Oldschool and newschool outreach

We’re getting ready to open up our first 5 spots with Skyp.ai. If you want to level up your outreach–affordably–click and join the waitlist, or just reply. Must be at least pre-seed funded or $1mm ARR with at least 10 customers.

Everyone has strong opinions about outreach. Some say you need to send hundreds of emails a week. Others say if you’re not cold calling you’re not trying hard enough and suck as a founder.

Most outreach opinions are flat out wrong.

In the age of AI, outreach just got a lot more complicated–or much simpler, depending on your perspective. This post is about oldschool and newschool outreach. If you don’t need (or want) more leads, you can stop reading here. For everyone else (everyone?), I hope to shed some light on this well lit and still scary corner of GTM.

Just one approach

To be sure we’re discussing the same thing, cold outreach is reaching out to people you don’t know. It might be phone calls (cold calling, about which I have strong opinions), or cold email, or outreach on LinkedIn, X, Instagram, Telegram (yes that’s a thing) or any other digital media.

Outreach is just one approach among many to get new customers. It is not necessarily the best approach, and for some companies or industries it might be among the worst. That said, it works well for many companies and there are right and wrong ways of doing it.

The wrong way

There are so many ways to fail at cold outreach, I’m not actually sure where to start. Usually the services people are pushing on you – those emails in your spam folder offering to get you leads for $400 each, or a list of people in your target market, or that angel investor telling you to send 3,000 emails in Hubspot because it worked for him (did it? really? does he have screenshots?) – are doomed to fail. Why? Lots of reasons, too many to list here.

But it’s easy to describe the two broad ways to fail. First is to not focus on the customer. The second is to do things technically wrong.

Not focusing on the customer is surprisingly easy. The key to any outreach is putting your customer first. If you’re doing the customer a favor with your outreach, you might have a chance. There are so many ways to do them a disservice, including: