Looking for Setups in the Setbacks

Time travel is a powerful way to reframe the present. The here and now will always bring its unique challenges and setbacks, but what will this moment mean to you down the road, looking back?

If you’re prone to stay mired in the moment, here’s a game of “I spy” for you: where are the setups among all these setbacks?

You’ve heard it from us before. There’s day-night, day-night. There’s up-down, up-down. Well here’s one for any challenging time: setback and setup.

Challenging times bring tradeoffs, big and small. In some moments, there is less time for work… but more time with the kids. Or less time with the gym buddies… but more time out in the sunshine. Tradeoffs.

In terms of business, our classic principles still apply during challenging times. We seek bargains. Economic activity is always shifting: some areas will slam on the brakes as demand falls off; some areas will be buzzing in a scramble to keep up with demand.

Just like the setbacks in our individual lives, the business setbacks exist alongside potential setups. Part of our job is to take a good look around to try to spot them. No guarantees, but we’re always wondering what future growth is being watered by the current storm.

We don’t ignore a storm. This approach, however, helps remind us of the bigger picture. It’s a more complete way to tell the story of a setback.

Clients, if you would like to talk about this or anything else, please email us or call.


Want content like this in your inbox each week? Leave your email here.

Play the audio version of this post below:

This text can be found at ⁠https://www.228Main.com/⁠.

When Buying “The Stock Market” May Not Be Optimal 

When people talk about “the stock market,” they might actually be thinking of the Dow Jones Industrial Average, or the S&P 500 Index. These lists are what they sound like: averages and indexes of exchange-traded securities. 

And one popular school of investing calls for buying index “funds,” collections that offer a slice of what’s happening on one of those lists. The goal is to capture the list’s average return. It’s simple, easy, and relatively inexpensive to seek to replicate those market averages. 

But there’s a tradeoff. There have been extended periods when those averages basically went nowhere for many years at a time. The “average” approach means you are by definition going with the crowd. But crowds can become herds, which can turn into stampedes. 

This is what happened with the raging Nifty Fifty and again in the Tech Wreck. 

Back in 1973, the “Nifty Fifty” stocks were all the rage. Many scrambled to buy and hold these dominating stocks, names like IBM, Xerox, or Coca Cola. One might say there was a stampede into the favored names. Valuations got stretched, the S&P 500 peaked—and proceeded to fall about 50%.  

It took until 1982 to regain that 1973 peak, before moving any higher: a decade with essentially no progress. 

It happened again from March 2000 to 2013, a time that got the nickname the “Lost Decade.” This time, the mania was internet stocks. Technology and communications companies dominated the S&P 500, and investors got excited. Again, more people stampeded in, valuations got stretched, the S&P 500 peaked—and proceeded to fall about 50%. Not until 2013 did the index begin to make and hold new, higher ground. 

So what was problematic about those peaks? The largest companies became a much larger fraction of the total value of the S&P 500. The top companies in 1973 and 2000 had become worth many times the bottom companies combined.  

Staying with the crowd—buying indexes and aiming to capture averages—is not the only way to invest. In those episodes from history, some other sectors fared better than the fallen favorites and broad U.S. market averages. There were those smaller companies, value-style investments, and overseas markets that generally went up during the Lost Decade. 

At 228 Main, our core investing principles include “avoid the stampede” and “seek the best bargains.” As such, while the largest companies in the S&P 500 are becoming increasingly concentrated at the top—reminiscent of 1973 and 2000—valuations may be getting stretched once again. We are seeking to have more and more of our portfolios invested other places. (Research is a core activity here, a daily discipline, and we invest a lot of time and energy into it.) 

That is to say, we’re seeking opportunities outside the averages. We’ve got our eye on value-style companies—those that seem to provide a lot of current profits, or cash flow, or dividends relative to each dollar invested. We’re seeking companies operating in faster-growing economies, the ones that provide food, shelter, transportation, communications, or energy (and are trading at more attractive prices). We want to know what’s happening with smaller companies, the opportunities that don’t fit the profile of those mega-sized names that dominate the market averages today. 

There are tradeoffs involved with either approach.  

  • When we follow the averages, we risk following the crowd straight into a stampede. 
  • When we buy the bargains, our particular favorites may get cheaper while the darlings of the market are still climbing higher. Our portfolio performance could generally lag a red-hot market.  

