Sam Green went from athlete to ESPN storyteller to founder of AthleteCon and she's here to share what actually drives NIL success. In this episode, she breaks down social media strategy, the power of storytelling, and what separates athletes who land deals from those who don't. If you're an athlete or a parent trying to figure out where to start, this one's for you.

About Sam:
Sam Green is the founder of AthleteCon and a former athlete whose career took her from the dance floor to ESPN, where she honed her expertise in storytelling and athlete branding. She now works with student-athletes and families to build authentic, monetizable brands in the NIL era, helping athletes understand that their story is their greatest asset. Through AthleteCon, Sam facilitates NIL deals, provides branding strategy, and educates the next generation of athletes on how to show up with purpose both on and off the field.

Chapters
00:00 Introduction to Sam Green and AthleteCon
00:42 Sam Green's journey from dancer to athlete brand expert
01:58 Realization of being part of a larger brand during athletic career
02:59 The impact of deleting and rebuilding social media audiences
04:38 Advice for athletes facing social media burnout
06:16 Rebuilding social media presence and redefining personal brand
08:25 Lessons learned from ESPN on storytelling and athlete branding
10:14 The inception of AthleteCon and its mission
12:36 Memorable athlete deal stories and success examples
15:16 Funding AthleteCon and early challenges
16:35 Lessons learned from building AthleteCon
18:53 When should athletes and families start NIL planning
19:54 Common misconceptions about NIL among students and parents
23:00 Leveraging AI for athlete content and strategy
26:11 Future trends: What separates successful NIL athletes
27:51 Upcoming plans for AthleteCon and final thoughts

Connect with Sam Green
AthleteCon Official Website - https://athletecon.com

Sam Green Instagram - @sambgreen

Connect with Brian Davidson
Linkedin

Get Started with NIL

If you're navigating NIL or supporting a student-athlete, understanding branding and strategy early can make a major difference in long-term success. Make sure to get started for free at nilgameplan.com

The NIL era has changed everything, but not always in the ways athletes and families think. In this episode, Dr. John DeWitt breaks down the myths and realities of NIL deals, college recruitment, and the transfer portal. With only 7% of high school athletes historically making it to the college level and with that number shrinking, the stakes have never been higher. Dr. DeWitt shares what families get wrong about scholarships, how the transfer portal has raised the competition bar, and what athletes should actually be focused on to improve their shot at playing at the next level.

About John:
Dr. John DeWitt is a former SEC and professional football player turned advocate for student-athletes and their families. Drawing from his own experience in high-level competition, he works with high schools, athletic directors, coaches, and families to navigate the increasingly complex world of NIL, recruiting, the transfer portal, and athlete well-being. A YMHFA-certified mental health first aid advocate and author of The High School NIL Reality Guide, Dr. DeWitt helps today's athletes make informed decisions before they get locked into opportunities they don't fully understand, covering everything from eligibility and compliance to the emotional pressures of identity, social media, and performance culture.

Timestamps:

0:03 — Intro and John’s background

0:31 — Athlete background and rise to the pros

4:31 — Student-athlete education and what’s being missed in NIL

6:38 — Key differences between states on high school NIL

9:11 — What NIL opens up for student athletes and families

13:08 — Examples of local NIL deals like pizza and gyms

15:05 — Agents, lawyers, and contract mistakes

19:29 — Balancing student, sports, business, and NIL fit

22:32 — Why so many athletes, parents, and coaches are confused

24:19 — John’s work helping families understand NIL

Connect with Dr John DeWitt:
Linkedin

Connect with Brian Davidson
Linkedin

Get Started with NIL

If you're navigating NIL or supporting a student-athlete, understanding branding and strategy early can make a major difference in long-term success. Make sure to get started for free at nilgameplan.com

In this episode, Michael Flores, co-founder of Triad Sports, shares his personal journey through college athletics, the transfer portal, and the opportunities and pitfalls of Name, Image, and Likeness (NIL) deals. He breaks down the realities behind recruiting, agent involvement, and how student-athletes can take control of their future.

