Sahil Lavingia, the Minimalist Entrepreneur
Today I want to do a quick recap on a few interviews I listened to with Sahil Lavingia. Sahil is the founder and CEO of Gumroad and I’ve never heard of him before stumbling on these podcast interviews, but his approach to life and work have really resonated with me. In fact I’ll happily plug his new book The Minimalist Entrepreneur which I am going to pick up and report back on.
I actually listened to two separate podcast interviews, and although some of the same themes come through loud and clear, it was really interesting to hear the different areas the interviewers probed into and it resulted in building a more complete picture of Sahil for me. Here are the two I’ve listened to:
Noah Kagan Presents -- How to Run a $100M Company Without Meetings (w/ Sahil Lavingia)
The Knowledge Project with Shane Parrish -- #98 Sahil Lavingia: Observing the Present
Sahil was employee number 2 at Pinterest and after finding it incredibly difficult to sell a simple icon online, he decided to scratch his own itch by starting Gumroad. After Gumroad went through some tough times, he wrote a very poignant piece on failure, reflecting on the lessons he’s learned through his experiences in the fast-paced Silicon Valley startup world. Ultimately this reflection allowed him to design the life he wanted: he’s retooled Gumroad to be a profitable $100M company and he’s also retooled his life to be able to put extreme focus on the things he deems important.
Figure out who you want to be, then surround yourself with similar people
In Sahil’s early days starting Gumroad, his goal was to follow the startup success formula: raise money and grow fast. Being in San Francisco’s tech scene really helped with those goals because he was surrounded by like-minded people -- everyone he met whether at a social mixer or coffee shop was driven by the tech gold rush and eager to find others that could help in their mission.
The counterpoint is also true, interestingly enough. Following his flashpoint of “failure” with not being able to grow Gumroad to a $1B company, he realized he was increasingly at odds with the vibe and values of Silicon Valley, and moved to Provo, Utah. It was only then after removing the constant cultural bombardment around him that he could think differently about his failure and pivot towards designing a life he loved authentically.
The old adage is so applicable here: you are the average of the five people you spend the most time with. I've surrounded myself with people with positive energy, and removed the toxic ones, with character traits I just don't want for myself. Or another approach perhaps - if you're hitting your head against the wall, maybe it's time to consider changing your environment completely?
Focus on things that energize you, minimize things that sap your energy
After Sahil got out of the SF startup headspace, he thought deeply about how he was spending his time. He struck on a simple yet effective system to pursue more fulfillment: spend the most time on things you gain energy from, and minimize or avoid things that take away your energy. These will be different for all of us, but for him he realized he loved figure drawing. Pretty interesting hobby for a tech CEO, no? But he takes this to the extreme -- in fact, Sahil has set a goal for himself to become one of the top figure drawers alive. How is he going to achieve this? It’s simple to him, he invests the time. He has figured out that to realize his goal, he needs to out-practice everyone else by a fair margin, so he’s designed his weekly routine to ensure he gets in hours and hours of figure drawing practice!
“People ask how the hell do you do all those things? Well I really optimize my life so I’m not stuck in meetings all day. It turns out if you don’t have 20 hours of meetings all week, 20 hours is plenty of time to build a business or write a book. 20 hours a week is a stupid amount of time. Think about any hobby… almost nobody does any hobby 20 hours a week. So if you can figure out a way to make 20 hours a week for yourself, then you can be at the top 0.1% of any activity! If you can paint 20 hours a week, you can be a master painter in 10 years.”
