Buried Reads for Thanksgiving 2019

It’s been a busy month of team off-sites, friends visiting from out of town and holidays parties. All of it has gotten me thinking a lot about how to make conversations more interesting and ultimately thoughtful. I wrote about it this week in a post called Kevin questions. If you want to get more out of talking with your family and dinner guests today, it’s a fun technique.

Our whole crew getting ready for Thanksgiving, from left to right, Kevin, Danielle, Emo, Andy and Taco.

From the Founders

Our friends at Holloway have been busy pulling together the ultimate book on Technical Recruiting and Hiring. Last week it just went public, and as an early reviewer and contributor I am impressed how comprehensively it pulls together what you would need as a founder to build your team.

From the Investors

This week, Version One Ventures published their Startup Handbook, which zooms in on how to build your team and investor base after a seed all the way up to Series B. I love that Boris and Angela keep publishing guides like this as well as their Guide to Marketplaces.

Kevin questions

I grew up extremely shy. My parents divorcing at an early age probably had something to do with it. With a single working parent and all older siblings, I spent a lot of time alone waiting for the rest of the family to come home. I remember long stretches of solitude, and so for years most social graces much less the art of conversation was baffling to me. During my 20s and 30s I worked extensively to get better at participating in conversations.

A few years ago, a friend Jonathan said to me, “you ask the strangest questions. We should call them ‘Kevin’ questions.” A typical question from me might be something like:

If we were telling the story of your life, and we did a cold open–at the height of dramatic tensions–what scene in your life would it likely be?


What’s something your significant other has taught you the most about in life?

My friend and I started chatting about these questions, and ended up figuring out that there was a measurable pattern. The first thing we realized is they’re almost always personal. A lot of conversation in life is very impersonal, whether you’re talking about the weather or something heated liked politics/religions, it’s about something out there in the world. It doesn’t require the person to really think about what’s going on in their world. Not surprisingly, people really like thinking and talking about themselves.

I also started realizing that a lot of conversation is really associative. We’re talking about this one thing, say flannel, and it makes me think about a girlfriend who used to wear flannel shirts and how we argued all the time. So then I bring that up, and we spend the next five minutes talking about it. On the other hand, there are conversations where we’re skipping from one thing to the next perhaps under a common theme. For example you bring up something that annoys you about your manager, but then we start talking about the whole practice of management, and it forces us to think about that entire theme. I call this random access memory, where you have to think about everything you know about a certain topic to really contemplate what to say next. When I ask you “what’s your favorite movie of all time?” you have to try to quickly revisit all the movies you’ve ever seen. While you’re busy doing that, it often stirs up a lot of interesting memories. These conversations can require a lot of energy and focus, but they can also be rewarding since they get you think about all your lived experience and hopefully realizing some new insights.

My friend Jonathan and I ended up realizing “Kevin” questions are something like the following:

Ever since realizing this, I’ll take a surface level moment amongst friend and figure out a way to explore something we’re already talking about deeper. If we’re talking about the weather, instead of staying at the shallow end, I’ll ask something like “what was your favorite snow day as a kid?”

These conversations end up having several benefits. Not only do you tend to realize deeper insights since you’re not just fleeting from one associative memory to the next. They also have the benefit of really drawing someone into the conversation, since you’re asking them something personal.

Realizing this phenomenon has taken from me from a shy introvert to someone that draws energy from conversation.

More example questions

What is the TED talk you’ve been preparing to give your whole life? Assume that whatever you have to talk about people will show up, so no filter.

There are some things in life we do that are just to check a box so we can live up to others’ expectations. What box that you checked do you most regret?

Buried Reads for August 17, 2019

With YC application season coming up, I thought it would be fun to share some tips that can help. Check out our post on the Buried Reads blog.

Quick PSA on Hiring

I just celebrated 6 months of working at Quizlet, and I’ve been loving it. Quizlet helps people practice and master anything they’re trying to learn. Two thirds of US high school students use the app every month, and if you talk to anyone under 30 there’s a good chance they’ll tell you it saved their bacon in high school and college.

