Hey, I'm Dan! I invest in early-stage startups at Madrona and write a weekly newsletter called the DL

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January 13, 2020
Looks like the future!
Looks like the future!

🛴 S-Pod - “The original Segway, which debuted in 2001, was supposed to replace walking. Obviously it didn’t.” Maybe the original Segway didn’t work out, but this thing looks amazing! Can’t wait to ride it around the office

🥾 Best hikes in every state - Outside Magazine says Yellow Aster Butte, Trail of Ten Falls Loop, and Hells Canyon are the best hikes in Washington, Oregon, and Idaho

💍 Best proposal of 2020 - Must-watch video of the week. Last month, some guy asked Reddit for help with his proposal and surprisingly it worked!

👪 Co-parenting startups - A couple of startups match people up who want to be co-parents but don’t want any romantic expectations. According to the WSJ, “It’s a lot like a divorce, without the wedding or the arguments.” Thoughts?

January 6, 2020


Intro to The Man Who Solved the Market
Intro to The Man Who Solved the Market

👨‍🏫 The Man Who Solved The Market - How crazy are those stats? $100B+ total profit, $7B annual profit, and only 300 employees. This book covers the history of Renaissance Technologies and its founder, Jim Simons. Not the best writing, but the story is pretty incredible

⚔️ Unicorns vs. Microsoft - Someone compared the return of investing in all unicorns vs. Microsoft over the last five years. Spoiler alert: Microsoft wins. Why invest in risky startups when you can just buy MSFT shares?

🏡 The Hype House - Twenty of the biggest TikTok stars just moved in together, and the NYT describes what it’s like. To get in, “you either have to be talented at something, or a weird funny mix, or extremely good looking.”

🍌 BANANA! - Not the Art Basel banana but just as good. Please turn on your sound and watch this 30 second video

December 30, 2019

📈 Y Combinator Trends - (1) YC is increasing batch sizes in line with seed funding trends, (2) YC is favoring enterprise over consumer, (3) AI, EdTech, and Healthcare on the rise; Hardware and Fintech on the decline

🇺🇸 American Dream - a 3M sqft mall with “so ambitious it has transcended the word ‘mall.’” Complete with indoor skiing, Nickelodeon theme park, DreamWorks water park, Legoland, a Vice-branded “Munchies” food hall, and a field hopping with live rabbits. Has anyone visited this place??

🇨🇳 Also the American Dream - Chinese immigrants are closing their family-run restaurants, but they’re happy because it means their kids are in professional jobs leading a less grueling life 😭

🥊 Twitter debate - True or false? “If you don’t work nights and weekends in your 20s, you’re not going to have a successful career.” Let me know what you think about this raging Twitter debate

December 23, 2019

🐾 Tracked - The NYT did a big investigation into the location data that companies buy about you. You should check out their visualizations - it’s pretty terrifying. One excerpt from the article…

We were able to track smartphones in nearly every major government building and facility in Washington. We could follow them back to homes and, ultimately, their owners’ true identities. Even a prominent senator’s national security adviser — someone for whom privacy and security are core to their every working day — was identified and tracked in the data

🤓 Focused - New startup in SF charges $40 to have someone watch you work. Starts with a consultation on what you want to accomplish and then a two and a half hour working session. Actually sounds like a pretty good idea… Let me know if you book a session!

💼 Career Launching Startups - Every year, Wealthfront publishes a list of tech companies that they recommend young people start their careers. It’s a pretty Bay Area-focused list but still interesting to look at


December 16, 2019
Green screens are so last decade
Green screens are so last decade

🚀 Fortnite x Mandalorian - Sarah and I finally watched the Mandalorian this weekend, and we love baby Yoda. Separately, here’s a cool article about Disney used Fortnite’s game engine to film a lot of the shots. They render imagery on LED screens and point a camera at the screens. Cool demo

🗣️ Ablaut reduplication - Fun fact. Whenever there are words/phrases with repeating sounds, the vowels always go I -> A -> O. Examples: tic tac toe, criss cross, dilly dally, King Kong. If you flip the words, they sound really weird: zag zig, hop hip, mash mish. Reddit explains why

👫 Virtual boyfriends - A growing trend in China is single women hiring ‘virtual boyfriends’ who text them throughout the day to chat and keep them company. Think there’s a market for this in the US?

