Listen:
Check out all episodes on the My Favorite Mistake main page.
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.
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?
Scroll down to find:
- Video version of the episode
- How to subscribe
- Quotes
- Full transcript
Find Josh on social media:
Video of the Episode:
Quotes:
Click on an image for a larger view
Subscribe, Follow, Support, Rate, and Review!
Please follow, rate, and review via Apple Podcasts, Podchaser, or your favorite app — that helps others find this content, and you'll be sure to get future episodes as they are released weekly. You can also financially support the show through Spotify.
You can now sign up to get new episodes via email, to make sure you don't miss an episode.
This podcast is part of the Lean Communicators network.
Other Ways to Subscribe or Follow — Apps & Email
Automated Transcript (May Contain Mistakes)
Mark Graban:
Hi, welcome to My Favorite Mistake. I'm your host, Mark Graban. Our guest today is Josh Chernikoff. He is a seasoned expert in the education sector. He started a couple of businesses.
He's got more than 20 years of experience in ed tech, sales, and entrepreneurship. He is the founder of the Ed Sales Elevation Experience, a 12-week program designed to help education companies build a lead generation engine. So we're going to talk about that later in the episode.
He's worked with hundreds of thousands of students and educational leaders, helping businesses scale with innovative and repeatable sales processes.
He is a MILKEN-Penn GSE competition judge, a StartEd mentor, and host of the podcast Breaking the Grade. So, Josh, welcome to the podcast. How are you?
Josh Chernikoff:
Thank you. I appreciate the welcome. I appreciate that very warm welcome. I had forgotten about some of that stuff, so thank you for the reminder.
Mark Graban:
It’s all on your LinkedIn page. I just put it together into the bio.
Josh Chernikoff:
All accurate and correct, I hope.
Mark Graban:
All accurate and correct. I was afraid I'd made a mistake.
Josh Chernikoff:
You nailed it.
Mark Graban:
Well, speaking of warm introductions, we had a very warm connection made by Hank Levine, who was a guest in episode 219 of this podcast series. How do you know Hank? Our listeners hopefully heard his episode—great guy.
Josh Chernikoff:
Yeah, let’s see here. First of all, both Hank and I are from the Washington, D.C. area. We could probably do one degree of Jewish geography between the two of us if we really tried, which wouldn’t be very hard.
We’re both in education and ed tech, and we were both at an event on June 21 at Penn’s Graduate School of Education, where I was speaking about lead generation. Hank sat in on my part of the day, and we got a chance to reconnect. It was nice to rekindle the relationship with him. We have all these things in common, so it was just kind of off and running very quickly.
Mark Graban:
Yeah. Well, one of the things you now have in common is being a guest here. And I’m sure, like Hank, you’ve got a favorite mistake story. So, Josh, what’s your favorite mistake?
Josh Chernikoff:
Yeah, you know, I’ve been thinking about this. My favorite mistake—and I guess my favorite mistake is also the one that really took me out the most and hurt the most financially.
I think, potentially, choosing the wrong partners at the wrong time for my second business. And I wish those partners all the best. I don’t hold any ill will toward them, but I don’t think we were the right fit at that time for each other.
I’m in the process of watching the show Suits.
Mark Graban:
I’ve never seen it.
Josh Chernikoff:
It’s a great show. And the two main characters, one of them is Harvey and one is Mike. Harvey’s really hard on Mike. He’s really trying to teach him, but Harvey doesn’t necessarily have the emotional skills to teach Mike the way he wants to be taught.
And I had a relationship like that in my second business with an investor who was also kind of our part-time CFO. He wanted to teach me, he wanted to help, but the way he was teaching and helping was not working for me.
The business really struggled to move forward, even though we had a phenomenal idea with our after-school enrichment business. We were in 82 schools up and down the East Coast, but we were struggling as a business internally. Then we made a pricing change that was not done well by the other partners.
That cost us a lot of money. And then we didn’t see this one coming, but there was a worldwide pandemic—if you didn’t hear about it.
Mark Graban:
So a shift to education at home and remote learning didn’t help with after-school programs?
Josh Chernikoff:
Yeah, not at all. And, you know, when the going gets tough, not everybody gets going in the right direction. It really caused the business to struggle.
So, again, I don’t—I don’t know if you listen to Howard Stern, but, you know, only peace and love for those guys. But my choice of business partners—I would also think that they would agree—was not the right time. We were not the right people for each other. And that really cost the business a lot of success, I believe.
Mark Graban:
Yeah, well, I appreciate you sharing that. And, you know, one thing—when we talk about mistakes, it’s a word we all know and use, but I think part of the context of the definition of a mistake is that when we make a decision, we believe in the moment that it’s the right decision.
