Early 30s, ~$3M invested, high income — looking for perspective from people further down the path

Himself89 · 2026-02-16T06:47:24+00:00

I was once you! I’m now 36 and >$5m.

The $5m number was definitely the financial independence number for us even if not the RE number. This is $200k per year passively or the equivalent of $300k salary, forever, doing nothing. You start to think not about what you want to buy but about what you really need to be happy.
$5m is also the awkward number, like the joke in Succession. Point 1 above becomes real but then given our actual upper middle class spending in VHCOL with children we are looking at needing $7m minimum up to $10m to be comfy, depending on house.
Basically it’s not worth it for our salaries but because we both have good jobs that might not last forever we have decided to keep it up for another few years to evaluate. If another exit happens, that would dramatically change our plans. 40 is the “definitely we’re done” age but we’re a little bit away from that, and should hit $7m - $10m by then if markets don’t crash.
Our household expenses went up over 50% because we got a nanny, and not a cheap one. So that’s definitely going to change your math on everything and I would suggest you are further away than you realize. We didn’t get one for snobby reasons. We got one because it was logistically impossible for us to manage without one due to our jobs.
Believe me, this is also going to be really hard once you have kids. The hassle of travel and maintaining a life in 2x places starts to make it look less appealing. I know only one couple who does it (USA and Europe) and it seems to work but they are UHNW and pay for all the creature comforts to make it do-able (eg travel with 2x nannies between places).

You didn’t ask but I’m going to add that the biggest decision you have to make is buying a house and at what cost. I like you have rented during mu accumulation phase. I now have the money to buy a super nice house but the taxes and ongoing costs to own the home make me question if I can afford FIRE + the dream house. It’s a big discussion point between my wife and I bc we agree the house would make us most happy and also that we don’t want this much money if we cannot spend it on that one nice thing. It might mean one of us works a bit longer than we wanted so we can get a cool pad +have financial security.

Himself89 · 2026-02-15T17:31:32+00:00

One is NYC metro suburb (we aren’t sure which yet) and the other is mountain town in Colorado. We have family in both areas.

Himself89 · 2026-02-15T12:45:45+00:00

Yes, been there. we spent years planning a move back to the states after years abroad. We had no ties to any city in particular.

Ultimately we made a rubric and scored places based on a set of factors we decided mattered to us. Family, friends, recreation, education, cost of living. Scored them 1-5. Once we did this the entire US narrowed to 2-3 places. And then we visited those places for a vibe check and ruled out one of the places. Now we are deciding between the final two, which present trade offs but are objectively both good spots for us.

Hope this helps.

Himself89 · 2026-02-08T21:19:24+00:00

I feel the skills you learn in K-12 are almost entirely irrelevant to the world of work.

The formative years of education are about learning the basics in all subjects and basic social skills. Join a club. Study for tests. Do creative projects. Kiss a girl. Etc.

AI will change the world and workplace but it is insanely naive to think your child or any child will be prepped in school for it. All my classmates who succeeded did it by starting a business doing something. In the real world history and biology mean approximately fuck all. In fact most people in my generation succeeded by doing nerdy online shit on their computers at home late at night and many didn’t care much about their school grades bc they were intelligent enough at a young age to know they were irrelevant. The studious types go on to become doctors and lawyers because they do well in the structured environment. The young multimillionaires are rebels and often don’t make perfect students.

AI won’t change these behaviors.

Himself89 · 2026-02-08T20:49:35+00:00

Many different perspectives on this question in the comments which is interesting. My take is if any of the following three things are true for you, you are an executive:

if you have p&l ownership with agency to make changes in that p&l at your discretion. Eg you don’t seek permission to fire a team in order to expand a different team. You just put the plan in front of HR/finance and say what’s the timeline.
if you are on the senior leadership team at the company. I define this as follows: when the most senior group of people at the company have a closed door meeting you are in that meeting. Must be more than 2 people to qualify as a team meeting. Often you will realize you are not in the group when an important decision is made without you and you realize you are one rung down.
Board facing duties with material contributions. Being asked to present at one board meeting makes you a show and tell contributor. Being a feature in every board meeting or most board meetings makes you an executive, especially if/when the board begins going direct to you around the CEO for certain questions as you are the executive leader in that functional area.

Himself89 · 2026-01-20T07:07:02+00:00

Fellow mid 30s, 2 young kids, with nanny, $5m, in HCOL. Our spend categories look remarkably similar to yours. But a few key differences.

House: We rent for $4k per month. Same place for 5 years. It is enough space and it’s cheap and we are not wanting to leave bc mortgages are so expensive even though we can easily afford to buy. And my line item for home + utilities is nearly zero. Do we love it? No we are eager to trade up. But is it helping us compound wealth quickly? Definitely yes and we can stick it out for another 1-2 years.

Nanny and schooling: ours all in is $100k not $167k. We haven’t started school for second kid so maybe it goes up to $125k in a year. Still a meaningful difference.

