Who is Startup L. Jackson?

If you like startups and you’re active on Twitter, chances are you’ve heard of (and love) Startup L. Jackson. For years, (s)he’s tweeted his/her candid — and often humorous — take on the startup industry behind a veil of mystery. According to SLJ, only a few dozen people know of his/her identity. We’re excited to have this mystery person as a Product Hunt LIVE Chat guest this Friday, September 4th. You can join in on the conversation here:

We caught up with SLJ recently to ask a few questions of our own leading up to the LIVE Chat. The world may still not know the true identity of the person behind the Twitter handle, but we now know a little bit more about him/her. Read (and listen) on for more of the conversation.

Your blog is called “Startups and Shit.” You clearly know about the startup community. That’s why people are always guessing, “Who is SLJ?” Sarah Buhr wrote a TechCrunch article with some hypotheses about who you are.

Those are always awesome because I get compared to some amazingly smart people. I’m very flattered. I don’t think people are making good guesses. It’s awesome to see what people are coming out with. I’m not Ben Horowitz; I love Ben Horowitz, I wish I was Ben Horowitz. That would be about the coolest thing in the world because that guy’s blog is amazing, and that guy is so smart. I’m not Hunter Walk, not Dustin Curtis. Keep guessing. :-)

Are you ever going to come out [with your identity]?

It’s one of those things that’s inevitable at this point. Early on, it was kind of an open joke. The company I was with at the time…a lot of people there know [it’s me]. So it’s actually not a well-kept secret, it’s just that no one who works at TechCrunch knows. I’ve always found it funny. To me, it’s a commentary on the state of tech journalism. I’m pretty sure if someone took a week and said, “I’m going to figure this out,” they could.

How many people know your identity?

I would say it’s on the order of probably a couple dozen [people]. It’s not a tightly held secret. But, it’s more fun now to have it be secret than have it be out.

Was there a moment when you thought Startup L. Jackson could be a voice in Silicon Valley?

That’s not what I set out to do. I just set out to have fun. It was entertaining — I laughed at it. In my day-to-day, I spend a lot of time interacting with companies and people who are in the startup scene. I walk away from some of those meetings thinking, “Man, I just want to make some passive aggressive statement on Twitter.” I’m not going to do that because [people] will be offended, but the great thing about SLJ is you can say these things and those people will retweet you. That’s entertaining to me.

Have you had startups ask you for advice or funding?

I have [been asked for] both of those things. I’ll tell you one story without naming names. I was talking about certain aspects of platform strategy, and had a founder of a multi-billion dollar company DM me and say, “Hey, do you want to grab beers? I’m thinking about this problem.” So I met up with the dude. We talked about startups, and what he was trying to do, and some of the platforms I’ve worked on in the past. I don’t know if it was useful for him, but it was entertaining for me.

What would SLJ invest in?

Invest in shit that isn’t stupid. Go find good startups, go find people building good shit, and good things will happen. Simple thesis [laughs]. All the investors out there are like, “It’s not easy.”

What’s on your phone home screen right now?

I’ve got Gmail for my email, and Sunrise as my calendar app. I’m old school — I don’t use Spotify. I’m the only person who uses iTunes Match and thinks it’s alright. I’ve got Google Hangouts…I like communication apps: ReChat, Twitter, Facebook. Techmeme is my go-to app to start my reading for the day. I read Fred Wilson’s blog. I’m a big fan of Nuzzel. Occasionally, I check out Hacker News — I just don’t read the comments there.

I have to give a shout out to Techdirt, which is a really underrated tech blog. Gigaom, also. I think a lot of people read the stuff that’s about the people as opposed to about the businesses, and they read more stuff about consumer tech than about enterprise. So, I try to get outside the TechCrunches of the world — although, they do some good stuff, too. I’ve been playing around with a health app. I’ve got Automatic for my car. I also use Nest and Lockitron.
I’m not the Product Hunt target user. I’m not downloading apps every day. I’m not looking for the latest, greatest things. I think there are a few basic problems, and people are trying to solve them. I’m rarely installing apps.

