investment strategy

Choose Your Ingredients 

by Mark Leibman, Advisor

I learned how to make soup back in the last chapter. Now a variety of soups are a staple of my diet. 

Crafting a new soup recipe recently, I started with a chicken, six herbs and spices, and seven kinds of vegetables. I used some olive oil and a splash of red wine vinegar. It may be served with a mix of seven kinds of beans, and rice, of course (you know how I feel about rice and beans!). 

It came out really good!—according to a biased observer that I recently married.  

Contemplating the choices made in the creation of the soup, I thought about how we build portfolios here at 228 Main.  

From many alternatives, we select what we want to own and determine the proportions of each. Another school of thought holds that portfolios should consist of some of everything—500 stocks go into the S&P 500 index, for example, so portfolios get to hold a little of each. 

That led me to wonder, What would Index Soup look like? 

  • 150 herbs and spices? 
  • 50 kinds of vegetables? 
  • Beef, pork, chicken, fish, and eight more kinds of animal protein? 

And it might even be served with 25 kinds of beans, and 10 varieties of rice! 

That would have to taste like a little bit of everything, and not much of anything, wouldn’t it? 

Just as different recipes can reflect a wide variety of tastes and textures and smells, and we humans have an appetite for different things at different times, our portfolios evolve and change as conditions unfold. 

By looking for the best bargains, by avoiding stampedes in the market, by planning to own the orchard for the fruit crop (thinking long-term), our collection of opportunities has diverged from the most popular kind of Index Soup, the S&P 500.  

Creating our own recipe helps avoid another possible pitfall of Index Soup—not that it can get too bland in its attempt to average everything, but that it can get too heavy-handed in spicy times. 

Recently, slightly more than half of our long-term portfolios are invested in small- and mid-size companies. We’re diversified around the world, although about two-thirds of value is still invested in the U.S. While AI-related stocks have captured the public imagination, we’re focused a little more on value-style stocks than the mega-size growth companies, which we believe may be over-valued at present. No guarantees, but we’re trying to be intentional with our flavors. 

Meanwhile, Index Soup focuses on large U.S. companies, with an emphasis on growth. Technology is nearly 37% of the mix in that soup, and the top seven holdings are mega-size tech companies.  

We know that the flavor can get “too strong” at times: back in the year 2000, the S&P 500 index, and technology stocks generally, left a bad taste in the mouths of many investors the last time valuations approached extreme levels.  

We can’t know the future, but we are hopeful our recipe is going to “taste” a lot better in the months and years ahead. No guarantees—past performance is not an indicator of future results. 

But we don’t have to be the best chefs in the world. We’re just trying to find a blend that works for us. 

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Investing involves risk including the loss of principal. There is no assurance that the views or strategies discussed are suitable for all investors or will yield positive outcomes. 

The opinions voiced in this material are for general information only and are not intended to provide specific advice or recommendations for any individual. There is no guarantee that a diversified portfolio will enhance overall returns or outperform a non-diversified portfolio. Diversification does not protect against market risk. 

The S&P 500 is an unmanaged index which cannot be invested into directly. Past performance is no guarantee of future results.  


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The text of this episode is available at ⁠⁠www.228Main.com⁠⁠.

Going public: Billy’s thoughts on IPOs

Initial Public Offerings (IPOs) have been in the headlines lately. More than a dozen companies offered IPOs in June 2026. So we’re encouraging you to take five minutes to hear Billy talk about our take on IPOs.


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Distracted by Shiny Objects?

“There’s gold in them thar hills!” Gold and the rush to grab it have fascinated Americans for so long.  

We’ve been hearing again about the allure of it and other precious metals as investments. Hear from Greg on whether the enchantment makes sense for us.


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What We Do—But Mostly What We Don’t

Organizations sometimes use “mission statements” to capture their core focus or values. In a sentence, why does this company exist? What is its main purpose? What’s the goal?

