My favorite books

I am a reader and appreciate getting recommendations from other book people.

Here are my favorite and most influential books in no particular order:

  1. Dune, by Frank Herbert
  2. 1984, by George Orwell
  3. The Player of Games, by Iain Banks
  4. Endurance: Shackleton’s Incredible Voyage, by Alfred Lansing
  5. Influence: The Psychology of Persuasion, by Robert Cialdini
  6. The Diamond Age: or, A Young Lady’s Illustrated Primer, by Neal Stephenson
  7. Watchmen, by Alan Moore
  8. Starting Strength, by Mark Rippetoe
  9. The Stand, by Stephen King
  10. The Elements of Style, by William Strunk and E.B. White
  11. Ready Player One, by Ernest Cline
  12. The Picture of Dorian Gray, by Oscar Wilde
  13. Dracula, by Bram Stoker

And these are kids’ books, but I still count them:

  1. Matilda, The BFG, The Witches, and Charlie and the Chocolate Factory, all by Roald Dahl
  2. A Wrinkle in Time, by Madeleine L’Engle
  3. The Phantom Tollbooth, by Norton Juster
  4. Scary Stories Treasury, by Alvin Schwartz and Stephen Gammell

For those of you on Goodreads, here’s the list.

The Enneagram in startups: finding your type

The Enneagram is a personality typing system that  I’ve found useful in evaluating founders and teams. It emerged near the 4th century but has gained recent popularity in companies for understanding personal and team dynamics.

Like any personality assessment, it’s not science. Yet it’s a useful tool in understanding your and other people’s tendencies in order to anticipate conflicts and harmonies in relationships.

In it, everyone has a primary personality number from 1 to 9, with a secondary wing to either side of it. E.g., you can be a 9/1 (“9 with a 1 wing”) or a 9/8 (“9 with an 8 wing”), but not a 9/4 (“9 with a 4 wing”).

Enneagram diagram simple

It looks kind of Satanic but I promise it’s not

My friend and coworker introduced me to the Enneagram a few years ago when we worked at the same startup (thanks, Isabella). It spread quickly around the company and gave us a set of shortcuts for how people might react and why they’re behaving in certain ways. Andy would be talking about politics again because he’s a 1, Ingrid would disappear into her designs for hours because she’s a 9, and Gina would want to organize spur-of-the moment excursions because she’s a 7.

Since I’ve moved onto venture capital I still use the Enneagram almost every day, although now it’s more to assess cofounder teams. Many of our decisions in early-stage investing center on the people: are they founding this company because they truly care about solving a problem, or because of the money? (Note that the former is the only correct answer). Are they rigid and perfectionistic, and thus may not react well to the ups and downs of startup life? Do they motivate through fear, inspiration, or friendship? All of these tendencies are reflected in the Enneagram.

Each type has a characteristic role, giving a quick high-level description of their tendencies:

Enneagram diagram

So how do you find your type?

Below I’ve tried to give a visual glimpse into the key characteristics, motivations, and fears of each type. It’s designed to give you a quick overview of each so you can begin to hone in on which one fits you.

However, the most accurate typing method is to skim through the Personality Types: Using the Enneagram for Self-Discovery book referenced on the final slide. If you have a decent idea of what your primary type is, read the sub-sections in the book. For example, if you think you’re a 1, read the specific section on the 1/9 and the 1/2 to see if either speaks to you.

Often people may relate to a type but it’s not until they read the specific sub-type information that they feel a true sense that the description is accurate.

Common reasons for mistyping yourself

  • Successful people tend to think they’re 3’s because 3’s value achievement. But plenty of high-ranking people span all Enneagram types.
  • Women get overtyped as 2’s because they tend to inherit caretaker roles. That’s not who they are; it’s what they do.
  • People type as they want to be, not as they truly are. Be honest with yourself.
  • Wings have significant influence. Donald Trump and Elon Musk are both type 8s, but Trump is an 8/7 and Musk is an 8/9. Big difference.

Key characteristics of each type

If you distill each type to its most obvious (both bad and good) traits, you get this:

Key characteristics of each Enneagram type

At a glance, which applies to you most?

Fears

Often it’s recognizing what you do when you’re stressed or in low health that tells you your type:

Enneagram fears by type

When you aren’t your best, how do you act?

Motivations

What drives you in your actions?

Enneagram motivations by type

Each type’s motivations are distinct.

My attempt to type famous tech CEOs failed at finding a 4 and a 2, so please tell me if you know of a fit:

Tech CEOs by Enneagram type

Also Jeff Bezos is totally an 8.

