6 min read

How Matt Mazzeo Got His Start by Doing Free Work

Matt Mazzeo, managing director of Lowercase Capital, advises young people to add value to portfolio companies of firms they want to work for, instead of just asking for jobs. By doing free work and offering value, you can make yourself stand out and potentially land your dream job.
How Matt Mazzeo Got His Start by Doing Free Work
Photo by Ian Schneider / Unsplash

Matt Mazzeo is the managing director of Lowercase Capital. He and his partner Chris Sacca find, back, and support early stage teams across the startup landscape.

You’ll probably recognize some of their investments:

Lowercase Logos

According to Fortune, their fund’s overall return multiple on committed is around 216x.

Or, in dollars, nearly $1.3 billion on about $6 million in call-downs.

Or, in simpler terms…

Lowercase is the best performing VC fund of all-time.

Before Lowercase, Matt was an agent at Creative Artists Agency, helping clients at one of the largest entertainment and sports agencies build businesses in tech.

In a recent interview on Product Hunt, Matt discussed the best job hunting strategies for young people, and how he got his start by doing free work. Readers of Recession Proof Graduate and students of Land a Job You Love are already familiar with this strategy. This methodology helped me land dream jobs with Tim Ferriss (first full-time employee), Tucker Max (movie tour videographer), and Ramit Sethi (book marketing team) when I was 22 years old.

Below is a partial transcription of the interview, from 40:19 – 49:00. Emphasis mine:

“Stephen is a 15-year-old, in ninth grade, who built Lowercase Jobs on an off-day. He decided to spend a few hours of his time — or God knows how much of his time — collecting all of the job sites that exist for Lowercase companies, publishing them to a website that was branded with Lowercase. He didn’t ask for permission. He knew it would be valuable and posted it out.That’s amazing hustle and it’s a huge value provision.I’ve given this advice to a few people, even principals or associates at different companies. If there is a firm that you want to work at, or a partner that you wanted to be your mentor, identify their portfolio companies. Then start adding value to those portfolio companies. Just reach out. Literally just deliver whatever value you can. Find a way to say to them:“I don’t need any payment. I don’t need any recognition socially, with the exception of if you would say a ‘Thank you’ in your next investment update, that would be hugely helpful.”If your name kept appearing in my investment updates, I’d be like “Who is this human being that’s delivering more value than half of the cap table? That’s incredible!” You can start doing that now. You don’t have to ask permission. You just go and help all of those portfolio companies. I would make that case:“It turns out I’m of service already to your portfolio. I’d like to do even more, and make it my full-time job. Hire me.” That would be an interesting pitch…Just being in the room is a good way to start. If I were starting out in tech, the way that I would do it today is to just go work and mentor and apprentice under a great founder. People always say, “Just hustle down a job! Hustle down a company and you’ll get in!” I’m going to be very, very specific. Let’s say you want to work at a startup.I believe a startup is the best place when you are really young to get your hands dirty. To add value and have your age not be a detriment, but an asset to you. And the most important thing is to find somebody to apprentice under. If I were trying to work in startup land, I would look at all of the companies in the last six months to a year that had raised seed or series A funding. I would make a list of those companies, so you can go to Crunchbase, Angellist — wherever you want to find it. Make a list of those companies and the cities they are in. Be okay with the cities they are in. Be flexible. You might want to move to one of those cities if you find the right company. Make a list of the missions of those companies. Identify the mission, and if you love the mission, then make a list of the founders. Determine which of those are sort of seasoned founders. Then make a list of the VC’s, and which VC’s you thought were respected. And now you sort of hedged your list.Identify which of those companies has the best mission. Something you are going to brag about to your family, that you are going to be bragging about. Bragging is actually a great metric. You want to feel proud of what you are working toward.Find a company whose mission you want to brag about, and start thinking about how you can add value to that founder’s life immediately.Do a project for them. Put together a list of customers for them. Start talking about them in publications. Whatever is in your toolkit that you can add value on, do it. Then reach out to that founder in an email that says: “I love your company, I love your mission. I am more passionate about it than anything in my life. I want to come and apprentice under you and work with this company. And I will add more value than you’ve ever seen. Here is the work that I’ve already done. I believe in the future of your company, and I will work harder and further than anyone that you’ve ever hired to improve the life of that company. I don’t care where you put me, I will find a role and I will be affordable and a star for you.”Give examples of exactly what you have done and what you will do in the future. And if you can get a warm introduction to that person, even better.”

Sound familiar? This is almost a word-for-word script from the Gift lesson in Land a Job You Love.

Here’s how Matt got hired and became an executive at the CAA, the most powerful talent agency in Hollywood:

“The CAA gig was funny. I was interning for a guy named Milan Pertel, who had a production company here in LA. And I was just the most obnoxious human being. I took home every contract that he’d ever written and came back on a Monday morning on the first week of my internship. I was 22-years old, and I’d highlighted all of the terms that I didn’t know. And I said, “Hey, I read everything, can you teach me what I’m missing? He was like, “Sweet god… I’m getting you out of this office.”He got me a job working for his old boss at CAA. I kind of did the same thing there. I failed miserably at my first desk job. I crashed my boss’s car on the first day. I somehow starting working with Michael Gello, Richard Lovett, and Michael Rubel. They let me apprentice under them.I was good at writing PowerPoint decks.I was lousy as an assistant, but great at writing PowerPoint decks. And they kind of just let me keep doing it. The first one I got to write was Funny or Die, when I was 23-years old or something. They just let me go off from there, because that was actually a skill that I had. I was just writing decks all day long. Turns out it’s still a good skillset to have. I spend a lot of time with companies today writing up their pitch decks.I didn’t know what I was going to do, though. I had the belief that the right path would be one that opened me up to as many opportunities as possible. The business development group sort of sat on top of all business divisions at CAA. While the company was quintupling in size and starting a sports group, a digital group, an office in India, an office in China, and all these different things… I got to see the 30,000-foot view of the entertainment world.I knew that the learning would be valuable, and I just needed to stick right in that spot.Back then, nobody cared about digital, and that’s what I loved doing. I was super into all of the tech blogs, so I just sort of made that my niche. I was cheap so nobody cared. Timing was perfect for me. I got lucky.I wish that I could say this was all a planned trajectory. None of it was planned. It was heads down. “What’s the opportunity right now? Am I building more, am I learning more? Am I heads down about the projects that I am excited about? Am I passionate about them? Do I have good mentors who have my best interests at heart? Am I part of a growing organization that’s exciting, that I feel proud to work at?”