I’m Dan Oshinsky, and I run Inbox Collective, an email consultancy. I'm here to share what I've learned about doing great work and building amazing teams.
I was talking with my dad this week. I’ve got Inbox Collective — four years in and going strong — and my sister has a little side business of her own that she’s thinking about expanding.
My dad wanted to know one thing: “This is my fault, isn’t it?”
In the best way, dad, it is.
See, some three decades ago, my dad left the corporate law world to go out on his own. He built a great solo law practice for himself. Was it as lucrative as working at a big law firm? No, but he gave my siblings and I an amazing life. And in the past decade, long before the pandemic, operating solo allowed him to work remotely — working some days, volunteering some days, and taking some days off.
Having a dad like that as a role model made launching Inbox Collective a whole lot easier. I’d already seen that it was possible to go solo and make it work — I’d been watching my dad do that for years.
And I’ve been incredibly lucky to have his support over the years. Launching a solo thing — especially a business like mine — requires a lot of contracts. I’ve been lucky to have a lawyer happy to work pro bono to support my business.
Not everyone gets so lucky to have a fine example, pro bono lawyer, and enthusiastic cheerleader in their corner.
So this is the story about how back in 2004, something happened on Martin Luther King Day that changed my life.
Actually, it wasn’t exactly MLK Day. It was the Friday before. Every year, my synagogue in D.C. holds a big interfaith service. Religious leaders from across the city come, and choirs sing, and there’s always an amazing speaker, someone from the community who reaches back and speaks about Dr. King.
In 2004, the speaker was Herman Boone. You remember him as the coach of T.C. Williams High School’s football team, the team immortalized in the movie “Remember The Titans.” Denzel Washington played Boone.
I was writing for my high school newspaper at the time, and my parents got it into their heads that I should go to the interfaith service and approach Boone and ask for an interview. People who know me now don’t believe me when I say this, but it’s true: Back then, I was almost cripplingly shy around strangers. Calling up a source for a phone interview was an ordeal. I remember having to give myself a pep talk before dialing even a single number.
So approaching a guy who just had a fairly epic Disney movie made about his life and asking for an interview wasn’t exactly what I wanted to do on a Friday night.
But my parents didn’t budge on this one, so I went. There was a dinner before the service, and my mother prodded me along — think momma deer nudging her child forward — and over to Boone. I introduced myself, told him what high school I went to, and asked if he might have 20 minutes to talk to me over the phone.
Boone waited for me to finish, and then he asked a question I didn’t expect: What was the name of your high school, again?
Walt Whitman, I said.
In Bethesda?
Yes, I said.
I think we played you guys back in 1971.
1971 — As in, the year the Titans won the title.
Whoa.
I got his number and we set up a time. A few other Titans were there that night — I got their numbers, too. And when I went home, I dug up the name of the Whitman coach from 1971. His name’s Bob Milloy, and he’s still coaching in Maryland, at Good Counsel. He’s the winningest active coach in the state. Whitman was his first head coaching job.
I sent him an email and asked him if he remembered anything about playing T.C. Williams.
He shot me back an email. I wish I’d saved it, but I didn’t. I remember the opening line, though. It said, simply: “Yeah, we played ’em.”
And so that’s how that story was born. I interviewed Milloy, and then talked with some of the Titans, and then Boone. The Boone interview I remember best of all. He told me stories about hurt and pain and hate that I can’t even imagine.
I wrote the story, and it turned out well. My journalism teacher suggested I send it in for an award. The Kansas City Star had this award for high school journalists, the Hemingway Award. I’d submitted two stories the year before and had been named a finalist for sports writing. I submitted again.
I won.
And so I went out to Kansas City to receive the award. There were a bunch of Mizzou grads on the Star’s sports staff. They all told me the same thing: Go to Missouri for journalism. They insisted and insisted — it could only be Missouri, they said.
So I went.
Things fall into place like that, sometimes. Looking back, it’s easy to see the path now. Mizzou opened up worlds for me, friendships for me. The fellowship I’m on now doesn’t happen if I had gone elsewhere for college, I don’t think. So much of my adult life has been shaped by this university.
