Why I started an ed-tech company for college internship prep.

I have a story that you may find familiar.

Growing up, I never knew anyone who went to an Ivy League school, or wore a suit to work, or had a role in an elite professional industry — and so when I got to college in the fall of 2018 and recruiting began, I was immediately overwhelmed.

I remember opening an email from the career center during my second week of school and thinking, “I don’t even know where my dorm is, how am I supposed to be ready for a career fair next week?”

Recruiting for college talent happens fast and can permeate every part of campus culture. Undergraduates quickly learn to frame their major around what job it leads to, they rush to coffee chats between lectures, and they work hard to balance their academic schedules with interview season.

While all of the career opportunities can be exciting, they can be equally overwhelming and students who aren’t already prepared to navigate the process get left behind.

I was one of those students.

Between ramping up to the pace of college life, getting accustomed to the academic rigor, and dealing with homesickness — I didn’t even think about securing a summer job. But by the end of the winter recruiting cycle, I started to see many of my peers securing professional summer internships. All of the sudden, I began to feel really behind the ball and worried that I was already washed up at 18.

Thankfully, however, I was lucky enough to meet a couple of seniors through a friend-of-a-friend. I didn’t know it at the time, but they had already been in and out of several prestigious internships and were eager to help out other young students trying to find their way.

Without my asking, they emailed me several incredible internship opportunities that were still accepting applications and when I got through the first round, they invited me to their dorm to break down exactly what I should expect next.

They answered my questions about the role and gave me the low-down on the employer so that I had context. They helped me with practice interviews, introduced me to other employees, and texted me daily to ensure I was practicing on my own. What’s more, they eased my worries and self-doubts which every aspiring intern — especially one from my background, not knowing anyone who’d else worked in the kind of space I was applying — is bound to have.

The morning of the interview, I ran to my mentors’ dorm and borrowed a few last-minute things: brown dress shoes, a suit jacket, and some second-hand confidence. Then I was off to Philadelphia for a 3 hour, back-to-back final round.

And…I got the offer!

As I made my way back to campus I remember being so thrilled and proud but more than anything, I was grateful for the blessing of fantastic mentors and for my newly achieved success. I got out of my UBER and immediately put on my celebration music: Juicy by Biggie Smalls — “It was all a dream…”

Landing the offer, and doing so with such a strong community of mentors supporting me felt incredible and planted a seed in my mind:

Everyone should feel this way.

My first week on the job, June 2019 (I’m third from the right).

That thought stayed with me throughout my summer internship and by the time I got back to campus in the fall of 2019, I had a plan. I was eager to help the next group of freshmen who were just trying to figure it out like I once was.

That year, I mentored around 50 peers and eventually joined several student groups — African Student’s Assoc., Princeton Black Men's Assoc., Prospect Student Ventures — to amplify my impact throughout all of campus.

I would set up practice interviews, talk with people about their goals and ambitions, and offer comfort in the form of my own story. Pretty soon, however, junior year — the year we all went virtual — started kicking my butt and I had to ask for help managing things.

What I did was start referring some mentees to my friends. This allowed me to keep afloat and, as it turned out, ended up working better for the students who could now connect with other relevant folks and get insight into the recruiting processes of other companies. By December last year, my mentor/mentee network grew to over 200 and started reaching other schools as well.

At that point, did I see myself starting a company? No. But I saw that I was addressing a huge problem.

Through my mentee network, I noticed that many students — often BIPOC, first-gen, or of lower socioeconomic backgrounds— end up being much less competitive than their peers not because of their lack of talent but because they don’t have a network of family, friends, or mentors who can guide them.

(Prof. Lauren Rivera at Kellogg points out many other issues with the college-to-career pipeline including recruiter bias, socialization, and exclusionary practices. More on that another time.)

Curious, I did a survey of 285 students across 40 schools and found that internship preparedness is a much broader problem than I ever realized. In fact, 68% of undergraduates — not just those from any particular background — feel less than prepared for job interviews given the currently available resources (ranked a 3 or less on a 1–5 scale; 5 being very prepared, 1 being very unprepared).

Why do most students feel like this? Because none of the current resources prepare Gen-Z students the right way.

More than any other resource, 38% of students surveyed listed friends/mentors as their preferred method of getting help with internship prep (career center 24%; existing NGOs, recruiters, and current online solutions <7% each).

What’s more, the data predicts an 11% increase in feelings of preparedness for undergrads who know just one other student with experience at their job of interest. This “network boost” increases to 12% for women and a whopping 26% for Black students in general.

I launched this informal survey out of curiosity, but once I saw the results, I knew why I was able to grow a list of 200+ mentees in just a few months: No one else was actively helping students prepare for jobs the way they wanted to — the way that was helpful — through peer networking.

Especially as the world reels from post-COVID fallout — joblessness, employee dissatisfaction, virtual learning, a changing recruiting landscape — Job-seeking college students desperately need help and the best way to do that is to connect them with other students who are more experienced and still relatable.

That’s exactly why I launched Connect UPskill.

Our startup is building an online marketplace where students can book sessions with peer coaches. For example, we allow them to quickly set up practice interviews, look over their resumes, and share the many other insights they have from their time successfully applying to the job — all with the goal of helping as many students as we can get their dream job.

Since last winter, I’ve leveled up from a “one-person/many spreadsheets” approach to a full-time founder and I teamed up with a few friends from Twitter, Google, Microsoft, and the tutoring/education world to help. What’s most exciting, though, is that we’ve already had some early success

Pre-launch, we tested iterations of the platform with over 400 users and we helped students secure jobs at Google, McKinsey, JP Morgan, Goldman Sachs, Bain, Microsoft, and others. Looking ahead, we’re eager to help more students break through as well as broaden the types of opportunities that we can help them prepare for.

To do that, we’ve launched our waitlist and plan to drop the full website in August. We’ll start small but plan to quickly branch out to as many schools as we can — all the while bringing on upperclassmen eager to share their experiences and offer a helping hand to students who wouldn’t otherwise get that same support.

My team and I are laser-focused on closing the network gap for job-seeking students — and we won’t stop until we democratize recruiting for everyone.