The Professor Who Had Never Run a Business
Before Kyle became a speaker, he started a t-shirt company in high school. The summer before college, he got his shirts into Urban Outfitters. He was packaging inventory in the foyer of his internship office because he did not have enough room in the house where he rented a room.
Then he enrolled in BizCom 101, an introduction to business communications class. One day the assignment was a scenario: Company B owes you money. The terms were net 30. It is day 32 and they have not paid. The task: write them a letter requesting payment.
Kyle raised his hand. "This might be a stupid question, but why wouldn't you start by just calling them and asking them to pay you?"
The professor laughed. "Oh, sweetheart, you can't do that in the business world."
Kyle had just done that. Urban Outfitters was a day or two late on a payment. He called them. They overnighted him a check.
The professor had studied business, earned a master's degree in business, earned a doctorate in business, and started teaching business. She had never run a business. Kyle dropped out shortly after. Learn why TTPB exists to connect students with people who have tested the rules, not just taught them.
Why His Worst Video Got 68 Million Views
There is a picture that hung in Kyle's parents' house for 30 years. It shows his dad, his mom, Kyle, his brother, his cousins, and his uncles. For reasons nobody understands, the photographer made only his dad tilt his head. His dad hates the picture. But it is important to his mom, so it stays on the wall.
Kyle realized he could fix it in Photoshop. He recorded himself isolating his dad's head, rotating it, and ordering a new print. Then he filmed his dad's reaction when he opened the gift.
He posted the video to 17 TikTok followers. The next morning, he had a million. The video passed 68 million views.
Watching it back, Kyle noticed everything he did wrong. The footage of his computer screen was a photo of his laptop held up to his phone. He did not know how to screen record. Every P sound popped on the microphone. There were reflections in the frame.
The video had no business working. But it did. Launching an imperfect thing gives you a better chance than waiting until it is perfect. Browse jobs with employers who value action over polish.
The Hard Work That Nobody Wants to Hear About
When Kyle transitioned from youth speaking to corporate speaking, he needed to find clients who would pay higher fees. He researched other speakers earning what he wanted to earn. He typed their names into Google with the word "keynote" and a year: "Jason Mickool keynote 2019." "Jason Mickool keynote 2020."
Search results showed blog posts, event recaps, and old conference websites. These breadcrumbs revealed which organizations had budgets and hired speakers at his target level. Then he reached out to build relationships.
People ask Kyle if this method works. His answer: not often. Most people ignore the emails. Most of the rest say no. But Kyle does not need everyone to say yes. He needs 40 to 60 bookings a year. It is a volume play.
He has shared this approach with nearly a hundred other speakers. He tells them exactly what he did. Almost none of them do it. They hear "hundreds of emails" and go look for an easier way.
Kyle calls this the hard work hack. Everyone wants a shortcut. When the most efficient path goes straight up a mountain, most people look for a different route. The few who put on their boots and start climbing are the ones who reach the top. Book a speaker who can show students what that climb looks like.
How to Stand Out When Everyone Looks the Same
When Kyle needed a new speaker demo video, he studied what everyone else was doing. They all started with the speaker walking onto the stage from backstage. Big lights. Lens flare. Testimonials in the middle. Standing ovation at the end. Beautiful production. All identical.
He told his speakers bureau he wanted to try something different. The bureau president, a personal friend, said it was creative but advised against it. The standard format works, he said.
Kyle made the video his way. None of his references were other speaker reels. He pulled from YouTube videos, short films, and documentaries. As soon as the bureau president saw it, he called and admitted he was wrong. It was probably the best demo video he had ever seen.
Kyle's tagline is "The Patron Saint of Crazy Ideas." When he entered corporate speaking, established speakers told him not to use the word "crazy." They said it had bad connotations and would limit his opportunities. He ignored the advice. His second year in corporate speaking, he was the most booked speaker at his entire bureau.
The principle Kyle lives by: take the meat and spit out the bones. Figure out what works for you. Be willing to ignore the rest. The Incubator Hub is for students ready to build something on their own terms.
You Have One Life As Far As We Know
Kyle's advice to students is simple. You get one shot at this. You can look at the world and see all the problems and reasons why this is a terrible time to be alive. Or you can look at it and see that you have access to more information and better tools than the most brilliant people in history.
Crazy times create crazy opportunities. They create crazy stories. And nobody knows what they are doing. Kyle says this about himself: "I don't know how to do most of the stuff that I do. I just figure it out."
The thing he would tell his younger self: do not be afraid to put your stuff out into the world. You have no idea what can happen. Even failures often turn into new opportunities down the road. Give your ideas a chance.
What Makes a Crazy Idea Worth Pursuing?
How do you find a mentor when you cannot afford training?
Look for people who are where you want to be and offer value before asking for help. Kyle could not afford the speaker training course, so he found someone willing to mentor him directly. He did not cold-email asking for free advice. He built a relationship first. Mentors invest in people who show initiative and follow through. Start by being useful, not by asking for favors.
How do speakers get their first paying clients?
Research who hires speakers at your target fee level. Kyle searched other speakers' names with the word "keynote" and a year to find event recaps and conference websites. These breadcrumbs revealed which organizations had budgets. Then he reached out to build relationships. Most people ignored him. Most of the rest said no. But he only needed 40 to 60 bookings a year, so he treated it as a volume play.
How do you transition from one market to a higher-paying one?
Master the first market before moving to the next. Kyle spent years as a youth speaker before transitioning to corporate keynotes. The skills transferred, but he had to rebuild his client base and prove himself in a new context. He studied what corporate speakers did, identified the patterns, and found ways to break them. The transition took time and required starting over in some ways.
Does your work need to be perfect before you launch it?
No. Kyle's most successful TikTok had bad audio, screen reflections, and mic pops. It got 68 million views because he posted it. Perfection is a form of delay. Launch the imperfect thing, learn from the response, and improve from there. The market will tell you what matters. You cannot learn that by waiting.
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