Sari Azout is difficult to label  –  newsletter writer, entrepreneur, VC, and product person who looks at technology with a uniquely human lens. Her weekly Check Your Pulse newsletter is one of a few must-reads. For this issue of the Letterlist interview series, Sari talks about disrupting the status quo, how publishing a newsletter helped her uncover her purpose, and collective ownership models that could rewire the economics of businesses (I find this especially compelling).

Tell me about you, Sari. Where are you? Where did you grow up?

I was born and raised in Barranquilla, Colombia. My great grandfather immigrated to Colombia from the Middle East and built a business from nothing, so I was raised to believe that going out, building something and disrupting the status quo is totally possible. I moved to the U.S. to go to college (I went to Brown) where I studied sociology and economics. I’ve always been fascinated by consumer behavior. I’ve spent the last decade of my life working in startups – first as a founder (I built and sold a second hand apparel marketplace called Bib + Tuck) in NYC, and more recently as a VC and strategist based in Miami.

After close to a decade working in tech and startups, I have a difficult time explaining what I do. Words like VC, product strategist, or creative businessperson just don’t cut it. Sure, my projects and investments involve AI in all its forms, but when it comes to startups, I’m less interested in the latest technology and more interested in the people who make the technology, who use the technology, who benefit from the technology, and whose lives may be impacted by the technology.

How did Check Your Pulse come about?

In early 2019, I started doing weekly “What Inspired me this week?” roundups on my Instagram stories. The feedback was incredibly positive, but what I realized after doing it for a few months is that Instagram, with infinite scroll and stories that keep playing until you force yourself to stop, was not conducive to long stretches of focused thought, which is exactly what I was craving.

After a few months, I transitioned to sending a newsletter on Substack with curated links/comments from around the Internet. It wasn’t until after I sent 10 or 15 newsletters that I realized the unifying thread in my work was the intersection of tech and humanity. Today, I describe CYP as a weekly email newsletter where I explore startups, technology, and cultural trends through the most important lens: the human one.

This is fascinating, like you used your newsletter as a sense-making tool. Can you unpack that moment of realization, where you found that human/tech thread?

Before starting the newsletter, I thought I needed a big idea. But what I realized is that writing is what allows you to crystallize those ideas in the first place. In other words, you don’t need a big idea to write. You write to get the big idea.

Initially, I was just sharing thought-provoking links and thoughts. As I reflected a few weeks into the newsletter (I was looking for a one-liner to describe the newsletter), I came to the realization that what makes me unique is that I am a business-minded VC but I have a creative/human spirit.

Sure, I’m interested in sharing thoughts and articles on new startups and up and coming trends, but I’m just as interested in thinking about how meaning will shift in the coming decades, how nuanced the path to success is, and to shed light on the hidden truths/sacrifices of the founders and innovators we admire. My newsletter is my attempt to humanize the hustlers, bring more creativity to business, and more empathy to tech. In other words, it’s a desperate cry to wrap our technological progress around our own enlightenment as a species.

Since then, I describe Check your Pulse as a tech and startups newsletter designed to make you feel human.

What else are you working on?

I am the head of strategy for a startup studio, Rokk3r, and also run an early-stage VC fund focused on companies building trusted, category-defining, consumer obsessed brands. That means I spend my days investing in and working with founders that are reimagining outdated industries and helping them with digital product design, organizational design, business strategy and storytelling.

How many subscribers do you have, right now? What have you done to grow the audience? What worked? what didn’t?

I have close to 4,000 subscribers. I started by announcing the newsletter on my personal Instagram, which got me to about 500 subscribers. From there, the growth has come mostly from readers sharing it. Many of my readers are influential leaders with a following, so there’s been a few instances where they’ve shared the newsletter that have really moved the needle. Having a link to subscribe on my email signature also helps, since I’m exchanging emails with dozens of entrepreneurs and investors every week.

What’s your big goal for CYP? How does it fit in with your other projects?

For now, I’m focused on continuing to grow the readership. Frankly, I’m just happy to see the hours I spend reading and scouring the Internet pay off by sharing links and ideas that inspire people to live and think better. My broader mission is to bring more humanity and creativity to technology and business. I have a few other projects I’m working on. In particular, I’m spending a lot of time thinking about media consumption.

