Should I take a payout in Bitcoin? (1 Viewer)

trever

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So I won a pretty large bet (2017 is already better than 2016!) and the loser will pay me in either cash or Bitcoin, but is offering me a small bonus if I take the Bitcoin option.

I get the general theory of what Bitcoin is and how it works, but have zero understanding of the practical aspects of setting up a wallet and actually spending it.

Once you get Bitcoin, how hard is it to spend, is the hassle and transfer/exchange cost (if any??) worth it?

Just for arguments sake, let's assume that this isn't just a one time thing.
 
Bitcoin carries a host of problems but it comes with the benefit of privacy {maybe}.

Bitcoin transactions are individually taxable - you should report them on your tax return as if they are shares of stocks. You will need to match sales with purchases. Every time you convert Bitcoins to cash or merchandise there should be a matching line on your tax return. Of course you can ignore this advice, but the consequences could be severe.

Bitcoin is not so easy to use. There is a reason you are being offered bitcoins at a discount to cash. It has been getting easier to use Bitcoin, but "easier" does not mean "easy".

Bitcoin valuations are volatile. This can be good or bad depending on the direction of the market.

Bitcoin has no one standing behind the asset. Maybe things will be ok, maybe the whole thing is a sophisticated fraud. Let the buyer beware.

The best thing about Bitcoin is being able to purchase illegal / dodgy things and services without leaving a cash trail {maybe}. Of course a pile of hundred dollar bills can serve the same function.

I wouldn't take the Bitcoins. Even if the offer was wonderful, I'd have to fear that I was being scammed and was too unsophisticated to figure out I was being screwed.

However, I would take payment in the form of vintage casino chips -=- DrStrange
 
As stated earlier, unless you have more than a passing familiarity with Bitcoins, or the "bonus" is quite significant, I would stick with a cash payment.
 
i wouldn't

895795
 
I would accept the bitcoins.

You could get passed counterfeit dollars, or one of you could lose the dollars in transit. There's risks either way. And legally, you're supposed to report the net gambling winnings as income, not matter what form they come in.

If you're planning to immediately change the coins to dollars, you don't really have much risk of gaining/losing money because of price change - but if you hang onto the coins for a few days, you may see a real price difference. It's been on a tear lately - Bitcoin was around $900 on Christmas, rose to the high $1100's on January 5th, plummeted to $834 on rumors the Chinese government was going to ban it, and has been recovering because China put out a statement saying it's not banned, it just shouldn't be used as cash - they consider it a commodity and gains/losses should be reported as if it were any other commodity.

Whether it's bitcoin or dollars, you are technically liable to pay tax on the winnings as "income" in one way or another. If you took your payment in ounce of gold, it would be the same deal - for tax purposes, you can pretend it's gold and you'll be doing the right accounting.

If it were cash being transferred electronically, there's no less of a record than if you accepted bitcoins into an account at, say, Coinbase.

You can open an account at Coinbase, have the friend transfer coin into your your wallet at Coinbase, and you'll be certain the coins are good and that the friend can't reverse the transaction. Then you can sell the coins for dollars through Coinbase; they take a 1.5% fee if you put the dollars directly into a cash account with them or into a regular US bank account, or they take a 4% fee if you put the dollars into a PayPal account. The money going into any of those accounts would, of course, leave an electronic paper trail.

If the cash were being transferred hand to hand, of course, there'd be no record with your name on it (or theirs.) You can look to see whether there are Bitcoin ATMs anywhere near you. If so, you can open a bitcoin wallet anywhere, or establish your own with software. Then you have you friend transfer the bitcoin to you, and then you go to the bitcoin ATM to pull out the cash. This won't leave an electronic trail of any kind, other than the fact that it hits your bitcoin wallet - which doesn't have to be connected to your name in any way.

Basically, bitcoin behaves like electronic cash. Just like paper cash, it leave an electronic trail going into or out of your accounts.

Your friend may be offering you a bonus if you take the payment in bitcoin because he won't create an electronic paper trail showing that he made a profit on the coin. If he cashes his coin, he's supposed to pay income tax (if he mined them) or should pay capital gains (if he bought them cheaper and sold them higher.) Again, same accounting as if he were offering gold that he had mined himself, or that he had bought back when gold was only $600 an ounce. If he needs to sell coins to have the cash to pay you, but doesn't want to report the income, sending you the coin directly will cost him a lot less.

