Matt Spitz

Now with more AI

Fri, 20 Mar 2026 00:00:00 -0700

Of course, you can’t spell Matt Spitz without AI.

I did some Cloudfront, Route 53, and ACM gymnastics, and now the default domain name for this website is mttsptz.ai. All of the links from mattspitz.me that my millions of followers have bookmarked still work – they’ll just redirect here.

Welcome to the new revolution, where domain names cost $80/year for a dad joke. It’s worth every penny.

Crosscountry bicycle trip

Tue, 08 Jul 2025 00:00:00 -0700

From April to June this year, I rode my bicycle across the United States, from Washington DC to the Oregon coast. The ride was solo and unsupported, meaning that I rode by myself and carried everything I needed on my bicycle. It was an incredible adventure and one I’ll never forget.

By the numbers:

4026 miles
127318’ elevation gain
11539’ above sea level at Hoosier Pass in Colorado
58 days
14 states
10 times crossing a Continental Divide
8 cousins
6 flat tires
5 bags on my bike + a tent + a sleeping bag
4 tires replaced
4 cleats replaced
3 snowstorms
2 chains replaced
2 towns I stayed in named Cambridge (Ohio, Idaho)

Along the journey, I took a photo with a playing card to mark each day, and I kept a travelogue via Google Doc to share updates with family and friends every so often.

Why spend two months riding a bicycle across the country? I’ve loved bicycle touring since my first bike tour in 2009 from the Bay Area to Los Angeles, and I’ve always wanted to go crosscountry. I’m between jobs, the kids are resilient, and I’m in the best shape of my life. My spouse was also very supportive, for which I am grateful!

Most of my preparation for the trip was the route and the packing list. I lost weight before going, but I otherwise didn’t do any particular physical training for the trip. I ride bikes regularly, but I’ve heard that most of the training one needs for a long bike tour comes in the first week on the road, and it turned out to be true!

The Adventure Cycling Association publishes bike-friendly routes around the United States, and I’ve had success with those in the past. The routes prefer bike paths, quiet county roads, state highways, and, where possible, gradual climbs and ample services. A popular route is the TransAmerica bike trail, but since I’d heard that the dogs are particularly fierce in Kentucky and Virginia, I avoided that stretch of the country entirely. Even so, I ran into dogs – more on that later.

My route started in Washington DC and followed the Chesapeake & Ohio Canal Trail and the Great Allegheny Passage Trail to Pittsburgh. From there, I followed the ACA’s Chicago to New York route to Indianapolis, then the ACA Eastern Express Connector to the TransAmerica Trail in Toronto, KS. Most people who travel across the country do so in the summertime and go from west to east. I was optimizing for missing the least amount of parenting, so I went while the kids were still in school and opted to go east to west to avoid snowstorms in the Rockies as much as possible. I still hit snowstorms – more on that later, too.

As for the packing list, I mapped out all the gear and bags I thought I might need a couple of months in advance and did some test rides to check the weight and see what might be missing or superfluous. I packed a variety of clothing for different types of weather, and a few times, I ended up wearing almost all of it at the same time. With the exception of a few items that I mailed home after the first two weeks, I thought my packing was a good balance of having the right amount of stuff for the truly wild variety of situations I’d encounter.

And that was pretty much it for planning. I had rough plans to meet folks on the way but otherwise didn’t plan any stops or lodging in advance. I couldn’t predict my pace, the weather, or how my body would hold up, and having concrete plans that I’d have to hit would have introduced unnecessary stress. For estimating when I might be able to meet folks along the way, I kept a tracker to track my per-day distance and predictions for when I might arrive at future waypoints. Cool guys make cool spreadsheets.

Neighbor L helped me disassemble my bike and put it in a box for the plane ride to DC, and off I went! P picked me up from the airport, and I stayed with A, K, and their kids. After a buffer day assembling the bike and a dinner with a lovely assortment of DC friends, I set off on the first week of the trip along the C&O Canal Trail and the Great Allegheny Passage.

This first leg was the only time I had folks riding with me until the very end – J rode the first day with me to Harper’s Ferry, and Cousins B and S joined me the three days to Pittsburgh. On the first day of the GAP, B, S, and I crossed the eastern Continental Divide!

Riding the C&O and the GAP was my first real experience on gravel, and it’s tough. Especially with the extra weight on the bike, my speed was discounted about 20% by the gravel and by another 20% when it rained an inch my second day and the gravel turned to mud. My cleats also clogged with gravel, which mangled the cleats and made it difficult to clip in. It was frustrating, to say the least! Fortunately, my bags are waterproof and I was able to put everything inside them.

The first couple of weeks of the trip served as both a physical and mental warmup for the rest of the journey. As predicted, my body got used to the rhythm of riding 5-8 hours a day with 40 lbs of stuff on the bike. I also got into the daily routine of checking the weather forecast, packing the bags, navigating, figuring out where to eat and sleep, arriving, unpacking, going to sleep, and doing it all over again! Mentally, I had to get used to the fact that I was leaving my family for a long time and give myself permission to do the trip – it was easy to feel guilty for taking a necessary rest because I felt like I wasn’t making progress to get home as soon as possible.

I made a couple of conscious mindset shifts, too. On previous tours, I’ve learned that when riding for multiple days, there’s literally nothing to do all day but get to where you’re going by sundown – it’s a marathon, not a sprint. So, I made sure I left early enough and took as many breaks as I needed. A new mindset shift for this trip was being explicit about my priorities. My goal was to make it to the beach on my own power in one piece, not to follow the route I’d planned or complete every trail. I gave myself permission to get off the C&O Canal Trail (and later, the Katy Trail in Missouri) to avoid muddy gravel. Orienting myself around the purpose provided some clarity when I had to make some tougher planning decisions.

My planning was done 12 to 48 hours in advance. Every evening, I’d look at the weather forecast and the upcoming towns on the route and plan 2-3 options for food and lodging. By each day’s lunch, I usually knew where I’d stay that night. There was a fair amount of rain, especially in April, but the wind was the real killer. A substantial headwind makes for a rough day, and a tailwind can add 20-30% extra distance for minimal extra effort. Two-star motel options are plentiful in the eastern United States, and same-day booking made the rates relatively affordable, too.

Out of Pittsburgh, I rode up into the Western Appalachians into West Virginia and Ohio. This was my first taste of climbing, cows, and yards with many, many cars.

I stayed with C’s family in Columbus, and she and her fiancé flew out for the weekend! The first day where I really felt warmed up was from Columbus to Dayton – I left after Easter lunch and still made it over 80 miles before sundown. On a rainy morning the next day, I took my first side quest to the incredible National Museum of the US Air Force.

Leaving Ohio, the roads got flatter, and I picked up the pace – through Indiana and Illinois, I did 300 miles over three days. In the Bay Area, I’m used to riding shorter distances with a lot of elevation gain, not 100+ miles on flat roads, and certainly not with full bags on my bike. LET’S GO, BABY!

Cousin R came to meet me in Indianapolis, and downtown Indy was a trip. In one 15-minute walk, I saw folks dressed up to go to a Pacers playoff game, a hollowed-out mall with only a couple of remaining storefronts, Christian conference attendees with lanyards, and a plaza with folks laying on the ground and/or yelling at one another. My route out of town followed a bike path with tents and downed trees. For all the flak San Francisco gets, it turns out that fentanyl and recovering post-COVID is a real problem for other American cities, too.

Missouri presented some real challenges. My route mostly followed the Katy Trail, and the rain and muddy gravel made for some difficult riding. At one point, I departed early and left the trail to try to avoid a rainstorm. My new route took me on back roads with a few scary encounters with aggressive dogs, and I had to shelter in a Subway for a couple of hours until the thunder and lightning subsided.

