How deep can a friendship go?

David Perell of North Star Media writes this week about The Fruits of Friendship. He quotes the late Irish Poet John O’Donahue:

When was the last time you had a great conversation? A conversation that wasn’t just two intersecting monologues, but when you overheard yourself saying things you never knew you knew, that you heard yourself receiving from somebody words that found places within you that you thought you had lost, and the sense of an ‘eventive’ conversation that brought the two of you into a different plane and then forthly, a conversation that continued to sing afterwards for weeks in your mind? Conversations like that are food and drink for the soul.

In this love, you are understood as you are without mask or pretension. The superficial and functional lies and half-truths of social acquaintance fall away… When you really feel understood, you feel free to release yourself into the trust and shelter of the other person’s soul… Love is the only light that can truly read the secret signature of the other person’s individuality and soul.

The O’Donahue passages are especially meaningful for me as I remember back to celebrating my 40th birthday a year ago. About two dozen of my friends joined me to celebrate, and it was gratifying to see how quickly so many friendships where we’d been out of touch for years picked right back up where they left off. Those conversations where you dive deep into life are so fulfilling.

From the Operators

Patrick Campbell of Price Intelligently shares the Lessons Learned from 3000 SaaS Companies. The amount of real customer discovery and learning going on in the industry is troublingly shallow.

Nathan Barry of ConvertKit debunks the myths that keep startup founders from pursuing revenue through traditional sales in Direct Sales for Bootstrapped SaaS Startups: from $1,300 to $725,000 MRR

From the Investors

Morgan Housel of Collaborative Fund is on a roll with his blog and writes this week about Degrees of Confidence. It’s a useful rubric enumerating the different degrees of confidence you could have on any given issue, and a great way to calibrate how much thought you’ve put into something.

Dave Kellogg of Host Analytics breaks down Highlights from the 1Q19 Fenwick & West Venture Capital Survey. Subsequent rounds are averaging 75% valuation increase from the previous round, which is lower than I would have expected. 9% of deals had a liquidation preference multiple, which is useful to know if you’re negotiating a round.

Matt Turck of FirstMark is curious about Bootstrapping as an avenue for founders, despite being a VC. Rather than trying to mete out pros and cons, he asks some good questions and puts together a list of several bootstrapped companies I didn’t know about.

Where are the weirdos hanging out?

Way back in 1993 as a teenager, I would go to the bookstore any chance I got to see what new book I could buy that would help me learn to program. I can still faintly remember seeing this weird magazine on the rack that delved into nerd culture.

Wired is ironically fairly tired today, but back in 1993 it felt like you were tapping into something completely novel. This turned out to be issue 3, back when they could only afford to publish every other month.

The thing that enraptured me was reading about MUDs. I was familiar with Bulletin Board Systems, but had never heard of the Internet. After reading about MUDs where you could be in a text based virtual world at the same time 40 other people were, I had to find out how to get online. Later that fall when my brother started college and got access, this was the first thing I tried to do. I remember spending countless hours MUD’ing the next year.

What didn’t catch my eye in that issue of Wired is their first write up of this new thing called the World Wide Web.

The write up doesn’t predict anything that grand, and says, “Today, W3 provides an eclectic collection of information including a database of poetry, documents from Project Gutenberg, computer algorithms from MIT, weather information, library catalogs, and a biochemical database.” Instead the ambitious predictions from that issues cover story were 500 channels we’d get from our cable provider.

I maybe should have paid more attention to the web than MUDs that year, but I caught on soon enough. What really strikes me reminiscing is how weird it was to be hooked on the Internet at that point. I don’t think I’ve come across anything in life that has ever felt such much energy and potential.

I’ve been asking friends lately, “Where do you notice weirdos right now?” It’s my way of trying to find the next thing with as much potential. Scenes that have captured so much attention that it rallies a clique around it. Answers so far range from nootropics to 30 year olds figuring out how to get frugal, and retire early. Maybe they’re tapping into early human computer brain interaction, or what it might be like to live in a post scarcity world.

Have you found a pocket of experience that seems weird, but might be big someday? What aspect of your life do you feel like you’re living in the future with?

What to do with competitors?

This week we’re trying something new: featuring a single post from a founder and VC. Each ultimately end up touching on how to handle competitors while drawing different conclusions. After reading both, you’ll probably arrive at your own more nuance answer.

