Category: Uncategorized

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.

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.

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?

or

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?

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.

This week I’ve been thinking about the important connection you can build with employees.

Just recently, our longtime friend René Barranco opened his first business Element Bar in Panama. I first started working René at Microsoft in 2003. When I started growing the team at Mattermark in 2015, he was one of the first people I wanted to hire. We worked together there for several years, and he was universally loved by everyone at our company as an amazing engineer and a boundless source of optimism, fun and laughs–even a counsel in tough times. I hope in some small way we gave him the itch to start his own business, and it’s amazing to see it up and running this week. If you’re ever in Panama, he makes amazing cocktails!

Another longtime employee just hit the employment authorization stage of their visa process and is now in the final step to get their green card. This would make the 3rd green card that we were able to get for employees at Mattermark. The first two both had families, and it meant they didn’t have to completely upend their lives. It was life changing, and I can’t wait to see what they create in their adventures.

Whether or not your company survives, the relationships you build with employees can be a long lasting treasure you get to hold onto.

---

From the Operators

Sahil Lavingia of Gumroad shares his humbling journey from 19-year-old wunderkind founder to profitable and independent in Reflecting on My Failure to Build a Billion-Dollar Company

---

In a GIF laden post Frank Denbow tells his story of building his company, applying to YC, only to be rejected and discover what really gave him happiness. We’ve helped a bunch of people with YC interviews over the years, and while some make it, there’s always the possibility of that tough rejection email. Frank made it through to the next step, and we love his story.

---

Sarah A. Downey of Accomplice acknowledges that most VC are generalist, and she is looking to profile people who have deep domain expertise in Everyday Exceptional: seeking people who are awesome at something specific

---

From the Operators

Fred Wilson of Union Square Ventures has an interesting take on Raising A SAFE Or Convertible Note In Between Rounds. Fred talks about how this is a potential long term problem. Danielle and I talked about this, and she pointed out that VCs are using this as a stealth tactic to come in as a “white knight” and lock in companies.

OpenView Venture Partners reminds us why the NPS methodology has been widely discredited in Can’t We Do Better Than NPS?.

---

This week Ryan Hoover of Weekend Fund chronicles The Rise of “No Code”. I’ve believed for a long time that learning to be a web developer is way too complex relative to the days of Visual Basic dominating line of business applications, and the market is ripe for someone to retake this market. Disclosure: we’re proud investors in Retool.

---

Chip Hazard of X Factor Ventures takes a pulse on Female founders: Digging into the 2018 investment numbers. Danielle is a partner at X Factor, and actively fields pitches from female founded companies. If you’re working on one, reach out to her by replying to this email.

Morgan Housel of Collaborative Fund goes back to the moment early chemists figured out how to make bronze from copper and tin, both are relatively soft but suddently together they’re like magic. In my research for Buried Read’s , I keep coming across founders who needed a Steve Wozniak like personality to make it all come together. When you get cofounder alchemy right, it’s magic.

---

One last note, we are active on Twitter under @BuriedReads. We share posts beyond what we share here. Like Tomasz Tunguz’s post about Top 10 Learnings from the Redpoint Free Trial Survey.

Since launching Buried Reads in September, we’ve created a new newsletter for software engineers. Instead of linking to blog posts, Kevin decided to do his own original research and writing. The first edition is out: How Computing Came About. We went deep into history, back to the days when “Computer” was a job title held by humans. Early reviewers, even non-technical ones, told us they loved learning history they didn’t know about. We’re building an audience for more content like this, and hope you will subscribe and share with anyone you know who would enjoy this history.

---

From the Operators

2018 was the year of people resolving to use their phones less, stay away from Twitter, delete Facebook and perform various forms of “digital detox”. There’s clearly something to this, but I also believe this trend is swinging the pendulum too far the other way. Replace the word “phone” with “my connection to all human knowledge” and then try to talk about how pernicious it is with a straight face. Given this, I was elated to hear Sachin Monga formerly from Facebook offer some valuable perspective on wielding these new attention gravity devices in Screens & Time.

Ben Gilbert & David Rosenthal of Pioneer Square Labs kicked off Season 4 of their amazing podcast Acquired. This episode tells how ESPN got off the ground. It brought me back to the days before the Internet when cable was a welcome relief from the three major network channels.

Ting Ni and Hendrik Pretorius of ImmiPartner go in depth on transforming immigration HR from a nuisance to a strategic advantage. 70% of foreign candidates view a company’s green card policy as a major consideration when joining. At Mattermark, we took pride in working to secure green cards, and are so proud of being able to help families stay in the U.S. indefinitely.

Bob Crimmins of Startup Haven started a series on why founders should play poker. In Poker is “Wax On, Wax Off” for Startup Founders, he reminded us of a great quip from Peter Thiel: when everyone around you is taking shortcuts, you should dig deep and research from first principles. When everyone around you is moving slowly, you should find the shortcuts that cut through the noise. A classic lesson from the poker table that works in business too.

