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Derek Sivers and the Art of Enough (brendancahill.io)
182 points by Bcahill82 on Aug 1, 2020 | hide | past | favorite | 78 comments

Derek's writing influenced me quite a bit in the early 2000s. I bootstrapped a software business from zero to near $10m in annualized revenue, and sold it almost half a decade ago. I contributed 100% of my equity into a charitable remainder trust because I learned about that idea from his website.

Since then, I've done a lot of "puttering". I'm teaching myself jazz guitar, and I'm currently enrolled in law school. I have basically unlimited time to read whatever interests me. If I could go back five years and give myself some advice, I would say that "enough" is not durably satisfying. Purpose is durably satisfying. Purpose arises from constraints. Having "enough" means you lack a particular type of constraint. Thus, enough" can get in the way of developing purpose, particularly if you are somewhat undisciplined like me.

(Also, I would abolish charitable remainder trusts from the tax code. I created one for lifestyle reasons not tax reasons, but after experiencing the tax consequences firsthand, I think they are profoundly unfair.)

Wow cool! For those of us who don't regularly create charitable remainder trusts, what are the tax consequences and why are they unfair?

I had a bunch of equity in a startup that had a cost basis of, essentially, $0. Under normal circumstances, I would have sold this for $millions, and would have paid nearly 20% in capital gains taxes immediately.

Instead, I contributed my equity to a CRUT. I paid zero capital gains taxes at that moment, and the CRUT pays zero capital gains taxes ever. Also, because a contribution to the trust is a contribution in part to charity (with proportions calculated according to actuarial figures of my life expectancy), I got a charitable tax deduction of many million dollars which I was able to carry forward for many years.

Each year I owe taxes on the 5% which the CRUT distributes to me every year, but since this is capital gains income, it is taxed at a very low rate -- which is effectively reduced even further because it is offset by the charitable deduction which I have been able to carry forward.

The net effect is that I'm paying capital gains taxes in a tiny trickle over the remainder of my lifetime, and I also got a giant charitable deduction to offset those capital gains taxes. When I die, the principal in the trust goes to charity. The IRS will never get the kind of bite at this equity that I would intuitively expect it to get.

I don't understand how this capital gains tax loophole could be beneficial to society. I think it should be removed from the tax code.

Another side effect of the CRUT I hadn't anticipated: Occasionally, I note the intrusive thought that my continued life is the one and only barrier which is keeping a decent amount of capital from serving charitable purposes right now. That's honestly pretty depressing sometimes.

Thanks! I think I get it, but not fully yet: if you'd deplete the entire trust before dying, you'd have paid the same capital gains tax as you would've if you had not made the trust, correct? Just spread out over many years.

Why do you feel that it is a loophole if you pay the same, just at different times? (except over what you give to charity, but isn't charity untaxed pretty much across the board in the US?)

EDIT: by they way, yours is the first tax related comment that I recall reading that complains about unfair rules that are in your favour. Hats off, I had expected the opposite answer.

I came here to ask the same, @tkiley. It seems the main benefits of your CRUT are (a) deferring your capital gains taxes until later and (b) allowing you to make deductions for charitable giving. But ofc those come at a cost, namely that you don't get paid until later (5% yearly), and that you have to give to charity.

Can't anyone just give to charity and get a deduction? And doesn't everyone get taxed later when they're paid later?

You're right, a lot of the benefit is in deferring taxes to a later date. This deferral is quite valuable when you consider the time value of money and the fact that by spreading out $millions of gains over many decades, I get to put a lot more of the gains in a lower tax bracket, where if it all came in one year, it would basically all be taxed at 20%.

When you combine decades of deferral with the sizeable charitable deduction, it feels like double dipping. If putting equity in the crut only gave me one or the other (deferred taxation or a big deduction) that would seem intuitively fair. But both together? That feels absurd.

I'm not US based, but just curious.

What happens to that capital, is it just sitting in a bank account waiting to be dispensed?

Could you invest or loan it to other companies you control at market rate for other purposes?

A is super useful because normally if you sold your stock to diversify, you'd need to pay capital gains then. If you do it in a CRUT, you don't have to pay until later.

You also get an upfront deduction, which could be bigger (or smaller) than what the charity eventually gets.

Whether that's bad depends on how you feel about the way your government spends tax money. Because you used a CRUT, the money that doesn't support you will go to some worthy charity, instead of funding a series of wars, pervasive surveillance, and cages for kids.

Of course the government also does many worthwhile things, but your extra money will be spent entirely on worthwhile things, and not at all on horrific ones.

