The Defiant Ones: Lessons for Makers and Investors

Available on Netflix

Available on Netflix

If you’re a startup founder, artist, investor, or anyone working on something hard, you’ve got to watch the HBO/Netflix documentary about Jimmy Iovine and Dr Dre. It’s not just about the music business either. The 4-part series is an extended biopic about two incredibly talented individuals who we think we know from their craft. Yet, by the end of the series you realise you did not know them at all.

If you watch the series you’ll come away inspired and appreciative of Jimmy Iovine and Dr Dre’s perseverance, creativity, and not least of all, humanness. Both of these guys worked super hard to get to where they are but they were also lucky. They messed up a bunch of times but they also sought redemption. And despite the extraordinary success of these individuals, the documentary shows that no one is immune from the rumbles and tumbles of life.

For all that, I enjoyed this documentary so much that I watched it twice. Along the way, I noted down quotes I found pertinent for my current field of work (venture capital and technology entrepreneurship) and have been meaning to post this blog for many weeks. Below I highlight some of these quotes with commentary but this is certainly no replacement for watching the series, which I highly recommend.

Investors: it’s not about you.

There’s a section in the series where a young Iovine, new to the studio and his role as a supporting record engineer, is complaining about how hard he had to work for the artist Bruce Springsteen, while at the time having nothing to show for it. At one point, and after endless and fruitless studio seasons, Iovine is ready to quit. But the co-producer Jon Landau interjects:

“Jimmy, you’re missing the big picture. What are we here for? We are here to help Bruce make the best record he can. That’s the job.

We’re not here to make you happy, we’re not here to make me happy. We’re here to contribute to the project and it’s Bruce’s project.

If you go back in and say to Bruce, ‘I’m here to support you. This is not about me, its about the album,’ you will have a friend for the rest of your life and you will have learned a big lesson.”

The relationship between a record producer and an artist is like that of an investor and entrepreneur. One helps the other in the process of creating something new. But its never about the investor or whoever is supporting the maker. Good investors—and as it happens, good music producers—know this. Here’s Dre:

“Every producer knows that you’re only as good as the artist that you’re working with, because that artist could either make or break you. No matter how great your track is, the artist that you’re working with or the writer that you’re working with has the ability to make it magic or fuck it up.”

Simply put, good investors support the entrepreneur and aim to do everything they can to help founders build the best businesses possible. It’s never about the investor. It’s always about the business.

Extraordinary success is impossible without luck.

Dre and Iovine had a few of lucky breaks that snowballed into unimaginable success. Such is life. The Matthew Effect—“for unto one that hath shall be given, and he shall have abundance”—is always at play.

Indeed, a small turn of events can completely change the course of your life. For example with Iovine, it was being called into the studio on a Easter Sunday to answer phones. Unbeknownst to him he was being called in because an assistant engineer couldn’t make it. Iovine skipped the festivities at home to go to the studio and to his surprise, the recording session was for none other than John Lennon of the Beatles.

Dre had similarly fortuitous breaks (watch the documentary and see if you can spot them) and what’s clear is that though hard work is necessary for success, it’s never sufficient. You always need the occasional blessing from Lady Fortune.

That said, hard work positions you well to benefit from opportune moments. Patti Smith, a punk rock singer/songwriter who also worked with Springsteen, illustrates this point with her recollection of why she chose Iovine to produce her album. Bear in mind Iovine wasn’t a well known producer back then. In fact, he’d just been fired from a previous gig. But Smith saw something in Iovine that won her over. Here’s what she had to say about him:

“I didn’t care whether he was liked by Foghat [the English rock band that fired Iovine as their producer]. He made an impression on me immediately. If Bruce [Springsteen] wasn’t there working, he [Iovine] would stay for hours and study other people’s mixes, other albums. He’d find some old tape to see if he could improve that. He worked all the time.”

During this period Iovine had actually made a promise to himself about his music production career:

“I said to myself, no fun, no life, no nothing. You’re gonna give up everything and put 100% into this!”

As venture investors we’re always looking for people who are as determined as Iovine and Dre. But a lesson here is that we should also look for entrepreneurs who have a propensity to be lucky.

This is not to say that you can accurately measure someone’s propensity for good fortune. But I have found that people who are luckier in life tend to have large diverse networks, insatiable curiosity, and an experimental approach to life that is driven by small tests and doubling down when a winning opportunity presents itself (I cover some of this in chapter 13 of my book, which also has a brief luck-driven origins story on Felix Dennis—a canny entrepreneur who amassed a £400m+ fortune.)

There’s no doubt that hard work is necessary in competitive fields, particularly in entrepreneurship and investing. But to win big you absolutely need luck on your side. Dre sums it up nicely in the documentary:

“As far as me and Jimmy goes, we just some lucky motherfuckers man.”

If you don’t humble yourself, a flop will.

In the startup world we often chime that for a founder, a startup is like their baby. Which is why I found this comment from the music manager Alonzo Williams amusing:

“Records are like children. You never met a mother with a ugly baby, okay? I never had a flop. They just wasn’t as popular as the other ones.”

This made me chuckle but it also reminded me of how the art of creation can blind you, particularly if you’ve had a streak of successes in the past. Sooner or later market forces can hand it to you, so it’s important to stay humble. As Dre put it:

“There’s nothing more humbling than putting out a fucking flop.”

Do something you can be first in.

Most people don’t know this but Dre was once a breakdancer. He is also an ex-boyband member. Both of these pursuits frustrated him though because he wasn’t great at either. Here’s a conversation his mum remembers:

“I used to tell him you can’t have no job pop-locking. You need to find you a job. And he was always coming in second. And I remember him saying that he needed to do something he could be first in.”

This all changed when Dre discovered the art of DJing. As soon his ears latched onto what you could do with vinyl, he was smitten and immediately knew what his calling would be: to become a DJ and ultimately a hip-hop music producer, something he could be first in. Beats By Dre and all his other ventures came much later.

Innovative creators and high performing investors often launch their careers by curving out a niche that they can be first in. Eminem did it by owning freestyle rap battles. Google did it by focussing on search. Warren Buffet did it by mastering value investing. This strategy isn’t the only way to do things but it works with sufficient regularity to make it worthwhile.

Don’t let success breed complacency.

The founder and CEO of Intel, Andy Gove, once quipped that success breeds complacency and complacency breeds failure.“Only the paranoid survive,” was his motto. You don’t have to take this message literally but if you are a maker or investor that wishes to excel, these parting words will bode you well:

“You gotta work hard to get it, twice as hard to maintain it.” – Dr Dre

“Treat everything like it’s your first opportunity.” – Kendrick Lamar