Despite the tough conditions, I was buoyed by visits with my parents’ cousins L, B, H, M, D, and V! In Hermann, MO, a bar was my only chance for food on a Sunday night, and although the kitchen was closed, I made new friends through karaoke.

When I shared my route, several people warned me about Kansas – it’s boring, you’ll get in your own head, there’s always a headwind, etc. They were right! Kansas has about one day’s worth of scenery for a week’s worth of riding. I got cropdusted once, and the turtles kept the road interesting. Fortunately, my stay in Kansas didn’t last long – getting out of the gravel and mud meant that I could pick up my pace again, and I FLEW on the flat roads. I averaged about 100 miles a day that week.

I took a particularly memorable side quest in Kansas to visit the area where my grandfather grew up on a farm. I rented a car and poked around where he would have lived and gone to church and school, none of which exists in the same way as it did when he was there. I met the man who was the pastor of the church after my grandfather’s family had left when I found an unlocked door at the church and introduced myself to his wife. She invited me over to their house for a visit that afternoon, and I realized that the pastor and I had three connections: he was the pastor at the church where my maternal grandfather had gone, he took classes from my paternal great-grandfather in seminary, and he was the brother of one of the deacons of our church when we lived in Brooklyn. Wild!

Leaving Kansas marked the halfway point and a significant change in the trip. In the east, my route was mostly flat and followed the interstates, which meant that there were plenty of services and 2-star motels along the way. The west was much less predictable and required some planning creativity. I camped, carried more food for meals, and frequently did long stretches with no services in between. I got to use all the physical and logistical muscles I’d developed during the first half of the journey.

In Colorado, I had dinner with my mother’s cousin R and her daughter K before setting off for the highest peak on the route – Hoosier Pass, my first crossing of the western Continental Divide. Over the course of a day and a half, I climbed from 4700’ above sea level to 11539’ at the pass. On the way, I had lunch with S and L in Alma, the highest incorporated town in North America.

The beautiful views in Colorado more than made up for the challenge, though! Afterward, I did a shorter ride to Hot Sulphur Springs, which featured, you guessed it, hot sulphur springs.

Wyoming presented some of the most beautiful terrain and challenging riding. I camped for the first time along the Wyoming/Colorado border and woke up covered in frost! Between Rawlins and Jeffrey City, I had the pleasure of riding against 25mph headwinds. The state highway I rode on had a wide shoulder, and every time a truck passed, I’d get caught in the slipstream, pulled forward a bit while it was next to me, and then blown backward once it passed. When a truck passed on the other side of the road, I’d get blown backward for a second and then pulled forward. It was harrowing, I yelled a lot into the wind, and no one heard me.

When I arrived in Jeffrey City, I stayed in a church that opens its basement to cyclists and enjoyed eating an enormous “steak sandwich” at the only restaurant in town.

Lander, WY was surprisingly hip. It’s home to the National Outdoor Leadership School and some killer rock climbing nearby, attracting young outdoorsy folks and some cool restaurants and breweries.

I crossed the western Continental Divide for the fifth time at Togwotee Pass and encountered my first snowstorm. It had been near-freezing at various points on the trip, and I’d encountered rain, but never both at the same time. I guess that’s what I should have expected at 9000+’. The snow turned into cold rain on the way down to Grand Tetons National Park, and the park ranger at the gate convinced me to buy some bear spray. I didn’t end up using it with bears, but I wish I’d had it for the dogs in Missouri!

The next day, I left the bags in my room and cruised unencumbered down to Jenny Lake. I got back in time for checkout, picked up my bags, and rode into Yellowstone.

There was snow on the ground but fortunately not in the sky, and I crossed the Continental Divide three more times as I enjoyed the scenery and rolled into the Old Faithful Inn.

I wandered the geyser basin early the next morning and made a new friend, P. There were many fewer people than I’d expected in the park, which was somewhat understandable given the snow and a blessing to me as a cyclist on the road in a popular national park.

On the way out of Yellowstone, I got caught in my second snowstorm with a healthy helping of hail, and while I’d planned to go further that day, I called it quits in West Yellowstone. SNOW THANK YOU.

Montana offered more beautiful countryside and rolling hills, though I noticed a distinct shift in Montanans’ view toward outsiders than I’d experienced previously. When introducing myself as being from California, I heard several times, “ugh, I’m sorry.” When I pressed, I realized that the sentiment was a mix of the unfair perception that San Francisco is a rotting urban center in the media and the fact that many Californians have moved to Montana and jacked up the cost of living. One couple articulated to me that they’re fine with Californians moving to Montana and integrating with the community without trying to change it with fancy coffeeshops and enormous mansions. I get it!

I got caught in my third and by far the worst snowstorm in Montana, too. The route that day featured a couple of large climbs with no towns along the way, and as I crested the first hill, the sky turned black. With nowhere to go but forward, I started the second climb with snow dumping in my face.

I flipped on some pump-up music, and after an hour at 5mph, I made it to the top, shivering and teeth chattering. Ten miles down the hill, I stayed at Jackson Hot Springs and took a welcome dip in a warm pool.

After my ninth and final crossing of the western Continental Divide and a stop in Missoula, a cool college town, I met Cousin C at a hot springs near the Idaho border for a lovely evening with him and his pup.

The climbing and scenery continued in Idaho as I rolled along. The trees and rivers were starting to remind me of the Sierra Nevadas – I was getting closer to home!

As I descended back to ~4000’ above sea level, the days started getting hotter again. I crossed into Oregon along the Snake River on a 100-degree day. Yikes! The few unpleasant hot days I experienced and the heat waves that the country has experienced since made me glad to have done this trip in the spring rather than the summer. While riding in the snow is decidedly unpleasant, I’d rather be cold than warm and dehydrated, and for the most part, I didn’t have to deal with any bugs!

During the last week in Oregon, I could sense the finish line getting closer, but I still had a lot of work to do. Oregon, as it turned out, offered the most elevation gain per mile of any state on my trip!

I’d planned to meet up with D in Sisters, OR for the last few days of the ride, so I had a little extra time to explore before our planned meeting time. I poked around the John Day Fossil Beds and left my bags at another church-cycling-hostel in Mitchell to visit the Painted Hills. Great side quests!

Sisters, just north of Bend, is so named for three beautiful volcanoes in the Cascade Range that loomed in the background as I approached.

AMERICA!

There, I joined up with D and his family to ride the last few days down to the Oregon coast. As we approached sea level, the riding got easier until we arrived in Florence.

The last five miles to the beach were along Highway 1 with brutal headwinds and sand, and as I dragged my bike out to the beach, the bags acted like a sail and blew the bike around. Nothing is easy, kids. But hey, I made it!

I rode with D’s family in their car up to Portland, where we all stayed with Z and L. I took a buffer day to sort out my stuff and pack my bike. The next morning, I flew back home and found two welcome-home banners!

Gear

I used the tech I brought on this trip every day, and it proved invaluable to a safe and well-routed journey.

My bike computer is a Wahoo Bolt v2, and I used it for routing and tracking my ride day-to-day. Each morning, I’d load up the day’s route and follow the directions on the map – some folks do this with their phone but I prefer fewer distractions on the road. Each evening, I would sync my ride to Strava and get statistics like distance, elevation gain, etc. On the second day of the trip, probably in the rain on the C&O Trail, the thermistor and barometer stopped working, so my temperature and elevation estimates were off while I was riding, but the latter was easy enough to fix in Strava after uploading them.