Then we learn something down the road that makes it clear that things didn’t turn out the way we predicted. So, thinking of that—at the time, was there a prediction that that investor and bringing him in as a CFO was the right move?
Was it apparent pretty soon, like right away, that this was a mistake? Or did your view of that kind of evolve gradually as you were working together?
Josh Chernikoff:
I would say that it was pretty apparent pretty quickly. When we started working together, there were some serious personality differences in how we would be leading the business.
But there was no turning back. Money had moved, contracts had been signed.
So, you know, we were going to try and make the best out of it. And again, I know that this particular person has a good heart. So he’s a good person. And I was not a—I was a good person at the time, I believe I still am. But I was younger.
Right now, I’m 45. So I was probably 35 or, you know, 33, 34. Different person. And so, again, the feedback I was receiving, the direction they wanted to take my business—it just didn’t work well.
There was collateral damage. I believe the business suffered in terms of success. We could have had more success. We measure success by adding more schools, by the money we made for shareholders, and by the relationships with partners.
But I think at the root, it just, again, wasn’t the right people at the right time. If it had been now, honestly, it might have been a better fit because I’m more receptive to feedback and more focused on margins and P&Ls and things like that.
Mark Graban:
So other than, I mean, it sounds like what I hear you saying is that you changed, grew, and matured. Was there another lesson learned? If you were going to be in a similar situation in the future, was there a lesson about how to evaluate personality fit up front and maybe avoid that same situation?
Or is there advice you might have for others about how to know if it's really going to work out, working together so closely?
Josh Chernikoff:
I think, to answer that last question, maybe working on something small together first—a smaller project—is potentially one way of doing that.
I was obsessed, to use an overused term right now, with expansion and getting investors. I got friends and family for my first business and even more in my second. And I was obsessed with expanding out of the Washington, D.C. area.
If I could do things over again… As I coach people in education, I always encourage them to really try and dominate where they live first, especially in education. You need to get out there, meet in K–12, go meet the principals, go meet the teachers, go meet the superintendents—those are the people whose lives you are transforming with your product.
Understand how you are transforming their lives. Learn it, and learn it, and learn it.
We did that to a degree in D.C., but I wanted to get to New York. I wanted to get to Connecticut. I wanted to get to New Jersey. And you can do those things, but the synergies aren’t there for scale, and that begins to hurt the business and take your eye off the ball—off of really delivering quality.
And then, if you put all that aside, a lot of people come to me for lead generation, and they say, “Well, you know, I’m in the process of raising money.”
And I’m like, “For what? You haven’t done anything yet.”
You want an investor to come in when you’ve figured it out. That’s how you get leverage.
And they say, “Well, I’m talking to a lot of investors.”
I say, “I’m not surprised. That’s what they’re paid to do.”
Mark Graban:
Yeah, but are they investing?
Josh Chernikoff:
Yeah, they’re looking for a needle in a haystack. So they’re happy to take a 15–20-minute call. They’re happy to throw out— and I don’t blame them—they’re happy to throw out a term sheet that sucks.
But at the end of the day, you need to get traction. You need to have a really good offer. You need to have a really good lead gen system. You need to be a subject matter expert.
Those three things—basic. Obviously, there are many more things to do, but those three basic things are going to help lead you toward leads on repeat so that an investor can pour gasoline on a fire, period. Hard stop.
I don’t really think I’ll ever have business partners again. I say that now, but maybe, maybe not. Even though I’m a good person and I love people, maybe I just don’t really want partners in my business. And maybe that’s where I’ve evolved to.
Mark Graban:
I want to talk more about the coaching and the work that you do around lead generation and sales processes. But I was wondering if you could talk us through a little bit more about the pricing change that wasn’t done well.
If you could share what the expectation or prediction was versus how that played out?
Josh Chernikoff:
Yeah, in my second business, I had three pricing strategies, and we worked very closely with providers.
The second strategy—we decided to lower our take from the providers, like the Kung Fu provider, the pottery provider. But we kept their payment the same, and we had our highest volume of sales. But we weren’t making enough to cover what we had to pay out.
Plus, because we had more programs running, we needed more people on the ground, we needed more people in the back office.
And we ended up losing—I’ll just say—hundreds of thousands of dollars. And that came out of the partners.
At the end of the day, the knife was put in my back. Whether or not I believed I should have gotten the only knife, it doesn’t matter.
I did. I took it. Not happily, but I took it.
And we got through it. We got through it. We were on the other side of it.
And then the pandemic happened.
