Best Josh Chernikoff Podcasts (2025)

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Hesitation Is a $250K Mistake: Dr. Tamara Minott on How Education Founders Close Deals With Confidence 26:42

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2h ago26:42

26:42

Most education founders don’t lose deals because their product isn’t good enough. They lose them because they hesitate, overthinking the pitch, second-guessing decisions, and waiting for “perfect” when progress is all they need. That hesitation kills more deals than rejection ever will. And if you’ve ever felt imposter syndrome creeping in before a…

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You Crushed the Demo—But Still Can’t Close: The $100K Mistake Education Founders Keep Making 18:58

5d ago18:58

18:58

You crushed the demo. The buyer smiled. They nodded. They even said, “This is exactly what we need.” And then… nothing. That silence isn’t harmless. Every “We’ll be in touch” costs you weeks of follow-up, lost momentum, and deals that should already be on your books. In Part 1, “Your Demo Is the Problem” with John Gamba, Entrepreneur in Residence a…

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From Betrayal and Courtroom Battles to Closed Deals: Robespierre Reyes on Rebuilding Credibility, Team Alignment, and Education Deals That Close 19:05

12d ago19:05

19:05

Robespierre Reyes had funding, traction, and a winning idea. Then came the lawsuits, burnout, and partners who betrayed him. Four companies, three failures, one courtroom showdown. His confidence, credibility, and pipeline of leads were all at risk. Most founders would quit. Rob didn’t. Instead, he rebuilt everything that actually drives qualified …

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From Confusion to Clarity: JD Mosley-Matchett on the Message Shift That Turns Unclear Offers into Scalable, Trust-Building Growth for Education Founders 18:36

19d ago18:36

18:36

Most education founders and EdTech leaders think their problem is marketing. But sometimes, the real issue is something more critical: Clarity If your message isn’t clear, your market stops listening, no matter how brilliant your solution is. That was the hard truth J.D. Mosley-Matchett, PhD had to face. As the Founder & CEO of InforMaven.AI, JD’s …

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The Mindset Reset: Mitch Weisburgh On How Education Founders Can Master Mindset, Beat Burnout, and Close Strong Deals 36:54

26d ago36:54

36:54

You’ve got the product, the drive, and the skills, but when pressure hits, your mindset starts to crack. Suddenly, deals stall, momentum fades, and even your warmest prospects go quiet. The harder you push, the less it seems to move forward. Most education founders panic. They double down on demos, CRMs, late nights, and new pitches, thinking more …

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Stop Delegating Sales: Why Education Founders Must Sell Their Solution First Or Watch Their Pipeline Die 14:05

1M ago14:05

14:05

Most education founders think the next rep, agency, or AI tool will solve their sales problem. It won’t. Here’s the truth: if you can’t sell your own offer clearly, no one else can. Every lead you hand off too early is wasted time, lost money, and a pipeline headed for collapse. Every day you delay founder-led sales is another day your growth stall…

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From Lost Leads to Locked Contracts: Paul King on Niche Focus, Pilots That Convert, and Closing Education Deals 32:38

1M ago32:38

32:38

What happens when you stop trying to serve every school and start solving one urgent problem for the right schools? It’s the positioning shift most founders resist—but it’s the exact move that transforms “just another vendor” into a mission-critical partner. That’s why this episode of Breaking the Grade is essential listening: Josh sits down with P…

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The Education Founder’s Blueprint: Kevin Chavous on Turning Setbacks Into Proof Points, Credibility, and Growth That Lasts 47:41

2M ago47:41

47:41

Most education founders think buyers want the perfect pitch, the flashy product, or the right political connection. But Kevin Chavous—national education reformer, bestselling author, and President of Stride, Inc. proves that none of those close deals. What does? Credibility, proof, and persistence. This episode is extra special because Kevin was th…

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The Guarantee Shift: Karim Kuperhause on How Education Founders Build Trust and Win Qualified Leads Without Sounding Desperate 44:59

2M ago44:59

44:59

What happens when a superintendent or a higher ed leader—looks you in the eye and asks: “What happens if this doesn’t work?” For most education founders, that’s the deal-killer moment. They freeze. They dodge. They hide behind buzzwords. And the buyer walks away unconvinced. But here’s the truth: In today’s market, whether it’s K–12 districts or hi…

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From Invisible to Irresistible: Michael Campbell on Using Research and Proof to Build Trust, Generate Leads, and Drive Education Growth 28:31

