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Jake Dozer
Jake Doser, CFP®, CPWA® — Partner and Financial Advisor at Rosewood Wealth Management in Durham, NC, and frequent guest on the firm's "Mr. Stillman's Opus" podcast.
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Oct 23, 2026
How Do You Plan for Long-Term Care?
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9:28Jake DozerGUEST
Another option that I'm thinking of is and this is a really specific niche option but you know we're always exploring these options and the scope of this visit is a video is not for you to oh yeah let me get a checklist a comprehensive checklist of this is exact policy.
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9:43Jake DozerGUEST
It's more of to give you the seeds and food for thought for you to be able to start thinking through the options that make sense for you.
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9:50Jake DozerGUEST
But another one is where you add this sort of long-term death component to another insurance product, such as an annuity.
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9:57Jake DozerGUEST
And annuities can look in a lot of different forms or fashion where you have this lump sum of cash outside of retirement accounts or that you've pulled from retirement accounts.
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13:47Ben GeorgeHOST
Is there anything else besides insurance that you can do to help protect yourself? If you don't want to go down that path, if you're just looking for other options in terms of making sure that you are prepared for that expense should it come, is there anything else that you guys typically work with your clients to do?
What To Do NOW To Reduce Next Year's Tax Bill
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0:47Jake DozerGUEST
A donor advised fund is something that's a really minimally used but often overlooked tool.
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0:55Jake DozerGUEST
You're approaching the end of the year, kind of similar to the time that we're recording this video right now, and you have identified that you are going to come into a larger tax liability than you'd like.
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1:07Jake DozerGUEST
Maybe you've had an unexpected windfall this year of selling a home or a business practice.
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1:12Jake DozerGUEST
Maybe you just got a quarter end bonus and you're just thinking about, whoa, my income is at a place where I'm blessed to be in a position where I'd like to lower those taxes by putting some money away, doing something creative.
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4:13Ben GeorgeHOST
The SEP IRA, how many people are aware of that? And why should this be something that's on your list?
What Scares Investors More Than Halloween?
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1:48Jake DozerGUEST
And Some folks would not say I'm afraid of running out of money, but a lot of times their behaviors exhibit that fear.
5 MINS LATER
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7:29Ben GeorgeHOST
So when you're working with someone that's really worried about is how can I afford health care down the road? What am I going to do to pay for health care down the road? How do you build that into a plan?
These 5 Questions Reveal A Lot About Your Financial Plan
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0:54Jake DozerGUEST
Well, look, if it's 1045 on a Tuesday night and you want to talk about that, too, by all means, I'm sleeping at 10.
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1:03Jake DozerGUEST
But I love this question because the goal of these questions is to peel back the onion and recognize, first and foremost, retirement is not just I'm done working.
6 MINS LATER
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6:57Ben GeorgeHOST
Why are we asking this question, Jake? So knowing what you know now, what would you have done differently financially? So what are we trying to figure out with that question?
Are Roth Conversions Right for Me?
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4:50speaker_3ADVERTISER
flexibility do you want to prepare for?
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4:53Jake DozerGUEST
So you have to think about not only, you know, this element of does this save me taxes? That's a good question to ask, which is over my lifetime, will doing a Roth conversion save me taxes? Will this Roth conversion save my heirs taxes? But you also have to think about the fact that Roth conversions provide flexibility and kind of complete defense against additional taxes.
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5:17Jake DozerGUEST
What do I mean by that? Well, let's say that in 10 years from now, taxes are higher than they are right now.
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5:22Jake DozerGUEST
which if I were a betting man, I certainly wouldn't bet that over time taxes will be lower than they are.
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5:28Jake DozerGUEST
Just not talking about your income or lifestyle, just let through legislative changes.
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5:31Jake DozerGUEST
I mean, our country is in billions and billions of dollars in debt to the point where the debt exceeds our GDP.
When is the Best Time to Start Social Security?
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0:56Jake DozerGUEST
If you can guarantee me that you're going to live a really long time and your only goal is to get as much from Social Security as possible, then I do have a magic solution.