Hey, I'm Dan! I invest in startups at Madrona and write the DL, a weekly newsletter about tech in the Pacific Northwest

Featured Posts

Find Stuff

Built with Webflow

All Articles

DL Reader's Baby Advice

ICYMI last week we had a special DL announcement: Sarah and I are expecting a baby boy next month! I solicited baby advice from DL readers, and here is the collective wisdom in case you're curious:

Read more...

What Dan's Talking About

Dan's weekly summary of interesting articles, great books, cool videos, and internet memes

Read more...

Seattle Unicorns

All of the Seattle unicorns founded since 1994 (when Amazon was founded)

Read more...

Three Areas I'm Investing In

In case you’re wondering what themes I’m most interested in right now, here are three areas where I’m excited to find and fund new startups:

Read more...

August 2020 PNW Venture Deals

Here are the PNW startups that announced new fundraising rounds in the month of August. These 23 companies raised more than $350M last month!

Read more...

Request for Help!

Special announcement 🎉: Sarah and I are expecting a baby boy next month!

Read more...

First Seattle IPO Led by a Female CEO

Over the last 20 years, 77 companies in Washington state have successfully completed IPOs, but none of them had a female CEO.

Read more...

“I’m not a bonus and salary guy”

Back in July, SoftBank set up a new fund to invest in public equities, and it’s doing very well. So far, they have purchased $4B of call options on tech stocks, and they are up ~100% on their investment. 😲

Read more...

Big Week for Tech Investors 🤩

Was last week the best week of the year for tech investors? Not only was it YC Demo Day, but a bunch of tech startups filed to go public as well! Here are some links and articles to get caught up on all of the excitement:

Read more...

People Like Living in Seattle More Than SF

Based on anecdotal research and close observation of Zoom backgrounds, everyone without kids has left San Francisco to live in random places around the country. And here’s data from Zillow backing that up!

Read more...

Best New Amazon Product

So last week Amazon came out with a couple new products:

Read more...

🏇 Honestly not a very close race

Back in July, I asked readers which company would hit $2T first, and 90%+ of you said Amazon or Microsoft. Well, looks like we were wrong because Apple was the first company to cross the $2T mark last Wednesday.

Read more...

Back to growth mode?

When the pandemic first hit in March, many startups and VCs were ready for “The End.” However, over the last five months, not only have companies like Apple hit new highs, startups like Brex and Airbnb are seeing...

Read more...

Is Amazon Bad at Creativity?

Imagine spending ~$100M over five years to build and launch a “triple-A” video game. You give it away for free, but one month after launch you have <300 players. That’s what happened earlier this year with Crucible...

Read more...

COVID Activites

If you’re looking for a reason to head to Bend next month… Today at 1pm, the last Blockbuster is opening up the opportunity to book a sleepover inside their store:

Read more...

Inc 5000 PNW

Last week, Inc published their list of the 5,000 fastest growing companies in the country. There were ~190 PNW companies on the list, which feels low, but most of the companies aren’t really “startups,” so it’s not as West Coast..

Read more...

July 2020 PNW Venture Deals

Here are the PNW startups that announced new fundraising rounds in the month of June. These 23 companies raised more than $500M last month!

Read more...

31 Portland Startups

Cool project from Portland entrepreneur, Mark Grimes, who is challenging himself to launch 31 startups over 31 days in the month of August.

Read more...

Real Estate Craziness

One of my pandemic hobbies is browsing Redfin and Zillow to see what kind of house I could buy if I didn’t live in downtown Seattle. Of course, everyone else had that idea, too, so home sales are going through the roof.

Read more...

Five Years of PNW Venture Capital

I’ve been at Madrona for five years now, which means I’ve finally reached a kindergarten-level understanding of startups and investing! 🥳 In celebration, here’s a look back at how the PNW startup market has changed over those fiv

Read more...

Microsoft's #WashingtonCheck

OK, so what could make the PNW tech ecosystem even hotter? Microsoft acquiring TikTok! Lots of interesting details came out about this deal over the weekend:

Read more...

