How a Joke Landed a $30K Client in Austin (and Can 5X Your Pitch)

This week's Founder Friday is about a founder who treats humor as more than entertainment. JaMarr John Johnson — who calls himself the Entrepremedian — has built a business around the idea that laughter can open doors, build trust, and make sales conversations feel human again.

For business owners, the lesson is simple: better communication makes you more memorable, more trusted, and more effective in the room.

Here's what JaMarr shared...

You're known as the Entrepremedian. What does that mean?

Well, if you go to Urban Dictionary, what it basically means is it's an entrepreneur who understands, at the core of his business, that humor is a tool to lead people with levity. It's also a super connection tool that really aids in business development, sales, and the marketing process.

How does that turn into an actual business?

So I have four core pillars of my business as a performer.

I keynote speak, I do corporate comedy (corporate events), and I fundraise for companies. I've been doing that for two decades. Actually, the first time I was on stage was in front of about 2,000 people at the Waldorf Astoria Hotel in New York City, and in attendance was Kofi Annan. I was speaking on behalf of a nonprofit called Facing History and Ourselves. 2,000 people, you're raising a bunch of money. I think a little over $2 million was raised that night. Not all by my part, but I played a role in that. So I've always made sure that service was a part of how I operated my business. Those are the four pillars for performing.

Now, on the other side of the business is business development. I used to be a CMO of a company. I used to work in Silicon Valley, and what I was doing as an inside salesperson translated into business development. I was able to take my skillset as a comedian, go out in the world, make people laugh, entertain them, and then also make connections. Those connections blossomed into really big opportunities.

For example, I used to work at a cloud-based accounting company, and the average recurring revenue client was about $6,000 a year. Well, when I went out into the world, did my thing, and connected with people, I brought in a $30,000 a year client from one of the connections I made while I was out performing. I realized it's the same concept as if you had sweet seats to a game and you took clients to that game. The exhilaration, the cheering, that's bonding people with their clients.

Why is that so special in this day and age?

Well, I think everyone watches the Super Bowl, and what are the commercials that we remember? The ones that make us laugh, make us feel emotion. For me, humor growing up was a skill set that I developed out of pure defense mechanism. It was a survival tool. And then years later, I learned that there was big business in being funny, and I started to explore all the ways in which humor helps people generate more money.

Can you explain why Austin? What's so special about this place?

Yeah, so I was living in Los Angeles for nine years before I moved out here. Part of it was reading the tea leaves, but a big part of it was thinking about where I could go where there was this incredible intersection between technology, entrepreneurship, spirituality, and comedy. Those were the four things I was looking at.

I came here and visited during South by Southwest with an old mentor and friend of mine in 2022. He gave a keynote, and I just checked out South By for one day. Then I had some other friends that lived in Austin and had been here for years. So I came back on a couple of other occasions just to get the vibe of it. And what it gave me was like a not-as-mature San Francisco, but almost like my old college town. I went to Auburn University in Alabama, so it gave me that college town with a tech vibe.

And then of course, there were rumors that Joe Rogan was going to open up a big comedy club here. I was thinking about how his podcast expanding impacted the comedy scene in LA. I was producing shows at the Comedy Store, filling up a 60-seater at 10:30 at night in the belly room. And then eventually Joe Rogan's podcast kicked me out of the belly room.

In thinking about how rising tides can raise all ships, I thought it would behoove me to get to that third coast so I could ride some of the wave of what's going to happen with comedy and business. And honestly, we met, we did a show together, the Side Hustle Live show, and there's been a proliferation of comedy-slash-business type shows that have been popping up. It makes sense that it would happen here. Even though some of these shows are taking it on the road and doing stuff in New York and LA, the energy for me feels like it's here in Austin and it will be here for the next five to ten years. And if you're a smart business person, you've got to look at where the tide's going. You've got to see things before they happen. And you've also got to go someplace where there's no state income tax.

Are there any recommendations you'd have for Austin business owners?

Oh yeah, some easy ones. I would say first, get into the event game. Whether you sponsor someone else's event or host an event, there are so many moments of capture that can happen when you create environments for people.

The next thing I'd say is commission a funny advertisement for your business. I've always known that comedy and humor were important to marketing, but the best example I can give is Squatty Potty. I remember seeing that organically and sharing it with at least a dozen people just because I thought it was the funniest ad I'd ever seen. Another guy I used to speak at his mastermind, Billy Gene of Billy Gene Is Marketing out of San Diego, he did some spoofs of Wolf of Wall Street, and I think he did a Willy Wonka spoof too. You get so much extra lift when people find your advertisements funny, and when you can take a couple shots at yourself and a couple shots at your competition without necessarily naming them. You're able to address some elephants in the room.

I think a funny piece of content shows that your company isn't full of themselves. And then those two things together: live events where you're getting around people, getting real feedback, actually connecting with your customers, and then making content that's actually interesting and funny. It creates a shareability that you can actually measure now with all the tools we have. You can see how many times things are shared on Instagram, for example. A funny piece of content can go a long way because it's reusable, and every time you're about to have another meeting with someone, you could send them a link to that funny piece of content to bring some delight to their day.

Can you talk about how humor helps with pitching?

