halloween highlights, circa 1996. ever the entrepreneur, i grossed 42 pounds of candy that year

What’s Old is New Again

Editorial influences and a proposed workflow for Startup Portraits.

This is the third of three posts covering my pre-launch thoughts for Startup Portraits, a personal photography project. Part one covers the basic idea; part two covers my motivations.

I’ve spent my share of time in newsrooms, including some I’ve run, and I have strong memories of editorial meetings, going back to college. Done right, these meetings were thought-provoking and informative — for the journalists, that is. The people in our stories? As a point of ethics, we left them in the dark. So I’ll be clear at the outset: Startup Portraits probably isn’t journalism.

I suppose it’s telling that my first instinct is to reference the reporting process, but I’m actually grabbing inspiration from a number of sources. From journalism, I’m taking lessons on the power of editorial vision; from blogging, lessons in engagement and analytics. And documentary photography will inform my creative process. Think The Setup, but photo-driven. Or the Talk page in The New York Times Magazine, but trade out people for companies. The goal? Digestibility for readers, and repeatability for me.

To coin a term, we can call Startup Portraits “collaborative documentary storytelling.” Here’s what I wrote in the first post of this series:

I’ll work with each company to answer two questions. First: How is your product impacting the world? And second: What is your company learning? I’ll say something like: “You’re my guide. Let’s tell the story of why your product looks like it does today.”

Cool in theory, but pulling it off won’t be easy. Below is a draft guide to how I think a startup portrait should be planned, including, yes, a collaborative editorial meeting. This will certainly evolve, but for now, if you’re reading as a founder who’s interested in working with me, this is our starting point.

First, it’s worth remembering why we’re doing this. Roughly speaking, I want to explore an industry I deeply respect (and belong to, for that matter), and meet awesome folks doing things that interest me. You presumably need your story told in images, whether for marketing purposes, a use related to your product, or simply for posterity. Here’s a mock timeline of our relationship:

1. One of us pitches the other (doesn’t matter who first), I research you if I haven’t already, and when we’ve both said yes, we set up a Google Hangout to discuss editorial goals and logistics.
2. In the Hangout will be me, and from your end, a dedicated liaison and least one cofounder (preferably the same person), as well as anyone else who will have a substantial collaborative role.
3. We’ll draft a rough list of scenes and situations that fit the goals of this project. I’ll ask questions like: “Who are your evangelists, and can we hang out with one? Do your users experience ‘a-ha!’ moments? Where and when? Where does your user’s journeys end, and how can that be represented visually?” Depending on your product and research schedule, other situations should be more obvious.
4. We’ll then have a brief discussion about any shots you’re desperate for. I’ll devote up to an hour to anything you’d like. Standard photos like portraits, your office, or you crushing interns at ping-pong should be included here.
5. The Hangout will end with us picking a date, and then you’re responsible for arranging everything we discussed. I’ll also send you a contract at this point, though of course no money is involved.
6. When the day has arrived, I’ll meet a cofounder at his or her home and we’ll be off! I’ll be happy to get passed off to many different team members—that’d be good, actually—and we’ll plow through the day’s agenda.
7. I’ll ask you to write out short answers to a standard set of questions (say, four or five) about your company. Besides my photos, this will be the meat of what I blog. I’m still thinking about these questions.
8. Finally, I’ll draft everything up as a Medium post, share it with you for review, and hit that big ol’ publish button.

That wraps up my initial thoughts for this project. As always, I’m hungry for feedback. As excited as I am about this, I expect there to be important factors I’m glossing over, so I’d love to hear from you. Email is best: jackson.solway at gmail.com. And, of course, if you’re an intrigued founder, get the hell in touch.

Part one: The idea. Part two: Personal motivations.