Mark Graban:
Yeah, well, it sounded like there was an impact on relationships, not just the bottom line.
Josh Chernikoff:
And that’s the part we never really recovered from. You know, the trust was gone. The fun was gone.
Although we were trying to recreate it…
And think about that—when I say it, it makes it sound like a romantic relationship, you know?
But being “in bed” with partners is kind of like that. And you can lose your love for each other, and it’s tough to rekindle.
Mark Graban:
Well, and you made me think a little bit when you talked about the idea of mitigating the risk of “getting into bed”—to quote-unquote marry a business partner or investor.
That small project might be kind of like dating a little bit first.
Not just an initial review of a profile or an introduction that’s made, but actually working together on something small first to test things out.
And, you know, people—whether in business or in life—still go through that and still get married, and sadly, things don’t work out.
It makes me think—how often do co-founders go to counseling to say, “Hey, we’re committed to working this out,” as opposed to just giving up on each other?
Josh Chernikoff:
That’s a really interesting business idea. I’ve never thought about that, and I didn’t even see it coming when you were mentioning it.
But it is a really interesting idea. I don’t know if it exists. I don’t know if it would have worked for us.
But I would have been willing to try it.
Mark Graban:
I need to reach out. I’ve had a lot of psychologists and counselors on the show.
I should reach out to some of them, because I think some of them have delved into business coaching.
And I’m curious how much of that relationship work applies.
That’s very interesting. If there’s something there, somebody’s probably working in that direction.
Mark Graban:
Let’s talk about your work, Josh. One phrase I think is interesting is “repeatable sales process.” Or even just the idea of a sales process.
How often do people push back and say, “Look, every deal is unique, don’t force too much, don’t stifle me with process”?
Is there pushback around process, or is it a mistake to think process doesn’t apply?
Josh Chernikoff:
I think it’s a big mistake. I’ve made the mistake.
And I think that, you know, I have built this business based on objections and rejection.
I can walk you through a process that I can see in my own head—what I call my signature solution.
A signature solution is my clearest way of describing my business to you. Generally, it’s done visually.
But my nine-step process, which takes about 12 weeks to complete, starts with really understanding your ideal client—which most people think they’ve done, but they haven’t necessarily done it my way.
We work through that, and then we build out credibility and think about the value of credibility.
And credibility is not just your LinkedIn profile with all the awards and schools you’ve ever attended.
Credibility is you being a subject matter expert.
Credibility is you talking about things that your ideal client cares about—whether it’s on LinkedIn, on a show like this, in a blog post, or being published somewhere.
Then we go through a campaign. It’s called the Raise Your Hand campaign.
And in the Raise Your Hand campaign, it’s interesting—about four weeks into my program, I lose about 20% of the people for a little while.
The Raise Your Hand campaign is the first opportunity for you to get objections and rejections about your business.
Because you think this is your ideal client.
You have built out your LinkedIn based on who you think you are and how you can help someone.
Your headline: “I help who, using what method, get which results?”
When we do the Raise Your Hand campaign, we do it on LinkedIn and we ask people, “I’d like to talk to you about some things. I’d like to ask you questions.”
We’re not there to sell—we’re just there to gather information.
And if people don’t respond, it shows that you’re not the subject matter expert you think you are at this point. Or maybe they’re not your ideal client.
And from what we learn by listening, we create our signature solution.
Every one of my clients emerges with a signature solution—a nine-step process that takes them from confusion to clarity and demonstrates the transformation that occurs when they work with a client.
Then we move into targeting and then messaging.
I don’t care how good your credibility is. I don’t care how long your email list is. I don’t care how much listening you’ve done.
If your messaging is not good, then while your open rates might be decent, if people don’t reply, the messaging isn’t working.
Then we move into what we call the Engine Phase, which is when we start automating and scaling—using machines to get you more and more leads.
I mean, when we’re at our peak, we’re sending out about 600 to 800 emails per week with a 30% open rate and about a 10% reply rate.
Mark Graban:
It sounds like there’s a parallel to what you talked about before—about an investor wanting to put money into something after it’s already been figured out.
Some people in the Lean Startup community talk about product-market fit. You’ve got to experiment, find that fit, and then once you’ve got it, boom—move forward.
It sounds like your process is about making mistakes or iterating to find what works—and then automating it.
Otherwise, it sounds like a mistake to automate something that’s not working well.
Josh Chernikoff:
Right, exactly. And I think it’s more about objections than mistakes.
I like people to run toward the objections.
You know, “What about my process doesn’t work for you?”
I want my ideal client to be completely aligned with my process.
When I walk away from a strategy call, I call it a Self-Identification Call.
