Inside the rise of sibling entrepreneurs

Paperless Post started its life as an e-commerce business that focussed on design-led online stationery - greetings cards and invitations that you could personalise to suit you. With now over 1.5 million registered users, the New York based company has become a huge success. It was founded by James and Alexa Hirschfield, in 2008, when they were just 23 and 25 years old. We spoke to them to find out how they managed to transition from brother and sister into sibling entrepreneurs.

With over 85 million cards sent since its launch, Paperless Post has experienced a fast-paced growth. Unlike anything on the market at the time of its conception, James explains how the idea came for their company first came about.

"We started thinking about Paperless Post in 2007, when I was still at school. I had put a lot of effort into planning my 21st birthday party, but found that there was no way to invite people online that reflected the amount of care that was going into the event. All emails looked the same, and the existing products for sending invitations online lacked the beauty and customization available in paper stationery.

"We set out to create Paperless Post as a way to bring that kind of design and personal touch to communication in this medium."

At that time, older sister, Alexa, was working in the city and made the decision to leave her job to pursue the dream that she and James shared.

"I was working in Katie Couric’s office at the time, but once we decided to pursue the concept for real, I quit my job. I was working on Paperless Post full-time from my parent’s living room for a year and a half before we finally unveiled the beta version of the site to our friends and family."

To date, the company has now received around $12.3 million in funding from investors, including Thrive Capital and the Crunchfund – with other investors still keen to get involved. But did their own outset as partners in a business come quickly to them, and was it easy for them to fall naturally into different roles?

Read: The pros and cons of running a business with your brother

"I have always oversee everything on the design side," explains James. "From the cards themselves to the company branding, while Alexa manages all of the technology and product needs."  This is an assumption which Alexa notes people are quick to "make the other way round", as the sister in the partnership.

The latest move for the start-up is an exciting one – an offering of actual paper products, which customers are able to order online. Both have said that although their original idea was based on electronic communication, they have listened to what their customers are asking for. 

I asked them about their own relationship with each other – having worked so closely on a personal and business level for the last eight years. Do they have tips for anyone out there looking to run a company with their sibling? James speaks of their natural bond as brother and sister.

"The level of trust that we have in each other is something that would be difficult to replicate with another co-founder. Not only are we siblings, but we’ve always been especially close and tuned into each other’s heads."

And does Alexa agree with her brother?

"Yes, we know what we can implicitly trust the other person about and what we can’t. Such a deep level of awareness of each other’s strengths and weaknesses is a huge benefit of working with a family member.

"There is also a forgiveness and understanding that’s incredibly helpful in the difficult times that are bound to happen when you’re starting a company."

And so what lessons do they have for others from their experiences running a start-up like Paperless Post? Alexa kindly shared her top tips that she wishes she had given to her younger self, about both work and life alike.

  • Don’t waste your time doing anything you don’t love – there are too many things you will love that you cannot justify missing out on.
  • Don’t be so hard on yourself.
  • The discipline comes in paring life down to what you are really passionate about, and not adding things just because you can.

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