And if we’ve come this far and you still don’t know, maybe these Disney princesses will help you:

Disney princesses by Enneagram type

I’ll admit this was a little forced, but here’s my thinking: Sleeping Beauty’s kind, empathetic, and in often her head (9). Belle likes the pursuit of knowledge and sticks strongly to her values (1). Snow White is a natural caretaker, immediately falling into that role with the Seven Dwarfs (2). Cinderella overcomes all adversity to climb the societal ladder (3). Alice is dreamy, abstract, and artistic (4). Elsa is cold and physically isolates herself to be alone (5). Mulan is loyal above all else to family (6). Ariel seeks new experiences and is afraid of missing out (7). Jasmine is aggressive and says what’s on her mind, discarding convention (8).

Integration and disintegration

The lines on the Enneagram show where each type goes when a person is healthy or unhealthy.

If you are healthy, you move in the direction of integration and take on the good characteristics of the type to which you move. If you are unhealthy (i.e. extremely stressed), you move in the direction of disintegration and take on the bad characteristics of the type to which you move.

For example, healthy 8s move to 2 and become more focused on others, selfless, and heroic. Unhealthy 8s move to 5 and become reclusive and obsessive about hoarding knowledge and resources.

Enneagram directions of integration and disintegrationTriads

The triads are a bit much for a simple typing exercise, but for our purposes, understand that certain groups of types act in similar ways.

Decisionmaking: 8s, 9s, and 1s act on instinct. 2s, 3s, and 4s act on feelings. 5s, 6s, and 7s act on thinking.

Instinctual reactions: 8s, 9s, and 1s get angry. 2s, 3s, and 4s feel shame. 5s, 6s, and 7s feel fear and anxiety.

Enneagram triads

Now that you’ve gotten the summary, what do you think your type is? What about your subtype? How can you use that knowledge to improve your interactions with other people?

If you want to delve deeper

Personality Types: Using the Enneagram for Self-Discovery, by Don Richard Riso with Russ Hudson

InsideOut Enneagram: The Game-Changing Guide for Leaders, by Wendy Appel

Riso-Hudson Enneagram Type Indicator Test (RHETI) (costs $12 to take online and is a about thirty minutes of either/or choice questions)

Unwanted Advice to a Young VC on Meetings and Follow-Ups

I’m learning how to VC right now, and a friend who has been both an associate at a large VC firm and a founder gave me this advice. I figured I’d share the wealth.

1.  superb meeting etiquette

– don’t be late.

– don’t walk around checking your phone or your email

– just generally be present

– don’t look or act rushed, at all (you will be most of the time)

– don’t let a meeting go over time whether you are interested or not; keep time and politely remind and set expectations

2. superb meeting followup

– always do what you say and say what you’ll do

– say no quickly and concisely (which you’ll do 99% of time), and say why briefly

– when super annoying entrepreneurs ask followup questions to your “no” email, have a blog post or canned email that isn’t customized but that you’ve worked very hard on to send them, breaking down why no means no and to not pursue it further.

3. the interesting in-betweens

– people / teams / areas you are really curious about but can’t pull the trigger on: tell them, make a small calendar database, follow up every 3 months, and make notes and watch the numbers they tell you.  Force yourself to make explicit your hypothesis and whether they are managing to it.

Rev Boston’s 20 women in tech you need to know

Rev Boston 2015

We’re launching a new kind of women’s event this week at Accomplice called Rev Boston. Rev finds and supports the top 20 female VPs and directors in Boston. Consider yourself put on notice that these women will create something powerful very soon. Most of them aren’t household names the same way that men at the same career levels are, and that needs to change.

Rev connects these 20 women to each other at an intimate retreat and brings them resources and expert speakers tailored to them. These people are elite as individuals, so imagine the network effect of them combining forces.

Collage of the women of Rev 2015

The women of Rev 2015

You see a lot of “leadership development” for women these days, but these women are already leaders and successes. The obstacle isn’t a lack of developmental opportunities (there are some great programs in the community and in their companies), but rather access and visibility. Our goal with Rev is to provide both. (more…)

I tried Google Cardboard and it’s awesome

Google Cardboard multiple views

Google Cardboard is exciting because it makes virtual reality accessible to anyone with a smartphone and a few extra bucks. Sure, the Oculus is cool, but $200 for a headset is still steep for the average person. Google Cardboard is…well, cardboard. Viewers cost around $20. It’s virtual reality for the masses. You assemble it in a few minutes, pop your phone in, and seconds later you’re standing in your apartment saying “OH MY GOD…OH MY GOD…OH MY GOD” because the future is here.

At least that’s how I felt about it. That, and pretty nauseated. Those VR physics aren’t quite right yet. But overall, it was incredible.

Weirdly, Google does not make any Cardboard viewers. You have to get one from a third party. I picked this kit in black for $20, because style matters when you’re in the metaverse.  (more…)


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