I posted on two job boards. Not the free ones. The ones that cost real money to put a listing on, the ones where the people who actually check them are looking for something specific. The post said up and coming artist seeking management and linked to my Spotify and socials. I kept it short. If they needed more than that to know whether to apply, I didn't want them anyway.
Three days later I had a stack of responses. I narrowed it down to three interviews and booked a room.
Not a conference room in someone else's building. I'd leased a small office space downtown, nothing big, one room and a waiting area, 3k a month. It felt like the right move. I still had about 23k saved but I was spending on business now — lawyer fees, the office, equipment — and that felt different than spending on myself. Spending on yourself runs out. Spending on infrastructure is supposed to come back.
The morning of the interviews I parked the Z out front and a guy walking by stopped and asked if that was my car. I said yeah. He asked for a picture. I said sure. It was weird because I wasn't famous, not really, not outside the city, but here people knew the car and they knew the name and it felt like something had shifted without me noticing exactly when.
I went upstairs and sat in the office alone and texted Maddy.
you up
Maddy: obviously its 10am
what are you doing today
Maddy: nothing why
USC game tonight. come
Maddy: i don't care about football
i know
Maddy: ...fine
Maddy: what time
She was replying faster than usual. I noticed that and didn't say anything about it.
I put the phone down and looked at the room. One table, three chairs across from me, a bottle of water on each side. I should have had someone with me. I called Savannah.
* * *
She showed up twenty minutes later in black slacks and a fitted blazer with her hair pulled back. She looked like she'd been doing this for years.
I told her straight: she was my assistant. Official, on payroll, real title, real money. More than the market rate because I needed her close and I didn't want it to get complicated.
She looked at the room, looked at me, and said, "Okay."
That was it. No questions, no negotiation. Just okay.
She sat down next to me and pulled out her phone to take notes. Then she said, almost as an aside, "Seven says she likes your music by the way. She thinks I'm cool now for being around you."
I laughed. "Seven's got good taste."
"Don't tell her that, she'll never let me hear the end of it."
The first candidate knocked. I told her to send him in.
* * *
Simon was maybe fifty-two, fifty-three. He came in with a firm handshake and a folder and the kind of confidence that comes from having been in rooms like this for a long time. He knew the industry. He talked about artist development and long-term brand building and relationship cultivation with labels, all the right words in the right order.
The problem was the music. I asked him what he'd been listening to lately, what had caught his attention in the last year. He named three artists that were big five years ago. When I mentioned the direction I wanted to go — not pigeonholed, not a street rapper, range across moods and sounds without losing the throughline — he nodded like he understood but his eyes were doing the math on a different formula.
He wasn't bad. Just not for me.
I told him I'd be in touch with my decision. He shook my hand again and left.
Savannah wrote one word on her notepad and turned it toward me: Next.
* * *
The second one was a woman, maybe forty, named Patricia. She'd worked with a mid-size management firm for twelve years and had a decent track record on paper. She was more current than Simon — she knew the names, the trends, she'd done her homework on my stuff before walking in, which I respected.
But she was hesitant in a way I couldn't work with. Every answer had a qualifier on it. Every idea came with a reason it might not work. Not because she was being careful, but because she wasn't confident, she didn't want to be wrong out loud.
I needed someone who was sure before the proof was in.
I thanked her and walked her out.
* * *
The third one came in and I knew in the first thirty seconds she was different.
Her name was June Harris. Twenty-five, maybe twenty-six. She walked in like she'd already decided the meeting was going to go well and was just there to confirm it. Not arrogant, just settled. She sat down, put her folder on the table without opening it, and looked at me.
"I've been listening to the EP since it dropped," she said. "All three tracks, multiple times. I wanted to make sure I had something real to say before I came in here."
I nodded. "And?"
"Hard to Choose One is going to be the one people remember. But Dead Man Walking is the one that's going to make the industry take you seriously. It's the most technically interesting thing on the project and most people won't even be able to explain why. They'll just feel it."
I kept my face neutral. She was right and I wasn't going to give her that yet.
"Tell me about your background," I said.
She'd started working for a talent manager named Derek Cole when she was eighteen. She told me his name and watched my face. I didn't react but I filed it. I'd look him up after.
"I started as basically an intern," she said. "Got coffee, handled scheduling, sat in on every meeting he let me sit in on. By the time I was twenty I was handling artist communications. By twenty-two I had my own clients inside his roster that he let me run point on. I know how deals are structured, I know how labels think, and I know what they're going to try to do to you if you walk in without someone who understands the playbook."
"What are they going to try to do?"
She didn't hesitate. "Lock you into a long term deal with a low royalty rate and a 360 clause before you know what your ceiling is. They're going to use the trial buzz and the streaming numbers to make the offer feel urgent. They want you signed before the next project drops because they know the leverage shifts after that."
That was the right answer. That was the exact right answer.
"What would you do about it?"
She leaned forward slightly. "I'd take the meetings, let them feel like they're close, and use the competing offers to run the price up. Then I'd push for a shorter initial term, better royalty splits, and a hard out on the 360. And I'd do all of it before your next round of meetings, not after."
I looked at her for a second. She held it.
"You said you had ideas," I said. "Beyond the deal structure."
"XXL Freshman consideration in the next cycle if the streaming holds. You have the narrative for it — the trial, the comeback, the EP dropping right after the verdict. That's a cover story, not just a blurb." She paused. "Power 106 out here is the right first radio push. I have a contact there who owes Derek a favor and Derek already said he'd pass the reference along."
She slid a card across the table with Derek Cole's number on it.
"Call him," she said. "He'll tell you who I am."
She stood up, picked up her folder, and smiled. Not the kind that needed anything back.
"You'll know by next week," I said.
"Thank you," she said, and left.
I sat back. Savannah was already looking at me.
"She was the best one," Savannah said.
"Yeah."
I pulled out my phone and looked up Derek Cole. He'd worked with Trippie Redd, Ruth B, and four or five other names I recognized from different corners of the industry. Not a legend. But real. Consistent. The kind of manager who kept working because he was actually good at it.
If he vouches for her, it's her.
I put my phone in my pocket, told Savannah good work, and went home to get dressed.
* * *
I put on something clean and picked Maddy up at seven.
She came out in jeans and a fitted top with her hair down, which she knew I liked even though I'd never said it. She got in the car and looked at me.
"You look nice," she said.
"You too."
She pulled her seatbelt and looked out the window. "I still don't care about football."
"I know."
The stadium was loud and crowded and she spent most of the first half taking pictures. Not in a bad way. She just liked the shots — the field, the crowd, the lights. She posted three in a row and tagged our location and I saw the comments fill up before she even put her phone down.
I told her "next time don't post it until we leave she said ok sorry"
In the second quarter she leaned into me a little, not much, just enough that I felt it. She didn't say anything about it. I didn't either. I watched the game and she watched her phone and at some point her shoulder was against mine and it just stayed there.
On the drive home she had the music low and her feet up on the dash and she was half-asleep by the time I pulled onto her street.
I parked and she sat up slow and looked at me.
"Tonight was good," she said.
"Yeah it was."
She got out without saying anything else. I watched her go inside.
I drove home and thought about the way she'd leaned in. I thought about how she hadn't moved away. I told myself I was probably reading into it just because I liked her. That was the easy explanation.
I wasn't sure it was the right one.