I am a native Chicagoan, father of 3 wonderful children, and a 20 year veteran of the financial services industry. 

-I am passionate about working with business owners who would benefit from having an objective partner in their financial lives.   
-I am trying to help my clients realize their best selves. We use financial tools to help them achieve the freedom, control, or time that they desire. 

How do I know if I'm a good fit?

-Business Owners between 35&55 who want to have the ability to make work optional

-Household income of at least $150,000

-People who want to delegate so you can spend more time with the people they care about and doing the things they love


What is the benefit of working with Chris?

-Create an easily understandable 1 page financial gameplan so you always know what the next steps we will take are

-Knowing there will be a day when you can make work optional so you can have a defined goal to work towards.

-Optimize insurance policies to maximize coverage and reduce costs.

-Proactive tax planning to minimize your lifetime tax bill

-Provide financial partnership and help solve your financial problems so you can focus on the most important things in life

 I love working out, cooking, bourbon and cigars. 


Please note: While I appreciate endorsements of my services, I cannot accept endorsements or recommendations on my LinkedIn profile, as these are considered a prohibited testimonial under SEC regulations.

I can be reached at (312) 850 3600 x16 or you can schedule at https://app.acuityscheduling.com/schedule.php?owner=12813504&appointmentType=1941784

Securities offered through The O.N. Equity Sales Company, Member FINRA/SIPC, One Financial Way, Cincinnati, OH 45242 513.794.6794. Investment Advisory Services offered through the O.N. Investment Management Company

Christopher Clepp

Is it just me, or did alcohol suddenly come with terms and conditions?

One drink is enjoyable.
Two drinks require water.
Three drinks require a full recovery plan.

I still like the IDEA of drinking more than the aftermath.

Please tell me I’m not alone here.

President @ Building Towards Wealth | ChFC, Financial Planning, Wealth Management

Honest Question About Coffee 

Is it just me or does one cup of caffeinated coffee now feel like the exact right amount?

Two cups and I’m wired.
Three cups and I’m questioning my life choices.
Any more and I’m no longer a functional adult.

Somewhere along the way, my tolerance quietly retired.

Please tell me I’m not alone.

Entrepreneurs create something from nothing, often at a level of sacrifice most people never see.

You carry risk, financial, emotional, reputational.
You shoulder obligations, employees, clients, lenders, family.
You show up every single day because no one else will.

But when success finally materializes, the landscape shifts.
Suddenly it’s taxes, liquidity decisions, planning, and navigating the implications of the wealth you’ve built.

This is the part no one prepares business owners for:
The complexity doesn’t end when the struggle does.

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Business owners often say, “My money is tied up in the company.”
Exactly.

That concentration is the reason planning matters.

Not to diversify prematurely, but to manage risk, liquidity, and optionality while you’re still in control.

Turning 50 this year has clarified something for me.

Nothing is more important to my quality of life than my physical fitness.

It keeps me sane when work is heavy.
It gives me energy instead of stealing it.
And most importantly, it lets me keep up with my 5- and 7-year-old without feeling like I’m borrowing energy from tomorrow.

These days my routine is simple and sustainable:
• Cardio
• CrossFit
• Strength training
Usually five days a week
Rest days look like long walks or yoga

It’s not about aesthetics.
It’s about capacity.

Curious, what are you doing right now to maintain your physical fitness?

When Doing the Right Thing Isn’t Enough

I don’t often tell stories about clients we part ways with. The handful of times it has happened, those chapters close quietly and respectfully.

But occasionally, there’s a lesson worth sharing. 
We started working together with clarity. We laid out the objective for a specific investment account. Not hypotheticals. Not market-beating ambition. A clearly defined role for this money within a larger life context.

The mandate was conservative by design.
The time horizon was long, roughly 15-20 years.
The purpose was stability, liquidity, and reliability.

This wasn’t “swing for the fences” money. It was foundational money. Money that needed to do its job quietly and predictably.

And for 18 months, that’s exactly what it did.

We measured against the objectives we agreed on. The approach was disciplined, regardless of market conditions.

In March of 2025, when markets pulled back, we stayed the course.
When they rebounded, we stayed the course.

Not because we were stubborn.
Because the plan didn’t change.

There were calls and emails prompted by headlines, forecasts, and predictions.

Each time, the conversation came back to the same place.
We are investors, not traders.
This portfolio wasn’t designed to react to every piece of news.
Changes would happen at the margins, thoughtfully, deliberately, and rarely.

Despite that, dissatisfaction persisted.

Not because the goals weren’t met.
Not because the results were poor.
But because there wasn’t enough activity.

After revisiting the same issue multiple times, it became clear. We weren’t misaligned on performance. We were misaligned on philosophy.

Ultimately, we decided to part ways. The client chose to move the funds into a savings account. He expressed frustration about paying fees, even though the portfolio was performing well after factoring in those fees.

That’s on me.

From the start, this relationship was too focused on returns and not enough on planning, despite my guidance. Planning is what we lead with. Returns matter, but they are a byproduct of a disciplined process, not the purpose of the relationship.

Cost is only a factor in the absence of value.
And value looks different depending on what you believe progress actually is.

For some people, movement feels like progress.
For others, discipline does.

Sometimes, the hardest work in investing isn’t making a decision.
It’s having the patience to do nothing when doing nothing is the right move.

Mistaking activity for productivity is one of the most expensive mistakes an investor can make. And it’s a line I won’t cross, even if it means saying goodbye.

Because my responsibility isn’t to make portfolios busy.
It’s to make plans work.


The scenario is for illustrative purposes only and is not a recommendation. All investing involves risk, including possible loss of principal. Past performance is not indicative of future results.

Entrepreneurs are wired to see opportunity where others see danger.