Our team at a recent karaoke outing during our offsite.

Since joining I’ve fallen in love with the culture. Everyone is caring, celebrates success, and knows what they’re doing when it comes to their craft. I’ve also been impressed by how fast the product and engineering teams turn the crank each sprint despite being a relatively large organization.

We’re hiring in product, engineering and recruiting across both San Francisco and Denver. If you are interested or know someone that is, email me directly and I am happy to jump on a call or connect you directly with the position’s hiring manager.

From the Operators

Joel Gascoigne of Buffer deserves a ton of credit for being one of the most transparent startup bloggers. This week, he shares his company’s experience diversifying into three products, and what MRR looks like overtime in Buffer’s Evolution and Expansion.

Tim Chen of NerdWallet sat down with the editors of First Round Review to share lessons learned from the first ten years of NerdWallet. The advice for CEOs that lands the strongest with me: after product market fit, the company itself is the product you work on as the CEO. They should resist the temptation to meddle in product by this point.

Neel Desail of ProfitWell pulls back the curtain on ProfitWell’s data set to show “How is CAC changing over time?” While his approach is a bit cooky, maybe Chamath Palihapitiya is right that Facebook and Google (along with San Francisco commercial real estate) are eating most of the VC money coming from Sand Hill Road.

Nathan Barry of ConvertKit just took a week off to learn to sail in the San Francisco Bay. His video is a fun, light-hearted way to spend 5 minutes this weekend.

From the Investors

Ali Hamed of CoVenture goes a layer deeper into the well-chronicled trend of companies staying private longer in What Will The People of 2040, Wish They Had Been Doing in 2019. He suggests that if Michael Milken were starting out as an investor today, he’d be creating a bond market for late stage startups. If you don’t know about Milken’s work on bonds during the 80s, he’s worth reading about.

Dave Kellogg of Host Analytics shares his advice to potential startup employees in Things to Avoid in Selecting an Executive-Level Job at a Software Startup. Those considering joining exec teams can save hundreds of hours of wasted time and grief with this post.

Jeffrey Carter of West Loop Ventures presages what will happen to Small Investors on The Capitalization Table after institutional investors lead bigger rounds. If you are a new angel investor (or have any on your own cap table), this is a great read to gain a better understanding of the pressures and challenges they face.

An Unofficial Guide to YC Applications

Image result for ycombinator logo

Startup accelerator Y Combinator is accepting applications until September 25th for the upcoming batch. Danielle and I went through YC in Summer of 2012, and since then we’ve helped review thousands of YC applications.

YC applications are confidential, so I won’t share any quotes, but I can share patterns I’ve found that work. I feel comfortable sharing them, because they aren’t a hack to sneak through the application process–they’re a hack to make your company more successful.


Founders find themselves communicating all the time: with customers, early investors, and employees. The best founders turn complex topics into simple ones. If you can’t explain what you do in a single sentence with no B.S., you’re doomed. The best founders work hard to reach mental clarity and cut through the noise to quickly explain any issue about their company. They are judged on whether they can explain what their company does, because they should have spent significant time thinking about, refining and explaining the company’s mission long before speaking to YC interviewers.

It’s telling that the H1 heading on airbnb.com is something a five year old could understand, “Book unique places to stay and things to do.” There’s no mention of buzzwords like “marketplace” or “platform.” The “What is your company going to make?” and video portion of the application should both provide something as clear and succinct.

(Airbnb has come a long way from the tagline “a friend, not a front desk” in 2008 — check out the original airbedandbreakfast.com website on the Internet Archive)


All founders are hopefully talking to customers and building a product to serve them. The best ones are maniacal about this though; they do it so intently and so often that they’ve started to learn what Peter Thiel calls secrets. In Thiel’s words a secret is “something important and unknown, something hard to do but doable.” Airbnb’s secret might be stated as, “it turns out people are willing to stay in someone’s guest room or on their couch, and the experience of meeting a host actually turns out to be magical.”