+1 🦄

Another one! Last week, Remitly announced an $85M Series F that valued the company at $1.5B, making Remitly the 38th PNW unicorn! In case you don’t know much about the company, here’s a quick summary:

Read more...

A-Cloud PRFAQ

To help address the problem of how concentrated Amazon’s power is, Tim Bray wrote a PRFAQ describing how Amazon might spin off their AWS business. If you’ve ever wondered what an Amazon PRFAQ doc looks like, check it out.

Read more...

Shoutout to the GeekWire Award Winners!

Hope you all tuned in to a fantastic virtual GeekWire Awards last week! Congrats to…

Read more...

Investors love SPACs

This is a big year for SPACs (special purpose acquisition companies). The way a SPAC works is…

Read more...

Madrona's Investment Themes

Over the next few weeks, Madrona is publishing our 2020 investment themes. We expect to see significant growth in these areas over the next five to ten years and are searching for new investment opportunities...

Read more...

+1 to the PNW Unicorn Tracker 🦄

The PNW got its newest unicorn last week, as Qumulo raised a $125M Series E at a $1.2B valuation! This is the 37th startup (according to The DL’s unicorn tracker) to reach a $1B+ valuation in the PNW...

Read more...

Survey says... long $AMZN!

Last week, I pointed out that the tech stocks are hitting all-time highs and asked you to predict which one would hit a $2T and $10T market cap first.

Read more...

Seattle's First IPO in 2020 🎉

Accolade went public on July 2, and it was Seattle’s first IPO of the year! Geekwire wrote a great article on the IPO and interviewed Accolade’s CEO, Raj Singh.

Read more...

Slack vs. Microsoft

Stratechery wrote a great article this week on the future of Slack. He starts by going back to that time Slack took out a full page NY Times ad to throw shade on Microsoft Teams (and points out that now Teams has 75M DAUs, while S

Read more...

June 2020 PNW Venture Deals

Here are the PNW startups that announced new fundraising rounds in the month of June. These 20 companies raised more than $1.1B last month!

Read more...

Vancouver, WA on the front page of Reddit 👏

Of course, Reddit was quick to point out that Batman’s mask doesn’t cover his mouth or nose. 😆

Read more...

What's next for M&A?

Here’s a cool chart from The Economist showing all of the deals that the big tech companies have done over the last decade. Interestingly, the last three multi-billion dollar acquisitions were all Microsoft and Amazon deals.

Read more...

Low Code / No Code / Honey Code 😍

Last week, Amazon released Honeycode, a new service that lets people build apps without writing code. (btw, check in with The DL’s favorite “VP in Purgatory” to get his take on the name)

Read more...

Another weird name from Amazon

Amazon renamed KeyArena… and while Climate Pledge is a good name for an investment fund, it’s a weird name for an arena. Add your ideas on better names to Geekwire’s Twitter post. I’m a fan of AWS Hockey Availability Zone.

Read more...

Microsoft nixes Mixer, partners with Facebook Gaming

In a confusing set of press releases, Microsoft and Facebook announced that Microsoft is shutting down Mixer and moving the Mixer community over to FB Gaming. After July 22, Mixer.com will redirect to fb.gg.

Read more...

And on the second day...

Earlier this year, The Economist wrote an article on how Seattle is the new epicenter of the tech world as products and business models move away from ads towards subscriptions, e-commerce, and cloud infrastructure.

Read more...

👊 Go Docusign!

After its IPO in 2018, Docusign traded around $40-50 per share, and today it’s trading at over $160, giving it a market cap of ~$30B. Thanks to this growth, Docusign is officially becoming part of the NASDAQ 100 (100 largest compa

Read more...

+1 for Vancouver! 🦄

PNW startups are pretty understated relative to their Bay Area peers. So it’s amazing to see a ~$20B company in Vancouver (WA) go public with so little fanfare that Techcrunch wrote, “The ZoomInfo IPO slipped through our fingers i

Read more...