Because I’m going to ask you a set of questions about what you think lead generation should be for your education company.
And the way you answer those questions helps me determine if you’re a good fit.
Then I’ll talk to you about my process, and we have to be 100% aligned on it.
Because we are going to drink the Kool-Aid together.
And assuming we’re drinking the same Kool-Aid—drinking my 3E Kool-Aid—this process will work for you.
And then I guarantee it for people.
Which sounds cheesy, even coming out of my mouth right now—that I can guarantee it.
But the difference is this:
In my first business, which was a tutoring business, parents would say, “Hey, I want my kid to go from a D to an A. Can you guarantee that?”
And I’d say, “We spend two hours a week with your kid. I have no idea. We’re going to do our best during those two hours.”
In my second business—the after-school enrichment business—PTAs would ask, “Can you raise us $50,000?”
And I’d say, “I’ll raise you $100,000! But you have to promote, you have to get people to sign up. But I won’t guarantee anything.”
In this business, I can guarantee it.
Because there are some companies in education that get my system eight weeks into a 12-week program.
For others, it might take 24 or 36 weeks.
But I will keep working with them until they get it.
Because it’s just a matter of tweaking what we already know works.
Mark Graban:
So when you talk about objections, it sounds like your approach—your process of running toward objections—is different from what people usually call objection handling in sales.
What I’ve heard about objection handling is that you have to have a response ready.
Someone gives you an objection, and your job is to prove them wrong.
It sounds like your approach is different—you’re not trying to say, “You’re wrong.”
Instead, you’re trying to learn from the objection.
Josh Chernikoff:
It’s a little bit of both.
Let’s take conferences as an example—especially in the education space.
I hear a lot of people say, “I go to conferences, and they’re a total waste.”
And I say, “Okay, I’ve been there. I used to hate conferences. What specifically isn’t working for you?”
And they’ll say, “I spend a lot of time and money to get there. I hand out my business card, I collect business cards, I pay for a booth, I get home, and then I have to do all the follow-up while also keeping up with my actual work.”
Well, okay—some of those things I can help with, and some I can’t.
Let’s talk about your messaging.
When you’re at that conference, tell me what you say.
Tell me who you are.
Let’s use a formula.
Mark Graban:
When you have that first interaction, someone wanders by your booth and says, “Oh, hi, who are you?”—what do you say?
Josh Chernikoff:
They’re chewing gum, looking at their phone, not wanting to be noticed. And you walk up to them and say:
“My name is Josh Chernikoff. I help companies in education generate 15 to 20 high-quality leads per month using my method, the Ed Sales Elevation Experience. Do you want to learn more?”
Can you do that?
And when you can do that at a conference, it changes the whole experience.
Because you’re going to find the people who actually want to learn from you and who might be your ideal client.
And that changes everything.
So, I can’t necessarily change those objections about spending a lot of money, or taking a lot of time, or gathering business cards.
But if we get to the root of the issue—which, in this case, might be messaging—if we fix that, then you’ll have a much better experience at the conference.
So, understanding people’s objections… that’s key.
Now, back to my own business—people will say, “I go to conferences all the time, and they’re such a waste for me when it comes to lead generation.”
And I say, “Well, actually… what if I told you I could show you how to do it the right way?”
Mark Graban:
So you’re not telling them that conferences are a waste—you’re saying the way they’re doing it is a waste.
Josh Chernikoff:
Exactly! I have a system.
I tell them why we do what we do—I just don’t tell them how.
The how happens when you join our cohort. That’s when you get to dive in with me.
And another really important point: We’ve had 97 companies go through the Ed Sales Elevation Experience, and all those 97 companies are so tight.
We’ve created this community—and it’s growing.
And everyone in the community is there to support each other as well.
So not only do people join the Ed Sales Elevation Experience, but they also join our growing community.
And that’s a huge benefit.
Mark Graban:
So, right there on your LinkedIn profile, you’ve got that formula for your introduction:
“I help who, using which method, to get which results.”
That’s the first thing on your LinkedIn page:
“I help companies in education build lead generation engines that book 12 to 20 high-quality sales calls a month through my 12-week Ed Sales Elevation Experience.”
Although earlier, you mentioned it’s now 15 to 20—so maybe you need to update that!
Josh Chernikoff:
We’re doing better—I need to update it!
Mark Graban:
This is prompting me to think through what my LinkedIn headline should say, using a formula like that.
What’s my messaging?
And my one question for you is this:
It sounds like your approach could help me or someone like me—someone selling speaking, consulting, coaching, and various services.
But I’m not in education, edtech, or ed sales.
So… why limit yourself to ed sales?