To clear the space for the things he loves, something’s gotta give. So he’s removed things that take away his energy. For him, one example is meetings -- and he takes an extreme stance in banishing these from his life. You’d think a tech CEO would have a calendar full of meetings right? Not Sahil -- in fact all he has made it clear to employees and investors alike that he won’t attend any meetings and as a result Gumroad has built a culture of minimal meetings, where Sahil is required at none of them! Their communication practices are all written word and asynchronous, designed around this philosophy. As a result he spends 20 hours a week at Gumroad, leaving 20 hours a week to focus on anything else he wants. One amazing byproduct of creating this culture is that he’s attracted top talent away from the Googles and Facebooks of the world who are also sick of workplaces that are meeting-crazy. See lesson #1 again :)
Meetings are just the tip of the iceberg for Sahil. It was riveting to hear him talk about how he’s used the same philosophy to spend just a few hours raising millions in capital vs the “normal” slog of a tech entrepreneur spending days on end schmoozing potential investors. He takes it a step further to manage ongoing expectations too -- he stated openly that if you’re the type of investor who wants to ask him any questions about Gumroad, just don’t invest, he’s not going to make time for that! I found his diligence in applying this principle so refreshing -- he basically re-evaluated the status quo in every situation and figured out ways to focus his time on the meaningful things while being authentic to himself. And being clear to others how he wants to operate so that he is not setting any false expectations.
I have a lot to learn in this regard. Even with a fresh start of my own, and a focus on family time and learning new skills like writing, I feel like I haven’t taken stock like Sahil has and really turned up the dial on maximizing energy. I’m excited to find ways to challenge the status quo in the same way he has!
Invest your money, don’t spend it
“I like investing money, I don’t like spending money...and I also hate things. To spend a lot of money, you have to buy a lot of physical things like houses and cars and paintings, and other things. And it just kind of sucks. Everytime you move you have to bring all this crap with you over time.”
I love Sahil’s minimalist approach to money -- he is always looking to invest his money to grow it or help others rather than spending it on things. It sounds like he actually hates buying material things, and even after rebuilding Gumroad to a $100M business, he doesn’t see the need to be spendy. In fact, I love his take -- he suggests that things are just a drag. If your life is full of these things, you need to spend time and energy to maintain them, you need to move them all if you move apartments, you need to make sure they don’t get stolen or damaged. There’s huge drag and baggage you’re creating with each of these purchases. If he goes out and buys all these things, not only does he need to spend energy deciding on what to buy, he then needs to spend energy taking care of these things, and that’s something he’s identified as an energy suck. And he’s not interested in that.
“We bought a cat… it’s amazing, it’s like a drug basically. It’s like a dopamine hit whenever you want one. And it was $50 and this thing will be 15-20 years old before it dies. What a deal! $50 for a dopamine stress ball whenever you want it for 15 years? That’s amazing!”
On the flip side, Sahil really appreciates and examines the ROI of life’s small pleasures. For example, he thinks his pet cat is an amazing use of money. He gets a ton of joy out of having a cat, expects it to live a long time, and be a companion through the years. Cat vs luxury car? You can guess what Sahil would choose.
“How can I get to a place where I can spend my time however I want? This is the first level you want to get to. And it’s not about having a million dollars. How do I get to a place where if I wanted to draw for 20 hours a week, I have the ability to. That is far more important to me than the amount of money in my bank account.”
All of these money lessons I can get behind. His minimalist attitude to spending really appeals to me, especially as I’m still grappling with my hoarding past. I really do want to get to a point where our lives are uncluttered, both mentally and physically. I want to focus my spending on things that truly bring happiness into my life. And lastly, I’m totally aligned with investing my money to grow it, to unlock future opportunities. Sahil mentions that his first step was to get closer to financial independence -- at that point the power of money is that it allows him to say no to things that take away his energy. Couldn’t agree more -- I’m all aboard that FI train!
How have I not heard of this guy before?
Wow. Sahil really blew be away. These interviews were of the rare breed that I kept rewinding and rewinding because I just couldn’t believe the words coming out of this guy’s mouth. I came away from these interviews hungering for more. His approach was just so refreshingly and unapologetically authentic, I was so inspired. In fact if I could be where this guy is at now in 5 years in terms of how he’s designed his life, that would be a huge success.
And there was so much more about his philosophy that resonated with me, too much to pack into one post. I’ll be looking forward to reading his new book and listening to more of his interviews for inspiration. I hope you enjoy his views and banter as much as I did!
