The Top Misconceptions in Startup Sales, Episode 1
“Paul, sales is all about human nature.” It dawned on the founder I was coaching. I could feel him wanting to engage even more with the topic, now that he had had this realization. Understanding what it means to be human was going to help him move product.
A big part of my work is to get founders and startup operators to think differently about startup sales and go-to-market. That usually takes changing their minds on what they initially believed about themselves and the world. And moving them onto more productive views of how things work.
That’s coaching.
Over the last 9 plus years, hundreds of founders have come to me for coaching on their sales and go-to-market challenges. And I’ve done my best to help. In the next few months, in the form of weekly episodes, we’ll be looking at the top startup sales misconceptions folks possess. And how I get them to think instead. Reading this series will make you smarter and more aware than most startup operators, as you’ll already know how to think about go-to-market and sales, and avoid some of the biggest pitfalls. Consider this your cheat sheet in shaving months off your revenue growth journey. Without further ado, here’s your first installment.
“Email is dead.”
I can’t tell you how many times I hear this one. And part of me understands why. It’s never been harder to execute on automated email outbound. Spam filters have never been smarter. As a startup trying to go outbound, you’re competing against teams of PhD’s tasked with preventing unwanted email to hit inboxes. The Googles and Microsofts of the world refine their algorithms to repudiate all cold emails, while we try to find ways to outsmart them. It’s a coevolutionary arms race.
When I started doing outbound about 15 years ago, things were a lot easier. Emails would land smoothly in inboxes. Your copy didn’t need to be sharp. And you weren’t forced to warm up your mailboxes for several weeks before launching campaigns.

Having said all that, declaring that email belongs in the morgue is a great disservice to all startups. You can be successful with it. You just have to be more skilled and disciplined than ever. For example, we’ll prescribe to our clients that they warm up as many as 20 inboxes for a sturdy automated email outbound initiative. 12 of which will be active to start. While 8 sit on the bench. Waiting to be entered into the game at a moment’s notice, if any of the initial inboxes get in spam trouble. We’ll also have our clients use products like Amplemarket which not only offer an email warmup module. But also has a feature called Liquid, which rotates parts of your emails, in an effort to avoid spam filters. We’ll also tell our clients to reduce the use of web links in the body of their emails. Or avoid certain words like “free”, which can also put you in spam jail. I could go on and on.
These guidelines have to do with beating filters directly. But what happens when a prospect labels your email as ‘Spam’?
Well, then you’ve got very little chance at reaching additional prospects. Your domain reputation sinks, making it almost impossible for other emails sent from the same place to actually land in an email inbox.
A prospect putting you in ‘Spam’ has a lot to do with actual copy. Your messaging. So, what do prospects look for when deciding whether or not to banish you to the gulag of email senders?
A lot of it has to do with signs of automation. Any whiff of you turning a crank will turn off email recipients. The more you sound human, the better off you’ll be. Formality is your enemy.
We often tell our clients to write to a friend, in an effort to get them to be less formal. You have to remember: It lowers your status in the eyes of your prospect. They think to themselves, ‘Why are you treating me with kit gloves? Do you not respect yourself? I’m just another human.’ But it also makes you feel more foreign to them. Think back to the last time you received an overly formal email. Did you think to yourself, ‘Man, I want to keep reading this.’? Definitely not. You most likely quit reading the message a couple sentences in. If you even got that far.
When overly formal emails hit our retinas, we think to ourselves ‘This is definitely automated and impersonal. It feels like it’s coming from a machine’, as we press “DELETE”. While, when you receive an email that drips with humanity, you ask yourself, ‘Could this email be written just for me? Could this have been sent one-to-one, as opposed to one-to-many?’
If you’re able to fall in that latter bucket, you’ve already won. Prospects linger longer on your message. You have a real shot at making an impression. To garner yourself an interested reply. All while benefitting from the scalability and time efficiency of automation.
So next time someone tells you that email belongs six feet under, tell them off. When executed properly, email can be a great way to soar in outbound sales. We have clients that generate hundreds of thousands of dollars in pipeline per week thanks to automated outbound email. You just need to execute at a high level.
Next week, we’ll dive into why asking for feedback is a poorly used weapon in startup sales.