2M ago28:31

28:31

Every education founder, EdTech CEO, and school leader wants growth. But here’s the mistake almost everyone makes: they chase revenue before they’ve earned trust. In education, trust is the real currency—it turns a pitch into a meeting, and a meeting into a deal. In this episode, I’m joined by Michael Campbell, president of Advancing Global EDU, In…

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$9M Raised, Zero Guesswork: How YourWay Raised $9M by Solving the Lead Gen Problem Most Education Founders Ignore 27:14

2M ago27:14

27:14

Most education founders don’t fail because of bad ideas. They fail because they lean too hard on “AI-powered” buzzwords, skip the research-to-practice proof buyers demand, and don’t form the partnerships that give them credibility and attract the right leads. That’s the cycle YourWay Learning set out to break. Back in January, at the IFE Conference…

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From “Great Pitch” to Signed Contract: Paul Vallas on the Buyer’s Lens That Closes Education Deals 23:56

3M ago23:56

23:56

What happens when you finally land the big meeting… and walk out with nothing but “We’ll think about it”? It’s the growth killer most founders don’t see coming—your pitch isn’t aligned with how education buyers actually make decisions. That’s why this live Breaking the Grade episode from ASU-GSV (the edtech conference each April in sunny San Diego)…

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(Re-Air) The Signature Solution: Your Proven Blueprint to a Clear Offer That Generates Leads and Wins the Education Market 17:08

3M ago17:08

17:08

What if your biggest lead gen problem isn’t visibility — but the fact that your offer isn’t clear enough to close? Most EdTech founders think they have a marketing problem. Some think it’s a sales problem. But what they actually have is this: ❌ An offer that’s vague ❌ A proven model that’s undefined ❌ And no document that makes buyers say “yes” on …

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From $10M in Sales to Losing Her Company: What Education Founders Learn the Hard Way About Selling, Scaling, and Staying Aligned 26:12

3M ago26:12

26:12

Most founders think their growth problem is sales. But Jolene Levin, entrepreneur, innovator and founder of NorvaNivel proved it’s the other way around: your sales reveal your growth problem. Jolene founded a classroom furniture company in Australia, scaled it across schools, and then brought it to the U.S. Three months after launching in the U.S.,…

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(Best of) Your Demo Is the Problem: What Education Founders Must Do—and Stop Doing—to Close More Deals With Their Demos 35:20

3M ago35:20

35:20

Most EdTech demos fall flat because they focus on product—not pain. They walk through features—but skip the funding strategy. They sound polished—but feel disconnected. And when the call ends? No buy-in. No follow-up. No deal. That’s where John Gamba changes the game. John isn’t just an expert in EdTech innovation—he’s coached thousands of educatio…

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From Collapse to Credibility: Robert Martellacci’s Blueprint to Win Back Influence and Close Deals in the Education Space 33:37

3M ago33:37

33:37

What happens when your billion-dollar success story ends—and the market forgets your name? Robert Martellacci knows. And he didn’t quit—he reinvented. This episode isn’t just about resilience. It’s about the bold mindset shift it takes to reclaim relevance, rebuild trust, and restart traction when everything you built gets wiped off the board. Robe…

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From Dead-End to C-Suite: An Edtech’s Messaging Framework That Converts Education Conversations into Contracts 15:33

4M ago15:33

15:33

Here's the Messaging Fix You Didn’t Know You Needed If your EdTech offer sounds “nice” but never gets past your perfect client to respond… this episode is your wake-up call. Carlos Zapata, founder of Unicorn Academy, joins me live from the IFE Conference in Monterrey, Mexico — and pulls back the curtain on the exact moment his company stopped stall…

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Your Summer Fix: How Education Founders Can Rebuild Lead Flow Before Back-to-School 14:38

4M ago14:38

14:38

Let’s get one thing straight: September doesn’t start in September. It starts now—in June, July, and August. Because the biggest mistake founders make in summer isn’t taking a break. It’s confusing rest with silence. You can recharge and still generate leads. But most EdTech founders go dark. They hunker down. Rebuild ops. Tweak product. And comple…

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From Quiet Posts to Real Revenue: How Anissa Used LinkedIn to Build Trust and Attract Qualified Leads 41:07

4M ago41:07

41:07

Most EdTech founders are still chasing views. Anissa Bouderraoui is closing pilots. She didn’t wait to go viral. She showed up consistently—with clarity, credibility, and the kind of messaging school leaders actually respond to. The result? No gimmicks. No funnels. Just a pipeline built on trust. Bolstered by LinkedIn consistency. 🎯 When Anissa sta…

