Successfully Retired

Find The Needle or Buy The Haystack

Ever heard of looking for a needle in a haystack?It's what stock pickers do day in and day out, trying to find the best performing investment. 
 
But is it a good strategy?Tune in as Rick Luchini and I discuss a study that digs into the answer to this question, with shocking results, even for passive investors. 

Finding Purpose After The Paycheck

It's no surprise to most of us that work is a big part of our identity. Whether it's at a networking event, a little league game, or the neighborhood BBQ people's first question is often "What do you do for work?" Many of our clients are very successful as employees who've climbed the ladder. When they retire, it's up to them to reinvent some part of who they are.
 
Listen in as Rick and I share stories of clients who have successfully found their purpose once the paycheck ends, questions we ask our clients that help them reframe their thinking in the years leading up to it, and what can go wrong if you wait too long to find hobbies outside of work. 

Why Retirees Spend Less than They Could

One of the cruel ironies of money is that if you're a really good saver, spending down your investments is a tough mental switch. In today's episode Rick and I unpack some of our thoughts on why the middle-class millionaire retiree often times spend less than they could afford to - even if there are things they want to spend on! 
"Money is fuel, it only serves it's purpose when it's burnt." 
Listen in on real-life stories from retirees who made that transition successfully, and ones who struggled to stick the landing. 

Rental Property in Self Directed IRA - Is it Worth It?

It's the thing they're not making any more of - and no I don't mean bitcoin. Real estate.
 
Adding real estate to your investment portfolio is, for many people, a huge way to accelerate their wealth. I'm saying that and I don't even have a course I can sell you on how to 10x leverage yourself into an early AirBnb retirement.
 
But should you own real estate in a self-directed IRA?It's a less commonly known but completely legal way to buy a rental property. But buyer beware, while this may work in some instances, there are a bunch of pitfalls and ways that even savvy investors can turn their investment into a tax nightmare. Listen as Austin Preece of Preece Financial Services and I unpack the 3 big benefits of owning real estate outside of an IRA, and how owning it in a self-directed IRA can go wrong if not properly accounted for. 

Saving for Grandkids since OBBBB

In this episode Hamilton and Rick break down the best ways to save for a child’s future—comparing 529 plans, UTMA custodial accounts, and joint brokerage accounts. They cover the pros, cons, and recent 529 rule changes that add flexibility, including Roth IRA rollovers. The takeaway: don’t default to a 529—match the account type to your goals, control needs, and tax situation.

Do You Have a Tax Historian or a Tax Planner?

In this episode, Rick and I break down the critical difference between a tax preparer who records the past and a tax planner who shapes your future. Learn how proactive planning can eliminate tax surprises, keep more money in your pocket over your lifetime, and align your tax strategy with what matters most to you.

The Retirement Tax Myth: Why You Might Pay More Than You Think

Many people plan for retirement under the assumption that their tax bill will drop once they stop working — but what if that’s not true? In this episode, Rick Luchini and I break down why taxes could actually be higher in retirement, from shifting income sources to changing tax laws. You’ll learn how using "rules of thumb" instead of personalized tax planning can lead to surprise tax bills throughout retirement. We’ll also share strategies to prepare now, so you’re not caught off guard later.

Will a fed rate cut lead to lower mortgages? Maybe not.

With everyone talking about a fed rate cut in September home buyers and mortgage holders are hoping they can see more favorable interest rates on 30 year mortgages soon. But will a lower fed funds rate actually lead to lower mortgage rates? Maybe not.In this episode Austin Preece and I tackle some common misconceptions around interest rates. We get into the 2 jobs the Fed has, why mortgages are more closely related to the 10 year treasury than the Fed Funds rate (in non-investmenty speak), why so many millennial financial advisors hate bonds (maybe hate is a strong word), and how tactical bond investors might change their strategy going into the end of 2025.