When You’re Lost, Don’t Be Afraid to Ask. And Definitely Don’t Be Afraid to Listen.

Let me take you back to 2009. Newspapers were slashing staff daily. Jobs weren’t plentiful. A young, wide-eyed Dan Oshinsky was about to graduate from college.

And in the midst of all this, a strange thing happened: A big newspaper chain decided that they really liked me. They liked my attitude and my skills. They told me, straight up: We want to hire you. We don’t know what for yet, but we want you.

Over the next few weeks, I had a number of phone conversations with one of the chain’s executives. The chain had just launched a big blog project at one of their papers, and they seemed really excited about the numbers. They had an idea for me: Start a blog for our papers devoted to young people and business. We’ll give you $100k and a small team to start. Give it a few days and come up with some potential topics for us.

Understand this: I was coming out of journalism school like most J-school students. I had great clips and great ambition. I was fully prepared to start working for a newspaper on a city desk or a political beat.

I thought I was totally unprepared to lead an ambitious, new journalism effort.

I didn’t know anything about business. I didn’t read business blogs. I didn’t understand the market for business news.

The next week, I told the executive: I’m flattered, but sorry. I’m not your guy for this project.

Looking back, I’m stunned at how stupid I was. I can’t believe that I said no, and I can’t believe that I failed to even produce a single tangible idea for such a blog.

How could I have been so unresourceful?

Over the course of about 72 hours, I was given the opportunity to pitch something really impressive. I had everything I needed to start such a project: I was ambitious, I had blogging experience, and I had a good sense for how to create a voice that was readable.

Sure, I didn’t know anything about business news. But here’s the thing: I knew plenty of people who did.

I didn’t ask for their help.

I could’ve turned to my network — my friends, my former bosses — and asked for input on ideas. I could’ve generated a really impressive proposal for that blog.

And I didn’t even think to ask.

What I’ve learned since is the importance of a really good conversation. You need people who can advise you, guide you and — most importantly — ask the kind of questions that will help lead to you the right answers. When you have an opportunity, talk about it with smart people. It’s amazing how a good conversation can really open your eyes to your full potential.

I was reminded of that last week. I was down in Springfield, taking meetings for my upcoming reporting experiment with Stry.us. And in the course of a half dozen conversations, I started to notice some new themes popping up. I suppose I had been thinking about these changes for some time, but it wasn’t until I started really talking it through with others that I realized how big these changes were.

I can’t begin to tell you how thankful I am to have smart people on my side, asking good questions and helping guide this project towards an even more awesome future. Stry.us will be be stronger because of their curiosity and wisdom.

When you’re starting something new, you have to keep your eyes open. You have to listen fully.

And for goodness sake: When you’re lost, don’t be afraid to ask. You don’t have to go it alone.

You shouldn’t.

03/19/201203/19/2012

Lovers of #Longreads Wanted: Stry.us is Hiring For Our Next Reporting Project!

I’m hiring four reporters for the summer for stry.us. Send your stuff to [email protected].

I’m looking for lovers of longform for a summer-long reporting experiment in the Midwest. You’ll be working with Stry [pronounced STOHR-ee], a new reporting agency that’s trying to take a snapshot of life in 2012.

I’m looking for reporters who love to listen, who stay persistent on new beats, and who just can’t get enough of stories.

The job is for three months this summer. Money, food and shelter are included. You’ll need to find your way to the Ozarks, too.

If you’re curious, click here and send me three things:

1. Your résumé
2. Your online portfolio
3. Two links to awesome stories you’ve read this month

I don’t care what type of stories you specialize in. If you love stories, and you want to be a part of big experiment in storytelling, I want to see your stuff.

No cover letters, please. If I like you, we’ll talk.

-Dan
[email protected]
@danoshinsky

(FYI: Stry.us is undergoing a facelift right now. I’ll lift the lid on the new site in April. In the meantime, if you’d like to read some old stories from Stry, you can check them out at this link.)

02/08/201201/26/2012

What My Head Feels Like Right Now With All The Things Happening With Stry.

Fast. It’s moving so damn fast. So many things to cross off the to-do list. So many things happening all at once. So many tasks. Knock one off, another one takes its place.

Slow. It’s moving so damn slow. So much time between now and May, and May just won’t come. Why can’t it all just come faster?

So fast, and so slow.

And yet I know: A thousand baby steps to get to where I need to go.

01/21/201201/23/2012

I Cannot Codify Entrepreneurship, And Neither Can You, And Here’s Why.

