Sophie Meharenna Dec 28, 2022

In our Ask A Founder series, we chat with founders about their passion, entrepreneurial path, and life outside of “work.” Here, we meet the co-founders of Paperless Post: Alexa and James Hirschfeld. Read on to learn about the birthday party that inspired this sibling duo to add more beauty, design, and intentionality to the world of digital invites.

How would you describe your brand in five words?

James: 1) Innovative: We took a different spin on invitations vs. what was out there at the time when we founded Paperless Post. 2) Artful: The brand, who we partner with, and our creative team are all focused on creating art and code, cutting paper, and painting. It’s a very creative place to work. 3) Modern: In terms of the technology we use. 4) Personal: The events that people use Paperless Post for are not always personal, but they do tend to be moments that are important; whether that’s a dinner party with oldest friends or a 50th birthday, Bar Mitzvah, or wedding. 5) Real-world: We are a digital product, but our whole mission is to help people gather in the real world in a meaningful way. We use software that helps people come together and be more connected. Everything we do is to enrich real-life interactions among our users.

Alexa: The one I had that he didn’t mention is user-centric. I think many users know we’re trying to make the best solution for them, as opposed to selling them a product. We’re on their side, we want them to look good and their event to go well. We are willing to go to unexpected lengths and focus on seemingly random product details to do so.

How do you get in the right headspace to start your day?

James: I wake up and go running in Central Park every morning; I do it every day no matter what. The process of running and elevating my heart rate outside expels any anxiety and makes me ready for the day. Then, I’ll sometimes head into the office. At Paperless Post, we have the choice of whether we want to go in or not. I like being physically in the office because going to a different space to work is good for me. I also find that riding the subway is really enjoyable. I like seeing everybody in New York doing their own thing, riding the subway, and going about their days. I find that very centering. Running and commuting to work are definitely the two main things that help me start my day in the right headspace.

Alexa: I could have a more ambitious morning routine. For me, it is all about sleep. Once I wake up with my kids, I will pass them off, sleep some more, and have a cup of coffee. Eight hours of sleep and a cup of coffee are imperative to a good headspace.

What was your aha moment for Paperless Post?

James: Alexa and I are brother and sister, two years apart. We were always close but as we became adults, we realized that we had complementary strengths. We thought that we might want to work together in some capacity. We both went to Harvard and there was a lot of innovation happening there at the time we were students. Mark Zuckerberg had just left and there was this idea that anybody could create a startup. We’ve luckily grown up in a golden era of entrepreneurship. We knew we wanted to do something together rather than traditional jobs.

The idea came to me very clearly when I was 21. Alexa and I both loved parties and believed that they were one of the best parts of life. I had a big celebration for my 21st birthday and was of course on a budget, still being in college. I wanted it to be creative and an expression of a vision I had that would be memorable. I struggled to find a way to execute this that was elevated and also expressed all of the thought and care that went into the party itself. I also couldn’t afford to send paper invites and I didn’t have people’s addresses. I needed to track RSVPs because it was a big party, so I couldn’t just send a JPEG. I thought to myself, what if we could create a platform that makes organizing an event efficient and easy, but also design tools that people could be proud of?

The options were pretty embarrassing in 2009. If we could do that, we could help consumers move this part of life into the digital era. I knew there was a way we could do it that was cheaper and more efficient than custom paper. Then we thought, how can we make it into a viable business and make it last? That is when we started to think about the “freemium” model, which is what competitors were doing at the time (and continue to do). The idea was that if we create something that is high quality, we can charge users a little money to not have ads on their invites and they would most likely be okay with it.

Alexa: James had called me with this idea, and was explaining what it would look like very specifically and also added that we would charge for it. I thought people would like it and I knew James was the right person to do it from a design perspective. I remember growing up, I would often show off James’s paintings, photos, and sculptures when I had playdates. His room was on the way to mine. I always got a positive reaction to his art. I thought it would be a lot of the same impressed reaction with Paperless Post.

James: No one would have picked us as co-founders of a tech company except for each other. We didn’t know anything about finance or business and we didn’t know what to do, but we made it work.

As cofounders, how do you make collaborative decisions on the direction of Paperless Post?

James: For me, it is about respecting each other’s different skills. I own the design and the vision and Alexa thinks about building a scalable organization. We don’t get in each other’s way. For example, I would never try to tell her how to recruit or manage a product in engineering. It is about knowing each other’s lanes and letting us each do our own thing.

Alexa: Our collaborative decision-making benefits from mutual trust and awareness of strengths and weaknesses. We don’t need to tiptoe around each other’s feelings; there are tactics for saying hard things to a co-founder, but we’ve never had to learn them.

James: Exactly, I don’t need a lesson on giving hard feedback to my sister. When you are siblings you know there is a foundation of love and respect so you don’t need to ever question that. There is alignment and trust. People often say that they couldn’t work with their siblings, but many people don’t know how magical it can be.

Describe your proudest moment with Paperless Post.

Alexa: It isn’t one big moment. It’s more day-to-day, seeing how other people use the product who I don’t know at all and the feedback we get from users. I love when I meet someone for the first time and they tell me about their experience using the product with pride. For example, there was a couple from Germany I met last weekend who were planning their wedding celebration. They were so excited about the design and to check every day to see who was RSVPing.

James: Anytime I meet users on an airplane or train and talk to them it’s clear the product has been a part of really personal moments in their lives. There are similar companies with bigger and smaller user bases, but it is the personal nature of each Paperless Post event that makes me proud. I also love when I’m in the office with the whole Paperless Post team and can see people actively working to make our vision better and greater; it makes me really proud.

How do you recharge?

James: Travel, whether that’s geographically or going to a museum to travel to different cultures through art. It’s an escape for me.

Alexa: Traveling, ideally somewhere in nature that is different from my life in New York City.

What’s one thing you wish you knew before becoming an entrepreneur?

James: How much to trust inner vision. There were a lot of moments early on where we were swayed by outsiders because they were older or investors, and we were put off course by their differing opinions. I wish I had known to trust my own vision and know that vision is valid.

Alexa: Don’t stress too much about what you can’t do. The better you are at focusing on what you’re good at, the more you are able to bring people around you who can do what you can’t. You can get great people to complement you and the work around you. The more you can specialize early, the better.

What’s your favorite form of self-care?

Alexa: Sleep. It is chemical for me. I have a protective layer over my emotions when I’ve slept enough.

James: Exercise.

What is the most powerful thing you do in your day?

Alexa: Pause, listen, and consider the other person’s opinion. That is really hard when you have your own opinion, but it is powerful.

James: Similarly for me, pause, consider, but give myself the space to look inside. Really taking the time to think through the difficult questions that I know, as a CEO, I need to grapple with and try to answer. Sometimes 90-100% of your day can be reactive, but trying to carve out the time to be disciplined, go through the things that need to be thought through, and put them down on paper, helps with the vision and eventual solution.

Thanks for sharing your story, James and Alexa!

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