Hey there! It's Ben

What a Month! It's Ben (May 2022) — Launching a T-Shirt Brand

Published almost 2 years ago • 6 min read

Welcome to the inaugural ‘What a Month! It’s Ben’ newsletter! I’m so grateful for all of you for following along.

This past month I launched a t-shirt brand, took weekend trips to Chicago and Denver, and brewed beer with a buddy. For details, read on below. And if anything I share resonates with you, I’d love for you to shoot me a reply!

Launching a T-Shirt Brand

On May 1st, I kicked off my self-directed master’s program by creating Downside Up – a brand of t-shirts with graphics falling out of upside-down pockets. In addition, I wrote an article about why, after spending seven years running a software company, I decided to make a t-shirt brand my next business venture.

I spent my first few weeks preparing to launch the brand (which I documented daily via Instagram stories and a Twitter thread) and went live with the online store on May 18th. By month’s end, I sold 19 shirts – all of which were bought by friends.

There have been both highs and lows from the experience. On the positive side of things, it felt unbelievably cool to sell a product of my creation over the internet for the first time. I’ve learned a ton from the process of getting Downside Up off the ground. And I’ve been so appreciative of my friends’ support throughout. It’s been daunting and uncomfortable to create my first e-commerce brand, especially while doing so in such a public way. I’ve feared judgement, failure, and everything in between. Yet the outpour of encouragement and feedback – both in person and over social media – has been empowering and made the brand creation process feel a lot less lonesome.

On the flip side, it’s frustrating to have not yet have made a sale to a stranger over the internet. Honestly, I kind of thought that would be easier and more formulaic (create product → launch website → run ads → product sells). In retrospect, of course I should have known that selling products online is a hard-earned skill that takes time to develop.

Over the past two weeks, I spent a lot of time reading, watching YouTube videos, and chatting with friends about all-things digital marketing. And while part of it felt like wasted time (“I should be doing things, not watching YouTube videos!”), I do feel like I came out of the month feeling more comfortable about what it’s going to take for online sales to click.

Moving forward, I’m excited to see if I can solve this “selling things to strangers over the internet” puzzle. There’s certainly no shortage of things to try (between better ads, better ad targeting, TikTok, influencers, referral programs, etc). Hopefully some of these attempts will hit and I’ll have some fun updates to share in next month’s newsletter. And if any of y’all have ideas on marketing efforts that might work, I’m all ears!

The Downside Up Website


I popped over to Chicago from May 6th-8th, both for Mother’s Day and my friend Ben’s 30th Birthday Party. I spent Friday and Saturday night partaking in birthday festivities with Ben. And on Mother’s Day, my parents and I toured the Driehaus Museum – a restored Gilded Age mansion (nicknamed ‘The Marble Palace’) in the heart of the city.

After spending my entire life in the Chicagoland area, I took for granted how easy it was to see family and friends. But since moving to Austin in October, visits home now require effort and planning. I was fortunate to have two unique reasons to visit, as they combined gave me the push I needed to make the trip happen. And it was really special to be there for both!

Nonetheless, I would have loved to have had more time and seen more people while in town. To make up for it, I’m planning at least one longer trip to Chicago this summer so I can spend quality time with family and friends in the area.

Mom and Me Outside the Driehaus Museum


On May 13th, I flew to Denver for a jam-packed weekend. I met up with friends at a brewery, went on a hike with my cousin, saw the band Turnpike Troubadours perform at Red Rocks Amphitheater, and attended a Rockies game.

While I’d pseudo-been to Denver before (ski trips, work trips, and road trips), this was my first time truly exploring the city. And I have to say, I came away incredibly impressed! The weather all weekend was perfect and everything we wanted to see and do was accessible by foot (including the Red Rocks bus pick-up site). The bars and breweries, street art, walkability, and overall atmosphere of where we stayed (RiNo) reminded me of where I live in East Austin. Another reminder of Austin came from seeing a skyline full of cranes building up the growing city.

Of everywhere I’ve been, Denver has my favorite bar and brewery scene – mainly due to the unique caliber of activities they offer. One brewery we went to had mega corn hole, where we threw what felt like beanbag chairs into a corn hole set that came up to my shoulders. They also had a large beer pong-esque game set-up where we chucked volleyballs into oil drums. And I’m not just saying this based on a singular spot: on a previous visit back in 2016, I went to a bar that had a full-scale volleyball court in their back patio (okay, maybe a sample size of two isn’t much better, but I’m still standing by this claim).

I know this is not an earth-shattering observation to make, but the nature in Denver is exceptional. There was something incredibly cool about being in the heart of the city and seeing mountains in the distance – and then driving 30 minutes and hiking those same peaks. And the open-air concert experience at Red Rocks was every bit as awesome as I was hoping it would be (despite being resigned to the last row).

Overall, I had a great four days in Denver and look forward to exploring more of the city on a future visit!

Photos from Denver

Brewing Beer

On May 30th (so, yesterday), my friend Joey and I brewed beer!

Brewing had been on my list of things to try for a while. I shared that with Joey after he handed me one of his home brewed Hefeweizens a couple of months ago, and from there we made plans to make a batch together.

Joey already had the required equipment. So once we ordered a pilsner recipe kit from Northern Brewer (that included hops, malt, yeast, grains, and priming sugar), we were ready go!

Since both Joey and I had electric stoves in our apartments, we sought out a gas stove that we could use for the process. Fortunately, my friend Max came in clutch and allowed us to use his home for our brew day.

So we transported the supplies over and went to work! Over the next several hours, we sanitized equipment, boiled liquid, steeped our grains, sanitized some more, mixed in our malt, hops, and yeast, and cooled the liquid in an ice bath. By the end of the afternoon, we had a five-gallon bucket full of pre-fermented pilsner ready to roll!

Did we nail it? Well, I’m not yet sure! In two weeks, we’ll refrigerate the solution. In six weeks, we’ll bottle it up. And in eight weeks, I’ll let y’all know if it’s enjoyable (or at the very least, drinkable) 🤞

Brewing Beer with Joey

Friends Doing Cool Things

On May 9th, Ryan Deitrich went live with his first AirBnB property. Why is that a big deal? Well, Ryan bought the Philadelphia three flat in shambles and spent nearly every day over the course of two years rehabbing it by hand into what he hoped would turn into a cash-flowing asset. Within hours of going live with the listing, he had two months of the mortgage paid for. Talk about delayed gratification! Ryan is currently fixing up property number two — a log cabin in the Poconos.

Monthly Favorites

Article: Letter to My Younger Self by Tarik Cohen – In this powerful essay, NFL running back Tarik Cohen writes about unimaginable tragedies and the guilt he feels over the familial costs of pursuing his dreams. It’s a heartbreaking story of a young athlete who dreamt of using the NFL to lift up his family, overcame the odds to make that a reality, and yet still feels like he let his loved ones down by failing to be present in the process. Tarik has been one of my favorite players since he entered the league, and I’m rooting hard for his comeback.

Song: Purple Hat by Sofi Tukker — This song is not new. Nor does it likely inspire much confidence in my musical taste as my inaugural “song of the month selection.” But I’ve been listening to it on repeat for several weeks now, so it felt disingenuous to share anything else.️ Fun fact: Tucker Halpern (one-half of Sofi Tukker) started DJing after an autoimmune disease prevented him from continuing to play on the Brown basketball team.

Til next month,


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