This Entrepreneur Is Building a Matchmaking Service for Pen Pals

Kate Dobie wants to create a hub for letter-writers. Can it work? We asked her … by letter, of course.
Hey Kate!
I happened upon your , in which you’re launching a business based on connecting pen pals with each other, and was personally hooked: I’ve had pen pals my whole life! As a ’90s kid, I used various magazines’ pen pal-connection services. Some led to friendships around the country. One led to a man in Ghana mistaking me for an older woman, and proposing marriage. (I let him down gently.) But as someone who covers entrepreneurs for a living, I admit skepticism: Is there a market for this? I can’t think of another friend of mine who has a pen pal.

So I’m eager to hear: Are there enough people out there like me, who still love writing letters to strangers? And will they pay for the pleasure?
Your pen pal,
Jason
Related:

Jason,
I’m glad we both morphed from letter-loving tweens of the mid-’90s into adults with a passion for this vital but undervalued communication form. I shared similar experiences growing up, with the glaring omission of any marriage proposals. I’d spend hours crafting the perfect letters to my new friends from exotic places like Akron and Lubbock. Anything in comparison to my hometown of 500 people seemed positively cosmopolitan.
But you raise valid questions around what potential exists for critical mass of users. I may be able to address your skepticism by having you supply the answers: Why do you, in your third decade, continue to collect pen pals? My gut tells me (because the feeling is mutual) that there’s something about the authenticity and the legacy of a letter that makes for a drastically different experience and connection. People like you and I refuse to believe that it’s social media’s world and we’re just living in it.
There’s a market for any business assembling like-minded people and creating a mechanism for them to share what they love about their involvement to their friends, multiplying the fun and evolving the community. In the case of Pens Plus Pals, we’re using some of the planet’s oldest tools and communication methods and somehow still managing to be “disruptive” about it. “SMH,” as the kids say.
My hunch, and please hit me back with your impression and instincts, is that in our over-digitized world, more and more people find themselves disenchanted or left behind.
Your pen pal,
Kate
P.S. What is the weather like where you are?
P.P.S. Do you have any pets?

Hey Kate,
Your question is a good one: Why do you, in your third decade, continue to collect pen pals? My answer: because I’m fascinated by how other people live. But I’m not attached to the medium. I wrote letters in the ’90s because, uh, it was easier than Morse code? But today, I have a pen pal in an East Asian country. Through a private, digital channel, she tells me about her customs and traditions and the super insane ways that arranged marriages go wrong. I couldn’t send her a letter if I wanted to — it’d get intercepted by her family. The medium, to me, only serves its role.
I’m about to test our fledging pen pal relationship, so hang on to your keyboard: You just dissed social media, but then said that you believe there’s “a market for any business assembling like-minded people and creating a mechanism for them to share what they love” — which sure does sound like social media to me! Is Pens Plus Pals basically (gasp!) a social media company? And if so, are the likes of Snapchat and Twitter and Facebook just updated versions of our tween-age pen pal networks, but made more accessible to all? Are we all, every one of us, already basically pen pals?
Given that we live in a far more interconnected world than we did in the ’90s, how can Pens Plus Pals offer something that people don’t basically already have?
Your pen pal,
Jason
P.S. I wore rain boots and shorts today.
P.P.S. Does a 15-month-old boy count?