If you want to keep the bitcoins as bitcoins - and speculate on whether they'll go up or down in value - just leave them in your wallet. (But a personal wallet, not a wallet on a bitcoin exchange site. You don't want to worry about what happens if the site goes down next month or next year, so only move your coin to an exchange site when you're ready to exchange coins for dollars, or vice-versa.) Bitcoins have been very volatile of late, but seem to be on an upswing whenever there isn't a momentary panic for one reason or another. After the latest China scare, it has risen back to the $900 range where it was at Christmas... but back in October, it was closer in the low $600's range. While bitcoin is in your coin wallet, it's like a commodity that has the volatility of a high-volatility stock, because the environment keeps evolving... but if you convert it to cash in the same hour as you receive it, you're in no real risk.

https://coinmarketcap.com/currencies/bitcoin/#charts

There is a reason you are being offered bitcoins at a discount to cash. It has been getting easier to use Bitcoin, but "easier" does not mean "easy".

Actually, if he already has the bitcoins, paying with them is ridiculously easy, for him. That's not a reason to offer bonus. More likely, he's sitting on a capital gain on the coins and doesn't want to report it, and using the coin to settle a gambling debt allows him to do just that.

Bitcoin to much baggage

I think it comes with the same amount of baggage as US Dollars - but we're all very familiar with the baggage of US Dollars, and most of us are not familiar with the baggage of Bitcoins. For example, if my apartment building burns down, my bitcoins are fine... but I'll lose my poker roll, which is US Dollars!
 
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I would accept the bitcoins.

You could get passed counterfeit dollars, or one of you could lose the dollars in transit. There's risks either way. And legally, you're supposed to report the net gambling winnings as income, not matter what form they come in.

If you're planning to immediately change the coins to dollars, you don't really have much risk of gaining/losing money because of price change - but if you hang onto the coins for a few days, you may see a real price difference. It's been on a tear lately - Bitcoin was around $900 on Christmas, rose to the high $1100's on January 5th, plummeted to $834 on rumors the Chinese government was going to ban it, and has been recovering because China put out a statement saying it's not banned, it just shouldn't be used as cash - they consider it a commodity and gains/losses should be reported as if it were any other commodity.

Whether it's bitcoin or dollars, you are technically liable to pay tax on the winnings as "income" in one way or another. If you took your payment in ounce of gold, it would be the same deal - for tax purposes, you can pretend it's gold and you'll be doing the right accounting.

If it were cash being transferred electronically, there's no less of a record than if you accepted bitcoins into an account at, say, Coinbase.

You can open an account at Coinbase, have the friend transfer coin into your your wallet at Coinbase, and you'll be certain the coins are good and that the friend can't reverse the transaction. Then you can sell the coins for dollars through Coinbase; they take a 1.5% fee if you put the dollars directly into a cash account with them or into a regular US bank account, or they take a 4% fee if you put the dollars into a PayPal account. The money going into any of those accounts would, of course, leave an electronic paper trail.

If the cash were being transferred hand to hand, of course, there'd be no record with your name on it (or theirs.) You can look to see whether there are Bitcoin ATMs anywhere near you. If so, you can open a bitcoin wallet anywhere, or establish your own with software. Then you have you friend transfer the bitcoin to you, and then you go to the bitcoin ATM to pull out the cash. This won't leave an electronic trail of any kind, other than the fact that it hits your bitcoin wallet - which doesn't have to be connected to your name in any way.

Basically, bitcoin behaves like electronic cash. Just like paper cash, it leave an electronic trail going into or out of your accounts.

Your friend may be offering you a bonus if you take the payment in bitcoin because he won't create an electronic paper trail showing that he made a profit on the coin. If he cashes his coin, he's supposed to pay income tax (if he mined them) or should pay capital gains (if he bought them cheaper and sold them higher.) Again, same accounting as if he were offering gold that he had mined himself, or that he had bought back when gold was only $600 an ounce. If he needs to sell coins to have the cash to pay you, but doesn't want to report the income, sending you the coin directly will cost him a lot less.

If you want to keep the bitcoins as bitcoins - and speculate on whether they'll go up or down in value - just leave them in your wallet. (But a personal wallet, not a wallet on a bitcoin exchange site. You don't want to worry about what happens if the site goes down next month or next year, so only move your coin to an exchange site when you're ready to exchange coins for dollars, or vice-versa.) Bitcoins have been very volatile of late, but seem to be on an upswing whenever there isn't a momentary panic for one reason or another. After the latest China scare, it has risen back to the $900 range where it was at Christmas... but back in October, it was closer in the low $600's range. While bitcoin is in your coin wallet, it's like a commodity that has the volatility of a high-volatility stock, because the environment keeps evolving... but if you convert it to cash in the same hour as you receive it, you're in no real risk.

https://coinmarketcap.com/currencies/bitcoin/#charts



Actually, if he already has the bitcoins, paying with them is ridiculously easy, for him. That's not a reason to offer bonus. More likely, he's sitting on a capital gain on the coins and doesn't want to report it, and using the coin to settle a gambling debt allows him to do just that.



