In 1999, a book changed the direction of my life.

At the time, I had recently dropped out of law school and was trying to figure out what was next. I was in that phase of life where you have plenty of energy and curiosity, very little skill, and a strong desire to do something meaningful that helps other people.

Around that time, I met Larry Swedroe.

Larry had written a book called The Only Guide to a Winning Investment Strategy You’ll Ever Need. I still remember sitting down with it and realizing that the first 100- pages quietly reshaped how I thought, not just about money and investing, but about what I wanted to do in my professional life. The approach felt more like a calling than a job.

Until then, I thought investing was about forecasts, predictions, and confident opinions about the future. Larry’s work introduced me to something very different. It was grounded in data and evidence. It showed that humility, discipline, and a long-term perspective were far more powerful than trying to outguess markets and pick winners.

It felt logical, rational, and deceptively simple to me. It smelled like the truth. And I loved it.

That realization set me on a course that eventually led to the creation of Hill Investment Group.

Years later, when we started the firm, I ran into an unexpected problem. We would give clients books like Larry’s because the ideas were so important, and we wanted them to understand our approach at a deeper level. Unfortunately, many people simply wouldn’t read them. Not because the books weren’t good. They were excellent. However, they were technical and written primarily for professionals rather than investors.

This dilemma got me thinking…and searching. I wanted something that could open the door a little wider for readers. Something relatable, understandable, memorable, and useful.

So I tried an experiment.

Instead of writing a technical guide, I “buried the vegetables” inside a story.

The result was Odds On: The Making of an Evidence-Based Investor. It follows my own coming of age in the investment world, where readers encounter the mentors, lessons, and ideas that shaped the philosophy behind our firm.

A few years after the book came out, I attended a book party on Park Avenue in New York surrounded by other authors. I struck up a conversation with a writer who had created a popular series of illustrated books. After listening to the story of why I had written Odds On, he paused and said something that stuck with me.

I had never heard the phrase before, so he explained.

The first ring develops the idea. The second ring takes that idea and translates it so a broader audience can understand it.

That description felt exactly right.

Larry was part of the first ring. His work changed how I saw investing. Odds On was my attempt to carry those ideas outward in a way that more people could absorb. More real investors, not just practitioners.

When the manuscript first circulated, a few agents told me the book would fail. It wasn’t prescriptive enough. I was warned that most non-fiction business books go nowhere and help no one, especially if the author does not already have a significant following.

Twelve years after writing it and ten years after publication, the story has been far more powerful and interesting than I ever imagined.

The book has traveled widely. It has been read by students, investors, and advisors across the country. It eventually made its way to the Netherlands, where it was translated into Dutch. Along the way, it sparked conversations, friendships, podcast interviews, speaking invitations, and thoughtful notes from readers around the world.

In many cases, the book became the first handshake between us.

Some readers eventually became clients. Some became collaborators and friends. Some changed the investing philosophy of their entire firm. A few even joined our team.

And in a way, the book changed my life too. Not because of copies sold or opportunities created, but because of the relationships that have grown out of it. Over the years, we’ve received more trust, gratitude, and kindness from long-time clients than I ever imagined possible. Compliance rules prevent us from sharing testimonials, but I can say this: the real riches have come from the people.

What began as an attempt to explain a philosophy ended up creating something much more meaningful: a community of people who believe in taking the long view.

Ideas move through rings. Someone discovers them. Someone translates them. Eventually, someone passes them forward.

That ripple effect is what we’re celebrating in this month’s journal.

Ten years after publication, we’re looking back at the journey of Odds On — the ideas behind it, the unexpected places it traveled, and the people it connected us with along the way.

And if the ideas resonate with you, perhaps the next ring starts with something simple: share the book with someone who might benefit from it.

Take the long view,

Matt Hall

Tax season comes with a lot of moving parts. A missing form, incomplete data, or a late reaction can cost you time and money. Our goal is simple: carry some of that load so you don’t have to.

At Hill Investment Group, we think about taxes all year, because after-tax outcomes matter. Taking the Long View means managing what you keep, not only what you earn.

What we do year-round

Tax awareness is built into the daily work behind your portfolio. 

We place tax-heavy investments in the right accounts to reduce avoidable drag. 

When the opportunity exists, we harvest losses to offset gains while keeping your strategy intact. 