Inside an Amazon Distribution Center

The NY Times visited the Amazon fulfillment center in Kent to take a tour and see what measures the company has rolled out to protect employees from coronavirus, including a testing lab where employees will be tested for COVID eve

Read more...

Best Way to Announce a New Job?

Geekwire wrote a couple of in-depth articles last week on Brian Hall, a marketing executive who left AWS to join Google Cloud. Basically, he left Amazon in March, started at Google in April, and Amazon filed a lawsuit alleging he

Read more...

Learn, Speak Up, Do Something

Black Lives Matter. There are so many powerful stories, essays, and videos to describe how the Black community feels right now, and it’s impossible to read and watch without feeling heartbroken and outraged.

Read more...

Zoom Crushes; Bill Gurley Called It in 1994

Zoom hosted their Q1 earnings call last week, and they announced $328M in revenue - compared to analyst estimates of $202M. Apparently, this is the largest beat vs. consensus estimates in the history of enterprise software.

Read more...

May 2020 PNW Venture Deals

Here are the PNW startups that announced new fundraising rounds in the month of May. These 18 companies raised ~$340M last month!

Read more...

What It Takes to Become a Soonicorn

Last week, Forbes published a list of the 25 “Next Billion Dollar Startups.” What are the overall trends and stats for which companies made the list?

Read more...

Disrupt yo self! 💥

It’s really interesting to see corporate strategy play out in this era of technology and innovation because innovators are willing to take gigantic bets and disrupt themselves...

Read more...

Why VCs love SaaS businesses

VCs love SaaS businesses because most public SaaS companies need less than $1 of capital to acquire $1 of ARR. Here's how SaaS capital efficiency compares to other types of businesses

Read more...

Microsoft Build Highlights

Microsoft hosted their annual developer conference, Build, as a 48 hour virtual event last week. You can watch all the keynotes and sessions here on-demand and read their announcement summaries here.

Read more...

How to Sabotage Your Company

One of my favorite “mental models” is inversion. When you’re making a decision, instead of figuring out how to do something, figure out all the things you shouldn’t do and avoid them.

Read more...

Vogue x Amazon

Wow - fashion in Seattle! Vogue x Amazon is a real collab! A couple weeks ago, they launched “Common Threads,” an Amazon storefront to support independent American designers who have been impacted by COVID.

Read more...

Quibi Quotes

If you haven’t downloaded Quibi yet… don’t worry about it. No one else has either. Despite raising $1.8B and launching with content from JLo, Lebron, and Steven Spielberg, they only have 1.3M active users...

Read more...

The Future of EdTech

Scott Galloway wrote a great piece on the future of education in NY Mag, and instead of just naming startups building personalized education tech, he says:

Read more...

Is Tech's Balance of Power Shifting?

Last week, The Economist published an article arguing that the pandemic is shifting the balance of tech power from SF to Seattle because of “a new era of subscriptions, e-commerce, and business infrastructure.”

Read more...

List of Seattle Venture Capital Firms

Here's a list of venture capital firms and other investors who are based in Seattle or the Pacific Northwest:

Read more...

Founders’ Co-op Deep Dive

Founders’ Co-op was founded in 2008 and has invested in 100+ startups. They target $250-750K seed investments in PNW startups, and last year, they closed a $25M fund. One cool piece of their history is...

Read more...

Amazon Engineers on Amazon

Last week, Tim Bray, a VP/Distinguished Engineer at Amazon, quit and wrote a viral blog post explaining his decision:

Read more...

Dallas Re-Opening Stats (courtesy of Mark Cuban)

After Dallas reopened last weekend, Mark Cuban paid a team of secret shoppers to find out how many restaurants and stores actually re-opened and how many of them followed safety protocols.

Read more...

April 2020 PNW Venture Deals

Here are the PNW startups that announced new fundraising rounds in the month of April. Despite the COVID slowdown, these 28 companies raised $220M+ last month!

Read more...

Earnings Highlights from Microsoft and Amazon

Microsoft: “As COVID-19 impacts every aspect of our work and life, we’ve seen two years’ worth of digital transformation in two months“

Read more...

