Dan Oshinsky | danoshinsky.com

10/03/201104/26/2021

Todd Snider, The Struggling Entrepreneur’s Kind of Songwriter.

I cannot get Todd Snider out my head.

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.

Right now, I cannot get Todd Snider out my head.

I fell in love with Snider for his stories. I’ve seen him live, twice. He gets up on stage, sings a song or two, and then he starts in with these stories. They’re all just a YouTube search away. Here’s one about meeting Slash. Here’s one about hallucinogenic mushrooms and high school football. Here’s one about a tour manager named Spike.

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.

I hope there is.

09/28/201109/28/2011

Today, On This Rosh Hashanah, In What Is Apparently The Year 5772, I Would Like to Give Thanks.

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.

Onward I go, for them.

09/21/201109/28/2011

#BergChat: The Pivot!

Four weeks ago today, I went in front of a group of students here at the University of Missouri and told them I wanted to buy them a beer and talk about journalism. And then I went in front of another class. And another. And another.

And told them, a few hundred in all: I wanted to buy them beer and talk about journalism.

The first thing that happened was, a whole bunch of students tweeted at me to tell me how excited they were about the idea.

The second thing that happened was, nobody came to drink with me.

Well, that’s not entirely true. I’ve offered three so-called #BergChat sessions to students so far on Twitter. One student has taken me up on the offer.

So it’s time, I think, for a pivot.

What’s a pivot, you ask? Take it from Eric Ries, author of the soon-to-be-bestelling book, “The Lean Startup.” Says Ries, a pivot is:

“The idea that successful startups change directions but stay grounded in what they’ve learned. They keep one foot in the past and place one foot in a new possible future. “

And, okay, the #BergChat isn’t a startup; it’s just office hours at a bar. Still, the spirit of the pivot works here.

Now, the way I’ve been organizing these #BergChats is by sending out a tweet or three to my followers — among them, a multitude of j-schoolers. I’ve named the day/time for that week’s chat. And I’ve asked students to tweet back at me if they’d like to join me for a drink and conversation.

Except that I’ve forgotten a simple rule: College kids don’t operate on the same time schedule that I do. And that means I’m pitching this to an audience that isn’t actually listening at the moment I’m talking.

Hence the need for a pivot.

So here’s the new plan: The #BergChat is always open and available to you, the students. All you have to do is tweet at me something like:

Hey, @danoshinsky, got time for a #BergChat this week?

And assuming I’m in town, I’ll say yes, and we’ll set a time.

To recap: You tweet at me. We agree upon a time. And then said Beer/Shirley Temple is purchased, and we talk about whatever you want to talk about.

That’s my pivot, and I’m sticking to it.

At least for this week.

09/13/201109/13/2011

Why I’m Doing What I’m Doing.

This was originally published over at the RJI blog. But I really liked what I’d written. So I’m republishing it here:

❡❡❡

This is not a motivational blog post. I am not writing this to inspire you. I do not want you to read this and quit your job.

Is that clear?

Are you sure?

Positive?

Because I go to Mach 1 pretty quickly on these things. I get wound up and start running like Lombardi before the Ice Bowl, like a guy who’s got an Espresso drip running in one arm and the soundtrack to ‘The Natural’ blasting in the earbuds. I get wound up, and sometimes, the fortune cookie quotes start leaking out.

It’s all this one girl’s fault. I was having a beer with an MU student on Wednesday. J-school senior here on campus. Ambitious, talented, overworked. She wanted to know about me and my startup. And like any student worth her journalism degree, she had a good question for me:

Why are you doing what you’re doing?

And I didn’t answer it well enough. Lately, all the questions have been forward leaning: What are you doing now? What are you doing next?

But it’s been a while since someone asked me, straight up: Why are you doing what you’re doing?

I didn’t give her the full answer yesterday. So right now, I’d like to tell her, for starters:

I’m doing this because I can. Because there’s opportunity for something like Stry. Because it’s risky. Because I want to learn. Because I don’t have 2.5 kids and a wife and a job and a mortgage. Because I had the money to get it started, and maybe I’ll find the money to keep it going. Because I hated life in a cubicle. Because I’m too naive to know that failure is all but certain for a startup like this. Because I made it this far, and yeah, Red, maybe I can go a little farther. Because I think the phrase “You can be whatever you want to be” needs another case study. Because I want to do the work. Because I like doing the work. Because I like being busy, and not TPS Report busy or Conference Call With the Head of Whatchamacallit busy. Because this is the time I have, and this is what I have to work with, and because I’ve got people behind me who seem to think I can pull this off, and because so do I, and mostly:

Because I can.

