2021 In Review

2021 In Review

Ryan Leary

I started 2021 with a general “resolution”: Don't be afraid to spend money on things, take more chances, expect to fail more as a result, and celebrate the learnings. It went pretty well, and I definitely had some FAILs.

📍 Living Situation

🏔 → 🏝 ALOHA Starting out with a big update - after 2 years in Tahoe, I’m now living in Hawaii! Yes, the skier has left the mountains...right as a record December snowfall hits, besting the December of 1970. The wildfire smoke was a big downer this summer, really limiting things, and then an opportunity to housesit in Maui popped up. 6 weeks there didn’t feel like enough, so I extended that to another 2 months in Honolulu, and then I found an apartment to return to following Thanksgiving. Not counting 6 months study abroad in Tokyo, I’ve lived in California since birth, entirely in the bay area.

I’ve got an incredible 2 bedroom in Honolulu - plenty of space for people to visit HINT HINT. I guess the snow follows me, my first weekend in Hawaii had a blizzard warning. There was a point in time this year where Hawaii had more snow than Colorado this year...

🏥 Health

😷 COVID The year started out slow. On my birthday end of 2020 I woke up with a sore throat, and after messages from the family wishing me a good day, they mentioned feeling bad flu symptoms. We were in for a ride with the rona. Thankfully we all had a pretty mild case. I took 2 weeks to recover/quarantine, had a friend bring me some magazines (AMERICAN FRONTIERSMAN brought laughs all year long), and we all seem to have made a full recovery.

🔔 TINNITUS A couple months later I woke up in the middle of the night with HORRID ringing in my ears and couldn’t sleep for a few days. Over the year it’s gone down, especially if I’m working out regularly. Perhaps Covid will leave me with an ever present reminder to lace up the shoes and go run.

🚵 MOUNTAIN BIKE CRASH They say it’s only a matter of time before an injury like this happens on the mtb. I knew it would happen at some point. This was probably the defining moment of 2021.

If you aren't falling you aren't going hard enough

On a rescue mission to save my brother from his injury on the Pacific Crest Trail and keep him company, I decided to take my mountain bike down to Mammoth and ride the trails.

The conversation went something like:

Keegan: Ya would be tight if you came down. Bring your bike, the MTB looks awesome, tons of people out
Keegan: I can’t walk anyways and will just be sitting in the hotel room.
Me: Ya that sounds hella fun.

The next morning:

Keegan: Be safe out there
Me: Ya. Just planning to ride cautiously. Nothing crazy. Don’t want to risk an injury, I have to take care of you.

A few hours later:

Me: Hey...think I need you to take me to the ER.

After a full day of riding VERY cautiously and about 50 yards from the end of the day, I went over the bars and crunched down on my right shoulder (audibly a very LOUD crunch). I popped up, gave myself a few minutes to ensure I wasn’t concussed, and was able to move. By the time I got down the road to the shuttle I couldn’t even push my bike. I got on the shuttle and asked Keegan to hobble down to meet me and when I arrived at the top of top shuttle stop it was pouring rain. Head down, full on raging thunderstorm, I pushed my bike to the car and got in soaking wet. Keegan called me, he’d found a overhang to hide under. We eventually met up and he was able to get my bike into the car. We returned to the hotel room so I could change clothes and get a look at my shoulder. As I’m changing my shirt

Keegan: It doesn’t look bad
Me: Really? it’s pretty sore, maybe I just hit it hard. moves arm a little, bone sticks up profusely
Keegan: OHHHH that’s BUSTED. We gotta get to the ER.

Mammoth ER was great, and I learned I had an AC separation grade 3. Strong AF bones, nothing broke, just ripped all the ligaments and whatever is in there that holds that bone in place. Most people just learn to live with it fine and a couple months later it doesn’t bother them seemed to be the advice. The nurse had done the same a few years before. The doctor as well. A followup visit in Truckee really steered me away from considering surgery - many people had worse issues as a result. They just haven’t figured this one out yet. Happy to report at the end of the year I’m basically back to full power, with a weird bone that sticks out, but pullups remain difficult and I’m not too eager to get on the mtb again.

We left the ER and I was high as a kite on percocet. Good times. Very good times. We found a tiki bar for dinner (the plan all day had been to go to happy hour) and I noticed a very old sign that said free mai tais for military (from memorial day, it was July 2nd now). Keegan got well taken care of and I had my pain killers - it was actually a damn good time! I think we were at CVS 5 times that day, might be a mammoth record.

