Timothy R. Jester, CFP

03/22/2026

Most founders and business owners don’t make bad decisions because they’re dumb.

They make them because they’re cornered.

Here's something I read today from clear thinking by Shane Parrish.

“A good position allows you to think clearly rather than be forced by circumstances into a decision.”

Financial planning is the same.

It’s not primarily about picking the best investments.

It’s about engineering a position where you’re never forced into bad ones.

When you don’t have enough liquidity or margin in your personal finances or flexibility in your business, you don’t get to “decide.”

You react. You take the deal you shouldn’t take. You sell equity too early. You pass on opportunities you should pursue.

The best founders and business owners don’t just make better decisions.

They build positions that give them the luxury of making them.

Where in your life or business are you currently forced into decisions?

03/11/2026

“Most people are sitting on their own diamond mines. The surest ways to lose your diamond mine are to get bored, become overambitious, or start thinking that the grass is greener on the other side. Find your core focus, stick to it, and devote your time and resources to excelling at it.”
-Gino Wickman from his book, Traction

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07/23/2025

By any measure, Sven is a successful guy.

He began building his business from nothing 18 years ago and with a tremendous amount of grit, a lot of late nights and a dream he refused to let go, he’s now running a company worth more than $5 million.

On paper, he is wealthy.

Sven has been wise with his money. He has a well-diversified portfolio of invested assets and retirement accounts. He owns a few pieces of real estate, including the building housing his business. And if he dies, he has a couple million dollars of term life to take care of his family.

But in reality, most of his net worth is locked up inside the business and his real-estate holdings and not in liquid assets his family can easily access.

During a recent planning session, I asked Sven a couple of questions that got him thinking.

“Sven, if you die suddenly, what will actually happen to your business?”

“Would your wife, Sara, know how or want to keep running it?”

“Could or would your kids step in?”

“Would your partner buy Sara out fairly and quickly?”

“How fast would the bank call in debts?”

These are all questions that had crossed Sven’s mind but he’d pushed off and not wrestled with because they take time and energy and let’s face it, they’re not fun questions to ponder.

But that’s what I’m here for. And I was able to help Sven and his family utilize a couple of financial planning tools that solve these issues while further diversifying his portfolio and adding peace of mind about what would happen to his business when he passed.

If you own a business and you’ve asked yourself any of these questions and you’d like to talk them out, message me.

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07/03/2025

You Bet on Yourself to Build Wealth. Is The Same Bet Building Freedom?

I often hear successful entrepreneurs say things like this when we talk about investing outside of their businesses.

“My business gives me the highest ROI. Why dilute that?”

Or “all my success has come from betting on myself. Why change the formula?

And these are good questions to wrestle with!

You know your business better than anything else. You control the outcomes. You understand the risks and historically, your business has probably generated 20%, 30% or maybe even 50% returns.

“No other investment can touch that!” you say.

But here’s the counterweight.

Investing outside of your business isn’t about beating your business. It’s about building personal liquidity, diversifying away from your biggest holding (and let’s be honest, maybe your biggest risk) and eventually giving yourself freedom to not always be on the grind.

And here’s the kicker…the market isn’t the only other place to put money outside of your business. There are hundreds of different strategies that can help you diversify, reduce risk, mitigate income taxes, delay capital gains taxes, pay estate taxes without burdening your beneficiaries, grow your estate and experience good returns, even if the returns aren’t the same as your business returns.

So here’s the bottom Line. You're not investing outside of your business instead of your business. You're investing outside of your business to protect the life your business is building and to preserve the wealth and legacy you want long after you’ve separated from your business.

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07/02/2025

Great financial planning isn’t just about maximizing investment returns. It’s about aligning money with meaning, and that is deeply personal.

Personal meaning is also something, in a world of eye-catching emotionally manipulative headlines and doom scrolling, we don’t often take the quiet time to contemplate.

One of the most overlooked truths in financial planning, even by most advisors, is that financial decisions are emotional before they are logical.