Hiten Shah of FYI starts out with the bromide we often hear and too often forget, ‘Go talk to your customers lest you build something they don’t need.’ After fixing that, KISSMetrics exploded in growth, but ultimately ended up slowly losing. Shah tells the story of what went wrong after achieving product market fit in My Billion Dollar Mistake.

Sammy Abdullah of Blossom Street Ventures writes Stop worrying about your competitors, but goes on to elucidate some novel reasons why this is so misdirected. His piece is an excellent companion to Hiten’s post.

What if you had to pivot after your Series C?

This weeks posts include a stomach wrenching experience from CircleUp founder Ryan Caldbeck who writes, “I remember sweating a lot. I remember feeling a pit. I remember for the first few months after the start of the downturn always- *always* – feeling terrified. Imagine feeling like that for an entire day. I felt that way for months.”

But first we owe our readers an apology.

Last week, we featured a section on great interviewers with Charlie Rose as an example. Several of our readers were quick to point out that in November 2017 Charlie Rose was accused of harassing female co-workers throughout his career. We were completely unaware of this when we cited him, and apologize for picking such a terrible example. Rose has since apologized, acknowledging some of the claims and denying others, and upon review of the facts we believe his behavior is reprehensible. We are so disappointed to be let down by our former hero, and have completely removed him from last week’s post, and noted the change there.

Tyler Cowen, who we featured next to him, is a great interviewer. I feel bad to have put him next to the discredited Rose.

Our readers were also quick to point out there are several awesome female interviewers worth exploring: Mary Lousie Kelly, Soledan O’Brien, and Terry Gross.

From the Operators

Ryan Caldbeck of CircleUp expresses the dramatic ups and downs of pivoting his company in this tweetstorm.

Avni Patel Thompson of Poppy grapples with the question of how to start a startup without funding in Finding the space to take the risk and build as a parent with bills..

Jasper Diamond Nathaniel of formerly of Revere tells a cautionary tail for co-founders making compromises to mix their ideas together. 18 months later, he was left running the company without them, and figuring out what to do in When Your Startup Fails.

Danielle Morrill of GitLab (also co-editor of BuriedReads) continues to process the loss of her former startup, and the physical space it inhabited, as if it were a relationship in 564 Pacific Ave..

The Mattermark team inside 564 Pacific. (Thank you René, Samiur, Beau, Sarah, Josh, Evion, and Bryan)

From the Investors

Naval Ravikant of AngelList is on a roll this week with his podcast Labor and Capital Are Older Forms of Leverage. A huge reason I’ve always been interested in software as a career is because it has zero marginal cost to reproduce, and so it huge impact in the economy. Naval lays out how capital has similar power, but labor is counter intuitively one you have to be careful with.

Albert Wenger of Union Square Ventures writes this week about the “asymmetry of limited upside, unlimited downside” in Learning from Notre Dame.

Seth Levine of Foundry Group along with Brad Feld encouraged us to get audited fairly early on at Mattermark. Having 3 years of audited financials helps immesurably with M&A and other options you want to keep open. This week he covers How much should you be paying your auditor?.

Om Malik of True Ventures is getting skeptical of Amazon’s dominance in e-commerece. I’m skeptical from a different angle. Everyone in Silicon Valley seems to beelieve Amazon has taken the cloud computing market and will never be unseated. If you’ve used their console as a developer, you know they are confusing, have poor documentation, and can be difficult to use. Someone is going to eat their lunch, and if you think it could be your startup, we’d love to talk as potential angel investors.

Intense Curosity

Editor’s Note: This post formerly featured Charlie Rose, please read this post to learn more on why that content has been removed.

Last night while running errands, I turned on Tyler Cowen’s podcast Conversations. This week he interviewed researcher Ed Boyden. It was the first time I’d ever heard of the field optogenetics. Boyden and several researchers have been working on how we can create a virus that puts tiny photoreceptors on specific cells in our body. The cells become a sort of solar panel that can then be activated by tiny fiber optic lights. The research is important, because so much of pharmacology right now is caught up with imprecise instruments that bathe the whole brain in chemicals, rather than precisely targeting the neurons that control certain functions.

