“Make no little plans. They have no magic to stir men’s blood and probably themselves will not be realized. Make big plans; aim high in hope and work, remembering that a noble, logical diagram once recorded will never die, but long after we are gone will be a living thing, asserting itself with ever-growing insistency. Remember that our sons and grandsons are going to do things that would stagger us. Let your watchword be order and your beacon beauty.

Think big.”

– Daniel Burnham

Present Day – August 2013 – Washington DC launch

We were now shipping around 150 driver onboarding kits a day. And I had the paper cuts to prove it. Have you ever sliced your finger along the edge of a cardboard box?

Anyway, these shipments were being spread across several markets: San Francisco, Los Angeles, Seattle, and now Washington DC.

I hired another TaskRabbit named Emily. We needed the help. She was awesome.

Steve and I sat in the corner office, both of us in ball caps and the new black Lyft hoodie he’d commissioned: American Apparel, “Lyft” on the chest in white, skull and bones on the back, sporting a pink mustache.

As usual, we were talking shop.

“The black card’s the one with no spending limit, right?” I asked.

“Not exactly,” Steve replied. “None of the high-end cards really have a set spending limit. Having one is more about the perks.”

“Like what?”

“Lounge access. Upgrades. Concierge service. You can call them, give a budget, and they’ll find you gifts, book last-minute dinner reservations, concert tickets – whatever. It’s a power move.”

The points game was all still new to me. I’d been taught to only use credit cards for emergencies, similar to using AAA for a tow. Six months earlier I’d used my credit card to pay for a root canal because I was broke and didn’t have any insurance.

“You accumulate points each time you use it and you use those points for upgrades or to pay for things – just make sure you get the right card – that’s the key. Use it like a charge card and don’t carry a balance. I recently paid for a gift using points.” he added.

An impromptu lesson in financial literacy was not on my bingo card that day.

In retrospect, that root canal would have netted me a load of points.

I examined his gold card in my hand, which was quickly becoming my gold card.

The catered lunch arrived: trays of sliders, fries, and a salad option. The team started queueing up.

“Wanna grab lunch? It’s sliders. I’m starving.” I said.

Steve shook his head, “I’ll wait for everyone else to go first.”

Hmm.

I slipped out but hung back, waiting for the others to grab their food before digging in myself.

Eventually, Steve emerged and grabbed some food and took it back to the office. I didn’t follow him back in, instead joining the rest of the team.

Branding makes perfect

Lyft’s branding attracted a certain type of personality early on, internally and externally. Branding was key, as each company needed to stand out beyond the technology.

We didn’t embrace the ‘rich kid flexing on Instagram’ persona (Uber), or a lack of personality (SideCar).

Sorry SideCar, you guys were first movers but that’s about it. Love you.

Actually… SideCar was more like the honor roll student who did all the work on the group project but got none of the credit.

We were the friend with a car.

And ‘your friend with a car’ was real. It was quirky, fun, yet down to earth at a time when things were new and evolving quickly. The energy was infectious.

Lyft employees and drivers drank the kool-aid pretty heavily then, and hey, I had a few pints myself.

If Uber was the Yankees, then it’s only fitting that Lyft was Billy Beane’s Oakland A’s during the Moneyball era – speaking for the Ops team specifically – the overlooked, barely employable, diamonds in the rough.

The thing that most recruiters often miss while evaluating resumes is something that you can’t learn at Stanford or Harvard:

We get on base.

What does that mean?

We may not look like much on paper, but we move the ball forward. Scrappy, weird, reliable.

That’s how you win: quietly, consistently.

Flashback – Oakland – July 2013

It was Summer, and somewhere in the office Justin Timberlake was playing. The Drive Team ate a free catered lunch each day shoulder-to-shoulder along a row of communal tables near the kitchen. This is where I got to know the other people in the trenches during my first days at the company.

“I got this in Healdsburg over the weekend,” said Nicholas Rozzi as he produced a bottle of BBQ sauce that he’d picked up on a weekend trip through wine country.

“Healdsburg. Where’s that?” I asked.

Rozzi and others ribbed me for not knowing the basic weekend booze cruise geography of wine country.

“My man here is from Stockton and drinks wine from a box, you’ll have to excuse him” joked Mike Diaz.

I admitted that yes, I too had had my share of boxed wines and vintages like Charles Shaw.

I was a slow burn but gradually let my layers and humor show.

Family gets thrown around way too much in startup land, and don’t even get me started on the big corporate companies. I’ve rolled my eyes at the term more times than I can count.

This experience was the closest that I’ve ever gotten to that at work.

Each startup takes on the DNA of its people from the founders all the way down to, well… the Shipping Lead. If your ship is full of schemers, liars, and rats, then that’s likely the culture you’ll cultivate.

I digress.

Visions of Amazon

One afternoon, our UPS driver rolled out with another big load. He made several back and forth trips, piling dozens of boxes on his dolly. We were fast becoming friends.

His name was Rob.

Shel was cleaning up while I updated our numbers. Our shipping volume began to feel like less of a scrappy startup and more like a legit fulfillment operation.

I opened up my browser to the TaskRabbit website and added another Rabbit to the roster.

Shel tracked daily counts. I plugged them into a growing spreadsheet that I was building, our unofficial database. I would cross-reference it with the data I pulled from HQ. I looked for deltas, patterns, trying to understand throughput and forecast demand.

I’d just learned what a delta was after someone repeatedly used the term at a meeting regarding a forecast.

Side quest: Delta (noun): “the difference between what we thought we were going to ship versus what we actually shipped.”

That unnamed someone loved throwing around jargon, and that’s about it.

My manual backroom hustle was evolving into a system and I wanted to make sure it could scale.

At the end of day, it was just Shel and I at the office. I paced with beer in hand, amped up, waving my hands, ranting about my vision.

“Nationwide.”

“International.”

Steve and Travis had pulled me and the other Drive Team Ops Managers into their corner office before the team left Oakland and floated the idea of Sydney, London, or somewhere in Canada as a potential first international market.

A place where people spoke English and we didn’t have to translate the app.

I started to believe that we could run this all in-house. Hell, I embraced the challenge. I even conducted preliminary research of office warehouse locations in Sydney for an international version of what we were doing here in Oakland. I wanted to build Lyft’s internal Amazon.

I monologued at Shel.

“We’ll build, manage, or ship anything. Anywhere. We’ll have multiple hubs to support us nationally and internationally.”

“I’m a Six Sigma yellow belt!” Shel exclaimed.

I stopped mid-rant.

“It’s no black belt. But I can help you set up the processes to get us started,” they smiled.

That’s the kind of shit I liked about Shel. Turns out they’d signed up for six sigma training at a prior job, and it was all starting to bubble to the surface.

The next day, over Indian takeout, Shel and I sketched out a plan: how to streamline kit production, manage new requests from HQ and the field, and structure the office as our first fulfillment hub.

Today, we were building kits to order: grabbing components out of boxes and assembling them from scratch. It was messy.