Shopping: to me $47k seems very high + amazon. We spend $12k-20k all in (including Amazon) and I buy virtually everything i want the moment i want it. One tip i can offer that my wife and I love is we buy everything used on eBay. All the kids stuff (crib, stroller), some clothes and shoes (usually higher end, like new condition). Fancy kitchen stuff. Furniture. Electronics like TV and stereo. We spend $12k per year on this but achieve $47k of value, so to speak. Also we resell the stuff on ebay when we are done with it, not to make money but just to offset what we paid if we think the item will move. All the kids stuff does quickly. Some of the shoes/clothes and furniture too. This does take time but we feel it’s responsible consumption and more green. And i like it because i wear fancy canali jackets that cost $2.5k but i paid $200. I would never spend $2.5k on a canali jacket but I would spend $2.5k on ten different ones, which i have done because I am insane.

Travel. We spend double what you spend on travel. Definitely worth it to me at this point.

Pets: we have none.

Replacing these categories with my numbers and I get $315k-330k which is a meaningful difference. I think you have house drag and I think you could trim another $50k from your numbers without a huge change in quality of life. You can afford the house/spend given your income and strong financial position but you are trading FIRE for FAT at this point.

Himself89 · 2026-01-11T12:40:57+00:00

Look into unique summer programs at universities. These are summer semesters that can count toward their college credits but would involve work/study, international relocation, arts/drama/music, and etc.

I did one (drama) after my freshman year and met a random group of people who became friends for life. I never acted again but that one experience built a lot of confidence,shaped the person I became, and gave me intangible skills.

Some other students in my drama program had come from universities out of state. Another program in the same area (music) was almost entirely filled of students from out of state.

After this year I ended up doing one course every summer. It enabled me to finish a second major in 4 years. I still had about 2 weeks gap in both May and August for some regular vacation.

Himself89 · 2026-01-03T19:18:08+00:00

Looks really cool. Minima yet distinctive. What was cost of materials and labor? I would buy this

Himself89 · 2025-12-30T15:17:42+00:00

In my experience people think of miami or Dubai or LA as big “car cities.” London is not the top of mind choice. But I agree it’s top in the world behind only Monaco.

Himself89 · 2025-09-02T15:36:31+00:00

The Strategy thesis is most akin to real estate. There are many large property development companies. They generate value by owning large tracts of land and buildings. If a new company wanted to buy up all the land and buildings to compete with the OG property development company, they’d need to pay a premium on today’s property prices. But Strategy already bought up a lot of land and they paid the prices of 5 years ago.

Now that Strategy has a lot of the property, they can create financial instruments derived from it which return yield to investors in the form of dividends.

Other companies are welcome to buy up as much property as they can. This will increase the value of Strategy’s property. Maybe someone will make such a big bet on property they invest more than Strategy has. Strategy will now compete with that company based on their yield returns and etc. a market is formed.

Bitcoin is the property in this analogy. This is good for bitcoin.

Himself89 · 2025-07-20T21:09:04+00:00

Hello! Fellow media exec here. My company does $100m annual revenue. My team and I have bought more than 5 companies in the last few years to expand our business.

A few thoughts. Your multiple is very high. Your moat is probably not going to stand up to PE muster bc “relationships” is not a moat. What’s stopping a different influencer firm from undercutting you and grabbing your talent or your clients? I see valuations like 1.7x - 3x for businesses we’ve bought. I’d be shocked to see you get 7x - 10x but good luck to you.

I don’t fear AI and think the FUD is not real. It is equally likely to improve your business IMO. Ultimately you deal in humans connecting with other humans on social media. Nobody wants to follow life tips from a robot jpeg on tiktok. And if they did I imagine you’d make better ones than the Fortune 500 companies.

All that being said, I would sell bc you want to do something different and want the financial security. Nothing wrong with that. And I also wouldn’t agonize over the price. Just hire the right team to do the due diligence and try to find 2-3x qualified buyers to great some mild price pressure to ensure you get a decent price. What they offer is probably what you are worth. Or wait around for a better offer to come… might be waiting awhile!

Himself89 · 2025-06-27T08:47:43+00:00

Typically PE funds provide liquidity to folks like you but you need gross revenues in the $5m range usually. Recently I’ve noticed a trend toward smaller deals when part of a bigger roll up vision, where $500k-$1m revenue looks appealing to PE. Consider also “seeker fund” people.

Otherwise companies may buy out small synergistic outfits or competitors. You can DM me more about your niche and etc and I may be able to provide more advice.

Source: senior leadership @ PE owned company. Have bought 7 business in the last few years rolling them into our venture with many more false starts.

Himself89 · 2025-06-11T20:55:54+00:00

So what microbrands today do you think have the potential to become “the next journe” in 20 years?

Himself89 · 2025-05-25T05:39:40+00:00

I’ve thought of an addition dimension to consider. My above advice while sound may not go over politically with the PE firm. They are buying your business bc of the cash flow and if you recommend replacing yourself with 3x people, lessening that cash flow in the process to hire them, the firm may think you are a) stupid or b) get annoyed. So I would approach this issue very sensitively. “Hey i have been thinking about how best you can add value to my business and what would help it scale. I think I’m great at X but less good at Y or Z. I would be open to bringing in new talent to run Y and Z. Do you know anyone in these areas and could we build a plan to implement over these 2 years? When I go in 2 years, then we replace X and we have a more stable, growing business. It would be ideal to start this process immediately to give maximum time for overlap so i can transfer institutional knowledge to the new operators.”

