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)

Tiffany Napper, Upleveler Society

When I set out to spread my wings in early 2011, one of the first projects I accepted was the Unit Publicist for a Hollywood film starring Rose McGowan. I was asked to bring my creative, social campaign thinking to their promotional efforts, and we filmed and released daily videos to build hype and help land covers and features in the industry's biggest publications.

I continued working in the music industry, representing Live Nation, Grandmaster Flash, Marc Cohn, Hot 8 Brass Band, Flow Tribe, Maggie Koerner, Robin Barnes, and more over the years. 

Other creatives also trusted us to secure their press and accolades, including Rebecca Rebouche, who earned the cover of Garden & Gun under our public relations guidance.

But no matter if we were working on concert promotion for Live Nation or hearing aids promotion for Signia, we always operated from a customer-first mentality, constantly asking ourselves how we can stand out in their eye and exceed their expectations.

With full-service branding and social media offerings under our umbrella, we were always more than smart press releases. We ensured that your online branding, your social media strategy, and your PR strategy all told a cohesive - and riveting - story.

We took pride in creating multi-faceted campaigns that took your brand to the next level and connected you to the right audience.

In 2020, I was asked to host a workshop and teach other creatives how to get through what we thought would be a short, unusual season. Thus my coaching and consulting practice was born, along with the Upleveler Society, a membership for creative businesswomen.

I’m not here for singular success - one profitable year, one good launch. I'm here to teach others how to create businesses that are sustainable and, dare I say it, fun.

We can work together 1:1, in a group program, or through my innovative Momentous Mastermind, which combines business coaching, branding, and PR guidance to help you take up even more space.

PR + Branding Agency Founder + Business Consultant

Flying Fox, New Orleans

Sitting in my New Orleans kitchen, I became aware that the NFL would be implementing a handbag policy for the upcoming season. As a loyal Saints fan, I did a quick Google search for more details, took a tape measure to my handbag collection, and realized I didn't have anything that fit the stipulations.

Another online search showed me that there wasn't much out there that *did* meet the requirements, and the few clear handbags I could find weren't very cute. So I commissioned someone on eBay to design a quick sketch, and that's how I became a handbag designer.

I created one of the very first clear bags in the marketplace that met the stadium regulations, which earned me a fast following and national press attention.

It also caught the eye of the NFL. I was honored to provide handbags for their owner's conventions, sell in their Superbowl pop-up locations, and be featured on their NFL Headquarters' shelves in NYC.

The swift success of Flying Fox (originally Bats on Tees) also earned me a spot with the Idea Village's Big Idea incubator program and granted me access to a Shark Tank success story as a mentor.

(If you're wondering, the eBay relationship, though sweet, was quickly outgrown, and our manufacturing facility moved to New Jersey.)

Using my music industry background, we were creative with our marketing endeavors, and we took Flying Fox on tour for pop-ups at our most loyal boutiques, we created a Flying Foxy influencer campaign that tapped into sorority leaders across campuses, and we collaborated with other designers to grow our reach, including Krewe and Dirty Coast.

Running Flying Fox taught me countless skills specific to product-based businesses, and it allowed me to express myself creatively through a physical medium: PVC and leather.

Nearly 5 years of fun and lessons later, I decided to close the doors so that I could give my full attention to helping other creative entities grow their reach through my PR + branding agency.

Founder and Designer

Yamaha Entertainment Group

I was thrilled to continue my time with Yamaha as a contractor and further flourish in the roles that I loved most: creative direction, public relations, and marketing. 

In 2011, I spent weeks at a time in Caesar's Palace in Las Vegas as we worked with Sir Elton John's team to bring "The Million Dollar Piano" show to life.

In 2012, I was part of a small team tasked with launching Yamaha Entertainment Group, a record label. This took the world's largest musical instrument manufacturing company into uncharted territory and ushered in my first experience promoting an album from ground zero. 

I planned, led and orchestrated a campaign that took the label's first artist, a British rock 'n' roll band, on tour to SXSW. Every component of the trip was branded, filmed, and documented for social media purposes, and it culminated with Yamaha's new band, Leogun, headlining a Yamaha showcase in Austin, TX.