I loved the clarity that Boyden explained the field with, and it turned out to be the tip of the iceberg. Cowen’s interview ended up going much further into all kinds of topics. I started counting the times I heard “I wonder…” or when Cowen would ask something controversial and instead of getting into the fray directly Boyden would step back and start “one way of thinking about this is…” If I could just find all the podcasts each week that use these phrases or have this tenor of dialog–I’d be in a sort of personal heaven. These interviews are an oasis amongst a desert of 30 second interviews and talking points. The world needs more Tyler Cowens.

From the Operators

We didn’t find any amazing founder posts this week. Keep sending us great operators posts that you read to

From the Investors

Christoph Janz of Point Nine Capital was on a roll this week. First he recounted his great post from five years ago, “Five ways to build a $100 million SaaS business,” and gave a nice update on several things that he’s learned since. It’s still incredibly clarifying for someone starting a new company that wants to make it to IPO. Christoph also touched on a topic we wrote about a few weeks back: the rise of institutional angel and the decline of self-funded angel investing. He explains the pros/cons of the two approaches in 8 reasons why you shouldn’t raise a VC fund (and 4 why I love being a VC regardless).

Morgan Housel of Collaborative Fund starts off with the story of researchers Richard Held and Alan Hein who found that being an inactive viewer is actually worse than being blind but able to get into the bump and grind of life. The research alone is throught provoking enough to justify reading, but he folds in the history of the 1960s, the 2000 recession, and venture investing. Read Morgan’s incredible post You Have To Live It To Believe It.

Who Made a Bet on You?

This week Brad Feld’s dad wrote a thoughtful post on how he started to see the spark of talent in his son and decided to buy their first family computer so Brad’s talents could keep growing. It got me thinking about all the people who made bets on me. Like many people, my mom immediately comes to mind. But I also think about a great teacher, Jim, who taught me about taking all my programming skills into business. Or my internship mentor Bill who taught me most of what I know about hiring.

Who are the people that believed in you and made early bets? If you feel like sharing, write to us with your story. I’d love to share some of these next week.

From the Operators

Steph Smith of Toptal does the most in depth pieces on remote work I’ve seen. She took ideas from several great business books. For example, extending Give and Take by Adam Grant she emphasizes why celebrating givers in remote environments is doubly important, given their lack of visibility.

Investor twitter was in their regular tizzy about inflated valuations for YC companies this week. Jason Crawford of Flexport had a great thread on Twitter going beyond the platitudes and exploring founder psychology and dangerously inflated sense of progress.

Though unrelated to startups, I loved the David Perell’s interview with Nick Kokonas of Alinea restaurants. The conversation is wide ranging, covering everything from pricing dynamics in restaurants and to how Kokonas started buying up medical equipment on eBay in the early 2000s for gastro-tech cooking.

From the Investors

Brad Feld of Foundry Group made me smile this week with this adorable video of A Robot, A Puppy, and An Arduino. As if that wasn’t enough, he posted a touching story written by his dad Birth of An Entrepreneur. It brought back good memories of my mom spending $2,000 from our very thin family budget on our first family computer in 1988. I ended up learning BASIC on it, and it changed my life.

Brian Laung Aoaeh of REFASHIOND Ventures put together one of the most comprehensive docs on seed fund construction I’ve seen. While not shocking, this is a great one to bookmark and send to anyone that’s thinking of making the leap from angel investing to raising a seed fund from LPs.

Jessica Livingston of Y Combinator discusses Why I Started the Summer Hackers Program. This is a topic heating up for me since we’re trying to accelerate diversity hiring at Quizlet. The next big challenge I see is that we have all kinds of awesome people coming out of coding academies, but the real trick is landing that first job where you get trained in industry practices. There’s a huge opportunity for someone to build a community and help people with that second step.

French fries can be sacrosant

This week I came across John Greathouse of Rincon Venture Partners and his post Startup Lessons from watching “The Founder”. The movie portrays the story of Ray Kroc buying McDonalds from its founders and scaling the business up. The post has several good take aways, but nothing does the story justice like Ray Kroc’s own autobiography Grinding It Out. His introduction is a preview of just how page turning the story is:

The next morning I got up with a plan of action in mind. I was on the scene when McDonald’s windows opened for business. What followed was pretty much a repeat of the scenario that had played the previous day, but I watched it with undiminished fascination. I observed some things a lot more closely, though, and with more awareness, thanks to my conversation with the McDonald brothers. I noted how the griddleman handled his job; how he slapped the patties of meat down when he turned them, and how he kept the sizzling griddle surface scraped. But I paid particular attention to the french-fry operation. The brothers had indicated this was one of the key elements in their sales success, and they’d described the process. But I had to see for myself how it worked. There had to be a secret something to make french fries that good.

