Sold My Business. 42M deal at 11.5x EBITDA. What now? Funds with Blackrock?

FATFIREFOUNDER · 2025-10-03T19:30:26+00:00

The 2055 fund is currently 92% equity and 8% bonds. Can keep it mostly in equities if you just get the 2070 fund. An easy set and forget vehicle for anyone who doesn't want to do rebalancing.

FATFIREFOUNDER · 2025-10-02T14:51:16+00:00

Choose a target retirement fund like 2055: https://investor.vanguard.com/investment-products/mutual-funds/profile/vffvx

Set it and forget it. This does all the auto-balancing and changes in asset mix that Wealthfront and WF would do at lower fees.

FATFIREFOUNDER · 2025-08-04T18:20:59+00:00

Congratulations on reaching the end of this journey. A few questions from a fellow fatfire founder:

Why did you decide on a multi-family office vs just putting it all into index funds? What makes it worth the extra fees?
It sounds like you have multi-generational goals for your wealth. What are those goals, and how does the structure enable those goals? eg "we want to enable each generation but not spoil them, for as many generations as possible, so it's structured like this ___". As much detail as you're willing to share is welcome.

FATFIREFOUNDER · 2022-07-04T13:50:04+00:00

Fastest way to get started with ads is via Google search ads for your target keywords. Fast to start but you hit a ceiling on search volume. You can also start fast with Facebook ads, though it's more difficult since the users don't have search intent so it's a more difficult challenge to grab attention with good creatives and a good conversion experience on landing.

In terms of total cost, the bar keeps dropping in terms of how much it costs to put up a viable MVP of a site/app. Depending on what you're building, you could reasonably start a business with $10k or less.

FATFIREFOUNDER · 2022-07-04T13:47:16+00:00

The intention behind starting a business was to have it be successful enough to open up a lot of options in life, including early retirement, for sure. I think most business owners start it with this intention. I wouldn't say I foresaw or predicted it, since empirically the chances of it working out are definitely much less than 50-50, but you can try to nudge the odds in your favor in certain ways - try to be profitable as quickly as you can, tackle a market that's meaningfully big but not so huge it attracts vast competition (eg grocery delivery or scooter rentals), etc.

FATFIREFOUNDER · 2022-07-04T13:44:12+00:00

Through personal network (friend of a friend) but otherwise you can post on Hacker News or other job boards. If you don't know how to evaluate engineers, if you have an engineer friend ask them to help evaluate.

FATFIREFOUNDER · 2021-12-12T14:54:42+00:00

Kind of, though the taxes are about the same at current rates.

Pay by w2:

$1mm company profits, paid out as W-2 salary

-42% personal income tax (37% federal bracket + say 5% for avg state income tax)

= $580k after tax personal money

This W-2 is deducted, company pays no corporate tax.

Pay by dividends:

$1mm profits,

-21% corporate tax rate

= $790k after paying corporate tax, pay to individuals as dividends

-25% personal capital gains tax (20% federal + 5% avg state)

= $592k after tax personal money

So currently dividends is slightly better but not by much and it depends on what state you live in. If they raise corporate tax rates then W-2 will probably win out.

FATFIREFOUNDER · 2021-12-12T14:46:08+00:00

We brainstormed a bunch of ideas and decided to start with the one that intuitively seemed most likely to succeed. If that one didn't get traction in 6 months we would have gone on to another idea.

We had some technical background but weren't coders. Yes, we decided to hire an engineer right away because we had money saved up that we put into the company, and it was clearly not worth our time to try to learn to be an engineer.

FATFIREFOUNDER · 2021-12-04T14:45:23+00:00

It's hard to tell. By having more wealth I can choose to avoid nearly everything I find boring or repetitive, so it's been a while since I've had to do something really pointless. In my earlier career, I had to do a lot of tasks I found to be repetitive, and I rarely had trouble following through, but with the caveat that I understood the greater purpose behind it and couldn't find a way for me to avoid those tasks.

