behavior has develop into a part of my id. Simply because a spreadsheet tells you to begin accumulating property does not imply it’s a must to flip off your id. Each time you spend cash on one thing that does not work, it units off somewhat inside alarm that took a long time to put in and apparently does not have an off change.

I’ve written earlier than concerning the unusual incapacity to spend cash on your self and the way investing is extra interesting than spending. The mathematics mind wins virtually each time. A $40,000 angel examine feels productive. A summer season of $40,000 mangoes and massages appears reckless.

That is the lure. The very self-discipline that makes you financially unbiased is similar self-discipline that stops you from having fun with it. We optimize ourselves into corners.

And the price of staying in that nook is actual. The worst monetary final result just isn’t working out of cash. Too usually it dies as a result of it means you are buying and selling years of your life, stress, and vitality for a quantity on a display that by no means translated into good recollections.

We have to deliberately change our spending habits as we age.

The merciless joke of frugality is that it could possibly quietly solidify life-style deflation. My revenue has elevated, my internet value has elevated, and my bills stay frozen within the thoughts of a nervous 32-year-old who simply watched the dot-com bubble burst. That feeling of doom from 2009 has by no means fully left me.

That is why when you flip 45, you need to contemplate coming into the decuration part. We purchased a home in 2023 that we did not technically want. I ship my two youngsters to unbiased faculties when public college is enough. And we selected to not work full-time jobs. However they’re straightforward to justify. we’ve to dwell someplace. We place nice significance on studying a second language. And we’re wholesome when we aren’t certain by another person’s schedule.

A very painful expense is an expense that has no justification aside from pleasure. It is a a lot nicer automobile than it must be. Meals that make our bellies greater. A therapeutic massage that quickly makes you’re feeling higher. These are bills which have zero return on funding and 100% return on life, and are precisely what my mind refuses to approve with out a combat.

So this summer season, I will tackle the combat. And I will win it.

Summer season FIRE session is in full swing

For the whole month of July, I’ll additional scale back my social media use, no consulting classes, no replying to emails, and no business-related conferences. Writing just isn’t work for me, it is oxygen, so I’ll proceed to jot down frequently. But when not, I will be in full conventional retirement mode. Consuming, going to the seashore, mountain climbing, swimming, enjoyable. It was precisely how I imagined FIRE would really feel earlier than I stop my job.

It is laborious to spend more cash in Hawaii as a result of we’re staying in our childhood residence. And whenever you get again “residence,” you do not go absolutely into trip mode such as you do whenever you’re at a resort. However after my dad and mom, sister, and I cut up a $41,000 renovation of our two-bedroom in-law unit, we had been lastly in a position to develop shut sufficient to really feel like friends of the household relatively than labor. And because the lodging is successfully “free”, you may truly get pleasure from way more disposable revenue.

Mix that free lodging with a fortuitous $40,000 Summer season YOLO Fund and you’ve got some critical firepower to deploy in reminiscence relatively than metrics.

Summer season YOLO Fund Spending Plan

I think about how this fund might be used.

$2,000: Roughly 350 regionally grown Hawaiian mangoes for six individuals. Native Hawaiian mangoes are my favourite fruit. It is much more scrumptious than the lychees that fall from the timber in Taiwan. I plan to eat 2-3 items a day and check out valiantly to not acquire weight. $6,000: Dinner and takeout for 4-6 individuals. Along with Korean barbecue and top-quality poke, there are a number of resort eating places with ocean views. That is the simplest and quickest method to trick your mind into considering you’re actually on trip. $2,500: Household enjoyable at amusement parks and reveals. Sea Life Park, Moist n’ Wild, a magic present, and possibly a luau because the children have by no means skilled one. $1,000: Therapeutic massage and spa remedies for my spouse and me. Therapeutic massage is sweet for well being. $500: Gasoline and different transportation. $500: Sneakers and souvenirs for teenagers and households. $2,500: New 15-inch MacBook Professional, costlier than my 13-inch. Honolulu’s gross sales tax is about 45% decrease than San Francisco, so my frugal mind feels prefer it’s successful one thing. Wait a minute, it is a work instrument, not a YOLO fund expenditure. $5,000: Set up new blinds or curtains in the lounge of your in-law unit. We have already redecorated the bed room and laundry room, so we’re achieved. This isn’t a enjoyable expense both.

This brings us to $20,000 in comparatively straightforward and bonafide spending. However $7,500 for a brand new laptop and blinds is not actually trip spending in any respect. So how precisely do you spend the remaining $20,000 to $27,500?

A luxurious rental automobile so I haven’t got to drive round in my father’s 28-year-old Toyota with air-con, no Bluetooth, and the driving force’s window that does not roll down? How a few family-friendly sundown catamaran non-public constitution? A enjoyable however harmful helicopter tour of the island, or an expert photographer to seize your moments on the island?

no. I am licensed in iPhone pictures so I can take wonderful movies and pictures without spending a dime.

Convert funding cash into dwelling cash

This entire train was a enjoyable lesson in repositioning. The identical $40,000 that was destined to develop into a 10-year illiquid guess on another person’s dream is now funding my family’s ongoing existence. It is a actual trade-off that occurs each time we make an angel funding or develop into an LP in a enterprise fund.

Name it consumption smoothing, name it revenge spending, name it something that really triggers it. The aim is to place a few of your hard-earned capital again into what you had been chasing all alongside – life, no more cash you do not want.

After 27 years of delayed gratification, I’m lastly on observe to attain some gratification. If the correct deal comes alongside on the proper worth, the startup capital will finally be deployed. Till then, I’ll deal with this unspent money as actual, as permission to spend it at precisely the correct time and with the correct individuals.

It is a enjoyable time.

Expensive Reader, How troublesome is it to really spend cash for these pursuing or dwelling FIRE? What’s probably the most “unfair” buy you’ve got made lately that turned out to be 100% value it? And if you happen to instantly had $40,000 free with no obligations, would you make investments it or make investments it in an expertise?

On your summer season studying decide up the USA Right this moment bestseller Millionaire Milestones: Easy Steps To Seven Figures. It is a sensible roadmap to construct wealth quicker and switch that wealth into a lifetime of freedom. As a result of life is a lot simpler when you may dwell it the best way you need.

Read Millionaire Milestones book on the beach
This can be probably the most enjoyable and informative summer season learn you are able to do

A simple method to passively spend money on actual property

If you happen to’re like me and need to get into actual property with out worrying about tenants, loos, or six-figure down funds, contemplate Fundrise. The corporate is among the nation’s largest non-public actual property platforms, with a various portfolio of residential and industrial properties, many positioned in low-cost, high-growth areas, the place yields are inclined to outpace costly coastal cities like San Francisco.

By doing so, I can passively publish actual property with none trouble. The minimal quantity is simply $10, your funds are open to everybody, and you’ll dollar-cost common over time as an alternative of timing your massive purchases suddenly.

Monetary Samurai is an investor in Fundrise and a long-time companion of Fundrise. This relationship helps assist the free content material on this website.

To get my finest content material delivered straight to your inbox, be a part of over 60,000 readers and join my free weekly e-newsletter right here. We’ll present you the right way to construct extra wealth and develop into free quicker than 99% of individuals. And when you’re free, we’ll provide help to with the surprisingly troublesome half: truly having fun with it.

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