We lean on ETFs where appropriate, which tend to avoid the surprise capital gain distributions that show up in many mutual funds. 

When cash flow, withdrawals, or charitable giving are part of your picture, we help coordinate the timing and structure so everything stays aligned with your plan.

What we do during tax season

Tax season should feel orderly. For clients where we manage the full relationship, we coordinate directly with your tax preparer, track form releases and revisions, and prepare a clean packet with the core reports your CPA needs. 

No hunting through portals, no guessing which forms matter.

For clients earlier in their journey with us, many of these same principles are at work in how we manage your portfolio, and we’re always happy to point you in the right direction.

The goal, as always, is to make this easier for you.

What you still need to handle yourself

Some items live outside Hill, like W-2’s,  old employer retirement plans, accounts held elsewhere, K-1s, and certain custodian forms.

Easy to miss items

• IRA Form 5498: Useful for keeping contribution and cost basis records accurate over time.
• HSA Form 1099-SA: Required if you took money out of an HSA.
• Qualified charitable distributions: Your 1099-R will not label a QCD for your CPA. However, if we facilitated it, we would help send a list to your CPA.

If you want to talk through tax planning as part of your broader plan, reach out to us at service@hillinvestmentgroup.com.

Every February, I open one envelope with unusual curiosity: my 1099 from our custodian. It shows how much “income” my investments produced last year.

As an investor, I appreciate what that number represents. As a taxpayer, I also know what comes next: plugging it into a projection and watching how it changes what we’ll owe in April.

For me, it’s manageable. I’m still early in my career, and my portfolio is mostly stocks. But for many of the families we serve at Hill, this number can grow large enough that it doesn’t only affect their tax return — it starts to affect their entire financial plan.

And historically, there hasn’t been much we could do about it… until now. 

Longview Advantage Fixed Income ETF (LVIG) is an ETF from our research partner, Longview Research Partners. Its aim is to solve a part of planning we historically could not control: Traditional bond investments generate taxable income whether you need it or not.

LVIG is built to avoid those automatic income distributions. Meaning more of the return stays inside the portfolio, which gives us control over how income shows up in your plan.

Like EBI, LVIG will be used inside Hill’s models. It may not be noticeable for younger, equity-heavy investors today. But as portfolios shift over time toward a higher allocation of fixed income, LVIG becomes a meaningful planning tool as well as an outstanding investment.

1. Roth IRA conversions: Less portfolio income means more flexibility to convert traditional Individual Retirement Accounts (IRAs) to Roth IRAs during lower-income years.

2. Asset location: We can comfortably hold fixed income in taxable accounts and reserve IRA and Roth space for equities, where long-term growth benefits most.
   
   
3. Medicare and income cliffs like IRMAA (Income-Related Monthly Adjustment Amount), NIIT (Net Investment Income Tax), AMT (Alternative Minimum Tax):  Keeping income lower makes it easier to stay below thresholds that trigger higher premiums and additional taxes.
   
   
4. Trust planning: Trusts hit top tax brackets more quickly than individual tax brackets. Therefore, minimizing ordinary income allows trustees to distribute based on need, not tax pressure.
   
   
5. Estate planning and step-up in basis: More return remains to compound as unrealized growth that may receive a step-up for heirs instead of getting taxed each year.
   
   
6. Capital gains control: Lower income gives us more favorable opportunities to harvest gains at lower tax rates.
   
   
7. Retirement cash flow: We can create distributions intentionally by selling shares at long-term capital gains tax rates rather than generating unpredictable taxable income.

Most of these benefits become especially impactful for clients who are retired or approaching retirement, have large taxable portfolios, are doing Roth conversions, have trusts, or are mindful of Medicare premium thresholds.

For younger clients, this may feel less important today. But over time, as allocations shift toward bonds, it becomes one of the more impactful planning levers available.

This is a good example of the subtle but powerful improvements we like making for clients at Hill Investment Group. Changes that not only improve your investment outcomes, but also make your plan work better behind the scenes.

While LVIG is something we are bringing to Hill portfolios, it will be a publicly traded ETF and available to all investors. Therefore, if you know someone navigating retirement, taxes, or trust planning who could benefit from greater flexibility, feel free to share this with them or have them reach out to us directly to see how we can be most helpful. Here’s the best link to get in touch with us.