Tomorrow, we’d switch to stations.

One TaskRabbit for phone mounts. One for carstaches. Another for stickers, cables, and whatever else was in the welcome kit that iteration. Each component was de-boxed, re-bagged, and relabeled with Lyft branding. We’d work to build inventory during the morning shift, then assemble kits in the afternoon, timed to when background checks cleared and driver approvals came through.

Shel ran point on QA, quietly catching mistakes before they left the building. I handled ops flow, staffing, and tracking the daily numbers. Our new system was raw, but learning how to breathe.

Side quest: We pulled shipping lists around noon each day. The timing wasn’t random. Around lunch, background checks would clear, and that bump in cleared drivers gave Ops Managers something to brag about in the daily activation numbers.

That’s showbiz, baby.

“We should find a door that you could use as your desk. Like Jeff Bezos.” joked Shel.

I glanced over at the slab of corrugated wood from IKEA that served as my desk. It might as well have been a door. I liked the idea, but maybe another time.

Shel and I mapped out the zones for the new office layout: build, staging, storage, lunch area.

Full startup feng shui.

“We need chairs,” Shel said. “In case we ever get, you know, visitors.”

Visitor area.

I nodded. They darted off to scavenge chairs from storage. I loved the optimism.

With everyone else now in SF, I’d taken over Steve and Travis’s old corner office. Shel claimed my former desk. They brought in a personal laptop and a Bluetooth speaker, for office music. Eventually, I gave Shel access to my Google sheets and other documents for input.

I wanted to walk into a space that felt intentionally built, not just for us, but for anyone who walked in.

I wanted visitors to feel like they’d walked into the special ops unit of a big startup: leaner, scrappier, and built to move fast.

On the surface, most people just thought of my team as ‘shipping.’ But what I was building was a version of a Moonshot factory. The kind of space where crazy ideas could be green lit, prototyped, and shipped before happy hour.

Outside of work I even started poking around to understand product management to see what it would take to build a feature for Lyft’s app. Fuck it, why not?

The office itself was quickly being outfitted: tape guns, box cutters, office equipment, shelving for inventory, Mechanix gloves (for paper cuts), the works. I’d practically bought out the entire ULine catalog.

“I bought a few industrial packing tables from ULine, along with a few other things… just a heads up.” I casually messaged Steve.

Moments later I received a thumbs up emoji: 👍

I took his response to mean: excellent work, carry on.

That night, I drove Betsy across the bay bridge like a bandit.

I slipped into Lyft’s SF HQ. Not surprisingly, the place was still buzzing. Someone was casting the Giants game on one of the big TV screens at the office.

“Is Corey still around?” I asked a rando who was pouring himself a drink in the kitchen as I passed by.

“No, he’s gone for the day.”

Great.

I made a beeline for the supply room and filled my car with anything that wasn’t bolted down: Lyft posters, a whiteboard, office decorations, decorative green plastic moss for the walls, some framed photos, random Lyft tchotchkes, even a large indoor plant.

I enlisted one or two people to help me load all of this stuff into Betsy.

I even snagged some artsy leftovers from the Creative team’s area.

Our Oakland outpost was going to look like a Lyft-branded HQ, with some creative liberties.

I was on a tear.

We ❤️ Logistics

One afternoon, there was a knock on our office front door.

I craned my head out of my office while Shel went to let the visitor in. I paused the Spotify playlist and put on my Raiders ball cap.

Enter Edwin Rikkelman. Middle aged. Picture Jeff Daniels.

He was business casual: blazer, no tie, slacks. An account executive with UPS, covering the East Bay region. Easy talker and seemed trustworthy. Like my first visit to this office, he stuck out like a sore thumb.

He took in the space around him, then studied Shel and me. Likely wondering what kind of funky startup we were running.

“Who’s in charge around here?” he asked.

I stepped forward. “I am.”

It was the first time I’d said it out loud. It didn’t feel fake. I’d say it was imposter syndrome, but maybe it was just a new feeling.

We exchanged business cards and had a friendly intro chat. I gave him a tour. I went into detail on everything. I pitched him the future.

“So you only ship these pink mustache pillows?” he asked as he examined one up close.

“We call them Carstaches. And we ship them as part of an onboarding kit for each new driver – it’s the final step before they hit the road. Eventually we’ll be expanding to non-onboarding items like t-shirts, hats, and pretty much anything. Nationwide. International. The sky’s the limit.”

I glanced over my shoulder and caught Shel staring. We exchanged smiles.

I pulled out my iPhone and showed Edwin the Lyft app. I explained how it worked. He asked if this was my company – no, it wasn’t – but I felt an urge to say yes.

“Sounds like a great way to make some extra dough,” he added.

“It is. You should consider becoming a driver or passenger. It’s great for a night out.”

Edwin was wrapping his head around this new idea of ride sharing.

Pink Carstache. Car rides. Strangers in cars.

It was too new for him and I didn’t blame him.

“I don’t know if this is my thing. But I think what you’re building here sounds great. Have you thought about how much you’re spending on shipping?”

Of course. I knew the numbers by heart.

“Yeah, you got any discounts that you can hook up?” I asked instinctively.

“I think I can help you with that,” he smiled.

We moved our conversation to the large conference room at the rear of the office. There was a long table. I sat at the head of the table while Edwin sat to my left.

I rattled off some numbers from our end: current outflow, upcoming market launches, estimates, hand-wavy shit.

He rattled off some recommendations, including:

“By the way, you don’t need to overnight ship packages that are going from Oakland to San Francisco or San Jose, or anywhere within 100 miles for that matter. Just use UPS Ground shipping. They’ll get there in one business day and cost less,” he recommended.

“How do you know so much about our business?” I asked half-jokingly.

“You’ve been using our system. We identified a large spike in shipments coming from an old office address in Jack London Square that used to belong to an architectural design firm.”

He wanted our business.

“We’d been monitoring your shipping activity for a few weeks now to see if it was some kind of outlier.” He paused.

You’d think we were shipping weapons.

He continued, “then one of our analysts recognized the name on the return address: Lyft. Turns out they’d used the service one night when they were in the city for dinner and a Giants game.”

I sat back in my chair. That was interesting.

“Okay, let’s figure something out,” I said, noncommittal.

We agreed to meet up in a week. I’d gather some more data and attempt to build a forecast, and Edwin and his team would begin to iron out a plan on their end.

As I walked Edwin out, I looked around at the space that Shel and I were molding out of chaos.

Edwin closed the door behind him and disappeared into the elevator.

Validation.

I whipped around and glanced at our new visitor area. There was a large pile of green plastic moss on the floor, waiting to be pinned to the bare wall.

Next to it were four chairs side by side: three molded plastic chairs in magenta, and a fourth white chair – a basic folding model. I grabbed the white chair and moved it to storage and replaced it with a tall plant that I’d managed to fit in my car.

Better.

I took a step back and admired the view. The place was still a fucking mess, but coming together.