Actual P&L from a Seattle Restaurant

The owner of Some Random Bar posted a very sobering video breaking down his restaurant’s economics during the quarantine and its prospects going forward. Some key stats:

Read more...

How Will Tech Change Post-COVID?

Coming out of the last crisis, tech companies have done incredibly well, and COVID is driving every organization (and consumer) to adopt new technologies faster than they would have otherwise. So who is best positioned to win?

Read more...

Expedia Raises $3.2B and Gets a New CEO

In Expedia’s announcement about their $3.2B in new funding and new CEO, Barry Diller said, “We are unable to make any predictions as to when travel will rebound but we emphatically believe that it will.”

Read more...

SaaS Trends during the Crisis

Last week at the SaaStr conference, ProfitWell shared data on how 10K+ SaaS companies are being impacted by COVID-19. Some of the takeaways:

Read more...

How to Close a $10B Deal

A couple weeks ago, the Department of Defense released a 317 page report on the $10B JEDI contract. While the report was meant to investigate misconduct, it’s also a great look at how the digital transformation and procurement pro

Read more...

How Seattle Businesses Came Together to Fight COVID-19

Fortune wrote a fantastic article last week on how Seattle came together so quickly to respond to COVID-19 in Washington...

Read more...

Billionaires Hate Bailing Out Billionaires

A bunch of tech investors and CEOs are criticizing the COVID bailouts because the funds are going to help shareholders (i.e., the 1% who own 50%+ of all equity) at the expense of employees and taxpayers (who will foot the bill).

Read more...

CalPERS Called Out

What a great board room story...

Read more...

Stop Buying Stuff on Amazon! -Amazon 😘

Amazon stock hit all-time highs last week, and they are selling so much stuff that they are literally redesigning their site to try to sell fewer items.

Read more...

Going Back to Work with Starbucks and Microsoft

Starbucks and Microsoft both have large businesses in China, so last week they shared some of their learnings about reopening in China with the Seattle business community...

Read more...

What's Happening in VR?

Videoconferencing software is blowing up while people are stuck at home (Zoom grew from 10M to 200M DAUs in three months, and Teams grew from 32M to 44M DAUs in a week), and it looks like people are going into VR to escape quarant

Read more...

First Round's Guide to Navigating the Crisis

If you haven’t already read a dozen “how to navigate the crisis” articles, this one is really good. First Round pulled together all of the advice they’ve been sharing with entrepreneurs along with links to resources.

Read more...

March 2020 PNW Venture Deals

Here are the PNW startups that announced new fundraising rounds in the month of March. These 20 companies raised $200M+ last month!

Read more...

COVID-19's Impact on Seed Investing

In 2020, seed rounds have plummeted to levels we haven’t seen since 2013. For the last three years, there have been 2,000 to 2,500 seed deals by the end of March, but this year there have only been 1,200...

Read more...

How COVID-19 Will Impact Startup Valuations

Last week, I shared some opinions on what’s going to happen to the startup market over the next few quarters. But this week, I thought I’d get some data instead of just speculating (breaking all sorts of VC rules 🙃).

Read more...

What It's Like To Run Slack Right Now

Cool thread from Stewart Butterfield (CEO of Slack) on what it’s like to run a public company and make decisions on what to share on an earnings call during a crisis. Long-ish read, so here are some of the highlights:

Read more...

Trade of the Week 💥

Last week, Bill Ackman, a billionaire hedge fund manager, did an interview where he teared up and warned investors that “hell is coming” if the government doesn’t shut down the country.

Read more...

PNW fighting COVID-19 together

One bright spot in the COVID-19 pandemic is everyone coming together to fight a common enemy (maybe, for the first time ever?). Many of the most iconic companies and institutions in the PNW have been announcing initiatives to help

Read more...

What's going to happen to startup fundraising

The stock market is down over 30% since its peak earlier this year, and investors are selling everything. So what’s going to happen to the startup market? Here are my thoughts:

Read more...