There is a question in the application, “What do you understand about your business that other companies in it just don’t get?” It’s a great place to share your secret. The best secrets don’t have to sound mysterious or shocking, but they should be something controversial. The Fortune 500 goliath you’ll someday be competing with would hear your secret and say, “No, you’re totally wrong the world doesn’t work that way,” but you will know something from talking to your customers that makes it right.


Founders that make it through the gauntlet of challenges have to convince their first customer to sign on, convince dozens of investors to invest in them, and convince hundreds of employees to join them. If you’re not extraordinarily persuasive, you’re probably going to fail. Any investor worth their salt wants to see this in action, and YC is no exception.

One idea for how to show this: as soon as you explain your idea in the application video, anticipate the doubts someone watching will have. “Now you’re probably thinking this won’t work because __?” or “I know you’re already thinking, this is just another ___.” One way that founders overcome these objections is with clear cut data. “We know it’s working because we’ve already signed up 100 users this month, and they’re three times more engaged than our closest competitor and we do it for a tenth of the cost.” It doesn’t have to be exactly those metrics, but something that casts you as a standout in your industry.

I got an interview! Now what?

If you’re lucky enough to get an interview, Gary Tan put together a great video on the three points to nail during the few minute you’ll get in front of YC partners. He was a partner for several years, and likely did hundreds of these.

Is that everything?

Definitely not! There are many other factors that matter. The strength and bond of your founding team is crucial. The clarity and succinctness of your pitch video is a huge factor. But if you do these three things well, you’ll be making a better business, and giving yourself a great shot at an interview with YC.

If you are applying or know someone that is, we’re happy to help you with your application or interview. Shoot us a Google Doc with your application at editor@buriedreads.com.

Shining your lighthouse

A few months back Danielle and I were at a happy hour with colleagues from work. Danielle and I had both recently joined the company through acquisition, and were just getting to know the engineers. One of the more introverted engineers struck up a conversation with Danielle. After chatting for quite a while, he said to her, “I should probably let you go talk to other people; I must be boring you.” She was taken aback, because the conversation had been fascinating to her. She said, “oh no, it’s actually really nice to talk to you, as I wasn’t really looking forward to the superficial conversations you usually get at an event like this. It’s a gift when an introvert shines their lighthouse on you.”

When she relayed the conversation, the thought of an introvert’s attention being akin to a lighthouse struck me. As an introvert myself, I kind of take it for granted that any conversation worth having is one worth focusing all my attention on. I sometimes forget that a lot of conversation for people is a bit like skipping a rock across water.

Since hearing the metaphor, I’ve made a point of having more conversations that go deeper. I am only realizing this year that’s sometimes a unique gift for the person you’re with.

My friend Andy and I were catching up on conversation dynamics, and started realizing you can think of each friendship having a sort of depth chart. Is this the kind of friend where you’re stuck at the surface and maybe only able to go a few feet deep. Or is this a friend where you regularly dive deep into what he calls the well of life. If you want to really run with the idea, you can think of depth in all kinds of dimensions. How philosophical a conversation is might be one dimension. How emotional or vulnerable it is are other alternatives.

Taking a more active role in steering relationships into interesting waters has been a fun adventure this year. I feel like I’m still just scratching the surface of what’s possible.

From the Operators

In Revenue Financing + Traditional Equity as the Future of Startup Funding, David Cummings of Atlanta Tech Village laments that there is “too much money is chasing too few high quality deals,” and proposes a model called revenue financing as a potential solution. While I think that’s a very valid option for many entrepreneurs, there’s a deep flaw in thinking only so many unicorns will start in a year. It’s at least conceivable that there are more great founders than ever, and more markets for them to enter than at any point in history.

