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 danielle@gitlab.com


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 Interviewing.io 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.

When Hard Work Pays Off

This is Kevin here. Last week a short but impactful chapter in my life came full circle when HelloSign was acquired by Dropbox. I joined the company in December 2011, and working with the company’s CEO, Joseph Walla, showed me the power of focus and saying no to distractions. I blogged my reflections in When Hard Work Pays Off.


From the Operators

Patrick Collison of Stripe appeared on EconTalk, my favorite podcast, to discuss Innovation and Scientific Progress. Collison is concerned we‘re spending more than ever on science research, but getting diminishing returns. Much like Peter Thiel‘s The End of the Future, it reminds me that innovation in the largest industries (e.g. transportation, healthcare, and energy) has slowed to nearly zero. While I’m tempted to blame it on politics, I was reminded of the arguments in The DIM Hypothesis by Leonard Peikoff, which goes further down the philosophical stack from politics into epistemology.

Chad Dickerson of Reboot (and former Etsy CEO) shares The Magic of the Personal Check-In: Red, Yellow, Green. Danielle and I have been using this in team meetings ever since attending a Reboot founder bootcamp, and find it helps people bring their whole self to work.

The first time I read Blueprints for a SaaS Sales Organization, after nearly 3 years at Mattermark, I thought to myself, “Why couldn’t I have found this on day 1?” Staying human in an age of automated sales came across my radar this week, and it gave me the same feeling. If you read the Blueprints book, make sure to check out the fantastic charts and visuals.

Sarah A. Downey of Accomplice has resumed her excellent blog series Startup Trek, drawing a startup takeaway from each The Next Generation episode. We re-watched the controversial episode “Angel One” and scratched our heads trying to figure out a good startup allegory, but Sarah did much better than we could comparing Riker’s efforts to assimilate with the all female oligarchy to a story of showing up to a startup interview in a Brooks Brother’s suit, only to find everyone in hoodies.

Andy Sparks of Holloway announced Good Work, a Newsletter by Holloway this week. If you like Buried Reads, Andy has a very similar style, but is covering the challenges of modern work.

Imagine finding product market fit after your whole team has gone without salary for over a year. And just when it seems things are clicking, the government mandates your cost of goods sold must go up by 3x. Tim Westergren of Pandora sits down with GGV Capital in Real Talk Episode #19 to tell his harrowing story.


From the Investors

This week Josh Kopelman of First Round Capital appeared on Harry Stebbing’s Twenty Minute VC. Kopelman learned that partner meetings don’t have to be about getting your deal approved, rather “It’s finding truth, what’s knowable, and what risks are we taking.”

What’s it like inside a VC firm? How things work at Kima Ventures provides an inside look. For another look in VC operations, Eze Vidra of Remagine Ventures compiled the The European VC Tech Stack 2019. If you have other tools you use to source deals, keep track of prospects, find comps, or otherwise rock out your job let us know. We would love to share your “Buried Tools”.

Jason Kwon and Aaron Harris of Y Combinator announced A Standard and Clean Series A Term Sheet. Apparently, we haven’t seen any particularly crazy terms in our startup lives as this seems pretty basic. But if you’re looking to simplify, use this one. Also — why not just draft the term sheet you want and send it to the VC?

Boris Wertz of Version One Ventures rolls out his fund’s newest thesis Building Strong Local Communities. What I really love about Version One is the amazing guides they publish, and Understanding Social Platforms is no exception.

Lisa Suennen of Manatt, Phelps & Phillips has a great post this week with tips on moderating a panel. I’ve sat through enough boring panels to appreciate the tips Lisa has here, and this is a must read for anyone who resolved to more public speaking in the New Year.

Matthew Cynamon is joining Union Square Ventures working as their new Network Program Manager. He’s helping to unlock the value of their extended partner and alumni network to the portfolio. I love that he listed the books he’s using to ramp up in his post Nice to Meet You.

When Hard Work Pays Off

This is Kevin here. Last week a short, but impactful chapter in my life came full circle.

By November 2011, I was at a low point in life. My mom had passed away two years before. Danielle and I had moved to San Francisco, and I had made hardly any friends. I missed my friends from being in Seattle for 30 years. With the move, I had started a consultancy which eventually became a startup. By the end of 2011 it was clear that too wasn’t working. I had burned through my life savings. I swallowed my pride, shut down my failed startup, and started looking for a job.

I joined a company called HelloFax. They had the two cofounders and two other engineers. The five of us worked out of a studio apartment in the Lower Haight. Right away, it was a refreshing change from working on a stalled startup: we were making revenue, and our customers loved us. More over, it was a breath of fresh air to be working with a team again. When we weren’t busy coding, we were joking around.

I remember being struck by the CEO Joseph Walla. I would bounce ideas off of him about crazy things we could be doing. “Joseph why aren’t we doing advertising; we could be growing so much faster! Or why don’t we invest in something to make the signatures look better.” He was unflappable though, and couldn’t be deterred from his vision. I watched as he took early UI designs that were too complex and spent hours honing them down to something elegant.