The problem with this thinking is that only those privileged enough to take advantage of it get to pick how their tax money is spent.

I disagree with (even despise) some of the ways government spends our money, but should I get to choose like some special snowflake while most don't have the same opportunity?

This just enforces a rigged economy... and guess what? Many of the privileged few would support government programs the rest of the so called democracy wouldn't.

Your tacit assumption is that wealthy individuals who can take advantage of bullshit tax favoritism will spend that extra money in worthwhile (subjective) ways.

I would certainly prefer a government that doesn't spend money on horrific things at all. It'd be great if I could pay my taxes without feeling dirty. I'm hopeful that maybe, with a lot of hard work and creativity, we'll manage to fix our democracy.

But in the meantime, I don't think there's anything morally wrong about legally reducing taxes and sending the money to charity instead. I'd even argue that, since privilege is an issue, we should expand this opportunity beyond the privileged few.

I'm criticising the system more than the individual. That being said, I've noticed that people will rail against big brother and all these rules and yet turn around and take advantage of any flaw in the system because they can (everyone else is doing it!). Proving that we need hyper-specific and cumbersome rules because no one is capable of policing themselves.

That's true! I'm happy that I am paying low taxes. It just seems ridiculous that my effective tax rate is so much lower than the effective tax rate paid by other people.

As best I can make out, a CRUT reduces your tax burden dramatically if 1) you are young, and 2) you fund the CRUT with equity that has a very low cost basis. I don't think the tax code should contain a special magic wand that reduces tax liability so low for this particular situation, because this advantage seems unfair to people who accrue their wealth over a lifetime by more traditional means.

Seems it'd be a substantial savings even if only (2) is true. A 55-year-old who's retiring a bit early after holding Amazon for twenty years could avoid a lot of capital gains.

Thanks for this detailed explanation - it matches the conclusions I had after some research into the matter (stimulated by Derek's sharing his experience!).

I don't think you should ever feel guilty or depressed for... not dying! Really. Think that, unlike most cases, when you will eventually die, instead of passing your large fortune to your heirs, it will all go to charity. That's beautiful, and nice, and better than what most people do. Feel proud of it.

Recently, I read back through some of my forum posts on HN and elsewhere from the past ten years. In hindsight, I see that I often erred on the side of harshness, and often conflated cynicism and intelligence. As I get older, I see increasing value in a bias toward kindness. Thank you for your kind words.

Well, you don't really "own" capital, you've "just" earned an authorization to spend some amount per year. It's like a debit card thats auto refilled every year. In the meantime "your" capital is being invested and reinvested by various firms. If you owned a valuable lake and deprived others from using it while you're alive, that would be a different story. But money? Meh, those are completely virtual constructs.

I think a big donation like your's to where you think it'll do the most good is far better for society than giving that money to the government.

So true! You literally are doing something immoral which is bad for society!

> I would abolish charitable remainder trusts from the tax code.

They've been reducing the scope of new trusts over time. When I looked into it around 2014, a young person couldn't actually make a lifetime income CRUT because the requirement for 5% distribution, and the low interest rates at the time made the actuarial calculations show a zero balance for the charity at the end, but you need to show at least 10% for the charity at the end. A fixed term just doesn't seem as good.

I ended up just paying federal cap gains and CA income on most of it, but I did donate some of the near $0 basis stock to a DAF, and sold a small portion of the equity after moving to WA. Some of that was QSBS which was nice, but having seen the 2001 stock market, leaving it undiversified to save on taxes didn't seem worth it.

They reduced the scope of new ones but leave old ones alone? Seems like it should apply to all or none.

Charitable remainder trusts are setup as irrevocable, if properly drafted. It would be difficult to equitably unwind them after the fact.

Changing how CRUTs are treated ex-post facto would also raise doubts about how Roth IRAs will be treated. There's already people who don't trust that the federal government will keep those tax free.

There are all sorts of decisions made based partially on taxes that the government later changes going forward. And those changes cause a ton of issues. Just seems like should all be one way or the other.

These things are grandfathered in.

What are the tax consequences that make it unfair?

It's weird to come to my favorite forum, and see my name in the title of a post.

It's weirder to read comments claiming to know about my personal life and motivations, though they're all wrong. (Both the good and the bad.)

The public me is not me - https://sivers.org/publicu - so I don't feel a great need to correct the errors here.

But thanks (tw04, lukego, marcinzm, s_a_p) for the reminder that anything I do can be spun negative.