I used a Garmin RTL515 tail light, and it was a game changer. It’s a tail light with a radar built into it, and every time a car would approach from behind, I got an alert and a chirp on my bike computer. When a car was approaching above a certain speed, the chirp was much louder. The scariest thing about riding on highways is when a car passes quickly without giving extra space to a cyclist in the shoulder (getting “buzzed”). With the radar, I had a warning that a car was coming so I could check my rear view mirror, assess whether they would give me extra space, and move further into the shoulder if necessary. Worst case, I wouldn’t be surprised if a car did buzz me. The radar also gave me the relative position of cars coming up behind me, so I knew without looking back whether it might be safe to change lanes – of course, if the radar were clear, I’d still check over my shoulder!

My kids packed me companions for the road. I had a tiny model Ewok named Cherry Nose ziptied to my handlebar like a prow maiden and a bracelet that I wore throughout the trip. These are well-traveled keepsakes, and I’m glad they survived the journey!

I did some souvenir shopping to mail home to my family, and for myself, I collected at least one sticker from each state. When I finished, both of my bags were covered, one with stickers from the east and one with stickers from the west.

Mechanical adventures

For the most part, my bike held up well, though I wish that I’d switched to tubeless tires or at least put on more durable tires before I started. I underestimated how quickly tires wear under load, varied road conditions, and lots of climbing. I didn’t have confidence in my tires for much of the trip, and it didn’t feel great. About a third of the way through, I switched from 37mm tires to 40mm tires, and that felt better. Fortunately, I got a lot of practice fixing flats in a variety of weather and road conditions, and I was never close to running out of tubes.

I had zero issues with the drivetrain on the road. At each bike shop I passed, I asked them to check the chain and ended up getting it replaced twice.

I also should have switched my cleat system before I left. SPD-SL cleats have their advantages, but they’re not meant for as much walking around, especially in dirt and gravel. They got mangled quickly and when they got muddy, it became difficult to clip in.

Listening

Along the way, I listened to a lot of audiobooks, podcasts, and music along the way with an earbud in my right ear so I could hear the road. Where possible, I tried to listen to books about the part of the country I was riding through, including Demon Copperhead (opiod crisis in the Appalachians), The Worst Hard Time (dust bowl in Kansas), and several books about Lewis and Clark as I followed their trail through Montana, Idaho, and parts of Oregon.

Music-wise, I ended up sticking to my favorites rather than branching out, and STP’s Core and Alice in Chains’ Dirt got me through some miserable climbs. I also listened to the Pearl Jam studio catalog in reverse chronological order and discovered some gems that I hadn’t heard in a long time.

Lodging

I sampled a great variety of lodging options on the trip. For the most part, I stayed in 2-star motels. They had the right balance of warm showers and fresh linens, availability of guest laundry services when I needed them, and affordability, even if I got sick of eating powdered eggs every morning I stayed there. Friends and family in Ohio and Missouri hosted me, and I’m grateful to B and J and L and B for opening their homes!

I stayed in a few Airbnbs, which had the added benefit of being able to cook a fresh meal for myself. One of those Airbnbs was a tiny cabin outside of Mitchell, OR that had an outdoor shower, an outhouse, and a grill.

On the first night of the tour in Harper’s Ferry, J and I stayed in a Potomac Appalachian Trail Club “cabin”, one of the ~50 cabins the group maintains for folks hiking the AT. J had to get a $40 membership, and we stayed in a four-bedroom house with a fabulous view for $100/night. Wow!

I camped only a few times – it was too cold and rainy for most of my trip, and I was fortunate to have the option to stay in a motel instead. When I did camp, the stars were beautiful and the mornings were chilly.

The most memorable places to stay were the church hostels. In Jeffrey City, WY and Dayville, OR, the churches open their parish halls to cyclists. They have kitchens and cooking utensils, and in Dayville, a pantry full of dry goods available. They ask that you sign the guest book and clean up after yourself. In both places, I stayed alone, but I imagine that it would have been a good opportunity to meet fellow cyclists. Actions speak much louder than words, and these churches’ kindness to travelers is a strong demonstration of God’s love!

Food

Food is my favorite subject, and burning as many calories as I did, I ate a lot of it. As much as I could, I tried to eat healthy (high protein, fruits and vegetables), but it wasn’t easy. I became well acquainted with gas station cuisine, usually for protein shakes and snacks but sometimes full meals when there weren’t other options or I arrived too late – seriously, what dinner restaurant closes at 7pm?

America is a place with varied cultures and interests, but one thing we are united on is how much we love pizza and cheeseburgers – like The Beatles or Christmas music, I avoided them as much as I could and still got about as much as I wanted. The Mexican food was surprisingly excellent and not horribly unhealthy, and going to those restaurants was a chance to practice my Spanish!

When camping or riding through places where I wasn’t guaranteed to be able to get food, I packed individual peanut butter servings, tuna, and bread. It wasn’t my favorite meal, but it certainly did the trick! Once, when camping, I found a Chinese restaurant and chowed down on chow mein with a side of bagged salad for the semblance of anything healthy.

Some of the best meals I had were grocery-store purchases cooked in an Airbnb. I often bought enough food to make dinner, breakfast, and sandwiches the next day. I could feel the difference when my body burned cleaner fuel vs. gas station garbage.

One of those Airbnbs included a basket of snacks, and I don’t think the host expected me to eat all of them.

Riding solo

My journey may have been on my own, but I felt very supported along the way. I saw a lot of friends and family on the way, and I was fortunate to have folks willing to cycle with me for 7 of the 54 riding days!

I called my family almost every day and sent them postcards whenever I had the opportunity.

The kids tracked my progress with a magnet along a large map of the United States, learning about the country’s geography at the same time that I did!

Finally, I kept a travelogue, a running Google Doc with updates, reflections, and photos every few days. I had more than 120 people following and cheering me on! I’m glad I spent so much time documenting my thoughts along the way. As soon as I wrote each update, I went right back to planning for shelter and sustenance, and I wouldn’t have remembered much without the notes to jog my memory.

As supported as I felt, I was still very glad to see my family, and they were happy to have me back!

Wrap

Some folks asked whether I had any major breakthroughs of thought or personal revelations on this trip, and I think the biggest epiphany was giving myself permission not to have one. The added pressure of discovering myself in addition to figuring out how to feed and shelter myself each day, often on the fly, is not what I needed. I’m still digesting this journey, and there is plenty of time for self-discovery now that I’m home.

One of my favorite parts of experiencing America at 12mph was the people I met along the way. As an extrovert on a solo trip, I had no problems striking up conversations with random strangers, and they all turned out to be positive experiences. I learned about life in places I didn’t know existed, and I made some new friends along the way. I’d also like to think that I served as a good ambassador for California, hopefully changing some minds about the people who live in San Francisco. I felt the kindness of strangers, too. More than once, I left a restaurant to find that my bill had been paid by the folks I was talking to, and a nice man stopped while I was pulled over in Idaho, offering me a cold energy drink and a nice conversation.

As I reflect on the trip, I’ve been thinking about the mental muscles I had the chance to flex on the journey. Resilience – being able to endure circumstances that are difficult to change – was previously a strong muscle, and I had plenty of opportunities to develop it further. I rerouted on the fly to avoid mud, figured out how to feed and shelter myself when options were scarce, and I powered through crazy headwinds and miserable weather from time to time. One thing I was particularly looking forward to on the trip was to have more opportunities for whimsy – getting pulled in a direction that wasn’t what I’d originally planned – since I know that I can be better at inviting or incorporating alternatives. In my vision for the trip, I’d meet cyclists along the way that would encourage me to do fun side quests, go on adventures I otherwise wouldn’t have, or otherwise change my journey for the better. But, while I met folks and asked for suggestions along the way, I didn’t run into anyone (literally, anyone) cycling the same direction, so I didn’t have that many new ideas to incorporate. Alas!

