I Still Lead With Generosity. Here's What It Cost Me First.

Sometime around 2003 or 2004, I sold my Apple stock to buy a composer (who’d seen some early success writing for my first library) a new writing rig. Computer, interface, desk, chair, his own spot at the studio… the works. I'd bought $AAPL in 1999. I believed in the company. I also believed in this composer.

He never wrote another note of music for us.

I don't remember exactly what I got per share when I sold the stock. I remember that I felt there was probably future upside in $AAPL, but thought whatever music he wrote would be worth much more. And I remember that a few years later, when the iPhone era turned Apple into one of the most valuable companies in history, I did the math on what I'd sold. I've never fully forgiven myself for it—not because of the lost windfall, but because of what the decision revealed about how I was operating.

I was extending my generosity based on feelings and hopes instead of running my business investments based on facts.

I've been building production music catalogs since 1996. We founded The License Lab in 2011, and have released over 600 albums across ten labels in the 15 years since. I’ve co-written/produced over 12,000 songs at last count, and have successfully exited/sold three prior complete catalogs to Warner/Chappell, Zomba/BMG, and Sony/ATV. I tell you these bits not to brag, but because what I'm about to describe isn't the story of someone naive to the music business. It's the story of someone who kept making the same structural mistake while getting better at everything else.

Here's the short version of that mistake, told in a few different ways :

• I once offered free studio space to an artist so they could record and produce their own podcast. They used the space, never even said thank you, then went on their podcast and explained that the reason they didn't make records in town was there were no top quality producers or studios. You can bet I heard about it.

• I offered free studio space to an electronic duo in exchange for some creative work. They never followed through on their end... not helped by an untimely hard drive failure. I never followed up, because I felt awkward about it, because we had mutual friends.

• I introduced a composer to two international industry events and a major streaming playlist curator—opened every door I had. They joined forces with one of them right after the event and never wrote for us again. Never said thank you, either.

• Early in my career I built a new label concept for an existing business partner—new brand, new direction, my ideas freely given. When I left the company, they sued me for ownership over what I'd created. I'd been generous with everything… except the paperwork.

• A writer we took a chance on and hired through a work release program started sharing company intel with a private industry group on Facebook. I found out the way you always find out… from trusted peers, but too late.

• I invested years in an artist, without pay. Poured real creative energy into their music, into their career. I heard them in an interview one day describing our work together, and my contributions were... minimized. Not maliciously, I don’t think. Just casually. The way you minimize something you've stopped valuing.

• One of my first projects as a fledgling producer was a spec deal I worked out with a talented local cover band, and we utilized a local studio that had a bunch of open slots on their calendar. I came off tour a day early and dropped by the studio to unpack some gear only to find the studio owner working with them directly, having wedged himself into the deal and cutting me out. They never paid me (I had agreed to charge them a whopping… wait for it… $10 an hour). Even though I still have that handwritten invoice (this was the early 90s!), I hadn’t prepared an official agreement with them that would hold up to legal scrutiny, let alone mitigate any disagreement or misunderstanding.

• I once sold my car to pay three staff composers. Not because someone wronged me, but because I'd built a system where generosity had no floor.

Here's what all of these have in common, and it took me longer than I'd like to admit to see it clearly : I thought these people were my friends.

Not business contacts. Not collaborators. Friends. People I'd extended real trust to, real resources, real belief. And in almost every case, when the relationship ended those people were just... gone.

A few of them were genuinely malevolent. Most of them, I think, were just ordinarily self-interested in the way humans tend to be when they want what you've built but don't quite believe you when you describe the years it took to build it. That's its own kind of pain… not betrayal exactly, but a fundamental mismatch in how you understood the relationship.

I kept extending friendship-level trust to people I only had a business relationship with yet. That's the mistake. It sounds simple. It took me a long time to truly understand.

Here's what I do differently now, and I want to be clear : I haven't gotten less generous. Generosity is core to how I operate and I'm not interested in becoming someone who hoards their resources and their connections out of misguided self-preservation. That version of this business, and this life, doesn't interest me.

But I've now tried to put architecture around my generosity.

Before anything meaningful exchanges hands—studio time, introductions, creative work, setting up a writing rig—there's at least an email exchange that walks through what happens if things go sideways. Not a threat. Not even a contract, necessarily. Just a conversation : here's what I'm offering, here's what I'm asking in return, and here's what we'll do if scenario A, B, or C plays out. Most people respond well to this. The ones who don't respond well to it are usually telling you something important.

I've also gotten better at leaning on the people who've known me longest—family, lifelong friends—when someone new comes into my orbit. Not because I can't read people myself, but because I've learned that my enthusiasm for a new collaborator can outrun my judgment. The people who love me don't have that problem.

And I've built in probationary periods for relationships that matter. Not necessarily formal ones. Just an internal understanding that trust is extended incrementally, not all at once.

If you're building a production music or sync catalog, or really anything in the music business or adjacent to it, you're going to be taken advantage of. I want to say that plainly. The earlier you accept it as a condition of doing real work in this industry, the less it will cost you when it happens. And it will happen.

What you can control is the architecture around your generosity. What agreements exist before the exchange. What conversations happen before the trust. What signals you're willing to act on before the relationship gets expensive.

I still lead with generosity. I still believe in the people I work with. I still get it wrong sometimes.

But I don't sell the stock anymore before we've had the conversation and come to an agreement.