An Outsider's take on Silicon Valley culture
Featuring Kim Lear
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👩 Is Silicon Valley the city of the future? An Outsider’s Perspective.
About five years ago, I saw Kim Lear speaking to a crowd of consultants and was star-struck: she’s a dynamic speaker and an insightful researcher. (A rare combo!)
Over the past decade, Kim has worked with cities across America to help them understand what it takes to build next-generation communities. Her work on generational trends, longevity, social media, and the future of the workplace has been featured by NPR, the Wall Street Journal, and TIME Magazine. And she wrote one of the greatest Twitter bios of all time:
@kim_lear_: Watching how you spend your money and live your life. In a research way, not a stalker way.
Kim has recently become a loyal Outsider, and she graciously agreed to help me create this piece. If you’re interested in…
The perception of Silicon Valley in the Midwest
What it’s like to live in SV, and why folks are moving away
Whether Silicon Valley is really the global beacon of innovation
Overconfident tech bros
…then keep reading! Without further ado, I present: Kim Lear.
Hey Kim! Welcome to the newsletter. We’ve talked in the past about how folks in the Midwest think about Silicon Valley, and I’d love to dig into that together here.
To begin: when you talk about Silicon Valley with your friends and colleagues, what do they say?
Well, first, thanks so much for having me.
I have a lot of friends who have left SV because they are at an age where they have the connections they need, they want to buy a home and start a family, their tech dreams didn’t come to fruition and the instability is too anxiety-inducing, their tech dreams did come to fruition and they are set financially, they are over the mono-culture, or they want to be closer to family.
I wonder whether this exodus is dangerous for the next generation of Silicon Valley, because so much of what has made SV innovative and rich with ideas was having this cohort of folks that have been living there for 10, 15, or 20 years. There was a huge culture of mentorship, and people who want to groom entrepreneurs, but if many of those people are leaving, what happens?
And what do outsiders say about SV? People love it for the most part. The access to brilliant minds and VC money is unlike anywhere else. The nature, the food, the culture of risk and ambition, etc.
And what about your impression? We’ve talked previously about topics like socio-economic homogeneity and innovation…
My impression of SV as a geographic place is that I love it. I could do without the strip malls, but overall, I love it. The proximity to mountains, to the ocean, to wine country... it’s amazing. The food is exceptional. If I could, I would eat at Rangoon Rubys once a week. This may shock you but Minneapolis is a little light on quality Burmese food.
My impression of SV as the end-all-be-all hub of brilliance and innovation... I don’t think that’s true and I think it does a disservice to pretend that one city has a monopoly on innovation. A monoculture has a negative impact on intellectualism, diversity, inclusivity, and curiosity…
In July of last year, Diana Helmuth wrote a beautiful essay in Curbed San Francisco where she said:
“We are witnessing two migrations. One is the continuation of the Californian dream, where young people flock here for gold and glory, ready to hustle and disrupt, hammering to hit the motherlode and laughing at the odds. The other is the migration of young people out of California, which seems to have affected everyone I know, but which I rarely hear examined. These people want to be artists, teachers, blacksmiths, therapists, mechanics, and musicians. They want to have children, open bakeries, own a house. But they can’t. There is no room here for those kinds of dreams anymore.”
And why does this matter? I think solving problems requires diversity. Not only diversity of race, ethnicity, gender, an area big tech has notoriously struggled with... But also people with all different kinds of dreams and aspirations, people with different interests and passions, etc.
Rebecca Solnit, historian, activist, writer, and California native, wrote, “Our rich are getting richer. Our poor are getting more desperate. Our hipsters are getting more pretentious. San Francisco is now a cruel place and a divided one.”
That really resonates with me. Right after moving from Minneapolis, I remember being shocked at the way that folks in San Francisco interacted (or, rather, didn’t ever interact) with people experiencing homelessness.
I’d love to talk more about innovation. I came to Silicon Valley to pursue the entrepreneurial dream, hoping that the culture of “failing fast” and trying crazy things would rub off — as much as I posture otherwise, I think I’m truly risk averse. (That probably explains why I needed the MBA safety blanket to make the plunge into starting a startup.) I know we’ve talked in the past about “failing gloriously,” a central concept in my own entrepreneurial story, and you had some hot takes.
I think failing gloriously is often reserved for people prepared to sacrifice the comfort of conventionality (getting married, having kids, buying a home, etc.) or for people who have a safety net. I’m not talking about massive trust funds. I mean that their glorious failures aren’t going to make them homeless or hungry. When I interview young people from low income families, oftentimes they need to focus their attention on immediate matters having to do with health insurance, loan payments, and basic necessities. Failing gloriously on a food delivery app (or something like that) is not typically the focal point for people struggling with day-to-day life.
Anand Giridharadas has talked a lot about the impacts of young people with safety nets having the luxury to “make the world a better place.” The catch is that they are also the ones who get to subjectively decide what a “better place” looks like.
SV is always talking about the culture of risk but if SV founders have some socioeconomic homogeneity which includes a safety net, are these really great risks? Worst case scenario, many (not all, but many), are still going to be totally fine.