Something clicked. And here we were.

I looked past the new waiting area at the freshly delivered pallet of cardboard boxes stacked in the storage area, and the reality settled in.

Edwin wasn’t just offering us a discount; he was offering us scale.

Shel approached with a backpack slung over their shoulder, on the way out.

“Aren’t you glad we installed this new visitor area?”

“Yes,” I replied.

“Oh, and Alex?” their tone more serious.

I turned to Shel.

“We need another TaskRabbit. Like, tomorrow. I caught a glimpse of our funnel and it looks like a tsunami headed our way.”

I nodded.

“And we’re out of shipping labels. AND the toner cartridge for the printer is on its last legs.”

I was half daydreaming but feeling ready to own the chaos of hyper-growth.

“Yep. Thank you.”

Shel would become my eyes, ears, and reality check.

If my hand-wavy math was right, we were about to hit a volume that no amount of cheeky hacking could handle.

We weren’t just shipping packages anymore. We were scaling culture.

How do you forecast a rocket ship?

CUT TO BLACK

🎧 Cue “Figure It Out” – Royal Blood

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Next stop: Chapter 5 – Coming Soon

"It's better to be a Pirate than join the Navy"

– Steve Jobs

Summer 2013 (continued)

To say things were moving fast was an understatement. The driver funnel was growing by the minute, especially in San Francisco, where word was spreading quickly about the app where you could get paid to give people rides.

Not the Uber one.
The pink mustache one.

It’s funny how quickly people got past the whole “stranger in your car” dynamic when money entered the equation. Gig economy wasn’t a term yet, but the instinct was there. People were embracing the hustle – and Lyft was one of several tech-enabled companies disrupting that paradigm in real time.

Everyone at the company embraced the ambiguity and chaos.

I finally understood the true definition of a fast paced environment.

Sans crew

I sat Steve down. Our meetings were always informal: half hallway catch-ups, half therapy sessions.

“I need to hire someone to help me,” I started.

Steve stroked his beard and eyed me under the brim of his baseball cap like a card player in an old western saloon. His default move when deep in thought.

“We didn’t plan for you to hire any FTEs. We figured you’d manage the operation and eventually outsource a 3PL.”

Side quest: A 3PL (third-party logistics) is a hired vendor that stores, packs, and ships your inventory. No warehouse? No trucks? No problem. They’re the backstage crew of e-commerce – unseen and overworked, but essential. It’s how Amazon can deliver your impulse buys in 2 days or less.

End side quest.

“So like… nobody?” I responded.

Steve likely saw that I was processing it, but the hesitation on my face said what I didn’t.

“No. You can’t hire anyone new.”

Then the classic startup platitude: “You want to scale yourself out of a job.”

I deadpanned: “So you want me to work hard just to be unemployed? Awesome.”

Steve may have missed the sarcasm.

“No dude, you scale your way out, and then we’ll drop you into the next thing. That’s how it works.”

I hated not getting what I wanted when I clearly needed it.

I thought for a moment. “What if I poached someone who already worked here?”

Steve shrugged. “Try it.”

Pitchfest

I pulled Drive Team members aside, took them on quick walks to Blue Bottle, and pitched them on joining me to help build out the operation. I wanted to shake the mailroom vibes I’d been tagged with by those who didn’t understand my work.

No dice.

I approached my buddy Mike Diaz, but he saw me coming. I lied and told him Travis was reassigning him to my team. His brown skin turned pale.

“Bro. Are you kidding me? I can’t go back to manual labor.”

I laughed and came clean. He joked about it, but yeah – he wasn’t leaving his headset behind anytime soon.

Nobody was biting. Not even part-time.

It reminded me of graduate school during my time in the producers program at Chapman University. I pitched an idea for a WWII movie about the true story of a squad of Mexican fighter pilots who supported the U.S. in the Pacific – this was in front of my class to an actual production executive. A few minutes in I could tell that the exec didn’t seem too interested. After, my class filled out feedback cards rating my idea, pitch delivery, and whether they would work with me on any project.

Out of the 24 students, only 2 indicated that they would want to work with me.

No one liked the idea.

That’s show business, baby.

Reinforcements to the Front

Then, a break. One day, a new intern appeared. The type of announcement that happens in real time because someone forgot to give us a heads up.

HQ had airdropped him into the Oakland trenches. His name was Michael Kelleher. Tall, clean-cut, with a bit of Loyola Marymount bro energy. I half-expected some entitlement, but right away, he surprised me: grounded, quick on the uptake, easy to trust. And in no time, he built a reputation as someone who could deliver.

Michael gave me much needed breathing room. He wasn’t afraid to get his hands dirty, and together we built and shipped dozens of kits daily during his stint – 36, 44, 65, 72… and climbing – all on top of any side projects for the team that he could tackle. He was sharp and probably would’ve scaled this operation on his own if I let him.

Michael even came up with the idea for the Lyft Lost & Found program. Drivers were reporting lost items via our new customer support team, and Michael jumped at the chance to build a process: prepaid labels and packaging sent to drivers, a storage locker for returned items (thanks, ULine), reuniting items with passengers when possible, and charity drop-offs for unclaimed stuff.

Not super scalable, but it was on brand.

Wearing All the Hats

As summer went on, my day-to-day evolved as I found more things to tackle. I wasn’t just building and shipping kits – I was unofficially running the Oakland office too. Corey Lambert had just started as Lyft’s official office manager, but he was across the Bay at HQ prepping for our first of many office moves.

While Drive Team members like Amber Cady handled lunch orders for Oakland, I took on everything else: office supplies, Costco and IKEA furniture orders, you name it. Steve handed me his AMEX, the gold one. I guess I was the office manager now – unofficially – and I fully embraced it.

I still felt like an odd duck, but my confidence was growing.

More people were hired. Laptops arrived weekly. Beth Trame had launched Lyft’s customer support and Trust & Safety teams and set up camp in Oakland, making office real estate tighter. Carstache deliveries kept piling up. The wall of pink fur kept growing.

Here’s a picture of a wall we built after one of those deliveries.

August 2013 – Back to School

Michael's internship ended faster than I expected. He seriously considered dropping out to work at Lyft full-time – and a few of us, me included, encouraged him – but saner minds prevailed and convinced him to finish school.

I needed a backup plan. Corey recommended TaskRabbit. He’d hired someone from the platform to build desk chairs around the Oakland office, and people liked the Tasker. I was so busy I hadn’t even noticed them.

This was a great way to get around the no hiring rule. A loophole I planned to fully exploit.

There was so much happening in Silicon Valley at the time – especially in San Francisco – there was an app or platform for everything. I quickly began educating myself on everything I could about these emerging companies. I read TechCrunch, subscribed to tech newsletters and resources like Product Hunt, and even StrictlyVC, which was new in 2013. These helped me understand which companies were launching and getting funded.

I was learning to see the patterns and better understand the ecosystem that was quickly emerging around me.

