Skip to navigationSkip to content
FLYING SOLO

Being a young startup founder was isolating—here’s how I coped

REUTERS/Mike Blake
It can be lonely up here.
  • Jesse Kaplan
By Jesse Kaplan

CEO, Parcel

Published Last updated This article is more than 2 years old.

One thing I never expected when I founded a startup on my own shortly after college graduation was the level of isolation I felt at times.

My decision to fly solo so early in my career was often met with surprise and uncertainty. Prospective vendors, partners, and employees were less inclined to take a chance on a lone, inexperienced founder, incredulous that I could build and grow a massive company on my own. And as the demands of running an early-stage business inevitably piled up, I had no one to share responsibilities with, bounce ideas off of, or keep me motivated. In the face of early skeptics and operational burdens, staying focused without a cofounder (or, for a while, even a coworker) was not always easy.

Almost five years later, it’s safe to say that workplace isolation is no longer a concern—my company, Parcel, was acquired by Walmart in the fall of 2017, and I now have a few million coworkers. Still, the techniques I learned for coping with those lonelier early days remain fundamental to my working style.

Find your people first

Knowing that I wanted to join or found a startup right after school, I scheduled all of my senior year classes on Wednesdays in order to travel from Boston to New York City for networking meetings. In preparation for those six-day “weekends” in New York City, I sent hundreds of cold emails.

A lot of recent graduates use their first job to make friends and build a community in their new city. Without coworkers, you miss out on both a personal and a professional network. It’s important to spend meaningful time building a support system around you, even before you start building a business. It’s a time-intensive process, but it pays off in dividends. The contacts I made during those early trips have since become investors, trusted mentors, and close friends.

Manage yourself like an employee

Without the structured feedback you’d (hopefully) receive from a manager, evaluating your own performance can feel impossible. It’s essential to step back every now and then and give yourself the same level of managerial support that you would offer an employee.

Every Monday, commit to measurable goals for that week. It can be easy to panic over how much is always left to be done, especially when that list is ever-growing, but seeing a completed checklist at a week’s end is reassuring and encouraging.

Particularly during trying times like the fundraising process, you might not feel like you’re making any progress. Just as you’d give an employee positive praise for a job well done, give yourself a pat on the back (or, often in my case, a jar of Nutella) after finishing off a productive week or hitting an ambitious goal.

Among entrepreneurs, there’s a tendency to feel guilty every moment you’re not working—pressure I’ve undoubtedly fallen into at times. A good manager can help you strike a healthy work-life balance, but if you’re running your own company, that job is yours. Carve out time in your calendar to put work aside and relax—it will only help you work smarter.

Seek out the competition (and commiseration)

In a moment of self-doubt about your business model or fundraise, you can’t always lean on investors or employees who look to you to be a model of confidence. Friends and family mean well, but their bias toward supporting you could steer them away from providing the honest feedback you need.

I’ve been surprised to see that some of the most helpful insights can come from those you’d least expect. In our earliest days I was hesitant to get in touch with other delivery companies in our space, concerned that it would put Parcel on their radar and risk more competitive pressure. The reality is just the opposite—speaking to other relevant players can introduce valuable learning opportunities, and often these seeming competitors can one day be allies or partners.

But perhaps most important of all: befriending other founders is a powerful way to transform your business and maintain your sanity. Whether they’re in direct competition or in an entirely different industry, there is empathy between young entrepreneurs thanks to the universal vulnerabilities that come with building a business from scratch. Lean on these contacts when you’re out of your depths—chances are one of them will have a roadmap to follow and a sympathetic ear to hear you out.

Jesse Kaplan is CEO of Parcel.

📬 Kick off each morning with coffee and the Daily Brief (BYO coffee).

By providing your email, you agree to the Quartz Privacy Policy.