To be clear, we are still invested in those large U.S. growth companies we’ve mentioned. But, clients, we’re more diversified now than we’ve been at any time since the early 2000s. Even though we may be on the right track for long-term investors, it can be lonely to be contrarian. So it’s times like these that it helps to check in, take the long view, and make sure the methods suit the goals.  

And for us, it’s the pursuit of capturing the potential growth, for the long run. No guarantees, but that’s what we’re working toward. 

Clients, please call or email us if you would like to talk about this or anything else. 


Content in this material is for general information only and not intended to provide specific advice or recommendations for any individual. All performance referenced is historical and is no guarantee of future results. All indices are unmanaged and may not be invested into directly. All investing involves risk including loss of principal. No strategy assures success or protects against loss. 


Want content like this in your inbox each week? Leave your email here.

Play the audio version of this post below:

When Buying “The Stock Market” May Not Be Optimal 228Main.com Presents: The Best of Leibman Financial Services

This text can be found at https://www.228Main.com/.

Catch-Up > Ketchup

graphic shows a piggy bank looking on curiously at a bottle of ketchup

These two terms may essentially be homonyms, but one is so much greater than the other. Kiddos sometimes choose huge portions of the condiment ketchup. But beyond a sugar-fueled addiction for dipping our fries in that one is a great opportunity to “catch up” on our IRA contributions. 

In the world of IRAs—Individual Retirement Accounts—we consider the beginning of January through tax filing day “catch-up season.” Whether Roth or traditional, if we are eligible to make contributions, then we can catch up on last year’s contributions even though the last calendar year is over. 

Those just learning about the power of Roth IRAs can use this season to make two years’ worth of contributions at once. Even with the federally-mandated limits, you can contribute thousands of dollars in standard contributions. And for people who turned 50 by year-end, there is an extra “catch-up” contribution option. 

Consider even just the standard contribution limits. Imagine if you had $15,000 in a regular account (in which you pay tax on earnings) and were eligible to contribute to a Roth IRA for both this year and next year. If you won’t be spending that money in the next few years, the question comes down to whether you would like to never pay tax on earnings on that money–ever again, for the rest of your life. 

If that value were to double over the years and double again, as sometimes happens with long-term investments, there might be $60,000 available later with zero tax. After five years your contributions can be withdrawn without tax. At the later of five years or age 59½, the earnings may be withdrawn without tax too. And if you didn’t withdraw it, your beneficiaries would receive it, free of income tax. 

No guarantees, of course: the markets go up and down. 

There is a maximum earnings limit on Roth contribution eligibility, and there is a whole world of other lifetime tax reduction strategies related to Roth conversions. We’d be happy to visit with you about your eligibility. Simply email us or call if you have an interest in learning more. 

For now, happy catch-up season, one and all! 


A Roth IRA offers tax deferral on any earnings in the account. Qualified withdrawals of earnings from the account are tax-free. Withdrawals of earnings prior to age 59½ or prior to the account being opened for 5 years, whichever is later, may result in a 10% IRS penalty tax. Limitations and restrictions may apply. 

Investing involves risk including the potential loss of principal. No investment strategy can guarantee a profit or protect against loss. 

This information is not intended to be a substitute for specific individualized tax or legal advice. Neither LPL Financial, nor its registered representatives, offer tax or legal advice. We recommend you discuss your specific situation with a qualified tax or legal advisor.


Want content like this in your inbox each week? Leave your email here.

Play the audio version of this post below:

Money Grows (But Not on Trees) 

photo shows a green tree along a country lane, surrounded by green fields

Over the past few years, more of us have found the joy of raising backyard chickens or container gardens or fruit trees. It’s an opportunity to see the fruits of our labor—literally!—grow.  

It may take a few years for a new apple tree to produce. But with care and attention, that same tree may over time provide bushels of fruit for you, your family, or your community.  

Growing your wealth isn’t that much different.  

For example, if you put $10,000 into a savings vehicle that paid 2% annual interest, how long would it take you to double your money? The intuitive answer would be 50 years: 50 x 2% equals 100% return. 

But due to the effects of compound interest, you’d actually get there in 36 years—not 50.  

