The biggest blocker to sales is...

The fastest growing startups are freemium. But freemium is really hard to pull off for most founders, for many reasons. First, your prospects need to evaluate/buy software in this way. Second, your time to value needs to be measured in minutes.

For all other software, direct sales is the most effective play. It’s the fastest way to understand a market, to experiment with different pricing, to uncover your product gaps.

But a lot of founders, especially technical ones, don’t launch a startup to become a sales rep.

And this is ultimately what brings them down.

In this newsletter, we’ll walk through some of the most common excuses I’m hearing in 2025 that are holding founders back from being successful with sales.

Let’s bust through some headtrash together.

Table of Contents

• Your worst enemy

• Most common pieces of head trash

  • I’m too busy

  • Cold outreach doesn’t work

  • I’m not good at sales

  • I’m scared of coming across as salesy

  • Sales is manipulative

  • I should slow down

  • Sales sucks, I should hire someone to do it

• What are you waiting for?

Your worst enemy

The one person holding you back from succeeding at sales is yourself.

You see, your mind plays tricks on you. It’s full of biases, experiences, preferences. It’s full of opinions. Some that are rational, some completely rational.

So when you have fear or doubt around sales. When you have limiting beliefs - aka head trash - you cannot trust your mind. Because it is working against you.

So the thoughts you have about sales, the reasons why you’re not doing it, they come from a deep place in your mind that wants to see you fail. Because avoiding sales means you’ll continue doing what’s comfortable. And your mind wants to keep you there.

So you have to say fuck you to that brain of yours, and recognize when it’s holding you back. Then do the exact opposite of what it’s telling you to do.

Most common pieces of head trash

Here’s what I’m hearing from dozens of founders doing sales right now, and where they’re getting stuck:

I’m too busy

No you’re not. You’re finding excuses to avoid sales.

Reality is, you’re launching a business. Revenue is oxygen. If you don’t pay the bills, you can’t keep doing this. So minimum or no effort into sales will get you nowhere fast. If 95% of your time is spent on building a product that nobody’s buying, then you’ll feel good about the work you’re doing, but your business will ultimately fail.

You need to prioritize sales with at least 50% of your time, ideally more.

Cold outreach doesn’t work

Yes it does. You’re just not putting any effort in it.

If you’re getting a large list, pulling emails from Appolo, dropping that into Smartlead, and getting a 0.5% reply rate with a 10% positive reply rate, you’re not doing outreach. That’s email marketing, done poorly.

Prospecting and outreach requires a lot of thought. Your list needs to be very small and insanely specific. How you target needs to come from a place of “folks who would have this pain.” Messaging needs to stack your research and focus on agitating the pains your prospects have. I needs you to spend time finding the right accounts, right people. Sending connection requests, starting a conversation, asking probing questions.

The vast majority of founders I speak with who say outreach doesn’t work have done none of the stuff that makes outreach work.

Building pipeline is one of the most difficult things to do. Writing a message in 30 seconds then blasting it to hundreds of people is not the type of effort that will get you anywhere.

I’m not good at sales

Nobody is when they first get started. Even sales pros 20 years in their careers are still learning and messing up.

You’re dealing with humans, and humans are unpredictable. If sales was easy, everyone would do it for the earning potential.

But sales is not easy. It requires thought, effort, constant learning and development.

I’m scared of coming across as salesy

So don’t be icky then?

Usually folks who try really hard to not come across as salesy end up in a much worst spot than they wanted.

If you were an executive, or you’ve dealt with executives, you’ll notice how they communicate. Quick, direct, to the point.

Most folks who first get into sales and try to do outreach end up being overly polite, dancing around what they really want to say. Which on the receiving end, comes across as deceptive.

I was coaching a founder on this kind of stuff recently. He was sending out messages on LinkedIn that came across as a sales email. LI is a social network, DMs are meant for back and forth conversations.

I took his 8 line structured email, and simplified it into 3 messages:

“Hey Hugo.”

“Saw you’re using JSM.”

“How’s that working for you?”

This is how elite prospectors do outreach. And they get convos in, they ask probing questions, if pain exists they move to meeting. If pain doesn’t exist, they learn something from it.

