2018 — My year in review

Like I do every year, here’s my attempt to wrap-up the year w/things I did and things I learned. 2018 was crazy on so many levels and one of the most impactful years I’ve had yet. I’m sure there’s some sort of bias that creeps in at the end of the year that leads to that conclusion but I truly believe, even accounting for that bias that 2018 was my most transformative year yet — lots of ups and downs, lots of changes, and lots of lessons learned leaving me in a position where I’m still figuring shit out just like the rest of the world.

However, I’m happy w/ my position and excited for the new year so cheers to 2018 and cheers to a new year happening in about 3 hours 🍻

Things I did

• Went to Hangout (my first real music festival @ Alabama Gulf Shores)

Hangout Fest, 2018

• Officially closed a $1.6MM round of investment for Rapchat (an awesome, Rapchat team effort)
• Visited my Aunt and Uncle on the Plum (Plum Island, MA) — one of my favorite places on earth
• Watched a couple friends get married
• Went to ITALY w/mi famiglia which was the trip of a lifetime and merits it’s own, long post. The short of it is that my Grandparents paid for a 10-day trip for my Mom’s side of the family (uncles, aunts, cousins) to explore the Southern parts of Italy. We got to visit Sorrento, the Amalfi coast, Pompeii, Napoli, Lecce / Puglia, and most importantly Vieste which is the small, coastal town from which we’re from

• Fell in love and moved in w/ my girlfriend who is amazing on so many levels (could write 1000+ words more about her but will save the inner Romeo for another time) … it marks my first time living w/ someone so pretty big change for ya boy, excited to see what the future holds here

Random things like building things, Friendsgiving, getting a tree (yes, she’s low key charging at me with w/scissors there), and more

• Went to Canada w/ the boys again — the trip was unfortunately cut a little bit short this time but per usual, had an incredible time w/ some of my best friends (and our squad won the annual golf scramble 2nd year in a row) in the amazing country of 🇨🇦

Buckhorn Lake, 🇨🇦

• Went to Browns Home Opener — “We didn’t lose”

First of many more Home Openers to come

Things I learned

• Tons, tons more about running a startup (lessons learned everywhere from fundraising, leading, managing employees and relationships, product mgmt/dev, engineering, design, recruiting, managing investors, and countless other areas I can’t think of off the top)
• A major lesson learned re: startups is that it’s easy to get lost in the sauce when running one. The challenge is both ‘on and off the field’ … balancing managing a company, yourself, the people that count on you, etc is a massive challenge and just finding ways to do what needs to be done without losing your mind is half of it
• I didn’t save a ton of time for working on myself or some of the other things I wanted to accomplish this year (like making progress on volunteer initiatives, reading/writing more, staying active, etc) so working on prioritization and organization will be big next year
• Related in some way to all things I learned, you have to be cognizant of the energy you spend in general … whether at work or elsewhere, you have to protect your energy, watch out for stupid things you spend it on, and invest more in things that matter. It’s easy to get stuck going through days without even realizing that you just got sucked into dumb conversations, social media storms, news cycles, and more. It’s also easy to lose track of visions, missions whether personally or in business so taking steps away to even just think without any distractions is extremely helpful with this. Drake’s song Energy is one of my favorite reminders when it comes to understanding this dynamic
• Continuing on energy — it’s not easy to find a balance w/the news cycle when our President is a fucking idiot. It’s also not easy to find the balance between caring, conversing, etc about the countless awful things that are happening in our country and staying sane, focused on other tasks
• Learning about yourself is both uncomfortable and necessary to grow as a person and being able to answer questions like what is your why, who are you and shit like that (which for me is a major work-in-progress) is essential. Because of this, I’m continuing to invest time and energy into learning more about me and building a strong foundation. Building a strong foundation makes you unshakeable — it helps guide you and gives you the ability to proceed in life without having to worry about what people think because you know what’s right and you believe in yourself. It’s SO clear that some of the people I admire just inherently know why and what they’re doing at all times (e.g. — Elon, Lebron, etc). I want that Lebron-type foundation.
• This digital age is full of distractions and unhealthy habits that are pretty hard to avoid. You’ll never escape them all unless you get rid of your phone completely but it’s necessary to avoid in times where the focus is needed. I personally love Twitter (especially 1PM on Sundays when Browns are playing) yet even just Twitter can build a pretty toxic habit, especially when King Dumb Dumb and Kanye go on insane tweetstorms. Getting back to silencing as many notifications as possible while working is another tiny goal of mine for next year.
• There is no right way to do anything. The internet and even this site, Medium has spawned an insane health, mindfulness, optimization movement. Admittedly, I’ve fallen for it before. It’s an easy trap to get hooked on ‘optimization’ or ‘health’ but it’s also overload. The dudes who run Basecamp like DHH and Jason Fried lead a movement with their books and philosophies on working/life strategies in addition to every major news site and publication constantly churning out stories on ‘how to be better’ yet there’s a fine line between trying to improve yourself and doing too much. For example — Warren Buffet eats McDonald’s breakfast every day and loves Coke while Elon Musk gets minimal sleep, runs 3 companies, and is apparently an asshole yet both are wildly innovative (which == successful in my book). At the end of the day, my evolving philosophy is that yes, I want to be better. Yes, I want to sleep more, eat better, workout more, and have better relationships but at the same token, I still want to be a fucking human. I never want to be that dude who meal preps every single week, works out every single day, and orders vodka waters. Fuck that, I’m still human. Also, I’m writing this for me and by no means am trying to prescribe what I do to other people or say the way I think is right.
• Lastly, I’m SO lucky as fuck to have what I have (an awesome team, family, friends, girlfriend, etc) and wish I could be better at remembering just how lucky I am. Gratefulness is a learned skill, it can be easy to constantly think about your own problems, goals, etc but when you start thinking about other people and how lucky you are in certain situations — it puts life into perspective. Flights are big for me because it gives me a chance (especially when the WIFI is out) to just reflect and when I get a chance to do that like I did on my way to Italy, I can write so clearly and understand life so much more clearly.