My greatest gratitude goes to my spouse and kids for their resilience and my parents for their support while I was gone for two months. I do a lot around the house, and I left a lot of slack to pick up. I’m glad that I had the chance to make this journey, and I’ll remember these stories forever. Truly, it’s a once in a lifetime opportunity, and hey! I did it!

Upon returning to San Francisco, I reassembled my bike and started riding again, this time crushing personal records on my favorite local rides. It’s amazing how fast one can go with fresh legs and without 40 lbs of stuff on the bike! I also bought a cargo e-bike. I’ve been e-bike curious for a while and I realized that I clearly like cycling, we often have a need for a second car, the kids are only getting heavier, and e-bikes retain their value quite well on the secondary market.

We enjoy riding bikes as a family from time to time, and maybe my family would join me on a future bike tour! Maybe.

Appendix

Route

Packing list

On the bike

Safety vest (safety first!)
Helmet
Biking gloves
Shoes with cleats
Transition sunglasses
2 water bottles
Wahoo Bolt v2 bike computer
Front light
Garmin Varia RTL515 radar tail light
Microfiber towel
Bandana
Lock & cable
2 sets of socks
2 bike bibs (Ornot)
1 long-sleeve jersey
2 short-sleeve jerseys
2 sweat bands
Lightweight rain jacket
Lightweight fleece
Lightweight fleece gloves

Notes: 2 water bottles was perfect, and both fit on the bike. I bought a new disposable water bottle every few days depending on how much water I needed for a given segment.

Off the bike

Sunglasses
Chacos
Compression socks
2 camping underwear
1 camping/zipoff pants
1 camping button-down shirt
1 long-sleeved running shirt
1 lightweight running shorts
Compressible down jacket
Swimsuit
Baseball hat
Beanie

Notes: Didn’t end up using the compression socks as much as I thought I would. Beanie felt superfluous at times, but when I needed it, boy I needed it. Sent the running shorts home when I realized I could do laundry in my swimsuit.

Camping

Ultralight 1-person tent
Tent footprint
Inflatable sleeping pad
Down sleeping bag
Ratchet strap for sleeping bag / rack

Notes: Ratchet straps turned out to be unnecessary when I realized I could attach the pannier straps to the sleeping bag, but they might have been helpful in if I’d needed to hitchhike out of a sticky situation.

Repair

Grocery bags
Garbage bags
Ziplock bags
Zipties
Small duct tape roll
Extra ratchet strap
3 tire levers
2 spare tubes
2 patch kits
Topeak rechargeable air pump
Presta/schrader valve conversion (for gas station air pumps)
Extra cleat bolts
Multi-tool
Screwdriver
Chain lube
2 bike lock keys

Notes: Should have packed extra cleats since SPD-SLs were so poorly suited for the type of travel I was doing. Duct tape roll was very helpful!

Food

Protein powder packets
Emergen-C packets
Honey Stingers
Energy bars

Notes: All of this was unnecessary. Food was readily available everywhere and I only ended up carrying enough for the next couple of days.

Tech

Headphones
Kindle
Bluetooth keyboard
10000mAh battery pack
USB wall charger (2 USB-C, 2 USB-A)
2 microUSB cables (camera, Kindle, tail light)
USB-C (phone, battery, bike computer)
1 USB-C-to-C cable
1 USB-A-to-C cable
1 watch charging cable

Notes: Propping up my phone against a wall or a glass while typing on the Bluetooth keyboard was a great and lightweight solution. My thumbs and eyes were grateful. Also, having a charger with multiple USB ports was key to charge everything at once.

Toiletries

Medical kit
Toothbrush
Toothpaste
Floss
Deodorant
Retainer
Chapstick
Comb
Razor
Shaving cream
Nail clippers
Nail file
Ibuprofen
Antihistamine spray (just in case)
Sunscreen
Bug spray
Hand sanitizer
Dish soap (for washing clothes)
Gold Bond powder
Chamois butt’r

Notes: Sent the hand sanitizer and dish soap home. Didn’t end up using the bug spray or the antihistamine spray, but I’m glad I had them. Yes, I still wear the same retainer from when I was sixteen.

Misc

Playing cards to mark days
Packing cubes (to compress all this crap down)
Pen
Postcard stamps
Traveling companions (1 from each kid)

Crescent City to San Francisco

Sun, 20 Oct 2024 00:00:00 -0700

Earlier this month, I rode from Crescent City to San Francisco. Together with my 2009 ride from San Francisco to Los Angeles, I’ve now cycled almost the entire California coast.

S is also a recently-unemployed engineering executive and was surprisingly game for this whimsical journey considering that he didn’t own a road bike until July. S is familiar with endurance training (marathons, backcountry skiing, etc), and the only thing you have to do when bike touring is get to the next place by sundown… We did a few training rides over the summer to warm up and it all went well!

My other companions on the trip were Boba Fett and the Yellow Submarine, handpicked by L and F and ziptied to my bike rack.

The four of us followed the Adventure Cycling Association’s Pacific Coast route and broke it up, attempting to balance bigger days with recovery.

	Distance (miles)	Elevation gain (feet)
Day 1: Crescent City → Orick	38.5	2697
Day 2: Orick → Scotia	83.2	3356
Day 3: Scotia → Garberville	48.0	1877
Day 4: Garberville → Fort Bragg	67.6	5230
Day 5: Fort Bragg → Gualala	63.6	4462
Day 6: Gualala → Inverness	86.0	6273
Day 7: Inverness → San Francisco	51.5	2385
Total	438.4	26280

Day 0: OAK → Crescent City

To get to Crescent City, we did a one-way pickup rental from OAK (“San Francisco Bay Oakland Airport” smh) to Crescent City. Driving into SF during rush hour was a nice reminder why I refuse to commute by car, and it wasn’t clear that my plan to bungee-cord the bikes to the bed draped over cardboard that I’d saved over the last few weeks would work, but hey, it did!

The drive was uneventful, and we got to scope out US-101 on the way up. Our cab driver from the airport told us about her ten children and how she was pregnant with her youngest at the same time that two of her daughters were pregnant(!), and this was but a foretaste of the delightful people we’d meet on this trip.

Day 1: Crescent City → Orick

38.5 miles, 2697’ elevation gain

We’re off! Aside from the two relatively large climbs out of Crescent City, this was a warmup day. We caught some beautiful views along the coast, and the Newton B. Drury scenic byway off US-101 offered less traffic and a chance to see some big trees. Of course, we also had to stop in Klamath for the Trees of Mystery and the enormous statues of Paul Bunyan and the Blue Ox, which I’d seen previously on my road trip with cousin in 2009.

We arrived in Orick around 2pm, our most downtime of the trip. The only places with food were a snack stand and the grocery store – it’s nice when the choices are easy. At the snack stand, while we waited for our burgers, Jim told us, “sit right here and tell me a story.” We ended up chatting with Jim (Orick resident since the 1940s) and a couple other locals for almost an hour. They were surprised that we hadn’t seen any elk yet, and then we talked about how much the elk are annoying pests. It was delightful.

We roasted hot dogs at the fire pit at our hotel for dinner, and I wish we’d gone for “all beef” rather than “first ingredient: mechanically separated chicken”. Oops. At the fire pit, we met a cute couple of older guys from DC that were traveling down the coast to San Francisco.

After eating a burger on the drive up and again for lunch, I learned that burgers on this trip would be like Christmas music – if I avoid them as much as I can, I get about as many as I want.

