by Josh Chernikoff
One question I often get from founders, especially those new to the education space, is: “When’s the right time to start selling?” Many people hesitate to start selling, convinced that they need everything to be perfect first. But waiting for perfection can lead to endless delays—and worse, it can sink a great idea before it ever gets off the ground. And that is why my answer to that question is always right now! It is never too early to start generating new leads and start selling.
As a new entrepreneur, you might feel like every single piece has to be perfectly in place before launching. It’s easy to think, “How can I sell if my product isn’t complete?” But if you keep holding off, “perfect” might take years, and by that point, you might miss the market entirely. Let’s break down why starting sooner rather than later is so crucial, how to get feedback before things are polished, and why aiming for perfection might actually be the biggest roadblock to success.
The Vasa Ship Lesson: Why Waiting for Perfect Can Sink Your Success
A story I like to use as an example for education entrepreneurs stuck in this mode, is the story of the Vasa. I use this story because it perfectly illustrates what happens when we get too caught up in perfection.
In the early 1600s, Sweden’s King Gustavus Adolphus commissioned the most powerful warship ever, the Vasa. He wanted something that would dominate the seas, so he kept making adjustments. Extra cannons, taller masts, intricate carvings—the goal was to make the Vasa an unstoppable force. But with each addition, the ship became heavier, and the design more complicated, causing delay after delay.
Finally, after years of adjustments and tweaks, the Vasa was ready to set sail. It looked incredible from the outside, but within minutes of launching, it tipped over and sank. All those last-minute improvements couldn’t save it from a fundamental flaw that might have been discovered if they had simply tested it sooner.
For entrepreneurs, especially those creating something for the first time, Vasa's story is a reminder not to get caught up in perfectionism. It’s easy to think you need everything to be flawless before putting your product out there. You might worry, “Who’s going to buy this if it’s not perfect?” But waiting for perfection often leads to missed opportunities and valuable time lost.
The truth is that selling doesn’t require a perfect product—it just requires something real and useful that you can build upon. Launching early gives you an opportunity to gather feedback, learn what works, and improve along the way. Each step forward brings you closer to a stronger product than endless tweaks behind the scenes ever could.
So take the first step—launch, listen, and learn. The Vasa story is a great reminder that tweaking things endlessly without actually testing them in the real world can stop your business from ever taking off. Instead, focus on growing and being flexible as you go!
So, how do you avoid the Vasa trap and get started? By launching with a Minimum Viable Product (MVP).
Launching with a Minimum Viable Product (MVP)
Instead of spending years trying to create the perfect product, start by launching something simple. A lot of founders get bogged down waiting until they’ve built out every possible feature, but the MVP (Minimum Viable Product) approach flips this thinking on its head.
With an MVP, you put a basic version of your product in front of real users and start gathering feedback right away. This way, you’re solving one main problem really well, and anything extra can come later—ideally, based on what your users actually want.
By starting small, you lower your risks and start learning from your audience sooner rather than later. This lets you adapt based on real needs rather than guesses, leading to a much stronger, more refined product over time.
So, the sooner you launch, the sooner you can start improving and one of the most powerful ways to start selling without feeling salesy is the Raise Your Hand Approach.
Engaging Without Being “Salesy”: ‘Raise Your Hand’
The “raise your hand” approach is all about opening a conversation without the pressure of a hard sell. Imagine sitting in a room full of people all trying to get noticed—it’s loud and overwhelming. But then someone quietly raises their hand, inviting attention without demanding it. This approach in sales works the same way: instead of pushing your solution, you make it clear that you’re there to listen, understand their challenges, and help when they’re ready.
Why does this work so well? People respond best when they have a choice. By simply offering to engage, you create an environment where your prospects feel seen and respected rather than pressured. Sharing insights, asking questions, or providing a helpful tip shows you’re genuinely invested in solving their problems, not just selling.
