From the Flight Deck to Plus 1:
the story behind founder Jeff Wulkan.

There are millions of people who want to do something. They just don't always have someone to do it with.

— Jeff Wulkan, Founder & CEO of Plus 1

For more than 20 years, Jeff Wulkan spent much of his life in the air.

As an airline captain, he traveled the world, led crews, made decisions under pressure, and regularly landed in cities where he'd find himself asking a surprisingly simple question: what should I do tonight, and who can I do it with?

Jeff had always been an entrepreneur. Over the years, he launched multiple businesses, created a wine brand, wrote a best-selling memoir, and even founded a barbershop concept that gained national attention on television in 2012.

But entrepreneurship had always existed alongside his first passion: flying.

Plus 1 would be different.

It started with a canceled date

The idea came in 2025 after Jeff landed a hard-to-get dinner reservation in Miami and made plans to go on a date.

Everything was set. Then, just a few hours before dinner, his date canceled.

Jeff still wanted to go. The reservation was difficult to get, his friends were busy, and he started thinking about his options.

He could post the reservation to his Instagram Story and hope that, among all his followers, someone happened to be nearby, available that night, interested in the restaurant, and willing to join him.

He could open a dating app and start swiping. But he wasn't necessarily looking for another date, and even if he was, how long would it take to match with someone, get a response, have a conversation, and figure out whether that person was free that same night?

Then there were platforms built around events and group meetups. Those were great if he wanted to find an organized event or join a larger group, but that wasn't what he needed either.

He already had the plan. He just needed a plus one.

That's when something clicked.

Why wasn't there a simple way to post what you already wanted to do and connect with someone nearby who wanted to do it too?

Not necessarily for a date. Maybe a friend. Maybe a business connection. Maybe someone completely outside your normal social circle who just happened to want to do the same thing.

A one-on-one dinner. A round of golf. Drinks after work. A workout. A last-minute concert. Or a small group getting together for something spontaneous.

The plan should be the starting point.

A problem he'd already experienced around the world

That canceled dinner reservation wasn't an isolated experience. It connected to something Jeff had encountered throughout more than two decades of traveling.

He'd arrive in cities around the world surrounded by thousands, sometimes millions, of people, yet still have no efficient way to find the few people nearby who wanted to do the same thing he did.

Maybe his coworkers were tired after a long day. Maybe they didn't drink. Maybe they wanted to stay at the hotel while he wanted to explore the city.

Of course, there were ways to meet people. Social media could broadcast something to people you already knew or who already followed you. Dating apps could introduce you to potential dates. Event platforms could help you discover organized events and larger gatherings.

But Jeff saw a gap between all of them.

What if you already knew exactly what you wanted to do and simply needed someone to do it with?

There wasn't an obvious place to say: here's what I'm doing, here's when I'm doing it, who wants to come?

The people were there. The plans were there. The connection between them wasn't.

That became Plus 1.

Going all in

Jeff had built businesses before, but Plus 1 became the first company he decided to go all in on.

In some ways, his previous career had prepared him for it more than he realized.

Being an airline captain isn't simply about flying an airplane. It's about leadership, preparation, communication, managing a team, assessing risk, and making decisions when the pressure is high and the answer isn't always obvious.

Building a technology company requires a very different skill set, but Jeff found himself relying on many of those same instincts.

There's also something fitting about someone who spent much of his life traveling eventually building a company centered around bringing people together.

Because underneath all the technology, Plus 1 came from a very human observation: there are millions of people who want to do something. They just don't always have someone to do it with.

Your friends might be busy. You might be new to a city. You might be traveling alone. You might want to try something none of your friends are interested in. Or maybe the person you were supposed to go with canceled at the last minute.

Jeff believes none of those things should mean you have to stay home.

His vision for Plus 1 is to make meeting someone through a plan feel as natural as ordering a ride or booking a restaurant: decide what you want to do, put it out there, and connect with someone who wants to do it too.

Because sometimes a great friendship, relationship, business connection, or simply a night you'll remember starts with two people saying the same thing: "I'm in."

After spending more than two decades helping people get from one place to another, Jeff is now focused on a different kind of connection: helping people find each other.