Reid Hailey Jr. and the second life of a joke

Reid Hailey Jr. once used Instagram to wind up friends who took Instagram too seriously. It is a pleasingly modest beginning for a media company. Before the golf clothing, the acquisition discussions and the CEO title, there was an account called ShitheadSteve. The name did not suggest that anyone would eventually need a general counsel.

Hailey started the account in 2014 while taking college classes and living in his parents’ basement. Within roughly a year, it had a million followers. People he had never met were laughing at material made under an alias. A private sense of humor had acquired a public, and the public kept growing.

The interesting part of his career is the change in his own job. Making the next joke became one responsibility among many. He would have to find other creators, support their work and decide what an audience might want beyond another post. Doing Things, the company he co-founded with Derek Lucas in 2017, grew around those questions.

Four friends, a basement and a bad name

Hailey grew up in suburban Atlanta and described himself as the classroom nuisance, making strange noises with friends. “I’ve always been that guy in classes making weird noises with my friends,” he said in 2020. His decision to attend the University of Alabama had a similarly social logic: four close friends were going. The company was good, even if the academic plan proved temporary.

He left Alabama. There was also a short-lived attempt at an on-demand maid service. Before he settled into a career connecting comedy and commerce, he had tried a rather more literal form of doing things.

The basement account offered an immediate kind of feedback. A caption either caught someone’s attention or disappeared into the feed. In his early work, the apparent casualness concealed a time-consuming routine. By 2016, he was spending hours looking through hundreds of images, hunting for pictures that could carry a joke.

That detail is useful. The finished meme asks for almost none of the viewer’s time; the search for it can consume most of the maker’s day. Hailey was learning to recognize the small opening between an ordinary picture and an observation someone would send to a friend. Repetition supplied a practical education in taste.

The Illuminati had a group chat

Lucas was making memes, too. Their meeting place was an Instagram message thread called the Meme Illuminati, where creators exchanged ideas and helped promote one another’s accounts. John Mayer joined the conversation. The conspiratorial name was doing rather more work than the conspiracy.

The chat mattered because its members were useful to one another. A creator could supply a picture, improve a line or introduce someone else’s account to an established following. They were developing a shared practice before they had a shared company. Collaboration happened in the same medium as distribution.

Hailey and Lucas formed Doing Things in 2017 after early advertising work for brands including Gucci and Hinge. Lucas moved to Atlanta the following year. Their partnership gave each person’s instinct a larger setting: several accounts, different audiences and a business that could sell more than a single sponsored post.

There is a temptation to treat the group-chat origin as a charming preface to the serious work. It contains a good deal of the operating idea. Find people with a distinct comic voice. Learn what their audiences enjoy. Give a new piece of work a useful introduction. The company would eventually add more expensive obligations, but it had already learned how to make a recommendation travel.

A company with very little face

Much of the portfolio’s appeal comes from recognizable habits. Middle Class Fancy, acquired in 2018, developed recurring suburban characters such as Rand and Nance. Lawn care, familiar family rituals and small domestic obsessions supplied material. The pleasure is often recognition: someone sees a parent, a neighbor or an inconveniently accurate version of themselves.

Recurring characters also give a feed continuity. A viewer returns knowing the sort of joke that belongs there. Another viewer learns the references from a friend. Each account needs its own judgment about what to repeat and what has become tired. A large network cannot make that choice once and apply it everywhere.

Hailey’s own interests in comedy included Dave Chappelle, Adam Sandler and the Good Neighbor Stuff videos. Yet as Doing Things expanded, he spent less time tending individual pages. By 2020, he described a working life focused on building the company, consumer products and original shows, while still making a meme when an idea occurred to him.

“Look at their engagement before looking at the audience number.”

Reid Hailey Jr., 2023

That advice captures a recurring concern in his business thinking. A following can look impressive while revealing little about whether people return, talk to one another or care about the account’s next move. For a company hoping to make products and experiences, those behaviors carry more information than a large total beside a profile picture.

His role leaves room for a curious kind of anonymity. The brands can be widely encountered while the person running their parent company remains less familiar. For Hailey, the work has increasingly involved arranging the conditions in which somebody else’s voice can be heard.

The joke needs somewhere to go

Original shows gave that arrangement a more demanding test. In 2019, Doing Things backed Andrew Callaghan’s All Gas No Brakes. An early discussion over pho in New York led to a practical request: an RV. The company’s initial commitment, including equipment and production support, was about $50,000.

The partnership combined a creator’s interviewing style with the company’s money and existing distribution. Clips could be introduced across other accounts. The experiment carried an appealing possibility for Hailey: a network built around short jokes might help launch entertainment people would choose to follow in its own right.

The relationship ended in 2021. Callaghan and his team went on to Channel 5 after a dispute with their production partners. The separation belongs in the story alongside the launch. Supplying support and agreeing on what a creator should own, earn and make are continuing responsibilities, even when a show finds an audience.

By September 2026, Hailey was discussing creator incentives, the use of audience data to refine shows and the choice of properties that might expand into other businesses. These are the questions of a person whose job has moved beyond finding the next funny picture. A successful launch supplies a new set of decisions.

When the audience leaves the house

A public post from Hailey about a Breezy Invitational at Cantigny Golf Club in the Chicago area contains a particularly good business detail. Fat Perez made a hole-in-one near the end of the tournament. Someone also proposed at the awards ceremony. A media executive’s event recap had acquired the outline of a wedding speech.

Hailey thanked the creators, team, partners and fans who attended. His enthusiasm had something concrete to attach to. People who knew Bob Does Sports through a screen had spent a day together in person. There were sponsors and commercial arrangements involved, but there was also an experience that participants could take home.

Breezy Golf apparel makes a related connection. Golf entertainment supplies an audience interested in golf; clothing gives that audience something it can use while playing. The fit between the activity and the product is easy to understand. The company still has to make and sell the clothes, but it begins with a reason for customers to pay attention.

Doing Things’ March 2026 recognition on Fast Company’s social media innovation list focused on products and events. Five core brands had merchandise businesses. The company had also helped launch the 2025 Internet Invitational golf tournament. These developments give Hailey’s early interest in turning a social presence into products a visible, physical form.

Taking the joke seriously

For years, the company grew without outside funding. In February 2022, it announced a $21.5 million Series A led by Volition Capital. Hailey said the original plan had been to continue growing organically and profitably; the investor relationship changed that calculation. The stated uses included expanding brands, creator relationships and direct-to-consumer commerce.

Overheard joined the portfolio in early 2023. Combining the teams took a full year. That is a revealing interval in a business associated with instant reactions: an acquisition can happen much faster than the everyday work required to make it function.

December 2024 reporting put Doing Things’ gross revenue at almost $40 million, compared with $10 million in 2021. Those are company figures, with all the people and costs that a company entails. Hailey’s advice to creators had become suitably practical: find business expertise, invest in a team and take the longer view.

Today, Doing Things lists more than 40 brands and over 95 million followers across its portfolio. The total counts follows across accounts, rather than distinct individuals. Hailey’s own story makes the individual relationships more interesting anyway: the friends he teased, the collaborators he met, the creators he backed, the people who arrived for a day of golf.

The first account let him make a joke and see who laughed. The CEO’s job asks him to decide what is worth building around that laugh. Sometimes the answer is another show. Sometimes it is a shirt. Occasionally, at an awards ceremony after a golf tournament, somebody decides the occasion is suitable for a proposal. Even a media plan should leave room for that.