Yeah, that's the one other really important thing. Whether you're fundraising or trying to enlist support from people, being able to nail your pitch and your purpose is one of the most important things. When you can do it succinctly, with a little bit of humor, you don't need to become a standup comedian tomorrow. But being able to have control and command of an audience, those skill sets really translate into a bigger business. People basically invest in who they believe in, who they feel is confident, who commands a room.

I remember a couple years back, I got hired to coach a speaker who was trying to raise some money. I helped her raise $50,000 in a grant because she had to go present. And I have a good friend of mine who's a two-time TEDx speaker, a former Colorado Buffaloes offensive lineman, and he used to be an advisor at Techstars. Combined, he helped raise $250 million between all of the founders he helped improve their pitching, and that wasn't even with humor. That was just, "Here's how to become a better, more effective communicator." If you add humor to it, that little special sauce, now you're talking about breaking records, like what Jo Koy and Fluffy just did at SoFi Stadium. They sold it out.

So comedy and humor is big business, and learning how to wield it effectively will make you not only a better communicator, but more liked, more loved, and more trusted.

Are there any Austin-specific people, resources, or communities that you found particularly helpful in growing your business and your career?

Well, I'd be remiss if I didn't give a shout out to Toastmasters as well as BNI. One is a nonprofit, one is a for-profit, but they've impacted me in many ways. When you can show up and give really effective, short, succinct, witty, funny pitches, you get people's attention. You make people want to know more.

When I first came to Austin, I didn't know anybody, so I was like, "Okay, let me get involved in some local events." I checked out a couple of meetups, but for me, I went and checked out the Austin Toastmasters Club. They have multiple clubs, so no matter what part of town you live in, there's a club probably close by. I went to a couple BNI meetings, and from there, when you're a super connector, people are always inviting you to more and more stuff.

Beyond those two, it's hard to give specifics because I've been to so many different places. But I would say having the ability to effectively communicate what you do in the marketplace is probably one of the best things you can do. And finding places where you can share that message. People don't realize how valuable going to a Chamber of Commerce meeting is.

Do you have any tips for people wanting to connect more?

Yeah, so I've got a couple of models that I talk about in my book, Super Connecting, as well as my course. One of them is called FORM. It stands for Family, Occupation, Recreation, and Motivation. A lot of times when people get together, they talk about, "Where are you from? What do you do for work? What do you do for fun?" Those are the core three that get people talking. But when you ask people about their motivation, like what inspires them, what they feel their purpose in life is, you start going into territory where they don't usually get questions.

It makes them pause, makes them stop, makes them actually think for a minute. And the types of responses I usually get from people are, "Wow, I've never been asked that before." At that moment, they're thinking and feeling their own feelings about what they're doing in life. Is it meaningful? Is it purposeful? And now you're going into that deep water of really connecting with them. So I would say FORM is probably one of the easiest things you can do. And it's not formulaic. You don't have to always start with family and then go to occupation and then to recreation. You can do it in different ways. But forming people is a really strong way to create a powerful connection that gives you really good information on which to follow up with them and how you can help them, serve them, and connect them to other people.

And then beyond that, I'm big into lyrics. I've been a poet my whole life, a spoken word artist. I've won some poetry slams. When I know what motivates people, I think about the music that connects me to that person and the lyrics in particular. Then I'll send them that track on YouTube, or I'll pull out a specific lyric from a song and share it with them and say, "Hey, this reminded me of you." People appreciate when you think of them. And when I think of people in the moment, I try to always share. And I love that now with the iPhone, you can send later. So even if it's 1:30 in the morning, you can still send a text and just set it to send at 9:07 AM.

Is there anything I should have asked that I didn't?

The other thing I'd say from a business development standpoint that I'm really excited about: I partnered up with a company a couple months back to help me with my business around data. Obviously there are tons of opportunities to speak all around the country, but finding the ones that meet the criteria for which you are best suited can be difficult. Now I have access to a database of almost everyone in the United States for intent searches. What that's done for me is, let's say I've got 50 targets that I'm aiming for in the next quarter that I want to speak at. I can use that data of those potential speaking engagements combined with intent data to find out who's really on the verge and retarget those people, remarket to those people.

But that applies to almost every other business, because every business needs to be doing the same thing: finding potential customers and staying in front of them. With the data I have access to, I feel like I can really help other aspiring speakers or business owners who want to speak to expand their business. So mastering data and business development around getting in front of really good opportunities to get on stage and speak. Right now, I've got 500 leads in my tank. There's no way I could serve all of them. So finding other people who might want to speak and matching them up with those would be a great thing to do.

That's what's going to help me stay more in Austin. Because now I'm aware of everyone who's looking for a speaker, large or small. And while the speaking business is a $5 billion a year industry, the training business, which is secretly a much bigger business, is a $360 billion a year industry. Companies are looking to bring in people to help their employees get trained up, be more efficient, and do more with less.

Where can people learn more?

Check out entrepremedian.com — that's the hub for everything, including comedy, speaking, and upcoming work.

Connect with JaMarr on LinkedIn.

Starting in May, JaMarr will be doing a residency at Golfinity Austin at least twice a month, including networking events, trainings, and business development sessions built around helping people connect, communicate, and grow.