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Not Boring

Not Boring

By Packy McCormick
Tech strategy and finance through the stories of companies big and small.
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The Great Online Game

Not Boring

Not Boring Founders: Regy Perlera, Seasons
Regy Perlera is building the future of retail with Seasons, an access-oriented rent-to-own platform for men.  What most impresses me about Regy is that Seasons, which is very much designed for a world in which people go out, came out of COVID even stronger, and with a broader vision, than when the company started. We'll cover that story, along with:   - Lessons learned from Rent the Runway   - How to stay ahead of the fashion curve  - Whether and how Seasons is thinking about web3  - Regy's #1 piece of advice for founders  I think this is going to be a public company one day, and Regy is a world-class founder with experience at Nike and StockX. You don't want to miss this. 
November 29, 2021
Idea Legos
Chris Dixon tweeted that "Composability is to software as compounding interest is to finance." Money builds on money; software builds on software; the results are exponential.  While it's harder to measure or intuit, the same is true for ideas. Each new idea is an idea lego.  Read the full post at Not Boring.
November 22, 2021
Not Boring Founders: Alexa Grabell, Pocus
Alexa Grabell is the co-founder and CEO of Pocus, a product-led sales platform backed by First Round Capital. Alexa started the company while getting her MBA at Stanford GSB based on her experience leading up sales strategy and operations at Dataminr. We discuss a wide range of topics including defining a new category, setting up a co-founder relationship for success, how to get the most out of early design partners (and what a design partner is), and how companies can add product-led sales to their toolkit. This one is packed with wisdom and practical insights. 
November 16, 2021
Let's Buy the US Constitution
As we speak, thousands of people are contributing funds to the ConstitutionDAO in order to win a copy for the last remaining private copy og the US Constitution when it goes up for auction at Sotheby's on Thursday night. It's expected to fetch roughly $20 million.  We'll cover the backstory, what a DAO is, and the significance of a group of people using web3 tools to buy the US Constitution together.  You can read the full post at Not Boring. 
November 16, 2021
Discord: Imagine a Place...
Imagine a place...     Built for gamers Home to everyone playing the Great Online Game Has 150 million MAUs Generates $130 million in revenue Is a web3 sleeper This week, I teamed up with Mario Gabriele of The Generalist to tell Discord's story. You can read the full piece here.  We cover: The circular origin story. Discord’s lore involves more headfakes and false starts than almost any other business. A dizzying product. Discord can be hard to understand, especially for aged millennials like Packy and me. We do our best to dissect the chaos of Discord’s chat. A forking user base. Though it began as a tool for gamers, Discord is now widely used. We’ll talk about its primary constituencies. Slow monetization. While it has grown rapidly, Discord’s been conservative when it comes to extracting money from users. The web3 opportunity. Discord has become the platform-of-choice for web3 entities, but it doesn’t seem to have totally won over hearts and minds. The company needs to capitalize on its lead and protect its positioning. We have some ideas. The Great Online Game. How Discord has become the home for those learning, living, and winning on the internet.
November 8, 2021
Not Boring Founders: Jack Alton, Neuro-ID
Neuro-ID is a real-time behavioral analytics tool that analyzes all of our very human and unique taps, clicks, and swipes to help its customers fight fraud and better understand their customers. The company, based out of beautiful Whitefish, Montana, announced a $35 million Series B yesterday, in which Not Boring Capital is participating. I sat down with CEO Jack Alton to discuss:   - What Neuro-ID does  - Transitioning from fighting fraud to a wide range of use cases  - The unlikely advantage of the Whitefish HQ   - How the Series B came together  - What the company plans to do with the money  - How to do a founder --> outside CEO transition right. 
November 5, 2021
Minimally Extractive Meta
Last week, Facebook announced a rebrand to Meta and an all-in bet on the Metaverse. Zuck said all of the right things about openness and interoperability.  The question people are asking is, "Can we trust him?" The more interesting question is, "Do we even need to?" In a world in which people are more used to ownership of their digital assets and identity, Meta’s best strategy will be to operate more like a Minimally Extractive Coordinator than an extractive platform. To reach its full potential, Meta needs to disrupt Facebook by turning itself into something that behaves more like a protocol than a platform. Plus, Meta will be a better influence on the Metaverse than Apple.  You can read the full post at Not Boring.
November 1, 2021
Since February, I’ve been writing an accidental series on how web3 is impacting culture, work, and the way that we all interact with each other.  Power to the Person was about how technology is empowering individuals as the new atomic units of commerce, The Great Online Game was about how the internet blurs the line between work and play for those individuals, and The Cooperation Economy was about how we play the game as teams of individuals or small groups.  This essay goes one layer up to figure out how it all fits together: we’re all part of a great global Scenius. We’re all gonna make it. Let’s call it the WAGMI Scenius. You can read the full post at Not Boring.
October 25, 2021
Not Boring Founders: Lauren Rothwell, Retrera
Lauren Rothwell is the co-founder and CEO of Retrera, a platform for remote employee engagement that makes it really easy to host team offsites and retreats. Every founder that I talk to with remote employees, even those who have offices, is organizing at least one offsite per year, and often one per quarter. They love getting the team together in a new location to build bonds, but organizing it all can be a huge headache full of hidden costs. Retrera makes that simple, with one tool to survey employees, book hotels, organize meals, purchase flights, and even follow-up to get feedback from employees and track their engagement over time.  The corporate offsite market is massive -- something like $27 billion annually and $12 billion just for tech companies -- and Lauren is taking the smartest approach I've seen to bringing order to it. Before Retrera, Lauren studied math & econ grad from Trinity College Dublin, traded at Goldman Sachs, and went to business school at Stanford GSB. Her co-founder, Chirag, was an engineer at Airbnb and Facebook. Their skill is evident in the product and the growth they've seen: in just two months live, they've done 14 offsites for over $1 million in GMV. They're making remote work more fun and engaging.  Your team should do a retreat. Go book a Retrera.
October 19, 2021
Playing Solo Games
Not Boring Capital has invested $8 million in 79 companies over its first two quarters. That's fast. This weekend, I sent an LP Update to Not Boring Capital's LPs. In this episode, I share the update with a particular focus on Not Boring Capital's strategy and the trade-offs I need to make to lean into my comparative advantages and away from areas where I'm weaker.  You can read the full post at Not Boring.
October 18, 2021
ScienceIO: The Model of Everything
ScienceIO decodes the language of medicine to unlock the full potential of healthcare data. Its industry-leading clinical Natural Language Processing (NLP) platform structures data in real-time to enable search, analysis, and insight generation.  Not Boring Capital invested in ScienceIO's $8M seed round, and in this episode, I'll explain what they do and why I invested, covering:  The Investment Thesis The Challenge: Unstructured Zettabytes The Team: Building on a Strong Foundation The Products: The Model of Everything The Business: 💰📈 The Future: Patient 360 and Healthcare Infrastructure You can read the full post at Not Boring.