Pen pal Jason,
The gloves are off! I love it.
Pens Plus Pals is 100 percent a social media network — the same as my mom’s quilting group or my dad’s bowling league. But we’d never consider comparing them to the Social Media juggernauts and I hope Pens Plus Pals can avoid that classification, too. We use our brains differently when we can’t rely on the backspace button and have to write something down. So now, the $10,000 question (literally): If you build it, will they buy?
I could go to a bar and meet a suitable man or woman but that doesn’t stop people from using matching services for ease and comfort. People will pay for things that they perceive as valuable, have a clearly defined set of what they consider “perks”, and have amazing support and engagement. That’s #goals. So being a Pen-Member means more than the initial match (or unlimited matches), it offers Pen Perks along the way including replenishing stationery and gifts every quarter, a T-shirt, invites to community events and prompts from a dedicated Pen-Mentor to keep the creative juices flowing.
Long term, I’d love all members to be able to send me a forward-dated letter (for themselves, for a friend, anyone) and we will send it to them on the date of their choosing. I’d also love to introduce a corporate-social-responsibility component where every membership means we match someone in a nursing home or homeless shelter. We can all feel good that marginalized populations still receive vital correspondence and connection.
Part of the fun is the anticipation, the absence of immediate gratification. I’ve spent eight and a half of the past 10 years overseas (China and Australia) and, sure, received emails and was so unbelievable grateful to have these modern tools to stay in touch. But when someone took the time to send a letter, man, that’s something special. I mean, I still have them. I don’t have the Snapchats or the emails.
Your dear pen pal,
Kate
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Hey Kate,
Oh boy, we’ve gone and done what pen pals do: We’ve started two separate conversations inside the same letters. In this case, the impact of a digitized world and the business of pen pals. They’re more related in your mind, I suspect, than they are in mine. Because here’s what I always think when people romanticize the old against the new: What’s more important: to do the thing, or to maintain its form? To read beautiful works of literature and ambitious non-fiction, or to only consume it on paper? To correspond with people in an intimate and enriching way, or to only send those letters via the postal service? People may prefer a certain form; I’m glad we have options! But in an age of email and social media, more people write each other than ever before. So what’s more important — for people to connect, or for them to do it in a certain way?
Your system of membership perks makes me think about what I call The Handy Problem. My wife and I used Handy to find a cleaner. A woman arrived at our apartment, we liked her and then we started paying her directly and quit Handy. There was no incentive for either party to keep using Handy, which is pretty bad for Handy’s business model. So many connection-based startups face the same problem.
Your plan addresses that. And yet! What happens once someone finds a pen pal they’re happy with and has all the pens and prompts they can handle? Online dating sites face that challenge: A happy customer is a customer no more. So I’m curious: How have you wrestled with that?
Your pen pal,
Jason

Jason,
Some things are resilient and, while being easily identifiable with a specific zeitgeist, also break beyond that to establish a firm place in our culture. We have streaming music but people love vinyl for no rational reason. (I think these are my people.) Treadmills exist and yet some people are convinced that a run in the park is preferable. So doing the thing — listening to music, running — can be heavily impacted by the form.
Discovering a letter my mom had written to me the day after her funeral — to see her handwriting and hold in my hand this tangible thread between us. That’s the significance of form.
As to the Handy Problem: On one hand, (pardon the pun) we hope to address stickiness with well-crafted membership tiers. For example, the lowest tier is a one-off match and Welcome Pack. Let’s say (worst case scenario) that match fizzles or (best case scenario) they love the service and want to take on another pen pal: They can either slide up the sales escalator to a yearly membership of unlimited matches, or just purchase another one-off match outright.
Some people will also just desire anonymity and our top-tier membership will provide that by using P+P as the go-between. Mark Zuckerberg himself can write a letter and, using us as middlemen, will ensure that his identity is safe. In this case, P+P plays an important role and we give ourselves one more safeguard from being eliminated.
With the rest of the perks, discounts, community involvement and new products that we’ll develop through a rich and ongoing dialogue with our users, we’ll hope to keep diversifying our model and give people a compelling reason to stay.
Your pen pal,
Kate

Hey Kate,
Those membership benefits are intriguing. But I started thinking: What if I don’t want a random pen pal? Then I had to pause and consider what “random” even means here. It’s not like someone can have a pen pal “type,” in the same way they might have a type of person they like to date. Compatibility means something different in pen pals. It isn’t about attractiveness or shared interests or whatever. It’s about, I suppose, whether two people fulfill a mutual curiosity — something far harder to control for. How do we know what we’re curious about, until our curiosity is piqued?
So my question for you is: How do you give people some sense of control, even as you provide them with the surprise they really want?
Your pen pal,
Jason
P.S. Here’s a question I have to wrestle with: How many more of our letters do Entrepreneur readers want? I’m going to take a guess and say … one more. Which means it’s yours to write.
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Pen pal Jason,
How I can help people “look good on paper”? That is the question I’ll being asking myself ad nauseam throughout the Pens Plus Pals journey. And, to your point, I think one of the ways we can assist our community is through tailored matches that give pen pals a great foundation from which they kick off their correspondence.
Not everyone will know what they’re seeking (much like the dating parallel that you drew) but a registering pen pal will provide us some information upfront about what they want to get out of this activity and select from a drop-down of “themes” including Inspiration, Mentorship, Kids Stuff, New Perspectives, Amor or (for the most intrepid of pen pals) Roulette.
And if the P+P community enjoys the repartee they share as much as I’ve enjoyed this exchange, then I think we might be onto something.
Your pen pal,
Kate