7 Mistakes Founders Make When Chasing Their First Deals

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Every founder thinks their challenges are unique, until you’ve seen a hundred startups make the exact same mistakes.

I’m Macy Mills and I lead GTM at a16z speedrun. My job is to give our speedrun founders an unfair advantage by helping them accelerate their traction. We do this with large-scale events, customer introductions, and hands-on advice.

Today, I want to share the seven mistakes I see most often at the early stage, and how to fix them fast so you can build real traction.

Watch the full video below, or scroll down for all seven mistakes:

1. Don’t Wait for Perfection Before You Start Selling

You don’t need a perfect product to start selling. You need a hypothesis about a real problem that you think you can solve. If you’re waiting until your deck is beautiful and your product is flawless, you’re honestly waiting too long.

Selling is a contact sport. You learn by doing. Get out there, start talking to customers, get feedback, and adjust. The input you get from real conversations is way more valuable than making sure you show potential customers the perfect pitch. Feedback beats stealth mode every single time, and there’s a reason why everyone is building in public.

Early customer signals are what is going to help you get to product-market fit, specifically by allowing you to diagnose when something isn’t working as soon as possible. It’s critical you understand your customers’ pain points deeply, and by waiting until you feel fully “ready” you may find yourself too far down the wrong path.

2. Stop Underpricing Yourself

This is a huge one. Founders are afraid to charge what their product is worth. I can’t tell you how many times I’ve seen founders charging one or two thousand dollars a month. That’s pocket change for big organizations. I personally don’t even think it’s worth asking for money if you’re only asking for that much. At that point, you should just move forward with a “design partnership” or a customer you don’t charge anything in return for product feedback, marketing case studies, and references. Honestly, at some point those intangibles have more value for you.

Founders think, “If I make it cheap, it’ll be easier to close,” or “I don’t have enough value here to ask for money yet.” Wrong. You should always start by asking for an amount that scares you just a little bit. You may be surprised at how many times you hear yes. And if they say no way, then fine: ask them what they feel is fair. Have the confidence to throw a number out there and see what happens.

3. Find the Person Who Holds the Budget

You’ve got an enthusiastic champion inside the company. Awesome. But unfortunately, enthusiasm doesn’t sign contracts. You need to find the person with budget authority early.

Ask things like, “Who else needs to weigh in before we move forward?” or “Whose budget would this come from?” The fastest way to stall a deal is to think you’ve got an opportunity when it turns out to be a fan instead of a financer. You need to be positive you’ve found the budget authority, also known as the Economic Buyer.

4. Listen More Than You Talk

The best founders learn to listen. They ask the right questions, like “What’s the process for getting this deal signed?” and “How high of priority is solving this problem for you right now?”

I like to give the guidance of an 80/20 rule: 80% listening, 20% talking. Ask open questions and write down the customer’s exact words. Once you have a good understanding of their priorities and problems they are hoping to solve, you can then deliver a pitch that resonates. They will immediately trust you more, because they know you were listening to them, and seem to understand the problem.

5. Don’t Fall in Love with Just One Customer

I see this every week. A founder gets one hot lead, one big logo, and suddenly all roads lead to that one customer. But if you’re hanging your fundraising outcome on one deal, you’re setting yourself up to fail.

Founders should be running many design-partner conversations in parallel. The reality is that a pipeline is just that, and many will say no. As a founder,you have to get used to hearing no and moving on. You should actually see it as a blessing so you can stop wasting your time. If all your potential design partners want similar things, that’s great news. But don’t get your hopes up with that one big logo. Make sure you’re spreading the love across a larger pipeline. And celebrate the no’s! :)

6. Your Pitch Should Evolve with Every Conversation

One of the biggest mistakes I see is founders treating their pitch like it’s permanent. Your pitch is supposed to get better with every single conversation. The first ten times you explain what you do, you’re really learning how people hear it. Watch for where they light up, where they look confused, where they interrupt you with questions. Those are great signals to take as learnings as you continue to hone your pitch.

Your story should evolve as fast as your product does. After every call, I recommend taking sixty seconds to jot down what resonated and what didn’t. That’s how you build a pitch over time that actually converts. And when you’re in a live conversation, stay flexible. If a buyer reacts to a certain product feature, lean into it. The best founders know how to read the room and adjust on their feet.

7. Don’t Hire a Salesperson Too Early

Founder-led sales is so important at the early stages of building your business. For technical founders, it can be tempting to try and hand off the sales job so you can focus on building the product.But the truth is, if you can’t sell it, a salesperson definitely can’t.

Founders have to run those early laps themselves. You’re discovering the sales motion, along with selling a product. You’re learning what customers are saying firsthand and allowing that to influence your product roadmap. No one can influence the product roadmap faster than you! You might as well get used to it because being a CEO involves a lot of selling. Customers are actually going to take you more seriously if you’re the founder, because you’re there selling the vision that you are obviously passionate about it. Once you’ve closed many repeatable deals and know the playbook, then you can hire that salesperson to help you run it. But not before.

Those are the seven biggest mistakes I see founders make when chasing their very first deals. If you avoid even half of what we covered here, you’ll move faster, close smarter, and build real traction: the kind that investors like to see on paper.

If you’re in the middle of early-stage selling, let us know how it’s going.

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