October 14, 2021
Not Boring Founders: Ayush Jaiswal, Pesto
Ayush Jaiswal is the founder and CEO of Pesto, a Not Boring portfolio company that connects companies with the most valuable resource in the world: engineers.  Ayush founded Pesto because he realized that remote was coming even before COVID, and that companies working anywhere meant that they could hire the best talent from anywhere. He also saw that in India, his home country, some of his friends who were talented engineers were making a fraction of what they could working for a western tech company. Pesto fixes that, identifying top engineers globally, starting in India, training them on soft skills, and matching them with higher-paying tech jobs. And it's working -- the average Pesto developer makes 4x what they made before Pesto and hiring companies come back to hire as many as 12 (and soon 30) Pesto developers.  We discuss:   - What remote will look like  - How to identify top engineers  - Expanding into web3   - Why Pesto has focused on growing within existing clients   - How to hire Pesto engineers Listen, or if you just want to hire an engineer right now, go check out Pesto to see profiles of available developers today: Try Pesto.
October 7, 2021
Not Boring Founders: Nick Greenawalt, Wanderers
Nick Greenawalt is the co-founder of Wanderers. I've become obsessed with Wanderers since discovering it a couple of weeks ago. The current batch of 8,888 NFTs are 8 second animations of space ships hyperdriving through space at warp speed, soundtracked by spacey music. That's just part one of Phase I of the Wanderers master plan. Next up: every Wanderer holder gets a free planet NFT dropped in their wallets. Beyond that await avatars, mysteries to solve, and a big story to tell. There's also a thriving Discord that's the second thing I check every morning after Twitter. Wanderers has resonated with me more than any NFT project to date, and after talking to Nick, I'm only more excited about what's in store. After you listen, I think you'll understand why.  Seeing is believing, though. Check Wanderers out on OpenSea and join the Discord to experience it for yourself.  
October 1, 2021
Existential Optimism
Power is shifting from institutions to individuals. Remote work, web3, the Great Resignation. When careers, jobs, or institutions are no longer as reliable a source of meaning as they once were, how do we find our own meaning? How do we keep it all from spinning out of control?  Today, we're waxing philosophical. We'll explore Existentialism, Jean-Paul Sartres, and why now might be a good time for an existential comeback.  No doctrine is more optimistic, since it declares that man's destiny lies within himself. Read the full post at Not Boring
September 27, 2021
Not Boring Founders: Reed McGinley-Stempel & Julianna Lamb, Stytch
Going from 0 to 1 -- taking your company from idea to real live working product with customers -- is hard.  In this special edition of Not Boring Founders, Packy and Thrive Capital's Gaurav Ahuja sit down with Stytch co-founders Reed McGinley-Stempel and Julianna Lamb to discuss how they've done it. In the past 18 months, they left their jobs at Plaid and Very Good Security, raised money from Benchmark, Thrive, and other top funds, hired an all-star team, built a passwordless authentication API and SDK, and sold to their first wave of customers. We cover:  How to make the leap from secure job to startup  The importance of clarity of thought  How to raise money from VCs  How to hire top engineers Why you should go slow to go fast  If you're a developer, you should check out Stytch. It's user infrastructure for modern applications.  
September 24, 2021
Absolute Unit
Unit is a banking-as-a-service (BaaS) platform that lets tech companies embed financial features into their products. It's growing spectacularly fast and has raised over $70 million from some of the leading investors in fintech since its founding in July 2019. What makes Unit special is that it believes that tech companies with existing distribution are in the prime position to grow fintech over the next decade, and makes it as easy as possible for them to offer banking services to their customers by handling tech, bank relationships, compliance and more.  We'll cover: The Fintech Apps-Infrastructure Cycle Meet Unit Standing out in the Competitive BaaS Space Unit’s Growth and Opportunity This is a sponsored deep dive x investment memo. Not Boring Capital a proud investor in Unit. Read the full piece at Not Boring. 
September 23, 2021
Crypto Bezos
What kind of company would Jeff Bezos start if he were 30 years old today? We look back at four '90s Bezos interviews to try to figure out what he would look for and how he would approach starting a company today. (Hint: it's probably a crypto company).  Read the full post at Not Boring. Give your answer and join the conversation on Twitter. 
September 20, 2021
Not Boring Founders: Chris Toy, MarketerHire
Chris Toy is the co-founder and CEO of MarketerHire, a talent marketplace for the world's best marketers. MarketerHire is quietly putting up some all-time great growth numbers and is perfectly positioned to help companies and talented people make the transition to the future of work -- not just where we work, but how we work. We dive into Chris' background, why marketing is the Apex predator of internet jobs, and how to build and grow a marketplace. Today's episode is brought to you by Cometeer. Find out why it's a new day on earth for coffee, and get 50% off your first order at
September 16, 2021
The Interface Phase
We shape our interfaces; thereafter, they shape us. Today, we’ll explore how those new interfaces and spaces might bring web3 mainstream: The Apps-Infrastructure Cycle An Incomplete History of Interface SuperCycles Web3 Interfaces Into the Future We'll dive into web3 worlds like Cyber, Decentraland, The Sandbox, and Somnium Space and wallets like MetaMask, Phantom, and Rainbow to guess what web3's native interface might look like. Read the full post at Not Boring.
September 13, 2021
Solana Summer
Solana is one of the most valuable and fastest growing blockchains in the world. It can handle over 65,000 transactions per second, and transactions cost a fraction of a cent. Over the past few months, both the price of SOL, its token, and developer activity on top of Solana have exploded. Today, it has a $21.5 billion market cap with over 300 projects built on Solana. It's a leading contender to join Bitcoin and Ethereum in the blockchain pantheon, and to bring the next billion users into crypto.  In this sponsored deep dive, we cover:  The Core Questions Solana’s Story How Solana Works Solana’s Orbit The Ecosystem Case Studies: Star Atlas, Saber, Audius How Value Accrues to Solana Bull Case for Solana Bear Case for Solana Solana Summer You can read the full post at Not Boring.
August 24, 2021
Story Time: The Progressive Decentralization of Narrative
The way that companies tell stories and build narratives is changing -- from top-down storytelling to bottoms-up narrative-building. Because they're such empty vessels for narrative, NFT projects like CryptoPunks and Degenerate Ape Academy make a useful study. We’ll cover: From Storytelling to Narrative Building Narrative in Venture Capital and Startups Lessons from Crypto Read the full post at Not Boring.
August 16, 2021
Lithic's New Customer
You may not know Lithic. Until recently, it was called  In May, it announced an Amazonian move: delivering the card issuing & processing infrastructure it built for itself via an API. Now, it's worth $800M and growing like a card rocket. This is a fun one. We'll learn about Lithic's pivot using the framework that Ben Thompson laid out in The Amazon Tax. Build primitives, incur high fixed costs, expose primitives via API, get increasing returns to scale. Read the full post at Not Boring here.
August 12, 2021
Equi: Is That a Family Office in Your Pocket?
Equi is building one of the most impressive investment tech products I've ever seen.  The problem: Institutions & family offices have 50% in alternatives. Individuals have
July 29, 2021
Pinduoduo: Together, More Bull, More Bear, More Fun
Pinduoduo is the fastest company in history to reach both $5 billion in revenue and a $100 billion market cap. The Chinese ecommerce platform, famous for popularizing the team buying and consumer-to-manufacturer (C2M) model, was the talk of the town last summer, and it's had an even more fascinating intervening 12 months. I teamed up with Lillian Li of Chinese Characteristics to go deep, and give the bull and bear cases, including: A Brief History of Pinduoduo What Does Pinduoduo Do? Can PDD’s Model Work in the West? Recent Developments: Leadership, Grocery, Agriculture, and Payments The PDD Bull Case -- Packy The PDD Bear Case -- Lillian Beyond Pinduoduo   You can read the full piece at Not Boring.
