Unbundling Travel and Supporting Gig Workers

On platform marketplaces, gig workers, and the phenomenon of travel goods that don't transport us anywhere at all


You are receiving this email because you subscribed to 4 Cool Jobs. My name is Lea 👋. I started writing this because in my 20s I've watched all my friends try to work at the same 6 big companies. Bad news: passion nor probability work that way. Good news: cooler opportunities are elsewhere.

4 Cool Jobs is about the elsewhere in tech and the trends behind it.

After I sent out 4CJ last time, my mom texted me and said "I haven't left my house in 5 months. Will you do one on travel?"

So here we are. I'm going to talk about companies that are changing the structure of the travel economy 🚗✈️🌅.

This transition is summarized by a tweet from Li Jin, an a16z alum:

We're moving toward economies where workers, “unbundled” from organizations, connect to their consumers through platforms to provide them goods directly: the gig economy.

In some industries, this is convenient; in others, it’s exciting. Individually-produced goods have magic 🧙‍♀️to them, a sense of self embedded in product, that mass-produced goods don’t.

In the travel industry, that magic is definitional. If a good or service doesn't contain a sense of self, it can't contain a sense of place. The exchange of that good can't meaningfully convey story and specificity and belonging.

It will sell travel that doesn't really take us anywhere at all.

That sums up the "Travel-via-Organizations" landscape of the past fifty years. Corporations specialize horizontally in one aspect of the travel sector—like transport or lodging or tours—to scale even without modern tech. They hire workers from disparate places who help to create services in specific places, such that the services in the places don't have much to do with the places at all:

You can replace the blue block with any international hotel company or travel agency or tour company.

Of course, there has always been a better option: real people in Berlin who have real Berlin homes that they'd like to rent out (or real Berlin tours that they'd like to give, etc).

Enter the internet and suddenly we were able to build what it took to bring both sides of the market together:

  1. A connection mechanism: the ability for local property owners to find travelers looking for lodging, and vice versa.

  2. A reputation mechanism: in the absence of big-brand reputation, the ability for travelers to quality control check and trust the lodging options,and vice versa.

AirBnb et als said "we can do that" and platform economies were born.

The lodging market in Berlin now can more like this:

This unbundling brings several good externalities: a more authentic experience, more efficient urban space usage, and more personalized product-market fit.

Uber unbundles transport, Daytrip unbundles local travel, WithLocals and Evaneos and Questo unbundle tours. WandamapsTravello, and so on.

The fact that we can more easily buy travel things that actually take us places is exciting, but for the unbundlers themselves—all the hosts in Airbnb Berlin and gig workers elsewhere—there are new challenges.

Holiday Inn and Rick Steves have market analysts optimizing prices and professional graphic designers making webpages and big corporate insurance policies to clean up spills. Behind a person leasing their studio is just...the person leasing their studio.

Person leasing their studio has a great, even superior good to provide. But they aren't a marketer or an analyst or a photographer or a designer. How should they price? How should they advertise? How will they find someone to clean when they aren't around?

With these needs, a secondary market emerges, focused specifically on providing support to unbundlers.

This week: 4 companies in the green block that provide services to the unbundlers.

Two points of note:

  1. Look for this pattern to occur elsewhere. As the first layer of a market shifts to unbundled good/service provision through platforms, new businesses pop up to develop a tech stack for unbundled good/service providers. Anywhere things will unbundle, the unbundlers will need support: AirBnb hosts, Uber drivers, GrubHub workers, Etsy artists. As unbundling moves into knowledge markets and value-added goods, the need and sophistication level of the support will increase: Notion and Roam, for example, which I talked about here.

  2. As things become unbundled horizontally, there will be the biggest pull ever to re-bundle them vertically. There are some people who are are zealous enough to sift through hundreds of AirBnB listings, local tour offerings, and transportation choices— but there will be others who look at that menu and groan. Too many options! So we will have to rebundle again. This is already happening a bit and doesn't have to bring back the annoyances of the organization-dominated travel landscape: example 1, example 2.

The jobs:

  1. Glimpse

Glimpse facilitates product placement in Airbnbs.

In 10th grade I took a class called media lit. In it we learned about ET and Reece's Pieces. The story is this: Steven Spielberg's production company asked M&Ms if they wanted to pay to have ET (the alien) eat their M&Ms. Mars (who owns M&Ms) said no—they thought people wouldn't want to eat a candy that was eaten by an alien. They were wrong: competitor Reece's Pieces took the deal and their sales increased by 300%. ¯\(ツ)/¯ The moral of the story is that when people like something, they want to hang onto things that remind them of that experience. Airbnb hosts are a natural fit for this: if you have a fun romantic evening at a getaway cottage on the beach, you might want to take some of the coffee you had home with you. Glimpse sets it up so that you get the coffee—or candles or furniture or mattress— and the host gets a cut of the proceeds. It has the potential to become an additional revenue stream.

They aren't hiring yet, but are backed by Y Combinator and were recently profiled by techcrunch. Look out for career opportunities on their site or on Angels List.

  1. Dumpling

Dumpling helps gig workers launch independent businesses.

Dumpling is made for gig-economy grocery shoppers, which you may or may not encounter while traveling, but they are such a good example of the enable-the-unbundlers trend that I had to include them. Basically, if you're a gig economy worker and you rely on that gig for a good percentage of your cash, you're losing a significant amount of money to platform fees (and operating in a hyper-competitive environment😲). You also maybe provide a super good service and want to capitalize on the relationships you build. Dumpling is the toolkit that helps you start your own spinoff service: they help you move from Instacart deliveries to a providing a suite of needs for a selection of recurring customers. If Dumpling is successful, they can extrapolate into other realms and move gig economy workers from platform-dependent to fully fledged LLCs.

Dumpling is hiring mobile and backend developers.

  1. BeyondPricing

Beyond Pricing helps your Airbnb host set their prices.

Corporations have entire teams of analysts dedicated to locating the perfect intersection of demand and supply so that they eek all the possible dollars. Those dollars might mean a lot to some person leasing out their apartment in Berlin. And how can that person get a grasp on the comportment and budget of the hundreds of people from around the world, from the US and Asia and Australia, the families and single travelers and friend groups, all trying to place to stay? It's tricky. They can always price relative to other rentals, but demand changes frequently. BeyondPricing helps hosts maximize revenue and occupancy by analyzing localized market data and auto updating rental prices daily (they have Airbnb/Homeaway/Booking/etc integrations).

They are hiring from entry-level to executive-level, in customer success, software engineering, and HR.

  1. Sherpashare

Sherpashare helps ride-share drivers get the most out of their time.

Many of the services above boil down to this: in the platform economy, the goods and services provided are personal. For the workers, the margin they make on their goods makes a huge and personal difference as well. BeyondPricing (profiled above) ensures that Airbnb hosts don't leave money on the table; Sherpashare does the same for Uber/Lyft drivers. Their app is a little mini tech stack that includes financial management, tax planning, benefits, analytics, real-time route-optimizing advice, expense tracking, and exclusive discounts. It has a surprisingly beautiful UI (a large space of users to cater to) and has a mission to enable the best returns on independent work.

They are hiring in product design and engineering.

Until next time,



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