Get to Know: Jackson Solway, Cofounder

Joined Job Portraits: August 2013 | Based in: Pacifica, CA

What do you do at Job Portraits?

In the startup world, saying you’re the “ideas person” is often code for not being very useful. I hope to God that’s not me — but a big part of my role is figuring what Job Portraits should do next. That involves a lot of my own ideas and a lot of poking and prodding my teammates for theirs, as well as learning from what we’ve seen other founders face at much larger companies. My goal is to identify the next, most valuable thing we can tackle that will support the growth of the business and of team members as individuals.
As far as client-facing work, I wear a couple of hats. Until recently, every invoice, legal document, and conversation with a lawyer went through me, and a lot of them still do. I also handle most of our photography, which lets me exercise some creative muscles. If you pause and imagine what it looks like inside a startup, in some small way I’ve helped define that — I’ve photographed over 50 companies, and they use the images everywhere. I try to get shots that reflect a company’s values. It might be people from two different teams working together, or the whole company eating lunch together, or a group of folks playing basketball. But it’s all real. I’m like the anti-stock photographer.

Why did you start Job Portraits, and what were you doing before?

I worked in journalism after college, and I also started two companies — one of them with Miki. For the nine months before Job Portraits, though, I was figuring out what I wanted to be when I grew up. Sorta kidding, but not really.
I was interested in product management, but I wasn’t getting interviews. I ended up cold-emailing a bunch of founders and offering to blog about their businesses in exchange for face time. I’d spend half a day interviewing people and taking pictures, trying to learn about the culture of the place. I’d edit everything together and hit publish, and then — surprise! — within a few days, the companies were using the posts to help with recruiting. I went back to two companies and asked if they’d pay me $300 to do another post, and they said yes. I was like, “Cool. Let’s call it Job Portraits.”
Miki left her job around that same time, and we decided we wanted to work together again. Founding a company with your spouse isn’t for everyone, but it’s made everything better for us. We’ve learned more about each other, and how to communicate with each other. And we’ve built deep trust because we make all these important decisions together every single day.

Tell us about the culture you want to build at Job Portraits.

I have three basic beliefs about work culture: it drives decision making, everyone participates, and it changes over time. I think all of that is true whether you want it to be or not. I don’t expect culture to be static; I think the challenge is to guide it and nurture it, and the tactics for doing that will depend on the stage and size of your company.
Collaboration is a big part of it, and diversity of thought is a dearly held value of mine. I think the best way to solve a big, hairy problem quickly is to have people from a lot of different backgrounds in the room. You need psychological safety and trust, too. It’s essential that people feel comfortable challenging each other, or at least if they feel uncomfortable, they know it won’t last for long.
One thing I prioritize is figuring out which tasks and decisions can be handled by one person, and which call for collaboration. Without that alignment, everything is mushy. But if everyone on a project understands what they’re empowered to do, we can move fast, especially because I default to individuals having authority. I understand that sometimes I need to deliver a creative vision or kick something off. But in an ideal world, I set expectations with a bunch of supremely talented people, and then things just get done. If they don’t, I know I seeded the conversation poorly, or had the wrong people in the room.

How do you think about leadership?

I’ve got a tortured relationship with leadership. I was in charge of two different organizations in my early 20s, and both times, people started treating me differently as soon as I became the leader. That was a head-scratcher for me, because I’d never treated my bosses like bosses. They were just people. But I rolled with being the boss, and I eventually learned how to push people so they felt both challenged and supported. A ton of stuff got done and everyone felt great about it.

One of those times was as editor of my college newspaper. Before I started, no one made deadline — ever. But every single person I hired, I told them, “You’d better be ready for this. This is a very strict environment, and if you don’t make deadline, everyone’s gonna be in pain.” At some point, that became the truth. I remember thinking, “Holy shit. This whole ‘setting expectations’ thing is the source of so much good, but also has the potential for so much evil.”
More recently, I swung too far in the direction of letting people chart their own course, and I still worry that I can be too friendly, or too indirect. But I think I’ve landed in a pretty happy, healthy middle ground.

What’s surprised you most since you started this company?

I was surprised at how rusty I was as a leader. Miki has leadership skills that are far beyond my own in some ways, and I was like, “Damn, I’ve got to get on my game.” It’s certainly not a competition, but I do feel inspired and pushed by how she navigates relationships and difficult conversations. It’s awesome.

I’m working on my own skills through a combination of coaching, transparency, and feedback. I really want people to tell me how my actions and decisions impact their work and feelings. Our client work is also a source of inspiration. Seeing other founders take risks — that makes it easier for me to do the same. It helps me see my work as a perpetual learning process rather than something I should already be awesome at.

Lightning Round!

What’s your morning routine?

I roll out of bed and either go straight outside for a walk around the neighborhood, or hop on the computer and do something creative. For whatever reason, I get this euphoria when I wake up, almost like a runner’s high. It is far and away the most productive and most fun part of my day.

I have to admit, I also check Bitcoin prices most mornings. I won’t pretend to understand cryptocurrency, but I put in a couple hundred bucks a few years ago. It’s worth a lot more than that now, and I am shamelessly caught up in the mania. It’s like I’m playing scratchers. I have zero expectation that it will be worth a dime a year from now, but I’m having fun while it lasts.

What’s your superpower?

I can take a nap anywhere. Miki has the Instagram posts to prove it; she’ll take a photo of me lying in the most awkward position, mouth agape. I’m not on Instagram, so I’ll see them two years later and be like, “Hey, when did that happen?” Napping is a handy superpower, though, because it lets me capture that post-sleep state of mind again in the middle of the day. Sometimes I’ll take a nap when I’m not remotely tired, just to get a second wind and be super on my shit.

What’s the worst advice you ever followed?

Disney and Hollywood messed me up pretty bad. Movies have to keep people engaged, so they focus on the parts of love that are most dramatic — the high highs and the low lows. Love is magical, but it’s not Disney magic. I think it did me a disservice in setting expectations for what a healthy relationship should look like. Luckily, Miki rescued me from Mickey, if you know what I mean.

Tell us about a book that had a big impact on you.

I found Fear and Loathing in Las Vegas in my parents’ garage when I was 11. As soon as I read the first page, I remember thinking, “Damn, I’m in trouble.” I couldn’t put it down. I’ve been a pseudo-journalist ever since.

If you could interview one person, living or dead, who would it be?

I’d interview my older self — like, I want my 80-year-old self to appear tomorrow. We’ll go get donuts and walk around the block. I don’t want to know everything — no lottery numbers, no loves won or lost. I just want to know what stays the same. I want to know what aspects of my current life and beliefs are worthy of another 48 years. That’s assuming I don’t turn into some asshole, anyway.

What unpopular opinion do you hold?

All of them! But I’ll go with, “I don’t think the personal is political.” Or at least, I don’t think it should be. That concept is in vogue right now, certainly on the far left and far right. There’s a lot of self-righteousness, a lot of offense taken, and I think that puts society in a shitty place. It makes it harder to have conversations about ideas, and being able to debate and refine ideas is really, really important if we want people to get along and work together.

What’s your next adventure?

Parenthood. I know kids poop and pee and cry and you never get any sleep. But I’m hoping I’ll also be reminded of all the things I take for granted, and I’ll get to question big assumptions. It’s gonna be hard as hell, and I’m really looking forward to it.

Video music credit: Music: From Russia With Love — Huma-Huma

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