On Deck Writing Begins!

Drew Stegmaier
5 min readFeb 1, 2021


I first heard about On Deck on the Clubhouse app. Based on that, I called it Linkedin meets The League. It wasn’t recommended. But I kept hearing about it.

Have you received an unprompted refund just because the service was meh? Tom, a writing partner at On Deck, sent me an unprompted refund for a random project we worked on, just because it wasn’t a win-win. Cue the guerilla marketing for On Deck. 🦍 Trust level 💯 achieved.

When a smartie-pants recommends something, you think about it. When four smarties you deeply respect independently recommend On Deck, you apply for On Deck. Their growth loop got me. A-Players want to play with A-Players. I want to play with them, too. 😜

The word of mouth kept coming.

I heard that On Deck has impromptu freestyle rap. That helped sell me. It told me that these people experiment and understand that having fun is important. It’s ok to act a fool sometimes. Freestyle rap is an incredibly creative activity. I’ve been writing raps since fourth grade.

Prior to On Deck, I made a plan to turn pro as a writer. I’m living on the cheap in Brazil to slow my burn. The plan is simple- savings go down, I write a lot, income goes up. We will see.

Tom has this Field Of Dreams idea. The movie says “if you build it, they will come”. But the internet doesn’t work that way. If you build it nobody shows up. You have to build and scream from the rooftops. Then people might show up. Then you build more and keep screaming. Tom told me that I have good stuff, but I need to focus on distribution. Just writing a lot, even if it’s Hemingway-esque, doesn’t mean anyone will read it. Hmm…this adds nuance to my little plan. Again, guerilla marketing for On Deck — Tom was just being a good dude here. This nugget of advice was so good that I unrefunded part of the refund.

I’m clueless about marketing, not one of those marketers learning how to write. None of my articles are search engine optimized and words like backlinks and ahrefs (pronounced like A-H-refs for normal people) make me want to puke. 🤢 I’m pretty sure Stephen King and JK Rowling don’t ponder the intricacies of SEO.

But a man’s gotta eat. If you want to go fast, go alone. If you want to go far, go together. I want to go far. To create a body of work. To stop selling my time and start selling my creations. The savings are dwindling, and I thought the geniuses over at On Deck could help.

I looked up the On Deck Writing (what we call ODW) program director, Max. I creeped on his website and got good vibes. It’s weird, but the good kind of weird. 👽

Sometimes the universe beats me over the head with a stick, encouraging me to do something. I was sold about On Deck because it felt right and the diligence checked out. I had a good vibe. I’m sure that sounds cheesy as hell but it’s true. We have neurons in our brains, hearts, and our guts. All three of them told me this was a good idea.

I put something in my application about “undervalued ideas”. I thought that sounded clever. Somehow, I scored an interview. I’m too candid to be good at interviewing. It’s my superpower and my kryptonite. Somehow I also scored a scholarship. On Deck is for rich people and I’m not money-rich yet. The whole process was very human. I hate applying for things and feeling like a cog in the wheel. These people treated me like a human being.

Before the cohort kicked off, a deluge of emails stormed my inbox. On Deck is remote, but they don’t want to leave you hanging. The emails got me up to speed before the cohort officially began. Right now we are wrapping up week one, and I’ve already had a ton of Zoom calls. Zoom and Slack are the primary delivery mechanisms for On Deck. Some of the calls are regular programming. Others are meet and greets with strangers, now kindred spirits, from the community. Roger Farley hosted an event the first week explaining how to make the most of the experience.

He’s a legend at On Deck and did seventy-two one on ones during the first cohort. On Deck uses the phrase “buffet style” heavily to describe the schedule. You will have dozens of Zooms over the eight weeks. Roger averaged 1.28 zooms per day, every single day, in addition to all of the other events. Bonkers. He recommends a heavy dose of meeting other fellows.

I listened. Just this week I had a one on one with him, Ashish, Rand, Jamie, and have three more scheduled with Ajay, Jennifer, and Charlene. I’m not good at half speed. I prefer to learn by firehose.

Also this week I had a mini-crisis at On Deck. I firmly believe that Comedy Is So Crucial Right Now That It Isn’t Funny 🤣 . I’m terrified of censorship. It is where creativity goes to die. I was in another community and got a talking-to for a piece titled Intellectual Masturbation: Short Story Club. Is the title edgy? Yes, that is the point. That is what makes me, me. Exploring my edge.

I was scared that On Deck was going to water down my stuff, too. That’s terrible. Writing bland crap is the best way to ensure you fail. We hopped on the phone and hashed things out the same day. Edgy writing is welcome. That’s what makes art, art. But, that isn’t a license to be rude in public forums. Nude modeling is ok in art class but you can’t walk down the street naked. Context is important. I was impressed by On Deck’s level of care around the delicate subject.

This paints some of the picture of my first week at On Deck. My program scholarship is contingent upon my role as a scribe. That involves writing weekly articles about my experience. I’ll do my best to keep things real. While I’m not getting paid to say this, it felt wrong to hide it.

If you’re on the fence about On Deck, feel free to keep reading these weekly updates. And, hit me up to chat. I’d love to talk with you. I’m drew at stegdrew dot com — my world is small enough that I feel ok letting this into the wild. To be inundated is a good problem to have :)