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

I keep hearing that AI is going to replace financial advisors and other knowledge professionals.

Here’s the reality.

The information has always been out there.

You could Google how to build a financial plan 15 years ago. You can ask ChatGPT today. That doesn’t mean you have one.

Six-pack abs are the perfect analogy.
The workouts are free. The nutrition plans are free. The science is clear.

And yet most people don’t have them.

Not because they lack information.
Because they lack execution and accountability.

Financial planning is no different.

The real value isn’t in generating ideas. It’s in:

• Structuring them correctly
• Catching the mistakes before they become expensive
• Keeping you from stepping on landmines
• And helping you execute when emotions get loud

AI is a tool. A powerful one.

But tools don’t replace judgment, context, or behavioral coaching.

And they certainly don’t sit across the table when markets drop 20% and remind you why you built the plan in the first place.

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

Exits reward preparation, not just performance.

Two founders can sell similar businesses for similar numbers and walk away with very different outcomes.

The difference isn’t luck.
It’s decisions made long before the deal was ever discussed.

Is it just me, or did sleep become the most valuable currency overnight?

Eight hours feels abotu right.
Six hours feels reckless.
Anything under 7 and I’m negotiating with myself all day.

I used to brag about running on fumes.
Now I guard bedtime like it’s a board meeting.

Please tell me this is normal.

Many founders are financially successful and financially anxious at the same time.

High net worth, but low liquidity.
Strong revenue, but unpredictable income.
Big upside, but unclear timelines.

That tension is normal.
Ignoring it is not.

Reinvesting everything back into the business sounds disciplined.

Sometimes it is.
Sometimes it’s avoidance.

Liquidity creates options.
Options create leverage.

A strong personal balance sheet doesn’t weaken your business.
It strengthens your ability to make better decisions.

AI is not the threat people think it is.

It’s a force multiplier.

For professionals who know what they’re doing.

The mistake is thinking that asking a chatbot a few questions equals real planning.

It doesn’t.

Planning is layered:

Business structure.
Tax exposure.
Liquidity timing.
Estate coordination.
Behavior under stress.

Miss one layer and you can create a cascading problem.

AI is helpful at surfacing options.
It is not yet reliable at spotting second- and third-order consequences.

That’s where experienced professionals still earn their seat at the table.

Optimization is nice.

Avoiding landmines is essential.

Experience in financial advice isn’t about knowing the newest products. It’s about recognizing patterns.

What tends to repeat.
What usually disappoints.
What looks great on paper but struggles in real life.

Most shiny objects aren’t bad because they’re evil. They’re bad because they’re mistimed, misunderstood, or misapplied.

Experience brings context. And context is what keeps people from making confident mistakes.

That perspective doesn’t come from headlines or sales decks. It comes from cycles, mistakes, and time.

Experience isn’t about knowing the newest strategy.
It’s about recognizing patterns.

What tends to work.
What usually disappoints.
What looks great on paper and fails in real life.

That perspective is hard to Google.

In business, long-term thinking is a competitive advantage.
In investing, it’s the same.

Most people aren’t underperforming because they lack information. They’re underperforming because they change direction too often.

A plan only works if it’s given time to work. Constant adjustments may feel responsible, but they often undermine the very outcomes people want.

The advisor who keeps you anchored to long-term outcomes isn’t limiting you. They’re protecting your edge.

I love building. I love competing. I love growing.

But my business is a tool. It’s not who I am.

If everything you built disappeared tomorrow, who would you still be?

That question has a way of clarifying priorities.

The best stories always sound like this:
“This is the moment.”
“This is different.”
“This time it’s obvious.”

That’s how marketing works.

A good advisor’s job is to slow that moment down and ask:
Does this actually move the plan forward?

Most of the time, the answer isn’t exciting.
It’s effective.

“Won’t AI replace financial advisors?”

Short answer: no.

Long answer: it depends on what you think a financial advisor actually does.

If you believe it’s just running numbers and producing a report, then yes — software has been doing that for years.