About Michael:
Michael Flores is a co-founder of Triad NIL and former college football offensive lineman whose career took him from the Ivy League at Dartmouth to Old Dominion, where he earned a Master's in Sports Management and started all 12 games at center, to his final season at Louisville, where he helped beat #2 Miami and won the Boca Raton Bowl. Along the way, he interned in commercial real estate, navigated the transfer portal firsthand, and watched the NIL landscape reshape college athletics in real time. That experience became the foundation for Triad NIL, which he co-founded to give student-athletes the contract literacy, agent guidance, and financial education he wished he'd had.

Timestamps:

00:00 - Guest introduction and Michael’s background in college sports
00:20 - The Ivy League recruitment process and academic priorities
01:00 - Financial aid and scholarship myths in Ivy League schools
02:00 - Transition from Dartmouth to Old Dominion and initial transfer considerations
03:30 - The impact of NIL on transfer decisions and athlete awareness
04:20 - How NIL started influencing college athlete decisions post-COVID
05:00 - The role of agents: from offers to high fees and self-managed strategies
06:45 - The founding of Triad Sports and motivation to help student-athletes
08:00 - Early NIL awareness and misconceptions about brand endorsements and pay-to-play
09:15 - The “free agency” era and agent influence on NIL deals
10:30 - Different agent fee structures and how families can evaluate them
11:50 - The common lack of understanding among athletes about contract details
13:00 - The importance of early planning and involvement in recruiting and NIL tactics
15:00 - How current athletes can stay proactive and build their network
16:30 - The significance of building trust with coaches and the small-world nature of college sports
17:45 - Selecting trustworthy agents and questions to ask before signing
19:00 - Mistakes athletes make regarding contract comprehension and ethical issues in the NIL space
20:45 - When to start thinking about NIL: high school versus college stages
22:00 - Tips for athletes and families to take control of their recruitment and NIL process
23:30 - How to evaluate agents: results, network, reputation, and fees
25:00 - The importance of understanding contract terms and avoiding exploitative practices
26:00 - Starting early: the ideal timeline for recruitment and NIL planning
28:00 - The key mentality: having a long-term game plan with education and mentorship
29:15 - Connecting with Michael for guidance and resources

Connect with Michael Flores:

Triad NIL Website

Connect with Brian Davidson
Linkedin

Get Started with NIL

If you're navigating NIL or supporting a student-athlete, understanding branding and strategy early can make a major difference in long-term success. Make sure to get started for free at nilgameplan.com

About Ayden Syal-
Ayden Syal is an industry-recognized sports technology entrepreneur and marketing innovator featured in Forbes, Sports Business Journal, Adweek, CNBC, ESPN, and Sportico, and is a frequent keynote and panel speaker across sports, media, and technology events. After graduating from Notre Dame and building experience at Morgan Stanley, Lexington Partners, and IHS Markit, he co-founded MOGL, a venture-backed sports-tech platform that automates mass-scale influencer marketing by connecting brands and fans with athlete influencers for sponsorships, endorsements, UGC content, and more, with integrated reporting, compliance monitoring, and payment facilitation. Trusted by major NCAA athletic departments, NIL collectives, NBC Sports, and Notre Dame Athletics, MOGL won the SXSW Pitch Competition, earned a Sports Business Journal Power Player recognition, and is backed by Magarac Venture Partners, PivotNorth Capital, and Penske Media Corporation.

Timestamps

00:00 The Birth of MOGL: Vision and Mission

02:08 Growth and Evolution of Mogul

05:47 Equal Access in the NIL Space

07:24 Understanding Value: Athletes and Brands

10:26 Amplifying Athlete Campaigns

12:23 The Future of NIL and Mogul

16:11 Education Gaps for Student Athletes

Connect
Aydan Syal on LinkedIn
MOGL

Brian Davidson on Linkedin

Get Started with NIL

If you're navigating NIL or supporting a student-athlete, understanding branding and strategy early can make a major difference in long-term success. Make sure to get started for free at nilgameplan.com

In this episode, we explore the evolving landscape of youth sports, NIL, and athlete representation with industry experts Chris Fair and Justin Brashear. They share insights on early talent identification, legal protections, the importance of education, and building a sustainable career in sports beyond the field.