Is it just a matter of “These are the people I love working with” or “This is my ideal client”?
Because it sounds like this methodology could help a lot of people outside education.
Josh Chernikoff:
One hundred percent—it could help people outside education.
But I’m very proud to say that I only work in education.
Because these are the people I know how to sell to.
I know their objections.
There’s not one objection in this space that I haven’t heard before.
So, in terms of positioning myself as a subject matter expert, I can say with confidence, “I am the expert in lead generation in education.”
Which, by the way, is a very tough place to sell.
And you know what? My cohorts are growing.
We used to start one cohort every three months with 10 companies.
Now, we had a waitlist—so we’re starting two cohorts this week instead of one.
The first one filled up, and we only have two spots left in the second.
And every single company in those cohorts is in education.
So, would I love to help people outside education?
Sure!
But right now, this is where I can be most effective.
And actually, it’s my hope that one day my daughter Camila—who, by the way, has been selling bracelets at her school long before we knew about it—will take over this business.
And maybe she will take everything I’ve built and say, “My old man, he could only sell to companies in education… but I have taken what he taught me and now we’re teaching it to the world.”
She can take the business in that direction.
But for me, right now, I believe in staying in my lane.
Mark Graban:
Sure, sure.
Josh Chernikoff:
I believe in the power of one.
And that’s actually one of the most important things I teach my clients.
Because my clients, especially in education, have multiple stakeholders.
Are you selling to a superintendent? A principal? A teacher? A PTA? A parent? A district administrator?
We figure out one key group that you’re selling to.
The one group that you can talk to directly about their challenges.
Now, sure, we also want to demonstrate benefits to the other stakeholders.
But we want you to be speaking directly to one key stakeholder about how you can transform their world.
I practice what I preach.
Mark Graban:
So, Josh, from your experience and observations working with others, what are some of the most common sales mistakes?
Either ones that are unique to education, or just broadly applicable in any industry?
Josh Chernikoff:
Number one: No clear offer.
I long ago realized that a confused mind does not buy.
And what I’ve also learned?
A confused mind can’t sell.
So, not only is it important for your potential buyers to hear one clear offer…
It’s also important for you to have one clear offer that you can communicate effectively.
Mark Graban:
As opposed to a portfolio, which I just heard myself describing, kind of trying to apply this to myself.
It sounds like I don’t have one clear offer. If you want to call me a confused… I’m calling myself a confused mind.
Josh Chernikoff:
Could be, yeah.
But I think that if you’re clear on your offer, and you’ve spent years and decades refining it, that’s one thing.
But if you’re under a million dollars in revenue, one clear offer—and getting damn good at that—is the way to go.
Another big mistake?
People don’t have a lead generation system.
I know this is a huge issue in education, but I hear it in other industries too.
People are constantly just looking for that next lead.
Figuring out the next contract. The next grant. The next conversation.
And these things need to be on repeat.
I always think of it like golf—I’m a big golfer. Not a good golfer, but a big golfer.
It’s got to be like getting your driver in your hand—it has to be the same thing every single time.
Nice and easy.
You don’t want every swing to be different, and you don’t want to be tense every time you step up to hit the ball.
When you have leads on repeat—when you follow a system—I call it a concrete closing system—you don’t have to constantly worry.
I just got off two phone calls before this.
One was with a very successful woman who I could tell just wasn’t quite bought in.
So I said, “Hey, if you want to do a follow-up 45-minute call, no charge, let’s do it.”
The next person?
We were 10 minutes in, and I said, “My next step is a strategy call—let’s book it.”
Because he was bought in.
He gets it.
So, a clear offer, knowing that you can get leads on repeat, and then finally…
Having credibility.
I believe credibility sells overnight.
When someone reads a LinkedIn post from you…
When they get an email from you…
When they hear you on a podcast like this…
The first thing they’ll do?
They’re going to Google your name.
And hopefully, they can spell your last name—like mine.
Mark Graban:
Right.
Josh Chernikoff:
And what’s going to happen?
They’re probably going to see your website.
But before that, they’ll most likely check your LinkedIn profile.
I don’t teach a LinkedIn course, but I think LinkedIn is one of the best places to boost your credibility.
Because people know how to read a LinkedIn profile quickly.
And if it’s structured correctly, your LinkedIn profile should be a sales funnel—not a résumé.
Think of it as a funnel:
- Your banner image.
- Your profile picture.
- Your headline.
We talked about that formula earlier: “I help who, using what method, get what results.”
Then, your About section.
Your About section shouldn’t just be a boring summary of your experience.
It should ask questions that resonate with your ideal client.
It should demonstrate credibility.
