Why Youth Sports Feels Chaotic, Why Parents Carry the Load, and How Onsides Is Trying to Make It Easier
Eric Kasimov talks with Dave Yoo, founder of Onsides, about the business, emotion, and logistics behind youth sports. Dave started building Onsides after managing multiple team apps for his daughter’s teams and schedules and realizing how much work parents are carrying just to keep up.
Eric and Dave get into rising costs, travel, private training, parent behavior, NIL, recruiting, AI, college, Silicon Valley, and the growing cognitive load on families. Youth sports can still bring people together, but the system around it has become harder to manage — and Onsides is built around that reality.
What Dave Yoo and Eric Discuss:
- Why youth sports has quietly become a $50B+ machine
- The chaos of managing multiple teams, apps, and schedules
- The real “cognitive load” parents are carrying
- How AI can actually reduce stress when used right
- The hidden financial and emotional tax on families
- The gap between recreational play and high-pressure club sports
- Sideline behavior, pressure, and the culture around kids’ sports
- NIL, recruiting, and how early the stakes are starting
- What AI changes for students, founders, and careers
Full Show Notes
Youth sports has become a massive industry, but the experience for families still feels fragmented. Parents are managing schedules, travel, training, and communication across multiple platforms — often without a clear system tying it together.
Dave Yoo saw that firsthand and built Onsides to simplify it. What starts with scheduling expands into a broader idea: organizing everything that flows from it — from travel and training to coordination across teams and seasons.
The conversation explores how youth sports has evolved into a high-pressure, high-cost environment, where expectations, behavior, and opportunity (including NIL) are shifting earlier than ever. It also looks at how AI can help — when it’s grounded in real data and real problems.
Notable Quotes
- “When you become a parent of a youth athlete, your favorite athlete is no longer LeBron James or Steph Curry. It’s that little kid down the hall.”
- “Every feature that we build must reduce cognitive load for parents.”
- “We don’t believe parents need to pay more or should pay more to organize their lives.”
- “The on-ramp is the scheduling. But everything that powers that $50 billion market is driven from the schedule.”
Chapters in This Episode
00:14 – The business and emotion of youth sports
03:00 – Why Dave Yoo started building Onsides
05:00 – The chaos parents deal with across platforms
06:12 – The vision for an all-in-one youth sports app
08:26 – Reducing cognitive load for parents
10:48 – Private coaching, training, and monetization
12:29 – How Onsides is using AI behind the scenes
14:40 – Guardrails, hallucinations, and reliable data
16:36 – AI’s impact on software and engineering
18:57 – Advice for students and young founders
20:09 – College, careers, and uncertainty
21:49 – Growth, distribution, and parent adoption
24:23 – The commercialization of youth sports
27:07 – Recreational sports vs. club intensity
29:00 – Parent pressure and youth sports culture
31:44 – NIL, recruiting, and what comes next
38:00 – Media, podcasts, and startup storytelling
41:38 – AI, search, and signal amplification
43:51 – Phones, social media, and young athletes
47:42 – How to find Onsides
48:39 – Where to connect with Dave Yoo
Connect with Dave Yoo & Onsides:
Onsides | Onsides App
Dave Yoo on LinkedIn
Connect with Eric & SportsEpreneur:
SportsEpreneur.com | X | LinkedIn
Eric on LinkedIn | X
Related Youth Sports Content
- The State of Youth Sports
- The Real Cost of Youth Sports in 2026: What Families Actually Spend
- The Pressure Placed on Kids in Youth Sports
- High School Athletes and NIL: The Future of Youth Sports
- Make Youth Sports Fun Again
Eric Kasimov is the founder of SportsEpreneur, part of the KazSource media network. Since launching the platform in 2015, he has hosted over 500 podcast episodes, written and published more than 1,500 articles, and advised business leaders, founders, and creators on building authority through media strategy.
Through his brands — KazSource, KazCM, SportsEpreneur, and QuietLoud Studios — Eric leads teams that produce podcasts, develop brand platforms, and help companies grow through modern content ecosystems. He also scaled KazSource Insurance into a seven-figure boutique agency, providing the foundation for the broader media network he operates today.
His work has been featured in Forbes, Axios, and Front Office Sports, and his podcasts have included conversations with top founders, investors, and athletes turned entrepreneurs.