Chris Bogue Communications

Writer and video consultant living in Chicago. I make short, personalized video content that drives revenue for business owners. I also train sales, marketing, and customer success teams to add video prospecting to their existing processes.

Owner

Death by Powerpoint

An interactive improv-based live show where competitors must do battle by presenting a Powerpoint presentation they have never seen before.

Host

Sendspark

Simplifying the short video creation process for B2B sellers.

Strategic Advisor

Chris Sells His Soul

Chris Sells His Soul is a show about monetizing creativity. Join Chris Bogue and guests for thoughtful conversations about how to benefit from your talents.

RevPartners

Launched the Rev Partners content creator cohort. I coached 12 creators and helped them develop original content series to promote their personal brands and create new pipeline and audience growth. Somehow made Robert Jones 10 times funnier.

Creative Advisor

Packback

Owning the sales process from prospect, to cold call, to demo, to deal construction, to close, to renewal. Collaborating with the nation's top universities for educational consultation for remote learning.

Experienced Strategy Consultant at Packback

Belly

Focused on relationship management, account growth, feature adoption, upsells, and referrals. Specialized in high-risk accounts whose cases were escalated based on likelihood to cancel.

Customer Development Manager

XPO Logistics, Inc.

Account Manager

Groupon

Inside Sales, prospecting and consulting with over 100 different businesses helping them acquire tens of thousands of new customers, negotiating contracts, using Twitter, Yelp, and other social media to identify new and creative businesses to be featured on the website

Account Representative

Paige Personnel Services

Setting up fundraisers, building relationships with new clients, and coordinating with independent sales representatives in all 50 states

Inside Sales

Writer and video coach specializing in sales and sketch comedy. I help people sound natural and play to the top of their intelligence on camera.

I coach an improv-based approach to content creation and sales. It's all about being direct, supportive, and fun!

Chris Bogue

Suck at something this weekend

Most people are scared of doing things they are not good at. That's why I always think about Eleanor Roosevelt's advice to do one thing every day that scares you


🎷🎅🏻 This weekend I will be practicing Christmas tunes so I don't suck at the family Christmas party this year

I'm still bad. But every day I get a little better.


There's so much pressure in this world to be perfect. I support people loving what they do even if they suck at it and never plan to make money off of it.

Dare to suck. Have a great weekend, everybody

Coaching sales and building processes that break patterns and drive revenue 🎬

Holy crap Gemini. I am officially impressed.

I uploaded a 30 minute audio file of me practicing saxophone


You all know I'm not easy to impress when it comes to AI, but I was shocked by the feedback

✅ It ranked the songs by how well I played
🎼 Identified specific moments where tuning was an issue
🎷 Even analyzed my tone and gave me notes on what to do with my jaw to get a more velvety sound


If you create audio or video content, try uploading a file straight to Gemini and asking it for feedback

PS I'm also taking requests for Christmas sax jams so drop em if you got em

Text: Google Gemini suddenly became a good saxophone teacher

Image: Chris Bogue playing a saxophone looking up at the text

My hot take? AI hasn't changed sales very much 🤷‍♂️

Sure there's been lots of layoffs and hype for automation, but how has it actually changed the buying and selling experience?


Buyers
❌ Still don't trust salespeople
❌ Still can't get a straight answer without taking a meeting

Sellers
❌ Still have to do research because AI is unreliable
❌ Still have to work their asses off to build and maintain relationships because buyers hate being on the receiving end of automation


Sales is frustrating. Always has been. Always will be.

IMO learning the boring fundamentals and working your ass off is and will always be a safer bet than learning AI

Building Towards Wealth

Helping Gen X & Gen Y Business Owners Make Smart Financial Decisions

President

Strategic Financial Group

Chicago-based wealth management practice providing financial planning to business owners.

Financial Planner & Wealth Advisor

Christopher Clepp Financial Solutions

Providing financial solutions to the Chicagoland area. We specialize in two areas.
1)Helping small business owners plan for the protection and growth of their business. 

2)Helping high-income earners, above find unique ways to protect and grow their income for retirement.

ASUREA

Area Manager, representing 60 Life, Disability, Mortgage Protection, Annuity and LTC carriers

Chicago Area Manager

Integrated Financial and Insurance Strategies

Opened and developed 4 insurance offices across the country

Specialized in insurance solutions for high-income earners and business owners.