The three most important COVID-19 charts

The three most important charts for understanding the current state of coronavirus:

Read more...

The empty stores of the future

Last week, Amazon announced they are going to start selling Amazon Go’s “Just Walk Out” technology to third parties, and the first retailer to roll it out will be...

Read more...

How are software investors weighing the impact of coronavirus?

Over the last few weeks, the S&P 500 dropped over 10%, with the largest one-day declines in nearly a decade. You’ve probably seen lots of articles about individual stocks that have been heavily impacted by coronavirus...

Read more...

🔥 take of the week

One thing I love (hate?) about tech Twitter is everyone LOVES the idea of being “contrarian,” but when someone actually brings up a contrarian idea, people FLIP OUT...

Read more...

February 2020 PNW Venture Deals

Here are the PNW startups that announced new fundraising rounds in the month of February. These 29 companies raised ~$325M last month!

Read more...

How to raise money, according to the pros

Last week, YC published their guide to raising a Series A - great, practical advice combined with data from their companies. Some of the highlights:

Read more...

🤑 <-- Seattle tech workers

There were a bunch of headlines last week on how the 125K “information workers” in King County make an average of $279K per year according to BLS data. That's $35B a year...

Read more...

Consumer brands and marketplaces that VCs love

A few weeks ago, I wrote an article on why VCs love SaaS businesses, and some readers thought the takeaway was marketplace and consumer businesses are bad. Not what I meant! The takeaway was that SaaS startups should be...

Read more...

Find your perfect job

Ever wonder… if I weren’t a _______, what would I want to do? Well here’s some research showing which jobs are most closely related to one another based on the personality profiles of people in those professions...

Read more...

Coolest spreadsheet ever

Excel is the MVP of the Office suite, and here is proof - you can implement computer vision algorithms in Excel without any special scripts or macros...

Read more...

Earnings season for Seattle companies

Redfin and Expedia both had great earnings calls last week with Redfin stock up 20% and Expedia up 10%. These are definitely two companies to track over the next few quarters...

Read more...

Amazon is the biggest advertiser on earth

Amazon spent $11B on ads last year. That’s literally enough money to buy an Echo for every single person in America and have $1.5B left over to go acquire Sonos. According to WPP, this represents ~2% of all global ad spend...

Read more...

January 2020 PNW Venture Deals

Here are the PNW startups that announced new fundraising rounds in the month of November. These 23 companies raised ~$180M last month!

Read more...

What's new at Madrona

This year is Madrona’s 25th birthday 🎂, and we are starting the year off with a lot of exciting news! Here’s a quick overview of what’s going on at Madrona and our portfolio companies:

Read more...

Amazon reaches $1T market cap!

Amazon has officially joined Apple ($1.4T), Microsoft ($1.4T), and Alphabet ($1.0T) in the cuatro commas club! To celebrate, here are a few great quotes from haters including Barron’s 1999 Amazon.bomb article:

Read more...

Spokane's Top Startups

Here’s a report highlighting 30 of the most exciting startups in eastern Washington...

Read more...

Okta's startup picks

Every year Okta publishes a report on the fastest growing apps used by their customers, and it’s a great crystal ball for startups...

Read more...

PSL Studio Deep Dive

Part Two on PNW / Seattle venture firms and what they are investing in. Here we’ll take a closer look at PSL...

Read more...

What seed-stage companies is Madrona investing in?

Last week, The Information wrote an article on the top seed investors over the past decade, and Madrona was one of the ten firms on the list... So what does the next generation of Madrona’s startups look like?

Read more...

ARK Big Ideas 2020

I really like ARK’s research reports because they do a good job analyzing markets from first principles (even though I sometimes disagree with their conclusions). Here’s a link to their 2020 report...

Read more...

🚀 Rocketship stocks

Space travel is super hot. Over the last two months, Virgin Galactic’s stock has jumped from $7 to nearly $20...

Read more...

Seattle's top 18 enterprise startups

Here is the latest list of top enterprise startups to watch in Seattle:

Read more...