Now, to most people, a french-fried potato is a pretty uninspiring object. It’s fodder, something to kill time chewing between bites of hamburger and swallows of milk shake. That’s your ordinary french fry. The McDonald’s french fry was in an entirely different league. They lavished attention on it. I didn’t know it then, but one day I would, too.

From the Operators

Mark Roberge formerly of Hubspot gave a talk titled A Step by Step Guide to Revenue Growth. The natural dynamics of raising venture capital will steer you to start growing your customer base as quickly as possible. Months and years down the line this can leave a wake of churned customers and fired sales reps. His advice of starting with a single “aha” moment you know leads to an engaged user, and then measuring that by cohort is sound advice. At Quizlet, our premium content effort that I work on is facing this very dilemma. Mark’s talk is making me think twice about whether we’re ready to pour gas on this, or if we should measure student success a bit more carefully before scaling.

Writing this newsletter has made me a better thinker. There’s something about having to put your thoughts on paper that forces you to really flesh out an idea. You don’t have to start a newsletter to do this. This week our friends Andy Sparks of Holloway writes about his practice of journaling.

From the Investors

Tomasz Tunguz of Redpoint Ventures took a look at the data this week and asked Where Have All the Angels Gone? Angel deal volume peaked around at ~700 deals a year in 2014, and has fallen to below 250 a year. Institutional seed has largely taken the share. For Danielle and I, we’re happy to stay away from raising a seed fund. It leaves us free to take riskier bets, and not be accountable to LPs. We can do fewer deals and spend more time with the founders we invest in.

One of the things that originally got me fascinated about finance was reading Daniel Fischel’s book Payback: The Conspiracy to Destroy Michael Milken. During my childhood I remember hearing about the savings and loan crisis and how it was portrayed as a blight on capitalism and financial innovation. Fischel sets the records straight and explains how Milken actually saw a fundamental gap in how we evaluated credit. So it was fascinating this week to read Should Private Startups Be Issuing More Bonds and see many companies issuing debt who are risky but definitely not going to $0 are still being rated as effectively junk status.

Mark Suster of Upfront Ventures writes this week that managing a board is a bit like flying: most of the time everything is fine, but when you hist turbulence, you don’t want to be building a relationship with your board under duress. He offers advice on how to host dinner with your board so you can build the relationship before it will be truly tested.

Walt Disney and Plus’ing

When Walt Disney was working on Snow White, the first full length animated movie, he asked his staff to keep thinking of ways they could make it even better. If someone brought him a drawing or design, he would ask them “how can we plus it.”

I was reminded of this while out to dinner tonight. Danielle and I have a favorite local spot where we like to sit at the bar. Our first time there, I was having a negroni in a martini glass. It had been sitting half finished while we talked. Any cocktail served cold that gets to room temperature never tastes as good, so I had kind of given up on it. Without me saying a word, the bartender took out a chilled martini glass from below the bar, and transferred my drink into the cold glass. It’s the simplest thing, but ever since we’ve been coming back regularly. I’ve noticed the bartenders have all been trained to routinely do this, something I’ve never seen anywhere else.

Businesses that take an already great experience and add a finishing touch are inspiring. Next week at work, I’m extra motivated to find ways we can do this in our product.

From the Operators

Two weeks ago we asked for help finding more operator blogs. You all were amazing and sent us several to read. We’ve added even more founders to our swelling RSS list. The operators posts were so good this week, we’ve decided to run with just them. VCs it’s time to up your blogging game 😉

Tracy Lawrence of Chewse writes “I’m starting to believe that truth is the highest leadership virtue.” She lays out common barriers and how she’s overcome them in Losing (and Finding) My Voice as a Leader.

We featured Kevin Hale of Y Combinator last week, and he’s on fire again this week, as he sat down to interview Mike Knoop of Zapier about Product and Design Processes for Remote Teams. Kevin has a great insight about his original company Wufoo and Zapier both fitting into a lifecycle all business face: how do I get online; how do I start getting data; how do I process that data once I get it. Each bucket is probably a multi-billion dollar category, and none of them are fully mature IMHO.

