Erik Reid

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

Last night I had the chance to co-host an event with Jason Jacobsohn of Propellant Ventures and Paul Sippil at Birch Road Cellars, and it was exactly the kind of room you hope for.

A packed space filled with thoughtful, ambitious business owners from across the Chicagoland startup community. Founders building real companies, navigating real challenges, and having smart conversations about growth, risk, capital, and what’s next.

These events are simple by design. No formal programming, no pitches, no overproduced agenda, just good people in the same room having honest conversations and building relationships that actually matter.

If you’re a business owner in Chicago and would enjoy being part of a room like this at a future event, reach out. We’re intentionally bringing together founders who want to grow, learn, and support each other without the noise.

Advocate, Advisor, Resource, and Connector for Entrepreneurs

We had a great time at our VIP Business Owner & Investor Soiree. Thank you Building Towards Wealth and Paul Sippil for co-hosting the event. Christopher Clepp Propellant Ventures

Everyone on social media is fired up about Sam Darnold “paying more in California taxes than he made for winning the Super Bowl.”

Let’s slow that down for a second.

Yes, California has what’s commonly called the “jock tax.” When professional athletes play in a state, that state gets to tax the portion of income allocated to the days they worked there.

And California’s top income tax rate is over 13%.

Here’s the important part most people are missing:

He isn’t being taxed only on his Super Bowl bonus. Under the duty-day allocation formula, a portion of his entire season’s compensation gets assigned to California because the game and prep days happened there.

So when headlines say he owed more in California taxes than his game check, they’re comparing:

• The Super Bowl bonus
vs.
• The California tax on the income allocated to that state

That makes for a dramatic headline.

But it doesn’t mean he “lost money” playing the game. It means high earners in high-tax states experience real multi-state tax complexity.

And this isn’t just about athletes.

If you’re a founder, executive, or high earner doing business across state lines, multi-state tax exposure is very real. Where you work, where you sell, and where liquidity events occur can materially change your tax bill.

The lesson isn’t outrage.

It’s planning.

High income + high mobility + high tax states = complexity.

And complexity favors those who prepare early.

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.

One thing I know for sure, our most limited resource isn’t money.
It’s time.

One of my favorite changes I made this year was adding a weekly breakfast with my mom, who is in her 80's.

Every Friday morning, we go to a restaurant, sit down, and just talk. About life. About the world. About how she’s doing. About how the kids are doing. She still comes over to see her grandkids, but this time feels different. It’s intentional. It’s ours.

The truth is, I’m very aware that I have a limited number of these Fridays left.

And I never want to be on the other side of this, looking back, wondering why I didn’t do better when I had the chance.

There have been moments in my life where something happened and, in hindsight, I wish I had shown up differently. I wished I had been more present. I wished I had made the time. I promised myself I wouldn’t repeat that pattern.

So this year, I didn’t overthink it. I just put it on the calendar.

If you’re reading this, I’d encourage you to think about one small thing you could start doing now, something future-you will be grateful you didn’t put off.

Not because it’s efficient.
Not because it’s productive.
But because one day, you won’t be able to do it anymore.

Is it just me or does eating “whatever you want” come with consequences now?

One bad meal and I feel it for two days.
Late-night food hits different.
And vegetables feel less like a suggestion and more like a requirement.

This feels unfair, but here we are.

Most financial planning assumes:

Predictable income

Stable career paths

Clear separation between work and life

Founders live in the opposite world.

Variable income.
Concentrated equity.
Personal decisions tied directly to business outcomes.

If the plan doesn’t match reality, it won’t get used.

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.

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.

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.

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.

Shiny objects feel like action.

They give the same dopamine hit as progress.
You’re learning. You’re adjusting. You’re “doing something.”

But business owners know this trap well. You can spend months chasing new ideas and still be in the same place, just more tired.

Personal finance works the same way. Constant changes don’t create momentum. Consistency does.

Real wealth is built quietly.
Boring plans.
Unsexy discipline.
Repeated decisions done well over long periods of time.

An advisor who keeps you focused when the noise gets loud is often doing more work than it looks like.

Signing the front of the check changes how you think about money.

Cash flow feels different.
Risk feels personal.
Decisions carry weight beyond spreadsheets.

Founders don’t just manage finances.
They manage consequences.

That reality deserves a different kind of planning.

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.

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The Battle

Erik Reid

Christopher Clepp

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