This 23 Year-Old Entrepreneur Delivers: Interview with Parcel Founder Jesse Kaplan

by / ⠀Blog Entrepreneur Interviews Entrepreneurship / March 10, 2015

Jesse Kaplan With Packages

Problem: Receiving packages from orders placed online is difficult in larger cities, especially in places where there is no active doorman to accept deliveries on behalf of residents. Unless the recipient is present at the time of delivery, which is typically during the hours of 8-5, a slip is left at the door, and the package is returned to the distribution center. Due to barriers with labor limitations, the USPS and UPS are not able to deliver during late hours of the day.

Jesse Kaplan moved to New York in the summer of 2013 and immediately experienced this problem. After missing packages, he would spend hours waiting in line at “local” post offices trying to recover the items he had ordered online. “There was a big disconnect from the online shopping experience and the offline shipping experience.” He decided to tackle this problem head on.

Solution: Jesse Kaplan, Founder and CEO of Parcel, describes the business as the “off-hours delivery service for online shoppers.”  Parcel hand delivers packages to customers’ doors within a one-hour window of time when they are available, whether during regular business hours or in the evening.


Even at the age of 23, Parcel is not Jesse’s first entrepreneurial venture. While an economics major at Harvard, Jesse started Cabot Café, which was the only student-run coffee shop on campus. After graduating, Jesse started a tutoring business, which he left to focus full-time on Parcel.

Before jumping into Parcel with both feet, he had 73 meetings meeting with people who lived in New York City who did not have doormen within their apartment complex. The meetings were to determine if the problem he experienced was common and if the business would be a desired service for his target market. He quickly realized that this problem affected more than just himself, and he began to pursue Parcel as a business.

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Jesse started an MVP version of the business by renting a mailing address from a co-working space where he had customers’ packages sent. He manually notified each customer when their packages arrived with a text-message and then would plan out his route and spend every night on the subway with a canvas bag full of packages. Jesse described it as an “exhilarating experience,” and noted that this allowed him to grow strong personal relationships with his early customers since he was making the deliveries himself.

Package of Fun

Jesse Kaplan 2If you hear the words package and fun in the same sentence, you most likely aren’t talking about shipping cardboard boxes — that is unless you’re talking about Parcel. I was skeptical when Jesse mentioned that one of Parcel’s goals is to make the process of receiving a package more enjoyable and even fun for the recipient. Although I’m happy when a package arrives safely, I never thought of the process as a fun one.

How can you liven up a seemingly dull process?

As mentioned earlier, text notifications are sent to each customer and a one-hour window is given for the delivery. In addition to the overall improvements in package delivery customer service, Parcel has partnered with other companies to deliver limited-edition free items for customers. A recent gift of a free pair of Nice Laundry socks was given to customers for a week.

Even traditional postal services are enjoying what Jesse and Parcel are doing.  When asked if Parcel was seen as a competitor for services like the U.S. Postal Service and UPS, Jesse explained how what they do is complimentary to the traditional carriers. “In theory, we’re actually making the operations of traditional carriers a lot more efficient. Previously, they were making repeated delivery attempts to buildings they were never going to get inside – wasting time and money putting up missed package slips all across the city and then rerouting those packages to shipment centers or sending them back.”

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Jesse with Truck

Q: What drives you as an entrepreneur?

A: For me, it’s really about finding a problem that no one has solved before and finding the simplest, cleanest solution for it.

Parcel is just that — a simple and clean solution that has improved an outdated and unfulfilling process for both the providers (USPS & UPS) and customers. What started as an early twenty–something with missed packages has turned into a high-growth NYC startup with the potential to impact millions. Jesse Kaplan setout to solve a frustrating problem, and it’s safe to say he delivered.

Hear Jesse Kaplan deliver through the full interview audio below!

Quick-Fire Questions

–  Q: What’s your best piece of advice for young entrepreneurs?

A: Establish a really strong support system around you. On tough days or when trying to make a tough decision, it’s essential to have a network of founders, advisors, family or friends that you can call upon for anything. Starting a company is always going to be stressful and probably always going to be lonelier than other initiatives, but by having a team of people you can rely on, you can leverage that network and ensure that your experience is as positive and effective as possible.

–  How many hours a week do you work on Parcel? I think it’s probably safe to say I spend at least 100 dedicated hours a week to Parcel.

–  How many hours of sleep do you get a night? Recently, I would say 8-9 hours. It took me a pretty long time to realize that being sleep deprived did more than just make me tired. It also made me a much less effective executer and manager.

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–  What do you do in your limited spare time to relax? I’m obsessed with New York City. Any time I get I tend to wander around to different neighborhoods. Just walking around the city is one of my favorite things to do.

–  What percentage of the people you shared this idea with thought this was a good idea versus a crazy idea? The vast majority was really supportive of the idea. Anyone who had lived without a doorman immediately understood it and thought it seemed brilliant.

–  If you could add one entrepreneur in the world to your team at Parcel, who would it be and why? The best entrepreneurs often wouldn’t be great employees; myself included. An entrepreneur I really admire is Steve Jobs.

–  How can people find out more about you and Parcel? They can visit our website at

Listen to the full interview here:


About The Author

Matt Wilson

Matt Wilson is Co-Founder of Under30Experiences, a travel company for young people ages 21-35. He is the original Co-founder of Under30CEO (Acquired 2016). Matt is the Host of the Live Different Podcast and has 50+ Five Star iTunes Ratings on Health, Fitness, Business and Travel. He brings a unique, uncensored approach to his interviews and writing. His work is published on, Forbes, Inc. Magazine, Huffington Post, Reuters, and many others. Matt hosts yoga and fitness retreats in his free time and buys all his food from an organic farm in the jungle of Costa Rica where he lives. He is a shareholder of the Green Bay Packers.