When Matt told me he was writing a book, I supported him.

I also wasn’t sure what would come of it.

We had always believed in what we were doing. We had great clients. We were growing. We were already sharing our philosophy with the people we worked with. Part of me wondered if we really needed a book at all.

But Matt felt strongly about it. He wanted to put something out into the world that might help people see things more clearly. So we backed him.

The first line of the book was, “I want this book to change your life.”

That is a big statement. At the time, I didn’t know what to make of it. Turns out, that Odds On is unique – it is not only informative about investing, but it is also engaging on so many other levels.

Over the last ten years, we’ve kept notes from people who read it. Clients, advisors, students, friends, and plenty of people we had never met. Reading back through them now, what stands out is not that people liked the book.

It’s what they did after they read it.

• “I was completely engaged from the first paragraph and couldn’t put it down.”
• “I did not take one break from reading until I was finished, simply because I did not want to put it down.”

Some people found clarity.

• “I was up until after midnight reading your book, and it changed my entire perspective on investing strategies.”
• “Until I picked up your book, I was losing hope for our profession. Your book gave me a much needed breath of fresh air.”

• “We are gradually converting all our existing clients and spreading the word to others in our office.”
• “I found your story so inspiring that I am seriously thinking of leaving my current job to start something new.”

And some of the most meaningful notes had very little to do with investing.

People who had gone through their own medical challenges wrote to Matt after reading his story. They shared things they don’t usually share. That part of the book reached people in a different way.

The book also ended up in places we never expected. Conference rooms. Classrooms. Zoom calls. Podcasts. Libraries. We heard from someone connected to the management of a university endowment who asked their board to read it, hoping it might shape how they approached their decisions.

And then there are the stories that just stick with you.

One of my favorites came from an old friend of Matt’s he hadn’t seen in years. He gave the book to his doctor. The next time he saw him, the doctor walked into the room and skipped everything else. He just wanted to talk about the book.

“When he came into the room he did not ask me how I was doing, he immediately went to talking about the book.”

That’s when it hit me.

The book was doing something we couldn’t have done on our own. It was reaching people at the right time, in their own lives, in their own way.

Ten years later, I don’t think about whether the book was a success.

I think about the people who wrote in to us about it. The ones who made a change. The ones who saw things a little more clearly.

That doesn’t happen very often.

I’m glad Matt wrote it.

And I’m grateful for where it went.

Here’s to the next ten years of learning, sharing, and taking the long view.

If you’re feeling pulled around by headlines, Odds On was written for moments like this. It’s a reminder that better decisions come from a clear process, not a hot take.

Start with the Intro to Odds On. We’re sharing it as a short PDF, linked below, so you can get a quick taste of the book, or re-read it as a reset when you need one.

Our suggestion: Read the first sentence. Then read it again slowly. Think about it for a minute. Read it one more time. Then dig in. See where the journey takes you. Many others have found the read transformational. Please share your experience!

Read the Odds On Intro 

If you’d like a full copy, we’re happy to send one to you or to someone in your life you’d like to share it with. Physical book, Kindle, or audio. Your choice.

Request Odds On

If you want to talk more about how to put the philosophy into action, email Buddy directly at buddy@hillinvestmentgroup.com. We’ll help you apply these ideas to your situation and map a clear next step.

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.