Partner and Business Insurance Specialist

Promark Financial

Sales Manager

Marriott

Phone sales for their Vacation Club division

Team Leader

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

Sometimes you get involved with an organization and with people who truly make you feel fortunate.

I’m lucky enough to lead what I believe is the best networking group anywhere. And yes, I’ll stand by that.

This past Thursday, our Trusted Advisors Council OG Downtown group got together to celebrate the holidays at Big Mini Putt in Wicker Park. It was a great reminder of why this group works so well. The professionals in this room are incredibly smart, generous with their time, and always willing to jump in when a client has a challenge. Just as important, they’re the kind of people who help you grow your business while also feeling more like friends than “contacts.”

I couldn’t be prouder of the group of professionals I get to work with and help lead. Grateful for the relationships, the collaboration, and the trust we’ve built together.

Here’s to strong partnerships, real friendships, and continued growth in the year ahead.

Rakesh Parikh Craig Achtzehn Mark Brodson Andrew Balderson Natasha Hansen Steve Cevaal Leslie Lipin Paul Sippil Sheila Devi James Muraff Erich Buck Ryan Strohmeier Jim Spencer, CFE, CVA, CIRA, CCA Spencer Keith Glantz Joel Berman Joel Bennett, SHRM-SCP Bennett Ken Scales

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

No alternative text description for this image

Financial planning has a branding problem.

It’s been boxed into “retirement.”

But the real purpose is far more practical: it’s a roadmap to autonomy.

Autonomy means having the flexibility to walk away from a job that no longer serves you, pivot when your industry evolves, or say yes to opportunities without wondering whether the numbers will break your life.

If you’re a high earner who thinks planning doesn’t apply to you because retirement feels distant, ask yourself:

How stable is your field in the coming AI wave?

And if the landscape shifts, are you prepared—or exposed?

Planning isn’t about ending your career. It’s about protecting your ability to shape it.

Happy Thanksgiving from my family to yours!

I love my career. 

Like most business owners, it’s a lot of work, but it’s also a labor of love. 

What truly excites me is how I’ve built my life around this mindset. I’ve structured my priorities so that when my kids are sick or have a school event, I'm there for them.

That’s what it’s all about, controlling my time so I can be there when it matters most. 

We are always trading money for time and time for money. 

For me, having the freedom to prioritize my family is the real win. 

The business should serve that purpose, not the other way around. 

It’s easy to forget that and let the work take over. 

Remember who you’re working for, and why. 

Your time and your family are worth it. 

Make your business work for you, not the other way around. 

What’s one way you’ve prioritized what truly matters lately?

You might be surprised by what you can achieve when you focus on just one thing.

When your attention is split across five, seven, or even ten tasks, progress stalls, and frustration sets in.

The truth is, nobody performs at their best when stretched in too many directions.

That’s why outsourcing your financial planning as a business owner isn’t just smart, it’s essential.

It frees you up to do what truly matters: building your business, being a better parent, and being the spouse you want to be.

Don’t try to do everything alone. Delegate the parts that don’t need your expertise.

Invest in your focus, your time, and your peace of mind.

Because when you simplify your financial strategy, everything else falls into place.

Are you ready to focus on what really matters?

Let’s talk about how outsourcing can change the game for you.

A lot of high earners dismiss financial planning because they’re not thinking about retirement yet.

Here’s the truth:
Financial planning isn’t about retirement.

It’s about autonomy—having the ability to choose your next step without being handcuffed to your paycheck.

And with AI transforming industries faster than most people realize, autonomy matters more than ever. Even strong careers are facing uncertainty, and the professionals with a plan will be the ones who stay in control.

You don’t plan because things will go wrong.

You plan so that if the path changes, you’re not caught off guard.

If you value control, clarity, and optionality, you’re the exact person financial planning is built for.

Retirement is a milestone.
Autonomy is a strategy.
That’s the distinction most people miss.
Financial planning is the process of building enough stability, flexibility, and liquidity so you can make decisions based on what’s right—not what pays the bills fastest.
For high earners who feel “too early” to think about planning, here’s the challenge:
Your career may be strong, but is it insulated from the coming AI disruption?
And if something shifts, do you have the runway to pivot?
Planning gives you that margin.
It gives you control.
It gives you freedom years before retirement ever enters the picture.
Autonomy is the outcome worth aiming for.

