Building Brands That Win: Drew Webb on the Affari Approach to Creative Strategy

Building Brands That Win: Drew Webb on the Affari Approach to Creative Strategy

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.

The Business Behind the 2026 U.S. Open

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.

Inside Back 9 Golf Lakewood: Meshia & Aniekan Sampson on Entrepreneurship, Franchising, and the Love of Golf

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.

From Philly to the Fairways: The Stories Behind the 2026 PGA Championship

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.

The Exit - The Ultimate Guide to Exit Planning: Deal Structure, Valuation & Life After the Sale

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.