We often present financial planning as a spreadsheet exercise: inputs, projections, tax optimization, and risk management. But beneath the surface, money decisions are wrapped up in identity, fear, security, legacy, guilt, ego, and more than you might imagine, even trauma.

Most people don’t make financial choices based on math alone. They make them based on what feels safe, what aligns with their self-image, what reduces stress, or what helps them sleep at night. And most advisors, even good ones, tend to underemphasize this emotional layer.

The most impactful advisors understand this and make space for it.
They don’t just ask “What’s your risk tolerance?” They ask, “What keeps you up at night?”

“What does money mean to you?”

“What would financial peace look like for your family?”

Make sure these are the questions you’re considering with your advisor.

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06/30/2025

THE MARKET IS HIGH :)

The market is at an all-time high today and there are a couple of different reasons for this most people aren’t considering. These reasons are also why the stock market doesn’t really feel how our personal checkbooks feel.

While interest rates, inflation, politics and war dominate the headlines, there are quiet forces at play pushing markets forward that have nothing to do with market trends, economics or politics.

The first reason has to do with scarcity. Scarcity creates value and over the last 20 years we’ve seen the number of available stocks shrink considerably. In 2005 there were 2,800 – 3,000 stocks available for purchase on the New York Stock Exchange (NYSE) and today, because of the steady consolidation of corporate America and the influence of private equity buying public companies and taking them private, there are only 2,300 – 2,400 stocks available on the NYSE.

But demand for stocks has only gone up.

While the availability of stocks has decreased, passive investing has fundamentally altered market behavior. Passive investing (what most investors do) is where investors buy into a selection of exchange-traded funds or index funds. These funds buy stocks and bonds in proportion to their index weight and not based on any performance metrics or financial outlook.

This trend has created a constant flow of capital into the largest stocks causing some of the overvaluation we’re seeing. This is particularly visible right now in tech stocks and the Magnificent Seven that are over-proportionally driving the value of the S&P 500.

Together, these two dynamics are quietly reshaping market mechanics. They don’t get the same coverage as Fed decisions or economic numbers because they don’t generate daily headlines, but their impact is substantial and it's among the reasons the stock market continues to grow while our checkbooks keep getting tighter.

This is not investment advice.

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02/20/2024

"...according to a new report from Deutsche Bank, profits at these seven tech giants [Apple, Amazon, Alphabet, Meta, Microsoft, Nvidia and Tesla] are greater than the profits of all publicly traded companies in nearly every G20 country. And in terms of market value, they’d be the second-largest national stock exchange in the world."
-Excerpt from Morning Brew

01/02/2024

I'm looking forward to what 2024 holds in store.

It's going to be tough. The last couple of years have taught me tough has to be a forgone conclusion. But we've managed to traverse tough pretty well and we'll face whatever tough this year brings.

I think what's most exciting is looking back over the last couple of years and seeing significant progress in spite of the tough. In every metric we've grown at least a little and experiencing growth is deeply gratifying.

So, here's to all the good to come and continuing to grow in 2024.

11/01/2023

United States Gross Domestic Product printed a whopping 4.9% growth in Q3 2023. Research company Eagle Life is estimating over 1.5% of that can be attributed to Swifties going to Taylor Swift concerts and buying Taylor Swift merchandise.

09/23/2023

"The S&P 500 has added ~$7.2 trillion in market cap in its rally this year.

However, the top 20 largest stocks have accounted for $6.1 trillion of that gain.

This means that the top 20 stocks in the S&P 500 have accounted for 85% of the index's gains.

Meanwhile, 5 stocks currently account for ~70% of the Nasdaq's gain this year.

All while technology stocks now reflect a record ~25% of all equity fund assets.

A few stocks have become the backbone of this market."

From The Kobeissi Letter

01/10/2023

Do all Ponzi schemes come with wild hair and unrealistic returns? 😂

01/05/2023

"The biggest generator of long-term results is learning to do things when you don't feel like doing them. If you let excuses or emotion drive behavior, you're cheating your future self. Put aside the excuses and start doing what you need to do." -Shane Parrish