Day 2: Orick → Scotia

83.2 miles, 3356’ elevation gain

This was our first big day. We headed out to the coast and caught some elk on the way out of town (whew!) and dropped onto scenic Patrick’s Point Drive for some stellar views and a bit of gravel. We stopped in tiny Trinidad for breakfast and had one of the best meals of the trip (and the best coffee, according to S). We also saw our firepit friends from the night before! They have good taste.

Rolling into Arcata, we saw a festival in the park with a lot of noodle dancing and met a fellow bike tourist who was riding from Vancouver to SF and seemed a little… off. More on that later.

We rode through Eureka along the waterfront, which was both beautiful – the weather was spectacular – and sad with the number of tents we saw. From afar, we saw the Carson Mansion, an enormous Queen Anne Victorian featured on the bike map. Alas, they don’t do tours.

Lookit that huge Victorian!

Out of Eureka, we followed some frontage roads as we got into farmland, and out of nowhere, our Vancouver friend reappeared behind us and asked if he could stay with us that night. I politely told him no. It was eerie how quickly he’d appeared – either he was 5 minutes behind us for dozens of miles, or he was waiting for us at the bridge he knew we’d have to cross.

Anyway, we stopped in Ferndale for a pizza dinner before doing the last 10 miles to our hotel. The pizza was fine on a regular day and the best thing we’d ever eaten that day. Ferndale was also notable for being the most purple town – we’d been counting the number of Trump and Harris signs we’d seen along the way, and Ferndale had both the most signs by volume as well as a pretty even distribution. Also, apparently, Guy Fieri grew up there.

We rolled into the Scotia Lodge just as the sun was starting to set.

Day 3: Scotia → Garberville

48 miles, 1877’ elevation gain

This day doubled as recovery and sightseeing. We went through the Avenue of the Giants, a 31-mile scenic byway off US-101. Normally, this would be pretty crowded with tourists, but by design, we were in the offseason, and saw few. We packed sandwiches from the Scotia market for lunch and the lady upsold me “the best beef jerky she’d ever had”. While I agree that it might have been the best jerky she’d ever had, it was not the best beef jerky I’d ever had.

Anyway, the Avenue of the Giants was absolutely incredible. Riding through the trees while the sun peeked out and popping into redwood groves was an absolute delight.

We even biked through a tree, which was every bit the tourist trap and delight that you might expect it to be.

California was experiencing a heat wave during the first part of our trip, and for us, this mostly meant no fog along the coast, but we were inland on Day 3, so the 100° heat caught up to us after lunch. A smoothie in Miranda helped, but the real solve was a cold beer in Garberville after we arrived. Our hotel was the worst of the trip, but it was right across from a bar with a great patio and shared a parking lot with a delicious Mexican restaurant. We adapted a saying from one of S’s skiing friends: bike all day, party all night, in bed by 9pm.

AND, about 10 minutes after we arrived in Garberville, I saw our Vancouver shadow pass by on the road. Creepy.

Day 4: Garberville → Fort Bragg

67.6 miles, 5230’ elevation gain

This was the day that we were most worried about. We’d heard about scary truck traffic on US-101 before breaking off to follow US-1 to the coast, and this day had the biggest climb of the trip. We psyched ourselves up and got an early start, but it turned out just fine and much easier than anticipated! The traffic was minimal, and we’re in pretty good shape, so the climb was a nothingburger.

We rolled through the redwoods on a few nice descents before popping out at the coastline for our first taste of riding along the water under beautiful blue skies. The sea breeze was a welcome change from the previous day’s heat, too.

We ran into some construction and smaller shoulders than anticipated, but the last leg into Fort Bragg was along Ten Mile Beach along a dedicated bike path that led right to our hotel on the beach. We walked into town and ate everything on the (food) menu at the North Coast Brewery.

Day 5: Fort Bragg → Gualala

63.6 miles, 4462’ elevation gain

We woke at sunrise to the sound of the ocean, grabbed coffee in the lobby, and warmed up at the firepits outside our hotel. It was really nice.

Little did we know that we’d find the most climbing on our trip not in the redwoods up north but along the coast, constantly bopping between 0’-300’ above sea level. Google Maps’ elevation estimates for US-1 along the coast were off by almost a factor of two – we were fine, but it ended up being much more tiring than expected!

On a whim, we took a detour to the Point Cabrillo Lighthouse and had an extended breakfast in Mendocino, unaware of the endless climbing in our future.

Still, it’s hard to complain. The shimmering ocean, the crashing waves against the rocks, and the cloudless sky were incredible company as we dipped down to beaches and bridges over rivers and then up again into the bluffs.

At last, we arrived in Gualala, a town with zero cell phone reception and a Mexican restaurant that turned out not to be a Mexican restaurant. The salmon and chips were fabulous, and we strolled into the bar, which was tiny and the only one in town, as far as I could tell. We made friends with two guys playing pool – Brian and a man who called himself Gato. They had an interesting relationship based on threatening each other with violence after every shot, but they seemed to be friends. They were nice enough to us, anyway. Scotty the bartender said that the only times in his life that he cried was when his dog died and when the A’s announced that they were leaving Oakland, but he hopes to get a bartending gig in Vegas if they ever end up there. I love it.

Day 6: Gualala → Inverness

86.0 miles, 6273’ elevation gain

We had a mission, and that mission was to get to Tomales Bay before the oyster bars closed at 4pm. We had 70+ miles in front of us and likely more than the 3800’ of elevation gain that Google Maps told us (spoiler: way more). We’d gotten the worst sleep of our trip – the hotel room smelled a little dank and moldy, and I’m sure that playing pool at the bar didn’t help.

We woke in the dark and went to the only place that was open, a delightful spot with great SEO called “Bakery Pizza Mexican Food”. Their breakfast tacos are outstanding.

This was also our first day with some fog along the coast, and it was a nice contrast to the clear skies we’d seen thus far on the trip. Like the day before but longer, we went up and down and up and down and up and down along the coast. We visited three counties (Mendocino, Sonoma, Marin) and had a killer crab melt in Bodega Bay.

We made it to Tomales Bay at 3:15pm, very much in time for oysters, only to find out the Marshall Store had SOLD OUT OF OYSTERS FOR THE DAY and that Tomales Bay Oyster Company DIDN’T SHUCK AND SERVE OYSTERS FOR CONSUMPTION (admittedly, this would have been easy to research in advance). Our oyster plans were foiled!

Instead, we enjoyed grocery store soft serve in Point Reyes Station (they use buffalo milk!), and burritos in Inverness Park. The other thing we were looking forward to, the only hot tub of our journey, did not disappoint.

By this point, we ended our count of Harris-Walz and Trump-Vance signs, assuming that the Bay Area would be lopsided (spoiler: it was), and the final count was Harris-Walz 17, Trump-Vance 14. I’d have expected both more signs overall and more Trump-Vance signs, but I guess that most of the rural towns we passed through either had not enough traffic to merit trying to convince anyone or had similar-enough beliefs that putting up a sign was redundant.

Day 7: Inverness → San Francisco

51.5 miles, 2385’ elevation gain

This day was designed as a victory lap with minimal climbing as we covered familiar ground in Marin County. We didn’t feel particularly fresh, and S had some tightness in his IT band on the ride that he had to work through. It was nothing that ibuprofen, caffeine, and sugar couldn’t fix. Were we riding longer, this might have been a good day for a break (and laundry, yeesh).

We slogged our way through Marin and arrived at the Golden Gate Bridge just in time for the Blue Angels flyover that had been scheduled to herald our return to San Francisco. So nice of them!

After one last big, familiar climb up to the base of Twin Peaks and down O’Shaughnessy, we arrived!

