After winning the lottery, would you go for a straight-out check OR the lifetime income stream? While people will decide which is their BEST choice pretty quickly, do you have the right information to make that choice? Today we sit down with the CEO of Saber Pension and Actuarial Services, Brent Henningson to talk not just lottery, but maybe also pensions, annuities, and life settlements. Wait a minute? Is the annuity thing just a smokescreen so we'd pay attention to something that's important but maybe not that interesting? Maybe so, but however we get you to the table, these are decisions with thousands of dollars on the table and you can't afford to make the wrong choice.

Plus, is day trading easier than being a long term investor? We'll have some fun diving into why the Barstool Sports founder claims he is a better investor than Warren Buffet, and that day trading is "the easiest" game there is. David Portnoy is ALWAYS good for a quote or two. In the second half of our headlines segment, we'll share one list explaining why the RV life might not be the golden dream people are expecting. Even in retirement... informed planning is half the battle.

During our Haven Life Line will answer a call from military dentist Joe (not our Joe, of course), who will be separating from service next year to pursue specialty training. While he's going through classes his only planned income will come from the GI bill. Joe's two questions are, one: can he still contribute to his IRA during his education with no taxable income? If not, would working a few days a month make him eligible? Two: he is currently maxing his Roth TSP account. Should he drop his contribution amount to get more liquidity before leaving service?

As always, we're saving some time for Doug's trivia.

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What's Your Best Lottery Option? (plus your best pension option, annuity settlement, and more...) with Brent Henningson