Just looking for some investing advice here.

I've received an offer from a legal new jersey sportsbook VIP host for an unlimited 50% deposit bonus match with only a 1x rollover. I've been doing these kinds of bonuses for years and believe this offer and the casino are legit and that my money would be safe with them. It should be worth a quick ~47.5% gain on average if I can break even making small sports bets. It's pretty damn close to a sure thing and guaranteed profit.

The question is, to what extent should I go all-in for this promotion? My first instinct is to try to sell every asset I have and borrow as much as I can and put every last penny into this deal, but then I started thinking about the tax implications of selling off my stocks/crypto and moving so much money around and now am second guessing myself.

I noticed Robinhood will let me withdraw about half the value of my holdings and plunge myself deep into margin. I would avoid being on the hook for capital gains taxes from selling all my stocks this way. Would that be a reasonable thing to do for this and then pay it off immediately after withdrawing? I don't know much about crypto loans but maybe that would be worth looking into as well to avoid paying taxes on those gains?

Or should I calm down and just deposit what I can scrape together without selling assets/taking loans? I have no family to look after and don't mind being aggressive with this stuff! What would you guys do in my situation?

Thanks!

what is the book?

ive heard a lot of caesars customers are having trouble getting their $5k freebet, they probably will eventually get it after they file with the gaming board but i would not deposit any $$ that you are not wanting to have tied up on the site for a long time.

Either they're idiots and going to default when people exploit this offer or they're scamming you. Either way I'd be wary of selling everything you have and going into debt... there is always some risk with other people holding your money whether you realize it or not. Especially with promo $ I've had so many people screwed out of their kickbacks after they lost @ casinos its ridiculous even some who had it in writing they tried to screwed and took time to get. I'd just do what you can scrape together tbh and expect a battle withdrawing the bonus especially after 1 bet tbh. Especially if you take both sides of the same bet.

With all due respect I don't really want to share the name of the site until I do the promotion so others won't do it before I have a chance and ruin my shot. After I do this I will say where it was.

But anyway, honestly guys I've been playing extensively on all the legal Jersey casinos/sportsbooks for a couple years now and I've never had a single issue getting paid or getting promotions sorted out. I know in the harsh world of offshore casinos it's wise to be cautious and fearful, but these Jersey sites who are regulated by the state have all been extremely trustworthy in my experience. So I appreciate the cautions but I'm really having a hard time worrying about the risk in that sense.

My main concern is maximizing this opportunity while minimizing extra costs like paying taxes on my stocks/cryptos etc...

I would never do something dumb like betting both sides of a game FYI.

As long as you fulfill your estimated tax payments (if necessary), your tax bill won't be until 4/15/22. Should be plenty of time to farm your promo money if you're that confident in it.

If you don't want a crazy tax bill, focus on selling long-term holdings (>1yr) since you'll have a lower tax rate there

These two statements alone show that you're not properly evaluating the deal.


And that's before even getting into the part where a regulated casino is going to give you a guaranteed 48% return on your entire net worth+.

There is no chance that a legit casino is going to let you 1.5x your net worth at their expense. As mentioned, it's a scam, or you're being mislead or missing some fine print. Revealing the name of the casino would, I imagine, be a wise decision.

Ok fine, the site is https://www.playup.com/

It's not an advertised bonus the VIP manager specifically called me when I signed up and I had to ask him about alternative signup bonuses. I think you guys underestimate how generous the Jersey casinos have been.

A google search shows plenty of articles saying they got their license from the state. Apparently the company is big in Autralia/NZ.

Partnered with Caesars. You're telling me this is a scam? https://www.onlinepokerreport.com/51...p-partnership/

I have a friend who was going to do the 5k caesars bet. Can you show me where you saw people not getting it paid out? I'm honestly shocked given how both Caesars and William Hill have paid me out over the years.

i bet with them occasionally in australia where they are based. they are a boutique book here in a landscape dominated by bigger players.

never had an issues getting paid or cashing out - but never have i ever had a juicy deposit bonus with them.

https://corporate.playup.com/team/

it's a legit company - at least in australia. website shows they have launched in us.

can't see them giving you a 50k deposit bonus on say $100k. if they do it will have a very short expiry.