Shyp was the last app I installed that I use and was blown away by. Props to the folks who are involved in that. It’s an amazing experience to have someone come pick up a package in 15 minutes and take it away. I think they’re going to do some interesting things as they scale and push down prices. If they can put the post office out of business, that would be an amazing feat.

It seems like communication apps are designed in extremes —built around anonymity, or built around people’s real personalities. What do you think about that?

There’s this concept of presentation of self. People present themselves differently in different contexts. You’re going to want to be different people online. You’re going to want to interact in different ways with different communities.

I think that’s something Facebook understands really well. Zuck is the man — he gets it. He’s not [thinking there is] one platform to rule them all. He’s trying to figure out how to serve all the needs of people to connect in different ways, at different times, with different kinds of people. For what it’s worth, I’m long on Facebook because I think they actually really get how to build a constellation of different apps that serve these different needs. I wouldn’t be surprised if we see them buy whoever the winner is in anonymous apps, because they see that as a legitimate [communication] use case.

You can say things that are true without worrying too much about offending people. What does SLJ stand for? What are some things you’ve said or want to say?

That’s the thing that keeps it entertaining. Here’s this identity that’s obviously fake — I am not a cartoon black man. You just put these ideas into the world, and people have to take those ideas for what they are. It’s not that there’s a specific agenda there. It’s not like I have this ax I’m trying to grind. If you closely read every tweet, there are some things in there that are inconsistent with one another.

Sometimes it’s just putting an idea in the world, and seeing how people respond to it. That’s just a fascinating experiment — seeing what people say, what they like, what they don’t like. I’ve learned a lot about social products, and virality, and what kinds of messages resonate with people. There’s no specific message — I hope [SLJ] is good for the world, and good for startups. I hope it gets people to think. I try not to be mean, because I don’t want to see bullies in the world.

I keep wanting SLJ to be a revolutionary figure and talk about all the things no one else can talk about — what Silicon Valley does well, or not so well — the product and tech side, but also the culture side.

You want to talk about what’s rotting Silicon Valley? Let’s start with diversity. If you look at the demographics of the country or the world, and you look at the demographics of Silicon Valley, they are very different. So you can basically conclude one of two things: either the people who aren’t whiter and more dudely don’t have as much merit, or we’re doing something wrong and we need to fix it. That’s an issue I care about, and I’m really glad it’s an issue people are talking a lot about right now.

I’m really appreciative of people out there who are doing things [about equality]. People like Ben Horowitz, Dave McClure, Mitch Kapor — Mitch is a badass motherfucker. He’s over there in Oakland doing such great stuff. He’s not out there talking about how great he is, but we should be. If you’ve got a startup and you need some interns, you should go over to Mitch and say, “Hey, bring me some of these kids who are from the streets of Oakland and know how to hustle.” If you want good marketing people — if you want a good ground game — go get some of those kids and put them in your startup.

That’s diversity. What’s next?

What other topics concern you?

The two big issues I really care about are diversity and gender equality. I’m a big fan of what Sheryl Sandberg is doing. I work with a lot of female founders; I really try go out of my way to give female founders time because I think they do have a harder time of it. I see it in the interactions. The other day, someone said, “It’s hard to hire female marketing people because it’s been a dude’s game traditionally, so there are only junior female marketers.” That’s such a bullshit thing to say. If you don’t have them on your team, that’s because you haven’t prioritized it. Go find those great people, because they’re out there. We just need to stop making excuses, and we need to fix these problems on our own teams [first]. That will effect the way other [companies] do business.

Culture is a hard ship to turn. If you get to 20 people, and 18 are white dudes, you’re going to have some problems. That’s cultural debt. You need to be thinking about that early, because the first 10 people you hire, and the way you interact with one another, is going to shape your company as it grows and gets outside of your control. The decisions you make [early] will be coming back at you for the next 10 years.

Editor’s Note: This Q&A text has been edited for brevity and clarity. Check out the podcast to hear the full-length conversation and SLJ’s awesomely disguised voice.