I also worked on campaigns for Nathan East, Josh Groban, Elton John, Alicia Keys, Colbie Caillat, and The Muppets to name a few. I orchestrated social media sweepstakes to grow awareness and cultivate fan experiences, collaborated with influencers to promote new product launches, and quickly grew Yamaha's social media presence to over 100,000 likes. 

Ultimately my role with Yamaha allowed me to combine all of my skills: creative direction, branding, marketing, public relations, social media strategy, live concert production, and video production. Here is a quick peek at the skills I developed in this role: 

•	Marketing
•	Branding
•	Creative Direction 
•	Public Relations
•	Social Media + Digital Marketing
•	Video Production 
•	Concert Production 
•	Artist Liaison 
•	Editorial Management

Public Relations & Creative Director

Once I chose Nashville as my destination, the music industry was at the top of my wish list. I was ready to spread my creative wings, and I quickly secured my seat at one of the most coveted musical enterprises in town, Yamaha. 

This position with Yamaha's artist relations division allowed me to further develop not only my public relations skills but also my marketing and creative skills. 

In this role, I interviewed Elton John, orchestrated a press conference with Alicia Keys, and launched the first social media account for Yamaha on Facebook. I also honed my video production coordinator and interviewee skills and learned just how fun, albeit stressful, live concert production can be.

I was tasked with launching a video production arm to take fans deeper into the world of Yamaha artists. What started as a small two-person show with myself and one cameraman is now a full-fledged Emmy award-winning video production agency under the Yamaha Entertainment Group umbrella. 

In 2011, I opened my own agency (then Bats on Strings, now self-named), but I stayed on with Yamaha for another 7 years, bringing my full residency with them to more than 10 years. Here's a quick peek at some of the tasks I did in those first few years before becoming a contract team member:

•	Led promotional campaigns and content creation 
•	Launched the first social media channel for Yamaha (Facebook)
•	Served as creative director and producer for live concert and video productions
•	Managed web developer and maintained five websites 
•	Wrote news releases and secured media hits to raise artist + brand awareness
•	Planned and drove the award-winning "All Access" magazine; managed the design and production process 
•	Served as producer and interviewer for video production featuring artists 
•	Led and motivated video production editors

Public Relations & Marketing Coordinator

American Cancer Society

As an Editor at Gannett, I had daily contact with public relations professionals for the first time, and I started to sense that a PR role was more in line with my goals and visions. So I relocated to New Orleans as the Communications & Marketing Specialist for the American Cancer Society, one of the largest nonprofits in the world. 

In this role, I quickly thrived, landing a cover story in the Living Section within my first few months, and earning Shining Star awards on a regular basis. I loved the branding and storytelling component of this role more than anything and enjoyed making connections with media outlets to increase the reach and influence of the American Cancer Society. In this role, I...

•	Implemented branding guidelines; Protected and enhanced the    
        image of the Society
•	Secured media hits and sponsorships; Wrote news releases, 
        alerts and newsletter stories
•	Trained volunteers in the Society’s mission and media relations

But perhaps the most momentous part of my career with ACS was the opening of the Hope Lodge, the first building to be resurrected after Hurricane Katrina. This campaign was about more than the opening of a building - it was a sign of progress and of hope for a city that was brought to its knees.

And personally, it allowed me the chance to secure national media coverage during my first year as a PR specialist. Unfortunately, the devastation of the city around me did take a toll, and after the Hope Lodge campaign came to a successful end, I started setting my sights on a city that wasn't quite so crippled and unsafe. Nashville was next!

Communications & Marketing Specialist

Gannett

With a prized Journalism degree under my belt, I was thrilled to land a job with Gannett, the largest newspaper publisher in the U.S. Not only that, but I secured the role of Editor for a weekly paper that covered the Gulf Coast: Perdido Key, Orange Beach, and Gulf Shores. Talk about a dream gig! 

And it truly was. I excitedly ramped up the branding and influence of the publication and brought some flair to the cover stories, adding in topics like "Inside the Gulf Coast's Largest Yachts" and "Where Do These Tigers Come From?" 