Enter Shel

Meet Shelbert “Shel” Smith.

Back then, they went by Shelly. They later transitioned, so I’ll be using their current name throughout. Shel was sitting on the floor, listening to music and cheerfully assembling a desk chair. Short hair. Glasses. Loud, electric energy that made them impossible to miss (though clearly I had). A burner. Builder energy. Misfit. Perfect for my team.

We intro’d. I made awkward small talk. Then my Billy Beane moment:

“What are you doing next week?”

I pitched them on helping me scale. They said yes.

One caveat: they’d be out for Burning Man in late August. Fair.

“Cool. See you Monday.”

It was a small win, but it felt like I’d just hit a home run.

A Self-Promotion

The company rolled out business cards for everyone: kraft card stock, Lyft colors, a quirky quote on the back. Classic startup charm.

I have a bunch of these in an old box somewhere.

When HQ asked us all to submit our name, title, and contact info, I stopped.

My title was still officially Shipping Lead.

Fuck that title. I’d outgrown it.

My ego craved something that didn’t put me in a box. But more than that, I needed a title that reflected where I felt I was going: building scalable systems, managing a supply chain, holding the chaos together with duct tape and instinct.

I typed it out:

Logistics & Operations Manager.

I didn’t ask for permission. I just submitted it.

I briefly considered “Director of” or “Head of,” but stopped myself. This wasn’t startup cosplay, it was a signal. I wanted to be seen as the person who made impossible things happen.

Steve noticed. I’d like to think he respected the move: the same way the commander respected Maverick and Goose after they pulled off their MIG stunt… and still sent them to Top Gun.

I now had a TaskRabbit quietly filling the gaps. There would be more. It wasn’t officially sanctioned, but it worked.

And yeah, I borrowed an idea from Uber. Late one night I was scrolling their careers page and saw they had a similarly titled role, Operations & Logistics Managers – these were strategic, data-driven operators powering growth behind the scenes.

Fuck it. I’ll build the Lyft version.

Looking back, that’s when it started clicking for me: the rules are only real if you agree to them.

There’s a quote I once read from Travis Kalanick – Uber’s CEO and our not-so-friendly rival – and the message stuck with me:

“Stand by your principles and be comfortable with confrontation. So few people are, so when the people with the red tape come, it becomes a negotiation.”

I didn’t admire everything about TK’s leadership. But I respected that kind of clarity.

When you’re building something in real time: fast, messy, high-stakes – waiting for permission is just another way to lose.

Man on Fire

Props to Shel: working with me by day, building an installation for Burning Man by night. I admired their side hustle.

I really need to hit up the playa sometime.

Before Shel left, we pre-built a ton of driver onboarding kits to get ahead of the forecast I mapped out – something to lighten my load while I rolled solo that week.

You might be thinking: “Why not hire another TaskRabbit, Alex?”

Damn good question. Part inexperience, part control.

Shel was a talented, unsigned free agent with something to prove. Chip on shoulder. They took ownership from day one. What if the next person didn’t?

I feared the wrong person would come through the door and I’d watch things go sideways.

Visitors

Despite my newfound confidence, it’s worth noting that even a few months into the role I was experiencing regular bouts of imposter syndrome.

Lyft was full of people my age and younger who were gifted, had deep connections in Silicon Valley, graduated from top schools, worked as consultants, or had far more exposure to startup life.

I kept telling myself that I was just a kid from the southside of Stockton.

Word must’ve gotten around that Shel was out and I was riding solo because visitors began trickling into the office.

First, Nick Greenfield dropped by. Confident and sharp – he’d been handling special projects for Lyft and was an original employee of Zimride, Lyft’s predecessor. He wanted to hang out and shadow me for the day.

“You need help around here?” he asked.

Hell yeah.

I played it off like I had everything under control but in reality, I needed help. My original forecast had been a bit off, and without Shel, I was up to my eyeballs with demand.

We chopped it up. I walked him through the kitting process, and my vision for the team.

“Team? But I hear you’re a one-man show.”

“True. But I’m working with Steve and Travis to fund more heads. We’ll be expanding soon.”

Maybe I embellished a little.

I’d gotten so used to pitch-mode, it just rolled out naturally.

Then Nick pitched me on joining my team. I thought he wanted to report to me. But instead, he proposed I run kit building operations while he handled strategy. He casually sprinkled in the fact that he studied international business at Stanford.

My internal eyes were rolling.

For a moment, I thought I was being offered backup. Instead, I was being offered a co-pilot’s seat on my own plane. Impressive resume, but no thanks.

Nick landed fine. He left Lyft not long after to run growth at Washio, another on-demand startup.

Fun fact: Nick later helped me land a job managing the SF/Oakland markets for Washio. He’s now CEO of Candid.

Not long after Nick’s visit, as if on cue, Justin Lyn showed up alone to the Oakland office.

I liked Justin. He was one of those guys you knew probably pissed off his traditional Asian parents more than once.

Case in point: Justin had walked away from a career in law to take a Trust & Safety role on Beth’s customer support team.

It had been a long day. I was overworked, stressed, and suspicious of his visit. It was just me in the office cleaning up one afternoon.

“Hey man, what’s up?” I asked, half interrogating.

“I wanted to help you out. I know you’re a one-man show right now.”

Why did everyone suddenly have an interest in my team?

Customer support had received some anxious emails from onboarding drivers asking where their driver kits were – things were moving fast and people wanted to start making money – he took initiative and visited me in Oakland to lend a hand.

We went back and forth in the middle of the office. Him genuinely offering help, me on the defensive, thinking he too wanted my territory. I can’t recall everything, but I remember:

1) the encounter seemed to leave a bad taste in his mouth, and

2) I quickly realized my error in judgment and felt cringe.

I still feel a little cringe thinking about it today. My bad, Justin.

Years later Justin would return to legal work, including spending several years at Coinbase.

All Systems Are a Go

As Lyft prepped for national expansion, Launchers began leaning on me for support. I was shipping carstaches and available swag for upcoming launches, influencers, local notables, any way to spread the word.

A typical message would look like:

“What do you got in inventory? I need X amount of Lyft swag for [insert city name] ASAP.”

I got special requests which inspired me to research vendors for swag.

Most launchers were fine. A few were pushy.

Then there was Ryan Hupfer – or “Hup.”

Hup joined Lyft, emailed me immediately, and asked for swag:

“I’ll take whatever you got.”

His emails were urgent, but unlike the others, Hup handled comms like a pro. I appreciated it. The approach didn’t feel transactional.

A few days later I heard a commotion in the office and sensed a shadow hovering over me.

“Sup, you Alex?” the voice said.

I looked up. There was a giant white dude towering over my desk. It was Hup. All smiles. We chatted like old friends. He was blowing through town to meet teams before heading into the field. Naturally popular, energetic, gregarious. At 6'6" and 200+ pounds, you noticed when he entered a room.