👑 Job alert - Love The Crown? Love Instagram? Looking for a new job? The Royal Household is hiring a Head of Digital Engagement. Unfortunately, you’ll have to leave the PNW and work at Buckingham Palace

December 9, 2019
the ">" prompts are human input, and the rest of the story is written by AI
the ">" prompts are human input, and the rest of the story is written by AI
  • 🍽️ Sad times for Seattle restaurants - Ethan Stowell closing three restaurants, Tom Douglas closing his three spots in Via6, and Matt Dillon closing Sitka & Spruce. Is the Seattle restaurant bubble ending?
  • ⚠️ Away expose - “Never work for your dream brand.” Big investigation on the toxic culture at Away, the suitcase startup. Plus, a follow-up on how employees are barred from discussing the article and a separate follow-up on how VCs and founders feel about the news


December 2, 2019

👕 Digital clothing - I bet none of you bought digital-only clothing on Black Friday. How it works: you buy a digital sweater, send the company a picture of yourself, and they send your photo back with you wearing the sweater. Genius? Or insane? What do you think?

🎧 Naval Ravikant w/ Joe Rogan - Fantastic two hour podcast about how to design an amazing life in modern society with techie / philosopher / entrepreneur / guru Naval

📈 Startup financing trends data from Wilson Sonsini - Good reference from WSGR on median fundraising amounts, valuations, and deal terms

💑 John Legend and Chrissy Teigen - I love these two! Go read their Vanity Fair profile for a ton of great stories, like how John got his big break through a college roommate (Kanye West’s cousin), and how Chrissy is sad the second they land somewhere for vacation (because they’ll have to leave)


November 25, 2019

check out this demo to see how you can sub in different model's faces for each photo

📸 Generative.photos - Good domain name and very cool AI product that uses AI to generate realistic stock photos, and they’re free (for now)

👯 Improve Your Social Skills - This site was at the top of Hacker News last week. Sounds like a parody, but actually it’s a bunch of articles on how to build social skills from someone with Asperger’s Syndrome who had to methodically learn how to be social step by step. Interesting read

📖 The Dark Forest and Death’s End - Thanks to Philip S for these recs! If you read The Three Body Problem (China’s most popular scifi book) and thought it was good or even meh, please finish the trilogy! It’s SO GOOD!

😘 Dating market thesis - Here’s what you get when a hedge fund dude analyzes the online dating market for shifts in market dynamics and optimal dating strategies


November 18, 2019
🤮 are you kidding me, San Francisco?
🤮 are you kidding me, San Francisco?

💕 Here’s a much better love story - This is probably not even possible today because millennials can’t plan more than a year in advance, but that’s what makes the story so amazing

📺 In the Age of AI - Shoutout to new papa Alex Spencer who recommended this Frontline documentary on the AI race between the US and China and how it is changing the world. Great way to get up to speed on the latest in AI research and China’s tech scene

🔮 The future of the internet - In the US, when big companies want to undergo a “digital transformation,” they spend a lot of money on consultants. In China, they just get on WeChat. Here’s why the NYT thinks the future of the internet is “superapps” like WeChat

📡 The future of streaming - Is watching Netflix at 1.5x speed going to be the only way to get through all your shows on Netflix, Disney+, AND Apple TV? According to CNET, this is “the horror future we deserve” 🤣

November 11, 2019

📉 “WeWork problem” - VC Twitter has been dunking on the Softbank earnings deck, so no additional comment from me, but here’s a link to the actual slide deck so you can take a look for yourself

🛫 Why don’t rich people just stop working? - Rich people work longer hours and spend less time socializing. The New York Times digs into why

📺 How would a six year old spend $1000? - I loved this YouTube video - definitely worth nine minutes to watch a kid live out his dreams for a day!