From the Investors

Jason Lemkin of SaaStr illustrates why management teams that want to IPO someday have to get good at budget discipline in Zoom Had a Burn Rate Budget. So Should You.

It’s fairly common knowledge that negative net churn is a huge driver in SaaS businesses, Sammy Abdullah of Blossom Street Ventures explains the equivalent in ecommerce.

Jeffrey Carter of West Loop Ventures couches accounting as essentially a backward looking lens on a business, and draws the interesting parallel that really news media is not so different than accounting. I think it’s actually worse, and too much news intake is a sure fire way to over optimize fear circuits in your brain.

Reflections on Denver

Danielle has written two blog posts recently about our life after selling our startup and moving from San Francisco to Denver.

Building Your Life is the Creative Thing You’re Doing Right Now started to come to her after feeling a bit sad not to be building a new startup with some big ambitious idea. Our mutual friend Fawaz’s reaction became the title of the post. As someone who occasionally panics when I feel my own productive output isn’t far out ahead of consumption of things like media, his advice made me rethink how hard I am on myself.

This weekend, she also wrote and posted Post-Startup Life: Reflecting on My First 18 Months Living in Denver. She asked me after writing it, “did I share too much?” My thought is that most founders privately move on from these things despite lots of behind the scenes emotions and doubt. If more people wrote about their experience, more founders would understand their outcome or struggles are fairly common.

From the Investors

Om Malik of True Ventures wrote A Founder Metric That Matters. I’m a little more optimistic than he is that Dara Khosrowshahi uses Uber frequently. However, it was a gut check that I should use my own companies product more often.

Jason Lemkin of SaaStr answers What was your first meeting with an angel investor like? He ended up bungling it by asking for a steep valuation, and it’s a great reminder that understanding how your potential investors fund is structured is a great way to know how far you can stretch valuations or limit their ownership percentage.

From the Operators

Fred Wilson turned us on to the post A No B.S. Guide to Startup Stock Option Grants by Matt Cooper of Skillshare. It delivers on exactly what its title promises, and is on of the more detailed, explicit blog posts I’ve seen on the topic.

Living All the Decades

Sometime around 1999 I heard about a British television series called 7 Up. It got started in 1964, and the premise was to take a group of about twenty 7 year olds and interview them. They were asked what they wanted to be when they grew up, what they thought of the opposite sex, and what they thought about politics. The show was originally an exploration of the famous Aristotle, “Give me a child until he is 7 and I will show you the man.”

I was 21 by the time I heard about the series. I remember binge watching ages 7, 14, 21, 28 and 35. A few years later, I got to see 42 Up when it was accessible to American audiences. The show immediately gave me a preview of what was coming in life. I remember watching the first couple 42 year olds grappling with the death of their parents, and I knew “this too is coming for me.” And so when my mom passed away in 2009, it was certainly emotional, but the show somehow prepared me that this is a  universally human phenomenon and I wasn’t alone.

One of the theories I’ve since developed is that you can have a primitive form of time travel in life. You can play with Legos for an afternoon and be a kid again. You can go to a Van Morrison concert and live in your parents generation as a 50 or 60 year old. A trip to Vegas can be a bit like being a 20 year old in a fraternity or sorority. For those that grew up in dysfunctional families, the 20s are often a time of healing and self development. In your 30s you figure out what habits you want to settle into, and which social norms you want to rebel against.

While it’s important to be your own age and live in the moment, it’s also true that at any given moment all the decades of life are accessible to you.

Watching 63 Up this week, and also seeing the popular appeal of FaceApp has got me thinking about Living All the Decades again this week. It’s fun to take an active role in balancing the portfolio of experiences you live in life.

Startup Links

Two great startup reads hit our radar since we last wrote.

Justin Kan of Atrium offers several helpful tips about Debugging Your Startup. None of the best practices are shocking, but when things aren’t clicking it’s helpful to have a checklist in front of you for the most likely things to consider.