The Internet made everyone a journalist, and we’ve seen a proliferation of content from the VC/founder community which is a good thing. But it’s also overwhelming to keep up. I have some ideas that have been marinating in my head for a few months around content curation, and my hope is that the newsletter will serve as a launchpad for these other projects.

I’m obsessed with other peoples’ process – how does CYP come together? What’s your workflow? What tools do you use? Who else is involved?

It’s just me doing it the old school way. I use the Notes app on my mac to collect links and ideas I come across throughout the week. On Friday afternoon, I block 2-3 hours to put it all together. I’m planning to transition my notes to Roam Research, a new note-taking and thinking tool that allows you to establish relationships between your notes in a more organic way. It’s extremely powerful and designed to mimic the way you think.

Nobody else is involved, though I wish I had some help – it’s more time consuming than people think!

Can you describe your investment strategy? What was your most unexpected success?

I look for founders that are obsessed with customer happiness and that leverage design, technology, and brand to build trusted, category-defining companies in old stodgy industries.

One of our breakout companies, Hippo, a modern home insurance brand, is a perfect example of our thesis. The thesis was that home insurance is a sleepy but massive industry with incumbents having antiquated distribution channels, policies that are not suited to modern lifestyles, and their legacy systems will prevent them from being able to adapt to new consumer expectations. Hippo used technology, design, and branding to make insurance simple, delightful, and human.

It feels like we’re in this exponential watershed in tech. What’s overblown and what are we underestimating?

Any industry where there is a low NPS score and incumbents struggle to innovate represents opportunity. If you think about it through that lens, then all major categories of consumer spend will be reinvented in the coming decades – healthcare, insurance, education, retail.

Insurance, for example, will shift from recovery after risk to prevention of risk, making way for companies like Hippo. Our health system will shift from sick care to actual health care, making way for companies like Parsley Health. Education will be centered around life skills and career preparedness, opening up opportunities for companies like Lambda School and displacing much of the traditional education system. Retail is already undergoing a massive shift, as we’re seeing from the massive wave of DTC brands leveraging Shopify and Instagram to bypass retailers and reach consumers directly.

The problem with these views is not whether they are true or not, but rather the time frame in which they occur. For example, I’m sure iPhones will be displaced by something else, but I don’t think that will happen anytime soon, so I am not investing in AR/voice companies in the near future. Same for self-driving cars – I have no doubt cars will drive themselves, but I think we overestimated how quickly that change would happen, leading to lots of casualties in the AV space.

Getting the timing right is the key.

What is it about email newsletters that makes them so enduring? How do you see email publishing playing out over the next 3-5 years?

I think email newsletters will become the next social network. They represent an antidote to news feeds, and people want their media consumption to be a more conscious choice. As newsletters experience a renaissance, we will transition from free social media platforms that turn us into addicted extremists to niche subscription services built on platforms like Substack or Podia.

Our digital social environments will change, re-emphasizing private interactions and helping us build the smaller communities we all crave. The rise of newsletters will open up opportunities not only for creators to directly monetize, but also for new media consumption platforms. I don’t think people want to sign up and pay for 10 newsletters – a classpass for newsletters would be a more efficient alternative where people pay for what they consume.

What big idea would you love to work on if you had unlimited time and money?

I published a full list of my request for startups I want other people to build 🙂

But the #1 thing I really want someone to figure out is collective ownership. Carta simplified equity and stock options but somebody needs to figure out how to make platforms be collectively owned. Uber drivers, Airbnb hosts, Sofar artists – they should all participate in the economic upside of the company. Inequality is one of the most important issues we face — the top 10 percent of humanity has 90 percent of the planet’s wealth.

There are examples of companies like Chobani, REI, and Patagonia issuing equity to employees and customers but this is far from easy for most companies to execute. What if issuing equity were as easy as paying a salary? We know that ownership and passive income are the only sure routes to financial freedom, so how can we democratize ownership in the process and reduce income inequality?

I think there is an opportunity to offer distributed ownership models as a service. Tokens might present a viable way to make this happen. Ultimately, marketplaces should evolve from being intermediaries that take a commission on each transaction (causing participants to resent them) to being collectively owned platforms that align incentives across all stakeholders.

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Published on Substack.