Stop Overthinking Your Outbound

Recently, I learned what retardmaxxing means, and I have never felt so seen by a slang term.

As humans, we overthink everything. What we want for dinner. What text to send the guy we like (I have absolutely workshopped a "haha yeah" in my Notes app for 40 minutes). Which cocktail to order at the bar (margarita with salt on the rim or a spicy margarita should not be that complicated).

Life does not need to be this complicated. We are the only ones standing in the way of decisions that are not going to change our lives.

The same thing is true for your sales motion. You're stuck thinking about what is going to work, and you're too scared to run a handful of experiments and see what sticks.

If you're like me and nobody told you about the latest Gen Z slang, stay with me while I explain.

The concept is simple: drop the overthinking, act on your instincts with confidence, and stop getting stuck in analysis paralysis. Most people are stuck in a loop of overthinking and are too afraid to try. What's the worst that can happen? A prospect says your product is dumb? Congrats, you just got more honest feedback than your last three demo calls combined.

Okay, but where am I going with this?

Drop the overthinking, stop rewriting, and start sending

What is thinking about your perfect cold email going to do for you? I'll answer that. Nothing. It's going to live in a Google Doc titled "outbound v7 FINAL (actually final)" with 14 comments from your cofounder, and it will never, ever get sent.

Instead of thinking about it, do something. Take a stab at a draft. Scan your inbox and read the cold emails you've gotten in the last two weeks. Which ones did you open? Which ones did you reply to? Which ones did you archive so fast? You already know what good looks like. You've just been ignoring it.

Now write the email like you're texting a friend. Don't try to sound smarter than you are. Nobody in the history of mankind has read "I hope this email finds you well, I'm reaching out regarding a synergistic opportunity" and thought, yes, this person gets me. Make your email stupid simple. One problem, one line on how you fix it, one ask.

Here's the part no one tells you: your prospects are skimming. They're reading your email on their phone between meetings, in the Starbucks line, or on a date (yes, really). They are not grading your sentence structure. They're deciding in three seconds if you're worth it. Stop polishing. Start sending.

Act on your instincts with confidence, because they aren't random

You raised a few million dollars. You have product market fit. You have SOME revenue. So whatever you do, do not doubt yourself now.

No one can tell you exactly what's going to work or how your startup becomes a billion-dollar rocketship. Anyone who says they can is selling a course. But if you get consistent reps, speaking to the right ICP, with the same copy every day, day in and day out, and you don't give up, you will have revenue. This is not a motivational post. It's simple math.

You have to be okay trusting your gut. If you feel like someone will resonate with a case study, send it. If you feel like nobody is opening your email on a Tuesday at 4pm, change the day and time of your sequence. If you think a prospect would rather watch a 60-second Loom than read another wall of text, record the Loom.

Your instincts aren't random. They come from every demo you've run and every "circle back next quarter" you've heard. That's pattern recognition, and it's worth more than another week of planning.

Stop getting stuck in analysis paralysis, or you'll be at the same ARR you were nine months ago

This is the worst place you can be. It's like having the same nightmare every single night for 12 days straight. You're spinning your wheels and stressing yourself out for no reason.

The best in any game are trying, testing, shipping, and iterating quickly. They are not sitting around waiting for their competitor to win. Sorry, but B2B SaaS is a rat race. There's a new product, raise, or acquisition every day. You have to move fast or your company will die.

There is no real hack or secret to building a GTM strategy that works like a revenue machine. Find your ICP, scrape their emails and phone numbers, and write outbound that actually speaks to them. I don't need your first round of copy to be a home run. I need you to write it, try it, and rewrite it.

You will rewrite your cold emails 10 times before you even get to an average open rate of 17%. This is where most teams get stuck. To really see traction, you need to run. Do not wait until you have the perfect cold email written, otherwise you will be at the same ARR you were nine months ago. This is not a threat. It's the truth.

Your first cold email is going to be bad, and that's the point

Here's your homework. Today, not next Monday, not after your PTO to Hawaii. Today.

Open a blank doc. Write one cold email in 15 minutes or less. One problem, one fix, one ask. Pick 50 people who fit your ICP and send it. Then go do literally anything else and let the data do the overthinking for you.

In two weeks, look at what got opened, what got replies, and what got you a "please remove me from your list." Keep what worked. Kill what didn't. Rewrite. Send again.

That's it. That's the whole strategy. Nobody is going to remember your mediocre first email, but they will remember the person who kept showing up in their inbox with something better every time.

So stop workshopping your "haha yeah." Order the spicy margarita. Hit send.