Meet Christopher Wink: an interview with Technically Media’s Cofounder/CEO
What did you think of Brian James Kirk when you first met him and when were you like "yeah dude I wanna be partners in business with you for the next 9+ years"
I first met @brianjameskirk as undergrads at our college newspaper and I absolutely saw Brian as this stoner designer dude. He saw me as a preppy kiss ass. It took a year for us to come together. We’ve grown and changed together a ton. Here we are now!
What were you like as a teen, were you nice to nerds?
I was surely the nerd to some myself. I think I had become a decent dude by high school. In contrast, I was a bit of a brat in elementary and middle school. I was always an "involved" person but by my teens I was likely even more similar to how I am now: I said a lot of ridiculous things and always had some scheme or project. I think that and playing sports (basketball and soccer) let me dip into several social groups.
When are you running for office and what's your policy platform?
If I'm running for office (which is clearly not in any immediate horizon for me), my platform would be very centrist-y and trying to make the word "compromise" distinct from "compromised." Historically social movements have lasted when they've been about gaining widespread popular opinion. Economic development through entrepreneurship would be a focus.
Who is your favorite person besides Shannon and Brian James Kirk?
My father is deeply influential on me, I’ve traveled on annual road trips with my childhood friend Michael. Considering what you’re asking me, Patrick BIG TIMBS McNeil is my best friend and would likely be the person I have the most intimacy beyond Shannon and Brian James Kirk.
What's one thing you never expected to be hard about starting a company?
I think I remain surprised by how many decisions are neither the RIGHT nor WRONG one but instead are simply choices. Choices that WILL hurt someone and help someone else. I find clean decisions are very rare. Life is messy and you get put in a position of guess work. Growing a company is 1,000 choices that in the moment no one very much agrees on.
What's your spirit animal?
Spirit animal. I'm gonna be real with you, I'm v into the domestic house cat. But I might go with a nurse shark because they look fierce but they actually don't kill, they're just kinda badass. I saw a bunch of them while snorkeling off the coast of Belize last year and was blown away.
What did running with the bulls in Pamplona feel like and was it worth it?
Running with the bulls probably best travel decision of my life. The moments before it started was the most scared I had felt in a "safe" public place.
Gratuitous video of part of it https://www.youtube.com/watch?v=ziZyUa9Dt24
You're tall as hell dude, did you ever consider playing basketball ? I'm thinking you coulda played small forward at a Div 2 school at least bruh.
I played basketball growing up and into high school! Last night I was telling the story that so crystallizes the kinds of relationships I tend to have. When I was a senior, we had an exceptional point guard (1k+ career points) and so my entire job as the other guard was to just give him the ball and then go play defense. Late that season against our arch rivals, the team came out and started immediately double teaming him. I was open a lot and got hot and scored 20 points in the first half (mind you, I’m maybe averaging 7 points per game). At halftime my closest high school friend says to me "I guarantee you don't score another point in this game." .......He was correct
Did you win a high school superlative? If so, did you ask people to vote for you?
Yes! I was "Class Clown" and "Most Involved. " I was runner up for "Most Likely to Succeed" and still plan on surpassing that friend to own it. Admittedly, I went to a pretty small school :)
What's your favorite Technical.ly memory to date
Favorite Technical.ly memory to date. Real talk, I always have a favorite moment that happened in the last few weeks because I really seriously no BS love the evolution and growth and seeing us get better together. So always a v recent thing is my favorite memory. But because I don't think that's really what you want meant to say, I'll instead say the kickoff of Philly Tech Week 2013 when we did our first outdoor kickoff and after we almost finished the later-Guinness Book of World Records confirmed world's largest video game by playing Pong on the Cira Center, a torrential storm crashed over us. This photo is @brianjameskirk Corinne Warnshuis, Juliana Reyes, Andrew Zaleski and I holding tarps over arcade games we had rented and were afraid we’re gonna get destroyed
Can we get an office dog? just met a really cute Australian shepherd puppy
Communities are platforms on which collective action can take place. You are empowered to gain consensus among the team and keep, maintain and care for a dog, yes.
What advice do you give 21 year old CGW?
Advice I'd give 21-year-old CGW? (1) Do not self-deprecate needlessly. (2) Start a focus on email subscribers sooner with Technical.ly (3) Do more family stuff
What's your favorite story that's ever run in any of our markets/brands?
