- The Remote Life OS Newsletter
- Posts
- The Connection Newsletter 71 - Comeback
The Connection Newsletter 71 - Comeback
The Connection Newsletter 71 - Don’t call it a comeback

Hello!
This is edition #71 of
The Connection
, the weekly email I send family, friends, and future friends (hello!) Glad you're here.
Things week’s articles are mostly about startups, work, and parenting. This closely mirrors my own life these last 7 days, as the latest Reforge programs are now underway. So no major updates from me. Let’s jump right into the articles.
(Want less email? No problem, you can unsub at the bottom. We'll still be friends.)

Work & Technology

There was a lot of doom and gloom coming from Etsy around 2017, when Josh Silverman was brought in as CEO to turn around the company. I remember talking to a few employees about it: projects were getting rolled back, there was a shift in tone, and worries that Etsy was losing its soul.
From a business perspective, things certainly were starting to look bleak: Growth in gross merchandise sales (GMS) had slowed. The wolves (aka activist investors) were pushing Etsy to fix its business or sell itself.
And within weeks of hiring Silverman, the company laid off a quarter of the staff.
Then came the turnaround. The company improved search, payment and checkout, and shipping -- all the things important in an ecommerce company.
Since taking the reins in May 2017, Silverman has moved to improve —the nuts and bolts that build customer trust. Etsy has also managed the difficult feat of increasing the share of each sale that it keeps for itself without driving sellers away.
“Revenue has risen 65% in two years, reaching $604 million in 2018. The company has also been profitable for two years, and the stock is up fivefold during Silverman’s tenure, giving Etsy a market cap bigger than that of Macy’s or Nordstrom.”
What was the approach that launched the comeback?
The CEO describes his mission as doling out tough love. “The core of Etsy is amazing,” he says. “It just needs the opportunity to breathe.”
One of the things suffocating it, he found, was an excess of projects—there were some 800 business development initiatives underway at a company with a staff of fewer than 1,000. Silverman’s team quickly eliminated half of them, including Etsy Studio, an ambitious plan to create a second online marketplace. Among those remaining, the team created “ambulances,” ideas whose paths could be cleared so they could be implemented in weeks rather than months or years.
What happened to GE and Six Sigma, the management style heralded by oracle of GE, Jack Welch?
In early 2000, GE passed Microsoft to become the world’s most valuable company. The conglomerate sold jet engines and mortgages, and reached a market cap of nearly $600 billion.
Today that market cap has sank to around $60 billion.
“Six Sigma could get the company only so far, according to Jim Clifton, CEO of Gallup, the polling and consulting company. ‘Jack Welch was the king of process innovation,’ said Clifton. But when Jeff Immelt took over, he had a problem—there was nothing left for him to Six Sigma.’”
The principles of Sig Sigma ultimately clashed with the values of Silicon Valley: disruption and big swings, innovation over efficiency. In a world of game-changing invention, there was no room at the table for an obsession with efficiency.

In the personal development sphere, there's a lot of talk about not just working, but
working the system. Sam Carpenter’s
is an excellent primer on this.
I really liked how Justin Kan (Kiko Software, Justin.tv, Twitch.tv, Socialcam) put it in this interview with Andrew Chen, when it comes to the system of building a great company:
“I had never asked myself, what is the kind of company I want to show up to work?” There’s a saying that initially, a startup is about building a product that works — that’s the machine. But eventually you have to transition into building the machine that builds the machine — meaning company building, as opposed to product building.
Culture is the core glue that holds everything together, and sometimes a startup idea is so strong that it works regardless of the culture. But it can be even more effective when it works.”
Mike Davidson wrote about his experience working remotely after one year at InVision, an all-remote company with 800+ employees. I loved his summary of remote work, which echoes my own sentiment after working remotely for almost 5 years now:
"Despite what you may read on Twitter, remote work is neither the greatest thing in the world nor the worst. We are not moving to a world where offices go completely away, nor are we going through some sort of phase where remote work will eventually prove to be a giant waste of time. In other words, it’s complicated."
One caveat I’ll add: remote work gives you the option to better structure your life around work. Need to pick up the kid from daycare? You can make it happen. Want more socializing time? Bake it into your schedule. The flip side is you have to take complete ownership of every minute of your schedule, which isn’t necessarily the ideal environment for everyone (sometimes, you just want an office buddy to talk BH90210 with).