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The Rest Advantage: How Education Founders Use Strategic Pauses to Spark Lead Gen Breakthroughs 14:31

5M ago14:31

14:31

Most education founders treat traction like a treadmill. When the leads slow down, they don’t stop to ask why—they sprint faster. More posts. More emails. More calls. More grind. But here’s what most founders miss: 📉 Motion ≠ Momentum 📉 Hustle ≠ Clarity 📉 Activity ≠ Conversion In this episode, Josh goes solo to unpack a hidden truth in EdTech sales…

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Clearer Messaging, Consistent Leads: What EdTech Founders Can Learn from MindShifting 36:11

5M ago36:11

36:11

Most education companies don’t lose leads because their product is weak. They lose them because the message doesn’t land. They try to sound professional. Strategic. Smart. But polish ≠ presence. And clever ≠ clear. In this episode, Josh sits down with Mitch Weisburgh—a lifelong educator, EdTech veteran, and founder of MindShifting with Mitch—to unp…

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Do the Opposite of Everything You’ve Been Doing: How Seinfeld’s George Costanza Unlocks Lead Gen Clarity for EdTech Founders 17:42

5M ago17:42

17:42

Let’s start with a sitcom—and a truth bomb. In Seinfeld Season 5, Episode 22 ("The Opposite"), George Costanza hits rock bottom. No job. No love life. No confidence. So he flips the script. “If every instinct I have is wrong, then the opposite must be right.” And suddenly? He orders chicken salad instead of tuna. He tells the girl he’s unemployed a…

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Breaking Borders: How Smart EdTech Founders Build Scalable Companies Without Losing Local Trust 33:06

5M ago33:06

33:06

If you’re trying to grow your education business beyond where you started—this episode is for you. Because whether you’re moving from one country to another, or just one state to the next… The real challenge isn’t translation. It’s trust. In this episode of Breaking the Grade, I sit down with Denise Abulafia—EdTech founder, Penn GSE professor, and …

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The Speaking Strategy: How Education Founders Fast-Track Credibility, Confidence, and Sales Momentum 20:34

5M ago20:34

20:34

LinkedIn builds your credibility — Speaking amplifies it. In this episode of Breaking the Grade, I’m sharing how I went from avoiding stages entirely to speaking at in the last 13 months at Penn GSE, the University of Chicago, SXSW EDU, DC Startup Week, Education Research and Development Institute, XEdu, Institute for the Future of Education in Mex…

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From Ghosted to Booked: How Ashton Tate Filled His Calendar with Qualified School Leads 26:03

6M ago26:03

26:03

You’re not afraid of hard work. You’ve put in the hours. You’ve sent the emails. You’ve done the demos. And still—no one’s biting. That was Ashton Tate. Founder of The Form Curriculum. Fitness coach-turned-EdTech founder. 500 cold calls deep… and still stuck. Then he changed one thing. He stopped selling—and started listening. In this episode of Br…

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You Don’t Just Sell to Schools—You Earn Their Trust: How Edtech Founder Paul Moch Built an Education Business That Got Acquired 20:53

6M ago20:53

20:53

You think your sales process is tough? Try launching a brand new EdTech company during a global pandemic—while building trust with schools that aren’t exactly raising their hands. In this episode of Breaking the Grade, I sat down with Paul Moch, Founder of Camino 21 and now Vice Provost at Talisis, to break down what it really takes to build a scal…

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Busy Isn’t Booked: The Silent Sales Mistake Most Founders Miss 20:29

7M ago20:29

20:29

You’re busy. But you’re not booked. You’re showing up on LinkedIn. You’re attending conferences. You’re tweaking your SEO. You’re following the playbook everyone told you to run. And still—your pipeline’s empty. In this episode of Breaking the Grade, Josh Chernikoff breaks down the silent mistake most education founders don’t realize they’re making…

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Cracking the Code: How to Sell Education Products in High-Stakes Markets 22:03

7M ago22:03

22:03

Recorded live at IFE in Monterrey, Mexico, this episode features Beatriz Guillen, Executive Director at The Resource Foundation—a leader focused on strengthening education outcomes across Latin America. While her work centers on Latin America, the insights she shares here resonate globally—especially for education companies and founders navigating …

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From Chaos to Clarity: How One Founder Rebuilt His EdTech Biz from the Ground Up to Revenue Way Up 30:37