Marie Prokopets of fyi captures The 7 Step Onboarding Process to Get Employees Fully Ramped In 2 Weeks. Something I’d add that’s worked for us: make sure engineers get to commit code on the very first day. This sets the tempo for “hey we’re a startup and we make progress on the scale of days, not quarters or years.” The habit also forces you to keep your developer setup streamlined enough that it’s possible.

Matic Jurglič of Nightwatch ponders If Marcus Aurelius were a software developer. His post struck a chord for me, especially having transitioned from pre-product market fit startup to scaling. Our best developers didn’t complain about hacky code, but rather said to themselves “I’m sure the person who built this had a lot of constraints I don’t know about, let me just see if I can pitch in and make it better.” Hiring devs that do the opposite–complaining and griping about technical debt without action–is a kiss of death for scaling startups.

Richard Ian Porter of IBM answers What PMs Can Learn From Military Veterans. He confront the assumption that hiring veterans leaves you with people expecting structure and strict leadership. Of course startups don’t usually have to adapt and react when a bomb goes off in their office, which Porter’s colleagues did deal with.

We bumped into Fletcher Richman of BubbleIQ on a Twitter thread this past week and heard he had put together a Colorado Early Stage Funding guide. If you’re raising an early round Fletcher’s list is a great place to start.

Danielle started a new job

After 9 months of sabbatical, Danielle started a new role at GitLab this week as GM of Meltano. It will come as a surprise to exactly no one who knows her that she’s found a way to combine her love for data and experience with technical tools to build an open source product to unify data workflow tooling into a single seamless pipeline. For an idea of the kind of engineering work companies currently must do to solve this problem, check out “Managing Uber’s Data Workflows at Scale” on the Uber Engineering blog.

The company is fully remote, and Danielle is hiring for a UI/UX designer with experience building data-rich software interfaces. Her new email is

From the Operators

If you’re formalizing HR in your company, Jenny Terry of Buffer shares how they’re Continuing to Improve on Pay: Our Latest Changes to the Salary Formula and How Much it Costs. For juicy details on the actual salary numbers, consult Buffer’s Salary Calculator.

Justin Kan of Atrium has noticed his happiness improved beyond what he thought was possible. He’s realized life isn’t just a hedonic treadmill where happiness always has to reset back to zero each time. The lessons he learned to get there are in Feeling Good: Justin’s Program.

Kelly Knickerbocker of Pitchbook put out a great list of 27 black founders and investors to watch in 2019. I hope each of them is prepared for lots of inbound from investors and LPs! We’re especially thrilled to see XFactor portfolio founder Monique Woodard of Court Buddy on the list.

From the Investors

Kevin Hale of Y Combinator sketches out How Investors Think About Ideas. An absolute must read for startup newbies and veterans alike, this video (6:17) provides a clear way to grasp how investors gauge viability, market size, and whether its possible for a startup to eventually be worth $1B.

Nathan Benaich of Point Nine Capital goes deep on 6 impactful applications of AI to the life sciences. For example, I didn’t know some of the same work behind AlphaGo is being applied to protetin folding. If you’re like me 6 months ago and wondering why does this even matter, check out this primer.

Harry Stebbings of Stride.VC tweeted that Founder NPS is the most important metric for VCs. He points out the importance of valuing the founder’s time, and I think sooner or later smart VCs realize that showing up to meetings on time is a huge differentiator, since their customer knows that every unproductive hour that goes by they’re running out of oxygen.

And Now For Something a Little Different

Haruki Murakami describes the wonderful feeling of utter conviction, as read by Matt Malloy, in On Seeing The 100% Perfect Girl One April Morning

Your life on a chalkboard

Our investor Jeff Bussgang asked several years ago if we’d be willing to do a case study on Mattermark for his entrepreneurship class at Harvard Business School. At the time, Mattermark was flying high and growing 100%+ year over year. The case was a snapshot in the time, asking students crucial questions about what direction the company should take: should it dig deeper into the VC customer base, or expand into the sales and marketing use case?

