The top 10 GTM mistakes founders make
Avoid these and you'll be well ahead of your peers
I’ve spent the last six years helping 150+ mostly first-time founders figure out their go-to-market. Most of them were brilliant at building product. Very few were good at selling it, at least not at first.
Their mistakes are remarkably consistent, regardless of what they were selling. If you can avoid these, you’re already ahead of most of your peers. Let’s get into it:
1. Using your investor pitch as your sales pitch
Investors and customers are two completely different audiences with two completely different needs:
Investors are buying the future. They want to know the team, the market size, the trajectory, the vision for what this becomes in five years. They are used to hearing founders use obscure jargon to define a new niche.
Buyers are buying the present. They have a problem today, they have a budget today, and they want to know if your product solves it. They don’t care where you went to college, what your TAM/SAM/SOM is, nor that you are the world’s first at what you do.
When you walk into a sales call with the deck you used to raise your seed round, you’re answering questions nobody asked.
2. Turning your first win into your ICP
You close your first deal. It feels incredible. So you go look for more companies that look exactly like that one — same industry, same size, same persona. Reasonable instinct. Often wrong.
The even more dangerous version: you close three deals across three different segments and decide you have three ICPs. Now you’re chasing fintech, healthcare, and logistics simultaneously with a team of four.
The single biggest cause of GTM slowdowns I see is casting too wide a net too early. When every customer looks different, your messaging never tightens, your demos never sharpen, and your conversations never become predictable. One ICP, one motion, one repeatable story.
3. Cranking up high-volume cold outbound
If you don’t have dozens of similar customers you likely don’t yet know what your target market actually cares about. That alone is reason enough to not waste time on high volume outbound.
Warm intros are always where you start. Not because cold outbound never works — it can — but because asking for intros forces you to build the network that teaches you what these buyers actually care about.
The founders I see ripping through 5,000-contact sequences in month two are usually doing it to avoid the harder work of having ten real conversations with people they had to ask a favor to meet.
Build the network first. The volume play comes later, once you actually have something predictable to scale.
4. Pitching before you’ve done discovery
Discovery is not a formality. It’s the entire game. Before you launch into your pitch, you need three things from the buyer:
A pain point that happens often enough that they’re willing to spend money to make it stop. Not a nice-to-have. Not a someday problem. A recurring, expensive headache.
A clear understanding of how they’ll measure success. If you both can’t articulate what “this worked” looks like in six months, the deal is going to die before it reaches the finish line.
The full cast of characters involved in the decision — champion, blockers, whoever signs the contract. Single-threaded deals get killed by people you’ve never met.
Pitch before you have these and you’re just performing for an audience that hasn’t told you what they want to see.
5. Talking too much on sales calls
You cannot persuade someone to give you money if you don’t know what they’re thinking. You cannot know what they’re thinking if you’re the one doing all the talking.
I’ve reviewed over a thousand founder-led sales calls. The bad ones follow the same shape — the founder talks for 25 of the 30 minutes, the buyer nods and says “interesting” a few times, and the call ends with “let me think about it.” The good ones are the inverse.
Ask a question, shut up, and listen. Then ask another one.
6. Ending a call without booking the next one
People use their calendar as their to-do list, so if you’re not on the calendar, you’re not on the to-do list.
It doesn’t matter how much they loved the demo, how warm the conversation felt, or how senior they were. No next meeting booked = the deal is already cooling.
Book the next step before you hang up. Every call. Every stage of the process. No exceptions.
7. Fumbling pricing
Pricing is where I see otherwise-confident founders fall apart - e.g:
Delaying the conversation — “let’s circle back on pricing next time”
Deferring entirely — “what’s your budget?”
Negotiating against yourself before the buyer has even pushed back — “it’s $50k, but we have flexibility, and honestly we can probably work something out”
State the price. Ask how it sounds. Shut up. Let them respond. Whatever happens next is information, not a verdict.
8. Confusing product access with a pilot
A pilot has a defined success criteria, a defined timeline, a champion driving usage, and a clear path to an annual contract if it works. Giving someone a login and hoping they figure it out is not a pilot. It’s a free trial.
When you leave buyers to evaluate the product on their own, you’re rolling the dice that they’ll log in unprompted, navigate to the right feature, have the exact use case in front of them, and find it so irresistible they come back asking to pay you. That almost never happens. They get busy, they forget, they churn out before you ever had a real shot.
Run actual pilots. Define what success looks like. Stay in the deal.
9. Negotiating over email
Email gives you words. It doesn’t give you reactions.
When you send a price over email, you have no idea if the buyer winced, shrugged, or smiled. You don’t know if they think it’s a bargain or a robbery. You’re flying blind into the most important conversation of the deal.
Pricing and negotiation happen live. Always. Get on a call, watch their face, listen to the pause before they respond. That’s the data you need to know where you actually stand.
10. Hiring an AE prematurely
Here’s the test: never hire an AE unless you are confident you can get them to quota with a predictable lead generation and closing process you’ve already built.
If you can’t consistently close deals yourself, an AE isn’t going to figure it out for you. They’re going to flounder, blame the product, blame the leads, miss quota, and you’ll be back in the seat in nine months — except now you’ve also burned $250k and wasted half your runway.
Your first GTM hire is almost always a deployment strategist or a founder’s associate — someone who absorbs the repetitive parts of the motion you’ve already figured out, so you can keep selling and keep learning. The AE comes after the playbook exists, not before.
If any of these sound familiar to you, talk to me about sales coaching. We’ll talk about where you are currently stuck, what a typical coaching engagement looks like and if its a good fit for you.