🏕 Adventure

BACKCOUNTRY SKIING 2021 had some epic days at Squaw Palisades, Alpine, and Alta, but the real treat were some backcountry excursions. My feet gave out on me on Mt. Rose (bought custom liners, problem solved), we had an incredible pow day on Rubicon peak, a couple of trips up Tamarack, a great day on Silver, and many sunrise sessions at the properly named Sunrise Bowl. By the time I took my AIARE I was decently well versed in things, and shocked by how little others knew about skiing and backcountry in general. It was a good reminder of the initial goal of the year - get out of your comfort zone. These folks were better at it than me, and looked to me to guide them most of the weekend 😂 .

Making him work hard on the snowshoes
No more covid + insoles feel GOOD. Vibes on point.

🏔 MT. SHASTA Keegan and I made our great return to Mt. Shasta this year and conquered the peak. With low snow we had to take the Clear Creek route rather than the planned Avalanche Gulch. It was pretty cool - we were the only ones on the mountain except for CHP practicing some landing routines. I have a video planned for this one, for now you should check out Keegan’s which is scenic AF.

Highlights include:

  • Keegan being super fit and repeatedly putting his camera on the tripod to capture the whole climb and him asking me to pick it up when I was at my absolute lowest in exhaustion.
  • Seeing Starlink get deployed. At first it was one thick line as we fell asleep and the next morning a perfect line of 50 ants in the sky marching right over the peak at 3am.
  • All the Crystal shops in Shasta. And the purple vibes IG account to communicate with the Lemurians.
  • Black Bear Diner - the OG still is the best and it’s sad the other locations don’t live up to this amazing spot.
  • Having the mountain to ourselves. That was epic.
  • Glissading is still VERY fun.

🥾 BACKPACKING I hoped to do a lot of backpacking this summer and got out on a few nice trips before my shoulder got busted and the wildfires shut down the California forest most of the season. Those few trips were really great. I really enjoyed my solo off-trail expedition to a lake I’d wanted to get to for years and took hours of map hunting online to find. It was still frozen when I went, which left me a good reason to go back, and now I know where it is!

🏄🏼🤿 WATER SPORTS I picked up surfing during my stay in Waikiki. I’m still very much a beginner and really enjoy just being bad at something as the progression is so fast! In just a few 2 hours sessions on the water I’ve gotten so much better and look forward to getting better. We did some spearfishing and snorkeling on Maui - sea turtles are so magical watching them in the water.

🚁 DOORS OFF HELICOPTER The last day in Maui we booked a doors off heli tour of Maui. It was incredible and a few points where the wind picked up a bit nerve-wracking. I've always wanted to do this for a photo excursion, and timing was on our side - it had rained for days prior and the waterfalls were pumping.

I linked some videos on IG reels below as well. They are fun.


📷 PHOTOGRAPHY 2021 I got really motivated around photography and some video work. Partially spurred by a new mirrorless camera purchase (but lol Canon isn’t any smaller or lighter) and a few adventure shots. I invested this year in learning, finally signing up for a photography course from two photographers I’ve followed on IG for a long time. The biggest thing has been learning about selective editing. I’m not comfortable with the toolset yet, but getting more familiar about what other tools exist and how to use them. IG has my top pics. Here's a sample of my favorites:

🌐 rtleary.com came into existence this year. Inspired by Show Your Work I wanted to share more of the process behind what I was doing and learning. I also just liked Keegan’s website and wanted to copy him. I felt like this year we had a great brotherly bond motivating and pushing one another to do cool things.

🎥 VIDEO I made a few fun videos this year, some for youtube and some just for IG stories and reels. Reels are crazy, one got 12k views and my phone would buzz constantly with notifications when the algorithm picked it up. I think this year my videos really got higher quality, and I enjoyed the switch from Adobe Premiere Pro to DaVinci Resolve, especially when I got to play with effects in Fusion.

My favorites:

behind the scenes goofballs. pack your puffy for hawaii

👨‍🍳  COOKING Perfecting furikake seared ahi was a highlight this year. I was really excited to return to Nico’s and give the OG a try and think my home version may stand higher than theirs now! My margarita game is on point, and later in the year I really got into using the Ooni to make pizza, but have lots of work to do there still.

