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

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Dan's Top 10 Jeff Bezos Quotes

You’ve all read enough articles about Jeff Bezos stepping down as the CEO of Amazon last week, so I won’t belabor the topic. Instead, here is this week’s grand opus. My top 10 Jeff Bezos quotes… in meme format.

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What Dan's Talking About

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

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Elastic: NOT OK. AWS: Fishy.

Open source software (OSS) started as a reaction to companies like Microsoft and Oracle making “unfair” profits

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New PNW Reality Show

If you’ve finished Bridgerton and need a new show, check out Rival Peak. It’s a Survivor + Big Brother-style reality show set in the Pacific Northwest

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Readers' responses on Parler

Last week, I wrote a summary of the events leading to Parler's shutdown, and received a lot of thoughtful responses about what happened, so here are some thoughts from DL readers on the Parler shutdown.

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Amazon Shuts Down Parler

This is probably the most important tech news of last week, but it’s been pretty difficult to follow, so here’s my summary of the key events leading up to Parler’s shutdown:

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Haven Shuts Down

Three years ago, Amazon, Berkshire Hathaway, and JPMorgan Chase teamed up to launch Haven, a joint venture to lower healthcare costs through technology solutions. Here’s what happened:

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How to Compete and Win

Here is a fantastic thread on how DoorDash came from behind to beat Seamless and UberEats in food delivery:

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The DL's 20 Slides on 2020

If you want to get caught up on what happened in the PNW startup and tech markets last year, here’s my 20 slide summary of what happened in 2020. Some of the highlights:

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Dalí + WALL·E = DALL·E

OpenAI released another incredible demo last week with DALL·E, a version of GPT-3 that is trained to generate images from text descriptions.

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December 2020 PNW Venture Deals

Here are the PNW startups that announced new fundraising rounds in the month of December. These 22 companies raised more than $400M last month!

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Announcing... DL Dossiers (New in 2021!)

If you’re a DL subscriber, you probably follow the PNW startup and venture landscape pretty closely and you might’ve wondered to yourself, “What are the best startups in Seattle that I should be paying attention to?”

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November 2020 PNW Venture Deals

Here are the PNW startups that announced new fundraising rounds in the month of November. These 24 companies raised more than $275M last month!

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New PNW Unicorns 🦄

In addition to Cradlepoint getting acquired for $1B+ last week, Geekwire wrote a great article on Tanium, a $9B+ cybersecurity company that is moving its headquarters from the Bay Area to Seattle.

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Simple Software Sales Math

David Sacks shared a great thread on the simple math behind setting up an enterprise software sales team last week. Here are the key takeaways:

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October 2020 PNW Venture Deals

Here are the PNW startups that announced new fundraising rounds in the month of October. These 27 companies raised more than $400M last month!

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Kelsey Hightower 💥

What a fantastic profile of Kelsey Hightower in Protocol last week. Hightower is a Principal Engineer at Google Cloud, and he was one of the key contributors to Kubernetes. He literally wrote the book on Kubernetes...

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The 100x Club

The Information wrote a great article last week on “The 100x Club,” which is the group of SaaS startups raising money at 100x revenue multiples.

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Satya's 2020 Bonus

We’re in Q4, which means a lot of people are getting year end bonuses, including the execs at Microsoft! Last week, Microsoft released their FY20 compensation report...

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How Microsoft Plays Games

Why Microsoft is winning in gaming, while Amazon and Google are still trying to figure out why gamers aren’t excited about Luna and Stadia.

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The (Not Failing) Media Company

There were a lot of hot takes on Quibi last week, but this ~170 slide deck on “The (Not Failing) New York Times” is much more interesting.

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How to Ask Questions Like a VC

A few weeks ago, one of the local accelerators asked me if I had a list of questions to help startups prep for investor meetings. I didn’t have one ready, but I thought it would be a great idea to write one, so here’s my list...