I think it comes with the same amount of baggage as US Dollars - but we're all very familiar with the baggage of US Dollars, and most of us are not familiar with the baggage of Bitcoins. For example, if my apartment building burns down, my bitcoins are fine... but I'll lose my poker roll, which is US Dollars!

Sorry, but you are a little too blase about the risks involved in the Bitcoins market. When these "markets" go down, Bitcoin owners have no recourse. Yes, if he keeps them in a wallet they do not disappear, but their value van be decimated instantly. What you mention about China is a small example. There have been other, more severe, impacts.
 
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It would have to be a substantial bump to take something that I would need to
  1. Set up a Bitcoin Wallet
  2. Cover the fees to transfer it to PayPal or
  3. Find a BitCoin ATM, and drive there
  4. Gambol on the value of BitCoins while handling 1-3
  5. Finally turn my BitCoin into cash.
As opposed to
  1. Get cash
 
If you're new to the world of virtual currency and you don't have much interest in learning more. Stay with cash.
 
I would accept the bitcoins.

You could get passed counterfeit dollars, or one of you could lose the dollars in transit. There's risks either way. And legally, you're supposed to report the net gambling winnings as income, not matter what form they come in.

If you're planning to immediately change the coins to dollars, you don't really have much risk of gaining/losing money because of price change - but if you hang onto the coins for a few days, you may see a real price difference. It's been on a tear lately - Bitcoin was around $900 on Christmas, rose to the high $1100's on January 5th, plummeted to $834 on rumors the Chinese government was going to ban it, and has been recovering because China put out a statement saying it's not banned, it just shouldn't be used as cash - they consider it a commodity and gains/losses should be reported as if it were any other commodity.

Whether it's bitcoin or dollars, you are technically liable to pay tax on the winnings as "income" in one way or another. If you took your payment in ounce of gold, it would be the same deal - for tax purposes, you can pretend it's gold and you'll be doing the right accounting.

If it were cash being transferred electronically, there's no less of a record than if you accepted bitcoins into an account at, say, Coinbase.

You can open an account at Coinbase, have the friend transfer coin into your your wallet at Coinbase, and you'll be certain the coins are good and that the friend can't reverse the transaction. Then you can sell the coins for dollars through Coinbase; they take a 1.5% fee if you put the dollars directly into a cash account with them or into a regular US bank account, or they take a 4% fee if you put the dollars into a PayPal account. The money going into any of those accounts would, of course, leave an electronic paper trail.

If the cash were being transferred hand to hand, of course, there'd be no record with your name on it (or theirs.) You can look to see whether there are Bitcoin ATMs anywhere near you. If so, you can open a bitcoin wallet anywhere, or establish your own with software. Then you have you friend transfer the bitcoin to you, and then you go to the bitcoin ATM to pull out the cash. This won't leave an electronic trail of any kind, other than the fact that it hits your bitcoin wallet - which doesn't have to be connected to your name in any way.

Basically, bitcoin behaves like electronic cash. Just like paper cash, it leave an electronic trail going into or out of your accounts.

Your friend may be offering you a bonus if you take the payment in bitcoin because he won't create an electronic paper trail showing that he made a profit on the coin. If he cashes his coin, he's supposed to pay income tax (if he mined them) or should pay capital gains (if he bought them cheaper and sold them higher.) Again, same accounting as if he were offering gold that he had mined himself, or that he had bought back when gold was only $600 an ounce. If he needs to sell coins to have the cash to pay you, but doesn't want to report the income, sending you the coin directly will cost him a lot less.

