Get Out of the Kindergarten Stage in Business
8 Dec 2025 · 6 min
This podcast episode (Den Lennie) addresses established video business owners stuck in the "kindergarten stage"—the disorienting transition from craft to business ownership. Lennie explains that the feeling of being lost is normal, highlights isolation as a key problem, and prescribes three practical moves (a visible pipeline, one clear offer for a defined client type, and a simple follow-up system) plus a 90-day marketing rhythm. The episode stresses community, consistent imperfect action, and focusing on bringing in work rather than perfection.
Chapters
G', day, guys. You're listening to the Den Lenny show, the podcast for established video business owners who want to scale smarter, not harder. We talk strategy, systems, and the scale method that turns busy founders into strategic CEOs.
Look, you're really good at what you do. Clients love working with you. But the moment you started really building your business, you probably went from knowing exactly what you were doing to. To feeling completely lost. And here's what nobody tells you. That feeling of being out of your depth, it isn't a sign you're screwing up. It's a sign you're in transition. And understanding this one thing will change everything about how you approach the next 90 days. I'm Dan Lenny, and today we're talking about the kindergarten stage of building a video business and why almost everyone gets stuck here when way longer than they need to.
I had this conversation just this week with one of our guys. Really talented filmmaker, been doing it a long time. He has a solid reputation and his clients love him and he wanted to build the business beyond himself. And he said something that really stuck with me. He said, dan, I feel like I've got so much to do. It all looks kind of big and scary and I just don't know what. Where to start. And this is someone who can walk onto any set in any country in the world and know exactly what needs to happen. But marketing, systems, sales, Suddenly he's back at the beginning. After working with hundreds of video business owners, I can tell you this is the most predictable thing we see. And the companies that break through aren't necessarily smarter or even more talented. They just get three things about this transition that. That most people miss. Today I'm breaking down exactly what the kindergarten stage is, why it hits hardest when you're already good at your craft, and what actually gets you through it faster. Here's the really tough part. The better you are at your craft, the harder this transition feels. Think about it. You've spent years getting really good at.
Making films for clients.
You take pride in knowing what you're doing. You deliver great work. That's who you are. Then you step into this business ownership thing and suddenly you're dealing with cash flow anxiety, marketing that doesn't seem to work, sales, conversations that feel weird and awkward, and systems you just don't understand. Nothing feels natural or familiar anymore. One of our guys in the VBA put it perfectly this week. He said, My old LinkedIn posts are all grateful for the opportunity and boring as hell. And now my AI writer sounds just like. Because that's what I trained it on. I realize I need to update it and change the conversation. Most people think this means they're not cut out for business. Wrong. This just means you're in transition and every single business owner I know who's doing well has been exactly where you are right now. The difference? They didn't wait until they felt ready. They got comfortable with being uncomfortable and just kept moving. Let me tell you what I learned recently that completely changed how I think about what we do. I sat down with four of our most successful guys. I asked them what our coaching really does for them. I thought they'd talk about revenue or systems or scaling. But you know what they all said completely separately, in isolation, in four different interviews. Community not being on your own. Having somewhere to go when they're stuck. The problem I thought we were solving was how do you get to half a million a year? That's actually just what happens as a result. The real problem is isolation. Making 100 decisions every single day with nobody to talk it through with. Wondering if what you're going through is normal or if you're completely off track. Here's what this means for you. The kindergarten stage isn't about learning marketing tactics or building the perfect website. It's about building the muscle of making business decisions when you don't yet have all the answers. You're not looking for perfection. You're building confidence through taking action, even when it's not perfect. I made a video about this recently and it's the single most important thing to understand about marketing your video business. There's a 90 day lag between when you start marketing and when you see the money coming in. Think about what that means. If you're quiet in November because you're busy shooting, you're setting up a problem for February. If you stop reaching out because your pipeline looks good today, you're creating a cash flow gap three months from now. This is why the companies doing well never stop marketing. Not because they love marketing, but rather because they understand the timeline. One of our guys in the VB had this exact realization this week. He said, I'm just going to chase this every lead and opportunity and I've got to chase it hard until December 23rd. That's the mindset. Not when you feel like it. Not when things are suddenly quiet. Always the companies that survive and scale are the ones that get this 90 day rhythm and plan around it. Let me be really specific about what gets you out of this kindergarten stage. First, you need a pipeline. You can actually see not opportunities floating around in your head. Not I should probably follow up with that person. An actual visual where you can look and say I've got 15 conversations going, three quotes out and five people I need to follow up with today. Second, you need one clear offer for one clear type of client. Not we do video production.
That's too vague.
Pick something. One of our guys just went all in on childcare centers. Another does logistics companies. Another just quoted a two day conference livestream for ten grand because that's his thing. Third, you need a follow up system that removes the guesswork. I'm not talking about complicated automation. I'm talking about knowing exactly who you're supposed to contact today and what you're going to say. Notice what's not on this list. Your website. Being perfect, having a nice office, buying expensive tools. Those things might make you feel more legit, but they won't bring in work. Here's what I told one of our guys this week and I want you to hear this. The frustration you're feeling is because you want your business to look as polished as your work. You want to show the world something you're proud of. And right now it's just not there yet. That's not a problem. That's exactly where you're supposed to be. Nobody's paying that much attention to your website or to your LinkedIn or whether everything looks perfect. They care about whether you can help them solve their problem. Your job right now isn't to build the perfect business. It's to bring in work, deliver great results, and learn the business side through actually doing it. The kindergarten stage ends when you stop trying to figure everything out before you start and instead figure things out by doing them. So here's what I want you to take away from this. If you're feeling overwhelmed all over the place, or like you've gone from knowing what you're doing to being completely lost, that's not failure, that's transition. And it's exactly where building a real business starts. The companies that break through aren't the ones with the best gear or the nicest websites. They're the ones who get comfortable being uncomfortable, focus on one clear thing and take consistent action even when they don't have all the answers. You already know how to be really good at your craft. Now you're learning how to be good at business. And just like with your creative work, that happens through doing it, not through waiting until you feel ready. So which part of the kindergarten stage are you stuck at right now? Is it the overwhelm of too many options? Feeling uncomfortable because you don't know what to do next? Or is it just the grind of consistent follow up when nothing's showing up yet? If you're watching this, drop a comment and let me know. I read every single one and your answer might just become next week's video. If you want to see how production companies like yours are breaking past 500k without burning out, I've put together a private briefing that shows the exact four shifts we've seen work across 178 plus companies. It's free. Grab it@denleny.com authority gap and if this helped you realize you're not the only one going through this. Subscribe and tell your friends so you don't miss future episodes.
This is the Denleny Show. If you've built a solid production business but feel stuck in the grind, it's time to think bigger. Over the past 14 years, I've helped 178 companies generate more than 52 million in documented growth using the Scale method and our elite mastermind. If you want to create predictable pipelines, attract higher value clients, and finally buy back your time, head to denleny.com that's where the next level begins.
More from Den
BFC #007 - How to go from being a Freelance Video Curator to an Agency Owner with Doug Suiter