Learnings of a CEO: Wade Foster, Zapier

I'm not an investor so this is all anecdata from going through YC and having a close friend get to 100Ms in funding. My friend has obv hired an amazing exec team, but like thousands of things, he learned how to do it by reading, asking for advice and asking for help. Early stage he figured out how to get a 'technical cofounder' - literally got on the phone with 100 engineers (got me to screen like 3-5 to get a gist of what I was looking for). Of course, I was only just one source: for everything he had to figure out/study he got input from many sources.

They learn, they figure out what's important enough for them to put their time/attention, they delegate to talented people. I guess the quote 'A players hire A players and B players hire C players' applies too. They can tell who's an A player by setting the bar high enough to their standard.

I think there wont be a straight answer to this question - people who figure it out make huge companies and a lot of money as a reward for cracking this puzzle. Re:groupon then on top of that you have a couple of dice rolling and if your number doesn't hit you're out.

As your perceived worth goes up you start meeting more "interesting" people who want to help more, and of course they ultimately want something more from you.

So you eventually have a big network through this process, and at a certain level its not even about trading favors, but trading the potential for a favor. And with this support group you can answer almost any question, market trends, merger opportunities, fund raising access, its all there for you.

For the former, a lot of company scaling isn't really that hard - it's hard because it's busy, varied, and relentless, but it isn't like quantum physics where most people just can't neurologically handle it. You also have to do it if you want to keep your job so obviously there's strong incentive to learn.

Basically if you're willing to learn and adapt (often requires many humbling or embarrassing moments), you just figure it out.

lots of mentorship from investors and others with experience. Even the most famous young founders had a veteran executive running a lot of things behind the scenes. Steve Jobs had Mike Markkula, Eric Schmidt was running the show at Google, Facebook had Thiel and Sean Parker. This applies to pretty much every one of these companies

most of the startup myths about these companies are embellished because having a young prodigy founder is good for marketing. Of course some are never able to make the jump and get replaced by the board

1. You can't move from a small company to running a large company without being able to identify (eventually) where it works in one but not the other, so you must think critically.

2. Not being afraid to get it wrong also means not shying away from an admission that you need to improve and then doing so.

I think where a lot of people get it wrong is more static thinking. Applying what worked for you at the small company to the large and expecting it to work.

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As an aside, I see this all the time, it's not just a founder problem. I'm of the opinion that the reason agile mostly doesn't work is because well-meaning people don't actually know what good software dev looks like and reach out to prescriptions such as scrum. They form the belief that's the right way to do it and hang onto it, when in actuality if they'd make a few non-agile adjustments they may find themselves with a lot more success.

I've lead a few teams before and have a decade+ plus of experience at a range of companies so I had a pretty reasonable idea about what's out there, and I figured it was a small startup so I might be a good fit.

I got a pretty blunt response that they were looking for someone that had managed teams for over 5 years, preferably at a single org. Not unreasonable but when I looked at the CTO's linked in they had only ever managed their current startup and only for 3 years at the time of the discussion.

I just found it curious that they felt the job of CTO could be learned pretty much as you go, but anyone without their target experience wasn't even worth talking to.

It looks like they had major layoffs a year ago, and aren't making much of a dent in their space so it's quite possible that "survivorship bias" is a big part of it as well.

In the Groupon case, I pretty quickly see two key mistakes:

* not being willing to make a hard decision ("following the data" on short term metrics for something he said he knew didn't feel right as a long term decision)

* not being able to keep an eye on the long-term and change course when needed. He frames this as "it happened too fast" but also makes it sound like this wasn't one decision, but a whole series of them.

These are both classic new-leader mistakes, so maybe the version of Groupon that hadn't imploded in a parallel universe still made them but also learned from them just soon enough to prevent disaster.

Mistakes are inevitable, how you respond to them matters just as much.

Obviously they have to be smart but I think it's a lot about ambition to be willing to do what it takes. Most people simply don't have the drive to keep pushing forward once they have reached a certain level of wealth.

I honestly think that in all the companies I've been the all hands should've been a 5 minute read email, rather than yet another meeting that is splitting my day.

At least, thats the lesson I teach.