Absolutely. The early-stage startup thing isn’t for everyone — meaning that not everyone has a fair shot, and not everyone would enjoy it. I think Silicon Valley runs into many of its (frequent) PR problems when it forgets that fact and starts claiming the world as its dominion.
But maybe that’s just a side effect of the system: give 1,000 young people $100,000, one of them turns it into $10,000,000, and of course they think they’re a genius who deserves to rule the universe.
Tim Ferris wrote something similar in his 2017 Reddit AMA. Ferris said SV has the highest concentration of brilliant people and the highest concentration of people who think they are brilliant. I know that midwestern humility can stand in the way of innovation but I think SV’s overconfidence creates a whole host of other problems.
I do believe that COVID was a wake up call. I think the election and the role the big tech played in it is a wake up call. I think watching artists flee the Bay Area is a wake up call. I think people walking over homeless people to enjoy meals at Michelin star restaurants is a wake up call. I think 35-year-olds living in communes because they can’t afford independent housing is a wake up call.
I don’t want this to seem that I’m pessimistic about SV. I began working there in 2013 to help run onboarding programs at two large tech companies and I was always in awe of the amount of smart people in a concentrated area. Many of SV’s innovations have been widely transformational. But across the board, America’s innovative energy has stalled since the 1970s. Innovation in our everyday activities has improved very little since the 1970s. The best resource on this is The Rise and Fall of American Growth.
People outside of Silicon Valley are constantly told about the high concentration of brilliance and seemingly endless amount of available capital. Because of this, I think it’s easy to understand why the expectations for innovation are so high, and yet, our infrastructure hasn’t changed dramatically, our healthcare, our air travel, etc. have stagnated.
People are rooting for Silicon Valley. Outsiders desperately want the brightest minds solving the most pressing and urgent problems of our time — but in the midst of a major public health crisis, I think many people saw that SV was extremely limited.
What I really wonder about most is whether this — *gestures broadly at everything* — can change.
Can the SF Bay Area be less of a monoculture, can the Midwest change to become an innovation hub, can we realize the ideals of Silicon Valley (and avoid their negative side effects) elsewhere in the world? Or are these cultural dynamics just too big and multifaceted to intentionally change?
Something that I really agreed with in your interviews with those two women from the Midwest was about how innovation can look different in different places. That’s a good thing. The Midwest doesn’t need to behave like SV in order to be innovative. Just like most people interested in next-gen cities, I’ve been specifically looking at Atlanta, Seattle, Portland, and Austin. I would argue that some of those cities are very comparable to SV in terms of a risk-forward, innovative culture. In the Midwest, Minneapolis and Columbus are particularly interesting to me.
So, is Silicon Valley positioned to be the hub of innovation moving forward? I think SV will always be a hub of innovation, but not the only hub and potentially not even the most powerful. COVID has dispersed top talent all over the country. Now we need to see what other cities do with this rare opportunity.
🤩 If you want to follow Kim…
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🔙 Last Week in Startups
Last week, I wrote a huge article about what it’s like to work at different stages of startup life: everything from the early days of the “Drunken Walk” to the later stages where you’re really just a company with fancier-than-average snacks.
While writing, I reached out to a bunch of my friends working at startups for their takes. Predictably, many were too busy to get back to me in time. (To be fair… I also reached out on, like, Saturday. My excuse is that I’m also working at a startup!) And, also predictably, their answers were awesome. Here are two that arrived just after I hit publish last week:
Given we’re a hardware company, the day to day focus is still in developing our product and R&D (vs. software companies are often in full sales mode by Series C). That said, we’re also beginning to build relations with key customers that will support our GTM. As CoS, my main focus is on building up our corporate functions (finance, legal, BizOps) so they’re at the standards of larger corporations.
As far as stressors, this is unique to the self driving industry: the possibility of a safety incident is probably top of mind for all executives.
I’m most excited to see how this industry unfolds given how novel it is. As a more established company in the space, we’re squarely in the middle of the action.
Now that we have more than 20 FTE, my role has shifted much more towards people management, team communication, and hiring. I'm less involved in day-to-day operations of the company, although I do still run our SEO efforts and do some product work. My cofounder leads product, and we have an awesome team of engineers, operators, and content creators.
What’s it like working here? It's amazing! Everyday, I'm living my dream, which is to say that I'm leading the biggest company I've ever led (since we're growing :D ). I'm especially inspired by the creators that Kapwing serves. It's sometimes overwhelming because there's a lot to do, but I love being at the bottom of a learning curve every day. One contrast to my previous job is that I make mistakes all the time and frankly I'm not great at my job, but I'm learning thanks to a motivated, patient, and communicative team.
And how has it changed since the early days? It’s very different. The product has matured a lot, and we've focused our product vision from doing a bit of everything to focusing on building a premiere video editor in the browser. We're much less concerned about money than we were in the early days as we have plenty in savings, growing close to profitability, and feel confident that we could raise more if we needed to. Our user base is much larger, so we need to address scaling issues, and our team is larger, meaning we need to focus on management, culture, and people operations more. We've set up process in places where it's needed, and I personally spend a lot of my time on hiring.