Entrepreneur James Hirschfeld is the co-founder of the online invitation business Paperless Post, through which 80 million invitations were sent last year. Its users have included Kirsten Dunst, the Obama Administration and, it is rumoured, Prince William and Kate Middleton for Prince George’s christening. Hirschfeld has been listed in the “30 under 30: Forbes’ Most Powerful People on Earth”. Now 32, he chats to me about his business tips, the hardest part of working with family, and the most popular design for cards.
Is this your first time to Sydney?
Yes, though I have been dreaming of visiting Sydney since I was a child. I was raised by an English nanny who followed her husband to Australia when I was four. I remember crying hysterically when she left for the airport and dreaming of flying to Sydney to live with her, especially when my parents punished me.
What is a day in the life of you?
I’m fairly regimented during the week. I live in New York City … My day begins with a three-mile [five-kilometre] run around the park. I get to the office by 10.15, where I split my time between focusing on business strategy, company communications, design, brand and business development. I get home at 7.30, order dinner and typically watch a movie unless I have a dinner engagement.
How did the Paperless Post business begin?
It fittingly began with a party. When I turned 21, I threw myself a big party in Boston, where I was studying. It was the dead of winter so I made the theme “beach club”, I filled a historic house with 80 palm trees and built cabanas with disco balls in them … But when it came down to sending invitations, there was no digital product that reflected the care I put into the event. That’s where the idea was born.
What is the best part about working with your sister, Alexa?
The best part of working with Alexa is celebrating successes together. It’s really nice to be able to share the fruits of your labour with someone you love. Also, we can communicate very efficiently.
What is the hardest part of working with family?
Switching it off. It’s tough being at a family dinner with your co-founder and not letting work creep into the dynamic.
What are you doing while in Australia?
I’m totally thrilled to be in Australia. I came with three intentions: firstly, to get a better feet on the ground understanding of the local culture and tastes. Secondly, I wanted to promote Paperless Post in one of our fastest growing global markets. Finally, I was here to speak about the importance of diversity in technology at the [recent] Vogue Codes conference.
You have re-established the standards of modern correspondence. Did you ever envision that Paperless Post would become so big?
I really don’t think we could have imagined where we’ve gotten in 2007, when the idea first emerged … I started Paperless Post when I was  and at the time I kind of thought the business would be all about 21st birthdays, because that was all I knew!
Kirsten Dunst used it for her 30th birthday party, the Obama Administration for events during the 2012 re-election campaign and, rumour has it, Will and Kate for Prince George’s christening. What has been your biggest pinch-me moment?
Actually, it wasn’t a famous user. Two years ago I was travelling from Greece to Italy. I had to take a tiny ferry from the island where my family spends the summer to a bigger island with an airport. On the ferry boat I struck up a conversation with an older Italian couple who told me they had used the product for their daughter’s wedding. Then, on the flight, the man I was sitting next to had used it for his father’s 70th. When you meet really random people and they have a personal connection to your product, it’s pretty surreal.
Why do you think sending “special” mail online and in paper form is so popular?
People like to know that others are thinking of them. Special mail takes time to send and usually has more personal value for the receiver. Who doesn’t like receiving invitations to parties?
What is the most popular card design and why?
People really love designs where they can add their own photo – I think it makes the design more personal.
Do you have a motto?
“Parties are only as fun as their hosts.”
How do you switch off?
I am borderline addicted to running. I start every morning with a [run] – it clears my head and gets rid of anxiety.
What do you like to do in your spare time?
Go to museums, go to music festivals, get people together for dinner at my house.
Where do you see yourself in five years?
I hope in five years I’m doing what I’m doing now – helping people connect in the real world more easily and more meaningfully, but on a larger global scale!
Where is your favourite place to travel?
Greece. My mother is Greek and it’s where my family goes every summer for vacation.
What was your childhood like?
I grew up in New York, which I loved. I had one foot in New York culture, the other in Greek culture because of my Mum’s family and the amount of time we spent in Europe. Growing up in the city is pretty competitive and intense and you grow up fast, but I’m lucky to have a very supportive and loving family.
If you hadn’t gone down this career path, what would you be doing?
Probably running a different start-up!
What advice would you give to someone starting his or her own business venture?
Find great co-founders who can balance your strengths and weaknesses, and roll with the punches.
We went to Bondi Icerbergs, Bondi
We ate Fusilli all’Amatriciana di Mare Fusilli with Crystal Bay Prawns, Spicy Amatriciana Sauce & Pangrattato; Insalata alla Terzini with Gem Lettuce, Radicchio, Oregano & Sharp Lemon Dressing; Piatto di Salumi with Shaved Salumi, Olives, Pickles & Grissini
We drank Mineral Water
Photograph Fairfax Media