They’re not pitch-slapping. They keep it short, direct, and simple. Like how execs speak.

Sales is manipulative

No it’s not. In B2B, you can’t convince someone to buy something they don’t need.

It’s not the same as retail, where if you flatter ego enough folks will spend money they don’t have via credit cards. That stuff can be manipulative.

But in B2B, buyers aren’t spending their own money. And there’s limited amounts of cash that can be spent, across all departments. So decisions are weighed based on problems and pains. And how costly those pains are for the business.

And decisions are usually made by committee. So it’s not one person spending the money, it’s multiple people agreeing that there’s a painful problem, that problem costs the business money, a solution needs to be implemented, and YOUR solution is the best one.

There’s no way you can manipulate your way into those types of deals closing. Ever.

All you can do is help them make an educated purchase decision. Ideally they lean towards you. So your sales process really helps them buy more than it helps you sell.

I should slow down

This one is tough. Because if you’re really successful, you’re going to get insanely busy. And you’ll likely need to work at 1.5x capacity before you can start delegating anything, especially if you’re bootstrapped or self funded.

If sales is going well, the initial reaction is to slow down because you won’t be able to handle all of those incoming clients.

My word of caution: DON’T STOP.

Momentum is hard to get. You don’t want to be the reason why you lost it.

If you get a lot of demos on calendar, only 20% of them will close (even less at first).

Many folks will ghost you. Some will say they’re interested, but can’t buy for two quarters.

Things almost never go according to plan in sales.

It takes a long time to build pipeline. It takes a long time to close.

Don’t slow it down because you fear your own success.

After all, that’s the reason you started the business. You wanted to succeed.

So when things are going well, it’s the worst time to slow down.

Every SaaS company out there complains they don’t have enough pipeline. It will always be an issue. So when the momentum strikes, ride that wave as hard as you can. Because it doesn’t last. And when it crashes, you’ll wish you were too busy with sales.

Trust me, I’ve seen it play out many times.

Sales sucks, I should hire someone to do it

No you shouldn’t. Not in the early days.

It’s your job as a founder to find product-market fit. And it’s your job to figure out how the company will make money.

Those things go hand in hand. You’ll need to try a bunch of stuff.

Some stuff will work. Most stuff won’t.

Through this, you’ll learn about your market. You’ll learn about what people are willing to pay for. And you’ll go tweak the product. Then sell a few deals. Then tweak it more. Then sell.

No sales rep can do this. They don’t have the ability to change the product.

And in the early days, a lot of folks put trust in the founder knowing the product “isn’t there yet.” They will never put that kind of trust in a sales rep.

Sales is one of the most expensive roles to hire for. And one of the most difficult ones to figure out.

There are hundreds of combinations for sales motions. You don’t want to hire/fire your way into this experiment.

You’ll be doing founder-led sales until at least $300-500k ARR. Then you’ll hire your first couple sales reps that will get you to $1-2M ARR. And then you’ll hire a sales leader that will hire rep 3-300, scaling revenue even further.

Even through all of this, half of your time is going to be spent in sales.

If you’ve launched a business, you’re entering the world of sales. Full stop.

What are you waiting for?

I hear all sorts of excuses daily from various founders as to why they can’t do sales.

And I always push back on them.

“You can’t do sales? Or you don’t want to?”

Because those are two different things.

If you don’t want to do sales, then go get a job. They’ll have a sales team that wants to do it.

If you can’t do sales, it’s either because of limiting beliefs, or lack of knowledge/experience. Both of those can be addressed.

Take courses, read books, talk to people you know. Run different experiments, learn from your wins and failures, try to replicate. Sales is a lifelong profession and you need to work on it daily.

As for head trash and busting through limiting beliefs - either find a support network that understand what you’re going through. Or work with a coach. Either will help.

Let me know what you think of the newsletter, or what topics you’d like me to cover. Always appreciate hearing from you :)

For more practical early-stage sales tips, connect with me on LinkedIn.

If you’re looking for help busting through mindset and getting specific with sales tactics, reach out for coaching packages.