My guest for Episode #295 of the My Favorite Mistake podcast is Josh Chernikoff, a seasoned expert in the education sector with nearly 20 years of experience in EdTech, sales, and entrepreneurship.

Episode page with video, transcript, and more

Josh is the founder of the EdSales Elevation Experience, a 12-week program designed to help education companies build lead-generation engines that consistently book 12-20 high-quality sales calls per month.

He has worked with hundreds of thousands of students and educational leaders, helping businesses scale with innovative, repeatable sales processes. Josh is also a Milken-Penn GSE Competition Judge, StartEd Mentor, and host of the podcast "Breaking the Grade."

In this episode, Josh Chernikoff shares the hard lessons he learned from choosing the wrong business partners and how that misalignment impacted his second company. He reflects on how personality fit and communication styles can make or break a business relationship, emphasizing the importance of testing collaborations on smaller projects before fully committing. Josh also opens up about a pricing strategy misstep that led to significant financial losses and the unexpected impact of the pandemic on his after-school enrichment business.

Beyond mistakes, we dive into what makes a repeatable, scalable sales process—why businesses struggle with lead generation, how to refine messaging, and the importance of credibility in attracting the right clients. Josh explains his Raise Your Hand campaign as a way to identify high-quality leads and tailor sales efforts to what potential customers actually need. We also discuss the power of having one clear offer, the role of objections in refining sales strategies, and why he stays laser-focused on education sales despite his methodology’s broader applicability. Toward the end, Josh shares stories from his early career as a TV sports broadcaster, including lessons learned at Northwestern’s Medill School and the intensity of live television.