Your First Deal Will Feel Awkward – Do It Anyway
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Your First Deal Will Feel Awkward – Do It Anyway

Your first deal as a bootstrapped entrepreneur? Don’t expect it to go smooth as butter—it’ll probably feel more like an uphill climb. Your first pitch, the first call, your first Heads of Terms—they’ll all feel daunting, but here’s the thing: that’s normal. Most entrepreneurs make mistakes their first time, and it’s all part of the learning curve. Let’s dive into why getting comfortable with discomfort is the key to getting that first deal done and how a community of fellow Indiemakers can help you navigate every step. 

Indiemaker Team

By Indiemaker Team

Your first business deal won’t be clean, polished, or easy – and that’s precisely how it’s supposed to be. If you’ve just picked up your first deal, buckle up – you’re in for a ride! You’re excited. Nervous. Maybe even overwhelmed. That first call, pitch, and negotiation feels like a crash course in a language you’re only just starting to learn. But here’s the truth: you’re not failing – you’re just starting. And yes, you will make mistakes. That’s part of the deal.

Does that mean you’re not cut out for this? No way. Every successful entrepreneur goes through these moments.

Your First Deal Will Be Awkward. Embrace It

Picture this: you’re on your first call, sweating bullets because you’re not just talking – you’re pitching something you care about. But worry creeps in. Are you saying the right things? Will they see the potential in your idea?

Then comes your first formal meeting, and maybe it feels like you’re speaking a different language.
(They just said “Heads of Terms” – what now?) For many new entrepreneurs, the process feels like being thrown into deep water without floaties.

Fear Is Fuel – Use It

We fear mistakes because we think they’ll ruin everything. But here’s the truth: they don’t. They teach. Even seasoned pros make errors. The difference? They’re used to learning from those moments instead of stressing over them. Making mistakes is just a natural part of becoming a skilled entrepreneur. You’re building a real skillset here, and it takes time.

By embracing a “learn by doing” approach, even the mistakes become less intimidating.

Why Moving Out of Your Comfort Zone is Where the Magic Happens

The first time you try anything difficult – making a deal, for instance – there’s a learning curve, and it’s steep. You might’ve been a whiz at other things, but you’re starting fresh here. But here’s the truth:
This is how you learned every other big skill in your life. This isn’t a “one and done” scenario. You’ll grow with each deal, and soon, the discomfort will turn into confidence.

Turning Discomfort into Progress

With time, things that once felt awkward or impossible become second nature. Maybe that first call was shaky, but you made it through. The next time? It’ll be a little easier. Progress doesn’t mean you don’t feel the jitters; it means you learn to work with them.

And let’s face it: you’re here because you want a different path. The nine-to-five isn’t your game, so here you are, diving into entrepreneurship.That takes guts.

The Power of Having a Community: Support Makes All the Difference

Getting through these first hurdles is much easier with a support network. You need people who’ve been in your shoes and can offer advice, calm your nerves, and keep you on track. That’s where communities like Indiemaker come in.

In a community of like-minded entrepreneurs, you’re surrounded by others who get it. Here, you can lean on each other for:

  • Advice on calls and deal-making – Learn from people who’ve made similar deals and avoid classic newbie mistakes.
  • Course correction – Get honest feedback on your strategy to stay on track.
  • Confidence boosts – Knowing you’re not the only one nervous about that first deal can be incredibly comforting.

Having the right community around you helps break through the nerves and feel empowered.

What Happens After the First Deal? (Hint: It Gets Easier)

After you complete that first deal, something interesting happens: Each future deal gets a little easier. You’ve now got what we could call “deal experience.” You’ve faced down the fears, learned from the inevitable mistakes, and come out the other side stronger.

Think of it as getting your first deal under your belt.
After that, you’ll have a clearer sense of:

  • What works
  • What doesn’t
  • Where you can improve

You might even look forward to the next one.

If You’re Ready, Don’t Go It Alone

First-time entrepreneurs don’t just need business advice – they need an honest, relatable community. That’s what Indiemaker offers.

You’ll find people who’ve navigated these same early waters with us. It’s not about finding a magic shortcut – it’s about having the proper backup to make each step manageable.

Our community offers support in many forms:

  • 🤝 One-on-one connections
  • 💬 Group discussions
  • 📢 Real-time support channels

And unlike some communities, you’re not in for a recurring fee or hidden upsells.
We keep it simple and accessible so that everyone feels welcome and empowered to keep making moves.

Join Indiemaker

Find your people — the ones who’ve been through it, figured it out, and are ready to help you do the same. No shortcuts. Just solid support that helps you move forward.

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