My first investment

Twitter Question. Answered.

In 2010, I wasn’t an investor. I was a founder, but an opportunity presented itself that I couldn’t pass up. My first investment was in company called Path. It was a bit of a Silicon Valley darling: founded by Shawn Fanning (Founder of Napster), and Dave Morin (Early Facebook Product), and Dustin Mierau. Path was the private social network for mobile. It was like Instagram in concept, but not in ethos. I did not make money on Path, but looking back, Path was the perfect investment for me to learn from and build a network on. In many ways, that was the beginning of Boost VC, I just didn’t know it.

In 7th and 8th grade - I can neither confirm, nor deny, that I had downloaded music illegally through a product called Napster. And I can neither confirm, nor deny, that it was one of the first products that catalyzed my understanding of how powerful the internet was. So you can imagine how excited I was when I showed up to a pitch meeting 10 years later and Shawn Fanning walked in and sat across from myself and my Dad…(you don’t bring your dad to your pitch meetings? I must be doing this wrong)

I remember almost everything about the meeting, which is wild, because I can’t even remember what I had for dinner last night. I remember the first thing that Shawn actually talked about was Spotify, this hot European startup that he was advising.

“When I was at Napster we always talked about how we might be able to bring everything to the cloud one day.”

He said that he could get us beta access, and that all you had to do was log in through your facebook account.

And then he pitched Path. Looking back, the idea was still so early. Basically it was “The mobile phone is going to be the largest platform for social media…” all of the things he said, ended up being true. I listened, but it didn’t really matter what he said - he could have just said “Poop” for 30 minutes and I would have invested my money.

“And so, which of you wants to invest?”

I raised my hand. Like a kid in a high school class who wants to show off that they know the answer. I raised my hand.

Something that I didn’t realize at the time was that I would need to have an LLC to invest out of. There’s a lot of history to that fact, but basically a Limited Liability Company (LLC) separates you as an individual from ownerships in companies. There is an amazing book about it. I wanted the name of it to be something super cool… something that was like a super hero… but also something that made me sound anonymous… something like “Ghost Angel LLC.”

So I set up an LLC for $200 using RocketLawyer.com. I then wired money to Path and suddenly I WAS AN INVESTOR!!!!

I wasn’t really sure what an investor was supposed to do after that, so I emailed the two founders and asked if they would want to meet up and talk about the company, now that I was an investor.

This is when I met Dave Morin. I went up to San Francisco and we went to a nice dinner. Dave is purposeful and controlled when he talks. He was very design focused, he reminded me of a good friend of mine. I felt we got along very well. Facebook had recently gone public, and I’m pretty sure he was crazy jazzed about that.

Here is where we get into how Path was the perfect investment for me to start my journey. What a lot of people don’t realize is that every investment ends up being a micro-network of people who are aligned. I went to every Path party they hosted and I got to hang out with amazing people building things.

Matt Van Horn, the head of Biz Dev at Path, connected me to Justin Miller at a Warriors game. Justin has become a dear friend of mine for the last 10 years, who I have also invested in twice.

I met Logan Green from ZimRide when he was raising $1m to get his new product “Lyft” off the ground. I think of Lyft as one of my investment misses, because I remember thinking “This guys is awesome.” but it was at a party, so I wasn’t sure if I should propose investment in a loud room.

At another party, it was all the Path investors, and they all seemed to know each other. Ron Conway, Rob Hayes, a bunch of other amazing investors. The first round of Path was raised at a $20m valuation. I didn’t know if that was high or low, I just said yes. They ended up with a party round of investors, fantastic people.

I know Ron Conway, because he’s my friend Topher’s Dad. Which is probably how a lot of people refer to me when I show up to a meeting with my Dad: There’s Tim… but which son is that? Is this one Billy? I think Billy is the older one? Taller one?… this one looks younger…

Man that’s probably super annoying for Topher if he reads this.

I remember at one point I brought up Strava at a the party, one of my friends had recently taken a job there and I wanted to hear their opinions. There was a hot debate around the room about whether or not the market was large enough. Strava is going public this year.

I’m rambling a bit now because it’s fun to reminisce. Through Path I encountered Spotify, Lyft, Strava and those are the deals I didn’t do. I would also meet life long friends and founders I would invest in. I was able to enter the conversation with investors around other investments… I also got to witness a silicon Valley darling that didn’t end up working out.

My investment in Path showed me the importance of aligned networks and showing up. Which are good lessons to learn. I showed up to everything and then I just kept showing up.

Did I stick the landing on this one?