There are not a lot of things I believe in completely — I’m not Crash Davis, alright? — but I believe this: In this life, you find things you love and people you love, and make room for both.

Right now, with Stry, I’ve got something I love. I wake up in the morning excited to get up. I know that sounds like some “Jerry Maguire” BS, but it’s true. I love coming to work. This company sinks or swims based on what I do. It’s on me. This thing goes as far as I can take it.

That’s terrifying and empowering and thrilling, and it’s my day-to-day existence. I love that.

And, yeah, the fortune cookie quotes start leaking out sometimes. But I don’t mind that. I had a yoga teacher in San Antonio who told me once, “Trying is doing.”

So why am I doing what I’m doing?

Maybe it’s because I just had to try.

09/10/201110/02/2011

Why I Look Happily Towards The Future of Missouri Football, and What Exactly I Mean By That.

There is a very strange realization I came to tonight:

Fans of my alma mater believe that who we were define who we are.

And I do not.

I was with this girl tonight. She is Missouri-born and a Tiger fan through and through. She loves this team. She actually understands football.

And tonight, when the Mizzou-Arizona State game went to overtime, she immediately said: “We’re going to choke.”

I asked her why, and she said, “Because Mizzou always does.”

And that’s thinking I used to be able to get behind. But lately, something’s changed.

See, when I showed up at this school, Mizzou wasn’t very good at sports. We lost. Always. And usually in rip-your-heart-out fashion.

But since I’ve been here: We’ve won far more than we’ve lost. We’ve beaten the #1 team in the country. Been ranked #1. Been to two Big 12 title games. Won a New Year’s Day bowl.

Longtime Mizzou fans forget this, though. Because in their minds, we’ve always been bad, and we always will be. Even when we’re winning. Even when we’re beating the #1 team in the country.

For them, past is present.

I don’t think like that anymore. I’ve rooted for a lot of bad teams. I’ve seen a Maryland football team get dominated by Ohio. Not Ohio State. OHIO University. I’ve seen teams like American and William & Mary beat my beloved Terps basketball team. I’ve seen the Redskins falter and falter. I’ve seen my Caps fall again and again.

My hometown of Washington, D.C., is closing in on Cleveland as America’s worst sports town. This is not a good thing.

But what I am certain of is this: It is the hard times that make the big wins that much sweeter. As a fan, we need losses like tonight’s. We need to be demolished sometimes.

Because one of these days, a win will come along that reminds us of why we watch in the first place. And it will be all the sweeter because of it.

I believe in the future of Missouri football. I believe there will be heartbreak, and I believe there will be greatness.

And I am damn sure that I will be out at a bar rooting hard for those Tigers every Saturday. I’ll be watching because I believe: Good things come this way.

I hope next Saturday brings better things for my Tigers. I really do.

08/29/201111/01/2012

re: The Catskills. (Or: What I Mean When I Talk About Undercovered Issues in Undercovered Areas.)

The catchphrase at Stry last year was simple: Stry covers undercovered issues in undercovered areas. And any time I mentioned that line, I brought up another.

It’s from a conversation I had with a local when I was down in Biloxi last year, covering the aftermath of Katrina. We were talking about local issues, and she said:

“It’s five years after Katrina, Dan. We’ve still got problems. Why isn’t anyone talking to us about what we’re going through?”

Then came the pause, of course. There is always a pause.

“Is it because we’re from the South?”

And I told her: No. This is the kind of story that gets ignored everywhere. If it happened in Maine or Montana, it’d get forgotten, too, just like Katrina.

I bring that up because just now, I went walking through the lobby here at the Missouri School of Journalism. CNN was on one of the TVs. The governor of the state of Vermont was speaking. And the caption at the bottom of the screen read: “Vermont sees worst flooding since 1927.”

Now, I’d read about the flooding the day before. A lone paper up in the Catskills was trying to cover it. The big papers were completely silent. CNN, to their great credit, did get a reporter up on the scene.

But now it’s 24+ hours since the flooding began — and we’re talking about massive, historic flooding happening just hours from the biggest media market in the galaxy — and the coverage is just beginning to come in.

When I’m talking about undercovered issues in undercovered areas, the Catskills don’t always come to mind. But they’re exactly the kind of place I’m thinking of.

They’re exactly the kind of place I want Stry to cover.

photo at top of flooding in Proctorsville, Vt., via Flickr

[ois skin=”Tools for Reporters”]

08/21/201108/26/2011

Why I’m Starting The #BergChat

Dear University of Missouri J-Schooler,

I remember when I was but a wee undergrad. The year was 2009. A young man named Barack Obama had taken stewardship of our country. The economy was in the crapper. I drove around in a Chevy TrailBlazer with vanity plates.