Top Influences

• Elon Musk — not a ton of explanation needed but he’s the modern-day Iron Man who is controversial (which I like) yet is innovating on a level that’s unparalleled. He is working to save our planet with Tesla and Boring Company while working to find new planets with SpaceX. The dude is relentless
• Baker Mayfield — yes, I’m a Browns fan but I’ve wanted Browns to draft Baker ever since the last college season ended. After seeing Baker’s list he had on his locker last year which I referenced in my last year-end post, I instantly looked up to him. He is the epitome of a leader (in my opinion) and watching what he did this year on the field for the Brownies just made me look up to him even more. He’s great at his craft but he’s even better at energizing his teammates, leading the team, and setting them up for success.
• Lebron James — similar to Baker and Elon, just an absolute baller on a mission who leads teams and also brought Cleveland a ship which I’m still thankful for
• My uncle — I talk with my uncle nearly every day. Dude is absolute baller who is a top English professor at a school in Boston and we constantly exchange thoughts as we both battle challenges and work to BALL
• My mentors/investors — a few of them that are very close that I talk to nearly every other day continue to help me as I navigate through the startup waters

Favorites

• Music — I listen to so much damn music that it’s hard to even nail it down to favorites, especially when Spotify dishes me so many awesome songs and artists I’ve never even heard of. Here is my favorites playlist that I’m *currently* listening to as I write this and also my Year-End Review :

• Books — didn’t read nearly as much as I wanted but some favorites that come to mind are: the Elon Musk book, the Gucci Mane book, Richard Branson’s first book, and the Third Twin by Ken Follet
• Blog posts/articles — everything Andrew Chen wrote, everything First Round published, and lots of random shit on this site (Medium) but my favorite article of the year was “My Dad’s Friendship with Charles Barkley” which made me tear up

Things to look forward to in 2019

• The Browns 2019 season (joking but seriously)
• A fresh start — feel like 2018 was one of my most transformative years and I’m ready to ‘start anew’ and take a lot of my learnings and apply them to what I aim to do next year, cheesy I know and everyone aims to do this but fuck it, ready for a new year
• Growing as a leader as I focus more on managing when it comes to the team @ Rapchat (now that we have a legit sized team w/ballers at every position)
• Traveling more — going to Costa Rica and a few other new spots next year
• Learning new things — not sure what exactly these things are yet but I love learning and know that ‘things’ are going to pop up
• Working towards clarity in life (which obviously compasses everything)