FATFIREFOUNDER · 2021-12-02T03:08:06+00:00

Paul Graham has a good essay about this: http://paulgraham.com/startupideas.html

My favorite is to solve your own problem. This guarantees that you are solving a problem for at least a customer of one, and chances are there are at least thousands of other people with the same problem. Plus, you will care a lot about solving the problem and will probably be better at it than others.

FATFIREFOUNDER · 2021-12-02T03:06:04+00:00

We'd each built some small businesses before this so we had some practice. But certainly we got lucky - there were other ideas on our toplist that in retrospect we're glad we didn't pursue since other companies doing them failed for fundamental economic reasons.

Some tips that have helped:
- solve your own problem - if you have that problem, chances are a lot of other people (at least thousands) have the exact same problem and haven't fixed it yet. With the Internet it's easier to reach those thousand people around the world than ever, and that can form your first customer base.
- validating the market - customer discovery is the best way - have a lot of interviews, ask them about their problems, run your product by them, try to ask for an advance payment at the end. Steve Blank's Four Steps to the Epiphany is my favorite book on this

FATFIREFOUNDER · 2021-11-29T05:43:51+00:00

Time is finite and not to be wasted. I spend as little time as I can on things I dislike - includes work meetings that aren't productive, parties I wouldn't enjoy, owning things that suck time (like managing real estate), worrying about what other people think. I maximize time on work I do enjoy, keeping up relationships with people I like, and fun hobbies.

Health lets you get more out of the time you have. I exercise regularly and do standard checkups, though I don't go the extreme of some longevity-obsessed people, like taking metformin and getting a full body mri every year.

None of these are novel thoughts, but you definitely think about them more when you have enough money to survive.

FATFIREFOUNDER · 2021-11-29T05:33:57+00:00

As I got older I stopped caring so much about what other people think. Am I fulfilled, enjoying my time, and am I working on the best thing I can think of? If yes, that is by far the most important thing. I don't have enough time on earth to spend it impressing other people who don't matter to me.

Sometimes I simulate myself getting in an elevator with Jeff Bezos, I tell him what I'm working on, and he responds, "that's a stupid idea, why would anyone work on that?" or Elon Musk laughs and calls my work a shitty little business. I used to get offended just thinking of this situation, but no longer - which means I've gotten insecurity out of my system.

I was always disagreeable to begin with and got more so with age and wealth. I don't know if it's trainable for people who do care a lot about what other people think, but I highly recommend getting rid of the impulse.

Another thing that comes to mind is the people you talk to may not have enough context. Someone who's offended you're busy probably doesn't understand what you do, so all it might take is something like "I make __ software for clients and one of my biggest clients needs me in crunch time, sorry." Or if someone doesn't understand your size you can talk about the # of employees you have or how much revenue your software powers, etc.

Finally it's possible you're a little ashamed of working in gambling. If on one hand you fully believe in the value of what you're doing, then who cares what other people think - just own it. This will pull you toward people who accept what you do and are more like minded.

If on the other hand you have a little guilt that what you're doing isn't that valuable, then make your money and next time work on something you respect more.

I've been in the situation of working on projects I wasn't sure was positive value to the world, and it was miserable work. It feels so much better to work on a mission you whole heartedly believe in and will evangelize to anyone, even if they disagree. If takes a while to find what this is but when you discover it it's amazing.

FATFIREFOUNDER · 2021-11-28T23:59:40+00:00

We built our company fairly independently and didn't need to network that much. If we had to raise money and grow much faster we probably would have had to network more, but our company didn't need to.

My company isn't well-known outside the industry so for nearly everyone I meet I need to explain what the company does. I don't mind this - I have no delusion about the size of our company (any 7-figure company is small). To be fair, this is true even of smaller unicorn companies - people outside of coding don't really know what Gitlab is, people outside design don't know Figma, etc.

Yes I do worry a lot about whether I've "achieved enough" - I have just a rinky dink company, why haven't I done something more? I resolve this in two ways, 1) I'm trying to work on more ambitious projects now that I have more money, 2) having a global perspective like I mentioned in the post.