I believe he said 30 days but I will be certain to get this in writing from him before I make moves. 1x and doesn't have to all be on one event. When I first asked him about the bonus he said "yeah I have a 50% high roller bonus if you deposit $30,000." Eventually I asked him if 30k was the max and he said there was no maximum and "if I wanted to deposit a million for it I can deposit a million." Agreed to let me make multiple deposits for it since im capped at 20,000 for every method. Even offered to drive me out to their physical location in Jersey (cant recall name RN) to deposit. It all seems pretty legit, IDK.

It feels like you've already decided what to do and this is basically a humblebrag. I look forward to hearing if it worked out for you.

If you have a decent size stock portfolio ($100k+) you should be able to find a bank willing to give you a loan for 60% of the portfolio value. Probably takes 1-2 weeks to get the loan underwritten and funded.

Mostly from Reddit

https://www.reddit.com/r/sportsbook/...aesars_az_yet/

https://www.reddit.com/r/sportsbook/...tent=post_body

https://www.reddit.com/r/sportsbook/...nt_worked_all/

Good chance these people eventually got paid, but their customer service is horrible and it sounds like a huge pain in the ass having to beg for them to honor their own promotion when it really should be done automatically upon losing the initial bet.

sound too good to be true so I wouldn't risk more than you could comfortably lose and not really care about.

Well I more was hoping to get advice on the best/smartest ways to leverage my assets for this and the ideal way to do it to avoid extra taxes and things like that. I really don't know that much about those subjects. I did not realize it would turn into people trying to warn me off it.

This is the correct answer.

We are not saying it’s a scam it’s just that being around how casinos operate they are not in the business of trying to attract one time customers who come play at a losing proposition for themselves. They do promotions like this occasionally and take the loss but you got to understand it’s with the expectation that you will continue to play and give action consistent with what you did during the signup bonus. When you don’t and immediately cash out they realize they messed up and try to find a way to recoup the money or get you to continue to play as much as they can within the law. It’s very easy to say after the fact that there was a misunderstanding with the promo dollars if the writing isn’t explicit and ironclad to at least delay payment of that and use it to negotiate after to get you to play more settle for less or just straight up not pay if the agreement isn’t strong as promotional money is a contractual dispute not a gaming violation.

The old me who used to play on off-shore casinos and has been robbed and screwed over many times fully agrees with you. The new me who has had nothing but positive experiences with every single jersey casino/sportsbook strongly feels this is safe. I do appreciate all of your cautions though!

I will look into that bank loan idea. Thanks guys!

Quick search:

DraftKings has reported earlier this year that a customer's lifetime value is $2,500, and that its average customer acquisition cost is $371.

VC catnip.

Do you think it's possible to take out the bank loan, then still do the robinhood withdrawal for more margin balance? Or would that piss off the lenders?

Including their signup bonus which is worth ~$1650 in equity they'd give out $2500 to any new player who knows what they're doing within a month or two. Seems like they're too generous for their own good. But there's a lot of competition out there in Jersey thankfully!

Like coupons, these contingent sign-up bonuses won't show up in their books as a CAC until they're redeemed.

Nothin more profitable than giving a free bag of smack to a reformed addict.

Been robbed and screwed over many times, but this time is different ( and too good to be true).



I do hope you get paid because it's the type of bink we all dream off.

Again I've only ever been screwed over by offshore shady sites.

Can you not accept there's a difference between unregulated and regulated casinos? If these ones try to screw me over I can take it to the DGE. I've played on about 30 of these for years and none of them have ever tried to screw me over before so why should I expect this one to now?