For the most part, everything went as planned, and we didn’t run into any scenarios that were particularly scary or stressful. This was my second bike touring adventure, and I hope there are more in my future! S was an excellent companion and a good sport to ride almost 440 miles for the sake of some wordplay.

Notes

These are mostly for myself, but read on if you’re interested! Honestly, I can’t believe you’ve made it this far…

Preparation

For route planning, I bought the ACA paper maps and made table of the major places we might stay with approximate distance and elevation gain between them. We then crafted a series of days of the appropriate length, balancing big days with recovery days. I purchased the ACA GPX file for the route the week of, and in retrospect, that would have been much more accurate to plan the distance and elevation gain along the route we’d planned to take (using Caltopo or something like that). Google Maps wouldn’t always route me between places via biking directions, it often wouldn’t use the ACA route, and even when it did route well, the elevation estimates along the coast were wayyyyyy off. 😂

Packing list:

The map!
Everyday biking stuff: gloves, shoes + cleats, helmet, transition sunglasses, 2 water bottles, bike computer, lights
2 biking kits (bib + jersey)
3 sets of biking socks
Reflective safety vest
Microfiber towel for sweat during the day
Repair: tire levers, multitool, 3 spare tubes, hand pump, compressed air pump + 3 canisters, dry chain lube, 2 spare cleats
Off-the-bike: shirt, zip-off pants, underwear, warm windbreaker, baseball cap
Rain jacket
Swimsuit
Flip flops
Camera
Toiletries, sunscreen, chamois butter
USB cables, battery pack
Kindle
12 energy bars, 2 packs of Honey Stingers, 10oz bag of beef jerky
Lock with cable
Bungee cords for the pickup bed
3 grocery bags, 5 sandwich bags, 6 zipties
Boba Fett + Yellow Submarine

Notes:

I used everything I brought, and I’m glad I had the stuff I didn’t use: lock + cable, all the repair stuff.
I brought too many energy bars. There were plenty of places to stop for snacks and meals.
It wasn’t necessary, but it’d have been nice to have a rear mirror on my helmet.
I saw someone using bungee cords to fasten their sandals and sleeping bag to their rear rack and thought that was neat.
Excellent purchases this summer: bike computer (no need to look at my phone!), transition sunglasses (wind protection in lower light and fog!), top tube bag (no sweaty phone or melted energy bar in my jersey!)

Day-to-day

The GPX file mapped the entire route, and it was too large to give me turn-by-turn directions in the bike computer. I should have figured this out earlier and split up the files into more digestable chunks. But, in retrospect, not having the computer chirp at me for every turn ended up being pretty nice. Instead, when the computer thought we were off course, it chirped loudly and gave me turn-by-turn directions back to the route. Sweet!

The waterproof ACA map was amazing and helpful, as always, and I had it in my jersey pocket as a backstop for the technology we were using.

The guidance in the map suggested that the diciest part of the ride would be the bits on US-101 in the redwoods. This turned out not to be the case, perhaps because we were riding outside the tourist season (by design). When we were on US-101, the shoulder was generally large and there weren’t many blind turns. In contrast, once we reached the coast on CA-1, especially up north near Fort Bragg, the shoulder was more narrow, and cars were flying by. Most were generous about giving us plenty of space, but a few times, when there was traffic coming the other way, it ended up being tight.

Retention and resilience

Sun, 29 Sep 2024 00:00:00 -0700

I like to frame employee retention as tent stakes. When pitching a tent, one hammers tent stakes into the ground to keep the tent from blowing away in a brisk gust of wind. Similarly, in one’s employment, there are specific reasons, articulated or not, why someone sticks with a company.

When reorgs, strategy shifts, and market downturns start ripping up some of the tent stakes, as long as someone has enough remaining in the ground, the tent doesn’t blow away.

Common tent stakes include I like my manager! I like my role! I like my project! I like my teammates! I like the technologies/tools I’m using! I like how much I’m learning! I like the company’s future financial prospects! I like my salary!

The most durable tent stakes are those that are least likely to change – I like the company’s mission! I like the company’s values! I like the CEO! These may not be sufficient on their own to keep someone around, but the employees that have them as tent stakes often have a positive viral effect on the rest of the team.

Understanding your employees’ motivations enables effective change management, and it starts at the recruiting process. Hiring people motivated by the most durable tent stakes and not hiring those who seem overindexed on variables that are the most likely to change allows you to shape your team to one that will stick around through thick and thin.

I’ve also found that the tent stake analogy also applies to personal resilience and mental health. Life’s tent stakes – where one finds satisfaction and self worth – include work, family, hobbies, friends, health, religion, community, possessions, personal achievements, etc. Nothing goes well all the time, and the more places one finds satisfaction, the more places one might seek comfort while hammering a tent stake back down.

But if your life is defined by work and you don’t get that job offer or promotion, or your personal happiness depends on playing sports and you break your arm, your tent may be at risk of blowing off the ridge. Having the time and means to explore in a variety of passions and tent stakes is a luxury, but if you’re fortunate to have that opportunity, taking it can increase your likelihood for sustained satisfaction and happiness.

And according to a song I learned growing up of which I can’t find a trace on the internet, “what’s life? life is a big stack of pancakes.” Probably because “what’s life? life is sustained satisfaction and happiness” doesn’t have the same ring to it.

So fresh and so clean (clean)

Thu, 11 Jul 2024 00:00:00 -0700

It’s been about a decade since I’d relaunched this site on Jekyll, and the poor thing needed a visual refresh. The site was too text heavy, and the CSS was hacky and forced.

I just rewrote tgifunk.com and kept up the momentum to redesign mattspitz.me. I’m still not a web developer, but I like to think that the code and the design are much cleaner than they were.

Bootstrap v5 has a lot more utilities that make it easier to do the right thing once you know the right incantations. Unfortunately, one still needs to sift through the misery of web-developer StackOverflow for these incantations – I didn’t have a better experience asking ChatGPT for help.

Rest assured, ClippyJS is here to stay and is a bit more active with its boredom in the corner of the index page.

Enjoy the new layout, and as always, please share your feedback!

SFPL Explorer Map

Tue, 02 Jul 2024 00:00:00 -0700

I spent a lot of time at the West Portal library branch growing up, and when I went inside a few months ago for old time’s sake, the man behind the desk offered me a San Francisco Public Library Explorer Map. The map of San Francisco has a little gray circle for each of the city’s 27 libraries, at which one can pick up a unique sticker for that library.

I’m currently unemployed and love silly challenges, so I decided to collect each sticker by bicycle. Last week, I finished!

I began visiting libraries opportunistically – Visitation Valley, Portola, and Bayview after a morning of pickleball, Main Library after coffee in Hayes Valley, Eureka Valley after lunch in the Mission, etc.

Visitacion Valley

Portola

Bayview

Bernal Heights

Glen Park

Noe Valley

Main Library

Eureka Valley

Mission

Excelsior

Eventually, I realized that I’d need to make a concerted effort if I ever wanted to finish. I pulled up Google Maps and the list of hours for each library and mapped out a route to do 18 over two days. It reminded me a bit of the traveling salesman problem, a textbook example when learning about computational complexity.

Chinatown

North Beach

Marina

Golden Gate Valley

Presidio

Western Addition

Mission Bay

Potrero

Ocean View

Ingleside

Merced

West Portal

Parkside

Ortega

Sunset

Anza

Richmond

Park

The final boss was the Treasure Island bookmobile, open 2pm-6pm on Wednesdays. Since I’d biked to every branch and the main library, I wasn’t going to make an exception. Treasure Island is only accessible by bike from the east, so I biked over the Golden Gate Bridge and the Richmond - San Rafael Bridge to get to the eastern half of the Bay Bridge.