There was a point not all that long ago when I was pretty sure I could codify entrepreneurship. I’d heard plenty of stories, and talked to plenty of entrepreneurs, and I was seeing a lot of the same themes repeat. I thought that if I could just ID specific points along the way, I could explain how to master this thing.

Then I discovered that this isn’t a board game. There aren’t logical, sequential steps. There are common themes, but there isn’t any sense to how this works. Entrepreneurship is a cross between a Choose Your Own Adventure book and Mad-Libs — it’s weird, and deeply personal, and subject to both non-sequitors and randomness.

I read this fantastic quote from KissMetrics’ Hiten Shah that reminded me of just why that is. It’s in a post about how to find the right mentors. He writes:

“That’s the thing about mentoring that people need to understand: It’s about the strength of the individual to weather the unrelenting storm that is entrepreneurship, not acquiesce to some rigid timeline of entrepreneurial life milestones.”

Spot on. Entrepreneurship is this mix of all the stuff I love about life — it’s risk, and chance, and success, and failure, and this quest to be unrelentingly awesome — just condensed into something tangible. It’s the venue through which I’ve chosen to explore the world, and nobody’s going to be able to tell me what the right path is, or where the milestones are.

The only path is the one I choose, and the people I surround myself with have to be capable of helping me answer the questions I need to answer along the way. I need to find lots of people who can challenge me, and who I can listen to. But ultimately, they’re not going to be able to tell me if I’m doing this thing the right way.

The only way to figure that out is to do it and see what happens.

01/12/201203/02/2012

What the Hell Do I Do Now With Stry? (Part II)

If you missed Part I of “What the Hell Do I Do Now With Stry?”, you might want to read that first.

So the question for me now is, With what I know right now, what the hell do I really want to do with Stry?

Financially, I’m alright. I have +/-$45,000 left to spend on Stry. I have +/- 5 months to spend it.

So here’s what I want to do:

I want to tell one great story. I want it to be about this country in 2012. I want to call it, “Interconnected America.” I want it to tell the story of how we’re all tied up together in this thing, how immigration in Alabama and health care in Iowa and poverty in Detroit are all intertwined. I want to tell the story of where we, The People, are at this very moment, and what is keeping us from being all that we hope to become.

I’m going to set up a home base somewhere. I’m not sure for how long — maybe just a few months. I’m going to bring out some reporters. And we’re going to get to work.

I promise this much: Stry is going to dig deeply into the problems that Americans are facing in 2012, and Stry is going to bring you stories about the issues that are at the heart of this upcoming election. I promise great reporting and great storytelling. I promise to make you think.

❡❡❡

For me, personally, I also want to prove a few things:

-That I can put together a band of reporters.
-That this team can tell some amazing stories.
-That I can lead this team.

I also want to prove three additional things:

1. That I can syndicate Stry content to publishers. I want to prove that great content deserves a wider audience in print. I want to find the two, three, five publishers who’d like bring Stry to their readers. I want to get my content in their pages.

2. That I can produce an independent print product. I’m not sure if this is a book, or a Kindle Single, or a Stry Magazine. But I want this reporting to find a forever home beyond the web.

3. That I can build a community around these stories. The thing I really want is to put on a live event. I’m thinking of calling them StrySessions. It’d be an evening of discussion about a topic. Stry presents some of our stories — live — and brings in experts to discuss these topics. I want to see the community that Stry builds around this reporting.

So that’s the goal going forward: Tell a great story. Syndicate the content. Produce a printed product. Host a live event.

That’s what I want to do with the money I have left. All I ever really cared about is the storytelling. I want to prove how amazing stories can be, and I want these stories to help others understand our world, and if this doesn’t make me a cent, it won’t bother me at all.

The value is in the doing, and it’s time for this company to step up and do what it was built to do:

Tell great stories.

01/12/201201/12/2012

What the Hell Do I Do Now With Stry? (Part I)

This is Part I of II. Skip ahead to Part II if you’d like using this very link.

18 months ago, I was working at a TV station in San Antonio. I saw that journalism was changing, and I knew I wasn’t a part of the conversation. Every time I saw an interview with a news CEO who said, “There’s a 25 year old out there with the answers for our industry,” I wanted to pull my hair out.

Because I was only 22.

I knew I wanted to be a part of these conversations about the future of journalism, and I sensed that the only way to get there was by doing something big.

So I started Stry.

