Welcome to Digital Native!

I’m Rex. By day, I work as a Partner at Index Ventures based in New York; by night, I write about tech and startups.

Every Wednesday morning, you’ll get a piece straight to your inbox.


What to Expect:

At its heart, Digital Native is about how people and technology intersect; the things that interest me are the ways that humans use technology to communicate, to collaborate, to create. We’re fortunate to be living in a time of rapid innovation, and it feels like the pace of change is only accelerating.


The 10 Most-Read Digital Native Pieces of 2022:

To give you a taste of what to expect, below are the 10 most-read pieces from the past year:

1) Everything Everywhere All At Once: The Explosion in Generative AI

A friend recently asked me: is AI the next bubble or the next big thing? The answer is probably both. This piece unpacks the “why now” behind generative AI, digging into the latest advancements in image models and language models. Then I look at the use cases and business models most likely to emerge in generative AI.

2) 10 Charts That Capture How the World Is Changing

These 10 charts embody some of the most interesting and important shifts of our time, from climate change to media consumption to job growth. Each chart is accompanied by a brief explanation.

3) The $100 Trillion Opportunity in Marketplaces

B2B commerce is 4-5x larger than B2C commerce, yet remains analog and inefficient. Cloud and mobile, the two biggest tailwinds of the last decade, have still barely touched B2B transactions. That’s starting to change.

4) The TikTokization of Everything

Mobile and cloud aren’t saturated, but they aren’t as ripe for greenfield opportunity as they once were. In their place, AI is stepping in as the next wave of innovation, and we’re seeing every category be reinvented. This piece focuses on personalized, algorithmic recommendations.

5) Revisiting LTV & CAC

In this macro environment, it’s important to revisit the nuts-and-bolts of unit economics. Too many companies have lost discipline when it comes to lifetime value and customer acquisition costs. This piece goes through the math, using Spotify as an example, and explores common errors that companies make.

6) The Seven Deadly Sins of Consumer Technology

The old adage goes, “Social networks do best when they tap into one of the Seven Deadly Sins.” Pride. Sloth. Envy. Greed. Gluttony. Lust. Wrath. This piece refreshes that thesis for 2022, looking at old and new startups building on each sin. (The follow-up to this piece explored startups building on the Seven Heavenly Virtues—counterparts to each Sin.)

7) This Is Water: Revisiting Social Constructs

There are a lot of things we take for granted, but that are totally...made up. The largest opportunities for startups exist when you question the status quo and rethink social constructs. This piece unpacks which social constructs are ripe for change.

8) The Rise of Cash App

Cash App is the world’s most underrated social network, leveraging savvy marketing and smart business strategy to overtake Venmo and become America’s leading consumer fintech. This piece unpacks how that unfolded and what we can learn from it.

9) The Transformation of Commerce

As spend moves online, commerce is becoming more sustainable, more efficient, more affordable, and more convenient. Power is shifting to the consumer. This piece explores 10 mega-trends in commerce, from livestreaming to resale, sustainability to post-purchase experience.

10) Minions and Gen Z Characteristics

This piece breaks down 10 characteristics of Gen Z—from thrifty to anxious, entrepreneurial to escapist—and explores the ripple effects of generational behavior changes. Oh yeah, and we talk minions.


You can also join the Digital Native community on Discord, if you’re looking to meet people with similar interests and riff on these topics:

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Rex Woodbury
Partner at Index Ventures