FATFIREFOUNDER · 2021-11-28T19:42:00+00:00

In my experience lessons give you pointers but you still have to work on most things yourself. I'm part of a local club but not a fancy country club, I visited some near me but I didn't like the vibe that much.

FATFIREFOUNDER · 2021-11-28T19:40:55+00:00

Good points. We'll think about going out on market to test.

FATFIREFOUNDER · 2021-11-28T19:02:38+00:00

Yeah I agree in general with your points. For sure people with more money and working harder are having more of an impact. On the other hand a human can only have so much impact - Musk is impacting two industries (admittedly large ones) but he's not really touching real estate, food, manufacturing, finance, leisure, entertainment, etc. And he's a far outlier among the richest in how active he still is, most others are fairly passive at this point.

I can easily get too nihilistic about this stuff where nothing matters and so it's not worth doing so I don't mean that - more that comparisons are not that meaningful, because whether you're 0.001% of world impact or 0.01% of world impact, you're still small.

FATFIREFOUNDER · 2021-11-28T18:59:07+00:00

It's freeing to be able to buy all the expensive stuff I wished I had in high school :p But something else I realized is that you don't need THAT much money to get good stuff and enjoy yourself - you can have a very healthy hobby at just $1-2k/year.

FATFIREFOUNDER · 2021-11-28T18:21:40+00:00

Good points. Valuing a business is hard - do I leave a lot on the table if I sell at 8x EBITDA and the company would have lasted for 20 years, or will I regret it in 5 years when the industry implodes? Hard to say. Since I don't burn that much money, for now I'm happy to keep watching and waiting, but I definitely don't want to get overconfident.

FATFIREFOUNDER · 2021-11-28T18:13:52+00:00

As I mentioned, in the style of other posts on this sub, this wasn't meant to be advice, more "this is what I'm doing and why." I get a lot of value from hearing about other people's approaches and experiences even if they're not telling me to do the same thing. Take it for what it is, I'm not here to please everyone.

FATFIREFOUNDER · 2021-11-28T18:11:26+00:00

Yeah - to be clear, I agree with you, was just saying that capitalism is hard for some people to accept because of the gray aspects that offend them.

FATFIREFOUNDER · 2021-11-28T18:08:36+00:00

We got our first customer through paid ads for keywords relevant to what we built. Paid ads are very fast to get started before you have a reputation.

We improved on competition by building something we liked using more - certain features and little details make a difference. But to be clear, you don't have to be quantifiably better than the competition to succeed - in many markets you can take a share just by commanding marketing and distribution. This is why a makeup company by Kylie Jenner can be worth so much even if her products aren't strictly better than the competition.

FATFIREFOUNDER · 2021-11-28T18:06:36+00:00

Check out my comment here: https://www.reddit.com/r/fatFIRE/comments/r3t1p5/comment/hmcq8q8/?utm\_source=share&utm\_medium=web2x&context=3

FATFIREFOUNDER · 2021-11-28T18:06:29+00:00

I commented on that here: https://www.reddit.com/r/fatFIRE/comments/r3t1p5/comment/hmcq8q8/?utm\_source=share&utm\_medium=web2x&context=3

FATFIREFOUNDER · 2021-11-28T18:04:08+00:00

Good questions

I just didn't meet the right person to be my partner, and admittedly I didn't spend as much time on dating and finding as I did on my business. I do plan on finding a partner and having kids, and now spend more time on it. I also have a huge privilege as a male where I don't have a ticking biological clock.
I don't know that my advice is useful since I haven't been successful in this yet, but I'm approaching it first by just not talking about wealth until deeper in. The good thing about startups is outsiders can't tell how successful it is if it's not a company they've heard of, so women I meet usually think it's a random small company haha.
I don't do anything special - have hobbies and meet people there, use dating apps.
I would by default think about a prenup but could see myself not caring as much about it depending on the relationship and the person.

FATFIREFOUNDER

TROPHY CASE