Above everything else, that’s why I started Stry: To be a part of the conversation about the future of journalism. In the 18 months since, I’ve gotten into those discussions. I’ve been invited to conferences. I’ve spoken at an event where my lead-in was the managing editor of the Washington Post. I’ve talked with people who have more zeros in their bank accounts than I have letters in my last name, and they’ve given me the time to discuss Stry and my ambitions.

Am I a big name in the room? No. But I’ve taken some huge steps from San Antonio to get myself into the conversation.

I’m proud of that. And if that’s all Stry did for me — get me a foot in the door — it would be enough.

❡❡❡

But Stry’s done more for me than just that. It’s also given me amazing opportunities to prove myself.

For one, I wanted to prove myself as a reporter. 18 months ago, I asked myself: If I showed up in a place where nobody knew my name, and nobody knew who I worked for, could I still tell great stories?

Biloxi answered that question for me.

Hell yes, I can.

I also didn’t know jack about business 18 months ago. I’m not sure that I could’ve told you the difference between profits and revenues. I thought QuickBooks was something you could read on your Kindle. I didn’t have the skills, let alone the vocabulary, to work in this world. I didn’t really understand the business behind journalism.

Today, I’m miles ahead of 2010 me. I actually understand this stuff. I’m not an MBA or anything, but the basic underpinnings of business are no longer a total mystery to me.

And biggest yet, as far as I’m concerned:

I learned how to take on risk. I mean, actually shoulder risk. I learned how to take responsibility for my actions, and I learned that I don’t really care if something I do doesn’t work out. Just the simple action of doing — of coming up with an idea, of putting it into motion, of sending it out into the world — is an amazing thing.

Take BooksAround. For that project to get off the ground, I had learn to code. I had to build a website. I had to attempt a Kickstarter campaign, and fail. I had to get back up off the mat, find some money, find some books, buy some books, create a system to document and process all the relevant data, find the people to read the books, and ship off the books. The day that the first books went out was a proud, proud day for me.

❡❡❡

Okay, so a question that’s worth asking:

18 months ago, Dan, you promised to deliver Stry, a nimble news syndicate. You promise to build an editorial team, outfit them with the right tools, send them out on the road, syndicate that content to news organizations, and get those news organizations to pay you for that content.

Did you actually think you could pull that off then? And can you pull it off now?

The answers, one at a time:

Yes.

And maybe.

When I left Texas, I really did think I could pull this off. I saw an industry crumbling. I saw publishers who were angry about how much they were paying the Associated Press for the same content that everybody else has. I thought I could do it better.

I still do.

But everything I was doing was kind of rooted in this one core belief: I really thought I could save news publishers.

I’ve stopped thinking that. Publishers were handed the Internet, the greatest distribution channel in human history, and that hasn’t saved them. They were handed social media, and new ways to engage audiences, and that hasn’t saved them. They were handed the most advanced technology we’ve ever created — DSLR cameras and smartphones and iPads and Final Cut — and that hasn’t saved them.

Point is, me and my merry band of reporters weren’t going to save journalism.

Really, the idea of “saving” this industry is wildly misguided. The deeper I get into this world, the more I see two big conversations happening about journalism.

The first is the big conversation. They’re the 90-whatever percent of journalists who are kind of love with their own demise. They’re the ones who can’t stop talking about how screwed they are. I used to be one of these people.

I’ve realized that I can’t help them. Or more specifically: I can’t fix them.

But then there’s this second conversation. It’s just a little undercurrent. But it’s a room full of people looking at all the amazing tools we have at our disposal, and we’re asking: How can we make journalism more awesome? How can we tell great stories? Let’s shut up for a second about the state of journalism and talk instead about the state of storytelling, because there’s never been a better time to tell stories. So let’s do it!

The secret among this second group is that we know if we do an amazing job telling stories now, in the long run, we’ll be able to build successful businesses around that reporting. So let’s tell some great stories right now, and remind the public of why they love and need what we do.

We have to do that now so that in 10, 20, 50 years, we can have a healthy industry. It’ll take time, but we’ll get there. I really believe that. We’re a society built on narrative. At the root of everything we do, we have stories — stories about who we are, and why we do what we do, and where we’re going. Great storytelling isn’t going away.

So the question for me now is, With all the things I’ve learned, and all that I’m seeing, what the hell do I really want to do about Stry? Those answers in Part II of “What the Hell Do I Do Now With Stry?”

10/24/201110/24/2011

Treetop Flyers Wanted.

I’ve been thinking a lot lately about the kinds of people I’d like to hire for Stry. I’ve been asking myself, Who’s going to join me on this startup adventure? Where am I going to find reporters willing to chase stories and travel and venture forth into a world where the only structure is the one we define for ourselves?

