Making Cents of It All

In this episode of Making Cents of It All, Jesse Stakes sits down with Henok Kebede, CPA, the CEO and Founder of HK Advisory LLC, to break down what it really means for a CPA to be a true advisor to business owners. Henok shares how entrepreneurs can move beyond simple tax preparation and into proactive planning that reduces tax burden, strengthens operations, and builds long‑term financial health.

From entity structure decisions to year‑round tax strategy, Henok explains the practical steps business owners can take to run smarter, more efficient companies. He also dives into the mindset shift required to treat your CPA as a strategic partner — not just someone you see once a year.

Whether you’re a business owner, an emerging entrepreneur, or someone looking to better understand how advisory‑driven accounting can transform a company, this conversation delivers clarity, actionable insights, and a fresh perspective on financial leadership.

Topics we cover:

• The difference between tax preparation and true advisory
• How business owners unintentionally increase their tax burden
• Year‑round strategies to reduce taxes and improve cash flow
• Why entity structure matters more than most people think
• The role of clean books in better decision‑making
• How CPAs can help owners think like CEOs
• Real examples of advisory work that changed businesses

Tune in and learn how to make your numbers work for you — not against you.

In this episode of Making Cents of It All, Jesse Stakes sits down with Caleb Garrett, Director of Development for the Coggin College of Business at the University of North Florida. Caleb brings a dynamic blend of relationship‑building, strategic fundraising, and a deep commitment to student success — all of which fuel the mission of one of the region’s most influential business schools.

Jesse and Caleb dive into the real story behind university development: how meaningful partnerships are built, why philanthropy shapes the future of business education, and what it takes to connect donors, alumni, and community leaders with opportunities that create lasting impact. Caleb shares insights on cultivating trust, elevating student experiences, and strengthening the bridge between Jacksonville’s business community and UNF’s next generation of talent.

Whether you’re an alum, a business leader, or someone who cares about the future of education, this conversation offers a thoughtful look at how development work drives growth, innovation, and opportunity across Northeast Florida.

A smart, inspiring, and human conversation — exactly what Making Cents of It All is all about.

In this special major‑week episode of Making Cents of It All, Jesse Stakes sits down with The Tin Cup Club to break down the year’s final major — the 2026 Open Championship at Royal Birkdale. From the history of this iconic links to the economic engine behind golf’s oldest championship, the crew dives into everything that makes The Open unlike any other event in the sport.

Royal Birkdale has long been known as one of the fairest, toughest, and most visually stunning courses on the Open rota — a place where the dunes shape the story, the wind decides the champion, and only the most complete players survive. With record crowds expected and a projected economic impact topping £100 million, the 2026 Open is set to be one of the most influential sporting events of the year.

Jesse and The Tin Cup Club dig into:

• What makes Royal Birkdale the perfect stage for the final major
• The unique challenge of links golf and how players adapt
• The contenders, dark horses, and storylines shaping the 2026 championship
• How The Open drives massive economic growth for Southport and the Liverpool City Region
• The fan experience, the culture, and the legacy that only The Open can deliver

Whether you’re a golf fan, a business mind, or someone who loves the intersection of sport and strategy, this episode brings insight, personality, and plenty of major‑week energy.

Tune in as we make cents of the final major — and why Royal Birkdale is ready to crown a champion.

In this episode of Making Cents of It All, Jesse Stakes sits down with Drew Webb — CEO, founder, and the creative force behind Affari, a marketing and digital innovation agency helping brands grow through strategy, design, and AI‑driven transformation.

Affari has spent more than a decade building the future for its clients — from branding and visual identity to custom websites, digital marketing, and AI‑powered search optimization. Drew breaks down how Affari helps companies tell their story, stand out in crowded markets, and stay visible in an era where AI is reshaping how people discover and engage with brands.

Jesse and Drew explore:

• How Affari blends creativity, technology, and strategy to build cohesive brand experiences
• Why AI‑driven search optimization is becoming essential for modern businesses
• The process of transforming complex ideas into clear, compelling design
• How Affari’s team of designers, strategists, marketers, and technologists collaborate to bring a client’s vision to life
• What it takes to build a creative agency that has been “creating the future since 2011”

Drew shares the real founder story — the early days, the evolution of Affari’s capabilities, and the mindset required to lead a team that helps clients envision a better future and actually build it.

If you’re a business leader, marketer, entrepreneur, or someone fascinated by the intersection of creativity and technology, this conversation delivers insight into how brands grow, adapt, and thrive in a digital-first world.

Tune in and make cents of it all.

This week on Making Cents of It All with Jesse Stakes, the Tin Cup Club joins me to break down one of the biggest economic engines in sports — the U.S. Open.

We dig into:
• How the USGA generates millions through TV rights, sponsorships, and hospitality
• The real economic impact on host cities — jobs, tourism, infrastructure, and local business
• What volunteers actually receive (and why they still line up to help)
• Course setup, fan experience innovations, and the storylines shaping 2026

It’s golf, business, community, and strategy all in one conversation.
If you love the game — or the economics behind major events — this one’s for you.

In this episode of Making Cents of It All, Jesse sits down with Meshia and Aniekan Sampson, the husband‑and‑wife team behind Back 9 Golf Lakewood, one of Jacksonville’s newest and most exciting indoor golf destinations.

The Sampsons share the story behind their decision to step into entrepreneurship, what inspired them to take the leap into business ownership, and how Back 9’s unique franchise model opened the door for them to build something of their own in the Lakewood community.

