The Looking Glass: The Stories That Become History
In celebration of some of the women that set the bar for me
Dear Readers,
When I look back on my working life, there are episodes which feel like a bad sitcom, where I acted in such a way that the me-of-today is thoroughly mortified.
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Oh, there are seasons where I puffed my chest, where I played “cool girl,” where I wore the smooth mask of professionalism. There are seasons where I fell apart behind closed doors and locked stalls.
I attribute much of this acting to the stories I was most exposed to — in computer science, in tech, in leadership — the ones where men played starring roles.
It’s hard to be what you cannot see.
In a stroke of enormous luck, I was able to grow my career in an environment that nurtured women, that enabled incredible female talent to grow and thus show me many more ways of being.
In recognition of Women’s History Month, I’d like to tell some of these stories of the women who have set the bar for me.
There are many more stories like these that I’d like to tell, because there are many more people who have left their tints in the glasses of my worldview.
I hope you’ll find yourself inspired by these women, and the many more in our lives that help us see what is possible.
In this issue:
- A story about impact
- What support feels like
- The warm, subtle guiding hand of influence
- Mining the rich depths of an experience
- From the archives: The world needs more CEOs like Fidji Simo
For paid subscribers:
- No new posts this issue, but I will do an AMA this weekend for paid subscribers. Chat with you then!
A story about impact
Nearly a decade ago, I saw Deborah Liu advocate for what seemed like an outlandish idea at Facebook — give people a way to coordinate buying and selling local, real-world items directly with each other.
“Why?” a lot of folks internally asked. “This doesn’t really have to do with friends or deepening social bonds. There are a million other companies doing commerce — let them have their lane and we’ll stick with ours.”
Deb was undeterred. She came from eBay and had a deep understanding of marketplaces, combined with a few years of learning the ropes of Facebook’s social engine. She observed a number of online groups already formed to exchange items; she herself appreciated the efficiency and economy of scoring a great deal or selling things she no longer needed.
Deb is one of the savviest strategic minds I know, and the alchemy of these two experiences yielded a unique insight that a local, peer-to-peer marketplace was a) a big opportunity to create value and b) something Facebook could do uniquely well.
Deb fought hard for this idea. She spoke about it to whomever would listen. Eventually Mark Zuckerberg agreed she could rally a small team of other believers to try out building Marketplace.
Even after some initial traction, Marketplace often felt like an oddity inside Facebook. The team dealt with all sorts of new-to-Facebook issues: messaging and establishing trust among strangers, fighting scams and counterfeits, focusing on privacy and safety, etc, all amidst a tidal wave of many (well-meaning) critiques that argued it was a distraction, or too confusing, or using too different a technology stack, or not fitting into the long-term strategy.
Watching this unfold over the years, Deborah Liu set the bar for me in terms of sheer grit and perseverance. What a fighter this woman is! She and the scrappy Marketplace team quickly experimented and executed to find out what worked. Day by day, the product experience won over more and more users.
One of Meta’s greatest strengths as a company is its deep discipline of focusing on Impact — rewarding not the effort put into something, but the actual results.
It is not about how many features were shipped, how many lines of code were written, how big the “buzz” is, how many failed experiments are clocked, how many haters there are — it is ultimately about the value created for customers.
Deb left Marketplaces a few years ago; last week I came across an article in the New York Times titled: “One Big Reason Gen Z Is Still on Facebook: To Save Money.”
Can you guess what saves Gen Z money, what keeps them coming back to Facebook?
That’s right: Marketplace.
Talk about impact! Hats off, Deb — thank you for this amazing example and reminder.
PS: Deb is CEO of Ancestry, and formerly created and ran Marketplace. She’s a prolific writer and storyteller and you should follow her substack Perspectives and read her book Take Back Your Power.
What support feels like
I have lost track of how many times I have cried in the workplace.
Not because my job sucked or I had unkind colleagues (I’m lucky to have had the best in both), but because I’ve spent half my waking hours working, and have felt the entire scale of human emotions visit me across that period.
I have cried when a task seemed too big, and I felt too small to get it done.
I have cried because I was underslept and overwhelmed after returning from maternity leave.
I have cried when a colleague gave me feedback that was honest but hard to hear.
In many of those moments, I had Annette Reavis there to give me a hug.
Annette was my former HR partner, but she was far more than that to me. Annette has seen me at my best and my worst, and no matter the problem, no matter my emotional state, Annette saw me with total acceptance.
I know I am one of many in her orbit who feel this way.
Annette sets the bar for me for what supporting others looks like.
She has an uncanny ability to see things exactly from your perspective, and then take your hand and walk you over to a different vantage point to show you what you might have missed.
She has a sixth sense for knowing when someone is open to change and when they aren’t, and her advice to me on when to push and when to accept shaped the river path of my relationships for years to come.
When I am at my lowest of lows, Annette is one of the few people I can muster up the energy to call. She grounds me; she helps me see what I am and where I can go, and somehow, it never seems so bad anymore.
All of us need someone like that in our lives and our workplaces. I’m grateful to have a friend and teacher in Annette, and I hope I can be for others what she has been for me.