And lately, I’ve been thinking that I’ve got to find some treetop flyers.

See, back in Vietnam, the American military trained pilots to fly low-altitude, high-risk flights. But when those pilots returned from war, there wasn’t much need for someone with such a skill set.

So, the story goes, these pilots became treetop flyers: Smugglers, drug-runners, danger-seekers. They took risks that other pilots wouldn’t take; they flew places that other pilots wouldn’t fly.

They were outlaw pilots, and they were much in demand.

I’ve used a lot of words for the type of reporters I’ll need for Stry. I’ve referred to them as hobo journalists, as backpack journalists, as reporter vagabonds.

But what I’m really looking for are treetop flyers: Reporters with skills that no one else really values, reporters who aren’t afraid to fly a bit too close to the ground, reporters willing to go at it without a safety net, reporters for whom adventure is just something that happens when they show up at the office. Working for Stry isn’t going to be a glamorous job. It’s going to be a lot of work, and it’s going to require a hefty amount of improvisation. My reporters at Stry are going to have to deal with stress, strain and general chaos without spontaneously wigging out.

I need reporters willing to go to the Biloxis of the world, willing to dig where others aren’t digging, willing to crash and burn and get back out there the very next day to do it all over again. I’m looking for a new kind of a reporter.

I’m looking for treetop flyers.

Apply within.

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.

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”]

05/02/2011

The Very Exciting Thing That Is About To Happen To Me (or: M-I-Z).

This post was originally published over on Stry. It’s actually a speech that I intended to give in Columbia, Mo., last week. I didn’t know I was supposed to give a speech, and then I decided to read the itinerary of events I’d been sent, and saw very clearly the words “Dan Oshinsky” and “five-minute speech” linked together, and suddenly, hastily, began writing. Turned out that they decided to not have me speak — wise move on their part, I should say — but I’ve regurgitated the vague outline of my would-be speech here:

Motion is kind of an amazing thing.

I feel like I should know. I went skydiving last week.

I’m not exactly the skydiving type. I’d never been skydiving before, or bungee jumping, or heliskiing, or anything that involved a significant amount of free fall. I’m also not a fan of heights. So you can guess how strange it must have been for me to be sitting on the floor of a four-seat Cessna, 10,000 feet above Warrenton, Va., strapped to a guy named Dave — white hair, white eyebrows, used-to-be-a-roadie-in-Joplin, Mo., Dave — when the door to the plane opened, and I looked down.

And I surrendered.

Surrendered to the overwhelming, crippling fear, for one. But also to Dave, because he was literally harnessed to my back, and he was going to throw me out of the plane whether I was ready or not, and he was also the guy who controlled the parachute, which meant that he would be deciding whether or not we landed.[1. Well, safely, at least.]

I surrendered. We jumped.

I was thinking about that last week. I think there are two types of media organizations out there: Those willing to surrender to the current media climate and move forward, and those that aren’t.

It is not enough to merely acknowledge that things have changed for newsrooms and news organizations. Some fight what’s happening, some fear it.

Some surrender.

That’s the smart choice.

One type of new media organization gets me especially excited these days: The startup. These are organizations that sense opportunity, chance, uncertainty — and are putting themselves in motion to chase their ambitions. I find that to be a remarkable thing.

So this year, I’m going to get a bit closer to them.

The University of Missouri’s Reynolds Journalism Institute (RJI) has invited me out to Columbia, Mo., in the fall to serve as a fellow.[3. The list of former fellows is long and distinguished, and I am not entirely sure how I now find myself among their ranks.] For a year, I’ll be studying news-centric startups, trying to catalog the choices, successes and failures made during their early stages. I’ll be applying those lessons to Stry, the startup I founded last fall in Biloxi, Miss.

Despite all the success I had in Biloxi, Stry has been idling since the fall. RJI is giving me the chance to kick-start Stry once again. During the course of my fellowship, I’m going to try to take Stry from concept to realization. The goal is to build out an organization that can begin reporting and syndicating stories starting in the spring of 2012.

Better yet is that I’m going to try to bring transparency to the process. I’m going to put Stry inside the fishbowl for others to watch and participate in the startup process. My successes, my failures — they’ll all be public.

My hope is that by opening up the process, we can give other could-be founders the chance to see how challenging the startup process can be. If we do it right, we’ll give them the chance to start their company at a place greater than zero.

Do that, and we give them the chance to put their company into motion faster.

And motion — motion is kind of an amazing thing.

photo at top by Dak Dillon