Opening Day and Busting Brackets


Since it’s Spring Break, I took a mental break from various “real world” things this week. Which apparently means geeking out on “sports-are-metaphors-for-life!!!” analogies.

Two of my favorite parts of baseball season: The first day of Spring Training and Opening Day (which kicks off on Sunday). Because those times are the ones filled with so much excitement, wonder and curious potential. Kind of corny, but I can’t help but feel a little giddy from tweets like these:

And from a dated but still relevant blog post that caught my eye, “Innovators are Bracket Busters“:

Innovators, in their way, are bracket busters. While incremental improvements can be accomplished by working within current brackets and seeds, the biggest opportunities to create value come from transformational change, the kind of change that requires bracket busting. Solutions for the big social system challenges we face, including education, health care, energy, and entrepreneurship, require more than incremental change. The solutions we need require transformative bracket-busting business models and systems.

Don’t be constrained by brackets created by someone else. Create your own dance. Be the top seed in your own bracket. Be an innovator. Be a bracket buster.

Play ball.


On the process of organic growth


I don’t mind doing targeted marketing and outreach, but I’m a bigger fan of the organic growth process. A few entertaining experiences from casually talking about my project this past week:

I accompanied a friend to a post-art show dinner, and the project came up in conversation with an adjunct art professor at CUNY. At first he said he wasn’t a big sports fan but eventually started remembering moments from his childhood as a Giants fan. (This, by the way, is part of the reason I love sports journalism — sports bring out emotion (both good and bad) in such a unique way in people.) I had similar conversations with others, and it was a good experience to talk about the site among a non-sports/journalism crowd.

An email chain started to get try to get others to join a March Madness pool at my company. Some people didn’t want to join because they hadn’t been keeping up with college basketball. I interjected that March Madness is for even the under-informed (and referenced a relevant post on the site). Taking some smack for a suggested pick in the post was a small price to pay for the new newsletter subscriber (and added visibility) I got out of it.

I think my favorite was my sister’s response in an email when I asked her to read through something: “And of course I’ll help read through! …even though I am very excited for you, I’m glad you couldn’t see my face fall when I read ‘It’ll be on baseball.’ Sigh.” (For context, my sister is not a sports fan and begrudgingly entertained my fascination with baseball growing up.)

I don’t exactly have a clear conclusion, but I enjoyed these conversations and while playing around in PowerPoint (aka procrastinating other work) came up with this 2×2:


Big picture vs. little picture tug-of-war


Sometimes it’s tricky to balance between “big picture” ideas and “little picture” implementation.

I met with someone who offered suggestions about creating a mobile app, and I’m trying to soak everything in but thinking in the back of my head, “Uhh, I’m still trying to figure out how to change the dimensions of parts of my homepage…”

I practiced tweeting explanations of baseball rules during a spring training game to about 15 followers, and later that day, met with someone who wanted to explore possibilities in back-end data collection/analysis of viewer behavior during sporting events.

I had conversations with an editor at about developing content to reach millions of readers of a fashion website, and then turned inward to try and figure out how to get more than 20 newsletter subscribers.

All of the “big picture” conversations were beneficial and helped me think about revenue streams, business models and customer preferences. But I admittedly had more fun reading through comments from newsletter subscribers (who are mostly friends and family at this point) and experiencing the “aha!” moment for a friend as he went through a football explainer on the site.

So as much as you want to take in others’ ideas and genuinely consider them, it’s also important to keep sight of the reasons for launching the project and have fun with it! Which seems like a “duh” observation when I write it out, but it’s helpful to remember when I’m inundated by too many “big ideas,” get too far into the weeds of a particular task, or get derailed by other “real life” things that come up.

A few other things:

Content strategy, version 219837294! For now, focus on the newsletter as my MVP; let explainers, glossary terms and eBook ideas develop as a byproduct of that.

Outbrain observations: I got a lot of traffic but a high bounce rate and no newsletter subscribers. The majority of the traffic came from sports sites like ESPN and, which isn’t my target audience. Quick conclusion: Sports are a popular topic and there’s potential there; I need to figure out how to reach my target audience of “casual fans” better.

Lessons learned in tech, pitching and design


A lot of things are learned in unexpected ways. Which I (mostly) love because it keeps me on my toes. Here are few of my lessons learned from this week:

  • From Outbrain to Namecheap to WordPress: I set out to try Outbrain, a referral service that helps drive traffic. I signed up with my site’s email address, but couldn’t receive the verification email. Which sent me into a fun adventure of frantically digging into Namecheap FAQ, googling “how to’s,” and pestering friends to send test emails. Eventually, with the help of the very patient CUNY web team, I learned useful things like the difference between email hosting and email forwarding, that it’s probably a good idea to test out the email address you list on your site if you tried to code it yourself, and that you can’t install a new plugin on the CUNY server without prior approval. In addition to learning how Outbrain works! Good times.
  • Pitching can be pretty fun: We attended a Start Up Pitch Night meetup and several of us gave 60-second pitches. I was undecided going in, but ended up doing it –it was a good opportunity to practice in a no-stakes situation (and the moral support of fellow Tow-Knighters was helpful!) Overall, a good experience and I got some useful feedback, although I’m realizing that what ends up coming out is always different from what you plan in your head — I said my purpose for being there was to spread the word, and then forgot to mention the site’s URL. Minor detail. #nexttime
  • The “do what you do best and link to the rest” mantra applies to design software too. I’ve bounced back and forth between different options for graphics, trying to balance efficiency and the quality of the end-product. For now, PowerPoint/Keynote are more effective for things beyond simple logos. I’m undecided about Piktograph — it has nice templates, but feels a little unwieldy to use. Maybe a Photoshop workshop will happen one day.

Oh, and don’t let things on the to-do list like “laundry,” “haircut,” and “call mom” slip for too long!

When do you start marketing even an unfinished product?


From a very helpful recent conversation: “If people aren’t going to your site or signing up for your newsletter, isn’t that something you want to know now?

I stopped by Skillcrush’s offices to talk to Adda Birnir (co-founder and former Tow-Knight fellow). It’s always helpful to hear about the experiences of others, and it pushed me to make more concerted effort to figure out how to market my site and drive traffic to it. My hesitancy (and kind of pathetic efforts to do so thus far) I think came from getting caught up in trying to perfect certain details and uncertainties, and worrying about showing a product that’s not ready too early. (Adda also had a helpful response to that: “You’re going to have to get over that.”)

The thing about start-up culture–as opposed to some traditional media outlets or other industries–is that sometimes you have to market/promote a product that’s still at a very early stage of conceptualization. And during the process of marketing, you learn things that help shape the ultimate product so that it fits the audience’s needs better.

It’s a different kind of process compared to content strategy/development, but I like that it forces me out of my comfort zone, and I think it will be interesting to see how different approaches work. And it’s true: If what I’m putting out isn’t something that has traction, better to know that sooner rather than later. And then make adjustments and try again.