How I built 2 six-figure ed-tech businesses with cold outreach

For the past 8 years of my career, I’ve made a living off of finding interesting, novel ways of locating digital “watering holes” of specific target segments, finding creative ways to get some sort of contact information, and then sending and optimizing cold outreach campaigns.

I first did this when I was a student in college working on a bunch of small startup ideas all focused on selling to other college students (was the only thing I knew at the time).

When I was trying to find ways of getting in touch with students, I discovered something interesting.

~150 of the top 200 Universities in the United States all used the same white-labeled platform to manage a directory of their student organizations (clubs). Every single one of those 150 colleges had a directory of all their student organizations that was open to the public and followed the exact same page structure.

At the beginning of every semester, I would use Selenium to navigate to those 150 links, scroll through all of the pages and grab the following fields for every club.

Club Name
Club President Name
Club Email
Club President Email
Category
School

Writing the initial Selenium script took me about 5 hours (I know, I know…I didn’t know what the f*ck I was doing - that was my first time using python.)

But after that initial investment, every semester I could hit “run” and with zero extra effort have an updated leads list of anywhere between 80,000 - 90,000 student clubs, their general email address, and their president’s email address.

However, just because you have 80,000 emails of people who fit your core demographic, doesn’t mean you automatically have paying customers, there’s a big jump from cold lead to converted customer.

That process took me about a year to finally master.

The target demographic I was dealing with (college students) have an incredibly fine-tuned BS meter. If they get a cold email from a stranger, especially one that looks automated, without hesitation they’ll archive, delete, or mark it as spam. I learned this the hard way.

After a ton of testing, and running mini-experiments I found that most college students didn’t fully understand how advanced sales email software had become.

Using Reply.io, I set up outbound drip campaigns that included their name, the club’s name, and their school's name. That helped a little bit but still would only get the response rate up to 2%.

The thing that had the biggest effect was sending drip campaigns. These were 4 email sequences where if the last email didn’t have a reply, it would automatically follow up, in the same thread, 2 days later.

I found that this simple trick made a lot of students think “oh shoot - Andy is a real person trying to email me, this wasn’t just a blasted email campaign with some variables.”

Just setting those email campaigns up took reply rates up to 6-7%. A true game-changer.

From there I did other refinements that you might expect any cold email sale guy to try. Here are a few notable things that worked for me.

Example email linked here.

We A/B tested the subject line a TON. The subject lines that worked best were always ones with emojis that were related to the school. (🔵🟠 for UVA, 🐏 for UNC, etc)
We built an automated script that would take a formal name of the student organization and turn it into something more casual. Basically, what you would say if you were talking about the student organization to a friend over coffee? (180 Degrees Consulting UNC-Chapel Hill -> 180 Degrees, American Lung Cancer Screening Initiative at UNC-Chapel Hill -> ALCSI, etc)
Emails that asked the clubs to share a link or some form of marketing material with their members sometimes worked but never as well as emails that tried to provide value to the club. Asking clubs to share resources (that were lead magnets), and host us for talks or workshops, was always a lot more effective.

Through this method, I was able to test and validate (more often invalidate) 8+ different ideas for startups that I had as a student. From these experiments, I was able to start and grow two businesses focused on serving these individuals. One was able to generate $140k in its first year, the second has now been in business for 6+ years and topped out at just under $900k/year in revenue.

Now - you might be asking. Would this strategy still work today?

Probably not quite as well as it did 6+ years ago - but maybe!

Since then, the college-student-organization-crm-mamangement-tool-for-university space has become more competitive and the same tool that had a huge market share doesn’t have nearly as much dominance as it once did. Also, I’m sure students have become a little more aware of the capabilities of cold email marketers like me and their bs-automated-emai-dectors are probably a lot more sophisticated.

I wanted to write this article not to brag, or to give you the exact strategy you can use if you also want to reach this demographic. Instead, I want to stress the point that whatever target segment you’re trying to reach, there’s almost definitely a way to use a little bit of creativity, web dev knowledge, and grit to generate a pretty substantial lead list and start running outbound campaigns.

In the coming weeks, I’ll try to write more about some of my other crazy lead gen quests that include

Filing Freedom of Information Act requests
Using selenium to scrape all the emails from people who commented on viral LinkedIn posts
Scraping info from LinkedIn Groups
A fully automated LinkedIn Sales Navigator -> verified email -> 5 email drip sequence -> CRM -> scheduled meeting flywheel

And a whole lot more.