A Scaling Magic Trick

By definition, as a company scales rapidly, it adds people quickly. There are many things about this that are difficult, but a vexing one has to do with the leadership team.

Often times, the wrong people are in senior positions. The faster a company grows, or the less experienced the CEO is (e.g. a first time founding CEO), the more likely it is a problem. Per Fred Wilson’s famous post What A CEO Doesthis is one of the three key responsibilities of a CEO.

“A CEO does only three things. Sets the overall vision and strategy of the company and communicates it to all stakeholders. Recruits, hires, and retains the very best talent for the company. Makes sure there is always enough cash in the bank.”

I’ve slightly modified in my brain to be that a great CEO has to do three things well. These three things. They can be great at many other things, but if they don’t do these three well, they won’t be successful long term.

Let’s focus on “recruits, hires, and retains the very best talent for the company.” This is where the vexing part comes in. As a company grows from 25 to 50 to 100 to 200 to 500 to 1000 people, the characteristics of who is the very best talent in leadership roles will change. It’s rarely the case that your leadership team at 1000 people is the same leadership team you had a 25 people. However, the CEO is often the same person, especially if it’s a founder.

Stress on fast growing companies comes from a lot of different places. The one that is often the largest, and creates the most second order issues, is the composition of the leadership team. More specifically, it’s specific people on the leadership who don’t have the scale experience their role requires at a particular moment in time.

Take a simple example. Imagine a 50 person company. Now, consider a VP Engineering who has never worked in a company smaller than 5,000 people. His last job was VP Engineering on top of a division representing 25% of the development resources of a very large company, reporting up to the division president. By definition he has never worked in a company that grew from 50 people to 100 people in a 12-month period. He might argue that he’s seen that kind of growth within a segment of the company, but he’s never experienced it working directly for a CEO of a small, rapidly growing company.

In comparison, consider a VP of Engineering who has worked in three different  companies. She started with one that grew from 20 to 200 and was acquired. The next one grew from 5 to 100 and then shrunk again to 10 before being acquired. The one you are recruiting her from grew from 100 to 1000 while she was in the role and is still going, but she’s now tired of the larger company dynamic and wants to get back to a smaller, fast growing company.

Which one sounds like a better fit? I hope you chose the second one – she’s a much better fit in my book.

Now, here’s the magic trick – if you are a CEO who is interviewing for a new member of your leadership team, ask the person you are interviewing if they have every been in the same role as a company that grew from size -50% to +200% of yours. So if you are the CEO of the 50 person company, you are looking for someone who has been in at least one company that grew from 25 to 100 people. Ideally, they participated in growth to a much larger scale, but at a minimum they should bracket these numbers.

Now, ask her to tell you the story of the company, the growth experience, how she built and managed her team, and how she interacted with the rest of the team. Keep digging into the dynamics she had with the CEO, with other executives, and with the people who worked for her. Focus a lot on a size you will be in a year so you know how she’s going to handle what’s in front of her.

Remember – you are looking for competence fit and culture fit. By using this approach, you are exploring both, in your current and near term context.

Book: The Curve

Yesterday was not an awesome day.

I was tired from my run on Saturday and a late-ish night so I slept in. Amy got up with the dogs. When I woke up, our country was deep in the fallout from the worst mass shooting in the history of the U.S. I was shocked by the shooting, then angry about some of the responses, and then ultimately – with Amy – just sad about the whole thing. Love is so much more powerful than hate, and there is so much hate in the world right now.

So I went for a long run. That didn’t help much so I took a nap and laid down on the couch and read the book at the top of my pile of infinite books. Other than being with Amy and seeing Mark Pincus and Dick Costolo in a cameo on Silicon Valley, reading The Curve was the best part of my day.

Jeremy Blachman, the co-author, wrote a book a decade ago called Anonymous Lawyer which I loved. It almost inspired me and my partner Jason to write a book titled Anonymous VC, but Jason decided to make the video I’m a VC instead. Jeremy sent me an advanced reader copy (ARC in the book trade) of The Curve so my simple task was to read it.

I enjoyed it a lot. I’m not a lawyer, but I’m surrounded by them (Jason used to be a lawyer and some of his best friends are lawyers). I didn’t go to law school but I’ve become very involved at CU Law and Silicon Flatirons around their entrepreneurship initiatives (Phil Weiser and Brad Bernthal are close friends.) I’m not deeply involved in politics, but about 25% of the people I interact with in politics went to law school.

The Curve is a super snarky take on law school. It chronicles the year of a fictional law school in New York – one at the bottom of the barrel. One of the protagonists is a first year law school teacher who quit his job as a high powered New York corporate lawyer to achieve more meaning in his life. The cliche “be careful what you wish for” comes immediately to mind.