If you want to keep the bitcoins as bitcoins - and speculate on whether they'll go up or down in value - just leave them in your wallet. (But a personal wallet, not a wallet on a bitcoin exchange site. You don't want to worry about what happens if the site goes down next month or next year, so only move your coin to an exchange site when you're ready to exchange coins for dollars, or vice-versa.) Bitcoins have been very volatile of late, but seem to be on an upswing whenever there isn't a momentary panic for one reason or another. After the latest China scare, it has risen back to the $900 range where it was at Christmas... but back in October, it was closer in the low $600's range. While bitcoin is in your coin wallet, it's like a commodity that has the volatility of a high-volatility stock, because the environment keeps evolving... but if you convert it to cash in the same hour as you receive it, you're in no real risk.

https://coinmarketcap.com/currencies/bitcoin/#charts



Actually, if he already has the bitcoins, paying with them is ridiculously easy, for him. That's not a reason to offer bonus. More likely, he's sitting on a capital gain on the coins and doesn't want to report it, and using the coin to settle a gambling debt allows him to do just that.



I think it comes with the same amount of baggage as US Dollars - but we're all very familiar with the baggage of US Dollars, and most of us are not familiar with the baggage of Bitcoins. For example, if my apartment building burns down, my bitcoins are fine... but I'll lose my poker roll, which is US Dollars!

Saying there are "risks either way" and that using US currency "comes with the same amount of baggage" as bitcoins is totally insane advice someone who comes with @trever's question with the background of no experience whatsoever with bitcoin.

Just take the cash unless you have any reason apart from this to get involved in bitcoins.
 
Saying there are "risks either way" and that using US currency "comes with the same amount of baggage" as bitcoins is totally insane advice someone who comes with @trever's question with the background of no experience whatsoever with bitcoin.

Just take the cash unless you have any reason apart from this to get involved in bitcoins.

He said, in the OP,

Just for arguments sake, let's assume that this isn't just a one time thing.

That sounds like he has reason or interest to get involved. If we're talking about a couple houndred or couple thousand dollars, and he's OK with an electronic deposit into his account, the answer to this question is straighforward:

Once you get Bitcoin, how hard is it to spend, is the hassle and transfer/exchange cost (if any??) worth it?

You can easily open an account with a place like Coinbase linked to your checking account. You accept a deposit in bitcoin, you change it for cash in the next few minutes or hours, you deposit the cash into your checking account. 1.5% charge.

Spending it to buy things is less simple... but spending it to make/take bets with that same other party? Very simple, and much safer than doing so with cash.

As to whether I'm "totally insane" in my assessment of risks... I think the "risks" most people claim about bitcoin are the insane part, and the "safety" of cash is not nearly what most people think. It's kinda like fears of death... peoples top fears include airplane crashes, shark attacks, being murdered, falling to death, natural disasters... what are the likely causes of death? The actual annual deaths from tobacco, poor diet/activity, alcohol, infections, poisons, and automobile crashes each dwarf the collective numbers of what people fear most. We're simply used to car rides, and so we don't fear them, despite high risk.

There have been 38 deaths by shark attack in recorded in the US in a hundred-year span; 40,000 to 50,000 people die in car crashes every year.

I feel like bitcoin are in the same boat, today. People talk about this fear, that fear... and completely dismiss all the risks inherent in cash transactions.
 
As far as the risk of keeping it as bitcoin, as opposed converting it to cash, consider the history of the past three years...

What if he received a $1000 payment from winning a bet every week, and held onto if for seven days before selling it for cash? So, roughly every seven days, he gets $100 in bitcoin, but he also sell bitcoin acquired a week earlier, based on what $100 would buy a week ago...

Would he be ahead, or behind, because of being so slow to change his coin to cash?

The answer is he'll probably be ahead.

As I write, bitcoin is about $900.
If he had the bad luck to have started doing this on Jan 4th, 2017, when bitcoin was $1,100, he'd be down about $180.
If he had the bad luck to have started doing this on Jan 6th, 2014, when bitcoin was $975, he'd be down about $76.
If he started on pretty much any other day than those two dates, he'd be ahead.

For example, if he started on Feb 7th, 2015, when it was $228, he'd be ahead by about $2,900.
That was the case for most of 2015.
If he started in late 2014 when the price was $500, he'd be head by $1,000.
If he started in early 2016 when the price was $500, he'd be ahead by $1,000.

And that assumes he always had always been keeping roughly $1,000 in bitcoin... if he had been cashing it all out, he'd probably have gained/lost nothing on the carry, but more likely gained a few bucks than lost.

Here's a bitcoin price chart of the past 36 months; you can see that I featured the two absolutely worst dates to come in:

upload_2017-1-9_17-44-31.png



Am I saying he should invest in bitcoin? No, I'm not. It would pretty much be a gamble, like any other speculative investment.