Favorite story that has run in our markets, I'm gonna go with two because there have been thousands. Off-hand, the Tyler Woods Startup Founder on Welfare story stuck with me and I think about it a lot. Yes, it isss probably something that would run elsewhere but it felt v much OF us, like a relationship built because of deep ties that was trying to be REAL about something. PRODUCTIVE https://technical.ly/brooklyn/2016/01/12/inside-welfare-office-anonymous-startup-founder/
And I'd sadly point to a byline of mine but more because of what it was for the org as a whole. This piece was a big pivot point for us
https://technical.ly/philly/2011/04/25/how-open-data-philly-got-done/
When we were INVOLVED in launching OpenDataPhilly and I can't underscore how WEIRD that was. We had a lot of internal conversations, including @brianjameskirk and I about whether it was OK that we had reported on WHAT the city needed and could we be INVOLVED In it
I think about the full disclosure at the top of that story a lot. It threw us into a lot of open data and civic conversations, but it also set up HOW we approached being a PART Of our community. I think not long after we changed the tagline to "Better Cities through Technology"
Fave place you've traveled
I lived in Tokyo for a bit less than a year and so fitting in my interest in time to get to know a place, that stands out to me a bunch. It is this international city so it’s so easy to go and it not be special but living in a neighborhood and having neighbors and a grocery shop was really profound. I did so much writing and reading it was profound. It was also where I first started as a bicycle commuter.
What's the most embarrassing professional moment you've ever had and, I guess, what did you learn from it?
Early on, I remember not knowing what SaaS was during an interview and I fumbled my faking it and it resulted in several weeks of me having nightmares of being on CNBC for an interview and embarrassing us all. So I got obsessed with returning to a basic business and tech background, preparing for disruptive questions
If you could pick, what would be your superpower?
Invisibility always stands out to me as lowkey powerful. But maybe SUPER LINGUAL, like, where I could speak any and all languages
What was the most hilarious/ridiculous thing that happened to you in a professional moment?
My oft-cited memory of me finding out I had a giant hole in the crotch of my only pair of thrift store khakis after I had sat down w/ my first big client meeting (that is the rock bottom moment that turned around my relationship with clothes)
Is the future of journalism bright or dreary?
Journalism bright or dreary? Yah, for me, journalism is a THING you do, like producing software open source, so I think its future is super bright, so long as there are practitioners like us passionate about its utility. I was able to pull five-county criminal records last night in an hour online for this story I'm reporting. I am better sourced because of web tools, so journalism is easier to do. Building it into business models (like we're doing,) that is really hard and it's the most important thing I think I'm working on but the strategy of making public information that is true accurate and helps other people is v bright
Ooff, rn I'm inbox 64, with 25 unread!!! It has been a busy yesterday and this morning. I'll leave today with that at 20~ with all read and w/ necessary actions cleaned up in Asana.
What's the next Chris Wink side project after the retirement of Story Shuffle?
I came to reporting from the writing side first. There is nothing I love more in the world than writing. In the last 18-months I've been picking back up some creative writing and so I'll be putting some real time into getting a few modest pieces published on that form. I def self-identify still as a journalist but really, more than reporting, it's the writing I love. I want to move a bigger effort there (Story Shuffle was always part of that longer term strategy too )
You're good at talking about yourself and exceptionally self-aware. Advice for knowing when to STFU and when to dig deeper?
I think journalism training is soooooo good for self-discovery. I think it really starts with accepting yourself. You'll get teased for (as I do) for being self-referential or self-involved but I think it's really important to be able to say I REALLY LIKE THESE THINGS ABOUT ME but also be able to say THESE ARE THINGS I REALLY WISH I WAS BETTER AT. And then attacking both of those with questions. You can internally interview yourself like you would. I want to be able to understand why I am good at some stuff and why I'm crummy at other stuff. Self-improvement is v cool,but it starts w/ some self-love.
Do you like being surprised?
Nah, I don't like being surprised. It's probably part of the whole reporting love. I want to be the one who knows stuff, not surprised.
If you were not the CEO of Technically Media, what would you be doing?
If not in my job now? Realistically, probably a reporter somewhere, likely in/around politics/government. Less likely but relevant, maybe ended up cofounding a dif kind of company or in some other purely writing role.
When you come back into the office can you show us your signature dance move?
I assume you mean my interpretive dance performance "Swallowed frog." No! I'm all for embarrassing shit WITHOUT CAMERAS. I say let people live and be silly and keep the cameras for things strangers can see. Intimacy doesn't do well w/ recorded archives
Take a half-hour walk every single night together.
When did you get your first phone? What type of phone was it? What was your background picture? And, did you have a ringback tone (if so, what song).