And it should have a call to action.
That’s a funnel.
So, to go back to your original question—what mistakes do people make?
- They don’t have a clear offer.
- They don’t have a lead generation system.
- They aren’t building their credibility day in and day out.
Mark Graban:
When I look at your LinkedIn profile, it starts right off with questions:
“Is your education business struggling to gain traction?”
“Are you having a hard time pinpointing your ideal client and how to gain their business?”
“Do you want a dialed-in sales process to attract new clients and transform your bottom line?”
And then it moves into your credibility.
It’s not all questions, but it’s making me think—I need to spend more time looking at your profile as a model and maybe do some experiments with my own.
But I wanted to ask something else.
When we talk about lead generation, there’s a funnel.
A certain percentage of leads will turn into sales generation—or let’s call it happy client generation.
How important is it to think about finding the right leads—the ones most likely to convert—instead of just getting more leads?
Josh Chernikoff:
At the ripe old age of 45, I would say it’s the most important thing.
But had you asked me at 25 or 30, and you said,
“Josh, I just came across a list of 10,000 people in education—do you want it?”
I would’ve said,
“Sweet, I’ll email them and see what happens!”
Mark Graban:
10,000 leads!
Josh Chernikoff:
Yeah, “One of them has to work!”
But it doesn’t work that way anymore.
The email game has changed.
It’s so much better to clearly understand who wants to work with you.
Find them.
Give them value.
Bring them into your orbit.
And when the time is right—when the money is right—they will make the decision to work with you.
But first, they have to trust you.
They have to believe in you and your system.
So, I 100% believe that there’s no reason to generate leads that aren’t high-quality or high-converting.
It’s a waste of time.
Mark Graban:
But the question is—or I guess, the challenge—figuring out over time how to know which leads are better and how to find more of those people.
Josh Chernikoff:
In my process, that happens in the Raise Your Hand campaign.
By listening.
By really listening to the challenges people are facing.
For example, we had a client—her name is Toy—who runs a wonderful organization called EntreEd.
Her organization primarily works with schools up and down I-81, kind of through Appalachia.
And when Toy was running her Raise Your Hand campaigns, she was asking principals,
“What are your biggest challenges right now?”
And over and over again, they said,
“Retaining teachers.”
And Toy came back to me and said,
“Well, we have a little problem, because all they want to talk about is retaining teachers.”
And I said,
“No, Toy—that’s not a problem. That’s our answer.”
EntreEd provides professional development for teachers.
So we changed the conversation.
We went back to those principals and said:
“We have a way to retain your teachers, and it happens to be rooted in entrepreneurship. Are you interested?”
And suddenly… they all said yes.
So by listening, we were able to take the business in the direction it needed to go.
It wasn’t necessarily where Toy wanted to go at first.
But it was where her business needed to go.
And we went there together.
Mark Graban:
Wow. That’s a great story and a lot of great insights.
Again, we’re joined today by Josh Chernikoff.
One thing I didn’t put in your bio—but I have to ask you about before we wrap up—is that you started your career as a TV sports broadcaster.
Josh Chernikoff:
Yeah, yeah.
Mark Graban:
Was that going to be your favorite mistake story?
Or how did you get into broadcasting, and how did you move away from it?
Josh Chernikoff:
Well, I grew up in Washington, D.C., during a time when The Washington Post was filled with people like Michael Wilbon, Tony Kornheiser, and Tom Boswell—some of the greatest sportswriters of our time.
I grew up in D.C. when The George Michael Sports Machine was a thing.
Mark Graban:
Not the guy from Wham!
Josh Chernikoff:
laughs Not the guy from Wham!
Mark Graban:
I remember this George Michael.
Josh Chernikoff:
Yeah, and he had The Sports Machine.
So, I grew up in a town filled with phenomenal sportswriters and sports TV personalities.
All I ever wanted was to be on TV covering sports.
I studied print journalism in undergrad at American University…
Although, honestly, you could say I majored in partying—and I would have graduated with honors in that.
Then, I went to Northwestern for grad school—Medill.
Got my master’s in broadcast journalism.
And literally drove from Chicago to Harrisonburg, Virginia—because that’s where broadcast careers started back then.
Mark Graban:
Small market TV.
Josh Chernikoff:
Exactly.
James Madison University. WHSV-TV.
I got to cover JMU—which has now become a sports disruptor in college athletics.
I covered Bridgewater College, which was a D3 powerhouse in football.
And I even got to cover the Washington Redskins (now the Commanders).
So, when I left TV, I thought I’d never get back into it.
But now?
I have this beautiful mic in front of me.
I have my own shows.