July 26, 2021
Axie Infinity: Infinity Revenue, Infinity Possibility.
Bet you've never seen something like Axie Infinity.   April: $670k revenue   May: $3M  June: $12.2M  July (18 days in): $79.1M   Axie is a blockchain-based, Pokémon-like game pioneering a Play-to-Earn model. People work by playing video game.  It looks cute. It's so much more. You can read the full post at Not Boring here.
July 19, 2021
Not Boring Founders: Saad Alam, Hone Health
This is the first episode of a new series we're doing: not boring founders. It's a behind-the-scenes look at the companies I'm backing with Not Boring Capital, from the mouths of the founders building them. We'll talk about their products, but we'll also dive deep into how the businesses work, how they think about company building, and the strategies they employ to win.  For our first episode, I'm talking to Saad Alam, the founder and CEO of Hone Health. Hone treats men's hormone imbalances and low testosterone by providing access to at-home lab testing, physician consultations, and medication such as Testosterone from the comfort of your home to get your SPARK BACK & BE YOUR BEST. It's also a fast-growing business that needs to get a lot of really hard things right.  Saad is a phenomenal CEO, and you'll learn a lot from him about building and optimizing your funnel, branding, and how to get men to actually engage. NOTHING IN THIS PODCAST IS MEDICAL ADVICE If you'd like to learn more, check out Hone.
July 13, 2021
Unit21: No-Code, Much Power
Unit21 builds modern infrastructure for activity monitoring. It just raised a $34 million Series B from Tiger Global at a $300 million valuation to expand from its first use case -- AML / fraud -- to serve the wide variety of use cases in which operators and analysts write and deploy business logic. The company is bringing AI/ML to the people. We'll cover: Founder-Market Fit Meet Unit21 One Platform, Many Use Cases Initial Market: Fighting Financial Fraud Growth and Tiger and Growth, Oh My! When I Needed Unit21 Blue Check and Beyond Trade-Offs and Challenges AI/ML to the People You can read the full post at Not Boring.
July 8, 2021
Not Boring: Ask Me Anything
We're switching it up this week. I asked Not Boring readers for questions on Twitter, and I answered ten of them.  Read the full post at Not Boring.
June 28, 2021
NexHealth: The Secret 3-Step Master Plan to Cure Healthcare
NexHealth is a $400 million startup with a three-part master plan to accelerate innovation in healthcare: First, build a SaaS product for healthcare SMBs, starting with dentists, like Shopify. Then, use the integrations it accesses in step one to build APIs for healthcare, like Plaid. Then, use the doctors and patients and developers it acquires in steps one and two to build a three-sided platform, like Microsoft. You can read the full post at Not Boring.
June 24, 2021
Scale: Rational in the Fullness of Time
Scale is a 5-year-old company building infrastructure for AI & ML. Already, it's achieved a lot: $100+ million in ARR, $7.3 billion valuation, and customers like the DoD, Lyft, Airbnb, & OpenAI. Today, we cover:  The State of AI and ML Getting to Scale Scaling Like Stripe The Bear Case for Scale The Bull Case for Scale Scale’s Compounding Vision You can read the full post at Not Boring here.
June 21, 2021
Cometeer: A New Day on Earth for Coffee
Cometeer makes my favorite coffee. I drink three a day. They arrive frozen, with the flavor locked in, and I just add water.  Today, in this Sponsored Deep Dive + Investment Memo, we cover: Founding Story and Team: Cometeer Co-Founder and CEO Matt Roberts used to be a Dunkin’ guy, until he went abroad and met George Howell, who turned him  on to the good stuff. He and his Co-founder/CTO Doug Hoon have built a stellar team. Market: Coffee is a $94 billion market in the US alone, and there’s a lot of room for improvement. Cometeer has the chance to do to coffee what craft beer did to beer. Product: Cometeer is legitimately great coffee. The magic is in the how. Mission: The why is important, too. Cometeer wants to pay farmers more, promote independent roasters, and stop throwing pods into landfills. Challenges: Brewing and sourcing great coffee at scale is hard. Cold supply chain is hard. Opportunity: Cometeer has the chance to redefine normal peoples’ expectations around coffee and become a platform for the world’s best coffee. You can read the full piece at Not Boring.
June 17, 2021
Zero Knowledge
Zero-knowledge proofs let someone prove that they know or have something without giving up any information about what they know or have. ZKPs have the potential to eliminate a major trade-off inherent in living, working, and transacting online: the convenience, speed, reach, and scale of the internet in exchange for our privacy. They also allow for nuance in a privacy landscape that’s often black-and-white. I teamed up with Jill Carlson to glimpse into future of ZKPs and their implications by covering:  What Are Zero-Knowledge Proofs? The History of Zero-Knowledge The Upside of Hype The Privacy Spectrum Applications of Zero-Knowledge Systems The Zero-Knowledge Design Space You can read the full post at Not Boring.
June 14, 2021
Cityblock Health: The Vertically-Integrated, Value-Based Arbitrageur Fixing Healthcare
Medicaid is a $613 billion market that, as of 2017, had only attracted $20-30mm in VC funding.  That left a massive, if complex, opportunity for someone willing to vertically integrate, take risk, and treat the whole person.  Meet Cityblock Health. Cityblock is literally keeping people out of the hospital and saving lives -- the things that make the company tick are the same: big market, business model with positive unit economics, and an innovative product, powered by technology. We’ll use that framework to understand Cityblock: The Market: Demystifying Medicaid. The Business Model: Value-Based Care. The Product: Treating the Whole Person. Strong Early Results Challenges The Future of Cityblock, and Healthcare Read the full post here. And go work at Cityblock: check out jobs here.
June 10, 2021
The Cooperation Economy
Cooperation is the winning strategy in the Great Online Game.  In this episode, we'll discuss why power is shifting from individuals to institutions, and how individuals can team up to accomplish bigger things together than any can alone. We'll cover:  The Big Smile LeBron and Super Teams Liquid Super Teams The Cooperation Economy in Action Cooperation as a Strategy You can read the full post at Not Boring.
June 7, 2021
Melio: Disrupting the $25 Trillion B2B Payments Market, By the Books
Melio, which has raised $256 million and was recently came out of stealth valued at $1.3 billion by Coatue, makes it easy for SMBs to pay each other. It's a Venmo-like experience on the front, with powerful tech in the back-end. It's also executing brilliantly on the disruption playbook. Today, we’ll look at Melio’s story, product development, viral growth, and future through the lens of disruption. It’s rare that you get such a clear view of disruption playing out in real time. This one’s going to be in the textbooks. We’ll help the professors get started by covering: Disruption by the Book Meet Melio Started from the Bottom Viral Growth Stripes, Squares, and Settles, Oh My! Melio’s Future You can read the full post, and subscribe, at
May 27, 2021
Own the Internet: The Bull Case for Ethereum
What if I told you about a business that:   Has strong network effects  Grew revenue 200x YoY  Is preparing to offer a 25% dividend  About to implement a permanent share buyback program?    That's pretty much Ethereum. This episode is my bull case on Ethereum. It is not financial advice.  Read the full post at Not Boring. Intro Song: I Will Derive - Ethereum
May 24, 2021
Prescription Drug Commercials: Why Are You the Way You Are?
