The 21-Day Challenge That Books Coaching Clients

In this episode, Ken Freire sits down with performance coach Jon Lester to unpack his journey from high school educator to building an authentic, purpose-driven coaching business. Jon shares how listening to conviction, starting as a side hustle, and prioritizing service over sales helped him grow Relentless Pursuit 247. Together, they explore why community—not pushy tactics—has become Jon’s biggest lever for impact and growth, especially for men seeking leadership, accountability, and brotherhood.Resources Mentioned• Relentless Pursuit 247 (Skool Community) – https://www.skool.com/relentless-pursuit-247• Atomic Habits by James Clear – https://jamesclear.com/atomic-habits• The Compound Effect by Darren Hardy – https://darrenhardy.com/thecompoundeffect/Timestamps• 00:00–02:35 – Jon’s background in education and the calling to pursue coaching• 02:36–04:16 – Recognizing discontent and the conviction to change paths• 04:17–05:56 – Why Jon chose a side hustle approach instead of quitting outright• 05:57–08:38 – Landing his first client and realizing coaching was the right path• 08:39–10:22 – Lessons learned from rejecting pushy sales tactics• 10:23–12:35 – Community as the biggest lever for growth and transformation• 12:36–15:22 – Balancing free value with paid coaching offers• 15:23–18:14 – Using 21-day challenges to build discipline, trust, and momentum• 18:15–23:56 – Encouragement for struggling entrepreneurs and playing the long game• 23:57–29:59 – Rapid-fire business trends, advice for kids, and where to find Jon