And there isn’t a single live event I host where I don’t think:
“I cannot believe I get to do this.”
Because, when I worked in Harrisonburg, our “live” broadcasts were called Look-Lives.
Because we didn’t have a live truck.
We’d take a really long cord—I mean, really long—run it from the production studio…
Down a hallway…
Out the front door…
And onto the main square in Harrisonburg.
That was our version of going live!
So now?
The fact that I can sit here in my office, turn on a mic, and broadcast to Facebook, Instagram, LinkedIn, and YouTube all at the same time?
I feel blessed every single day.
Mark Graban:
I bet there were a lot of lessons from that career—about being a good communicator, an engaging communicator.
I went to Northwestern too, but for engineering—so, totally different world.
But Michael Wilbon is a Northwestern guy, and Medill has produced a ton of ESPN personalities.
A lot of them from Northwestern, Syracuse, and Missouri.
Josh Chernikoff:
Yeah, yeah.
Honestly, Medill was one of the hardest things I’ve ever done in my life.
That school does not mess around.
I barely made it out alive.
Mark Graban:
Was there something like the Medill F for broadcasting?
For those who don’t know, in Medill’s print journalism program, if you misspell a name or get a verifiable fact wrong in a story…
It’s an automatic F.
Even if the rest of the story is Pulitzer-level work.
Was there an equivalent in broadcast journalism?
Josh Chernikoff:
Yeah, but for me, it wasn’t just a Medill F—it was a “Get the F out of here” moment.
laughs
There was this professor, Joseph Angotti.
He was a legend.
We were doing our Medill Broadcast Network live to campus.
And Professor Angotti was counting us down…
“5… 4… 3… 2… 1…”
And I just kept talking.
And he hit his little microphone button—so you could hear it in the speakers—
“Josh, come see me in the production room.”
Everyone else left.
And he lit me up.
Mark Graban:
Verbally, or…?
Josh Chernikoff:
Both.
And honestly?
I deserved it.
I was disrespecting the rules of the studio.
I was disrespecting the people around me.
That was a tough year.
But it was also one of the best years of my life.
And you know what?
To this day, I cannot stand when people talk over each other on air.
Local news drives me nuts—because people just blurt out so much nonsense when they should just stop talking.
Also, I am a stickler for getting names right.
Pronouncing them correctly.
Spelling them correctly.
And if I do make a mistake?
I correct it immediately and own it.
So yeah, I got many Medill Fs.
That one?
That was a “Get the F out of here” F.
laughs
Mark Graban:
laughs I love it.
Well, thank you for the bonus story!
Our guest today has been Josh Chernikoff.
I’ll put links to his LinkedIn profile, his website (JoshChernikoff.com), and other resources in the show notes.
A lot of great takeaways today—both from Josh’s experiences in entrepreneurship and his insights into lead generation and sales processes.
Josh, thank you so much for sharing.
I really enjoyed this conversation.
Josh Chernikoff:
Yeah, thank you.
And I’ll just say this—
While I am super focused on the education space…
If I can help anyone, please feel free to reach out on LinkedIn.
I love playing around with headlines, helping with messaging, and brainstorming ideas.
I just happen to focus my business on education.
But I’m always happy to help.
Mark Graban:
Okay, well—thanks again.
Thanks so much for being a guest.
Josh Chernikoff:
Thank you.
Episode Summary and More
The Costly Mistakes of Entrepreneurship: Lessons from Josh Chernikoff on Business Partnerships, Sales, and Lead Generation
Introduction
Mistakes are an inevitable part of entrepreneurship, but some can be more costly than others. In this episode of My Favorite Mistake, Josh Chernikoff opens up about the biggest mistake of his career—choosing the wrong business partners—and how it ultimately impacted his company’s growth. He shares valuable insights into sales processes, lead generation, and why having one clear offer is essential for success.
If you’re an entrepreneur, startup founder, or business leader, this episode is packed with lessons that can help you avoid common pitfalls and build a more sustainable business. In this article, we’ll break down the key takeaways, including:
- The impact of choosing the wrong business partners
- The importance of refining sales and lead generation strategies
- Why objections in sales should be embraced, not feared
- How to position yourself as a subject matter expert
- The biggest mistakes entrepreneurs make in sales and marketing
Let’s dive in.
The Mistake That Cost Everything: Choosing the Wrong Business Partners
Josh’s favorite mistake was also his most financially painful—aligning with business partners who weren’t the right fit for his second company.
At the time, he believed he was making the right decision. His company, which focused on after-school enrichment programs, was growing rapidly and expanding into multiple states. However, early into the partnership, it became clear that there was a serious misalignment in communication styles and leadership approach.