I got my first phone when I was a sophomore in high school (!) when I got my learner's permit for driving. I remember using a pay phone to get picked up as an 8th grader. I'm pretty sure that phone literally did not support background images or ringtones.
Been wanting to visit Tokyo for years. Any tips for traveling there?
Tokyo (Edo) was constructed over time as a medieval place to protect from attack, so the streets intentionally do not make sense. It's the opposite of Center City. (London got confusing just over time, Tokyo is intentionally built as a confusing fucking place to navigate. ....So def have .GPS access...or don't and just leave time for getting lost. Eat at every ramen shop under a train stop. The tiniest old men with craggy faces and expressionless smiles will serve you at the counter and then bow, and you will bow in return. It will be nice. Fun Tokyo story we've already talked about, I was part of a lil NBCU pilot online reality show jawn and I got lost in all the episodes
Who's a person outside of Technical.ly (or Shannon) you would turn to for management advice?
I talk to my father weekly on the phone and I find his perspective interesting. He works at a small concrete, stone and tile manufacturing company and I find his perspective on what is normal in the workplace. I also have always been moved by his pragmatism and quiet generosity.
It is v internal facing. I am v demanding of myself to be better than I was before. I don't like things that I don't understand how to get better at. So: to be a better version of myself than I was. Shannon and I talk about that: that we're supposed to keep becoming better versions of ourselves for the other
Who are the top 3 journos out there you would pay / do pay to read?
So the Economist famously does not have bylines so I don't think I could name one but I am a very happy proud longtime print subscriber so surely someone there. I truly love the ways we approach storytelling here, so those bylines from Julie Zeglen Stephen b Tyler Woods Tony Abraham Juliana Holly Quinn Zack Seward etc, do mean alot to me, I would consume them. ...And, yeah, I'm a George Saunders fanboy and so I like when he's been pulled into doing fun profiles
Name three Philly tech scenesters you're truly fond of / name one that you... could do without?
Robert J. Moore and Jon Gosier on the founder front, I'm v impressed w/ them and always feel smarter when I talk to them. (Garrett Melby is that too). I make no secret that I have a real soft spot for Archna, whom I long found one of the most under-celebrated for her relative impact. And on the v young front: Dawn McDougall. I think she took a v mature pathway to not wanting a full-time director role for Code for Philly because she wanted to gain some experience at an org. She showed some power. For someone to get rid of? I don't think I can put that in writing.
What's the main reason Yuriy Poritko fascinates you?
Two things on the Yuriy front (for others, he's a Philly organizer who has been around forever and I'm writing a lil something on him that's gonna run next week). I try to write something for one of our markets every six weekssss~ and so I always wanted to do something on him just because he is eccentric and colorful. So it started just that he is interesting. But then other pieces started coming together, and I started putting more time into it once I wrote my nut graf. I found that I could connect him to a bigger/broader lesson that I think other communities face too. So (a) he's interesting and (b) he does represent something. He has caused some real pain and damage, but he has done genuine good. I don't find EVIL or GOOD characters interesting. I think people who are complex and complicated are far more challenging to write. I am not aiming to judge the man in this piece, I’m aiming to better understand why he is who he is. I think that’s the kind of community reporting and business journalism I love most.
What do you do when you’re bored?
I’d say I can’t remember the last time I was bored but I know what ya mean. I watch a ton of science and history Youtube videos when I’m eating at home. I also am basically always tryyyyying to write, whether that be my iPhone notes app open or scribbling in a pad. ..Also Twitter is an incredible place to learn if you curate your followers thusly :slightly_smiling_face:
What are your thoughts on early let outs on Fridays before national holidays?
:eye-roll: Seriously I always find those questions weird, I am not tracking anyone's hours, never have been! Get your shit done. Work hard! Do your time most weeks and take time for you other times. It's so simple, if you're doing good work and giving :100: and build a relationship of trust with your team, then choose when it's right for you. I guess I can do a better job of communicating that but there is no magic time that you can work toward and I am HAPPY. If you're supporting your team and doing great work and you are EXCITED About being here, I don’t think anyone says anything. So, idk, go home!
How about some book recommends for another avid reader?
I am not a fast reader, my wife has me beat. I'm trying to simply get back to a book a month (have a resolution of reading a writer of color for the first time each month this year) and not nailing that but I loved Zadie Smith's throwback White Teeth.
Who here is most likely in 10 yrs to write the book on Technically Media?
Probably you [Cary Betagole, Senior Product Manager). You have a low key historian's view and a smart distance
jbbartram-illu
vaporwave
stormborns
theartofmadeline
ellievsbear