October 8, 2026
Author & Personal Brand Educator
Bradley Jacobs helped build Uber Freight into a billion-dollar business. Then he quit with no plan and no idea if anyone would pay for what he knew.
So he sent twelve DMs. Eleven got no response. One person said, "That could be interesting, let's hop on the phone."
On that call, he made up his rate on the spot. The client said it was too much. He landed them anyway, and it turned into $25K a month.
I sat down with Bradley on Built in Public to get the exact playbook. Here's what he shared.
Bradley joined Uber in 2014 as one of the first few hundred employees. "It was like, 'Here's the city. Grow it. Whatever it takes.'" They could adjust pricing, message drivers, build their own funnels. Every city had their own thing. It was kind of a mess, but he learned a ton.
After two years in the rides business, he got the chance to launch Uber Eats in Miami, then Milan. "I love the chaos," he said. "They're like, 'Cool. You have six weeks to launch Uber Eats in Miami. Figure it out.'" He'd just learned two-sided marketplaces. Now he was learning three.
Milan couldn't be more different from Miami. In Miami, he emailed 1.5 million existing riders and said, "We're launching Uber Eats." Pretty easy. In Milan, there was no brand. Worse, people had a negative impression of Uber because of the government situation. So they did grassroots marketing. Subway station ads. Spotify radio spots. Things people don't think Uber needs to do.
Then came Uber Freight. He walked in and they were doing research at truck stops, interviewing drivers about their pain points, building the app from scratch. Two years later, it was worth a billion dollars. But then he hit a wall. "I got a boss who didn't like me and didn't want to promote me. It's like a whole new world I had never experienced at Uber."
One of Bradley's old bosses, who'd become a mentor, asked him a question. "Do you really want to go build a fourth business line for Uber?"
That was when it clicked. He'd always wanted to be an entrepreneur. Now was the time. "Let me just quit, take some time off." He knew he wanted to start a company, but he didn't know what it was. So he figured maybe he could work part-time for someone while figuring it out.
He sent twelve DMs to people in his network. One company was launching a food-delivery marketplace using self-driving cars. They had all the engineers, but nobody who'd actually launched a marketplace. Bradley could say, "I've done this twice, in two different international markets. I can give you the playbook."
He sent a proposal. Made up a rate based on his old Uber salary, equity value, and benefits he wouldn't be getting. The number he came up with? $287 per hour. He even pitched them a slide explaining how he got there.
They said it was too much. But Bradley had just read Never Split the Difference by Chris Voss. The one thing he took away was never negotiate against yourself. Don't come back with a lower number. Ask them for the next number. They came back with $250 per hour, plus 10% in equity. Twenty-five hours a week. Done.
"I was immediately making $25K a month. My Uber salary was half that."
When Bradley left Uber, he wrote one of those "goodbye, thanks for the four years" posts. Pretty generic. It got 46,000 impressions.
"I couldn't believe the reach. I didn't put a lot of time and effort into this post. It was the first moment where I was like, wow, the reach of this platform can be massive."
He started sharing what he was learning, what he was experiencing. Then people started reaching out. "I see what you're doing. It's interesting. Can I talk to you?" A lot of them were ex-Uber colleagues who didn't know you could consult in operations. He didn't know either.
After about ten of these conversations, he was like, "Hey, I can help you. I've learned enough. Let me give you the guidebook. Just give me a cut of your revenue for the first few months." And that became Mylance.
A big part of what Bradley teaches is positioning and niche. Don't position yourself as a fractional CMO. There are millions of fractional CMOs. What problem do you solve, and who is it for?
The pushback he always gets is, "But I can do so much more than that!" And he tells people, "You're just getting your foot in the door. Once you help them with email marketing and you see that their funnel sucks, their offer sucks, their branding sucks, their messaging sucks, great. Then you do all those things. But you have to differentiate yourself."
The way I like to describe it is like this. Imagine you're craving ice cream. You can go to the ice cream store, or you can go to a random gas station that's like, "We have corn dogs, ice cream, candy, chips, and cigarettes." Where would you rather go get ice cream? You're going to the place that's solving your problem right now.
And this doesn't have to be forever. You don't have to have this headline and this positioning forever. You can always change it. But you've got to start somewhere to get that first client. When people are glancing at your profile and they see "fractional CMO," they don't know how you can help them. But if it's so specific as "I help education companies through email marketing," and their email marketing sucks and they're an education company, they know immediately you can help.
How many do you need? You need one, then two, then three, then four. If there's 500 education startups out there, you need three of them to build a really good business.
Bradley posts every day. Has for six and a half years. "I post every day, not a single person has ever been like, 'I'm sick of your shit.'" Nobody sees every post. That's not how the algorithm works. Your audience sees a post here and there.