In this piece, Zara talks about the frenetic pace of working in China:
Receive several hundred WeChat messages for work. Business plans, legal documents, and due diligence files are sent over WeChat. It is very common for professionals to have tens of thousands of unread messages on WeChat.
It is not uncommon to have back-to-back meetings from morning to midnight, with no breaks in between. We often meet and eat at the same time since there is simply no time for lunch/dinner.
Don’t be offended if your dinner date looks at her phone every 15 minutes during the meal. At virtually every large dinner gathering I have been to in China, there are moments when everyone just falls into silence halfway through a meal and starts replying to WeChat messages on their phones for the next five minutes.
What was her takeaway from all this? Don’t work in China?
On the contrary:
"Although it feels like you are scrambling and hustling from meeting to meeting every day without end, the learning and growing are also happening at a rapid pace. China is one of those places where just being there is an educational experience, and I recommend anyone in tech – Chinese or not – to explore working in China at some point throughout their career."
I really liked this outlook. It’s not for everyone, and it certainly doesn’t have to be for the rest of your life. But there’s a benefit to working somewhere that sets an incredibly fast pace to build a strong foundation in skills and knowledge.
It’s analogous to starting out as a line cook at a busy Denny’s, or working at one of the big four agencies in Hollywood. Once you learn to grind under the greatest amount of pressure, you’re able to make diamonds.

Hims copied Ro’s patient flow down to the stock photo. This was hilarious.
This happens all the time in tech. If a competitor builds something better, there is no shame in copying what works instead of being prideful and maintaining a worse user experience. It’s unfortunate and can be demoralizing to be on that product/design/eng team (who wants to be told “copy our competitor exactly!”?) but I get it.
Honestly, I applaud Hims for it.
At Ro, we consider ourselves to be the most patient-centric company on the planet and, if other people think so too, we can’t be mad, right?
Parenting

Credit: João Fazenda
Takeaways I try to keep in mind for my son:
Let him play
Not everything needs to be driving towards an end goal
Listen. Let him become himself
A 2019 study published in the Journal of Abnormal Psychology found that between 2009 and 2017, rates of depression rose by more than 60 percent among those ages 14 to 17, and 47 percent among those ages 12 to 13.
No longer able to rely on communal structures for child care or allow children time alone, parents who need to work are forced to warehouse their youngsters for long stretches of time. School days are longer and more regimented. Kindergarten, which used to be focused on play, is now an academic training ground for the first grade. Young children are assigned homework even though numerous studies have found it harmful. STEM, standardized testing and active-shooter drills have largely replaced recess, leisurely lunches, art and music.
There are plenty of articles that talk about the growing student debt and inflated university costs. While there are probably a constellation of factors, Caitlin Zaloom pinpoints the inflection point:
The shift began in the 1980s, in terms of a changing political philosophy. President Ronald Reagan’s budget director, David Stockman, said in 1981, “If people want to go to college bad enough, then there is opportunity and responsibility on their part to finance their way through the best way they can.”
When those who argued that college is a private benefit framed it like that, it became logical to say that education should be paid for by the people that it benefits. And so in the 1990s, the vast expansion of loans for higher education began.
For Fun

Louisa Thomas breaks down the forehand, one of the fundamental movements in tennis, and looks at how Roger Federer, Rafael Nadal, and Madison Keys make the move their own.
Deep dives on such a singular element of a sport (or business, or product) are fascinating to me. I love how they show irrespective of the arena or topic, there are always many ways doing it “right” and doing it in a way that’s unique to you.
Thanks for reading!
Last thing: Is there anything I can help you with?
If there's any way I can help out, please let me know. Or if we just haven't chatted in a while, I'd love to hear from you. Just reply directly to this email.




Reply