Jamie McGurk of Andreessen Horowitz has a great post All About Direct Listings. For companies like Slack who don’t necessarily need the capital infusion, much less the headache of a roadshow, this is a route to have in your back pocket.

Complete Staff Work in Software Teams

During WWII, while serving as a staff officer Dwight Eisenhower developed the idea of Complete Staff Work. The idea is written up well in The Characteristics Traits And Skills Of The Successful CEO. I think the idea need not just be for CEOs and their directs, everyone from an organization could benefit. The idea is that when communicating with your manager it should include all the necessary research organized into clear thinking. Specifically, it should include:

  • Identify the decision to be made;
  • Identify the stakeholders in that decision;
  • Identify the constraints and resources available;
  • Frame the question and obtain input from the stakeholders;
  • Review and evaluate all of the possible decisions including doing nothing;
  • Present the decision to the decider with all of the alternatives fully discussed
  • Make a single recommendation, explain why and be prepared to defend it

I would add a few more specific to software teams:

  • If multiple teams are involved:
    • Who owns which parts?
    • What are the cross team dependencies? When will upstream dependencies be completed for downstream partners?
  • How will progress be measured? How do we get feedback throughout on how we’re doing?

It’s a tough bar, I definitely don’t always do these things when taking ideas to my own manager. For example, I a couple times I’ve asked if we can get budget for activities without bringing a clear value prop and project plan to the table. It’s hard to argue that it would be better for everyone if I consistently did this right. Or at least if I was gathering input from her, to tell her that’s what I’m doing, and I’ll bring back a full proposal later.

Several great things happen as people start doing this.

  • Manager and employee don’t have to go back and forth playing 20 questions
  • The organization makes better and faster decisions
  • The employee prepares themselves to be promoted to be the manager

The core idea of complete staff work doesn’t have solely for proposals. It’s can also be thought of as really doing the complete job when being delegated something, and at every twist and turn figuring out “if my manager wasn’t here, what would I do to take this all the way to the finish line?”

This is something I notice in standups a lot where updates often communicate activity, but not meaningful executive insight and recommendations. A good example of how this shows up in standups for software organizations: “I got pulled into a this issue with our production server yesterday, we finally got it fixed.” The manager is left wondering several things, “what do we need to do to prevent this surprise issue in the future? Do we have the right staffing and role assignment in place? What about the work you forsook to do this? Presumably it’s now off track and not going to come in on deadline. Who do we need to tell about that? Is there a mitigation plan we can compose to keep the project on track? If not, tell me you thought that through and that we should expect this work to be back in the next sprint.

Part of how employees can master this is to look at the questions that get asked when they do bring half baked plans to the table. If you keep getting asked a question, start preempting it. Another helpful tip is to think backwards from your company/team OKRs all the way to your project. If you want to change something, does it positively affect OKRs? If it’s neutral or negative, is that because we have the wrong goals or your idea is maybe a bad one?

An easy objection to the notion of complete work is “hey this is going to make my job really hard!” or “does this mean I can’t just casually chat with my manager and get feedback?” One simplifying principle is to apply this principle of complete work when the stakes are highest, and know that you can relax a bit when the results at stake are less important. Also if you think it’s going to take you more time, think about all the questions your are saving yourself from having to volley with your manager–not to mention the time you’ll be saving for them.

I’m starting an experiment to work with my more Senior Engineers to have them try pushing the thinking a little bit further forward, and see if that speeds us up as a team.

Further Reading

The original memo from Eisenhower pages 1 and 2.

Jade Rubick, also writing from the perspective of an Engineering Manager, explains the idea and also mentions that you can break complete staff work down into iterative chunks so that it’s not such an overwhelming project to complete up with a fully complete answer to a wider issue.

Non-biological stem cells

My friends know that I’m fond of using stem cells as a metaphor for cities, companies, and parts of your life. These are the blobs of opportunity you come across in life where it seems like anything is possible, and growth is bound to occur.

