444 | Kaleb O’Very | How to Grow 300% and Love Every Challenge

Are you still trying to do everything alone, risking burnout and missing your true potential?

This episode features Kaleb O'Very, the three-time “Operator of the Year” who scaled his student business to unprecedented heights, and Chris Thompson, Student Works Management Program Head Coach.

You’ll hear Kaleb’s raw and inspiring journey from self-doubt and bad habits to elite leadership and record-breaking business growth. Together, they reveal how building a winning team, mastering the art of integrity, and leveraging habit-breaking techniques can propel any young entrepreneur toward industry-defining results.

If you want to avoid years of struggle and discover what it really takes to lead a high-performing team, this episode is your unfair advantage. Listen now before everyone else catches up. These lessons might just be the missing blueprint to your next breakthrough.

Timestamped Highlights

1. [00:00] – Why trying to do it all nearly killed Kaleb’s growth (and what triggered a 300% leap)
2. [00:04:17] – From follower to leader: The surprising catalyst that flipped Kaleb’s mindset
3. [00:07:17] – Mistakes most young entrepreneurs make hiring and leading their first team
4. [00:08:42] – The unexpected business impact of personal habits (sleep, nutrition, mindset)
5. [00:13:15] – How true delegation and coaching unlocked six-figure results for Kaleb’s team
6. [00:16:27] – “Restoring integrity”: The proven method for fixing breakdowns and building trust
7. [00:21:02] – The uncommon team ritual behind this year’s Mexico-bound and President’s Club superstars
8. [00:34:32] – Daily commitments and Kaleb’s single best tip for energizing and bonding a winning team

About the Guest

Kaleb O’Very is a multi-year “Operator of the Year” with the Student Works Management Program who shattered regional business records by leading his team from $120K to over $1.4M. In 2023, he managed and coached five rookie operators to collective President’s Club and Mexico trip success, embodying what next-level delegation and leadership can achieve. Known for his relentless grit, fierce team-building, and the ability to turn high-pressure opportunities into thriving growth engines for all involved.

🔗 LinkedIn

Resources & Links Mentioned

1. ABR – Always Be Recruiting strategy
2. LinkedIn Learning

Important Links

1. Connect with Chris: Website |