And yet — I don’t get here without those conversations at the Star. And I don’t get those without winning the award. And I don’t get that if I don’t write the story.
And I don’t get the story if I don’t show up, that MLK weekend in 2004, and ask a coach if he’d like to talk, and if he doesn’t remember that 32 years earlier, his school and my school decided to play a football game.
I don’t know if it’s coincidence, or luck, or fate. But it is one hell of a story, and I’m honored to have told it.
So this is the story of how I called three airline customer care numbers in one night — and then Zappos.
And then I understood.
Now, I don’t recommend calling multiple airline customer care hotlines within the span of an hour. They’ll make you mad. At the first airline, it took me 15 minutes to get on the line with someone — and that’s only after pressing every button on my phone five times just to figure out the secret code to get to an actual human. At the second, the customer care rep actually snarled at me over the phone. By the third call, I was numb.
Airlines have gotten pretty good at replicating the in-flight experience over the phone, it seems.
Last month, I decided to buy two pairs of boots on their site. I found the ones I wanted. Clicked buy. Got the confirmation email that they’d been sent. And for three days, I checked each morning to see when my shoes would be arriving.
I was weirdly excited for these shoes. I’ve never owned a pair of decent boots before. The thought of looking all professional was… kinda cool, actually.
Anyway, it’s Thursday, and I check the UPS site. The package had been delivered, it said. I walked home, walked to my mailbox… and nothing.
I went to my apartment. Nothing sitting on my door.
I took a loop around the apartment building. Then outside.
Nothing.
I call the landlord. Anyplace else I should be checking?
Nothing.
So I call Zappos. And they tell me: Yeah, it’s not all that uncommon that around Christmas that people steal packages. But that’s alright. UPS insures everything we send. When we get your shoes back in stock, we’ll just send you a new pair.
Sweet!
Two weeks pass, and I check the Zappos website. One pair of my shoes is in stock. I give Zappos a call.
Just as before, a human picks up quickly. She’s cheery, pleasant. Even makes small talk about state abbreviations.[1. “MO! I’d never heard someone pronounce your state’s abbreviation as a word before!”] I tell her about my issue. She looks through it, tells me not to worry about the stolen shoes. Tells me she’s happy to refund the money for the pair of boots that isn’t in stock, and she’ll send me the other boots right away.
And, just for being patient with us: We’re upgrading you to VIP status, so you can get way faster shipping.
Sweet!
I get the confirmation email from Zappos this morning. The boots will be here this very afternoon.
Really sweet!
And this time — I’m not taking any chances. I’m having them shipped to work.
This isn’t a new experience for me. I’m not sure I believe that certain generations are defined by certain songwriters — Do my parents belong to Dylan? To John and Paul and George and Ringo? To Jimi? To Janis? To the Stones? — but I know that certain moments demand a voice. There are weeks when the right song hits me at the right time. I’ve lost months to Joe Purdy’s woes, to Steve Poltz’s quirks, to James McMurtry’s tales of Texas.
A lesser songwriter would lose his audience with stories like those. Not Snider’s crowds. They come for the stories.
That’s why I came.
But lately, I’ve been listening to Snider’s records. And I’m finding that Snider’s got the voice that speaks to what I’m going through now with Stry.
It’s been 15 months since I left my job to start Stry. Things keep changing. I keep learning.
But what has stayed constant is this: I am always on the verge of being completely, totally screwed. Stry is not making money. It does not have any other employees. The only thing keeping the Great and Good and Honorable Dream That Is Stry alive is me.
Mine is not the story of business success — not yet. So this moment demands a songwriter who’s been out there, trying, struggling, failing, laughing, scratching at the edges of success. Someone who’s taken risks. Someone who’s been both the next big thing and the has-been. Someone who’s been out there long enough to have perspective on how life goes, especially when it goes places you never wanted it to go.
Snider’s the songwriter who can explain all those stages: The empowerment, the discovery, the struggle, the success — and the failure. Oh, the failure.