There are so few famous people online that have been so giving with their time, willing to reply to every email.

I think your (public) actions speak volumes about who you are.

Your writing (and also whenever you’re interviewed on a podcast) has had a huge positive impact on me. I appreciate it and you (or at least the public persona of you).

Does anyone else find it frustrating when people talk about not working too hard and already having enough, after they have become wealthy?

That is why I usually try to avoid advice from people who (explicitly) give advice. It is better to observe what they do than what they say. Even if you wind up not enjoying the wealth, you’ll have understood it yourself and not be cursing yourself for not having tried. Except for life and death situations, and situations involving technical expertise, this applies to everything. Most of the time it is just our laziness selecting for examples of success that allow it to stay while reaping the benefits of working hard. A mind virus discouraging responsibility.

Wealth is relative, one can be a multimillionaire and still feel inferior to a billionaire. Even in billionaires, there is a ranking game.

Whatever. There's a big difference between feeling inadequate while sitting in your third vacation home and working 40-60 hours a week at a job you hate because if you were doing what you actually wanted to do instead you'd be starving in a ditch somewhere by now.

Probably the best predictor of if you're going to be upset about people having more than you if you've got $10M is if you're upset about people having more than you when you have $100k.

There will always be people who have cooler stuff than you. If you get upset about it when the cool stuff isn't like stable housing, food security, and decent transportation, the problem isn't lack of funds, it's your attitude.

agree, but we are not their audience. They want to signal to their fellow successful friends that they are humble.

For mortals like us, we have to be smart, work hard, persevere, etc. Life is a journey that I must do to my best ability.

What if, learning to be happy with "enough", is how people get filthy rich?


So what's the path from living with 4 other people working 40 hours a week at McDonald's to filthy rich? Haven't gone to college, don't have a skill that sets you apart (music/art/etc), and aren't particularly intelligent or scrappy. Seems to me there's literally no path from A to B.

MrMoneyMustache shows one path that a lot of people follow. It does involve redefining "filthy rich" along the way though so there's no Ferraris involved. https://www.mrmoneymustache.com/2013/02/22/getting-rich-from...

Well for McD's it's getting into management and going to McD school and then getting a franchise. McD's likes to promote from within. There are quite a few millionaires who have done this. I mean I am sure you have to work hard to do this and it isn't guaranteed either. I think a lot of franchised businesses can work this way.

I personally know of a husband and wife who own 8 franchises in a region and were able to send their children to the best schools in the world. High school education for the parents. They did exactly what you said.

If there's ever a time to do it it's when all of information is virtually free. Unfortunately this also means there are an equal amount of cheap distractions.

You understand there is a large swath of the human race that just isn't that intelligent right? Saying "but the information is free!!!" means absolutely NOTHING to someone who can't comprehend it.

That's ignoring the fact you expect them to decipher which information is accurate and inaccurate. How exactly do you expect someone who lacks critical thinking skills to determine who is telling them the truth and who is lying? The fact there are hundreds of thousands to millions of US citizens who believe in Q-Anon should tell you how flawed your logic is.

As you implied, it requires intelligence and a desire to achieve. So lazy dum dums are unlikely to be able to do it. Which sounds about right.

Watch Forrest Gump.

Different advice for different circumstances. Do you get upset when elite athletes talk about the importance of avoiding overtraining, when they have already become elite?

Apples and oranges my friend. Being elite and overtraining are orthogonal. By definition, overtraining is pushing your body too far too fast. No one can train for a 100 mile race by doing 3 50 mile training runs in a week. That's not how physiology works. Discipline and lots of hard work can help you be elite, but overtraining is never good. Never.

True, but a lot of novices use overtraining as an excuse to just not train. Actual overtraining is pretty hard to do for a typical weekend warrior.

> Being elite and overtraining are orthogonal.

Not really - it can take a serious lifter weeks to recover from a competition deadlift whereas a new lifter can recover in 1-2 days.

Well, it's not like you don't have enough money with Island et al...

(Yeah, I'm joking)

I get so many emails for him, people asking me to invest in their Soccer team or whatever.

Derek did not became wealthy. He gave the $22 million dollars he got from selling his company to a fund, and gets over $1000 each month, hardly "wealthy".

Derek has worked in a circus and knows how to live cheap enough. He also has lots of friends so he does not need to pay for lots of things.

I know people that earn in excess $10.000/month and spend it all or even get into debts.