It’s a useful exercise. If we had to spit it out, what would we say we do? We invest.

There are a lot of ways to flesh out and explain this mission (and we do that, often, in our communications!). But we also consider ourselves contrarians. So it makes sense that we also like to explain our work in terms of what we don’t do.

We invest… but not with guardrails. No training wheels, no buffers, no timing schemes. We don’t give guarantees, and we will not offer a false hope of market returns without market volatility.

Why don’t we like that stuff? All of those things cost money or opportunity—or both—and thereby limit our future wealth.

So you won’t see us whipping out any literature about risk that confuses it with volatility. You won’t see pie charts that arbitrarily slice up a portfolio. We won’t pretend to know better than you about your goals or how you live your life.

We seek to invest for the long term when the cost of owning a percentage is lower than the value of the ownership opportunity, in our studied opinion—even as we know that the market price will fluctuate, even as we know we will not always be right.

But a smoother ride to a poorer future? No thanks.

Clients, want to talk in more detail? Call or email, anytime.


Content in this material is for general information only and not intended to provide specific advice or recommendations for any individual. Investing involves risk including loss of principal. No strategy assures success or protects against loss.


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Getting Down to Brass “Tax”

photo shows a light letter box with the word "TAXES" sitting on top of various cash bills

While paying taxes is generally a good sign that you are making money, it seems most people want to avoid paying more tax than they need to. It’s a common enough question we field, and one worth considering.

How do we handle the tax impacts of our choices?

For smaller investors with tax-deferred vehicles like IRAs or 401(k) plans, tax considerations are simpler. Only deposits and withdrawals have any tax implications (and for Roth IRAs, rarely even then.)

Things get more complicated for investors with substantial balances outside of retirement accounts: most trading activity has tax impacts. You pay taxes on interest and dividend payments; you also become subject to capital gains tax when selling investments.

The principle of capital gains is straightforward enough. For instance, if you buy stock for $100 and later sell it for $100, you made no money and owe no tax. If you were to sell it for $110, you would have to pay some percentage of the $10 profit in tax (but not the rest of the $100: that was money you had in the first place.) And if you sold it at $90, you would have a loss of $10 that you could use to offset taxable gains elsewhere.

The important thing here is that the IRS generally only cares about the value of investments when they are bought or sold. If your $100 stock position balloons up to $1,000 one year and then collapses back down to $100 the next, the IRS has no interest in the round trip. They only see the difference from your original purchase, regardless of how high or low the price got in the meantime.

It is easy to despair when an investment is underperforming, but according to the IRS, those losses do not exist until you decide to sell. And if a high-flying investment should pull back from its highs, the IRS would give you a very funny look if you tried to claim it as a loss.

So if the IRS does not care about your gains or losses “on paper,” why should you? A drop is not a loss, and value at inception is a great anchor to come back to when you need a jolt of perspective.

And if after all this you find yourself with more resources than you would need in your lifetime, there are estate planning opportunities to consider. If you are sitting on long-term investment gains that you do not think you will be spending, there is little reason for you to sell those holdings and pay taxes on your gains yourself.

If those assets are passed down to your heirs, however, they would generally only need to worry about gains made after they inherited them, so whatever gains you accumulated during your lifetime can pass to them tax-free.

Lots to think about! It’s an important topic for many investors. Clients, when you need to talk about your tax considerations, please reach out.


This information is not intended to be a substitute for specific individualized tax advice. We suggest that you discuss your specific tax issues with a qualified tax advisor.


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Play the audio version of this post below:

What the IRS Knows: Getting Down to Brass "Tax" 228Main.com Presents: The Best of Leibman Financial Services

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

Selling Out Is a One-Way Ticket

As we know, the markets go up and down. It’s just part of the deal! But sometimes the peaks and drops can get a little intense, so it’s worth revisiting this reality once in a while. 