7M ago30:37

30:37

Too many education founders build something incredible—only to realize they can’t sell it. They try to figure it out themselves… piecing together advice from free webinars, Twitter threads, and late-night YouTube binges. But without a proven system, the growth stalls—and burnout creeps in. In this episode of Breaking the Grade, I sit down with Nick…

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Why Most Education Companies Burn Out Before They Scale—And the Fix That Actually Works 25:17

7M ago25:17

25:17

You’ve got the vision. The team. The momentum. So why does it feel like you’re sprinting on a treadmill with no finish line in sight? Here’s the truth: Most education companies don’t burn out because of a bad idea. They burn out because they’re trying to scale without a system. In this live episode of Breaking the Grade, recorded at IFE 2025 in Mon…

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LinkedIn Connection to Contract: Josh's Proven Six-Step EdSales Method (No Paid Ads/Funnels/Cold Calls) 21:10

8M ago21:10

21:10

You’ve added decision-makers on LinkedIn. You’ve liked a few posts, maybe even commented. You’re showing up… but nothing’s turning into a call, let alone a contract. Sound familiar? That’s what I call the LinkedIn illusion—where activity feels like progress, but the results just aren’t showing up in your pipeline. Here’s the truth: If you're an edu…

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Struggling to Sell to Schools or Universities? (An Expert in HigherEd Tells You How to do it Right) 20:32

8M ago20:32

20:32

Selling into education institutions—whether K–12 or higher ed—isn’t just about having a great product. It’s about understanding how those institutions work: how decisions are made, what roadblocks slow things down, and how to position yourself as a trusted partner—not just another vendor. In this special live episode recorded at IFE in Monterrey, M…

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The Conference Playbook: How Education Companies Get Conferences Wrong (And How to Fix It) 29:53

8M ago29:53

29:53

Does this sound familiar? You just spent thousands of dollars flying to ANOTHER education conference, setting up a booth, shaking hands with decision-makers. You collected a stack of business cards, had great conversations, and walked away thinking, this was a success. Two weeks later? It was the kiss of death for their conference strategy—no follo…

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IFE Conference 2025 (Mexico): Breaking Barriers -- AI and Strategic Partnerships Shaping Education 26:18

8M ago26:18

26:18

The education sector is buzzing with AI, but are schools and EdTech businesses truly leveraging it for sustainable growth? In this live episode, we cut through the hype to explore how AI, combined with strategic partnerships, can drive real impact. In this special live episode of Breaking the Grade, recorded LIVE from the IFE Conference in Monterre…

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Why Most Startups Get Investment Wrong—and How to Fix It 21:07

9M ago21:07

21:07

Summary When you're growing your education business, one big question always comes up—should you seek investment or bootstrap your way to success? In this episode, Josh Chernikoff breaks down the real challenges behind this decision. He shares lessons from his own journey, the mistakes founders make when chasing investment too soon, and what it rea…

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Before You Hire a Sales Team...The Steps Founders Can’t Skip 18:33

10M ago18:33

18:33

Summary In this episode of Breaking the Grade, Josh Chernikoff tackles the big question: when’s the right time to bring on a sales team for your education-focused business? He shares why rushing to hire too soon can be a mistake and what you need to do first to make sure you're ready. Josh opens up about his own experiences, talking founder-led sal…

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Secrets behind unlocking 7-figures in sales...How this seasoned entrepreneur transformed his sales process. 26:23

10M ago26:23

26:23

Summary In this episode of Breaking the Grade, I chat with Ernie, a seasoned leader who's been navigating the ever-changing education landscape since 2001. He shares valuable insights on how he completely transformed his sales system and unlocked 7-figures in proposals before the new school year started. Ernie shares all about staying adaptable, bu…

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From One-Off Sales to Repeatable Revenue...How Future Makers Transformed Their Business 34:49

11M ago34:49

34:49

Summary Nine years of building a business—and then, overnight, everything changes. Suddenly, you’re scrambling to keep things afloat, unsure of your next move. That’s exactly what happened to Matt Barinholtz, founder of Future Makers. When the pandemic hit in 2020, he had to pivot fast—shifting from offering services to selling products. The truth …

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Mastering Sales Planning in the Education Space 31:29

11M ago31:29

31:29

Summary: In this episode of Breaking the Grade, Josh Chernikoff and Toni McMurray tackle the challenges of sales planning for education companies as the new year approaches. If you’re feeling overwhelmed by the tight sales window or struggling with staying top of mind with prospects, this episode is for you. We discuss the impact of inconsistent ou…