For the first time in the four years it has been taught, all three of us flew out together to Boston this week and fielded questions from students. It was the first time I had seen the case taught, and it was fascinating to watch students dive into something I had worked so thoroughly on. Watching five years of your life batted around a classroom and recorded on a chalkboard by a professor is a humbling experience.

At first, watching the case study method was jarring. How can you possibly compress so much complexity into a moment and a single binary decision! But talking to students after, they seem to have a firm grasp on the expanse of what they were evaluating, many of the ways you could look at it, and even the notion that you never get all the data at one moment to make a decision.

I left feeling like despite the bad rap that business schools get, the students I saw seem would have above average odds of success as startup founders. It was also great to spend time with our cofounder Andy, and be reminded how much creativity there is with all three of us in the room. Hopefully life is long enough that we all get to work together again.

From the Operators

We did not find a good operator post this week. Despite us following 1,000+ RSS feeds, the sad fact is founders don’t write often. If you know great founders that are writing, please send links our way.

From the Investors

It’s popular to say making work a big part of your life is neglectful and shortsighted. While lots of other things in life deserve attention, I believe it is in fact incredibly important to have a rewarding career. I thought Hunter Walk of Homebrew did a good job of capturing that in Would You Put Your Job On Your Tombstone?

A founder recently came to Joanne Wilson of Gotham Gal Ventures seeking advice on what to tell her board about her pregnancy. Instead of unveiling some complicated plan for her maternity leave, Wilson counseled, “just simply tell them you’re pregnant, this is your due date, how excited you are, and that’s it”. Guess what–that works fine! Wilson’s full post is worth a read: Diversity Should be #1 for Good Reason.

From the Analysts

Before Softbank was swashbuckling into deals with Door Dash, Uber, and Opendoor, there was Tiger Global. We hardly hear anything about Tiger these days, but just below the radar they continue to aggressively back some of the most promising startups. Savannah Dowling of Crunchbase pulls back the Wizard of Oz curtain in Prolific Tiger Global Management Maintains Strong Investment Posture.

Danielle and Kevin started jobs

This week both Danielle and I started new jobs. I’ll be managing an engineering team for Quizlet’s new office in Denver. I hadn’t heard of them until being recruited, and was blown away to hear they’d passed 50 million MAU and are used in a huge percentage of schools. We’ll try to share more details on Danielle’s new job next week, which is with a different company.

Taking a 7 month sabbatical has been eye opening. Sometime, I need to write more about it. It’s crazy to think I had worked 20+ years never taking anything longer than a 2 week break. Now that more people are working white collar jobs that don’t wear out their bodies, I hope it will become common to delay retirement, but mix in sabbaticals like this. It really is life changing. One of my favorite parts has been building out Buried Reads. I’ve got it honed to a few hours each week, and will continue to publish weekly notwithstanding the new job.

From the Operators

I caught up with Aline Lerner of last week, and as per usual we got into a great conversation about recruiting. I asked her what single one of her data-driven posts she think would be most interesting to Buried Reeaders. She said What do the best interviewers have in common is a post founders regularly tell her has been helpful. If you haven’t read it already, check it out.

I knew that Buffer and Baremetrics were regularly sharing the revenue and profit actuals, but it turns out there are way more startups doing this. Postmake put together a list in Open Startups.

Daniel Gross of Pioneer put together a list of Markets To Build In that are new on his radar. I learned a ton from the post. For example I didn’t know Travis Kalanick is starting up a new company called CloudKitchens, probably from what he learned building UberEats.

From the Investors

Jerry Neumann of Neu Venture Capital follows up on a previous strategy post this week with Managing Technological Innovation: Industry Analysis. I’ve tried to read Michael Porter’s famous strategy book, and got bored to tears. Jerry’s slides give you a way easier entré into strategy theory.

Ryan Caldbeck of CircleUp tweeted this week about CEO comp. There are some juicy parts in here on secondary sales where founders take money off the table before exit.

In The Seed Slump Fred Wilson of Union Square Ventures summarizes an earlier Mark Suster post, but ends up getting to a more provocative question: is it time for VC to go through change given everything upmarket and down market has changed so dramatically.

Bethany Crystal of USV asks Who anoints you with decision-making power? She links to a fascinating book Lives of Promise: What Becomes of High School Valedictorians. Maybe that’s the sweet thrill of confirmation bias that I’m feeling given that I was a terrible student through most of grade school, and ultimately dropped out of college.