The most mindful long-term investors are usually less alarmed by the bumps along the way. They know what they’ve got is basically a lifetime pass on a rollercoaster. But it’s the ride to greater potential returns, so they can keep the thrills in perspective. 

What would the alternative be, in our rollercoaster example? If you get spooked on a big drop, there’s no abandoning your seat. “Please keep your hands, arms, feet, and legs inside the vehicle while on this ride,” the announcement cautions. 

It’s best to stay in your seat, your best chance to get to the end of the ride in one piece. 

As long-term investors, we know that we can afford to let each cycle just run its course. Jumping off the ride partway through sets us up for more trouble and more work than it would ever be worth: how would we know when it’s best to jump back on? How do we know that we’ll be able to jump safely? 

We hope this is context enough to allow us to be blunt with you: long-term investing is a ticket for the whole ride, whatever that may mean. 

Selling out? Selling out is a one-way ticket out of our shop. 

Your resources are your business. Where you park your wealth is your decision, completely, and each one of us needs to do what is best for them. 

But we choose to keep at it for those who are thinking about the long haul. We believe it’s the most effective approach to a lifetime of financial wellbeing—and whatever legacy might stretch beyond your lifetime! 

Clients, we strive to communicate our values and intentions clearly. Do you need to clarify anything with us? Call or write, anytime. 


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

Humbug-Free Financial Planning

Say, are you catching any holiday specials this season? There are even more movies this year spinning their own version of the Dickens classic A Christmas Carol. Hard to believe the story is more than 170 years old, but many of its lessons have stood the test of time. 

Life is often about learning and changing, isn’t it? Our work with you has some similarities to this classic tale. (But in our version, I suppose, no one is the Scrooge. We’re all already trying to grow and do our best!) 

Our first meeting, we meet your Ghost of Financial Planning Past. The past is formative—and informative. What brought you into our shop? How did you get here? What are the relevant parts of your past that have shaped you? 

We get a collaborative sense of what your story has been, up to this point. The Ghost of Financial Planning Past is someone you’ll have to introduce us to. It’s just where our story starts! 

As our work with you goes along, we stay in touch with the Ghost of Financial Planning Present. This is the spirit of action, the one who is most aware of the pertinent things going on in your life right now. They help us write the story anew, each and every day. 

The Ghost of Planning Present is the one managing those big life shifts: job change, big move, or early retirement on your mind? The spirit is there, helping draw your attention to what matters most to you. 

We are a key character in this part of the story, too. If you are living on your capital, for instance, we help arrange the ongoing details of how you finance the present. Or when your situation changes and adjustments need to be made in your plans and planning, then you can get us involved. 

Finally, we all must be ready to face the Ghost of Financial Planning Future. This specter is always a little blurry at the edges: nobody can know them that well, after all. But this is the spirit that helps us imagine what awaits us. We must live with the consequences of our choices, so how might our hopes, dreams, and goals shake out? 

The future is where your plans meet reality. When we are able to sketch out our aims, we have a better chance to befriend the Ghost of Planning Future. We can’t fully script this part of the story, but where there’s some arithmetic to do or strategy to implement, we’ll be there to help shape the story. 

It seems we are never done visiting with any of the spirits. The longer we know you and grow together, the past expands behind us. The present is always unfolding, day by day. The future is ever-changing too, as tomorrow becomes today. The future keeps skipping ahead just out of reach, the past grows, and all while we live in the present. 

The present is where we turn the future into the past. And we love striving to help you make the most of it! 

Clients, if you would like to talk about any of the parts of your life, please haunt us at your convenience. It’s our pleasure to be part of the story.


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Play the audio version of this post below:

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

What the IRS Knows: Getting Down to Brass “Tax”

photo shows a light letter box with the word "TAXES" sitting on top of various cash bills

While paying taxes is generally a good sign that you are making money, it seems most people want to avoid paying more tax than they need to. It’s a common enough question we field, and one worth considering.

How do we handle the tax impacts of our choices?

