Choose Your Own Way

Prince is considered one of the greatest musicians to ever live, with a discography that includes 7 Grammys, 5 number one albums, and decades of hits.

Prince was 18 years old when he made his first album, For You. He turned down several major studios before signing a deal with Warner Brothers, after Prince’s manager, Owen Husney, convinced the company to sign Prince to a three album deal, the largest record contract ever given to such a young artist.

According to Prince, Husney also played an important role in the production of For You. In an interview with Musician magazine in 1983, Prince shared Husney’s philosophy:

“Owen believed in me, he really did, he shared. “The main thing he said to me was that no one should produce a record of mine—I should do it.”

And produce is what he did. The album credits on For You say it all:

“Produced, arranged, composed, and performed by Prince.”

Despite the conciseness of those credits, the actual process of making the album was anything but easy. The studio attempted to take shortcuts, but were met with the defiance of one of the most unique artists of his generation, who wanted no shortcuts. It took seven painstaking months to finish For You, What transpired was an exercise in trusting one’s own judgment, and demonstrating a singularity of purpose.

First, Prince was given a budget of $180,000 to produce three studio albums. However, given his desire for his first album to be absolutely perfect, he spent nearly the entire budget ($170,000) on the making of For You.

As a result, with money on the line, and as large record companies like Warner Brothers often do, they stepped in and attempted to commandeer the process by asking veteran artists and producers to guide Prince through the making of the album.

Warner Brothers wanted Maurice White of Earth, Wind, and Fire fame to produce the album, Prince said no. Warner Brothers then brought in Grammy award winning producer Tommy Vicari to produce and engineer the album, and deliver a hit as he had done in the past. Vicari suggested they record the album in Los Angeles, because that’s where everyone was making records. Prince said no. The album ends up being recorded at The Record Plant in the Bay Area.

At the studio, Vicari suggested they bring in other musicians. Prince said no. Instead, Prince sang every vocal, played every instrument, and recorded every note on the entire album. Vicari continued to make suggestions about what to play, and Prince again said no. When they start mixing the album, both Vicari and the studio told Prince not to play any additional instruments over the recorded songs. Prince said no. After overdubbing a ton of layered guitar, the album ends up with the signature Prince sound that he would become known for throughout his entire career.

Once the album is finished, the studio hires a photographer to do the cover art for the album. They make a bunch of suggestions, and Prince said….you guessed it…no. He instead hired his own photographer, and together, they made this iconic album cover.

For You achieved a sound only Prince could create, as he played a whopping 27 different instruments and perfected the execution of each one. Because he recorded every aspect of the album himself, Prince tapped into a new approach and sound that would lay the groundwork for the so-called “Minneapolis Sound” — a style of music that Prince would catapult to global fame in the early 1980s.

Prince was the ultimate auteur, who demonstrated a strong singularity of purpose throughout his life and career. Trusting his judgement is what shaped his work.

The life of a stock picker should be long. There will be iterations of your process, strategy and framework. Early on, you may find yourself placating to others, or making decisions based on borrowed conviction. Over time, you eventually realize, like Prince, that the only person worth impressing is your future self, years from now, looking back at the decisions you made and evaluating whether you had the courage to follow your instincts, stay committed to your process, and stay the course when it mattered most.

Trusting your own judgment doesn’t mean you’re always right. It means you’re willing to be wrong on your own terms. It means you’re willing to carry the weight of your decisions and stand behind the work. It means that if you fail, you fail because of you, not because you deferred to someone else’s framework or preference.

That’s the game. Not beating the benchmark. Not outperforming in this or that quarter. The real game is finding something you believe in—and then refusing to let go. It’s what separates the hobbyist from the professional. The technician from the artist. The analyst from the investor.

I’ve repeatedly asked myself a few useful questions to get to the heart of how strongly I trust my own judgement.

• Do you trust yourself enough to hold the thing you like, even when no one else does?
• Do you trust yourself enough to let your biggest winner keep compounding, even when every model and talking head says it’s overvalued?
• Do you trust yourself enough to build a track record that reflects you, not the investment equivalent of a corporate committee?