He wanted to keep all his employees unimpeded, and so it wasn’t uncommon for him to take out the garbage in the morning (he was too frugal to hire a janitor).

When Danielle pitched me on cofounding Referly together six months later, my greatest reservation was that I’d have to give up working with the HelloFax team. I did decide to leave, and my last commit to the code base was helping to rebrand them to HelloSign.

I kept in touch with Joseph over the years, and was always impressed with his unwavering focus and commitment to his company. I wasn’t surprised to see this week that he announced HelloSign has been acquired by Dropbox. It made me so happy to wake up to the news and see that all their hard work had paid off. Congratulations Joseph and the HelloSign team!

It’s Turtles All The Way Down

We have a great post this week from the founder of Thumbtack, who shares lessons on over a decade building the company. Most “lessons” posts serve up platitudes, but Jonathan’s post has a number a unique ideas. My favorite: he’s built multiple companies along the way 1) the startup hunting for basic product-market-fit 2) the startup hunting for business-model-market-fit 3) the startup hyperscaling 4) the startup building out a leadership team. There’s a new challenge just when you feel you’ve got the hang of it.

From the Operators

Jonathan Swanson of Thumbtack recounts Thumbtack’s wild ride in Zero to $1B: 8 Lessons Scaling a Startup.

Anand Iyer of Trusted shares An important Marketplace Metric: Search to Fill. Don’t be deterred by the Uber example at the beginning, this pieces goes deep on the math you need to corner your marketplace.

Andy Sparks of Holloway and his team at Holloway have put together the The Holloway Guide to Raising Venture Capital. It’s the definitive guide to raising.


From the Investors

Bijan Sabet of Spark Capital memorializes the passing of Mary Oliver. If you haven’t read her, Bijan found a good poem to start with.

This week Twitter was all upset about Ryan Hoover’s search for the Weekend Fund Chief of Staff, but Jason Calacanis sets them straight with a primer on carry in A carry comp kerfuffle in Micro VC land.

500 Startups recently published their 2018 wrap up, and we were surprised to see how many unicorns they’ve funded over the years. Add these startups to your index of unicorns: Credit Karma, Talkdesk, Twilio, Grab, Sendgrid, Canva, Intercom, Bukalapak, Gitlab, Revolution Precrafted

Hunter Walk of Homebrew says “Podcast Discovery” Is A Problem But It’s Not A Company. I’m a bit sad, because I want a collaborative filtering solution for podcasts, and Breaker isn’t quite there.

Gené Teare of Crunchbase reports that 2018 Sets All-Time High For Investment Dollars Into Female-Founded Startups. It’s so refreshing to see this happening.

Playing chess without seeing the board

This week two of our favorite videos comes from hours of great conversation last week with our former cofounder and great friend Andy Sparks. The first ponders how our typical approaches to strategy might be like playing chess without being able to see the chess board. And we also have a great video from one of the most experienced COO’s in startups, Keith Rabois.

We hope all of you are off to a great start in 2019!


From the Operators

Simon Wardley of Leading Edge Forum asks what would it like to be playing chess without being able to see the chess board or know the rules. It turns out this mode of blind thinking is where most business advice comes from. Situation Normal, Everything Must Change is humorous talk worth seeing.

Thompson Aderinkomi of Nice Healthcare tells the story of being fired as a CEO only to watch his company be shuttered months later. As if that wasn’t enough, he’s now recreating the company from scratch without venture scale funding. Read the full story at Indie and Me.


From the Investors

Keith Rabois of Khosla Ventures did a great talk called How to Operate several years ago. Enough people have recommended it that I finally checked it out, and boy is it a good one. We’re breaking our own rule that all content must be fresh, because Keith’s advice is so useful.

Dave Kellogg of Host Analytics shares A Simple Trick To Get Your CEO Closer to Your Team. Middle managers in companies with 50-200 employees can benefit from this tactic.

Shannon Liston of Techstars explains How To Shutter Your Startup: Best Practices for Corporate Dissolution. This is the tip of the iceberg, and we wish there was more written about this given how many founders we’ve seen wait to plan this until there are only 30-60 days of cash left.

Morgan Housel of Collaborative Fund wonders if our Wild Expectations for leadership are too high. She mentions a fascinating bit of history about Harry Truman taking over from Roosevelt I didn’t know about.


From the Authors

Jonathan Rosenberg of Five9 announced on Twitter his new book Trillion Dollar Coach, a collection of insights from Bill Campbell who coached Steve Jobs, Larry page, and probably dozens of other successful entrepreneurs.

Eliot Peper announced on Twitter his new novel Breach. His two preceding books Bandwidth and Borderless have been completely on point with our political situation and the challenges technology has introduced.