For smaller investors with tax-deferred vehicles like IRAs or 401(k) plans, tax considerations are simpler. Only deposits and withdrawals have any tax implications (and for Roth IRAs, rarely even then.)

Things get more complicated for investors with substantial balances outside of retirement accounts: most trading activity has tax impacts. You pay taxes on interest and dividend payments; you also become subject to capital gains tax when selling investments.

The principle of capital gains is straightforward enough. For instance, if you buy stock for $100 and later sell it for $100, you made no money and owe no tax. If you were to sell it for $110, you would have to pay some percentage of the $10 profit in tax (but not the rest of the $100: that was money you had in the first place.) And if you sold it at $90, you would have a loss of $10 that you could use to offset taxable gains elsewhere.

The important thing here is that the IRS generally only cares about the value of investments when they are bought or sold. If your $100 stock position balloons up to $1,000 one year and then collapses back down to $100 the next, the IRS has no interest in the round trip. They only see the difference from your original purchase, regardless of how high or low the price got in the meantime.

It is easy to despair when an investment is underperforming, but according to the IRS, those losses do not exist until you decide to sell. And if a high-flying investment should pull back from its highs, the IRS would give you a very funny look if you tried to claim it as a loss.

So if the IRS does not care about your gains or losses “on paper,” why should you? A drop is not a loss, and value at inception is a great anchor to come back to when you need a jolt of perspective.

And if after all this you find yourself with more resources than you would need in your lifetime, there are estate planning opportunities to consider. If you are sitting on long-term investment gains that you do not think you will be spending, there is little reason for you to sell those holdings and pay taxes on your gains yourself.

If those assets are passed down to your heirs, however, they would generally only need to worry about gains made after they inherited them, so whatever gains you accumulated during your lifetime can pass to them tax-free.

Lots to think about! It’s an important topic for many investors. Clients, when you need to talk about your tax considerations, please reach out.


This information is not intended to be a substitute for specific individualized tax advice. We suggest that you discuss your specific tax issues with a qualified tax advisor.


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

Play the audio version of this post below:

What the IRS Knows: Getting Down to Brass "Tax" 228Main.com Presents: The Best of Leibman Financial Services

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

A 100% Chance of Weather

photo shows a misty landscape, partly in light rain, partly in blue sky

Understanding the risks involved is an important part of decision-making. Most would agree, I think, because how can we make informed decisions without weighing the consequences?

What makes it tough, however, is that a lot of financial planning literature uses the word “risk” when they’re actually talking about volatility. It’s about as helpful as the local news personality letting us know that weather is ahead: “There’s a risk of weather today! Heads up, everyone.”

How would that possibly help us make informed decisions?

Instead of railing against the presence of weather—or gravity, or any other to-be-expected force!—we like to spend our energy paying attention to risks that can actually affect our long-term goals.

Recall that in our shop, risk assessment takes place with a long time horizon in mind. We believe that you should have the money you’ll require for the next 3–5 years invested outside of the market. (Short-term volatility is a risk during the short term.) If you’re parking your money with us for a longer time horizon (3+ years), here are some risks you can expect we will factor into our strategy:

  • Concentration risk. Too many eggs in one basket could spell trouble if the basket upsets.
  • Inflation risk. Over time, what’s the likelihood this investment can outpace inflation? Put another way, what’s the risk of losing purchasing power over time?
  • Investment risk. What’s the likelihood that this investment will substantially change for the worse as time goes on or that the players could go out of business?

How much risk a portfolio might endure depends on a number of factors—your investing time horizon being just about the biggest one. There are other types of course, but these are some of the main examples of the risks we’re attuned to.

Volatility isn’t one of them. We don’t “mitigate” weather by hiding in a burrow forever; we don’t react to short-term swings by pulling out. As if we could spell it out any plainer, here’s our periodic reminder: we live with volatility in the pursuit of long-term gains.

Clients, when you want to talk risks, time horizons, and goals, email or call.


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Missing the Target


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