Hannah Howard is a former Division I athlete and Power Five head coach who has made the leap from elite college athletics into tech leadership as the CEO of Rematch U.S.

In this episode of How to Ride a Roller Coaster, Hannah shares her journey from the court to the boardroom, including what it means to lose your first professional dream, how coaching is really running a business, and why leadership requires stepping into uncertainty long before clarity shows up.

We dive deep into:

• The transition from athlete and coach to CEO

• How sports leadership translates to business leadership

• Why youth sports visibility matters beyond recruiting

• How Rematch uses AI to capture meaningful moments in real time

• The fragmented nature of the U.S. youth sports market

• Building teams through vision, trust, and transformation

This conversation goes beyond technology and tactics. It’s about identity, belief, and what happens when you’re willing to enter the arena, even when the outcome isn’t guaranteed.

🎧 Whether you’re an entrepreneur, a former athlete, a parent in youth sports, or a leader navigating your next chapter, this episode is for you.

Show links:

Hannah on LinkedIn

Rematch

Greatness book

Selling online feels simple... until taxes quietly start working against you.

In this episode of How to Ride a Roller Coaster, host David Ezell sits down with Jared Smithson, Founder of RJM Tax Exemption and one of the leading experts in U.S. e-commerce tax compliance. Jared has helped over 5,000 businesses navigate sales tax, multi-state nexus, and regulatory landmines that most founders don’t realize they’ve stepped on until it’s too late.

You’ll learn:

• The most common sales tax mistakes e-commerce founders make (including the “one-click” Shopify error)

• Why revenue growth can be fake growth if compliance isn’t handled correctly

• How economic nexus actually works (and why $100K isn’t the only number that matters)

• Why collected sales tax isn’t “your money”—and how it can block an exit

• What’s changing next for digital products and services taxation

• When to DIY vs. when to bring in experts (without wasting money)

Whether you’re selling on Shopify, Amazon, Walmart, or planning to expand into the U.S. market, this conversation could save you six figures, months of stress, and a painful audit.

Show links:

RJM Tax Exemption: https://rjmtaxexemption.com/

Jared: https://www.linkedin.com/in/jared-smithson-692607228/

Finance isn’t just numbers. It’s identity, access, and peace of mind. Yet so many women, millennials, Gen-Z professionals, and underserved investors feel invisible in the world of wealth management. Today’s episode shines a spotlight on changing that.

I’m joined by Lacy Garcia, CEO and Cofounder of Willow, a fintech platform that matches individuals with fiduciary financial advisors who actually get them. Lacy left a stable career, survived the chaos of launching during COVID, and built a platform dedicated to empathy, education, and empowerment in financial planning.

We dig into:

• The shame-free truth about financial literacy (even highly educated people don’t know this stuff!)

• How to find an advisor who understands YOUR values, goals, and identity

• Why separating your personal and business finances is non-negotiable as a founder

• How to protect your energy and avoid burning yourself out while building something meaningful

• The hard lesson of focusing on revenue and efficiency first, not perfection

Whether you’re growing a business, building wealth, or just trying to make smarter financial decisions, this episode will save you time, money, and serious stress.

Show links:

Willow: https://trustwillow.com
Lacy on LinkedIn: https://www.linkedin.com/in/lacygarcia
Willow on Instagram: https://instagram.com/trustwillow

Today's episode is sponsored by Clutch City, a bold, high-impact experience for entrepreneurs scaling real businesses between $250K and $3M.

Clutch City: https://www.clutchcityhq.com

IG: https://instagram.com/clutchcityhq
More at: https://realdavidezell.com/clutchcity

If you loved today’s episode, share it with a founder who needs clarity on money or is tackling their next big leap. One episode can change someone’s week.