This method builds trust, making you more than just a vendor—they see you as a partner who gets their world. By “raising your hand,” you let clients come to you naturally, creating genuine connections that lead to long-term relationships and a much smoother sales process. Now, even though the 'raise your hand' approach is a great way to start genuine conversations, just like any tool, it only works if you actually use it. And let’s be real—it won’t always be smooth sailing. There will be times when you face rejection, or when things don’t go exactly as planned.
But just like my 10-year-old daughter Camilla at the skatepark, the key is to keep trying.
Taking the Leap: Lessons from Skateboarding
Watching my daughter Camilla at the skatepark is like a live lesson in resilience and taking risks. She and her friends are all about mastering new tricks, and falling is part of it. They don’t care about the mistakes—they’re just determined to keep going until they get it right.
Selling is no different. Especially in the beginning, you’re going to hear “no” a lot, and it’s going to feel uncomfortable. But those “nos” are actually good—they help you learn what works, what doesn’t, and where you need to adapt. The confidence to sell doesn’t come from having the perfect pitch. It comes from putting yourself out there, learning, and listening to what your audience is really after.
So, don’t wait for the perfect moment to make your first move. Every stumble, every 'no' is part of the process that brings you closer to understanding what your audience truly needs.
And speaking of timing, one thing I often hear from education entrepreneurs is how tough it is to navigate the seasonality of the market.
Navigating Seasonal Selling in Education
The education market runs on its own schedule, so timing is everything. Schools’ buying patterns follow the academic calendar, budget cycles, and specific decision-making windows. Knowing when schools are most open to conversations can make all the difference.
Spring and summer are key times for budget planning, making them ideal for connecting with schools and districts as they prepare for the next academic year.
On the flip side, testing periods and back-to-school months are packed. Reaching out heavily during these times often won’t get much traction since educators are fully booked.
Mid-year, around December and January, can be another great opportunity, as schools reassess their progress and start looking for solutions to carry them through the rest of the year.
Education sales cycles are typically long, with multiple touchpoints needed. Staying active all year helps keep you top of mind, so you’re ready when they’re ready. By understanding these cycles, you can connect with the right people at the right time and keep your outreach feeling timely and relevant.
That said, even though education has its seasons, it doesn’t mean you should only be selling during specific windows. You still need to stay active and nurture your relationships year-round. By doing that, when the timing is right, your prospects will already be familiar with you and your product.
Always Be Selling: Consistency Is Key
One of the biggest pitfalls in sales is letting your pipeline dry up between contracts. You close a deal, dive into delivering on it, and then suddenly realize you’ve got nothing lined up for when the project ends. To keep your pipeline full, you need to keep selling—even when you’re busy.
The key? Build a simple routine for reaching out to new leads, even in the middle of client work. Selling is like a muscle: the more you use it, the stronger it gets. By weaving selling into your weekly routine, you make sure you’re not scrambling for opportunities when a contract wraps up.
Summary:
Start Selling Now: Don’t wait for everything to be perfect; launch your product or service to gather valuable feedback early.
Learn from the Vasa Ship: Avoid the pitfalls of perfectionism by testing and iterating your offering rather than delaying for endless adjustments.
Embrace Resilience: Understand that rejection is part of the process; learn and improve with every “no” you encounter.
Engage Genuinely: Use the “raise your hand” approach to create meaningful conversations that address prospects’ pain points without feeling pushy.
Launch with an MVP: Focus on delivering a Minimum Viable Product that solves a key problem, allowing you to gather insights for future improvements.
Understand Seasonal Cycles: Be aware of the academic calendar and timing your outreach to align with schools' budgeting and decision-making windows.
Maintain Consistency: Keep your sales efforts active between contracts to ensure a steady pipeline and avoid scrambling for new leads.
Conclusion
Ready to Sell? Start Now
So, when’s the right time to start selling? Right now. Every interaction, every conversation is a chance to build a relationship that could lead to something down the line. Selling isn’t just about closing deals—it’s about creating connections, building trust, and growing step by step.
Don’t wait for perfection. Get out there, put yourself in front of potential customers, and start conversations. Every “no” is one step closer to a “yes,” and each connection brings you closer to building the business you’re envisioning. Embrace the process, adapt, and watch what happens when you go all in, right from the start.