👨‍💼 How VCs make money - This is the best article I’ve ever read on how VC firms are structured, charge fees, and create budgets


November 4, 2019

🚌 Trailhead Direct - King County’s hiking shuttle grew 75% this year to ~18K trips (though VCs are really hoping to see a triple at this stage 😝). But now funding is in jeopardy because of Tim Eyman’s I-976 - a tax cut Amazon, Microsoft, and Expedia are trying to prevent. Here’s a surprisingly interesting history of Seattle transit funding and Tim Eyman on Curbed

💵 Bitcoin’s 11th Birthday - Facts from Coinbase: 1 in 4 people with an MBA or PhD hold crypto, $240M of BTC was exchanged in Venezuela in 2019, and the supply of US dollars has increased by 36% per year since 2008

➡️ Doc.New - Google created a bunch of new “.new” sites, so now you can type commands directly in your URL bar like “doc.new” (starts a new Google Doc), “playlist.new” (new Spotify playlist), and “repo.new” (new Github repo)

🙌 Setbacks and success - New research paper says that failing (by a little bit) in the early phases of your career mean you will be more successful in the long run –> “Near-misses systematically outperform the narrow-wins”



October 28, 2019

🇺🇸 The American Dream - In the 1940s, 90% of children in the US grew up to earn more money than their parents; by the 1980s, this number dropped to 50%. The US is getting richer, but wealth isn’t distributed equally

👚 Stop buying clothes? - Morgan Stanley says that “consumers have reached peak happiness with clothing” because they already own too many clothes (the average person buys 65 clothing items per year)

💸 Speaking of family businesses… - Last week, Eric Tse (24 years old) became the world’s newest billionaire after his parents gifted him $3.9B of company shares. Check out his Instagram in this Daily Mail post

📚 Red Notice - A guy from Chicago becomes the largest private investor in Russia and gets on Putin’s bad side. It’s a true story that reads like a crime thriller. Definitely recommend!


October 21, 2019

🧻 Double < Triple < Jumbo < Mega < Mega Plus < Super Mega < Forever < Forever XL - The evolution of Charmin’s toilet paper rolls 🤣. Sh*t you not - you can now buy a 13.2" diameter toilet paper roll that will last you for months at a time! Buy it here (comes with a free stand)

📍 Seattle’s tipping point - Here’s a super comprehensive analysis from AI2’s Jacob Colker and Oren Etzioni on the five reasons the Seattle tech ecosystem is about to take off. Definitely worth a read

🎃 PCC Markets to Host Gluten-Themed Haunted House - Happy Halloween! (thanks to Liz Michiels for this link)

🤕 The next opioid epidemic? - 75% of Gen Z-ers and 50% of millennials have left a job for mental health reasons. And the big spike in mental health issues lines up with the time that the majority of people began to own smartphones. Seems like this could be the next massive public health crisis

October 14, 2019

🧠 The three stages of hearing about dopamine fasting - 1. ??? 2. lol 3. yeah I’d probably try this too tbh. 🤣 Here’s the link to learn more

💣 r/WallStreetBets - Speaking of Robinhood… this is my favorite subreddit. It’s dedicated to people making YOLO stock bets on Robinhood. Here’s one guy who started with $50K, made $600K on two trades, and then lost it all over the course of a week

⏲️ Seattle time-lapses - Time lapses of the Microsoft campus construction and the teardown of the Viaduct

🌊 Digital Gold - Best book on the history of crypto. Really exciting to put yourself in the shoes of the early adopters at the forefront of a new technology wave


October 7, 2019

🗽 “Making it in America” - What people think about their lives and where they are now vs. where they think they’ll be if they “make it”

📚 Becoming - Awesome book - highly recommend! This is a super inspiring, moving, and uplifting memoir from Michelle Obama. My favorite parts are when she explains her decision to “swerve” off the Princeton-Harvard-big law “path” and find work that’s meaningful to her and when she describes the sacrifices that both she and Barack made to enter politics and start a family (4.9 stars on Amazon w/ 15K+ reviews!)