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Mastering the Education Sales Cycle & Secrets to Staying Top of Mind and Closing Deals 18:07

12M ago18:07

18:07

Summary: Sales in the education space can feel like an endless maze—long cycles, multiple decision-makers, and constant resistance. In this episode, Josh Chernikoff pulls back the curtain on the challenges EdTech founders face when selling to schools and districts. It’s not just about getting through the door; it’s about navigating complex decision…

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Why Waiting to Sell in the Education Sector Can Cost You...& when’s the right time to start selling 17:30

1y ago17:30

17:30

Summary: Wondering when you should really start selling in the education market? In this episode, Josh Chernikoff dives into the right timing and approach for effective sales in the education space. Spoiler: it’s not just about waiting until you have a perfect offer. It’s about understanding the specific buying cycles and decision-making processes …

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A Better Approach to Sales Calls for Education Companies… How to sell without being salesy. 19:31

1y ago19:31

19:31

Summary: Are your sales calls feeling like one-way pitches instead of real conversations? In this episode, Josh Chernikoff uncovers a simple yet powerful shift that could change how you approach every sales call moving forward. Spoiler: it’s not about selling harder or pushing your offer more aggressively. It’s about tapping into a skill most sales…

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The Better Demo Method To Sell More Education Services & Products 31:45

1y ago31:45

31:45

Summary: Selling to schools and districts is more than just having a good product—it’s about really understanding the specific challenges and needs of the education market. In this episode, Special Guest: John Gamba (Entrepreneur in Residence at the University of Pennsylvania Graduate School of Education) and I talk about how to deliver better sale…

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How This EdTech Company Transformed Their Sales Process And Went From Stagnation to Leads In Just 8 Weeks 31:07

1y ago31:07

31:07

Join me as I sit down with Chris and Corey from Rocket PD to talk about how they revamped their entire sales process to feel more natural and focused on building relationships with their ideal customers. Chris and Cory have years of SaaS experience under their belt and they know a lot about marketing and selling software, but selling to schools fel…

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How this EdTech Startup sharpened their message & went from struggling to selling! 23:33

1y ago23:33

23:33

Summary Imagine a tool that could revolutionize how students manage their homework—built not by some big tech company, but by a parent and a 12-year-old visionary. Curious? In this episode, we're diving into a startup story that's as unique as it gets. A co-founder whose biggest challenge wasn’t just building the tech but navigating the labyrinth o…

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How this EdTech founder got clarity on his ideal client & product... making selling easier! 26:29

1y ago26:29

26:29

Summary: Starting a business with the goal of solving complex educational problems is a tall order. But Sam Saarinen, founder and CEO of Edapt Technologies, embraced this challenge head-on. In this episode, Sam shares his entrepreneurial journey—one marked by ambitious starts, hard-learned lessons, and a game-changing pivot that led to remarkable b…

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3 Powerful Systems To Grow Your Education Business With More Ease 26:57

1+ y ago26:57

26:57

In this episode, Josh Chernikoff discusses the importance of implementing systems in order to scale and grow an education business. He highlights three powerful systems: offer system, lead generation and sales system, and delivery system. He emphasizes the need for a repeatable and scalable offer, a lead generation system to attract and nurture ide…

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3 Essentials To Grow Your Business: Lessons I Learned From Starting, Scaling, and Selling Flex Academies 21:29

1+ y ago21:29

21:29

In this episode, Josh Chernikoff shares his experiences and challenges in growing his second business, Flex Academies. He discusses the importance of finding the ideal client, pivoting the business model, and building a strong offer. He also emphasizes the need for a lead generation system and the importance of surrounding oneself with experts. Jos…

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Kathryn’s Lead Generation Transformation with the EdSales Elevation Experience 27:53

1+ y ago27:53

27:53

In this conversation, Josh Chernikoff interviews Kathryn Adabonyan, the founder and CEO of Go Pursue, a company that helps high school students explore career options and connect with professionals in those fields. They delve into Kathryn's journey as an entrepreneur, a testament to her resilience in overcoming sales and marketing challenges. Kathr…

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How to Build A Lead Generation System in 9 Steps 31:45

1+ y ago31:45

31:45

In this conversation, Josh Chernikoff discusses his nine-step process for building lead generation machines that produce high-quality and high-converting leads on repeat. He addresses the common challenge of not knowing how to get leads and emphasizes the importance of founder-led sales. Josh shares his own experience of starting a tutoring busines…