Treasure Island

The library buildings have their own stories, too, and some of the librarians were eager to share the specifics and history of their branch. When I told one about my mission to bike to every branch, she exclaimed, “over my dead body!” OK, then!

Potrero view

Park ceiling, reminiscent of Stonestown's

In addition to having a great story at the end of this quest, I also enjoyed exploring the city from a different perspective, even if that perspective sometimes involved a brutal hill.

This silly challenge was a lot of fun, and I need to come up with another one soon!

Working with me

Sat, 04 Mar 2023 00:00:00 -0800

Every few years, I update a document that lists my values, my modus operandi, and a few fun facts.

Here’s my latest, written at Vanta in March of 2023.

What I value

Delivering customer value: Vanta exists because of its customers: they pay us to solve real problems for them, and they can just as easily take their business elsewhere if we’re not meeting their needs. In order to realize Vanta’s potential, we must deeply understand our customers’ needs and brutally prioritize what will deliver the most impact for them. In product development, this is everyone’s responsibility, not just the PM’s.
Turning ideas into impact: In software, anything is possible – that’s why it’s such an exciting field! We must turn those ideas into tangible impact for our customers. We need clear next steps with dates/deadlines in our work as a forcing function to prioritize the right things and move them forward. While software development is a creative endeavor, teams benefit from clear direction and clear expectations as long as they understand the intent behind them and the impact they can deliver.
Providing context: I default to sharing as much of what I’m seeing as I can with my team, and I expect that context to cascade down through the organization. Context is empowering and leads to better customer outcomes when given to smart people with experience in their specific focus areas. The same applies for questions via Q&A or office hours – I’m an open book, and if I can’t talk about something, I’ll say so.
Realizing individual potential: I believe in hiring talented people that have a growth mindset and stretching them to help them realize their potential. In practice, I encourage my teammates to take on new responsibilities, give them feedback, and support them however I can. I’ve found that people often surprise themselves with how quickly they’re able to take on new responsibilities and deliver more impact. I also expect individuals to own their career growth – I will not be more invested in someone’s career than they are.
Giving and getting feedback: I give direct feedback, I expect to receive direct feedback, and I encourage my teammates to do the same. It’s the fastest way to build trust and to get to better outcomes for our customers and for our business. Please don’t be shy.
Surfacing the best ideas: I believe that incorporating a diverse set of perspectives into decision making leads to better products and better outcomes. It’s everyone’s responsibility, especially leaders’, to create an inclusive culture where people feel comfortable surfacing their ideas and know that their ideas will be heard.
Bringing our best selves to work: We can’t control everything about our jobs, much less our lives, but we can control who shows up at our desk in the morning. Let’s bring a positive attitude, celebrate our teammates’ wins, help our teammates grow, work hard, push ourselves, and always be learning. In private, I’m always available to support my teammates in any way, professionally or personally.

How I work

I believe that everything is a choice and that there are few truly immutable constraints. I operate best when discussing tradeoffs rather than the merits of a single idea. When reviewing proposals for larger decisions, I expect to see a framework to evaluate success and alternatives considered.
I prefer to try new things and retrospect instead of finding ideal solutions, particularly for team processes. Our work environment changes frequently, and existing processes grow stale quickly. Let’s try new things and schedule time to reflect rather than seek perfection.
I prefer to be overinformed, as long as it doesn’t create extra work. I like to lurk on noisy mailing lists and Slack channels, and I like to follow along with project plans. It’s an opportunity for me to build context.
I have a family with small children, and I’ve found that I’m at my best both at work and at home when I compartmentalize my time to be present and focus 100% on whatever I’m doing. In practice, this means that I’m offline for dinner and kids’ bedtime and back online later in the evening, and I work in a couple of focused chunks on the weekend. This also means that I consume way more caffeine than I did a few years ago. Not a coincidence.
I manage my own interrupts, and I want to know if something needs my attention. Please don’t be shy if you need my attention. I usually respond quickest to Slack, and I welcome a text or phone call if there’s a true emergency.

Fun facts

🌉 I grew up in San Francisco, lived in New York for ten years, and moved back in 2019.
👨‍👩‍👧‍👦 L and I have two little kids: L and F.
🗽 With a few others, I opened Dropbox NYC in 2014 and was its first site lead for five years.
🚴 I prefer to bicycle to work whenever I can.
🖖 Until I watched all of DS9, TNG was clearly the best Star Trek. Now I’m not so sure. I’m still working my way through Voyager, and some of the new Trek is quite good, too.
🎸 Performing live music is one of my favorite things to do, and I wish I could do it more often!

F = asleep

Cookies from my Dropbox NYC going-away party

I played in a Pearl Jam cover band in New York for many years

SF bike commutes are warmer than some NYC bike commutes

Note: I’m wearing a hat in these photos more than I normally do. Also, I swear that I have other hats.

Cultivating effective product engineering

Thu, 22 Dec 2022 00:00:00 -0800

Product engineering – developing software that meets a customer need – is a skill that is developed rather than taught. When deployed effectively, strong product engineers have extraordinary leverage, crossing crossfunctional boundaries and getting (a lot of) stuff done.

As an engineering leader, developing and unleashing product engineering is a force multiplier. Vanta has grown quickly, and I’ve been thinking about how best to scale product engineering with that growth. Ultimately, cultivating effective product engineering comes down to motivation, empowerment, and execution. In short, show great engineers the problems, give them the tools to approach those problems, and get out of the way.

Motivation

One cannot design and build good software without knowing the underlying need they’re solving. I’ll assume that engineers at one’s company ultimately care about the customers’ and, by proxy, the company’s success – if that’s not true, one has much bigger problems to solve.

Motivation is derived from customer empathy. Personally feeling the customers pain and the potential that software can bring is deeply motivating, and developing customer empathy is a matter of ritual and access to customer feedback. How a leader structures meetings, what they talk about, and where they spend their time indicates what’s most important to them. Putting customer focus at the top of every team meeting, ensuring that all works are framed in terms of customer impact, and actively engaging with product work all signal that customer needs are important to a leader, and the team follows suit.

One also needs to limit friction to getting access to customers. Depending on the product, employees may be customers – ask them for feedback! At early-stage companies, might know all customers by first name – ask them for feedback! As a company grows and develops support teams that talk to dozens of customers a day, these teams becomes a proxy (but not a substitute) for talking to customers – ask them for feedback!

Seeing the product through a customer’s eyes develops a burning sense of urgency for a product engineer to fix all the problems and realize all the opportunities.

Empowerment

Once an engineer feels a customer’s pain, they must feel empowered to act on it. Otherwise, the urgency dies on the vine.

In a typical EPD (Engineering, Product, Design) crossfunctional team, Product is typically responsible for deciding what to build that best meets the business need, Design is typically responsible for the design and user experience of that feature, and Engineering is responsible for delivering a product in a way that appropriately balances speed and quality. Many companies, whether or not they realize it, treat this relationship linearly – a product manager designs a product requirements doc and hands it to a designer, the designer develops a design spec and hands it to an engineer, and the engineer picks it up for the first time and builds it while the PM and designer watch.

The best EPD triads (or three-legged stools) are better than the sum of their parts and collaborate at each step of the way. The PM kicks ideas around with Engineering and Design as part of defining product requirements, Design and Engineering build prototypes, get feedback, and iterate on the requirements and specs. Even if Product is the final decision maker and ultimately accountable for the product requirements, leveraging everyone’s ideas and engagement ultimately leads to a better product.