Much has changed since then. (The Blazer no longer has vanity plates.) But one thing hasn’t:

At our alma mater, the University of Missouri, there exist two distinct sectors of our esteemed School of Journalism: the school itself, and the Reynolds Journalism Institute.[1. I should note here: Counsel has advised me to cease and desist referring to them as my personal Daddy Warbucks.] The J-school is doing some awesome stuff. So is RJI.

Problem is, we’re not always doing great stuff together.

Even though these clusters exist within the same damn building, there’s still a gap between the two. Young J-schoolers dare not venture into RJI. Us RJIers would rather not wander off into the J-school.[2. Except on occasions when there’s free food over in Walter Williams.]

Here’s the point: there’s some pretty incredible Journalism Stuff™[3. Trademark of Oshinsky, Inc., 2011.] going on in Columbia, MO, and there need not be a gap between RJI and the J-school.

So I’m launching a new thing this year: The #BergChat. It’s a weekly session in which I’ll invite anyone from the J-school community to sit down with me for 30 minutes to talk about… well, whatever you want. An idea you’ve got. A question you’ve been afraid to ask. A resume you’d like an extra pair of eyes on.

And while we’re chatting, I’ll buy you a beer.[4. For free. Free, as in: no purchase necessary. Cash value of said beer must be less than or equal to $5. The #BergChat will end immediately if the #BergChat-ee attempts to buy a Natural Light with his/her free beer. These are my terms.]

Now, the fine print:

1. Every #BergChat must take place at the World Famous Heidelberg Restaurant. It’s tricky to find, so here are the Google Maps directions from the J-school for those who’ve never been:

View Larger Map

2. The #BergChat will last 30 minutes.

3. During said #BergChat, I will buy you a beer, or, if you’re not inclined/able, a drink of your choice.

4. To schedule a #BergChat, follow me on Twitter at @danoshinsky. Each week, I’ll be tweeting out times when I’ll be holding a #BergChat. I’ll open up a handful of half-hour slots. The first (pre-specified number) of folks to respond will be given a timeslot. All you have to do is show up and chat.

5. Each J-schooler gets exactly one #BergChat with me. After that, you’ll just have to stop by my office if you’d like to continue the conversation. Or agree to buy me lunch.[5. Hint: I’m a Noodles and Co. fan.]

6. The #BergChat can just be one-on-one, or it can be a group of students chatting. But I won’t take on a group that doesn’t fit in a Heidelberg booth. So essentially, it’s got to be a group of three or less.

Point is: I’m reaching out to you, the J-school population. It’s up to you to make the next step and get involved with what we’re doing at RJI.

See you at the Berg.

-Dan

08/15/2011

The $1,000 Father-Son Belly Challenge.

This is the kind of thing that I shouldn’t go doing. It’s not nice of me to take an old man’s money.

And yet, that’s just what I intend to do.

The old man in question just happens to be my old man, Bill Oshinsky (he’s the little fella you see in the photo below). And he’s got it fixed into that bald skull of his that he can get into better shape than me.

So we’ve made this bet: We’re going to spend a year getting into shape. And on Aug. 1, 2012, we’ll rendezvous to decide who’s got the better belly. Winner gets $1,000. Loser pays.

I’m not going to waste valuable kilowhatevers here on danoshinsky.com with this sort of nonsense, so we’ve set up one of them Tumblrs for you to follow along. Check out bellychallenge.com for more.

08/08/201108/08/2011

A Question From Me, The Professional Question Asker.

I went to see NBC News’ David Gregory speak tonight in a little auditorium on Nantucket Island. He spoke for an hour, mostly about the failures of our political system and our economy and our media, and then he closed by reminding everyone that we were on a little island 30 miles off the coast of Cape Cod, and that everything probably isn’t as bad as it seems.

When that was over, Gregory opened up the floor to questions.

This is the part of the lecture I hate.

Not the idea of Q&A. That I love. We need more Q&A in our lives, and not just at big fancy lectures involving salt-and-pepper-haired reporters in nice blazers. We need lots of thoughtful questions and lots of thoughtful answers in our day-to-day lives. And we need everyone to be asking and thinking and listening in order to be part of this nice little experiment in domestic living that we’ve got going on here in America.

Participation is a very, very good thing, and I encourage it highly.

What I dislike is that I ever since I got my degree from the University of Missouri’s School of Journalism, something’s changed for me. I’ll be at a lecture like I was tonight. I’ll be there with someone else. Let’s call this man, for the sake of accuracy, my father. The moderator will open up the floor to questions. And I will sit back in my chair and listen to questions being asked.

Dad does not like this.

