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Startups

These days, entrepreneurs spend a lot of time thinking about scaling their products. No one wants to build the next Facebook only to watch their technical infrastructure crumble when user growth takes off.

Entrepreneurs rarely think as much or as deeply or as rigorously about how to scale their companies. Best practices for scaling human organizations are harder to find, and the whole endeavor feels much more like an art than a science.

Ben leaps into this information void with his latest blog post titled Taking the Mystery out of Scaling a Company. This post will be the first of a series Ben will write on this topic because each skill CEOs must learn to scale their companies—such as designing and rolling out re-organizations, hiring functional executives for functions they’ve never done personally, optimizing incentive systems, and so on—need a post (or three) of their own.

Ben Horowitz and I co-founded one of the first cloud computing companies which we named, appropriately enough, Loudcloud. So we’ve been thinking about the cloud longer than most folks. In fact, we had to call ourselves a “managed services provider” in those days since no one was talking about “cloud providers” in the year 2000. I have to say it’s gratifying to see both the cloud name and the cloud computing architecture going mainstream in the past few years.

This time around, we’re thinking about cloud computing as investors rather than entrepreneurs. On his blog, Ben walks through why we invested in Okta, our first cloud investment. We couldn’t be more excited.

Conventional wisdom: startups don’t have the time or dollars to invest in training. Training is only for big companies who can afford it, both cash- and time-wise.

Not surprisingly, Ben picks a fight with conventional wisdom in his latest post, Why Startups Should Train Their People. The post describes why and how even startups should invest in training. No company operates so flawlessly that the right training at the right time doesn’t make a huge, measurable difference.

A question I hear a lot at startup board meetings is this one: "is the current VP of Marketing or VP of Sales or CFO big enough to do this job in 18-24 months when we go international or need to build an indirect sales channel or do the roadshow for our IPO?"

While you always want the best executive team you can recruit, there are downsides to asking this question too early or in the wrong way. Ben enumerates the risks in his latest blog post The Scale Anticipation Fallacy, then offers his suggestions on the right way to evaluate and develop your executive team. 

(As you can tell, our blogging agenda for the next few months—and maybe longer if the fan mail keeps coming in—is a comprehensive set of posts on entrepreneurship, management, strategy, fund raising, and leadership. Coming soon: the return of my archive on these very topics. Stay tuned.)

When I introduced our venture firm on this blog in July, I wrote extensively about the types of entrepreneurs and companies we want to fund: technical founders, brilliant and motivated entrepreneurs, product-focused companies, and so on. I got widespread head nods on most of the criteria.

But many people were skeptical about the "founder-as-CEO" filter. To express their skepticism, people would ask me some variant of this central question: "shouldn't the founding CEO just get the company jump started, then recruit a professional CEO to drive once the company is up and running?" 

While we agree that startup CEOs and "grow the company" CEOs need dramatically different skill sets (a point Ben hinted at in his last blog post), we wanted lay out our thinking on why we prefer funding startups whose founding CEO plans to run the company for a good long time. Cue the hip hop.

My good friend Steve Blank does a great job of describing the metamorphosis a scalable startup needs to undergo to become a big company. During that metamorphosis, many startups hire executives from big companies to help scale the business. Some go on to do a good job. 

But I've seen more than a few of those big-time execs get organ-rejected within the first couple of months of the tranpslant. Ben published a post today about this exact phenomenon called Why is it Hard to Bring Big Company Execs into Little Companies

In the post, Ben dissects the reasons why big company execs can flounder in startups, how you can spot warning signs during the interview process, and (perhaps most importantly) what you need to do to integrate the freshly hired exec into your company. Read it to save yourself a lot of heartburn created by hiring the wrong exec or failing to do your part to integrate them into the company.  

My partner Ben and I have been active angel investors for years and now full-time venture capitalists for 9 months. But prior to that (and for most our lives), we've been entrepreneurs.

Now that we've sat on both sides of the table—and have spent more time with other venture capitalists—my partner Ben has a few observations to share about what he likes and dislikes about what some VCs do. Mostly what he dislikes. Though to be fair, he has recommendations for behavior he'd like to see instead, so it's not just a rant.

And yes, there's a quote from a rap artist (Dr. Dre, to be precise).