For example in Denver, the Rhino district seems to be where all the stem cells in the city are. It’s where most my coffee meetings end up, and it’s also home to several amazing murals. Companies can have whole departments that are stem cells, and sometimes the best way to recruit at a large company like Google or Twitter is to show that you’re the stem cells of the company; this is where all the exciting new potential is.

This week I have a great link to share with you about stem cells.

From the Operators

I did work last week on vacation to look at the most popular Buried Reads posts so far. You all are really interested in whether and how entrepreneurs can be good parents. This week Avni Patel Thompson of Poppy shares how impactful her family’s nanny has been. Read her post Can we please talk about the truth behind how we “do it all”?.

When I came across Adrienne Tran of Tesla tweeting about increasing optionality through specialties, it immediately made me think about the stem cell metaphor I mentioned above.

From the Investors

Sarah Tavel of Benchmark Capital has a great tweetstorm on becoming a VC. You can tell reading it she’s capturing several hard won lessons. Personally, the long feedback cycles she mentions are why I think angel investing will always play second fiddle to coding for me. I thrive too much on quick wins.

This week Jeff Bussgang of Flybridge Capital Partners published his Rocket Ship Startup List. If you just graduated/dropped out of college and want to get into startups, take a look at Jeff’s list. But also if you join a company and feel like you’re riding Apollo 1 not 11, take it as a chance to learn. Before shipping Windows 3.1 and Windows 95, Brad Silverberg worked on the failed Lisa project at Apple. Before Danielle joined Twilio as employee one, she was working at a company that struggled mightily to get customers. Sometimes the failing companies teach you painful lessons where the drive of “never again” propels you more than ever.

I try not to cover headline news here, since I figured you all get enough of that already. But this week Brad Feld of Foundry Group has a great view from in the trenches on how tariffs are affecting hardware startups.

Startups and Star Trek

Sarah A. Downey of Accomplice has been hosting a regular blog series called Startup Trek. It features a single blog post on each episode of Star Trek the Next Generation. Every post covers a lesson learned on startups.

Earlier this Winter Daniellle and I made a regular affair of watching Startup the Next Generation before falling asleep. We both loved the show. Danielle admires Picard’s principled integrity, and I think Data is a fascinating exploration of AI and emotion. So we’ve watched Startup Trek with delight, and I asked Sarah if she’d be willing to let me write on up a post on one of the episodes. She politely offered, and I was blown away.

I chose one of the climactic episodes of Season 1 where the security chief Tasha dies. It ends up being an exploration of nihilism. How does this relate to startups? See the post Startup trek episode 22: Skin of Evil to see what I think it means for founders.

From the Investors

Uber’s IPO is starting out with a wild ride, and for those who follow public offerings we highly recommend The Impact of Short Interest on the Performance of Tech Initial Public Offerings in the U.S. to provide helpful context on what to expect in the months leading up to the end of various lockup periods.

Struggling to put together a diverse panel, board, or recruiting strategy? HBCUvc’s List of Black, Latinx ‘Rising Stars In Venture Capital’ gives you the names, so now you have no excuse.

Sarah A. Downey of Accomplice who started Starutp Trek also wrote a great post this week on How to get a job in VC: the college student edition. She sums it up eloquently:

It’s not like a normal job function where there’s an ascending ladder of neat titles and constructed programs where you move up, like with investment banks or private equity firms that siphon up MBA students. Venture doesn’t really have that. Although some of the big firms might have associate programs, most don’t.

The number of jobs that come up annually is just a handful. There are roughly the same number of open U.S. professional athlete positions as there are available VC positions nationwide. And because of that scarcity, those jobs are always going to people who already have context around startups, their own deal flow, strong networks, unique talents, advisor or angel roles, or as many of the above as possible.

So how do you get a job in VC? It just kind of…happens. You don’t pick venture; venture picks you.

So You Think You’re Ready to Hire a Marketer? Read This First. It challenges the assumption that you need a marketer to launch, among many myths that cause founders to hire this role too early