See, my father does not see me as a reporter. Or a journalist. Or a writer. He sees me as a Professional Question Asker. That’s what he believes I earned a degree in out in ol’ Columbia, Mo. And when an opportunity to use my Professional Question Asking skills passes without me asking a question… well, he sees it as an invalidation of my college degree.

And I find this funny. Because I am most definitely not a Professional Question Asker. If there’s anything my Mizzou degree certifies, it’s that I’m a Professional Listener. My job is, if at all possible, to shut up and listen. And then report what I’ve learned. That’s why I’m usually in the back of the room scribbling notes on the lecture program.

At these Q&As, I do this quite well.

Dad does not like this.

Sorry, pops.

But here’s what I’m thinking: Pilots don’t get asked to fly planes on their day off. Bobby Flay doesn’t get thrown behind the grill every time he goes out to eat. Librarians don’t just show up at random libraries and start implementing the Dewey Decimal System.

So I suppose it’s with several years of Professional Question Asking behind me that I ask this: Why do I keep getting picked on?

07/07/201107/07/2011

Why I Do Not Have a Smartphone.

I am finding that lately, I have had to defend my choice of telephone. I find this strange, as my telephone does exactly what I want it to do: It places and receives phone calls anywhere in America.

The fact that it does this, and that I pay about $35 per month for such services, seems like a good deal to me.

And here’s what I really like. My telephone does more than just handle phone calls. It can also send and receive text messages, which are growing on me as a legitimate tool for communication. It features voicemail, which is quite a bit more affordable than hiring a secretary to handle similar message-taking duties, and it has a few spiffy additional features, such as a tip calculator and alarm clock. The calendar function is especially useful, and can be used for such purposes as finding out what day it is.

Again, I thought this was a lot for a cell phone to offer.

The good folks at CNET had this to say about my phone:

“In any case, the SGH-A137 isn’t too much to get excited about. The simple flip phone is so basic that it doesn’t even offer an external display.”

Oh.

What I am discovering is that my colleagues agree with the editors at CNET. They tell me that more than my clothes, or my choice of automobile, or my chosen profession, my phone indicates what kind of human I am.

I thought my phone indicated that I was both sensible and uncomplicated.

Not even close.

Not even in a million, billion years. Just NO, Dan.

What my phone apparently signals to others is that I am, at best, uncool, and at worst, a lost cause. There is only one remedy for someone like me:

A smartphone.

A smartphone like the iPhone, or the Blackberry, or something that runs on Android. A phone capable of listening to a song on the radio, determining what song I’m listening to and then automatically downloading said song to the phone’s very hard drive. A phone capable of taking a photo and then rendering it in sepia. A phone capable of booking reservations at a nearby restaurant, testing my food for any toxins, chewing my food, paying my bill, getting me a taxi home, tucking me into bed and telling me a bedtime story.

A phone like that, or something.

I do not like that sound of that. Not at all.

See, I have a very simple mind. I actually like dividing up my devices into specific silos. I like reading on my Kindle. I like typing on my laptop. I like rocking out on my iPod. I like calling on my phone. This system works nicely for me.

And I suppose that, yes, I could get a singular device that could allow me to do all of those things. But I type slowly on a phone. I don’t like reading something on a three-inch screen. I like going for a jog and not having my music device start vibrating from an incoming text.

More than anything, I love disappearing. When I am at my computer, I respond to email. I write. I’m busy.

But away from that screen? I shut down. Work ends. I go out, and I enjoy life in this rather nice world of ours. If you need me, call me. I’ll pick up. But that email of yours will have to wait.

Give me a smartphone and I’d be in a state of perpetual Google. I’d be walking down the street and see a Curly W hat and ask myself, Who was it who hit 3rd for the Nationals in 2006?, and then I’d lose myself in the lifetime statistics of Jose Vidro, and then I’d pour over numbers on Baseball Reference, and then I’d find myself wondering what just happened to the previous 35 minutes. I know, because this is what happens at work. I take a thought, and connect it to another, and another, and then the time just disappears. I am good at wasting time, and on a smartphone, I would waste an awful lot of it.

My current phone? I don’t get lost in it. I make my call. I send my text. I move on. I leave myself time to stop and stare.

It is a phone that allows me to focus completely on what I am doing.

Of course, now that I’ve said all that: I’m going to get lost on the way downtown tonight. I’m going to need directions. A song will come on the radio, and I’ll want to download it. I’ll forget to make reservations at the place I’m headed. I’ll see something that demands to be sepia-ized. I’ll have an urgent email to send out.

And I’ll understand why everyone else has that thing in their pocket.

But me? No. Not yet. Not ever, I hope.