What happens when you realize you are not built to follow someone else’s blueprint?

In this episode of Yes And Land with Ryan Gregerson, Ryan welcomes entrepreneur Ryan Brown for an honest conversation about rejecting traditional career paths and building something aligned with purpose. After graduating early from the University of Utah with a marketing degree, Ryan faced major corporate opportunities. Instead of stepping into a conventional role, he chose entrepreneurship.

From medical billing to launching a fractional business management model for physicians, Ryan Brown shares how he built a service-driven business that supports medical practices without becoming just another employee.

This episode explores entrepreneurship, leadership, career pivots, risk tolerance, and how to design your professional life around your values.

If you are considering starting a business, shifting careers, or redefining success, this conversation will resonate.

🎯 Actionable Items

• Conduct a personal “wiring audit.” Are you a builder or operator?
• Identify skills you can monetize independently.
• Explore fractional consulting opportunities in your industry.
• Define what success means beyond salary or title.
• Say “Yes” to your current reality. Add “And” to what’s possible next.

00:00 – Why Corporate Wasn’t the Dream

03:12 – Graduating Early & Corporate Offers

06:45 – “I’m Not Built to Be an Employee”

10:18 – Turning Down Big Brand Opportunities

14:22 – Entering the Medical Billing World

18:10 – The Birth of a Fractional Business Model

23:40 – Serving Physicians as a Strategic Partner

29:05 – Entrepreneurship vs. Employment Mindset

34:12 – Designing Life Around Family & Values

39:30 – What Success Really Means

43:15 – Actionable Advice for Career Pivots

47:00 – Say Yes. And Land.

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Say yes to your current reality. And land in your next chapter.

What if the biggest thing holding you back online isn’t your skill — but your need to look perfect?

In this episode of Yes And Land, Ryan Gregerson sits down with Jana Oman to explore authenticity, personal branding, and the pressure to show up polished in a world obsessed with highlight reels. Jana shares her journey from learning to code in the early MS-DOS era at just eight years old to carving out a unique identity in real estate by embracing who she truly is.

Through the lens of Disney’s Encanto, they unpack the emotional weight of expectations, imposter syndrome, and the freedom that comes when you stop performing and start being yourself.

If you’ve struggled with confidence, overthinking your content, or wondering whether you’re “enough” to show up online, this conversation is for you.

Actionable Takeaways

• Audit where you’re performing instead of connecting.
• Rewrite your bio to reflect who you actually are.
• Share one honest, imperfect story this week.
• Stop copying industry templates and experiment with your voice.
• Choose clarity and alignment over polish and perfection.

Authenticity isn’t a branding tactic. It’s your advantage.

CHAPTERS

00:00 – Why Showing Up Online Feels So Hard

01:00 – Introducing Jana Oman

02:00 – Coding at Age Eight (MS-DOS Era!)

03:00 – Discovering College Was Possible

05:30 – The Pressure to Perform Online

10:00 – Lessons from Encanto

15:45 – Authentic Personal Branding

22:00 – Letting Go of Perfection

28:00 – Your Flaws Are Not Disqualifiers

34:00 – What Real Breakthrough Looks Like

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Your breakthrough may start with letting go of perfection.

🎙️ Yes And Land — Podcast Show Notes

Host: Ryan Gregerson Guest: Kenton Walker Episode Theme: Mentorship, growth mindset, and leading with experience

🌱 Episode Overview

In this thoughtful and wide-ranging episode of Yes And Land, Ryan Gregerson sits down with attorney Kenton Walker to explore the true meaning of mentorship—and why it matters more than ever in fast-paced, high-pressure professional environments.

Kenton shares his unconventional career journey, from pharmacist to patent litigator to family law attorney, and reflects on how each chapter shaped his approach to people, leadership, and learning. At the heart of the conversation is a powerful idea: mentorship isn’t about having all the answers—it’s about sharing experience, building trust, and guiding others through uncertainty.

The discussion dives into how mentorship prevents burnout, strengthens workplace culture, and creates space for growth on both sides of the relationship. Kenton also opens up about learning through mistakes, mentoring without titles, and why being a “guide” often matters more than being an expert.

To round things out, the episode features a fun movie tie-in with The Intern, plus a rapid-fire “This or That” segment that gives listeners a glimpse into Kenton’s personality beyond the courtroom.

✨ Actionable Takeaways:

1. Put down distractions, and observe
2. Look for opportunities around you where someone is struggling or needs help
3. When you do, and the need for advice arises, use this line: “Here was my experience...”

🎬 Movie Tie-In

• The Intern (Robert De Niro) — mentorship across generations, humility, and shared wisdom

🎧 Listen & Subscribe

If you’re navigating leadership, career growth, or simply looking to be a better guide for the people around you, this episode offers practical insight and genuine inspiration.

👉 Subscribe to Yes And Land for more conversations about growth, mindset, and the next chapter ahead.