Fun fact: Remember Myspace? Hup co-wrote Myspace for Dummies. These days he’s founder and CEO of Element Ops.

More with Hup later.

Early Fall – HQ Hot Potato

The first of many organizational shifts hit like a ton of bricks. Drive Team and customer support, both based in Oakland, were relocating to a new office in San Francisco at 185 Clara Street.

Steve mentioned the Oakland lease was still active.

“It’s all yours,” he said.

4,000 square feet. All mine.

The move happened fast. Corey was a beast – coordinating with multiple vendors for moves across multiple offices. The new office was big enough to house the growing company.

Everyone but me.

A part of me embraced the opportunity. Like a teenager left home alone for the weekend: part freedom, part paranoia. A part of me experienced a serious case of FOMO. I worried about being alone on this side of the bay and the company blowing up without me.

Moving boxes showed up, movers followed, and soon the office was mostly gutted – except for my desk, some furniture, and the mostly intact corner office that Steve and Travis used.

And just like that, operations carried on.

Then I got a ping from Elliot Henrikson.

“Don’t cry, motherfucker. We’re setting up a desk for you at HQ for when you stop by 🙂”

I loved my team.

And I made it a point to stop by the new HQ every week.

CUT TO BLACK

🎧 Cue “Hustle and Cuss” – The Dead Weather

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Previous post: Rebel Without a Crew: A Lyft Story – Chapter 2 – Unfuck Everything

Next stop: Chapter 4 – The Everything Team (Part 2) Coming Soon

“Good artists copy, great artists steal.” – Pablo Picasso

Summer 2013

My first day at Lyft was July 1, 2013. I showed up at the Jack London Square office around 9 a.m. and the place still buzzed like I’d never left. Elliot Henrikson, one of the Ops Managers, spotted me and made a beeline–carrying a Nerf gun like it was an extension of himself. Fitting for the Rideshare Wars. Bright, wickedly sarcastic, and surprisingly decent. We’d end up becoming friends.

This time, I ditched the suit. Old polo, jeans, sneakers.

The office was open concept, desks clustered into pods. In the back corner, a medium sized office where Travis VanderZanden worked when he was around. Just outside the office was Steve Schnell’s desk–minimalist, a big monitor. A good view of the action.

Elliot walked me through intros. Everyone on the team was sharp. Everyone had a story. I’d come to learn that weird backstories were part of the Lyft Ops starter pack. I loved it. There was a method to the madness for Steve and Travis’ hiring.

“Welcome to the Drive Team,” Steve said, shaking my hand.

Drive Team. Makes sense.

We traded small talk until Steve paused. “Oh shit, I need to get you a desk.”

“I can stand or find a spot somewhere in the kitchen to post up,” I offered.

“Take mine,” he said, already grabbing his laptop. He disappeared into the office.

Moments later, he returned from the office with a brand-new Apple MacBook Air.

“You cool with this?” as he handed me the box.

Was I cool with it? I’d only ever owned budget Dells. This was my first Apple anything.

“Enjoy your first open experience,” Steve grinned.

“Open experience?”

“Just open it. You’ll get it.”

The iconic white box. The slow slide of the top lid. The laptop revealed itself like a piece of art. Cords were carefully wrapped and tucked in pockets beneath the machine–out of sight. Damn. I got it. Later, I learned Steve Jobs and Jony Ive believed unpacking an Apple product should feel like a ritual–it was an extension of the product itself.

Once I was set up, I had my first real meeting with Steve. The person before me hadn’t worked out. My first assignment? Unfuck everything.

He led me to the backroom. Probably ten by ten, a table and stool, a few spent nerf bullets littered the ground, sides were stacked with boxes of random stuff: aux cables, die-cut stickers, wooden promo coins, and random swag. Pure chaos.

“Take inventory,” Steve said. “We need to know what we have before we launch our next market.”

Hand counting this shit would’ve taken me days. I grabbed a handful of one item, counted exactly 100, and weighed it. Then I used that as a baseline for that item–subtracting the weight of the container and batch weighing the rest to estimate totals. It worked. By the end of day two, the place was spotless. Sorted. Labeled. Counted.

My time as a Hollywood assistant taught me to move fast and stay cool under pressure.

By then, members of the Drive Team started poking their heads in wondering what I was up to. Isamarie Perez, a former tennis player at Stanford, strolled in and nodded in approval while mid-call with a driver. Then Adam Wald, an Ops Manager, asked to use the backroom for interviewing candidates hoping to join the Drive Team since we were short on space. I agreed, as long as it didn’t mess with my flow.

By my second week, Steve called me into the corner office. Travis was there too, hunched over his laptop looking at a spreadsheet. Probably a growth forecast.

“We’re pivoting driver onboarding,” Steve jumped right in. “We’re going to ship onboarding kits directly to new drivers’ homes.”

Travis looked up. “The key is to waste no time between driver approvals and when they get the kit. We need you to find a way to get these to their doorstep when the driver gets approved, so they can hit the road immediately. That day.”

New drivers had to visit local offices for screening and gear. It worked – until it didn’t. It was a process. But physical offices weren’t scalable. Travis went into a mini speech about expanding across the country, and maybe even international.

“This is how we scale driver onboarding,” Travis declared. “And you’re going to drive a big piece of it.”

I was inspired.

“Awesome. How do I do it?” I asked – then immediately regretted it.

Record scratch.

Travis said nothing.

Steve smirked. “Figure it out.”

I emerged from the office with adrenaline pumping a loose list of kitting requirements: carstache, whatever swag we had, an aux cable. Someone at HQ said they would send a few boxes of stuff.

A courier arrived later with boxes of promo cards bundled like bricks and canvas bags to pack items in. But no blueprint. Just parts.

It was late afternoon at the office so I cracked a beer and sat down at a table near the kitchen. Everyone else was chasing leads or closing drivers. I was the odd one out, building something no one could fully picture yet.

I chatted with Mike Diaz, a member of the Drive Team and former manager at Wells Fargo, and asked him about his MacBook unboxing. I was curious. He loved it. Then I caught a glimpse of my MacBook box, which I hadn’t gotten around to throwing out, and instead used it to prop up my monitor.

Might’ve been the beer. Might’ve been the MacBook box staring at me. Either way, I had an idea.

What if I built a driver kit that could deliver an open experience? What would a Lyft open experience look like?

It’d probably be scrappy yet thoughtful. Personal. Not transactional.

If I learned anything from Robert Rodriguez’s book, Rebel Without a Crew, it was this: use what you have, and use your creativity to make it work. Worst case scenario, you practiced making something and could add it to a portfolio of experience.

Steve became a kind of startup Yoda without realizing it. I’d pitch something, and he’d point me toward a tool or resource. That’s how I discovered ULine.

Side quest: If you’ve never heard of ULine, you’re missing out. It’s like the Costco of business operations. Need boxes? Office supplies? Warehouse shelving? A 55 gallon steel drum? They’ve got it. Order by 6pm, get it the next business day.