🅿️ Optimal parking strategy - Science says… park in the first empty spot between two cars. This performs better than driving to the destination and backtracking to the first available spot or just taking the first empty spot

👏 Orlando Bravo - Movie star? Nope. The billionaire founder of Thoma Bravo, the tech-focused private equity firm. Forbes did a great profile on how he started investing in software and what’s driving his firm’s success


September 30, 2019

💸 How much do people at tech companies make? - Last week’s most popular link was Microsoft comp data, so I wrote a more detailed post on tech compensation vs. other high paying careers. Check it out on my new website! (with searchable archives for all DL posts)

The church of chicken - It only costs $10K to start a Chick-fil-A (vs. $2M for a McDonald’s) because they pay all the startup costs. This allows them to be very selective (0.15% acceptance rate) and find passionate community leaders to spread Chik-fil-A’s “gospel of hospitality and fried chicken”

🤖 $160,100 - Live auction price for a 2-story tall, giant battle robot. The owners spent $2.5M building it, but they went bankrupt and need to sell

🍣 “End of the Line” - Nice article (and pun) from Eater on the sudden end of Blue C Sushi, the conveyor belt sushi restaurant

September 23, 2019


💊 LSD vs. Asana - Is microdosing still a thing? Not sure - but in any case, you could also try Smartsheet for the same benefits 😉

☢️ Public service announcement - Most smartphones exceed legal safety limits for radiation exposure because companies test phones 5-25 mm from the body, even though most people carry their phones next to their body. Don’t carry your phone in your pocket!

🧬 Gene editing in Excel - One in five genetics papers has errors from using Excel because there’s a gene called SEPT2 which gets saved as Sept 2, 2016

🎒 $995 - Google and Saint Laurent collab on a connected backpack

💰 Rewards - Hundreds of Microsoft employees shared their comp details to a Google Sheet (haha) after bonuses came out. Here are the numbers


September 16, 2019

✈️ “Hit or miss?” - One of WhatsApp’s first marketing posts was Jan Koum asking FlyerTalk users to try a new app he built for people who travel a lot. Fun to read through because no one wrote back to him for four years!

🍾 Alibaba’s 20th anniversary gift - Super cool

🐙 $325M - Also super cool. The listing for Paul Allen’s yacht, Octopus

☀️ Caroline Calloway - “For some people on the internet, this article was akin to the Pentagon Papers or the Super Bowl.” If you enjoyed Fyre Fest, this is another “scam” happening live on Instagram. Here’s the story

👶 “AI-savvy” kids - According to the WSJ, if you want to raise an AI-savvy child, you should tell them to use the pronoun “it” when referring to a robot and explain that humans are the source of robots’ intelligence

September 9, 2019


Super excited for my first IMDB credit 🎬

🤖 Deepfakes – They’re back (again)! This time, it’s a Chinese app called ZAO that drops you into movie scenes

🤑 $225M pitch deck – Interesting to see what Sonder presented to investors for their $225M Series D

🔥 Hottest startups – LinkedIn measures how often non-employees view a company’s page and what startups people from top companies leave to join to put together a list of hot startups. This year there were three Seattle companies on the list (Amperity, Convoy, and Outreach). And #1 on the list (Snowflake) is a Madrona company as well!

👯 Bitcoin Billionaires – I’ve been looking for a book about early crypto investors, and this one is great. It follows the Winklevii after the Facebook settlement and tells the story of how they started investing in bitcoin


September 3, 2019

📚 The Tattooist of Auschwitz - I started this book Sunday night and finished it on Monday. Incredible story you should definitely read

💭 TL;DR: - Save yourself $200K for an MBA and just read these (surprisingly good) one sentence summaries of the 20 best finance books

🔄 Learning Loops - Blog post from Matt McIlwain on the entrepreneurial journey with stories from the early days of Smartsheet, Apptio, and Isilon