It’s a fun, quick read. I enjoyed the dramatic twists, the sarcasm, and the characters, especially as the book cranked into the second half. Once it hit it’s full speed around page 100, there was no stopping it.

If you are a lawyer, or a law school student, or just know a bunch of lawyers and law school students, this book is for you.

And … this just in. Microsoft to buy LinkedIn for $26.2 billion. Nice job on the marathon Reid and Jeff!

vN – The AI Book That Should Be Turned Into A Movie

If you are a movie producer and you want to actually make an AI movie that helps people really understand one of the paths we could find ourselves going down in the next decade, read vN: The First Machine Dynasty by Madeline Ashby.

I’ve read a lot of sci-fi in the past few years that involves AI. William Hertling is my favorite writer in this domain right now (Ramez Naam is an extremely close second) although his newest book – Kill Process (which is about to be released) is a departure from AI for him (even though it’s not AI it’s amazing, so you should read it also).

I can’t remember who recommended Madeline Ashby and vN to me but I’ve been enjoying it on Audible over the past month while I’ve been running. I finished it today and had the “yup – this was great” reaction.

It’s an extremely uncomfortable book. I’ve been pondering the massive challenge we are going to have as a mixed society (non-augmented humans, augmented humans, and machines) for a while and this is the first book that I’ve read that feels like it could take place today. Ashby wrote this book in 2012 before the phrase AI got trendy again and I love that she refers to the machines as vNs (named after Von Neumann, with a delicious twist on the idea of a version number.)

I found the human / vN (organic / synthetic) sex dynamic to be overwhelming at times but a critically important underpinning of one of the major threads of the book. The mixed human / vN relationships, including those involved parenting vN children, had similar qualities to some of what I’ve read around racially mixed, religiously mixed, and same-sex parents.

I’ve hypothesized that the greatest human rights issue our species will face in the next 30 years is what it actually means to be human, and whether that means you should be treated differently, which traces back to Asimov’s three laws of robotics. Ashley’s concept of a Fail Safe, and the failure of the Fail Safe is a key part of this as it marks the moment when human control over the machines’ behavior fails. This happens through a variety of methods, including reprogramming, iterating (self-replication), and absorption of code through consuming other synthetic material (e.g. vN body parts, or even the entire vN.)

And then it starts to get complicated.

I’m going for a two hour run this morning so I’ll definitely get into the sequel, iD: The Second Machine Dynasty.

AI Screenplay Writing Has a Long Way to Go

Sunspring, the first known screenplay written by an AI, was produced recently. It is awesome. Awesomely awful. But it’s worth watching all ten minutes of it to get a taste of the gap between a great screenplay and something an AI can currently produce.

It is intense as ArsTechnica states, but that’s not because of the screenplay. It’s because of the incredible acting by Thomas Middleditch and Elisabeth Gray, who turned an almost illiterate script into an incredible five minute experience. Humphrey Ker, on the other hand, appears to just be a human prop.

AI has a very long way to go. But it’s going to get there very fast because it understands exponential curves.

 

Matching Grant to the Techstars Foundation to Help Improve Diversity In Entreprenership

For the next 90 days, Amy and I are matching every gift to the Techstars Foundation on a 1:2 basis up to $100,000 from us. Our overall goal is to raise at least $300,000 for the Techstars Foundation by the end of the summer.

If Techstars has touched you in any positive way, I’d request that you consider making a grant to the Techstars Foundation. This request includes anyone who has gone through a Techstars accelerator, done a Startup Weekend, participated in a Startup Week, receives Startup Digest, or has been a mentor or investor in any Techstars company or program. Or anyone else who has been positively motivated or influenced by Techstars in any way.

When we started Techstars in 2006, our goal was to change the way early stage company creation and innovation worked. While we didn’t have the words for it then, we’ve evolved the language and the mission of the organization over the last decade which we now summarize in the tagline “Techstars is the global ecosystem that helps entrepreneurs build great businesses”

As part of building this global ecosystem of entrepreneurs, I’ve observed and experienced a massive issue around diversity in entrepreneurship. This is not a new issue to me as I’ve been working with various organizations, such as National Center for Women & Information Technology, since 2005.

Last year, in a conversation with the Techstars leadership team, we decided to start the Techstars Foundation with the goal of improving diversity in entrepreneurship. While we were already doing lots of things internally around this, by creating the foundation we have taken it up a level, as evidenced by our first five grants that were made last month.

Amy and I decided to launch this challenge grant as part of a larger gift from us to the Techstars Foundation. We hope you join us and support our efforts.