It saved my ass plenty of times.

I sketched out how I wanted the box to look. It had to have tabs to close the box, rather than flaps. It had to open in a way that revealed the carstache to the new driver. Then I went onto ULine and ordered a bunch of samples. The next day I tested about a dozen kraft mailers. Too flimsy. Too corporate. Too loud. Finally, I found one that struck the right tone: simple, sturdy, human.

No pink or teal boxes. That was too on the nose. I wanted this to feel like it came from a friend. The shipping label on the top left. A Lyft die cut sticker on the bottom right. A circular piece of clear tape over the tab to seal it and make it look hand-packed.

I secretly wondered if someone would film themselves opening it the way people did with Apple products.

And someone did.

Inside, the fuzzy carstache folded on its side. Three canvas bags tucked into it–promo cards, aux cables, stickers.

On top, a square shaped card with FAQs and safety tips. I initially didn’t want this on top because I felt it ruined the reveal of the carstache, and was overruled. Had it been up to me it would have gone beneath the carstache – but safety first – I get it.

Was it perfect? Fuck no. But it worked.

MVP. Ship it.

Steve gave me room to run. Travis backed the plan. Creative sent assets but never got in the way. I built it my way.

The first shipment went out to about twenty drivers. I built them all myself. I scheduled a UPS pickup, then watched the driver haul off the boxes on his dolly. Felt a wave of pride. I’d gone from cleaning out a messy closet to launching a scalable system.

I cracked a beer from the office fridge.

Elliot joined me. “Fuckin’ aye, man,” he said.

Fuckin’ aye.

I took a long drag. Savored the moment. Then it hit me.

“I’m gonna need more help.”

That driver funnel wasn’t slowing down. And neither was I.

CUT TO BLACK

🎧 Cue “Feelin’ It” – Jay-Z, feat. Mecca

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Previous post: Rebel Without a Crew: A Lyft Story – Chapter 1 – Hollywood, Hondas, and Carstaches

Next stop: Chapter 3 – The Everything Team (Part 1)

I always wanted a career in Hollywood. My desire to become a Hollywood producer started the summer after 7th grade, watching Independence Day on opening day – it was a religious experience for me. There I was, watching Randy Quaid’s character, Russell Casse, a washed-up crop duster and town drunk, someone even his kids didn’t respect, redeem himself in the most heroic way imaginable. He flies his F-18 straight into the belly of the city destroyer spaceship.

“Hello, boys… I’M BAAAACK.”

The spaceship explodes. The crowd in the theatre erupted. Humanity wins.

In that moment, the joke became the hero. The build up to that scene still gets me, even today.

Cut to credits. One of the names on screen: Dean Devlin – Producer.

What did a producer do? I knew what a writer and director did. I later learned that a producer oversaw all aspects of filmmaking: from idea to release. Part project manager, part facilitator, part magician.

Side note: I actually talked my way into an internship at Dean Devlin’s production company right after landing in LA and started grad school. Maybe a story for another time.

Cut to the present.

Summer of 2012.

It was a scorching day in LA. I stood in the cracked parking lot behind my Hollywood apartment as a stout Mexican dude in worn coveralls poked under the hood of my 1995 Honda Accord, Betsy. My first car. A hand-me-down. She’d lasted longer in LA than I expected.

“No A/C, transmission’s done, radiator’s cooked… but the interior’s clean” he chuckled.

He was right – the interior was immaculate.

“I’ll give you $500 bucks.”

Sold.

He wrote me a check, backed up his tow truck, hitched the car, and drove off. Betsy would live out her days in a pick-n-pull yard somewhere in the San Fernando Valley. The check felt heavy in my hand.

I was working as an hourly contractor at Warner Bros., Hollywood’s top-grossing studio at the time, but still living paycheck to paycheck. My grocery budget was designed to stretch $1 a day, thankfully there was a Food 4 Less and a Dollar Store nearby. I wasn’t doing Elon’s challenge for the story – I was just broke.

I glanced up toward the Hollywood Hills. My apartment complex sat near Melrose and Vine, behind the Pavilions. My neighbors and I nicknamed the complex “the DMZ,” short for the Demilitarized Zone. The complex had a peaceful courtyard where we would congregate every evening and that shielded us from Hollywood’s chaos. I could see the Hollywood sign from the lot. That day, it felt farther away.

Without a car, I started taking the 222 bus to work. And weirdly, I liked it. I met other WB workers: the other car-less assistants, security guards, facilities staff. People grinding. People like me.

I applied to every open entertainment-related job that I could find. At Warner Bros. alone, I submitted 120 applications in a year. I even knocked on an HR manager’s door when I saw a job I wanted. It annoyed them, but I didn’t care. I was hungry. Literally.

One day in August, on a bus ride home, I spotted Chris, an HR guy from the building I worked at. We’d interacted a few times. Always pleasant. I waffled for a few minutes before mustering the courage to get up and sit closer.

“Hey, Chris, any advice on landing a full-time role? I’ve applied to just about everything.”

I laughed after saying it, half joke, half cry for help.

He gave me a look and smiled. He knew. HR knew.

We started chatting. He told me he’d studied theatre at UC Riverside. Done some stage work. I shared my story too.

As we approached my stop at Hollywood and Vine, he left me with something I still think about:

“You don’t want to get 10 or 15 years into your career only to look back and realize you never did the thing you really wanted to do.”

It wasn’t what I wanted to hear, but he was right.

“You want to produce? Go produce. Make anything. Then someday, they’ll find you.”

Fall of 2012

By the end of October, I’d moved out of my 360-square-foot Hollywood apartment and headed north. I split time between my brother’s couch in San Jose and my old bedroom in Stockton.

Betsy II, my next hand-me-down, was a 2002 Honda Accord. Still had transmission issues, but she had A/C. Light years ahead of the original.

My mom suggested I help my stepdad, Gerardo, start his new business. Years earlier, she’d bought a 4,000-square-foot former grocery store on Main Street in East Stockton – scooped it up cheap after the real estate bubble popped. She grew up in a small town in Mexico, worked in the fields of the central valley in California, raised two kids on her own, and built a nice portfolio of real estate. She’s a survivor in every sense of the word.

The building sat empty until my stepdad – a trained electrician turned tortilla maker – started renovating the building’s interior by himself.

I helped with permitting and random odd jobs. Gerardo had been collecting old machine parts for several months. One day we jumped into his old pickup truck and drove out to some guy’s property in rural San Joaquin County. We picked up these big, greasy chunks of used machinery. At first glance, they looked like junk.

I was skeptical. “How useful can these be?”

When we brought the parts home, Gerardo pulled them apart, cleaned them up, and rebuilt them like he was assembling a gaming PC. Before I knew it, he had custom built a corn tortilla machine from scratch. Anything he didn’t need, he sold off.

The man’s a self-taught engineer. I was like his non-technical co-founder, mostly bringing the pizza or donuts, but proud all the same.