You don’t just get interest on the money you originally put in: you’d be getting interest on the interest you’ve already earned, too. 

Doubling your money in 36 years is not terribly impressive. But then, 2% is not a terribly impressive rate of return. At 4%, as you might expect, you can double in half the time: a mere 18 years. So in 36 years, you’ll have doubled twice, quadrupling your original money. In 54 years, it would be eight times what it originally was!  

That may sound like a long time, but if a person started saving in their 20s, they could reasonably expect to have 50+ years for their earliest savings to compound. 

And that’s at a relatively conservative 4% annual return. As your rate of return increases, your compounded returns increase exponentially. At 5%, your money would increase tenfold in 50 years. At 6.5%, your money would increase twentyfold in the same time: a mere 1.5% increase in returns doubles the money over 50 years!  

All of this to say, it doesn’t take very many doublings to turn modest savings into a sizeable pile of money. 

Of course, sometimes this is easier said than done. Just as some growing seasons are rougher than others, returns are never guaranteed, and pursuing higher returns generally means accepting more volatility and risk. 

Potential growth takes preparation, patience, and a little guidance along the way. Even modest investments can multiply. We’re here to keep an eye on the math together. Don’t worry: no quizzes. 

If you’d like help planning, planting, or tending your financial orchard, we’re here to work alongside you as it tries to grow. 


The opinions voiced in this material are for general information only and are not intended to provide specific advice or recommendations for any individual. Investing involves risk including loss of principal. 

This is a hypothetical example and is not representative of any specific situation. Your results will vary. The hypothetical rates of return used do not reflect the deduction of fees and charges inherent to investing. 


Want content like this in your inbox each week? Leave your email here.

Play the audio version of this post below:

This text is available at https://www.228Main.com/.

Embracing the Loops, Swoops, and Squiggles

Sometimes life’s big milestones arrive in a neat, straight line. And sometimes that’s just not what happens—or what we want to happen. How do we plan for a swoopy life?


Want content like this in your inbox each week? Leave your email here.

Resolved: I Will Do Away with Resolutions

Spruce branches surrounded by a clothes clip holding a note with New year, New chances, New goals, New Start, New results all crossed out with red marker

by Mark Leibman, President

With serious planning and determination, many of us are gearing up for the next round of New Year’s resolutions. The change in the year will be the time we finally lose weight, or drink less, or exercise more, or wake up at 4 a.m. like those social media productivity thought-leading rockstars do! 

As for me, I will not have a New Year’s resolution. I won’t be hustling to be the oldest participant in the hardest 5k in the state in 2026. I will not be striving to achieve or maintain a specific weight. I will not be avoiding or including certain foods in my diet. No resolutions. Not one. 

Many of you have heard me say that I’m planning to work to age 92. Will any New Year’s resolution make that happen? There’s nothing magical about December 31 (except perhaps some fireworks at midnight!). I don’t measure my health by a calendar.  

Instead, I measure my efforts every single day.  

When you really think about it, doesn’t wealth work the same way? Even though we measure markets on an annual basis, that’s really just a long-held standard for consistency. You may have heard that in 2025, the stock market (as measured by the S&P 500) was up 12% for the year, January to December. But we have the tools to calculate the return for whatever 365 consecutive days you’re interested in. We can look at the results birthday to birthday, or any other range we’d like. 

The process of becoming financially independent—of gaining the option to live on your wealth instead of your labor—uses essentially the same process as my health goals. Steady decisions, over time. 

And we’re here to help anybody navigate the process. We try to offer guidance in your journey through the economic ups and downs, the noise of market pundits both on business channels and at the café. To focus on your financial health overall, instead of some calendar-year resolution. 

Just like my health goals don’t change when I buy a new calendar, my wealth goals don’t need to either. 

Clients, don’t think we are against all New Year’s resolutions. There’s actually one I highly recommend: in 2026, help someone learn what’s going on here at 228 Main in beautiful downtown Louisville. I know I’ll try to stick to that one too. 

Thank you all, for everything. 


Content in this material is for general information only and not intended to provide specific advice or recommendations for any individual. All performance referenced is historical and is no guarantee of future results. All indices are unmanaged and may not be invested into directly.

All investing involves risk including loss of principal. No strategy assures success or protects against loss.