🚴‍♀️ Striking! - In honor of the Peloton IPO, here is one of the best Twitter threads ever. Amazing photos and commentary 😆



August 26, 2019
Cool photo of the viaduct from r/Seattle

🏢 WeWork IPO - Don’t worry! I’m not going to write another WeWork article. Just sharing a pointer to my favorite write-up on the IPO

🙎 49% - Deloitte says 49% of millennials will quit their jobs in the next two years. And the best new way to find your next job is become a ‘mintern’ (middle-career intern)

😊 PSYC 157 - Speaking of unhappy millennials… Yale’s most popular class ever teaches you how to be happy, and it’s free on Coursera

💰 Are you rich? - The New York Times has an interactive article that tells you if you’re rich. Apparently most people are (positively!) surprised by their results


August 19, 2019

My wife Sarah makes fun of me for not using Instagram, so this week I made my first Instagram post in three years and educated myself on Gen Z social. Here are some articles to get you up to speed, too:


📸 Insta-worthy? - According to the WSJ, emojis, bitmojis, and Tinder photos are making their way into Gen Z resumes. We just launched Madrona’s Instagram, so send your insta-worthy resumes my way!

🍦 $200M - The Museum of Ice Cream just raised $40M at a $200M valuation. From what I can tell, they actually do sell ice cream, they are not really a museum, and their Instagram looks really good

👯 Twinfluencers - As an only child, I can’t take advantage of this one, but apparently, 1 in 30 kids born in the US today is a twin, and they’re taking over social media

⚡ AP Pokemon - Someone on Reddit created a 42 page AP Pokemon exam, and it is really good. Unfortunately, no emoji for Pokemon (yet)


August 12, 2019

August 5, 2019

☝️ Special guest this week in the DL

Note from Dan: What do you do after consulting at McKinsey, redesigning NYC public schools, working in private equity, and then launching the Amazon Go stores? Go revolutionize the legal industry of course! Turning it over to Xiao here…


Hi everyone! My name is Xiao Wang and I’m the co-founder/CEO of Boundless Immigration, a Series A startup helping immigrants and their families through the complex government process at 1/5 the cost of traditional lawyers.


Besides maintaining our 100% government approval rate and figuring out how to successfully scale a fast-growing company, I love reading. Business, tech, outdoors, life, policy… my reading list is truly boundless (I’ll show myself out now).


I managed to parlay sharing that fascinating Cosmic Crisp story last week into taking over an entire corner of Dan’s weekly newsletter, so here you are for the first week of August!

  1. One writer’s experiment in drop-shipping sketchy swimsuits from AliExpress.
  2. What life as a delivery driver is like (with insights into how tipping actually works). Since this article, Doordash has updated its policies to be more driver-friendly, so score one for journalism.
  3. A brief history of money, as we prepare for our Libra overlords.
  4. Unsurprising to anyone who watched the bike-sharing art in China over the past few years, researchers at NC State concluded that scooters aren’t that great for the environment either. Can we solve the urban mobility problem while treating objects nicer?
  5. A little bit of history, a little bit of nostalgia, bivalves of the heart. What Ivar’s means to those who grew up in the Pacific NW.


Found them fascinating? Complete waste of time? Please email me at xiao@boundless.com if you have any comments or recommendations.


July 29, 2019

🍔 $BYND - Beyond Meat IPOed at $25 in May has nearly 10x-ed to ~$225. At this price, it’s worth more than 25% of the S&P 500, including companies like Campbell Soup ($10B revenue) and Conagra ($10B revenue). Beyond Meat’s 2019 revenue forecast? $210M. Their IPO lockup ends in ~3 months, can’t wait to see what happens

🌌 Cosmic Crisp - “Unprecedented,” “on steroids,” “off the friggin’ charts,” and “the largest launch of a single produce item in American history.” Fun read about WA state leading disruption in a totally different industry

🕹️ 2048 Blast - I just released my second ever mobile game on iOS and Android! Try it out, and let me know what you think!