Prescription drug commercials are confusing. People eating ice cream while a voiceover talks about herpes. The Cialis couple in the bathtubs in a field (backstory revealed below). The long list of side effects that seem much worse than whatever disease the advertised drug claims to cure. I asked Nikhil Krishnan, the man behind healthcare newsletter/community/novelty product shop Out-of-Pocket to explain why they are the way we are. He covers:  Why Do Pharma Companies Market to Consumers? What Are the Rules Around Marketing to Consumers? Pharma Marketing is Evolving So... Is Marketing to Consumers Bad? You can read the full post at Not Boring. 
May 13, 2021
The Great Online Game
We’re all playing a Great Online Game. How well we play determines the rewards we get, online and offline. The Great Online Game is played concurrently by billions of people, online, as themselves, with real-world consequences. Your financial and psychological wellbeing is at stake, but the downside is limited. The upside, on the other hand, is infinite. We cover:  What is a Video Game? The Great Online Game Meet the Players How Crypto Supercharges the Game How to Play the Game Read the full post at Not Boring. 
May 10, 2021
Truework: A True Strategy Masterclass
Truework is building the verified identity layer for the internet, starting with employment and income verification. The company has raised $45 million from Sequoia, Founders Fund, Khosla, and Activant, and is executing on a brilliant 10-year plan to win you back control of your most sensitive personal information. We cover:  Meet Truework How to Win a Legacy Industry Regulatory Counter-Positioning The Verified Identity Layer Read the full post at Not Boring.
May 6, 2021
A Not Boring Conversation with Clint Kisker
When Packy auctioned off his Power to the Person essay as an NFT that split proceeds with the people whose work Packy cited, Clint won the auction with a 2.19 ETH bid. We had to talk about it, and I'm glad we did. We covered:  The psychology of NFT buying The future of media and entertainment  How Clint sees Web3 and crypto changing the relationship creators have with their audiences And so much more...  Follow Clint on Twitter
May 4, 2021
Transforming Tata
I teamed up with Mario Gabriele, the author of The Generalist, to study Tata Group, the 152-year-old Indian conglomerate with public subsidiaries worth a combined $234 billion. We cover:   Tata’s rich history, beginning with the opium trade The complexion of a messy conglomerate The necessary moves to perpetuate the dynasty Read the full post at Not Boring.
May 3, 2021
Martha Stewart's Reign of Relevancy
In today's Not Boring Guest Post, Ali Montag writes about the original multi-channel creator: Martha Stewart.  For more than five decades, Martha Stewart has evolved to stay one step ahead of the curve. Montag writes, "Martha Stewart has, over the course of a 50-year career, with mystically perfect timing, refashioned herself from Wall Street stock broker to Connecticut catering chef, from the U.S.’s first self-made woman billionaire to a yoga-teaching inmate in federal prison, from a scandal-tainted villain to renewed brand icon, and from the picture of propriety to Instagram’s latest thirst trap." You can read the full post at Not Boring. Read more of Ali's writing at the Newsletter Crew Newsletter.
April 29, 2021
Startup Stock Option Options with Secfi
In 2020, startup employees left $4.9 billion on the table by not exercising their pre-IPO options. Employees at Snowflake, Airbnb, and DoorDash missed out the most. Most of that can be fixed with a little eduction, so today, in this sponsored post, we're going to explore startup stock options: How Startup Equity Works Why Employees Don’t Exercise Options Exercise Options Meet Secfi The CAC Arbitrage Secfi’s Vision Read the full post at Not Boring.
April 22, 2021
Bull & Bear: Agora, the API Powering Clubhouse
This week, I teamed up with Lillian Li, the author of Chinese Characteristics, to write about Agora. I took the bull case, and Lillian took the bear case. We cover: Agora’s History $API’s API China’s Livestreaming Boom What Agora Looks Like Today The Bull Case for Agora The Bear Case Against Agora Bull or Bear? Read the full piece at Not Boring.
April 19, 2021
Is BlockFi the Future of Finance?
The first question anyone has when they hear about BlockFi is: “What’s the catch? 8.6% APY sounds too good to be true. That can’t be legit.” I went DEEP to understand how they do it, and it’s legit. Essentially, BlockFi arbitrages the fact that traditional finance and crypto don’t like to deal with each other. We'll cover: What Does a Bank Do? What BlockFi Does Stablecoins and 8.6% APY Grayscale Bitcoin Trust The Race to the Finance Super App The Offer Read the full post at Not Boring. Sign up for BlockFi.
April 15, 2021
Unwitting Collaboration & Web3 Experimentation
I'm minting a Not Boring essay, Power to the Person, as an NFT, auctioning it, and splitting the proceeds with the people whose work I referenced.  In today's Not Boring, we discuss:  Chris Dixon's canonical pieces: The next big thing will start out looking like a toy (2010) and What the smartest people do on the weekend is what everyone else will do during the week in ten years (2013) A new media model that rewards quality over quantity and virality. Experimenting with Web3 You can read the full post at Not Boring, including a link to the NFT auction. 
April 12, 2021
A Not Boring Adventure, One Year In
Today, I'm sharing the Not Boring story as honestly as possible -- it often looks way easier from the outside -- with lessons I’ve learned on writing, growth, business models, investing, and creator psychology sprinkled in. We’ll cover: Getting Here: Per My Last Email → Not Boring Club → Not Boring Growth: Luck, Shares, Ups, Downs and Tommy The Writing Process and Psychology Business Model: Optimize for Growth and Opportunity The Not Boring Syndicate The Present and Future of Not Boring You can read the full post, including charts and a link to the subscription vs. ad model at Not Boring.
April 5, 2021
This is How They Tell Me Secureframe Saves the World
If you're building a software company, you need security compliance certifications like SOC 2 and ISO 27001 to sell into large companies. It sounds boring and tedious, but it's fascinating. The story involves: - Russian hackers unleashing malware called NotPetya on the world and causing $10 billion in damages. - How startups are selling into large enterprises and big pools of revenue much earlier. - How to compete and win in a massive, nascent, non-winner-take-all market with high switching costs. - Why you keep hearing about SOC 2 on Invest Like the Best and The Twenty Minute VC. Secureframe, founded by Shrav Mehta and Natasja Nielsen in 2020, just raised $18 million from Kleiner Perkins to make security compliance faster, cheaper, and more effective.  Read the full post at Not Boring Schedule a Demo with Secureframe
April 1, 2021
We Good Now?
In this episode, Dror Poleg and I break down WeWork after the recent announcement that it's going public via SPAC at a $9 billion valuation.  We cover: The Royal We. Adam Neumann was narcissistic and brash… exactly what was needed to shake up office real estate. WeStory. From 3,000 sq ft in Soho to millions across the world, fueled by an epic hype flywheel. From WeWork to We. Neumann pushed the company outside of office and into a little bit of everything. IPOh No! WeWork’s attempted 2019 IPO failed spectacularly thanks to unforced errors, and the company brought in new management, refocused, and trimmed down. WeSPAC. On Friday,Vivek Ranadivé’s BowX SPAC announced that it’s taking WeWork public at a $9 billion valuation. Side Note: Masa is a Genius Again. Masa is on a tear. WeWork breaking even would be the icing on his comeback cake. WeWork by the Numbers. The refocused WeWork is a straightforward business. The WeWork Bear Case. This time, maybe it’s the market’s fault. The WeWork Bull Case. WeWork survived, erased its mistakes, and is perfectly positioned to capture value in a more flexible world. Back to the Future. You know who would have been a perfect CEO for this market? Read the full piece on Not Boring.