But am I saying he shouldn't be radically afeared of bitcoin crashing from $1000 to $1 during the the hour or two that he has a bitcoin to sell because he accepted it? Yes, I am. I don't think that fear is reasonable.

And if his betting counterparty is interested in making/taking future bets in bitcoin, well - bitcoin can work out really well.

To be honest, I don't know if we're talking $100 bets, $1000 bets, or $10,000 bets.... but if we're talking $10,000 bets, I'd personally feel much safer taking bitcoin than taking cash.
 
Bitcoin, unlike automobiles, are not required to succeed in modern life. Sure, we take risks daily, and very few of us will survive all of those risks. I'm not saying he should or shouldn't take the payout in bitcoin, but there is an extra hassle (new account) and extra risks (any account linked to your bank account exposes you to a new hack). It really depends on what the extra "bump" is. 5%? 10%? 50%? These are mitigating factors.

As for any money "invested" in Bitcoin: I understand it could pay off big. However, when asked for advice (as the OP did) I would always advise against any investment with zero capital backing it. $100 in Bitcoin is $100 worth of digital nothing. No building, no business, nothing. It's your money, but don't pretend it's a speculative "investment". Bitcoins are worthless bits of nothing, with an artificially high value attached to them, like Beanie-Babies or poker chips - though Beanie Babies and poker chips have at least some value in that they are actual objects. Bitcoins are actually nothing.
 
Bitcoin, unlike automobiles, are not required to succeed in modern life. Sure, we take risks daily, and very few of us will survive all of those risks. I'm not saying he should or shouldn't take the payout in bitcoin, but there is an extra hassle (new account) and extra risks (any account linked to your bank account exposes you to a new hack). It really depends on what the extra "bump" is. 5%? 10%? 50%? These are mitigating factors.

As for any money "invested" in Bitcoin: I understand it could pay off big. However, when asked for advice (as the OP did) I would always advise against any investment with zero capital backing it. $100 in Bitcoin is $100 worth of digital nothing. No building, no business, nothing. It's your money, but don't pretend it's a speculative "investment". Bitcoins are worthless bits of nothing, with an artificially high value attached to them, like Beanie-Babies or poker chips - though Beanie Babies and poker chips have at least some value in that they are actual objects. Bitcoins are actually nothing.

But you could lose a dollar bill so obviously the risk is even on either side.
 
No building, no business, nothing. It's your money, but don't pretend it's a speculative "investment". Bitcoins are worthless bits of nothing, with an artificially high value attached to them, like Beanie-Babies or poker chips - though Beanie Babies and poker chips have at least some value in that they are actual objects. Bitcoins are actually nothing.

So, they're like dollars, then?
 
So, they're like dollars, then?

Sort of. However, as an American, the US Dollar is one of the risks I must take, much like driving a car. Bitcoins are far, far, more risky. It is assuming a risk you don't need to take - like driving a motorcycle instead of driving something with 4 wheels and an impact safety system.

If my work (which claims to be "Green friendly") offered me a 10% pay bonus to drive a fuel efficient motorcycle into work every day, I would decline. The risk does not equal the reward. If they offered a 50% pay increase, I'd be out shopping for a leather riding suit today.

It's all about what the pay bump is. Bitcoin is stupid (like riding a motorcycle), but it can be fun (like riding a motorcycle).
 
So, they're like dollars, then?

Yes, exactly the same. For instance, if someone stole your dollars you would report it to the local police where you live and the police would investigate who stole your money. Similarly, if you went to your local police and told them someone had stolen your bitcoins, they would be completely prepared to investigate the theft and understand what the fuck you're talking about.
 
Yes, exactly the same. For instance, if someone stole your dollars you would report it to the local police where you live and the police would investigate who stole your money. Similarly, if you went to your local police and told them someone had stolen your bitcoins, they would be completely prepared to investigate the theft and understand what the fuck you're talking about.

So, if someone used my bank account to steal money, or used my credit cards to steal money, I'd report it to the police, who have people competent with electronic thefts, wire fraud, etc., but if it's bitcoin, nobody is able to investigate.

Meanwhile... if someone snatches my bag of money, and it's not on camera (or even if it is), how high are the odds of the criminal being caught and me getting my money back? From experience of those around me, it's basically, "oh, cash? We're never gonna find it." Better odds of recovering an iPhone.

And if you do call the police about your missing bag of money, and they ask why you had a bag of money? What if you're in one of the five states that outlaw all forms of private gambling?