About Chris-
Chris is a certified NFLPA Contract Advisor with a comprehensive background in business and law. He earned his undergraduate and MBA degrees from Bentley University before completing his law degree at Pace University School of Law. Chris passed the New York State Bar and brings legal expertise, strategic thinking, and contract knowledge directly into athlete representation.

About Justin-
Justin is a sports attorney and certified NFLPA Contract Advisor with firsthand experience as a former professional athlete. His background in both law and elite athletics allows him to guide athletes and their families through critical decisions involving contracts, NIL opportunities, and career strategy.

Timestamps

00:00 Introduction to Trajectory Sports and Founders' Backgrounds

12:25 Navigating NIL and Recruiting Process

24:37 The Role of Family in Athlete Representation

28:19 Insurance and Financial Protections for Athletes

30:05 Understanding Contracts and Financial Structures

33:32 The Role of Social Media in Athlete Branding

37:35 Advice for Parents and Student Athletes

43:18 Opportunities Beyond Football in NIL

46:51 Building a Business Through NIL Gameplan

Trajectory Sports

Chris Fair on Instagram

Justin Brashear on LinkedIn

Brian Davidson on Linkedin

Get Started with NIL

If you're navigating NIL or supporting a student-athlete, understanding branding and strategy early can make a major difference in long-term success. Make sure to get started for free at nilgameplan.com

Discover how Darius Willis, former college athlete and founder of Scout Sync, is transforming the recruiting landscape by leveraging global exposure and technology. This episode delves into the realities of athlete recruitment, NIL's evolution, and innovative solutions for underserved athletes.

About Darius

Darius Willis is a former Under Armour All-American, D1 running back at Indiana University, and NFL tryout veteran who went on to coach the Swiss National Football Team as Offensive Coordinator. Over a 14-year coaching career spanning high school through international play, he's helped more than 1,000 athletes secure scholarships, contracts, and draft placements — and that experience exposed a broken recruiting system that leaves talented players behind every day. It's what drove him to found ScoutSync, an AI-powered platform connecting athletes with opportunities worldwide, and to build dariuswillis.com, where he offers training, recruiting consulting, and sports tech advisory services. A 2026 Mira Awards Finalist for Rising Entrepreneur of the Year and 2025 High School Football Hall of Fame inductee, Darius is one of the few people in sports who has competed, coached, recruited, and built the technology to change how it all works.

Timestamps
00:00 - Darius Willis’ background: From Indiana football star to founder
01:12 - Early recruiting process: Traveling, letters, and family pride
02:09 - Benefits of early exposure and competitive confidence
03:00 - First Under Armour All-American Bowl experience and lessons learned
04:23 - Misunderstandings about the current recruiting landscape
05:33 - How Scout Sync bridges athlete exposure gaps locally and globally
06:39 - Common mistakes athletes make: Lack of proactivity in recruitment
08:13 - Unique features of Scout Sync’s transparent, ecosystem-driven platform
09:51 - The evolving NIL landscape at high school and college levels
11:04 - The effect of NIL on opportunities, pressure, and family guidance
12:15 - Building social media presence: Focus and strategy for young athletes
13:24 - Overlooked athletes: International and non-revenue sport players
14:22 - How Scout Sync supports athletes worldwide regardless of sport
15:30 - Lessons learned in entrepreneurship from sports to tech
16:28 - Future outlook: Structure, regulation, and inclusion in NIL and recruitment
17:46 - International athletes' increasing access to NIL opportunities
18:04 - Connecting with Darius: Scout Sync platforms and future initiatives

Connect with Darius
Scout Sync

Darius Willis on LinkedIn

Follow Brian Davidson
LinkedIn: https://www.linkedin.com/in/brianrdavidson/

If you're navigating NIL or supporting a student-athlete, understanding branding and strategy early can make a major difference in long-term success. Make sure to get started for free at nilgameplan.com

In this in-depth interview, Mitch Gilfillan shares his unique journey from college athlete to coach and attorney, providing expert insights into NIL, college sports law, and athlete branding. Discover how recent changes in college athletics impact athletes, families, and universities, and learn practical advice for navigating this evolving landscape.