But that’s never been the core value.

The value is:

• Seeing around corners
• Coordinating tax, estate, business, and personal decisions
• Stress-testing assumptions
• And protecting clients from catastrophic errors

I’ve intentionally tested AI with complex scenarios.

It’s impressive. It’s also still wrong in ways that would be financially painful if someone blindly followed the output.

AI can generate possibilities.

It cannot yet own the consequences.

And that difference matters.

If you're worried about your job security or whether your business will weather what's coming, that's actually the perfect signal to get your finances in order right now. 

Uncertainty has a way of exposing the gaps in our financial plans that we've been meaning to address for years. 

We're helping clients build that safety net every single day, and the ones who act early are the ones who sleep better at night. 

Don't carry financial stress on top of everything else you're already managing. 

Reach out to me or another financial advisor and let's start building your resiliency plan.

Here's the thing about economic uncertainty: you can't control what's happening in your industry, your market, or the broader economy. But you can absolutely control whether you have a solid financial plan backing you up when things get hard. 

The business owners and professionals I work with who feel most confident right now aren't the ones with the most money. 

They're the ones who know exactly where they stand and what they can weather. 

That peace of mind is worth more than people realize. If you don't have that clarity, now is the time to get it.

The work of keeping what you earn doesn’t start at the exit.

It starts with:

Structure

Timing

Tax awareness

Risk management

Each decision compounds quietly.
So do the mistakes.

Let me save you $47,000 in taxes this year.

Just kidding. I have no idea what your tax situation looks like.

But someone on this platform will make that promise today — and some of you will believe them.

Here's what real tax planning actually looks like for the business owners I work with:
It's boring. It's detailed. And it starts with understanding your LIFE before touching your returns.
→ Are you planning to sell your business in 3 years or 15?
→ Do you want to fund your kids' education or are they figuring it out?
→ Is charitable giving part of your values or not?
→ What does your income look like this year vs. next year vs. five years out?

Once we know THAT, we can talk about:
Entity structure optimization
Retirement account strategies
Charitable giving vehicles
Capital gains harvesting
Income timing and deferral

Every one of those tactics is a lever. But a lever only works when you know what you're trying to move.

I don't do tax planning in a vacuum. I do tax planning inside a comprehensive wealth strategy that's built around your goals, your values, and the life you're trying to live.

Because saving $10K in taxes means nothing if you're still building someone else's version of success.

What's one tax strategy you implemented that you wish you'd done sooner?

#taxplanning #businessownertaxes #wealthmanagement #financialstrategy #smallbusinessfinance

If asset allocation is the first conversation, the planning is already backwards.

Founders need to answer:

What risks am I already taking?

Where am I illiquid?

What decisions are coming next?

Only then do investments make sense.

Aggression builds businesses.

But structure protects wealth.

At some point, wealth needs to become more than a scoreboard.

It needs to become:
• Stability for your family
• Freedom of time
• Optionality around what’s next

That requires structure:
• Intentional investment strategy
• Risk management
• Tax coordination
• Exit modeling

Aggression builds income.
Clarity turns it into freedom.

Business owners already understand this lesson, even if they don’t always apply it to their money.

You didn’t build your business by pivoting every time a new idea appeared. You picked a direction, refined it, stayed uncomfortable longer than most, and resisted distractions along the way.

But when it comes to personal finance, that discipline often disappears. A headline hits. A friend shares a strategy. A new product gets attention.

Suddenly, the patience that built the business is replaced by constant tinkering.

Your financial life deserves the same long-term thinking that made your business successful in the first place.

substack.com

Little Reminder (@littlereminder)

I deliver net-new acquisition, win net-new logos, and drive double-digit ARR growth across mid-market and enterprise Cloud, AI, and IT solutions through disciplined, value-based execution. I lead with the belief that how we work matters just as much as what we build.

Alexandrea S.

Just shipped.




My mom cookies. Comment if you want the recipe. 👆

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