Start here. I am sitting in my cubicle in San Antonio, thinking about something more, thinking about changing the world — couldn’t be that hard, right? — and there’s Todd Snider, singing:
You can’t talk to me like that boss I don’t care who you are If you don’t want to have to hang your own dry wall Don’t push me too far
Suddenly, I’ve left my job. I’m in an apartment in Biloxi, Miss., drafting up a mission statement for Stry. And I’m thinking:
Life ain’t easy getting through Everybody’s gonna make things tough on you But I can tell you right now If you dig what you do They will never get you down
And that’s keeping me going for a while.
And then Stry’s getting off the ground. I’m thinking a bit too ambitious. I’m thinking that selling this thing is going to be easier than I’d previously thought. I’m getting a bit greedy. And Snider’s singing:
Everybody wants the most they can possibly get For the least they could possibly do
I’m back in D.C. Selling it isn’t easy at all. I’m clueless. I’m learning. I’m trying. I’m failing. I’m floundering. I’m trying to find myself. And Snider’s singing:
Sometimes you rise above it Sometimes you sink below Somewhere in between believing in heaven And facing the devil you know
I start to find a way forward. I settle down a little bit. Maybe I start to settle for something a bit less than changing the world. I start to find myself. I start to wonder whether I’m ever going to get moving again. I start to doubt myself. And Snider sings:
A little out of place A little out of tune Sorta lost in space Racing the moon Climbing the walls Of this hurricane Still overall I can’t complain
Then the complication comes back around. More failing. More setbacks. More struggling. And Snider’s singing:
Some of this trouble just finds me No matter where I turn How do you know when it’s too late to learn?
And now it’s the present day. I’m thinking about the fact that a year ago today — Oct. 3, 2010 — at about this very hour, I was pulling into my driveway in D.C., my whole year ahead of me. No plan, no idea of the road before me. Just a dream and a website. And Snider’s singing:
Lookin’ back on where I was One year ago today Laughing at the shape I’m in now
And Mr. Snider: I know you’re right. I am looking back, and I cannot help but laugh. Oh, how little I knew then.
How little I know now.
I know haven’t gotten that far in the entrepreneurial process. No, I don’t know what lies ahead.
But I suspect that when I get there, I’ll find there’s a Todd Snider song that explains it perfectly.
Today is Rosh Hashanah, and I am in Columbia, Mo. The last time I was in Columbia for Rosh Hashanah, Barack Obama was just a Senator from Illinois, my Missouri Tigers were about to head to Lincoln, Neb., to play a conference game, and I was still a month away from signing up for something called Twitter. Now I’m back at Missouri as an RJI Fellow, and I dress decently and show up to work at 8 or 9 and leave at 5 or 6 or 7, and I have a corner office, and a staff that is on call to help me, and when I leave a voicemail for someone, that someone calls me back.
For the longest time, I’ve joked to my parents about being “a professional,” but for the first time in my adult life, I actually feel like one.
There is still much work to do, but it is hard not to take this moment to think back on all that has already happened this year. I am most grateful for the journey so far, and I look with wonder towards the journey that lies ahead.
There continue to be an incredible number of people who believe in me and believe in what I am doing, and it never ceases to amaze me how much that knowledge helps me through each day.
Biloxi is not a town of comfort. It has its simple pleasures — the Waffle House, the Whataburger, the Five Guys — but when it comes to some brand names, head elsewhere. The nearest Bank of America is in New Orleans. So is the nearest Kinkos. When Target opened here, they held a celebration just a notch below Mardi Gras.
But what they lack in brand names, they make up for in service. I stopped by the local print shop today to ask about printing a few copies of this magazine I’ve been working up. I hadn’t been in there since early July, when they’d printed out my new business cards.
So I went in, reintroduced myself — hi, I’m a reporter, in town for a few months, yada yada — and asked if they could do this print job. They couldn’t, but they did suggest a competitor who could.
And as I was walking out, the owner of the store called out, “Good seeing you again, Dan.” The door closed behind me, and I swiveled around and went back inside. “Wait,” I said, stopping the owner before she headed back to her office. “How did you remember my name?”
She looked right back at me. “That’s just what we do,” she said.
So here’s to PDQ Printers in St. Martin, Miss. If you’re in town, stop by and let them know Dan sent you. They’ll know who you’re talking about.
