Hi folks,

This is the weekly digest for my blog, Irrational Exuberance. Reach out with thoughts on Twitter at @lethain, or reply to this email.

Posts from this week:

- 2019 - 2022 reading recap.
- 2022 in review.
- Hard to work with.

2019 - 2022 reading recap.

In 2018, I put together my book recommendations, and while I don’t currently have any ambition to reflesh that list (those are pretty timeless books!), I decided to collect the non-fiction books I’ve read since writing that list through the end of 2022, which is roughly 2019 through 2022 (I read much more fiction than non-fiction, but that’s not really what this blog is about). I’m certain that I’ll miss a few, but here is a fairly representative list, particularly those where I read a physical copy.

For books that I still think about somewhat frequently, I’ll preface with a star emoji, “⭐”.

• System Design Interview – An Insider’s Guide: Volume 2 by Alex Xu and Sahm Lam. I’ve gotten to know Alex Xu from a distance as someone doing interesting and very successful independent publishing work, and wanted to both support and learn from his work.
• System Design Interview – An insider’s guide by Alex Xu. Same as the previous book, although this is the first volume.
• Startup CXO by Matt Blumberg. I really like what this book aims to do, but I found it wasn’t quite at the right depth for me, personally.
• The End of Loyalty by Rick Wartzman. Interesting context behind the social contract between employees and businesses.
• ⭐ The Power Law by Sebastian Mallaby. I learned a lot about the history of venture capital from this book. It’s absolutely the history of venture capitalists from the perspective of venture capitalists, so take it with a grain of salt, but I enjoyed it.
• Amp It Up by Frank Slootman. An interesting read of one CEO’s perspective on good leadership. My personal opinion on “the value of intensity” has changed quite a bit over time (not in a consistent direction), and I appreciate reading folks’ opinions on it. More of an aspirational book than a tactical one.
• Doing Good Even Better by Edgar Stoesz. A primer on how to be an effective non-profit board member, which I read while refining my approach to personal altruism.
• Couples That Work by Jennifer Petriglieri. Read while looking for more perspectives on navigating dual career parenthood. I thought it was good, but I’m hard pressed to identify a novel takeaway that changed our approach. (The biggest idea–be explicit–was an idea we’d heard a lot.)
• Startup Wealth by Josh Maher.
• Fool’s Gold? by Scott Shane. A skeptical review of data on angel investing.
• Venture Deals by Brad Feld and Jason Mendelson.
• ⭐ The Bogleheads’ Guide to Investing by Mel Lindauer, Taylor Larimore, and Michael LeBoeuf. A useful summayr of the approach to personal finance that we follow as a family.
• The Trauma of Everyday Life by Mark Epstein.
• Lean Analytics by Alistair Croll and Benjamin Yoskovitz.
• Empowered by Marty Cagan.
• Working Backwards by Colin Bryar and Bill Carr.
• Who: The A Method for Horing by Geoff Smart and Randy Street.
• Pivot by Jenny Blake.
• Ruined by Design by Mike Monteiro.
• Seeing Like a State by James Scott.
• Weinberg on Writing by Gerald Weinberg.
• How to Be an Antiracist by Ibram X. Kendi.
• The Unicorn Project by Gene Kim.
• Designing Data-Intensive Applications by Martin Kleppmann.
• White Fragility by Robin DiAngelo.
• Billion Dollar Brand Club by Lawrence Ingrassia.
• ⭐ All the Shah’s Men by Stephen Kinzer.
• Traction by Gino Wickman.
• Super Pumped by Mike Isaac.
• Building Evolutionary Architectures by Neal Ford, Rebecca Parsons, Patrick Kua.
• The Lean Product Playbook by Dan Olsen.
• Enterprise Strategy by Jeanne Ross, Peter Weill, David Robertson.
• The Principles of Scientific Management by Frederick Taylor.
• Secrets of Sand Hill Road by Scott Kupor, Eric Ries.
• The Broken Ladder by Keith Payne.
• Late Bloomers by Rich Karlgaard.
• ⭐ Escaping the Build Trap by Melissa Perri. I wrote up notes on this book when I finished reading it.
• Practical TLA+ by Hillel Wayne.
• The Rust Programming Language by Steve Klabnik, Carols Nichols.
• Angel by Jason Calacanis.
• ⭐ The Two-Income Trap by Elizabeth Warren, Amelia Warren Tyagi.
• Company of One by Paul Jarvis.
• Silk Road by Eileen Ormsby.
• ⭐ The Soul of A New Machine by Tracy Kiddler. I wrote notes on this one as well.
• Swipe to Unlock by Parth Detroja, Aditya Agashe, Neel Mehta.
• Move by Patty Azzarello.
• The Advantage by Patrick Lencioni. This is sort of a sumamry of his other books, many of which I love.
• Principles by Ray Dalio.
• What Works for Women at Work by Joan Williams, Rachel Dempsey, Anne-Mare Slaughter.