The way he thinks about it is that content builds trust. "I introduce myself when I connect with them, but I don't sell them or ask or anything. I let my content work. In four weeks, when I message them offering some value, I'm not a stranger."
Think about it. If you connect with a decision-maker and you're one of their 500 connections, probably only ten of those connections are posting regularly. You're going to be in their feed over and over again. Most people have very few connections posting, and less than 2% of LinkedIn posts weekly.
Bradley's best post ever was telling the story of when Uber and Lyft launched the same day in Raleigh, North Carolina. Fast forward six months, Uber had 90% market share. He detailed the four specific things that separated them. 700,000 impressions. Took him fifteen minutes to write by hand.
"It did well because it's an inside look from a first-person anecdote that you can't get anywhere else. It's numbers, it's specific, it's tangible, it's from me."
Nobody likes being preached to. Imagine Bradley saying, "You should go build your business this way. Here are the four pillars." Boring. Heard it all before.
But when he says, "I built," that's different. That Uber/Lyft market-share story? All these people wanted to hire him for their go-to-market because he'd established how Uber won. Even though it was the company, he was part of that story. So they assumed he had that knowledge and could help them.
"I catch myself still today wanting to write 'you' language, because it's not as vulnerable. It's safe to be like, 'Yeah, you should do this.' But when you say 'I,' it's a very different emotional experience to publish. But that's what people want to read."
If you can share a mistake you made, that's even better. People want to learn from you. They're not there to make fun of you. They want to hear what it's like to do what you did.
A lot of people chase engagement. What works? Personal updates. Congratulations-bait. "I got promoted." Writing about your kid, your dog, the vacation you took. A nice picture of yourself that does really well.
Bradley tells his clients, "Don't chase engagement. Go add genuine value, and trust that the right people are seeing it." A post like that every now and then is great because you're showing your humanness, which is great. People hire humans. But you're not establishing expertise in any way.
Establishing expertise is maybe a little more boring. Those posts don't do as well. But when they have a problem you solve, you're going to be top of mind. It should start happening on your calls where they say, "I've seen what you've been doing on LinkedIn." You don't have to introduce yourself anymore. That's how you know it's working.
My most viral posts make me no money. No clients, no interest. It's always that random niche post that somebody says, "How are you inside my head right now?" That's when you know.
Bradley found two things most important for LinkedIn content. It has to sound like you, not AI slop. And it has to actually reflect what you know, not what AI knows.
"If you tell Claude, 'Make me a LinkedIn post,' it's going to be like, 'A LinkedIn post is a formal business post,' and it's going to sound like a LinkedIn post." It's awful.
So Mylance pulls out the AI slop. The em dashes, the generic frameworks, all of it. There's a review layer where it drafts the post and then reviews its own work, suggests what needs to be changed. But he still tells people to read it. He spends about three to four minutes on each post now because it's learned his voice so well.
The expertise side works because he feeds it things. Transcripts from calls. Podcast episodes. His Fathom note-taker syncs directly. "This podcast is a hundred LinkedIn posts. Everything you're asking me is my point of view. So I can take this transcript, and it's learning actually what I know."
Bradley didn't think leaving corporate would be so confronting. "I have this mindset, maybe a lot of us do, these high-achieving 'Am I doing a good job?' questions. In corporate, I had all the structure. My salary band, my level, my boss, my performance structure. It's all gone."
Even when he was making good money, he'd check in with himself. Am I doing a good job? Is this okay? The freedom felt liberating but also very challenging.
So he started putting in structure. Meetings with himself on business strategy. What time he'd get up. Going to the gym in the morning, starting work at 9:00. Then he built an advisory board. People from his past who were experts in operations, marketing, sales. They'd meet once a month. He'd make a deck, present to them, have them pressure-test and ask questions. It cost him 0.25% equity across three years, and they were happy to do it anyway.
The other thing that changed everything: planning the night before. "If I wake up in the morning and I don't have a plan, it's a mess. I'll go into email, LinkedIn, Slack. I'll waste so many hours reacting to stuff." But if he writes down his top three biggest needle-movers the night before, and nothing else happens before those get done, then the day is a win.
It's actually a mental trick. Because you're not doing them now, you can put a scary thing on the list. Raising your rates, asking for the thing you've been avoiding. The big, scary, hairy task. Then in the morning, you just have to do it.
Here's the challenge. Tonight, before you go to sleep, write your top three needle-movers for tomorrow. Don't do anything else until those are done. Not what needs to get done. The biggest step-change potential if you do this thing.
Bradley's entire consulting business started with twelve DMs. Eleven went nowhere. One became $25K a month. You don't need a website. You don't need a perfect pitch. You need to show up, keep posting anyway, and trust that the right people are watching.
Do the thing.