July 22, 2019
  • 📺 or 👨‍🚀? - Kids in the US and UK want to become YouTubers when they grow up, while kids in China want to become astronauts. As a millennial, I’m thinking, “Why not both?” 🤷‍♂️
  • 📞"Can you send me some money?“ - Criminals are now using audio "deepfakes” to impersonate CEOs and ask for money transfers
  • 😃 Emojis - There is a 12 person committee that decides what becomes an emoji, and you can look at all the applications they get. Here’s the one for the sloth emoji (yep, they reference Kristen Bell)
  • 🎧 Bill Gurley podcast - This is a conversation between one of the best interviewers and one of the best VC investors ever. Learn all about network effects, marketplaces, and IPOs. Highly recommend

July 15, 2019
  • 🎂 Startup success calculator - According to this study, founders of the fastest-growing tech companies are 45 at the time of founding their companies
  • 🙈 7.4 min - Average amount of time it takes someone on a streaming service to find something to watch. Also, older people find stuff quicker. Just another skill that gets better with age? 😜
  • 📺 $9M soap opera blog - I love The Hustle’s daily email, and they just started a podcast. This episode is about a guy who made $9M selling a blog about soap operas, even though he’s never watched a soap opera in his life. It’s a fun headline but turns out the backstory is actually just lots of hard work building expertise in digital marketing
  • 🦄 My Prime Day pick - “I imagine Amazon will be receiving many orders from ours being seen in person”

July 8, 2019
  • 🤔 If you have no idea what any of this means, neither did I. Learn about some internet memes and inside jokes on this great ReplyAll podcast and feel connected to Gen Z!
  • 📦 Apparently Amazon ships nearly half of its own packages (48%) now, up from ~20% in January 2018. Also surprisingly, FedEx has only ever shipped 1-2% of Amazon’s packages.
  • 🙈 Deepfakes are back (NSFW), with an app called DeepNude. The app took a clothed photo of someone and used AI to make them appear naked. The app’s creator quickly pulled it after receiving a lot of criticism, but clearly this is now commodity tech that many people can build. We will see how the internet as a whole continues to police this kind of stuff - doesn’t seem like social pressure will work forever.

July 1, 2019

📚The Sun Does Shine - This is a crazy story about an amazingly inspiring person named Anthony Ray Hinton - and how he was unjustly sent to death row, how he managed to stay optimistic and survive with the help of loving friends and family, and ultimately how he was able to prove his innocence after 30 years on death row.

⚔️ In case you were wondering… HBO was able to retain 84% of new subscribers who signed up during the latest season of Game of Thrones. Pretty impressive considering how bad this season of GoT was.

💰Bitcoin! It’s back! Or it’s not back – kinda depends on the day. In any case, it’s pretty funny how over the last year, bitcoin prices are highly correlated with the price of avocados 🥑 (#millennials). Here’s the chart from Bloomberg.

June 24, 2019

📚 Rocket Men - Awesome book. This is one of those 5 full stars on Amazon type books. I didn’t know much about the Apollo space program before reading this, but this was amazing – such a well-written set of stories about the people behind the Apollo missions and how they got to the moon

🍔 Beyond Meat ($BYND) - If you haven’t tried the burgers yet, you should! I didn’t think they were very good. The stock price, on the other hand, is fascinating. This company IPO-ed at $25 and is now trading at $150+. Their revenue forecast for 2019 is $210M and their market cap is ~$8.5B (that’s a 40x+ multiple for a company with 20% gross margins 🤮). For reference, Tyson Foods does ~$40B of annual revenue and is worth ~$40B. If you’re thinking about shorting, though, watch out. Lots of people are thinking the same thing, so the cost to borrow shares to short is 125%+ per year

💰 Facebook Libra - Just so I can end issue #1 on something controversial - I really like this project. It’s a great demonstration of blockchain’s #1 benefit - the ability to pull a group of people/organizations together, that might not otherwise work together under a centralized hierarchy. Who knows if this will work, but I’m excited to see what happens


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