March 29, 2021
What's On Deck for On Deck?
Today, On Deck is announcing that it’s raising a $20 million Series A led by Keith Rabois at Founders Fund with participation from Learn Capital, Chamath Palihapitiya, Slack Fund, Village Global, Eric Yuan, Fred Ehrsam, Allison Picken’s The New Normal Fund, Charles Hudson at Precursor Ventures, Adam D’Angelo, Jen Rubio, Elad Gill, Julia DeWahl, Henry Ward, Afton Vechery, Jules Walter, Eric Su, Julia Lipton, Scott Belsky, Anthony Pompliano, Bloomberg Beta, Dylan Field, Aarti Ramamurthy, and many, many more members of the On Deck community. We cover why On Deck has a chance to build a Stanford for the internet: On Deck Investment Thesis. Natively Integrated Education. Platform and Team Constellation. The On Deck Opportunity. You can read the full original post and subscribe at
March 25, 2021
The Dao of DAOs
DAOs - Decentralized Autonomous Organizations - are the next stop down the Web3 rabbit hole after NFTs.  We explore:   - The DAO's $6.6b Hack  - What's a DAO?  - Coinbase vs. Uniswap  - $UNI vs $SUSHI - Progressive Decentralization  - 7 Powers Analysis  - The Future Read the full post at Not Boring.
March 22, 2021
Soundtrack the World
Epidemic Sound just raised $450 million at a $1.4 billion valuation to Soundtrack the World. Spotify's Stream On event showed the company is ready to do battle with the labels.   The time is right: Spotify should acquire Epidemic. We cover:  Spotify’s Problem with Labels Spotify Streams On Enter Epidemic Sound Spotify x Epidemic Read the full post at Not Boring.
March 15, 2021
UserLeap & Differentiating Insights
UserLeap helps product teams continuously discover customer needs and evaluate the user experience via short, highly targeted surveys (microsurveys) displayed contextually within the product. Companies use UserLeap to track NPS, iterate toward Product-Market Fit, improve onboarding, reduce churn, and make the myriad small improvements that make a great product. The magic of UserLeap is that it quantifies qualitative feedback by collecting rich, written responses, in real-time, and using machine learning to analyze and categorize the responses to pull out themes. In today's Sponsored Deep Dive, we cover:  The Need for Speed The Modern PM Tech Stack vs. User Research Tools Meet UserLeap Building Moats in a Competitive Market UserLeap’s Vision: The Two KPIs Read the full post at Not Boring. If you're a product manager, user researcher, or anyone at a company with a website who works with customers, try UserLeap for free.
March 11, 2021
Not Boring Interview with BidOps Founder Edmund Zagorin
Edmund Zagarin is the co-founder and CEO of BidOps, a startup building strategic sourcing software powered by AI. We discuss the global supply chain, how survey design informs good procurement software design, and how college debate informs the way that Edmund approaches running a startup. Of course, we start out by asking Edmund to convince us that procurement is not boring.  If you want to learn more about the intersection of AI and procurement, check out BidOps' March 24th conference, Optimal.
March 9, 2021
Excel Never Dies
Excel may be the most influential software ever built. If you want to see the future of B2B software, look at what Excel users are hacking together in spreadsheets today. Excel’s success has inspired the creation of software whose combined enterprise value dwarfs that of Excel alone. There are two main ways Excel has set the broad roadmap for the B2B software industry for decades, and will continue to for years to come: The Unbundling of Excel. Hundreds of B2B startups have been built by taking a job currently being done in Excel and trying to accomplish the job in more optimized, purpose-built B2B software. Every time you hear an entrepreneur say, “We’re replacing siloed spreadsheets and outdated processes with purpose-built software,” you’re hearing the Unbundling of Excel in real time. Many popular SaaS applications fall in this category. And yet, despite being “unbundled,” Excel keeps getting stronger. Inspired by Excel. That resiliency has inspired entrepreneurs to look more deeply at what makes Excel tick, and why. Adventurous builders are creating new software that doesn’t unbundle Excel, but is Inspired by Excel. Excel’s balance of usability and flexibility can be found in popular no-code and low-code products created over three decades since Excel first graced the screen. This source of inspiration is less direct and more meta; it is less about recreating anything concrete that happens in Excel, and more about capturing the essence of what makes Excel so successful. We love Excel, everyone reading this probably loves Excel, and still, its impact is deeply underappreciated. Ben Rollert and Packy team up to cover: The History of Excel Excel as a Language The Lindy Effect Excel’s Limitations No-Code and the Unbundling of Excel Why Excel Will Never Die Read the original post at Not Boring. The audio edition is brought to you by Masterworks. Use promo code "not boring" to skip the 25k person waitlist.
March 8, 2021
Jack of Two Trades
Why is Jack Dorsey so much worse at being the CEO of Twitter than he is at being the CEO of Square? Marc Rubinstein and I teamed up to tackle that question, and came away thinking that maybe Jack doesn't run the two companies so differently after all. We cover: Jackground Back to Square One Putting the Network Into Square Old Twitter Twitter’s New Groove Back to the Original Question You can read the full post on Not Boring. Marc Rubinstein is a former financial sector-focused hedge fund manager who writes one of the best financial sector newsletters there is: Net Interest. Marc has written about everything from newer players like Ant Financial and Facebook’s Diem, to huge banks like Citi, to explainers on things that only industry insiders would know. You should subscribe now if you’re interested in … money. Subscribe to Net Interest
March 1, 2021
Beacons: Not Boring Investment Memo
Beacons is building a link in bio into a competitive space, and I think it's going to win. The link in bio is the point of leverage in the Creator Economy value chain, and Beacons' early growth indicates that they are building something that stands above the rest. In this episode, we cover: Meet Beacons The Creator Economy Value Chain and the Multi-SKU Creator Competition, Growth, and Moats The Beacons Vision and Opportunity Risks You can read the full post at Not Boring.
February 25, 2021
Power to the Person
It's been a wild month for the Passion Economy, crypto, and NFTs. While it feels frothy, and certain asset prices certainly are, I think it points to a larger future. This episode is a thought experiment based on three ideas: A main Not Boring theme that Genies don’t go quietly back into bottles. Chris Dixon’s famous line that “the next big thing will start out looking like a toy.” Ben Thompson’s idea that media businesses are the first to adapt to new paradigms because of their relative simplicity, and others follow later. The Creator Economy and NFTs are massive human potential unlocks. Even if certain assets are in a short-term bubble, we are on an inexorable march towards individuals mattering more than institutions. We’re on the precipice of a creative explosion, fueled by putting power, and the ability to generate wealth, in the hands of the people. Armed with powerful technical and financial tools, individuals will be able to launch and scale increasingly complex projects and businesses. Within two decades, we will have multiple trillion-plus dollar publicly traded entities with just one full-time employee, the founder. We'll cover:  Creators’ Crazy Month The Creator Toolkit Coase and the Nature of the Firm The New Nature of the Firm The Age of Individual Influence To read the original piece, head over to 
February 22, 2021
Not Boring Interview with AltoIRA CEO Eric Satz
AltoIRA makes it easy to invest in alternative assets like startups, real estate, private equity, and even crypto, all through your IRA.  I sat down with Alto's CEO, Eric Satz, to talk about why he started Alto, what they're building, and what he wants the CEOs of Southwest and BlackRock to say about Alto in the future. To learn more and sign up for Alto, use the Not Boring link and an Alto team member will guide you through the process. Read the full sponsored deep dive over at Not Boring.