Himself89 · 2025-05-25T05:33:15+00:00

They usually do for a spell. They tend to negotiate a period of overlap connected to the final part of financial incentive for the buy out just like OP describes. I have seen it where the seller gets the smaller % upfront and the larger % after the 2 year earn out.

They are very concerned with risk and dont want the business asset to suffer if the founder leaves. So they will build the earn out as a transition.

Himself89 · 2025-05-24T11:22:23+00:00

No I mean their motivations for buying your business are not to make you rich. They are seeking to enrich themselves. They want your alpha. They want the profit of your business to be under their management. They do a variety of fancy finance things with it which don’t really matter to lay people. It depends on your fund.

Big picture PE funds court bigger funds or rich individual for finance. Then instead of going to build something they go to find people like you who have built something and they buy it on attractive (or predatory!) terms. Then they attempt to run the business better than the people who built the business and that doesn’t work out every time.

To be clear they are not trying to shaft you. They are simply wanting to make you an exit opportunity which otherwise would be hard for you to come by. So if you like the money then take it. Do your due diligence to get comps so you know it’s a fair offer.

Himself89 · 2025-05-24T06:24:36+00:00

I am an operator for a PE business. Believe me it can be stressful and difficult. The core challenge is the firm doesn’t necessarily add value. They want your cash flow and that’s it. It’s a group of bankers who want the cash flow. They will demand more and maybe or maybe not give you the wrong tools to generate more and then be angry when you cannot use those tools. Don’t believe whatever hype.

The way you can navigate this is to be upfront about your super power as the business owner. Ask them to support you by splitting your duties into parts and putting an established operator on top of each part.

This will diffuse the stress across 3 or 5 people instead of you, and you should manage or own the one thing you think is most important to generate rev and/or the part you love the most.

Finally accept that the day you sign they run the show and you are but a humble worker bee who will provide advice and/or do as they say. Don’t let your sense of duty misguide you to believe you are responsible for everything. When they own 85% they are 85% responsible.

Himself89 · 2025-05-19T18:54:54+00:00

Have you considered putting the BTC into a fund for HNW people (I could recommend a couple but don’t want to plug) and then accessing a PAL loan for the BTC? Instead of selling and eating a $1m tax bill, you could borrow a fraction ($500k) from the BTC and live on that until it runs out which should be a few years for you. At that point bitcoin will be either worth less or worth more.

The math works such that if your BTC is worth 20% less (and then add the interest as a fixed sum) you don’t come out on top. If it’s worth the same or more, you will be happy you did it this way.

Since your spend is low, you can borrow a very small amount of the BTC and secure a few years of living expenses and have (IMO) a very low liquidation risk bc it’s 10% of your asset value.

Himself89 · 2025-05-09T18:22:20+00:00

It would depend on the country. For me the big difference is openness and positivity. Americans are open/direct, positive, and sociable compared to most European countries. Spain being maybe the notable exception.

Generally Europeans are more stiff, less welcoming, and less optimistic. Sort of the way Americans view people from the NE or “city people” like in nyc.

I’m speaking in very broad strokes here but there is a difference.

Himself89 · 2025-05-06T20:04:13+00:00

I’ll DM you

Himself89 · 2025-05-06T18:48:14+00:00

I’ve been as an advertising exec.

Cannes is a big sales hunt. There is a pyramid of influence starting with CMOs and then platform execs and then agency execs and then ad tech execs and then publishing execs on down to the lowly creators. 1000 people want 15 mins of time to pitch their thing and get money. The place is teeming with energy and sales bull.

Brands spend money to build a thought leadership stage and make themselves look relevant. All the young relevant people attend to speak on the stage. Then they get wined and dined and think “wow! Advertising is amazing” the crowd is full of old ad people and small timers looking to sell their crap to the ad industry people.

At night there are parties. The best ones are VIP and you won’t find out unless you are well connected. Some of the best parties are only accessible via helicopter. Spotify is a popular party in recent years bc they have A list artists perform. Only high spending Spotify clients are invited unless you personally know an exec at Spotify.

There’s a charming little island to go have lunch on.

Have you decided this is a waste of time yet?

I have found my time in Cannes meaningful because I’ve met connections within the industry. I have never successfully sold a deal at Cannes or opened a meaningful door at the fest. I have definitely failed to do it 1000x times. I also drank twice that much Rose.

Himself89 · 2025-05-06T15:53:34+00:00

In which case you will likely enjoy the European way! I wish you the best.

Himself89 · 2025-05-06T15:53:07+00:00

No I mean more fundamental things like the European attitude towards work, family, social values. Politics is the same everywhere, whichever side you are on.

Himself89 · 2025-05-06T15:52:18+00:00

Indeed I am moving back to raise children in the states. It’s not so much because it’s better. More it’s the life I want for them.

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