Rebel Without a Crew: A Lyft Story – Chapter 4

The Everything Team (Part 2) – The Moonshot That Never Was

Dec 05, 2025

“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.

I know the drivers of both of these cars. Five stars!

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.

aerial view of city at nighttime — Photo by Tyler Casey on Unsplash

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.