That instinct is why most people never start a business, and you did.

But pushing through risk works best when effort directly changes outcomes.
In business, mistakes can be fixed with better hires, better systems, better execution.

In personal planning, time and capital behave differently.

Some risks compound quietly. Some mistakes don’t show up until there’s no clean reset.

The skill isn’t being less bold.

It’s knowing where boldness actually pays.

The instincts that make someone a great entrepreneur are powerful.

They also don’t always translate.

In business, reinvention is often necessary. Markets shift. Products evolve. Competition forces adaptation.

Personal wealth doesn’t operate the same way.

Constant tinkering, reacting, and pivoting often introduces more risk than reward. Wealth is built through alignment, patience, and repeating sound decisions over long periods of time.

What creates revenue growth doesn’t always create financial security.

Different arena.
Different rules.

We remember the winners.
We forget the graveyard.

For every innovation that reshaped the world, there were countless others that promised the same thing and quietly disappeared.

When making financial decisions, this matters.
Chasing the next big thing often ignores the far more powerful driver of long-term success: consistency.

Boring done well beats exciting done poorly.

This weekend is the deadline to help my daughter, Kari’s school reach their $2k fundraiser goal!
- Buy a Domino’s Slice The Price (STP) card for just $20, and the school earns $10 for every card sold.
- With the card, you can purchase unlimited large pizzas at Domino’s, and with each purchase you receive another large pizza! e.g. buy 10, get 10 FREE!
- Use the card as many times as you like for the whole year (think Super Bowl party, kid’s bday parties, etc)

Open article: Help us raise $2,000! — Kari Clepp & Hawthorne Scholastic Academy PTA by store.dominos.cards

Help us raise $2,000! — Kari Clepp & Hawthorne Scholastic Academy PTA

Traditional planning assumes predictability.

Entrepreneurial life is anything but predictable.

Real planning for business owners isn’t about perfect projections.

It’s about building flexibility into every decision.

I’m always on the lookout for great book recommendations.

A few favorites from this year that really stuck with me:

• The Art of Spending Money by Morgan Housel
No surprise here. He’s still my favorite writer. Clear, grounded, and endlessly re-readable.

• Atomic Habits by James Clear
I re-read this again. Every time I pick it up, something different clicks depending on the season of life.

• Anything by Ryan Holiday, especially his most recent, Wisdom Takes Work
Consistently practical reminders that growth and perspective are earned, not downloaded.

What are you reading right now?
What have you enjoyed or re-read recently?

Always looking to add a few good titles to the list.

Every generation believes it’s living through unprecedented change.
Some of that is true. Most of it isn’t.

Airplanes changed travel.
The internet changed communication.

But for every true breakthrough, there are dozens of ideas that were simply new, not better.
Novelty grabs attention. Fundamentals create outcomes.

In investing, business, and life, the question isn’t “Is this new?”
It’s “Does this actually improve the end result?”

A 9-to-5 plan optimizes savings rate.

A business-owner plan optimizes decision-making.

Those are very different objectives.

More feels productive.
More feels sophisticated.
More feels like progress.

But more is often just noise.

More accounts don’t mean better outcomes.
More strategies don’t mean better results.
More complexity doesn’t mean better control.

In fact, complexity often hides the absence of clarity.

The strongest financial plans are calibrated, not maximized. They’re built around enough—enough growth to meet goals, enough liquidity to stay flexible, enough risk to move forward without putting everything in jeopardy.

Optimization without purpose is just accumulation.
Enough is intentional.

Simple feels uncomfortable.

Complexity gives the illusion of control and intelligence.
But complexity without purpose usually just increases the chance of mistakes.

The most effective financial strategies are often simple, repeated consistently, and rarely exciting.

That’s not a flaw.
That’s the point.

Most entrepreneurs are comfortable with concentration.
One product. One market. One big bet.

That focus is often exactly what makes the business work.
Clarity beats diversification early on.

But personal wealth built the same way introduces a different kind of risk.
Not visible day-to-day. Not dramatic. Just quietly compounding exposure.

Success doesn’t require copying the business playbook everywhere.
Sometimes it requires knowing where not to use it.

Business owners don’t just have portfolios.

They have enterprise value, key-person risk, tax strategy, liquidity events, and optionality.

If your advisor is only talking about markets, you’re getting a partial conversation.

Wealth leakage is rarely dramatic.

It’s small decisions, made repeatedly, without a framework.

Founders don’t lose wealth overnight.
They lose it slowly, without realizing it.

“I’ll focus on my personal finances after the exit.”

That’s like saying you’ll worry about taxes after April 15.

The decisions that determine what you keep are made years in advance.

Planning early isn’t about slowing you down.

It’s about protecting the upside you’re working so hard to create.

Entrepreneurship Educator | Coach | Consultant | Lean Startup Specialist | Entrepreneur | Author | Helping entrepreneurs find the next-level solutions to grow their ventures.

Are you tired of the hype around entrepreneurship? So am I. Entrepreneurship isn't a punchline; it's a critical life choice. Unfortunately, too many influencers practically dare people to leave their careers and go all-in as founders.

Time to get real about entrepreneurship.

After 30 years as an entrepreneur and 22 years as an educator, I’ve seen too many smart, hardworking people burn out chasing someone else’s idea of success. It’s time for something different.

Whether you’re escaping the corporate grind or already running a venture, I'm focused on:

→ The realities of small business

→ Systems to simplify your workload

→ Time management to free up your life

→ Financial intelligence for long-term security

As someone who has faced burnout, imposter syndrome, and the challenges of balancing work and family life, I know firsthand what it takes to create sustainable success.

My mission is simple: achieve holistic success—financial well-being, mental wellness, purpose-driven living, and empowered independence.

DM me if you'd like to talk about your future.

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