Josh Chernikoff on Costly Business Partnerships and Sales Mistakes

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.

Questions and Topics:

• What’s your favorite mistake?
• Did you realize it was a mistake right away, or did that realization develop over time?
• What lessons did you take from that experience?
• How can someone evaluate whether a business partnership is the right fit before committing?
• Can you share more about the pricing change that didn’t go as planned?
• How do you differentiate between handling objections in sales and truly learning from objections?
• Why limit your business to education sales when your methodology could apply more broadly?
• What are the most common sales mistakes you see, either in education or in general?
• How important is it to focus on finding the right leads versus just generating more leads?
• How do you identify high-quality leads and refine your targeting strategy over time?
• What role does messaging play in sales success, and how do you help clients improve it?
• How did your career start in TV sports broadcasting, and what led you to leave?
• What lessons from broadcasting have helped you in your current work?
• Was there a broadcast journalism equivalent to the Medill F?
• How should professionals use LinkedIn to position themselves effectively?
• What advice do you have for people struggling with lead generation?
• How do you know when it’s time to pivot your business strategy based on market feedback?