February 18, 2021
Dreams All the Way Up
It feels like we're in a tech bubble, but what if I told you that the best startups and non-FAAMG public tech companies are actually undervalued?  In today's Not Boring, we cover a different way of looking at tech valuations, not P/E, P/S, or FCF Multiple, but Price/FAAMG, or the probability that younger tech companies can become as big as today's biggest. From that perspective, they're cheap... Amazon and Facebook have outgrown startup valuations at every stage over the past decade.  Read the original and check out the charts and graphics at Not Boring. 
February 15, 2021
The Beginning of the End
In this not boring guest post, Dan Teran, founder of Managed by Q and early stage investor, argues that while the pandemic looks like a boon to third-party food delivery companies, it's actually the beginning of the end. He weaves together strategic frameworks from Porter, Christensen, and Peter Drucker, plus actual restaurant data, to show that the current, integrated model is unsustainable, and that third-party food delivery is going to be unbunbled.  Follow Dan on Twitter and Medium. Read the full post at Not Boring. Thanks to our sponsor, OpenPhone, which is building the business phone, reimagined. Check out OpenPhone to set your team up with professional phone numbers and an experience that is so much better than Google Voice. 
February 11, 2021
How Twitter Got Its Groove Back
Twitter is getting its groove back. Smart acquisitions and product development, in addition to foundational work that the company is doing, might change the bearish narrative that's surrounded the company for half a decade.  We cover:  Prof G vs. Twitter. Scott Galloway ripped the company and its CEO, Jack Dorsey, last week. It’s a good summary of the critics’ view, and a bullish signal. If I Ruled the Tweets. Twitter needs to focus on its power users and make products that help them share their ideas and make money. How Twitter Got Its Groove Back. Twitter grew usage, improved its ad product, and survived the election. Now it’s focused on what’s next with the acquisition of Revue and launch of Spaces. Twitter’s Creator Bundle. Twitter is in the best position to build or buy a bundle of tools for Creators. Plus, why I think it can beat Substack and Clubhouse. Changing the Narrative. Adding up the sum of Twitter’s parts. Read the full post at Not Boring
February 8, 2021
Selling a Lot of Shares a Little Too Early with Brett Beller (ex-Drizly)
Brett Beller, my good friend and former Breather co-worker, was the first employee and practically co-founder at Drizly, which just sold to Uber for $1.1 billion. Brett tells the stories from Drizly's earliest days, goes deep on liquor laws, talks about why he sold a bunch of his shares a couple years ago, and walks through the emotional rollercoaster of learning that his company sold for $1.1 billion.  Brought to you by Secfi, which helps startup employees make smarter decisions about their equity.
February 5, 2021
Supersapiens: Not Boring Memo
Supersapiens is energy management for athletes. It provides continuous glucose monitoring (CGM) via a biosensor and app, in partnership with Abbott. That partnership is a cornered resource that gives Supersapiens tremendous power.  Over the past year, wearables and connected fitness tech have been on fire. Google bought Fitbit for $2.1 billion, Lululemon bought Mirror for $500 million, and WHOOP raised $100 million at a $1.2 billion valuation. I think that Supersapiens will be the next to join that group.  In this not boring investment memo, we cover:  Wearables and CGM Supersapiens Story and Product The Abbott Agreement Targeting Athletes (and Everyone is an Athlete) The Supersapiens Team Business Model and Early Traction Risks Opportunity To read the full post, and learn more about the opportunity, go to Not Boring.
February 4, 2021
Robinhood Robinhooded Robinhood
If you've been wondering what's going on with GameStop, WallStreetBets, and Robinhood, I got you. This was inevitable once Robinhood introduced free options trading. Robinhood bet that it could introduce tremendous amounts of risk into the financial system, push all of it onto its users and the market at large, and insulate itself from the consequences. And it would have gotten away with it too, if it weren’t for those meddling kids! Read the full piece on Not Boring. Brought to you by Future: join our 21 workout challenge.
February 1, 2021
weSPAC: Understanding WeWork with Dror Poleg
Dror Poleg, the author of Rethinking Real Estate, a good friend, and one of the longest-standing WeWork rationalists I know joins the not boring podcast on the heels of the WSJ report that WeWork may go public via SPAC. We discuss:   - WeWork's history, from 2010 founding to failed IPO  - Adam Neumann and SoftBank's Masayoshi Son  - WeWork's business model, competitive advantage, and challenges  - Why WeWork is healthier coming out of COVID than it was coming into it   - Whether WeWork will be more valuable than Airbnb within two years  - THE WEWORK SPAC and whether we're buyers at $10 billion.  Follow Dror on Twitter and at 
January 29, 2021
Podcast Discovery Reinvented: An Interview with Co-founder & CEO Doug Imbruce of Podz, Acquired by Spotify
Podz is revolutionizing audio - the very format you're listening to right now - by using machine learning to solve the seemingly intractable audio discovery challenge. I sat down with Podz CEO Doug Imbruce to discuss building social apps, selling his first company to Yahoo!, the state of the audio landscape, and how Podz is going to bring some order to the chaos.  Download Podz now to try it out and fill out the beta survey to help the team improve the audio experience! Follow @ListenToPodz on Instagram and Twitter.  Read the full essay on Not Boring.
January 28, 2021
The Value Chain of the Open Metaverse
You’re going to be hearing a lot more about Web3 (including DeFi), NFTs, and the Metaverse, so today, we'll try to define them and figure out how they fit together.  What is Web3 and Why is it Important? Non-Fungible Tokens and Digital Ownership. NFTs in the Wild. The Size of the Metaverse Prize. The Open Versus Closed Metaverse. Crucible and The Direct-to Avatar Economy. The Value Chain of the Open Metaverse. You can read the full piece here.