A few months later, Mi Canasta Tortillas opened its doors. Business was slow at first before building a following, but I got to be a fly on the wall for something real. Something we built.

Early Summer of 2013

One Saturday night, I visited my cousin Ivan in San Francisco. He lived in the Mission and took me bar-hopping. The neighborhood had my kind of energy and is still one of my favorite places I’ve ever lived.

As we left Zeitgeist, he walked me to the 16th Street BART station. That’s when a car with a pink fuzzy pillow strapped to the grill pulled up across the street. I stopped and watched as someone climbed in.

“What the hell is that?” I asked.

Ivan shrugged. “Some new taxi service with an app. They’ve all got those pink mustaches.”

The next morning, I googled “pink mustache taxi” and started digging.

I eventually landed on a job board and applied for an Office Manager role. Fuck it – I’d helped manage a busy VP’s office at WB and figured this would be a piece of cake.

A few days later, I had a phone screen with a recruiter named Helen. She mentioned that the Office Manager role was filled, but told me about an unlisted opening for a Shipping Lead role.

“I think you’d be great,” she said. “Come in and meet the team.”

I threw on my black suit from Express, and drove out to Jack London Square in Oakland, where the Lyft Ops team was based.

I walked in and immediately bumped into a tall guy in a headset–Luke Greenwood–chatting with a potential new driver. The place was buzzing. There were about a dozen other people in startup casual attire, all in headsets, talking a mile a minute. It felt like a cross between a college dorm and a boiler room. A world away from the polished studio lot.

Helen emerged from the fray, greeted me, and led me through a maze of giant cardboard boxes stacked like a giant fort – each one filled with a few dozen bright pink carstaches. This fort took up half the office. She guided me to a tiny conference room behind the wall of boxes. Inside there were two chairs and an Ikea desk. I loosened my tie.

I interviewed with two people: Stephen Schnell, VP of Ops, and Travis VanderZanden, COO.

First up was Steve–Hoodie. Ball cap. Easy smile. Beard. We hit it off like buddies. Good cop.

Near the end of our conversation, he asked,“Hey, have you ever shipped anything?”

“Like, mail?” I replied.

“Yeah, we’re probably gonna ship a lot of packages.”

I had. Kind of. At Warner Bros., I’d handled plenty of shipping: brand decks, scripts, merch. Plus, I ran a little eBay side hustle in grad school–buying discount toys, shoes, and Nike gear from outlet stores and flipping them for a markup. That seemed to impress him.

Then Travis walked in.

Button-down shirt. Styled hair. Cool and polished. All business. Bad cop.

He scanned my resume for what felt like a few minutes.

Then:

“What makes you think you’re qualified for this role? You have a master’s in Film & TV Producing and zero tech startup experience.”

I paused. Then I just went for it.

“Film producing is just like entrepreneurship.”

He leaned back, listening.

“You start with an idea. Then it’s your job to bring it to life. That means gathering the right people, managing resources, solving problems, seeing it through.”

I probably rambled. But I wanted him to get it.

When I finished, he stood, shook my hand, and walked out.

Helen popped her head in and smiled.

“So… what do you think?”

I walked out with no real idea of what the job even was.

“It seems like a great opportunity. I’m excited to hear the next steps.”

She laughed and pointed at the wall of boxes with pink fur poking out around us.

“Things are going to be moving really fast around here. I’ll chat with Steve and Travis.”

Everyone in the office seemed in on the joke – except me.

The next day, I got the call. I was officially Lyft employee #63.

I didn’t make it in Hollywood.

But I was about to help build something that might just move the world.

CUT TO BLACK

🎧 Cue “Sabotage” – Beastie Boys

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Previous post: Prologue: How a Hollywood dropout found his ride through the early days of a unicorn startup.

Next stop: Chapter 2 – Unfuck Everything

I’ve carried my story from Lyft with me for years: scribbled notes, half-finished journal entries, photos, vivid memories of a wild ride through the early days of a unicorn startup. Lately, I’ve felt the urge to piece it all together and share it – not just out of nostalgia, but to remember what it was like to build something from nothing.

Let’s start at the end…

October 30, 2014

The building at the corner of 19th and Harrison was Lyft’s stronghold at the peak of the Rideshare Wars. A 67,000-square-foot, three-story fortress nestled in the Mission district. Sure, it paled in comparison to the Death Star building that Travis Kalanick’s Uber called home over at 1455 Market, but it was a fitting headquarters for the alternative to Uber – the "friend with a car" brand that Lyft embraced.

I will always love the Mission. It was my home for 5 years before moving in with my now wife and relocating to Lower Nob Hill. Lyft HQ was a short walk, and an even shorter Lyft ride, from my apartment at 16th and Dolores.

I got to the office around 8 a.m. that day, later than usual. A few people were milling about – the ones who worked all night and clearly never went home (startup life), and the well-rested cool kids trickling in from morning yoga or spin class. I hadn’t started my yoga journey at this point, though I probably should have.

I wore J. Crew button-downs like they were going out of style, paired with Levi's jeans and New Balance shoes. If it got cold, I’d throw on one of my many Lyft hoodies. I now had spending cash, so I upgraded my wardrobe. For me it was stylish yet comfortable, just the way I like it.

At this point, the company had 400+ employees – a mind-blowing number considering a year earlier we had just cracked 100. We had cycled through several HQs in the past 18 months, outgrowing each space like a weed. Every week, I saw more new faces walking around the office with shiny MacBooks, fresh swag (likely sourced by my team), and eager smiles.

I didn’t know most of them, but they usually knew me. Or at least knew of me.

An interaction would go something like:

"You’re the shipping guy, right? I’ve heard all about you."

When I was hired, my official title was Shipping Lead, but I quickly changed it the day everyone was issued business cards. (More on that in a later chapter.)

Honestly, I never liked being known as the "shipping guy." I felt like it oversimplified my contributions to Lyft’s growth. My role wasn’t just shipping – it was company-building and running a logistics operation.

I probably spent too much time at the office. I ate breakfast and lunch there daily, sometimes dinner, and often worked Saturdays. Sundays were my day off, but I was always thinking about the upcoming week. Great for my grocery budget, not so great for my social life.

Fake startup influencer types will tell you it’s 24/7/365 or some bullshit – and while it can be, it’s not sustainable. Especially if you’re busy chasing engagement by writing trite social media posts full of self-aggrandizing platitudes.

I was burnt out. I needed a vacation.

During my time at Lyft, I had taken just one day off, to attend my dad’s funeral back in Stockton. I remember taking my work laptop in my backpack and periodically checking in during the family gathering. I wasn’t super close with my dad but his death still impacted me, and in retrospect, I should have left the laptop behind and taken time to decompress.

I should’ve booked that Virgin Atlantic flight to London.

That morning, my fuel was pour-over coffee with creamer and sugar, paired with toast and avocado, a hard-boiled egg or two, and a banana. Kudos to Corey Lambert, the best office experience manager in tech.