Want content like this in your inbox each week? Leave your email here.

Play the audio version of this post below:

Resolved: I Will Do Away with Resolutions

Spruce branches surrounded by a clothes clip holding a note with New year, New chances, New goals, New Start, New results all crossed out with red marker

by Mark Leibman, President

With serious planning and determination, many of us are gearing up for the next round of New Year’s resolutions. The change in the year will be the time we finally lose weight, or drink less, or exercise more, or wake up at 4 a.m. like those social media productivity thought-leading rockstars do! 

As for me, I will not have a New Year’s resolution. I won’t be hustling to be the oldest participant in the hardest 5k in the state in 2026. I will not be striving to achieve or maintain a specific weight. I will not be avoiding or including certain foods in my diet. No resolutions. Not one. 

Many of you have heard me say that I’m planning to work to age 92. Will any New Year’s resolution make that happen? There’s nothing magical about December 31 (except perhaps some fireworks at midnight!). I don’t measure my health by a calendar.  

Instead, I measure my efforts every single day.  

When you really think about it, doesn’t wealth work the same way? Even though we measure markets on an annual basis, that’s really just a long-held standard for consistency. You may have heard that in 2025, the stock market (as measured by the S&P 500) was up 12% for the year, January to December. But we have the tools to calculate the return for whatever 365 consecutive days you’re interested in. We can look at the results birthday to birthday, or any other range we’d like. 

The process of becoming financially independent—of gaining the option to live on your wealth instead of your labor—uses essentially the same process as my health goals. Steady decisions, over time. 

And we’re here to help anybody navigate the process. We try to offer guidance in your journey through the economic ups and downs, the noise of market pundits both on business channels and at the café. To focus on your financial health overall, instead of some calendar-year resolution. 

Just like my health goals don’t change when I buy a new calendar, my wealth goals don’t need to either. 

Clients, don’t think we are against all New Year’s resolutions. There’s actually one I highly recommend: in 2026, help someone learn what’s going on here at 228 Main in beautiful downtown Louisville. I know I’ll try to stick to that one too. 

Thank you all, for everything. 


Content in this material is for general information only and not intended to provide specific advice or recommendations for any individual. All performance referenced is historical and is no guarantee of future results. All indices are unmanaged and may not be invested into directly.

All investing involves risk including loss of principal. No strategy assures success or protects against loss.


Want content like this in your inbox each week? Leave your email here.

Play the audio version of this post below:

How Many Hats at a Time?

The current image has no alternative text. The file name is: photo-workspace-1.png

Every once in a while, the schedule gets really and truly full. We might have places to be throughout the day, for many days in a row. Weeks might go on like this, in an exciting blur.

It’s not a bad problem to have, but sometimes, it can feel like we’re being pulled in more than one direction.

Some of you may experience this sensation too, as you also wear multiple hats in life. You may have commitments as a parent, an employee or an owner, a teacher, a partner, a community member, and more.

Here’s an idea that might provide some relief: we may have many hats, but we only wear one hat at a time. It’s okay to allow ourselves to focus on one at a time, even if we must switch hats often.

The same general principle is true about our financial goals: it may seem prudent to save for retirement, and a house, and a child’s education, and all the other things one may want in a lifetime… but the secret is that you don’t pay for these things on the same day, or week, or month, probably.

Having many hats doesn’t mean we can’t focus—and strategize. Time is finite, of course. But we take things one hat at a time.


Want content like this in your inbox each week? Leave your email here.

Play the audio version of this post below:

Friendly Faces and Important Roles

Clients, it’s Caitie here. I’m so thrilled to introduce you to our newest teammate, Allison Bauers! In a small business, we tend to wear many hats, so this week, we’re chatting about how our roles and duties will change in the coming months.


Want content like this in your inbox each week? Leave your email here.

Avoid the Stampede: It’s a Classic for a Reason

It’s one of our core principles for a reason: “avoid the stampede.” We live in uncertain times, and it is understandable to get spooked by the day’s headlines. But we do not believe that safety is found following the herd.

Omaha is famous for its stockyards and slaughterhouses; we know that when the cattle are all getting steered together, it rarely ends well for the cattle.

Consider some lessons from history in this classic message.


Want content like this in your inbox each week? Leave your email here.