My friend Kimberly Wasney makes a great point

Most owners also think about their exit the way they think about their personal finances as something they’ll “get to later.” The truth is that both sides compound. Operational improvements build enterprise value, and coordinated financial planning determines how much of that value actually stays with you and your family.

I meet so many founders who pour everything into improving the multiple, but haven’t aligned their personal balance sheet, tax strategy, or post-exit plan. The result is unnecessary leakage at the moment when they should be capturing the benefits of all the years they invested in the business.

When you combine what she is describing, intentional operational decisions. with a long runway of personal planning around taxes, liquidity, retirement, and risk, you’re not just creating a higher valuation. You’re keeping a larger amount. And that’s ultimately what drives freedom, options, and long-term security.

A better exit starts long before an LOI. And for owners who want real control over their future, there’s nothing more powerful than coordinating both tracks early.

Exit isn’t an event.

It’s a series of decisions that build on each other over time. Just like investing your money in the market, that compound effect is massive. 

For example, say your business is currently running at a $3M EBITDA in an industry where multiples range from 4-6x. 

4 to 6 doesn't sound like that big of a difference, but when we do the math, we're talking $12M vs $18M. Now we're talking real money that matters to your family, your lifestyle, your future. 

The earlier we work together, the more aligned your pathway becomes — your values, your leadership, your team, your numbers. That alignment shows up in your valuation and in your options.

Early preparation is a gift to your future self. And $6M is pretty good gift!

Most people hear “financial planning” and immediately jump to “retirement planning.”
 
But retirement is only one version of the real goal: autonomy.
It’s about having control over your decisions so your career, your family, and your life aren’t dictated solely by money.
 
If you’re a high earner who says, “Financial planning isn’t for me—I’m nowhere near retiring,” it’s worth asking a different question:
 
Do I want to be able to make decisions without fear?
 
We’re heading into an era where AI is reshaping entire industries. Even talented, high-earning professionals may see their roles shift faster than expected.
 
Having a plan isn’t about predicting the future. It’s about preparing for a future that might look different from the one you assumed—and keeping your options open if the path changes.
 
Autonomy > retirement. Always.

Wealth isn’t built overnight.

 It comes from consistent, intentional financial decisions over time. 

Understanding how different strategies work together—such as savings, investments, and risk management—can help create a strong foundation for long-term success. 

Every step forward, no matter how small, contributes to financial security. 🏗️📈

#financialplanning #businessowner #buildingwealth #financialplanner #wealth #smallbusiness #genx #geny #buildingtowardswealth #henrys #abundantwealthprocess #stability #financialfulfillment #highearner #strategicfinancialplanning

building-towards-wealth

li_at

JSESSIONID

Talks about #business, #investing, #financialadvice, #financialadvisor, and #financialplanning

Most Gen X and Gen Y business owners feel pressure to hit home runs, the big tax win, the perfect investment, the major financial unlock.

I know the feeling. I spent far too much of my 20s and 30s chasing the game-changing moment.

But 2025, the year I turned 50 and my best year personally and professionally, taught me a lesson I wish I embraced earlier. Real progress comes from consistent 1 percent improvements, not dramatic leaps.

For business owners, that looks like:
• refining your tax plan every year so the IRS takes less
• upgrading your retirement structure as profits grow
• protecting your family and business as responsibilities rise
• aligning investments with the unpredictable rhythm of ownership
• coordinating with your CPA and attorney so you do not carry every decision alone

These are small steps that do not feel life-changing day to day, but they are exactly what create long-term autonomy.

If you want help identifying where your 1 percent improvements are hiding, I am always happy to map that out.

taplio

The Battle

Chris Bogue

Christopher Clepp

Followers

Posts

Engagements

Likes

Performance ScoreChris Bogue's LinkedIn Performance

Performance ScoreChristopher Clepp's LinkedIn Performance

Ready to grow your LinkedIn presence?

taplio

The Battle

Chris Bogue

Christopher Clepp

Followers

Posts

Engagements

Likes

Performance Score.css-goub6s{font-size:var(--chakra-fontSizes-md);font-weight:500;color:var(--chakra-colors-gray-600);display:block;margin-top:var(--chakra-space-1);}Chris Bogue's LinkedIn Performance

Performance ScoreChristopher Clepp's LinkedIn Performance

Ready to grow your LinkedIn presence?

Performance ScoreChris Bogue's LinkedIn Performance