2022 in review.

Previously: 2021, 2020, 2019, 2018, 2017

Goals

Pull in 2021 goals and recap

Calm

• DK & acquisition
• growth/hiring

Infrastructure Engineer

background, links, stats, etc

Staff Engineer

stats

An Elegant Puzzle

stats

Irrational Exuberance

stats

CTO & VPE Learning Circle

The CTO/VPE Learning circle that I put together in early 2020 is continuing to go well for its third year, still meeting every other week.

Angel Investing

• stats
• sequoia scout camp!
• companies I am invested in

Reading Books

Finish and publish 2018-2022 reading recap

Doing Less

• I’ve been trying to do less, lol

Hard to work with.

Managing teams has taught me a lot about my own behaviors and motivations. For example, I overworked for a long time. This left me continually teetering on the brink of burnout, and I had no energy left to absorb the typical sorts of organizational changes that happen at any company. Despite doing good work, I handled change poorly, and I picked up the reputation for being difficult to manage.

I’d like to say that I learned from my mistakes directly, but the honest version is that I came to understand this dynamic mostly through working with folks struggling from the same issue. After seeing it in others several times, I came to notice it in myself. This culminated in joining Stripe with the explicit goal of pacing myself to be more valuable after four years rather than getting exhausted after two years like I had at Uber.

Overworking is an interesting vice because it’s socially acceptable and some view it as a necessary precondition to outsized success. The category of “socially-acceptable professional vices” is an interesting one because these vices will hamper your career progress in non-obvious ways, and this is indeed my segue to the actual topic I want to dig into: individual who have higher standards for those around them than their organization supports.

It’s a truism that you always want to hire folks with very high standards, but I’ve seen a staggering number of folks fail in an organization primarily because they want to hold others to a higher standard than their organization’s management is willing to enforce.

I’ve seen this happen so many times in my own work, in friends’ work, and in emails that wind up in my inbox. A few examples:

• An interim Vice-President of Engineering (VPE) at a company whose CEO won’t finalize the role because one peer is upset they didn’t get the role. That peer has been struggling for some time, but the CEO doesn’t want to “rock the boat” so leaves them both lingering. Attempts to hold their peer accountable are viewed as “evidence they’re not ready” for permanent VPE role
• An engineering manager working with a product manager whose proposals are both very expensive to implement and misaligned with the company’s goals. The engineering manager flags the issue to product leadership and it gets reframed from a concern about the product manager’s performance into an issue of two peers not collaborating well. Both are pushed to “collaborate better” but the team’s impact remains poor
• Engineering directors at a company who instituted company-wide bar raisers because one of their peers was unwilling to maintain the shared hiring bar. The CTO was unwilling to hold that director accountable, so the other directors followed the only solution they could think of that wouldn’t be interpreted as “interpersonal conflict” by the avoidant CTO

As you look at enough of these scenarios, you can back out a common pattern. The main character is trying to do their job effectively, but can’t due to the low performance of a peer. They escalate to the appropriate manager to address the issue, but that manager transforms the performance issue into a relationship issue: it’s not that the peer isn’t performing, it’s just that the two of you don’t like each other. Instead of being the manager’s responsibility to resolve the performance issue, it’s now the main character’s responsibility. By attempting to drive accountability in their peer, the main character has blocked their own progress (“they’re just hard to work with”) without accomplishing anything.

What I’ve come to appreciate is that the appropriate manager is almost always aware of the underlying issue, and for some reason they’re simply unwilling to confront it. You think that you’re bringing a new problem to that manager to solve, but what you’re actually doing is trying to hold that manager accountable for not solving a known problem, which more often than not ends poorly when they’re more senior than you.

If you still want to have a direct discussion, you can usually have a direct conversation about why they’re comfortable maintaining the status quo. You can even add more context about how it’s impacting you or the team you work with. Sometimes this will lead to change, but it’s a slow process. You’re not going to change their mind overnight.

What I’ve found effective in these cases is to lead with constructive energy directed towards a positive outcome. Even if you can’t get your peer’s performance addressed directly, you can often overcome your peer’s bad performance by generating excitement in the direction you want to go. Enough excitement will give the resolution avoidant manager a way to solve their problem without actually engaging with the situation that they’re unwilling to address.

I know that folks don’t want this advice: it is unfair to be forced to overcome a peer’s poor performance, that’s the manager’s job, but work isn’t a perfect place. Success is finding a path forward among the options that actually exist. Grinding yourself down in frustration about paths not existing doesn’t solve anything. It may take a few tries to learn this lesson, I certainly devoted quite a few years to learning it the hard way.

That's all for now! Hope to hear your thoughts on Twitter at @lethain!