The warm, subtle guiding hand of influence
Some years ago, my friend Ami Vora and I were planning a time to catch up. Our schedules wouldn’t align for an in-person hang, so we opted for virtual. Naturally, I assumed we’d Zoom.
“How about a phone call instead?” Ami asked.
“Sure,” I said, even though I rarely did phone calls.
She called me, we had a wonderful chat, and as an aside I got to hear why Ami likes phone calls: “Your imagination of the person in your head when you hear their voice is better than the image of them pixellated on the screen.”
Fast forward another year. Now Ami and I are catching up while taking a walk around the neighborhood. We share some stories about managing, and I tell Ami I am struggling to stay connected to my remote team.
“One thing that I love to do is send voice notes,” she says. Again, she breaks down why she uses them: “They feel more personal than a 1:1 text message, and you can communicate way more nuance by talking versus typing.”
Fast forward to today.
Yes folks, you’re looking at (err… reading the words of) a bona fide phone-caller and voice-noter.
This change happened quite recently, and took me years!
What amazes me is that to this day, I can remember very clearly the details of what Ami said. Her words seeped into my subconscious, where it worked diligently at nudging me out of my comfort-bubble and untangling my hang-ups of awkwardly waiting for the phone to ring or recording myself rambling into a microphone.
This happened, I theorize, because Ami is so so good at distilling why something works for her, and sharing those experiences in the spirit of helping me. This is the warm, subtle, guiding hand of influence, and it changed my beliefs and my behavior.
Thank you Ami for helping me change my relationship practices for the better — I appreciate you dearly.
PS: Ami is CPO of Faire, and formerly ran product for Whatsapp, so she knows a thing or two about The Hard Parts of Growth, her wonderful Substack. Follow away!
Mining the rich depths of an experience
My friend Helena Price has been doing this incredible series called “Founder Things” which is unlike most other things on the Internet focused on “quick hits” and “2-min takeaways.”
Helena’s approach instead is to take the slow path of unfurling a story — no founder’s journey is the same, no one career is the result of following someone else’s playbook. Instead, the choices we make in life are shaped by our families, the cultures we’ve been a part of, and the various stories we heard and then repeated to ourselves.
I absolutely love this approach and I’m so happy to have gotten the chance to participate in Founder Things. Honestly Helena made this one of my favorite and deepest interviews that I’ve ever done.
Helena and I took a multi-hour walk through green spring hills all whilst talking and reflecting. Helena is not only an incredible storyteller and photographer, but the kind of person who acts as a mirror, who helped me see connections from my story that I had never put together.
If there’s ever been the tiniest whisper in your head that being a founder might be an interesting path, you should *definitely* subscribe to Founder Things.
And if you like mining the rich depths of a life experience in all its twisty shadows and glories, pull up a chair and a mug — I think you’ll enjoy settling down into these long reads.
From the archives: The world needs more CEOs like Fidji Simo
Written right after Instacart’s IPO in September 2023
Yesterday, Instacart IPO-ed after 5 quarters of profitability, tearing open (along with ARM) a frozen-shut IPO window. The stock closed its first day up 12%.
Fidji took over the company before the rules of tech investing flipped upside down and “grow at all costs” was replaced by “get profitable!” while valuations went into freefall — daunting for *any* leader, not to mention one new to a company.
She not only managed to do this with discipline and smart strategic bets (becoming one of the less than 10% of female CEOs to take a company public) but to do it *well*, with a compelling vision and a long eye towards the future.
I can’t say I am surprised, as someone who has been lucky enough to work alongside Fidji for many years.
This is because Fidji represents the type of leader I wish we had far, far more of in the world — the kind of leader that finds the heart in every task and the magic in every person.
When she first told me about taking the Instacart CEO role, the vision was what she wanted to talk about — what would this represent for customers years from now? It wasn’t just about deliveries. It wasn’t just about groceries. She saw and explored the fundamental relationship we humans have with food itself, and what that represents in our lives. That was so core to how she led — getting into the deep heart of what mattered.
One of Fidji’s signature quotes is: “Find the magic in others and shine a light on it.” I cannot tell you how inspiring it is to see someone be so effective yet also so warm, caring, and supportive to countless others. “Transactional” is the absolute opposite of her leadership style — she approaches every relationship like a gift for the long-run because there is more to win together if we help each other.
Fidji, congrats on this milestone (which I know you’ll say is but one step in a much longer journey)! And congrats also to your entire leadership team (including so many powerhouse female leaders like Asha Sharma (COO), Dani Dudeck (Chief Corporate Affairs), Anahita Tafvizi (VP of data + strategy), Priya Monga (emerging businesses) among others!)
I hope that many folks earlier in their careers will find inspiration in your singular style of leadership.
Yes folks, it’s absolutely possible to be: a trailblazing leader, a top CEO, a compassionate human being, a founder, a person grappling bravely with health challenges, a woman, a feminist, a loving mother and wife, an artist and an amazing friend.
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The Looking Glass is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.
