Per My Last E-mail #10

Substack Serendipity, Couriers, Cashouts and Buybacks, Value Hacking, Cowboys

Hi Friends 👋,

Happy Monday!

🎉 #10 🎉

When I begged a lot of you to sign up for a newsletter I had to do for a writing course I was taking, I didn’t expect to still be writing by Per My Last E-mail #double-digits, but here we are.

Knowing that I am going to be writing to a growing number of you each week has made me more curious, a more active reader and listener, and even a more organized link-gatherer/note-taker. It has sparked interesting conversations with friends on topics we didn’t realize each other cared about, and it has opened up conversations with new people I’ve never met in real life.

This weekend, a New York Times Editor, Tim Herrera, asked his Twitter followers “was anyone on their college debate team? pls DM, i have many questions (this is serious pls reach out lol)".” Pamela, who was in my Write of Passage course and subscribes to this e-mail (thanks!) replied to Tim and mentioned that I debated.

Tim reached out to ask why people speak so fast in debate, we got into a conversation, one thing led to another, and he wants to come to the first NYC Debate Club debate in September.

That’s just the most recent example of the serendipity that has come from writing this. As silly and self-promoting as it makes me feel to hit send every week, it has been a really positive experience. (This type of positive experience may be why Substack, the software I use to write and send this newsletter, raised $15.3 million from a16z last week.)

So 10 weeks in, I’d love your feedback:

  • What do you think I should be writing about more?

  • What do you think I should be writing about less?

  • What type of content have you enjoyed the most?

  • Has anything you’ve read in these newsletters taught you something new that stuck with you, or changed your perspective?

Somehow, we’ve averaged an 85% open rate over the first 9 e-mails, and I’m interested to see how open rates and clicks evolve as subscribers continue to expand beyond just people I know and who feel obligated to open (thanks, y’all ☺️). I would really appreciate it if you forwarded this e-mail to someone you think would enjoy it, or share this subscribe link.

On to the content…

Links & Listens

My Frantic Life as a Cab-Dodging, Tip-Chasing Food App Deliveryman by Andy Newman in NYTimes

About 6 months after launching Breather in NYC, I got a call from the guys who ran the company that cleaned our spaces. They had just gotten acquired, and in a week, they would no longer be able to work with us. I panicked for a second, called my mom, and then came up with an idea.

Uber had just launched UberRUSH, an on-demand bike courier service, a month or two earlier, so I reached out to Uber’s NYC GM, Josh Mohrer, and asked: would your couriers be able to clean Breather spaces? Somehow, Josh agreed, and we worked with the Uber team to get buy-in from the couriers and get our very own “Breather” slider in the Uber app, through which I could see the subset of available couriers who were willing to clean our spaces.

In order to handle multiple simultaneous jobs, I set up a second phone number and a second Uber account, and we were off to the races. Every day for 6 months, I woke up around 6am, when our spaces opened, and started hailing UberRUSH couriers to clean our spaces. I dropped the pin at whichever address needed to be cleaned, found the nearest person, and then texted something like:

“Hey! Ok this is weird, but there’s no delivery. This is a Breather cleaning job. At 7:00am, please go to suite 611, knock on the door to make sure the client is no longer in the space, and if it’s empty, enter 348274# on the keypad. Once you’re in, there is a kit with supplies and instructions under the couch. The next client gets there at 7:30am, so please be thorough but quick. Let me know if you have any questions. Thank you!”

I did this thousands of times. Apparently I was UberRUSH’s #1 customer. Legitimately. You can ask Puja; I would be at dinner, seeing a movie, at the beach, in the middle of a meeting with a landlord, 6am or 11pm - if there was a reservation ending, I was on the Uber app hailing a courier, and then texting a spiel like the one above.

Over time (and this is why I’m telling you this story here), I became friendly with a lot of the couriers. To the point that I could just text “Yo! Code is 402832#, next res is at 8:30. How you doing?”

Through my relationship with one guy, Sam, I learned just how crazy and dangerous this job can be. Sam, aka Turtle, was about 25 when he started working with us, gregarious, and the most fearless biker I’ve ever seen. When he wasn’t couriering, Sam raced bikes on the weekend.

Given the nature of the job, Sam and I texted multiple times a day, every day he worked. And just about once every couple of weeks, Sam would text me something like, “Yoooo I’m not going to be able to complete that job, I got hit. I’m at the hospital, I’ll be alright,” with a couple of gruesome pictures of scrapes, bruises and cuts attached for proof. He broke at least three bones while we knew each other, and as soon as he was even semi-healed, he got back on his bike to do more jobs to pay his rent and fund his passion for bikes.