My goal was to increase circulation by appealing to both tourists and locals alike, and I did that through creative cover stories, elevated imagery, and exciting advertising designs. I worked closely with the sales team to maximize the earnings potential of the magazine in a way that aligned naturally with the editorial direction without compromising the integrity of the publication. 

We never fell below an 80-page publication during my duration, and at times crept up into 120+ pages due to increased advertising sales.

As Editor of a weekly publication, I wore the hat of:
•	Writer 
•	Creative Director of Ad Design Team
•	Photographer 
•	Manager of freelance staff of writers and photographers

Editor, The Pelican

👋 Hi, I’m Tiffany — keynote speaker, business consultant, and advisor for high-performing teams and founders.

After two decades leading global PR campaigns, running my own creative agency, and supporting powerhouse women scaling six- and seven-figure service businesses, I’ve learned this:

Success without sustainability isn’t success at all.

That’s why I help organizations build resilient teams that thrive — not burn out — and help founders grow wildly profitable businesses without losing themselves along the way.

🎤 Signature Keynotes:

✨ Help Is Not a Four-Letter Word
This keynote busts the myth that self-sufficiency is the ultimate strength. I show high achievers how asking for support creates better outcomes — for themselves, their teams, and their bottom line.

✨ Resilient Is Your Middle Name
A motivational and practical talk for today’s organizations who want to rise from setbacks, navigate uncertainty with confidence, and lead with heart — even in the hardest seasons.

💼 Consulting & Team Training
I partner with companies and fast-growth startups to help their teams:

- Lead without burning out
- Communicate and collaborate more effectively
- Build systems that support productivity and purpose
- Evolve leadership strategies for the modern workplace

🚀 Advising Female Founders
I coach agency owners, consultants, and creatives who are ready to:

- Stop doing everything alone
- Clarify their offers and raise their prices
- Build smarter systems
- Step into their CEO energy

🏆 My background includes leading PR for legends like Elton John, Alicia Keys, and Josh Groban, launching global campaigns with Yamaha and Live Nation, and running a boutique agency that brought brands to life across PR, branding, social, and creative direction.

Today, I use that experience to help modern leaders build businesses and teams that don’t break them.

Let’s connect if you’re:

- Booking an unforgettable speaker for your conference or retreat
- A founder who wants to scale with more clarity and confidence
- A people-first organization that believes leadership can be both powerful and compassionate

🌍 Based in Nashville. Speaking and consulting worldwide.
💌 www.tiffanynapper.com

Tiffany Napper

I’m fresh off hosting our first Yacht Club On-Shore retreat in Tampa. And the comment I heard most?

“I noticed your attention to detail.”

Not the waterfront views. Not even the incredible food, and there was a lot of it.
The details.

I learned that instinct early — from my mom, my grandmother, and my mamaw.
Then it was sharpened in rooms where excellence wasn’t optional: the music industry, celebrity talent, global brands with standards that left no room for “good enough.”

And yes… my Type-A wiring plays its part.

But here’s what this weekend reminded me: Details are how you make someone feel seen.

It’s remembering who prefers oat milk without asking.
It's hand selecting the pair of sunglasses for their swag bag that you think they will love the most.
It’s an amber candle glowing beside fresh tulips in the entryway next to a sign with their name on it.
It’s a surprise private shopping experience tucked into the afternoon agenda.

On paper, those things are small.

In memory, they’re everything.

Because when a woman feels deeply considered, the retreat stops being “an event.”

It becomes a moment she carries with her.

That’s the standard inside Yacht Club.

If you’re a founder who values rooms where the details match the ambition — you’d fit right in.

And if you’re a brand who believes experiences should feel intentional, elevated, and unforgettable — we should talk.

Proximity isn’t a perk these days. It’s the whole point. 

Picture from Day 1 just before our Fresh & Focused lunch provided by NexusPoint. (Channeling my inner Martha Stewart.)

Keynote Speaker & Business Consultant for Female Founders | Building Resilient Leaders, Profitable Teams & Joy-Driven Companies | Founder, Yacht Club

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Tiffany Napper

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The Battle

Christopher Clepp

Tiffany Napper

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