🤟🏼 Hobbies

🦍 APE INTO CRYPTO AND NFTS I’ve long been curious about crypto and got lucky with some BTC and ETH buys years ago. I never would have predicted the 1.4 ETH jpeg of a Bored Ape would take off like it did, and it fueled an utter fascination with the space. I figured the best way to learn was to get my hands dirty, and found an incredible community. I mean it when I say one of the most fun things I did this year was a reverse dutch auction for a NFT where my friend caught the lowest price in a 15s window after waiting 3 hours and then saw the price soar. The real joy here has been connecting with friends over it, sharing wins and losses or discussing chia plotting wins. We're all losing sleeping thinking about it and WAGMI.

🖥 BUILD A PC I've wanted to do this for years and finally built a PC, despite how the emoji looks. It's very fast, very powerful, and very RGB. I still prefer games on the xbox/tv, but this has been incredible for video and photo editing. I think it's the beginning of my transition away from Apple, who I find more annoying daily. It felt so good when it finally powered up after hours of troubleshooting (lazy wiring on my part).

A few of my favorites this year:


  • It Takes Two: Best coop I’ve played in years. Awkward playing a married couple with your best friend.
  • Halo Infinite: Classic arena shooter is back. Campaign is flawed but grapple is fun. I haven’t had dreams about a game in a while.
  • Hades: This has been out a while, but if you haven’t played it get it now.
  • Last of Us 1+2: The best game to play while home with Covid. What a rough story. Yikes.
  • Psychonauts 1+2: In prep for 2 I played 1. What a creative team.
  • Honorable mentions:
  • Resident Evil 8, Carrion, Twelve Minutes, Among Us, Splitgate, Death’s Door, Gears Tactics, Hitman 1,2,3.


  • Project Hail Mary by Andy Weir
  • The Devil’s Hand by Jack Carr, great series in general.
  • Boss Up by Rick Ross
  • Show your Work
  • Indistractible
  • Fixing Your Feet
  • This is your mind on plants


  • Tim Ferris with Naval + cdixon talking about crypto and web3. Great primer to learn.
  • Joe Rogan + Snoop Dogg
  • All in podcast - quickly becoming a favorite for all things tech


  • Dune
  • Story of Xbox, free on Youtube.
  • Squid Game: Korean keeps crushing it in this genre.
  • Roadrunner - Anthony Bourdain: Always searching for something...
  • Snowpiercer
  • Lupin
  • No Sudden Move: This one was ok, but as I read about it more after I found I enjoyed the film itself more. Funny how that works.
  • Anything Sea Shanties


🌳 ORG TREE The biggest challenge this year was growing and scaling the team, which went well. We  were able to bring in and grow new leads and identify a much better picture of where the team is going. There's ALWAYS more to do, but after a successful launch in a new product line and a smooth holidays for Quest, it's nice knowing the team's work behind the scenes drove some amazing results. I'm hopeful for a promotion following the achievements of this year, but not holding my breath. I'm pretty excited about work right now, we're positioned really well to achieve more, but in a very sustainable way.

🏠 REMOTE WORK Related to Hawaii...I was approved for remote work and will be working from home for the next year! This has me rather nervous, but was definitely one of those just take the chance and see what happens moments during the year.

My life upgraded with

  • Custom ski insoles - A shop in squaw valley was highly recommended when my feet were having issues in my backcountry ski boots. Put these in and problem fully solved. Skiing with them feels a little weird, but the comfort is worth it and I think I can adapt with some more downhill time. Invest in good gear, it's worth it and makes the trip much more enjoyable, especially with backcountry where 95% of it is hiking.
  • Burr grinder - A friend has pushed me to get one for years. Finally pulled the trigger and no looking back. Paired with a zojirushi, mornign coffee routine is quick and easy and very delicious.
  • Yoga - In maui my shoulder wasn't fully back in action so Keegan and I zenned out with lots of yoga. I felt fantastic and need to get this going regularly.
  • Theragun - maybe a gimmick, but it makes my legs feel much better after a long bike ride or ski day.
  • Dohm noise machine - catch that bit about constant ringing in my ears? It's still there, and this makes nights far more enjoyable.
She may love to roast me, but we're still friends.

2021 wouldn't have been great without such good friends and family to share the fun with or offering assistance when I was injured or down! Happy we're all healthy despite everything goin on! As you can see from the pictures, the best times were those shared. Or making fun of Keegan and his granny panties.