I tell you all of this because yesterday, Andy Newman of the New York Times wrote a piece discussing the delivery cyclists powering products like DoorDash, Uber Eats, and Postmates. In it, Newman highlights the risks of the job:

And there are risks. Nearly a third of delivery cyclists missed work because of on-the-job injuries last year, one survey found, and at least four delivery riders or bike messengers have been killed in crashes with cars this year

Maria Figueroa, director of labor and policy research for the Cornell University Worker Institute in Manhattan, called the food couriers “the most vulnerable workers in digital labor.”

While we ultimately hired many of the couriers we originally worked with through Uber, including Sam, paying them good wages plus benefits, many delivery cyclists can end up making minimum wage or worse, with unpredictable tips and unpredictable delivery flow, all while putting themselves at risk.

But the wage conversation is another discussion for another time. For me, this article is a good reminder to appreciate the people behind our deliveries and the risks they take to make a living.

(Thanks to Mike Madonna for the recommendation; turned this section into a post here.)

🏢 WeWork Co-Founder Has Cashed Out at Least $700 Million Via Sales, Loans by Eliot Brown, Maureen Farrell, and Anupreeta Das in WSJ

🏨 Oyo founder triples stake with $2bn share buyback by Benjamin Parkin in FT

If you’ve been reading this newsletter for the past 10 weeks, you know how much I love a good Adam Neumann article. What was fascinating this week was that two days after the WSJ reported that Neumann had cashed out over $700 million from WeWork, the FT reported on the opposite happening at another real estate startup, Oyo.

Oyo, an Indian company founded by now-25-year-old Ritesh Agarwal when he was a teenager, is already the largest hotel chain in India. “The company’s model hinges on turning existing hotels into franchisees and promoting them through an online booking platform, using technology to fill rooms as efficiently as possible.”

On Friday, Oyo announced that Agarwal is buying back $2 billion from VCs Sequoia and Lightspeed, tripling his stake in the $10 billion company from 10% to 30%. (For context, when I was 25, I ran a party bus from New York to Avalon and back.)

If I had to choose between backing a company whose founder has cashed out nearly a billion dollars and one whose founder bought back $2 billion from its investors, I would be backing Oyo.

🤑 Value Hacking and How to Avoid the Fake Growth Epidemic with Mike Maples on Venture Stories [Podcast]

Mike Maples is a VC at Floodgate Capital who has been on Forbes’ Midas List since 2010 for investments in companies such as Twitter and Twitch. Trying something new. Instead of writing my thoughts in this e-mail, I’ve taken notes on the episode that you can check out here.

📈📉 Paradigm Shifts by Ray Dalio

Ray Dalio is really smart. In this piece, the billionaire founder of Bridgewater Capital lays out the paradigms that have defined each decade since the 1920s (ie. 1920s = “Roaring”: From Boom to Bursting Bubble, 1930s = Depression, 1940s = War and Post-War, etc…), and shares his well-researched thoughts on what will cause the next paradigm shift and what new paradigm will emerge in the 2020s.

TL;DR: Buy Gold.

💡 Thread on DTC Category Ownership and Expansion by Marco Marandiz

Marco Marandiz now owns the distinction of being the first person to have his threads included in Per My Last E-mail two weeks in a row. Big congrats to Marco.

In his latest thread, he lays out why:

1/ The best categories are flexible

2/ The best founders are solution agnostic

3/ The best companies are ambitious beyond their vertical

His argument lines up with my thinking on Natively Integrated Companies, and is essentially that consumer products are a great way to build a loyal customer base, and the best way to monetize that customer base once you have them is to sell them software and financial services.

What I’m Reading

This past week, I finished Secrets of Sand Hill Road by Scott Kupor. Notes to come, but I recommend that anyone interested in how venture capital works, or in starting a company that will need to raise VC, reads the whole book. One of my biggest takeaways is an old but important lesson: incentives shape behavior. Secrets of Sand Hill Road gives a thorough overview of the incentives that drive VCs, along with definitions and examples of key deal terms, and explorations of how those deal terms can impact real-life situations.

If you’re interested in the topic but are more a listenin’ type, Kupor did a 3-part series on the a16z podcast to go in-depth on the topics covered in the book: How to Understand and Choose a Venture Investor, How to Raise Money from a Venture Investor, and How to Get the Most from Your Board.

In the last Per My Last E-mail, I said that I would alternate between fiction and non-fiction, and here we are a week later, and I’ve already broken that rule. So I’m going to amend it slightly to include narrative-driven biographies and company histories in the “fiction” category.

This week’s read: Cable Cowboy: John Malone and the Rise of the Modern Cable Business by Mark Robichaux. I’m 68% in, and I can tell that Cable Cowboy is going to join Shoe Dog on my short-list of top books about people who built great companies. More to come on this one next week.

What’s Next?

This week, I’m finishing my first follow-up post to Natively Integrated Companies. In Act 2 of that series, I wrote about the fact that only two of the top consumer spending categories had not been taken over by Aggregators: healthcare and education. My next post, out before this newsletter next week (writing this publicly so I actually finish it) will be on a Natively Integrated School.

Thanks for reading and have a great week,



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