Just as Prince ignored the "correct" way to make an album, there is no single "correct way" to invest. Investment decisions, at their core, are creative pursuits that rely on trained intuition and experienced judgement. They are an expression of how you, the investor, view the world and what you believe will create value. The ways to execute a creative pursuit are as follows: the correct way, and the way you like.

Contrary to popular belief, most musical artists don’t make music for their fans. They make music they like, and then decide to share it with the world. Whether other people like it is irrelevant. It’s great if they do, but it’s not why the music was made. The artist is expressing something, a belief, a sound, a vision, and executing on it. It doesn’t matter whether anyone else likes it.

The delineation between the correct way to do something and whether you like it or not has roots in investing. There is no ‘correct way’ to invest. I’m often amazed at the ways I see some of my peers sustainably make money.

Yet, every step of the way, throughout your investing life, there seems to be this constant tension from others regarding what investors should do. The types of companies, liquidity, securities, position sizing, valuation, simple versus complex, short term versus long term, and more.

I remember pitching my first idea to a more experienced PM many years ago, and when the idea was met with questions, I folded like a chair. I was trying to get him to like my idea. That was the wrong approach. I already liked it, and was just sharing it with him due to its attractiveness. Whether he - or anyone - agreed with me was irrelevant. In fact, unless you are pitching a low quality business that is likely to destroy capital, most investment discussions or debates come down to preference and time horizon.

The best place to arrive as an investor is the moment when you stop defending your ideas altogether because you’ve done the work and have confidence in yourself and your thesis. This is what trusting your judgement looks like.

The Prince story is one of my favorite stories about creative pursuits. There is no map to follow. There is no right answer. With Greystone, I’ve adopted the one-man shop approach. All investment decisions run through me as the lead analyst and PM. It works for me, as I have a vision that I am trying to execute on. My view on investing is that investment decisions are to be made independently, not by committee. Group discussions, lengthy meetings, bureaucracy and long decision loops all detract from solid, long-term investment decisions.

That doesn’t mean I don’t collaborate with people. I’m constantly exchanging ideas, pitching interesting stocks, red-teaming a thesis, and looking for disconfirming evidence from other smart people. I’m not suggesting operating in a vacuum. But how could Tommy Vicari or Maurice White or Warner Brothers possibly hear what Prince heard? How could they bring to life his way of seeing the world?

When I meet with potential investors, I'm very careful to explain that Greystone is the vehicle I use to execute my vision. They don't have to like it or agree with it, and many don't, but it's my vision. Building an investment business and an investment portfolio is about taking pieces of yourself - your background, experience, interests - and bringing them to life. Again, there is no right answer. All investors are tasked with developing a connection between their ideas / portfolio and the way they see the world. That connection has to last through everything, and there are ways to develop and improve it. 

• Make Mistakes and Refine: The path to good judgment is paved with lessons learned from both successes and failures. Embrace your mistakes as opportunities for refinement.
• Develop a Clear Vision and Purpose: Understand why you invest and what kind of investor you aspire to be. This clarity provides a compass when navigating uncertain markets.
• Gain Experience: There's no substitute for hands-on experience. Putting risk on the table, making buy/sell decisions, and living with the consequences is the only way to truly learn. Being an analyst, while valuable, doesn't inherently prepare you to be an effective portfolio manager.
• Do the Upfront Work: Conviction isn't born out of thin air. It's the result of diligent research, deep understanding, and a well-thought-out thesis. The more work you put in at the inception of an idea, the stronger your conviction will be.

Maybe there is a universe where Prince’s first album, done his way, flops. I bet he could have lived with that. Success someone else’s way isn’t rewarding. Failing doing something someone else told you to do is even worse. Prince went to great lengths to protect his vision, likely before he earned it. He’s not the only one. This is the hard way to do it, but the best way. The thing you make, build, construct, whatever it is, needs to be something you like. What you like comes from your judgement. Exercise it often, and learn to trust it.

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