From their first conversations about owning a business to the moment they realized Back 9 was the perfect fit, Meshia and Aniekan talk candidly about the challenges, the learning curve, and the joy that comes with creating a space where people can play, practice, and connect. And of course, they dive into their love of the game — how golf became a shared passion, why it brings people together, and what they hope Back 9 Lakewood will mean for golfers of all skill levels across Jacksonville.

Whether you’re a golfer, an entrepreneur, or someone who loves a good origin story, this episode is packed with insight, inspiration, and heart.

Jesse and the Tin Cup Club are diving into one of the biggest sporting and economic stories heading toward the East Coast in 2026: the PGA Championship at Aronimink Golf Club in Newtown Square, Pennsylvania.

This isn’t just another major. This is a week that’s expected to bring more than two hundred thousand visitors into Delaware County and pump an estimated one hundred and twenty‑five million dollars into the local economy. Hotels are already booking out, restaurants are gearing up for record traffic, and small businesses across the region are preparing for what could be the most impactful week they’ve ever seen.

Aronimink itself is a historic venue — a Donald Ross masterpiece that’s hosted everything from the AT&T National to the BMW Championship to the KPMG Women’s PGA. And now, for the first time since 1962, it’s back on the global stage for the PGA Championship.

Today, we’re going to break down what makes this course such a demanding test, why the economic impact is so massive, and what fans, businesses, and players can expect when the world of golf descends on Newtown Square.

Making Cents of It All with Jesse Stakes welcomes Jeffrey Condren, CFP®, Senior Vice President at Mesirow Wealth Advisors, for a powerful, insight‑packed conversation on one of the most misunderstood financial milestones a business owner will ever face: the exit.

Drawing from years of advising founders, entrepreneurs, and multi‑generation business owners, Jeffrey breaks down the real drivers of a successful sale — the operational, financial, emotional, and personal factors that determine whether an exit becomes a wealth‑building event or a missed opportunity.

🔍 What We Cover in This Episode

1. Setting the Stage: When Owners Should Start Thinking About an Exit

Jeffrey explains the earliest signals that it’s time to prepare, the mindset shifts that separate successful sellers from those who struggle, and why the emotional side of letting go often catches founders off guard. 

2. Preparing the Business for Sale

We dig into the operational and financial blind spots owners commonly discover, the ideal preparation timeline, and the metrics buyers scrutinize most. Jeffrey also highlights why leadership succession planning is one of the most underrated value drivers. 

3. Building the Right Advisory Team

Jeffrey outlines the essential advisors every owner needs, the risks of relying solely on internal teams, and how a strong advisory bench protects value during negotiations. 

4. Understanding Valuation & Deal Structure

We unpack the biggest misconceptions around valuation, how to think beyond the headline number, and the long‑term impact of earn‑outs, rollover equity, and seller financing. 

5. The Wealth Event: Preparing for Life After the Sale

Jeffrey shares how he helps clients prepare for the sudden shift in wealth, avoid common post‑liquidity mistakes, and build a long‑term plan that integrates tax strategy, investments, and stewardship. 

6. Emotional & Personal Transitions

We explore the identity challenges founders face once the business is no longer theirs, how to prepare family members for the impact of a liquidity event, and what a healthy transition truly looks like. 

7. Lessons Learned & Real‑World Stories

Jeffrey shares examples of owners who prepared exceptionally well — and those who didn’t — and the lessons every business owner can apply today. 

Rapid‑Fire Takeaways

• Biggest value‑killer
• Most underrated value‑driver
• One thing owners should stop doing
• One thing they should start doing
• The question owners never ask but should 

This episode is a must‑listen for any founder, entrepreneur, or family‑owned business preparing for the next chapter.

What happens when the world of golf collides with the thrill of collecting? In this episode of Making Cents of It All, Jesse Stakes sits down with Brandon Fischer, the visionary CEO and Founder of RareShot Golf, to explore how he’s bringing the Pokémon‑style chase to one of the most traditional sports on the planet.

RareShot Golf isn’t just another golf brand — it’s a full‑blown collectible ecosystem built around performance‑grade golf balls designed with rarity tiers, limited drops, and the kind of “pull excitement” usually reserved for trading cards and sneaker culture. Brandon breaks down how he took inspiration from the Pokémon craze, modern collectibles, and the psychology of the chase to create product golfers don’t just play… they hunt.

We dive into:
• The origin story behind RareShot Golf
• How rarity tiers (Common, Uncommon, Rare, and beyond) are reshaping golf culture
• Why golfers are embracing the collectible mindset
• The balance between high‑performance equipment and artistic design
• What the future of golf collectibles looks like — and why this is only the beginning

Whether you’re a golfer, a collector, an entrepreneur, or someone fascinated by how new markets are created, this episode shows how Brandon is turning a simple golf ball into a cultural moment.

RareShot Golf isn’t just innovating — it’s igniting a movement.

The Masters isn’t just a golf tournament — it’s a masterclass in branding, scarcity economics, and operational excellence. In this episode of Making Cents of It All, Jesse Stakes sits down with the Tin Cup Club to break down why Augusta National continues to set the gold standard for sports events worldwide.

We dig into the 2026 Masters storylines, including Tiger Woods’ latest challenges and what his future means for the sport. From there, we explore how the Masters has built one of the most powerful brands in sports through intentional scarcity, disciplined tradition, and a fan experience that feels almost immune to modern commercial pressures.

The Tin Cup Club also unpacks the behind‑the‑scenes innovation that most fans never see — from Augusta’s cutting‑edge broadcast technology to the operational precision that keeps the course pristine and the coverage flawless. Whether you’re a golfer, a business leader, or someone who appreciates world‑class execution, this episode shows why the Masters remains the ultimate case study in doing things differently — and doing them exceptionally well.