Or what if you're pulled over for a traffic violation, and the police officer finds your bag of money? http://www.washingtonpost.com/sf/investigative/2014/09/08/they-fought-the-law-who-won/
 
the US Dollar is one of the risks I must take, much like driving a car. Bitcoins are far, far, more risky.

What was the source of the large sum of money, again? Oh, yeah, @trever made and won a large bet. But bitcoin would be risky, because having bitcoin for a day before it could be turned to cash might cause him to gain or lose 2%.

I'm a bit surprised to find a site full of poker players feel bitcoin is such a risky holding. Am I the only one who sees any risk in carrying large sums of cash? I mean, I've never been mugged - I don't look like a victim, being 6'5" and 225 pounds and alert, but I still feel like it's risky to carry a large sum unless it's really necessary.

The biggest cash sum I've carried in recent years was 13 months ago, when I picked up a case of 1,000 dollar coins at the bank for packing into Christmas gifts.
 
So, if someone used my bank account to steal money, or used my credit cards to steal money, I'd report it to the police, who have people competent with electronic thefts, wire fraud, etc., but if it's bitcoin, nobody is able to investigate.

Meanwhile... if someone snatches my bag of money, and it's not on camera (or even if it is), how high are the odds of the criminal being caught and me getting my money back? From experience of those around me, it's basically, "oh, cash? We're never gonna find it." Better odds of recovering an iPhone.

And if you do call the police about your missing bag of money, and they ask why you had a bag of money? What if you're in one of the five states that outlaw all forms of private gambling?

Or what if you're pulled over for a traffic violation, and the police officer finds your bag of money? http://www.washingtonpost.com/sf/investigative/2014/09/08/they-fought-the-law-who-won/

The risks associated with using US currency and electronic currency aren't remotely similar. This is obvious to everyone. Even proponents of electronic currency recognize this. But instead of accepting this most obvious fact and simply explaining the value of electronic currency in a way that might encourage people to accept that risk, you have decided to remain obtuse to the point of being delusional.
 
The risks associated with using US currency and electronic currency aren't remotely similar. This is obvious to everyone.

It's obvious to me that they're not similar in the types of risks they bear. I don't deny that: holding dollars only exposes you only to small, inflationary risk, while holding bitcoin exposes you to wild speculative risk. However, holding bitcoin in a wallet puts you at very small risk of theft or loss due to accident, while holding dollars puts you at much higher risk of both of those. When going down the street, I have no concern about losing my account balances of any kind, but I do have concern if I'm carrying a large amount of cash.

But if we're just talking about taking winnings in the form of Bitcoin, and cashing it out, the risk of "holding" bitcoin as a speculative asset are moot. It's just being used as a way to transfer the money without carrying cash. Does that not make any sense to you?

And one can't, either intentionally or accidentally, pass a counterfeit bitcoin. But I've gotten a counterfeit bill.

Meanwhile in Virginia:
https://www.washingtonpost.com/news...ash-terrifies-players/?utm_term=.0ef77593db73
 
I think the focus is on the wrong priorities. Here are the things that I think are of greatest importance

There is the friction that comes from learning about and setting up the Bitcoin account and then figuring how to get cashed out. I recall my first exposure to NetTeller and PayPal were a little daunting (and PayPal's unsavory reputation at the time regarding frozen accounts). If this were a one time transaction for a $20 buck tip, it isn't worth the effort to me.

There is the extra level of tax compliance risk that comes with the use of Bitcoin. If the OP follows the tax code about gambling winnings, then the risk is not an issue. Many people don't comply with the letter of the law, in which case the problem is more difficult. The size of the transaction is also important - a really big win being converted from Bitcoin to cash via the banking system will create report(s) to the authorities which will almost force OP to properly file his taxes - both for the gambling income and the capital gain/loss from the bitcoin transaction.

There is also the question about making the guy paying off the bet happy. It could be that doing what is best to keep in the good graces of this person is the most important factor of all.

On the other hand, the OP doesn't really say precisely what is going on. If this is a transaction with a bookie or similar sort of character, then OP needs to consider the risks of non-compliance to be heightened.

I do not see the risk of Bitcoin volatility to be much of an issue if OP converts to cash ASAP. For the record, I don't see the risk of physical theft of paper money to be a significant risk either.

I will feel a bit silly if we are actually talking about paying off a $175 football pool bet -=- DrStrange
 
I am not a fan of memes. But this Susan Powter pic pretty much made my day.

Then it's truly your lucky day. You can enjoy this one guilt free because it's not a meme; it's simply a photo of motivational guru Susan Powter.
 

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