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Best Prime Day Ever (...for small businesses, at least)

One of the most fun parts of working with startups is celebrating the “best day ever,” “best month ever,” and “best quarter ever” every time there is a big milestone. Of course, for fast-growing companies, every quarter is typical

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V1 Guide to Marketplaces

Version One, a Vancouver-based VC, published the third edition of their Guide to Marketplaces, last week, and it’s a fantastic resource for anyone interested in building and investing in marketplace businesses.

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What $500M Buys You in Seattle

Here are some financial metrics for three Seattle area companies. They look very different, but all are valued around $500M. Can you guess what each of them are?

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Should Companies Take Political Stands?

One interesting story from the last couple of weeks was Coinbase CEO Brian Armstrong’s blog post stating that Coinbase is a “mission focused company” that will not engage in political causes and broader societal issues because the

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What's Next for Software Multiples?

Morgan Stanley published an interesting report last week on valuation multiples for software companies and why they are at decade highs. Their take was that software stocks are up 50%+ YTD, but for good reasons:

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September 2020 PNW Venture Deals

Here are the PNW startups that announced new fundraising rounds in the month of August. These 40 companies raised more than $450M last month!

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Trust Me 🙂

According to the study Jeff Bezos cited, people trust Amazon more than the police, extreme weather warnings, and the US government. So would you trust them with your palm print?

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How to Remote Work

Fast Company wrote an excellent article about the asynchronous, all-remote work style at Gitlab and their (amazing) 7,100 page employee handbook that makes remote work work.

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Microsoft, Microsoft, Microsoft

Microsoft made a bunch of big announcements for both new products and existing products last week. Here’s a recap:

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The Mike Speiser Playbook

Kevin Kwok published a fascinating blog post last week on Mike Speiser, the VC at Sutter Hill Ventures who started Snowflake. If you haven’t heard his name before, you should definitely read this article.

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Obsessed with Obsidian

Roam Research, which raised $9M at a $200M valuation, with $1M of ARR was one of the hottest VC deals this year. According to The Information, they were rejected by YC five times, but now they have 100K+ users, including people li

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❄️ “A stock is worth exactly what somebody wants to pay for it”

Would have been hard to miss this one… but Snowflake’s IPO last week was the largest software IPO ever. The IPO priced at $120, and the stock closed on the first day of trading at $250+, for a market cap of ~$70B!

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💧 Wait, what?

OK - so everyone is super pumped about Snowflake and the future of data in the cloud. But have you heard about this bottled water IPO? Nongfu Spring IPO-ed a couple weeks ago at a $50B market cap. And…

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Opendoor Investment Memo

Last week, I shared Bessemer’s investment memo for Shopify with notes on interesting parts of the memo. People seemed to like that, so here’s another VC investment memo!

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Do you work at Amazon yet?

Despite a global pandemic, hiring at most tech companies (except for Uber, Lyft, and Workday) is still on track or even accelerating.

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Bessemer Investment Memos

VCs normally don’t share their investment memos, and the only “public” memo out there is Sequoia’s investment memo for YouTube’s seed round that was used as testimony in a lawsuit.

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Remote Work Sucks -Reed Hastings

As everyone continues to rave about remote work, it was fun to read this interview with Reed Hastings on why he thinks remote work is “a pure negative.” Some highlights:

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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:

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Seattle Unicorns

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

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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:

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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!

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Request for Help!

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

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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.

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“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. 😲

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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:

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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!

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Best New Amazon Product

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

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🏇 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.

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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...

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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...

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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:

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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..

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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!

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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.

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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.

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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

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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:

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+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:

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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.

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Shoutout to the GeekWire Award Winners!

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

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Investors love SPACs

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

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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...

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+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...

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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.

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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.

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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

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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!

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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. 😆

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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.

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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)

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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.

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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.

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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.

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👊 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

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+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

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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

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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

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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.

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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.

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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!

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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?

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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...

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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

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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.

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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.

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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.

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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...

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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:

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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.”

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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:

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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...

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Amazon Engineers on Amazon

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

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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.

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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!

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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“

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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:

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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?

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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.”

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