One of the many skills I picked up at Lyft was the art of the pour-over, thanks to Colin Frolich. A former Starbucks marketing guy, Colin taught a few of us the craft. It became a nice little ritual where I could focus on the details of my morning nectar – very zen, very tasty. These days, Colin is the founder and CEO of Placemate.

I got to my desk and flipped open my laptop. I had been working with a potential new partner to reduce the cost of our newest onboarding kit. For context, anyone who wanted to be a Lyft driver had to complete a background check and identity verification. Once approved, they were shipped a driver kit: a pink carstache, Lyft stickers, FAQs, and other essentials. These kits were fun to build.

I had sent samples to a startup run by two young guys who had likely realized we were shipping truckloads of these kits weekly. They claimed to have better pricing. Okay, bring it on!

By then, I was getting more cold calls from companies wanting to partner with Lyft in some way: as a supplier, a 3PL, or a tech solution. We were a huge deal now. Gone were the days when I got laughed at and hung up on.

I’m the captain now, bitch.

Their proposal projected savings in the neighborhood of $3 million annually. Some weeks, we were shipping 2,000-3,000 kits. Crazy to think that a year earlier, I was assembling these kits by myself in a back room at the old Oakland office.

I sat back and reflected on my journey on the Drive Team, what we early employees called the OG Ops team. We grew up together and helped take the company from obscurity to national attention. Jerry Seinfeld was once photographed wearing a pink mustache for a magazine shoot.

Even my mom was like, “I saw your company on TV.”

Hyper-growth is no joke, folks.

I glanced up at a small sign on the back of Matt "Disko" Earnest’s monitor.

It read: "I’d take a Nerf bullet for you."

Disko was one of the original San Francisco Lyft drivers, a legend in the community, back when they decorated their cars to reflect their personalities. His car was a full-blown DJ setup: intelligent lighting, a karaoke machine, and turntables. The phrase on his monitor embodied the cheeky attitude many of us early Lyft employees adopted during the Wartime era of Rideshare. The days were long. The work was intense. It was fun, but also brutal. Yet we always had each other’s backs. These days Matt is a Handyman and Council Member in the town of Mountain House, just outside of Tracy, CA.

Then came the message that would change everything.

A ping from my manager, also named Matt: “Hey, do you have a moment to meet downstairs in such-and-such conference room?”

I furrowed my brow and took another sip of coffee. I glanced at my coordinator, Karynn, but didn’t say anything. Too early for bad news, I thought.

Matt had been assigned to me after the abrupt departures of my original bosses, Steve Schnell and Travis VanderZanden. Someone said Matt was a rockstar. Apparently, he tightened up operations at a previous company.

Steve and Travis would eventually land at rival Uber.

I made my way downstairs past a wall of employee photos: group shots, candids, memories. A warm touch to HQ.

I walked into the conference room, laptop under my arm. Kelsey from People Ops was already there. Her face was unreadable.

Remember that scene from Goodfellas when Joe Pesci’s character Tommy DeVito gets whacked? Felt kinda like that, except one of the walls was covered in pink fur.

I took a seat.

Matt sat in front of the pink fur wall. It felt like an episode of Silicon Valley.

"We no longer have a place for you on the team. Today is your last day," he started.

Record scratch.

"Can you give me 24 hours to find another team? I’ve seen others that were given that opportunity when teams and roles were eliminated." I fired back.

"We asked. No one wants you," Matt shot back.

No one wants you.

Oof.

Matt mumbled something about performance, but the only example he gave was a delayed email reply from weeks ago. It was also the first time anyone had raised a concern about my performance.

“There’s no longer a place for you on this team. Sorry.” He finished.

Truth is, I should’ve seen it coming. When the new VP of Ops, Woody, dismissed all of my work and told me that I’d have to start from scratch under his regime, it was a sign. People were getting pushed out. I wasn’t the only one.

Kelsey slid the separation docs across the table on cue. I examined them.

"Can I get a moment alone, please?" I asked.

Alone in that cold conference room, I accepted my fate. The company I helped build no longer wanted me. Lyft had given me a chance to go from zero to one, professionally and personally.

The ink on John Zimmer’s signature looked so fresh.

I had been unceremoniously dumped by one of the hottest startups in tech.

I was sad, but also relieved.

Let’s go back to the beginning.

FADE TO BLACK

🎧 Cue “Let’s Stay Together” – Al Green.

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Next stop: Chapter 1 – Hollywood, Hondas, and Carstaches

Today, I got an email from a student at a prestigious university out east. The classic cold outreach: job referral request, neatly packed with professional accolades, educational background, and a dash of personal flair to keep it interesting. As someone who’s sent their fair share of these emails, I get it. That’s why it bothered me enough to draft this stream-of-consciousness essay.

There was clearly a template involved because the blanks meant for personalization were in bold–the email equivalent of seeing a CGI actor in one of those body suits covered in tiny motion-capture balls. It just makes the whole thing feel... artificial.

Surely, they sent this to tons of people at my company (wild guess). I know this because it was sent to my old email LDAP. For the uninitiated, LDAP stands for [checks Google] Lightweight Directory Access Protocol—a digital phonebook for your company’s internal systems.

I actually requested a vanity change shortly after starting at Block. My first assigned handle was first-initial-plus-last-name, which is cool, but didn’t quite have the right ring to it. So, I pulled a Timberlake and requested to drop the—or in this case, my first initial. Any email sent to my old handle still forwards to my new one. But I digress.

No shade to the person—kudos, actually, for doing the research. But I was expecting more. They did the work, but they didn’t sell me. I mean, they even figured out one of Block’s email LDAP naming conventions—but then fumbled the rest. Have I ever answered a cold email? Yes, but rarely. I’ve been in your shoes, young buck. I get you more than you know—but you gotta do it right.

Look, I get it. I’ve been there. I’ve sent cringe-worthy cold emails I’d rather pretend never existed. But the ones that worked? They weren’t perfect—they just made the person on the other end feel like a human, not an email template fill-in-the-blank.

In this case, the person asked about a role that wasn’t on my team, wasn’t a role I was hiring for, and wasn’t even remotely connected to what I do. And to top it off, they closed with (paraphrasing here): If this isn’t you, please forward it to the hiring manager :)

Okay… thanks?

I need to feel like you actually took the time to get to know me, friend. Come at me direct. An easy (yet not foolproof) opener could be:

Hey Alex, I don’t know you, but my name is… I’m studying [thing] at [fancy private university with ivy bushes n’ shit]…

I see you also went to [same college]… I see you worked at… Do you actually parler français like your LinkedIn says? Did you know so-and-so at such-and-such? You’re from Stockton too??

Not gonna lie, that last one would almost certainly get a response—even if it was just a call to say, Hello, congrats, you made it out of Stockton.

A part of me wanted to rewrite their cold outreach email for them and send it back so they could use it on their next wave.

This whole thing got me thinking: is cold outreach an art or a science?

I’ll probably need to figure that out.

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