---

From the Investors

David Sacks of Craft Ventures posted a tweet this week soliciting off-the-shelf Series A docs. After seeing legal bills in excess of $100,000 to do a fairly standard Series A, we’d love to see the startup community optimize.

Tomasz Tunguz of Redpoint Ventures has a great distillation of Eugene Wei’s Novel Mental Models for Technology. Danielle had been reading The Theory of the Leisure Class this summer, and it took us back to how signaling shapes humans culture.

Sammy Abdullah of Blossom Street Ventures offers a seldom spoken truth: strategic investors can hurt you. Too few people talk about the strings that can come with this ”easier” money.

As a hiring manager, references checks scare Kevin. He was influenced by the advice that if a reference isn’t a screaming “Yes!” for a candidate, then it’s damning. On this basis, he almost turned away what ended up being his greatest engineering hire ever. He’s looking for ways to make reference checks work, and thinks the ideas from Bowery Capital in The 7 Do’s and Don’t of Sales Reference Checks are a good start.

Leo Polovets of Susa Ventures tweets a reminder that trust underlies our society and economy. We wish more economists and psychologists studied the inner mechanics of trust. The closest Kevin has found recently is Gottman’s The Science of Trust.

For founding teams that didn’t give away board seats to investors in early rounds, it is tempting to forgo board meetings. Jason Lemkin of SaaStr argues holding board meetings is a great way to secure investor commitment for follow on or at least a bridge in 5 Reasons to Actually Have Board Meetings.

Brigitte Hackler of High Alpha answers the perennial question from founders How Much Should You Burn. She’s doesn’t provide a single answer, but rather a framework using risk and distance from needing to raise again to help you come to your own answer. Later stage founders should think about the Rule of 40, which Dave Kellog wrote an awesome update on this week.

We’re loving the How I Built This podcast, hosted by NPR’s Guy Raz. In this week’s episode, Julie Rice and Elizabeth Cutler tell the story of starting SoulCycle. Raz asked pointedly, “why even bother starting Soul Cycle when practically every gym already had a cycling class for members at no additional cost.” This reminded me of the quip “if you’re entering a market with existing competitors, you have to be 10x better.”

It’s sound advice, and the founders of SoulCycle knew they could offer a 10x experience with just a few important changes. As Danielle can attest, from the moment you step into the studio the receptionist has been trained to make you feel welcome and accepted. When class ends and you’re dripping with sweat, the lights are low, candles are lit, and the instructors prompt you to celebrate how powerful your body is without comparing yourself to others. In short, you’ve had more than a ride — you’ve had an experience that to some even seems cult-like.

Sometime 10x better doesn’t mean 10x more work. Remember that just a few small tweaks in your work, or life, could make all the difference.

---

From the Operators

Andy Dunn of Bonobos recounts conversations with the late Blake Nordstrom, who passed away last week, in The Last Time I Saw Blake Nordstrom. Growing up in Seattle, I’ve heard so many stories about the Nordstrom family’s dedication to customer service, and you feel it when you’re a customer there. To hear it from Andy, the founder’s great grandson still had the touch, and will be dearly missed. Rest in peace Mr. Nordstrom.

Over the past month Nathan Barry of ConvertKit went through a difficult time, facing something not talked about nearly enough: his wife’s miscarriage. His surprising discovery that sometimes Gratitude is a distraction resonated with us, and his vulnerability in sharing this story is deeply appreciated.

First Round Capital compiled the best advice from First Round Review in 2018 in The 30 Best Pieces of Advice for Entrepreneurs in 2018. They’ve also conveniently linked back to previous years if you want to binge on the best nuggets from this top notch VC publication.

---

From the Investors

Jason Calacanis is back to blogging regularly and suggests The Ultimate Outsider’s Hack is to Read All The Biographies. This reminds us of the approach author Robert Greene takes to summarizing knowledge around human excellence in his great book Mastery.

David Teten of HOF Capital has the best non-obvious advice I’ve seen in a long time. Writing down your responses to VC’s doing diligence goes further in closing a deal than you might imagine. Find out why in Face-to-Face Meetings Are Important, but Thoughtful Written Collateral is Mandatory for Closing the Deal.

Jeffrey Carter of West Loop Ventures dives into another under-reported topic of fundraising, discussing investor’s : Information Rights

Carlos Eduardo Espinal of Seedcamp has a simple but awesome spreadsheet for Managing Your Fundraising Pipeline. Savvy founders can also fill this sheet with qualified VCs using the Investors tab of Mattermark.

Ali Hamed of CoVenture draws the distinction between Capital Efficient Vs. Equity Efficient. Either he’s dead on that financing growth needs more options or maybe founders should get more creative with their distribution approaches.

A warm congratulations to Dorothy Ren for joining NextView Ventures on the investment team. If you’re a founder re-designing the everyday economy (home, transportation, food, work & money, health, apparel, and entertainment) hit her up with a pitch (her email is in the post).