Wikipedia disagrees:

>Derek Sivers transferred ownership of his company to a charitable remainder unitrust for music education, and had the trust sell it to Disc Makers. This agreement requires the trust to pay Sivers 5% of the trust's value annually (hypothetically $1,100,000 pretax, based on a sale price of $22 million as reported by Sivers)[4] until death, while upon death the remainder will ultimately go to charity.

So he actually earns around $90k per month. The foundation was also probably a tax dodge more than some altruistic thing.

He also acquired a second nationality, renounced US citizenship, and moved to a country that doesn't tax foreign sourced passive income. It's the most extreme example I've seen of planning your whole life around tax optimization.

Understandable though if you've read his book because he's had big problems with the IRS in the past and probably really wanted to show them his "FU money."

(I'd just like to acknowledge that my parent comment is pretty lousy. I don't know Derek and I'm making assumptions about his motives. I feel like it's fair game after his article "Why I gave my company to charity [1]" but I'm not proud of casting aspersions on internet celebrities. I have a jaded view of philanthropy and philanthropists that may be totally off in this case.)

[1] https://sivers.org/trust

I was under the impression that the US does not allow you to revoke your citizenship purely for tax reasons.

It doesn't but all that means is the form for renouncing has a checkbox asking "are you doing this for tax reasons"? And you check "no". Then during the consular interview you spew some line about how you no longer have attachments to the US -- "I haven't been back in over 3 years, own no property, let my driver's license expire" and you do have attachments in your new country "All my friends are here and I even spend Christmas here!"

It is more of a retroactive "if we find out later you lied we now have a legal basis to add extra penalties" but in practice nobody is really checking or cares. The underfunded IRS doesn't care about the tiny number renouncing and the consular officials doing the interview certainly don't care.

Even if the reality is in the middle, the likely difference between 1k a month claimed and 90k a month claimed surely puts him in the very wealthy category.

I agree with other posters, it’s a little annoying to have wildly successful people talk about “being happy with what you have” and “money isn’t that important” and “enough” etc.

While the concept is absolutely correct, and I believe “if you weren’t happy before hitting the lottery you probably won’t be happy after”, be successful independently twice then talk to me about how it’s done.

On the other hand, there are many wealthy people who are unhappy, with their wealth or otherwise.

I had the honor (but not the pleasure) of working closely with a guy whose personal wealth was estimated at half a billion or so, all self made. There was nothing he wanted he couldn’t afford. And yet he was incredibly unhappy almost all the time - I caught an occasional glimpse of happiness from him after he would come back from a weekend fishing alone, or when some-list-or-other of wealthy people bumped his rank up in their listings.

When someone like like Sivers says “I was happy before the money and money didn’t make me happier”, I believe him.

In fact, I’ve known many people who made fortunes, and quite a few who lost fortunes and some who lost family to terror attacks. Other than a transient effect after specific events (good or bad), everyone reverted to their pre-event happiness levels.

Having money is an incredible daily-stress reliever. But according to my life experience, it has very little effect on happiness.

This falls in line with studies that show when most people hit the upper middle class, more money doesn’t automatically equate to happier. And if someone doesn’t have a purpose beyond money, I could see more money making them less happy. “What do I do now?”

I actually know Derek in real life (although not very well). He gave away most of his wealth, but he still draws a very comfortable salary from the fund he set up with the wealth that remains. He's rich.

I'm not sure where you heard the $1k/month figure, but there's no way he possibly makes that little. He lives in Oxford, possibly the most expensive city in the UK outside of London. $1k/month in Oxford isn't enough to rent a one-bedroom flat, without even considering other living expenses - there's no way he lives in Oxford on an income that low.

$22 million dollars is not "hardly wealthy". It's filthy rich.

He gave those $22 million away. That is the point.

He didn't, he siphoned them in a "charity/fund" for tax purposes. That's a rich man's move 101. It only becomes an actual charity if he (knock on wood) dies young from my understanding...

He didn't give it away, he put it in a foundation that pays him 5% per year and probably avoided paying taxes on it as a result.

Derek and his writing used to be a frequent top page link on HN. When I first started reading them I found them inspirational. As I read more of his writing I got the impression that most of the things he did were presented in the light of “I’m just a simple person that doesn’t need a lot” type of minimalism. However if you look at his “charity” he seems to have just figured out a way to avoid taxation and keep most if not all of his CD Baby exit. Additionally despite using what was the .com boom environment of the late 90s and early 2000s to generate his wealth I believe he has renounced his US citizenship and lives abroad now. I don’t care that he did that really, it just seems that his public persona is a bit of an act and hides a bit of entitlement/petulance.