About Mitch: Mitch Gilfillan is a nationally recognized attorney and trusted voice in college sports and NIL law. A former Division I basketball player who competed in the NCAA March Madness Tournament, Mitch combines firsthand athletic experience with his legal work advising athletes, families, universities, and organizations on NIL opportunities, athlete branding, endorsement agreements, and the evolving landscape of college athletics.

As a partner at Quinn Johnston, Mitch is a sought-after speaker on the intersection of sports and law, presenting at major universities, national conferences, and the NCAA Final Four. He has also consulted for the NBA Players Association and has been featured by ESPN, CBS, Sports Illustrated, and the New York Post for his expertise in college basketball and NIL-related issues.

Timestamps
00:00 Introduction to Mitch Gilfillan and his background
01:15 Mitch's journey as a college athlete and recruiting story
02:07 Transition from playing to coaching in college basketball
02:32 Pursuing law and the intersection with sports
03:11 The emergence of NIL and its origins
04:06 How Mitch's experience shapes his advice to athletes
05:20 The long-term perspective on college sports decisions
07:04 The rapid evolution of NIL since 2021
09:14 Legal advice for high-end NIL deals and tax considerations
12:13 Difference between revenue share and true NIL endorsement
15:06 Opportunities for non-revenue sports athletes
15:54 Building athlete branding from a young age
17:36 Legal considerations for starting an LLC early
19:06 Mitch's role with the NBA and athlete education
21:26 Lessons learned from advising top athletes
22:53 Where to find Mitch Gilfillan online

Resources
Mitch Gilfillan on LinkedIn - https://www.linkedin.com/in/mitchgilfillan/ Gilfillan on Instagram - https://www.instagram.com/gilfillin21/

Follow Brian Davidson
LinkedIn: https://www.linkedin.com/in/brianrdavidson/

Get Started with NIL

If you're navigating NIL or supporting a student-athlete, understanding branding and strategy early can make a major difference in long-term success. Make sure to get started for free at nilgameplan.com

In this episode, Jeremy Evans, founder of California Sports Lawyer, dives into the complexities and legal nuances surrounding Name, Image, and Likeness (NIL) rights, college sports structure, and the evolving legislation across states. If you're interested in how legal, educational, and industry shifts are shaping sports, this conversation is essential listening.

Timestamps

• (00:02) Jeremy Evans’ background and how he got into sports law
• (01:21) Transition from traditional legal careers to sports and entertainment law
• (02:44) The influence of baseball arbitration competitions on Jeremy’s passion for sports law
• (04:07) The importance of entrepreneurs being naive and learning as they go
• (06:40) What holistic representation for athletes should include
• (07:01) When families should start building their NIL team
• (09:09) Legal considerations for high school athletes involved in NIL
• (10:20) Key clauses in NIL agreements: payment, obligations, duration
• (12:23) How state laws are evolving and their implications
• (14:56) Structural issues in college sports: transfer portal, athletic payments, and policy reforms
• (17:36) NIL’s impact on non-revenue sports and university funding
• (19:12) State legislation responses and future legislative directions
• (20:47) The implications of NIL creeping into high school sports
• (23:28) The future of NCAA regulation and potential for organized oversight

Connect with Jeremy Evans:

California Sports Lawyer Website

Follow Brian Davidson
LinkedIn: https://www.linkedin.com/in/brianrdavidson/

If you're navigating NIL or supporting a student-athlete, understanding branding and strategy early can make a major difference in long-term success. Make sure to get started for free at nilgameplan.com