The Red Flags Were There—But There Was No Turning Back
Josh recalls that personality clashes and differing visions surfaced quickly. However, since contracts had been signed and money had already exchanged hands, there was no way to reverse course.
“The way he was teaching and helping was not working for me. And the business really struggled to move forward.”
The partners introduced a pricing change that was poorly executed, leading to hundreds of thousands of dollars in losses. The business never fully recovered from that mistake. Then, the pandemic struck—shutting down after-school programs and delivering the final blow.
Lesson Learned: Test the Waters First
One of the biggest takeaways from this experience? Test partnerships before fully committing.
“Maybe work on something small together first. A project. See how you collaborate. See how you communicate.”
This simple step could have saved his business from unnecessary turmoil.
Sales and Lead Generation: The Biggest Mistakes Entrepreneurs Make
Beyond partnerships, Josh has seen countless businesses struggle with lead generation and sales. He now coaches education companies on how to build a repeatable system for bringing in new business.
Here are some of the most common sales mistakes he sees—and how to fix them.
Mistake #1: Not Having One Clear Offer
One of the biggest issues Josh sees with entrepreneurs is that they try to offer too many things.
“The confused mind does not buy. And the confused mind can't sell.”
Having one clear, compelling offer makes it easier for potential clients to understand what you do and how you can help them.
Mistake #2: Chasing Investors Before You Have Traction
A common misconception among startups is that securing an investor should be the first step to success. But as Josh points out, investors are looking for companies that have already figured it out.
“You want an investor to come in when you’ve figured it out—that’s how you get your leverage.”
Instead of spending time courting investors, focus on proving your business model first. Generate revenue. Build processes. Then, when you’re ready, investors will see the value in what you’re doing.
Mistake #3: Avoiding Objections Instead of Learning from Them
Sales objections aren’t rejections—they’re opportunities. Josh encourages business owners to run toward objections rather than shy away from them.
For example, when people tell him, “I’ve tried going to conferences, and they’re a waste of time,” he doesn’t dismiss their frustration. Instead, he asks:
“What is it about the conference that isn't working for you?”
By listening to objections, businesses can refine their messaging, reposition their offerings, and ultimately, convert more leads into clients.
How to Generate Leads on Repeat
Josh has helped over 90 education companies develop repeatable lead generation strategies. His Raise Your Hand campaign is one of his key tactics for identifying high-quality leads.
Step 1: Identify Your Ideal Client
Most businesses think they know their ideal client, but they haven’t gone deep enough. Josh recommends asking:
- Who do you want to work with most?
- What are their biggest challenges?
- What transformation does your product or service provide?
If your messaging isn’t resonating, you may not be targeting the right people.
Step 2: Build Credibility as a Subject Matter Expert
People buy from those they trust. And trust is built through credibility.
Josh emphasizes that credibility is not just listing accomplishments—it’s about showing up as an expert.
“Your LinkedIn profile shouldn’t be a résumé—it should be a sales funnel.”
This means:
- Posting valuable content that speaks to your ideal client’s pain points
- Sharing case studies, testimonials, and proof of results
- Positioning yourself as an authority in your space
Step 3: Master Messaging That Converts
No matter how great your product or service is, if your messaging isn’t clear, people won’t buy.
Josh’s process focuses heavily on refining messaging to increase response rates. His clients send 600-800 cold emails per week with a 30% open rate and a 10% reply rate—far above industry averages.
The key? Crafting messaging that speaks directly to what the client cares about most.
Step 4: Automate & Scale Once the System Works
Too many businesses try to automate their lead generation before they’ve fine-tuned their messaging.
“You don’t pour gasoline on a fire until you know the fire is already burning.”
Josh advises businesses to first test and optimize their sales process, then scale with automation tools and outreach strategies.
Final Takeaways: The Power of Learning from Mistakes
Josh’s story is a powerful reminder that mistakes—no matter how costly—are also opportunities for growth.
From choosing the wrong business partners to refining his sales process, his experiences have shaped the way he now helps businesses avoid those same pitfalls.
His biggest advice?
- Test relationships before committing to partnerships.
- Focus on one clear offer.
- Embrace objections and use them to refine your business.
- Build credibility through content and positioning.
- Generate leads on repeat, not just one at a time.
Whether you're an entrepreneur, startup founder, or business owner, these lessons can help you navigate challenges more strategically—and turn mistakes into stepping stones for success.
Want to Learn More?
Connect with Josh Chernikoff on LinkedIn or visit JoshChernikoff.com to learn more about his Ed Sales Elevation Experience and his approach to lead generation.