Not every product change needs to go through this process, though. Connecting engineers directly with customers’ needs should leave them chomping at the bit to fix them. In some cases, especially for straightforward fixes and improvements, an engineer can drive changes on their own, perhaps asking for feedback or review from Product/Design before they ship it. Shipping each little fix or improvement offers a hit of dopamine, and tightening the iteration loop keeps product engineers wanting more.

Execution

Now that engineers are motivated and empowered, the final piece of effective product engineering is proper execution against more ambiguous and/or complex customer needs. Optimizing for learning – sequencing discovery and delivery in phased milestones with crisp hypotheses and purpose for each – enables a team to spend its time efficiently in solving the customer need. Framing the project as a series of questions (“will anyone pay for this?”, “is this extra configurability necessary?”, “do customers want this feature?”) and associated deliverables to test those enables a team to scope the solution to an appropriate MVP iteratively and quickly. Each project milestone should be framed as an opportunity to reevaluate the viability of the project and kill it if necessary.

Engineering time is often the scarcest resource, and many leaders hesitate to cancel or downscope projects they’ve invested in. Instead, optimize for learning, embrace failure, and celebrate putting down projects that aren’t going to deliver meaningful customer value. Engineers can tell when they’re working on something useless, and a properly motivated product engineer will want to spend their time on something meaningful, anyway.

Intro to retros

Wed, 04 May 2022 00:00:00 -0700

I recently presented an introduction to retrospectives at Vanta as a tool for teams to use in a hypergrowth environment. The presentation was well-received, so I’ve converted it into a post in it’s interesting to others, too!

Why retrospect?

Companies that are growing as quickly as Vanta are moving fast and need to move even faster to build their presence in the market.

In this environment, these two things are true:

Mistakes will happen. We’re moving fast, and things will break.
What works today almost certainly will not work tomorrow.

We must embrace these truths, expect change, and anticipate the continual need to adapt. Retrospectives are a tool to discover opportunities for improvement both retroactively and proactively.

In Engineering, we use two types of retrospectives:

Incident retrospectives: “Something bad happened. What did we learn, and what will we improve for next time?”
Team retrospectives: “How might we improve how we work to preempt future bad things from happening?”

Incident retrospectives

Quality is a choice that trades off against speed. The best way to ship a product with no defects is not to ship a product at all. We’re moving fast and shipping a lot, and sometimes, things don’t go as planned.

When something goes wrong, the root cause is rarely pure human error. We need a depersonalized and blameless way to reflect and identify improvements to our processes and tools to learn from our mistakes and to prevent them from happening again. Framing incident retrospectives as blameless is essential – blameless retrospectives encourage honesty and lead to meaningful improvements. In contrast, creating a culture where it’s not OK to make mistakes discourages surfacing and addressing real issues.

We have an incident playbook to identify incidents, resolve them, and communicate internally and externally. When an incident is resolved, we have a retrospective template that covers, roughly:

Timeline (what happened?)
Root cause
Resolution (how did we fix it?)
What went well?
What could we improve?
Action items

Every two weeks, leadership from Engineering and Customer Experience reviews these retrospective documents to coach the team in diagnosing root cause issues and to ensure that we have appropriate action items moving forward. While it’s OK to make mistakes, we must use these opportunities to learn from them going forward, and this is the forum to ensure that that happens.

Team retrospectives

We often say that “every week is a new week at Vanta.” It’s true! We’re growing our customer base and team very quickly, and we’re building this rocketship while flying it. One of Vanta’s principles is bias for action, commit to iteration, essentially acknowledging how fast we’re moving and embracing evolving how we work.

A tool we use to identify improvements proactively is the team retrospective. Essentially, we’re assessing how we work today and identifying potential improvements before things break.

On a ~monthly basis, Engineering teams dedicate time to reflect on projects, processes, and working relationships to identify opportunities for improvement.

Teams can run retrospectives however they’d like. Our default format is:

Collect opinions and potential improvements from teammates independently to avoid bias, either in a shared document or on post-it notes. Our default framework is:
- Start (what should we start doing?)
- Stop (what should we stop doing?)
- Continue (what should we continue doing?)
- Puzzle (what questions do we have?)
Assemble these ideas, grouping them by theme.
Teammates vote on themes they’d like to discuss.
Discuss top-voted items and, where appropriate, next steps.

Like incident retrospectives, effective team retrospectives are depersonalized and blameless. When a team ritual grows stale, it doesn’t matter who came up with that idea in the first place. It’s broken, so rip it out, try something new, and move forward. Depersonalizing decisions encourages more people to volunteer suggestions, and a team that incorporates more opinions and feedback almost always delivers better outcomes.

One secret benefit of running team retrospectives run well is that teammates have a venue in which to surface their complaints. When someone brings up constructive feedback for how we work in a 1:1, I direct them to the next retrospective where the whole team can hear it. If others agree, great, let’s fix it! If the team decides to prioritize other improvements, they’ll see that in a way that’s fair and transparent.

Wrap

So that’s it! I hope you find these tools useful. Next time something breaks, consider running an incident retrospective to avoid making the same mistake again. Next time someone thinks your team’s processes feel stale or inefficient (spoiler: this is often in a high-growth environment), consider running a team retrospective to identify improvements.

Don’t squander a good mistake, no matter how small or spectacular; take advantage of opportunities to learn and improve! Remember, blameless retrospectives encourage honesty and lead to real improvements.

Management beyond relationships

Sat, 23 Oct 2021 00:00:00 -0700

I’ve had a few major inflection points in my career as a manager. Previously, I’ve written about managing without domain expertise. Recently, I’ve had an opportunity to reflect on another: management beyond relationships.

I have high EQ, which, for whatever reason, stands for “emotional intelligence” – I read people well and build trust quickly. In practice, this means that I’m a good recruiter and can sense challenges that individuals and teams face before they manifest. Unfortunately, having high EQ has also been a crutch that enabled me to manage much larger teams than the immaturity of my management skills should have allowed.

Since I was a member of the founding team at Dropbox NYC, almost everyone on my team was someone that I’d recruited personally. I had a relationship with each person joining my team coming in, and there was at least some implicit trust from the start. When my team was small, my team processes were unstructured, and I leveraged relationships to understand what was happening on my team and figure out how I could help. I was able to get away with managing almost 20 people this way before I hit a breaking point and had rude awakening.

In an annual Dropbox reorg, I inherited two teams based in San Francisco and expanded the scope of my teams in New York, about 30 people across 4 teams and beyond what I could manage effectively. I doubled down and spent a lot of time and effort running my old playbook – understanding what was happening on my team by leveraging conversations rather than process. I was frustrated, couldn’t figure out why, and nearly burned out.

With the next year’s reorg, I had a team of 50 people and decided to reevaluate. During one of Dropbox’s Hack Weeks, I hacked together a better way to run my organization. I created regular reviews to check in on my teams’ status, key metrics, and operational postmortems, and I designed templates for quarterly staffing assessments to track performance and career aspirations for every individual on my team. All of this process de-personalized my involvement in the team, created clearer expectations for engineering managers, and enabled managers to take more ownership and responsibility for their teams.

As my organization continued to evolve, I built some metaprocess to ensure that my operating cadence was effective. Each time that I needed to check something on my team, I asked myself whether I had a process for that (e.g. “would I get an answer to this question in our next execution review?”) and whether that process was happening soon enough to answer my question. The extra check before digging in helped me refine the agenda and cadence of these meetings and often saved me from disrupting my team.

Leveraging process over relationships enabled me to scale myself to managing much larger teams more effectively and with significantly less stress. I can still leverage my EQ, but I no longer depend on it, and everyone is better off for it!