January 25, 2021
Masterworks: Demystifying & Democratizing Art
Masterworks is making blue-chip art, a $1.7 trillion asset class with strong returns, low volatility, low correlation, and increasing scarcity, investible.  Listen to learn about the art market, the most expensive painting ever sold, what makes art valuable, and how you can invest in art with Masterworks.  And if you want to explore for yourself, sign up for Masterworks with this link to skip the 25k person waitlist: Try Masterworks Read the full piece at Not Boring
January 21, 2021
Antara Health: Natively Integrated Healthcare
Antara Health is a HealthTech startup based out of Nairobi, Kenya that is building virtual-first primary care for emerging markets.  It’s reimagining healthcare by leveraging telemedicine, data science, and emerging markets payors’ and regulators’ willingness to try new models. When they succeed, they'll help close the insurance gap in the emerging markets, deliver better healthcare to the billion new members of the global middle class, and extend and improve lives. In this Not Boring Investment Memo, we'll cover:  Extending and Improving Billions of Lives. Billions of people in emerging markets are uninsured, creating a vicious cycle in which illness leads to poverty. Radical Changes to a Massive Market. COVID made telehealth more prevalent worldwide, creating an opportunity to radically rethink healthcare. Antara: Natively Integrated Healthcare. Antara combines Health Navigation, telehealth, and data in a Natively Integrated approach to healthcare. Strong Early Traction. Antara completed a successful pilot in Kenya that showed strong engagement, scalability, value, and effectiveness. Antara’s Business Model. Healthcare doesn’t have to be complicated. Antara’s model generates recurring revenue, and it uses technology to lower costs as it scales. The Antara Team. The Antara team is world-class at exactly the things they need to be to reimagine virtual-first primary care company for emerging markets. You can read the full essay at Not Boring: Antara Health on Not Boring
January 18, 2021
Teamflow: Not Boring Memo
Teamflow is a virtual office that makes remote work work. Led by Flo Crivello, a former Uber engineer who launched Uber Works and gig charging for Jump, Teamflow brings back the presence of being in the office, the energy of working in the same room, the spontaneity of hallway conversations — the joy of feeling like a team. Forget Zoom. Teamflow is what remote work should feel like.  The way Flo and the Teamflow team are building is full of lessons for entrepreneurs. Learn how they're building in Zoom's virality with Slack's moats, for example, or how Flo spent two months of 13-hour days recruiting his dream team.  Today, Teamflow is launching on ProductHunt. Go support them here: Teamflow on PH Sign up for Teamflow today, and use this link to move up the waitlist: Sign Up for Teamflow And read the full Memo here: Not Boring
January 13, 2021
Interview with Florent Crivello, Founder of Teamflow
Florent Crivello is the Founder and CEO of Teamflow, a virtual office startup that came out of stealth and announced a $3.9 million seed round led by some of the world's best early stage investors.  Flo and Packy discuss how a late night at Uber sparked the idea for Teamflow, hiring world-class engineers and designers, the intersection of strategy and execution, and how Teamflow is like the best parts of Slack and Zoom.  To sign up for Teamflow and move up the waitlist, join here: Sign Up for Teamflow Read the full investment memo at Not Boring.
January 13, 2021
BABA Black Sheep
Jack Ma is missing. $BABA is tanking. Ant Group's IPO is suspended. Government regulation (or worse) looms.   But Alibaba continues to build an underappreciated, customer-centric juggernaut.   There's never been a better time to go deep on Alibaba. This week's audio edition is brought to you by You can read the full original post on Not Boring.
January 11, 2021
New year, new me. For the first Not Boring of 2021, we're doing our first bear case.  Bill dot com is the worst software I use to run Not Boring, & trades at the highest rev multiple of any BVP cloud stock.  In 2021, bad B2B UX doesn't cut it anymore. We cover:  1. What is  2. The bear case.  3. The Love-Hate Relationship with Work Software. 4. Killing a Baby Dictator.  Read the full essay here:
January 4, 2021
The Best Is Yet To Come
After a wild 2020, I think the best is yet to come. We cover three reasons: The Markets Are Eating Up Technology. More demand for tech stocks means more innovation, more quickly. SPACs may be a good thing and IPOs unleash investment in the next generation. Cloud Companies. Entrepreneurs can build new types of highly-differentiated companies with global talent and increasingly useful software at their fingertips. The Passion Economy Writ Large. As software does more grunt work and employment becomes more liquid, people will pursue their passions. That will make them even more resilient the next time a crisis hits. You can read the full essay here: The Best Is Yet To Come
December 21, 2020
Ramp: The Card-Sized Finance Team in Your Pocket
Ramp is using its corporate card as a Trojan Horse into the CFO Suite, helping companies save time, money, and headache. Ultimately, it wants to help companies save money and build better businesses. Today, it announced that it raised $30 million and hit $100 million in transaction volume than any corporate card company in history.  Read the full essay here: Sign up for Ramp and get $500 free for being a Not Boring listener here:
December 17, 2020
Everybody Hates Facebook
We all hate Facebook, but Zuck and Co are building a juggernaut whose business is undervalued relative to all competitor sets and which is attempting to pull off some fascinating moves in communication, commerce, and potentially... the Metaverse.  Read the full post here: Everybody Hates Facebook
December 14, 2020
Outfit: Not Boring Investment Memo
Outfit is DIY Renovations in a box. Listen to hear the case for this early stage startup that's using software to scale architecture.  Outfit's Website Read the full post here: Outfit: Not Boring Investment Memo
December 10, 2020
APIs All the Way Down
APIs are all around us, powering the products we use and love every day. Chances are, you're passingly familiar with the concept but have never gone deep. When Stripe and Shopify announced that they were deepening their partnership last week - that Shopify would use another Stripe API, Treasury, I figured it was time to dive in. You can read the full post on Not Boring. We cover:  What Are APIs? The API-First Ecosystem Good Internet Strategy, Bad Internet Strategy Why Shopify is Smart to Build on Stripe and Twilio The Magic of API-First Business Models Twilio and Investing in API-First
December 7, 2020
We're Never Going Back
The future of work is remote. Companies that want to compete for the best talent don't have a choice, the employees do. Luckily, better software and new hybrid physical models are on the way so that life doesn't become a never-ending series of Zoom calls until we die. Read the full post here and subscribe!
November 30, 2020
FEMSA: The Most Interesting Company in Mexico
FEMSA is a 130-year-old Mexican brewery turned world's largest Coca-Cola bottler and the Americas' largest convenience store chain, plus a 15% stake in Heineken and a bet on the digitization of the Mexican economy.  I teamed up with Post Market to write about the company's history, present, and future, and why we think it's so undervalued.  You can read the full post here. 
November 23, 2020
Fairmint & the Democratization of Upside
In this collaboration between Sari Azout of Check your Pulse and Not Boring, we cover crypto, equity financing, and programmable money. Fairmint is making it possible for companies to sell or give equity to all of their stakeholders as easily as adding an "Invest" button on their website. That could reshape who shares in upside, and even what types of businesses are possible.  You can read the full post at
November 19, 2020
Slack: The Bulls are typing...