I'm only going off of what I heard in his interviews, and talks throughout the years, and I admit I'm def a bit of a fanboy of his.

But regarding the charity, from reading your comment I thought maybe this was another case of don't seek your heroes. Here's what he says about it: “Independent Musicians Charitable Remainder Unitrust.” When I die, all of its assets will go to music education. But while I’m alive, it pays out 5% of its value per year to me.

(Note: 5% is the minimum allowed by law. It’s still too much. I would have preferred 1%, but oh well. I’m free to use it to start new businesses to help people, or whatever.)

The trust has 8.8M in assets. http://www.nonprofitfacts.com/WA/Independent-Musicians-Chari...

I really don't see a problem with 400k/year tbh, and if you believe him, 100k a year. And I wouldn't define "giving up the assets on death" as "keeping" either.

The dude says on interviews that he lives in a house with pretty much no furniture, and has an empty fridge. He himself knows it's fucking nuts and doesn't prescribe it to anyone. It's just his weird schtick and it seems to be genuine to me.

Could this be a huge act to play up a persona? Maybe. But the guy's been pretty consistent throughout the years and appears to practice what he preaches. Any interaction I've had with him has been totally consistent as well.

“I don’t need a lot” isn’t mutually exclusive with “I don’t want to pay a lot in taxes”. Besides that, he lives in New Zealand where everything costs twice as much. Sounds like your crediting his success solely on being at the right place at the right time. I got news for you - that’s pretty much all success or a component of it. Not to mention, he did build a sustainable business that gave independent artists an outlet to distribute their music. I’d say the guy is a saint.

When I emailed him in March he said that he left Singapore for England because he wanted his son to grow up near nature.

I remember when I was in college trying to figure out what to shoot for in life, I had the realization that if you shoot for "more" it's a goal you'll never reach. There is no end to it.

But if you shoot for "enough", there is a very definite point between "more than enough" and "not enough".

It's a nice goal to shoot for. When you are above "enough", it means you can relax and enjoy life.

But then you have to answer the question of what makes you happy. For some people buying an ocean front house and fishing or playing golf all day is the answer. But for the successful entrepreneur type that isn't "enough" usually

> But then you have to answer the question of what makes you happy.

Self-introspection and awareness are helpful basically always, in my opinion.

If you don't know what you want, you'll never be satisfied.

That #10.5 point really resonates with me. Especially now with all of this isolation, it’s become very apparent that almost all communication on the internet is the screaming from inside the car type instead of the real human connection type. I made https://otherrs.com/ as an experiment to see if I could drum up more of that second type

> now living in New Zealand

Derek does not live in New Zealand anymore. He moved to England some time ago (perhaps 1 or 1.5 years ago?)

According to his website he moved back to New Zealand this year.

Ouch, missed it. My bad.

Just listened to this episode in [The Knowledge Project with Shane Parrish] podcast.

#88 Derek Sivers: Innovation Versus Imitation

Like anything else in life this piece has good parts and not-so-awesome parts.

My opinion: take the good and forget the rest.

If I can draw the line on what is enough for me, I can lead a life that is happier and free of divisive depression that comes from comparing myself to others.

"I became rich when I earned more than I spent" are words spoken by a rich man with 0 self awareness. I can tell you the second my life became infinitely less stressful: when I paid off my student loans.

I too spent almost no money, went on almost no trips, and lived way, way below my means to make it happen in my 20s. It turns out as my income has increased my happiness has increased - and I'd agree with all the studies of once you cross a certain threshold in the 6-figure range that more money means "less". Generally it just means: I have nicer versions of the same things.

All that is to say: I sure as hell wasn't "rich" when I was making more than I owed each month, not even close. And I don't believe for a SECOND Derek would be happy going back to living in a flat with 3 other people, eating peanut butter sandwiches 3 days a week but "making more than he spends", which is what he implies.

Derek: there are people out there who are in their 50s who would still have to live with 3 other people and eat peanut butter sandwiches 5 days a week to earn more than they spend. THAT'S THE POINT. Maybe if I make $90k/month some day I'll also be blind to the reality of the common man, but I can still see it from this little perch I'm sitting on at the bottom of the mountain.

I think it is noble to preach being rich in the moment. I think for Derek quitting his job in his 20s to play music full time was for sure a mark of affluence in his social circle at the time.

There should be some qualification, like "once you earn above $100,000, then you become rich when you earn more than you spend". Even that wouldn't be quite right for many expensive cities.

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