Slack's stock has been beaten down based on fears that Microsoft Teams is going to crush it and the fact that it hasn't benefited from WFH as much as Zoom. That narrative will break, and when it does, Slack will be valued like the top quartile SaaS company it is.  Read the full post here:
November 16, 2020
The Magic of Mushrooms
After 50 years in darkness, there's a psychedelic renaissance underway.   Psilocybin and other psychedelics may be our best weapons in the fight against mental illness.   There's even a publicly traded psychedelic stock: Compass.  Come take an auditory trip with me. Original post here:
November 9, 2020
Trust The Process
7.6 Lessons from Sam Hinkie and The Process, the Philadelphia 76ers innovative rebuilding process.  Read the full post here:
November 2, 2020
Pipe: Business-Funding Fit
Pipe solves Business-Funding Fit for recurring revenue businesses. The company created a new asset class, allowing businesses to sell their recurring cash flows to investors, often for $0.90-$0.95 cents on the dollar, to fund their growth without dilution or debt.  You can read the full essay at If you run or work for a business with recurring revenues, sign up to see how much Pipe can send you today at:
October 29, 2020
Software is Eating the Markets
The COVID-fueled rise of consumer investors may be here to stay, as spending shifts from things and experiences to investments, and new platforms allow users to invest in new and old asset classes with better user experiences.  Read the full post here:
October 26, 2020
SkillMagic: Not Boring Invest Memo
The Not Boring Syndicate is back with our fifth investment memo. Today, we're talking about SkillMagic, a startup building remote-native training for engineering teams. You can check out the full post at
October 22, 2020
Reliance's Next Act
The Indian conglomerate Reliance has historically vertically integrated, but it needs to loosen the reigns and become a growth stage investor to capture as much of India's growth in the next decade as possible.  Full essay at
October 19, 2020
Reliance: Gateway of India
Reliance Industries is the largest and most important company in India. It's also the best way for foreign companies to access the market.  Over the past six months, it has raised over $25 billion from investors like Facebook, Google, KKR, Saudi Arabia, Silver Lake, and Abu Dhabi for its Jio and Retail businesses.  Read the full post here:
October 12, 2020
Fundrise and the Magic of Diversification
Today, in this sponsored post, we're talking about Fundrise, a company that lets anyone invest in a professionally managed real estate fund through an app. We go deep on the company and why Ray Dalio is such a big fan of diversification.  You can read the original post and get all of the additional links I mention at 
October 1, 2020
Secure the BaaG: Business-as-a-Game
In this episode, we try to answer the question:  Would it be possible to run a real business in a way that feels like playing a video game? Check out the original essay here:
September 28, 2020
Special Edition: Not Boring Generalists
Every week, Mario Gabriele (the author of The Generalist) and I (the author of Not Boring) have a conversation and post it to YouTube under the Not Boring Generalists banner. We figured we'd put it here too, so you can listen while you walk, drive, or go to sleep.  This week we discuss:   - Our writing process  - Why everyone is becoming an investor  - Our favorite companies - What % of mammals we can outrun.  Enjoy! 
September 23, 2020
Opendoor: The Amazon of Real Estate
Chamath took Opendoor public via SPAC last week. In this episode, we talk about why Opendoor is the Amazon of real estate, its advantages over Zillow, and its flywheel.  Original post here:
September 21, 2020
MainStreet: Free Money for Startups
Today's Not Boring is all about a startups that sends other startups and SMBs free money: MainStreet. By getting you the tax credits and incentives that the government owes your company, MainStreet send companies $51k on average. See how much you're owed and get paid at You can read the full post at
September 17, 2020
Zoom's Blank Check
This week, we're doing a Case Study on Zoom.  - Its numbers are on fire.  - Its stock is overvalued. - It has no moats. If you're CEO Eric Yuan, what do you do to increase long-term shareholder valuer? Read the full essay and participate in the Case Study here:
September 14, 2020
Swaypay: Not Boring Investment Memo
Not Boring Investment Memos are deep dives into early stage companies that are raising money now. This week, we're talking about Swaypay, which gives shoppers discounts in exchange for using their social capital, or sway, to share products, all within the checkout flow. It takes money that would normally go to Google and Facebook and gives it back to regular people. I love that.  You can read the full post here: 
September 10, 2020
Masa Madness
A deep dive into SoftBank's history, the Vision Fund, and its new hedge fund, plus the bull, neutral, and bear cases. Read the full essay here:
September 8, 2020
Oze: Not Boring Investment. Memo
You can read out the original post here:
September 3, 2020
Stripe: The Internet's Most Undervalued Company
This week, we dive into Stripe, and cover:  What it is.  Why Stripe is undervalued. The Stripe bear case.  Stripe's underappreciated strategy. Stripe's future.  Link to original post:
August 31, 2020
Tencent's Dreams
Tencent's investments in Epic, Snap, Spotify, and more put it in the best position to bring about, and profit from, the Metaverse. Read the original essay here.
August 24, 2020
Tencent: The Ultimate Outsider
Tencent is the most impressive company that Americans know the least about. In Part I of this two-part series, we go deep on Tencent's history, its core businesses, and its investment portfolio. We also explore how the company is the perfect implementation of William Thorndike's The Outsiders. Link to original post here.
August 17, 2020
Shopify and the Hard Thing About Easy Things
Shopify and a new wave of ecommerce infrastructure tools make it easier than ever to start a direct-to-consumer business, but it's harder than ever to stand out from the crowd. Michael Porter's Five Forces and his value chain concept explain why it's a great time to be an ecommerce platform, and a hard time to generate sustained profits as a DTC business.  You can read the full post here.
August 10, 2020
JoJo's Juice
Ali Montag joins Not Boring to tell us about a Linear Commerce empire you wouldn't have any idea about, unless you have kids.  You can read the full post here and subscribe to Ali's newsletter here.  
August 6, 2020
Acquisition in G Sharp
Google should buy Slack to take on Microsoft with a modern solution in the productivity and collaboration space.  You can read the full post here.
August 3, 2020
Expanding the Talent Pipeline
The Marcy Lab School's Reuben Ogbanna takes over Not Boring to explain how we can explain the tech talent pipeline beyond traditional schools and backgrounds. You can read the full post here, and get in touch with me on twitter @packym to get intro'd to Reuben.
July 30, 2020
Juul - The SPAC 2020 Deserves
In this episode, we discuss what a SPAC is and why Juul is kinda the perfect company to go public via SPAC.  You can check out the full post here.
July 27, 2020
Composer - Not Boring Investment Memo
Not Boring Investment Memos are deep dives on early stage companies that are currently fundraising, and that the Not Boring Syndicate is investing in.  In this episode, we talk about Composer, which is aiming to close the wealth gap by giving investors access to more sophisticated tools for self-directed investing, with a clean, easy UI. Think of it like the best parts of Robinhood and Wealthfront, with a lot more muscle under the hood.  You can read the full memo here.
July 23, 2020
Entropy Theory
Entropy Theory explains industry evolution as a story of ever-increasing chaos and suggests that the most successful businesses are those that use the latest technology to wrangle that chaos, until entropic forces unleash the next set of opportunities. In this episode, we explain Entropy Theory through examples in real estate, tech, and employment. Why did TikTok succeed where Quibi failed? Why did Spotify take off while Napster got sued into oblivion? Entropy Theory is an attempt to explain.  You can check out the full post here.
July 20, 2020
Remember Ringtones?
Gil Kazimirov joins us to share the surprising  history of the ringtone - the polyphonic pocket music that launched the mobile revolution. You can read the full post here.
July 16, 2020
If I Ruled the Tweets
Twitter is the most undermonetized product in the world, because it doesn’t know what it is. For someone so into meditation, @jack’s lack of self-awareness is a surprising error with major implications. Twitter’s ads business struggles to support the entire company. Twitter doesn’t know who its customers are, or what its Job To Be Done is for them. Twitter captures almost none of the value that it creates. Creators are left without features they would happily pay for. Twitter Profiles are the most underdeveloped real estate on the internet. We dive into:  What’s wrong with Twitter and why? Who is Twitter’s customer and what is its Job to Be Done (JTBD)? What would Twitter look like if I ruled the tweets? You can read the full post here.
July 13, 2020