It was painful going through the enterprise focus transition along with a nonsensical reorg imposed by the aforementioned Big Tech VP. One day we had focused platform-specific teams working on satisfying customers, the next we were moved to cross-functional feature teams and focused on enterprise features that (from our perspective) no one ever asked for.

I also felt the sting from mediocre engineering managers. I remember sitting down with Tracy and Ralph at Uptown Bar and giving them both barrels on what I thought of several managers. To their credit those managers weren't working there very long after that conversation.

IIRC Ralph asked if I wanted to move to being a manager and I declined but in hindsight I think that was a mistake - we needed good management in engineering more than we needed my code.

Another thing that hurt us was hiring a bunch of PMs. Most of them were condescending, ignorant, or both... but suddenly they were telling the engineers who had built everything what to do? IIRC we could have cut that department down to two people with no loss.

The leader of this product team was a manager that just didn't seem to be doing his job, only pushing paperwork and giving scatterbrained presentations. I never did find out why he was kept on so long. I think I very cheekily asked Tracy one time which of his relatives worked at Y2K or Sequoia such that he couldn't be fired because it was clear everyone in engineering was fed up with his nonsense. I'm pretty sure at least several top engineers quit due to that guy specifically.

Either way I don't regret my time at PlanGrid. It was a great team and I'm proud of what the team did and what I did.

Most of us have been there in the painfull all-hands meeting falling asleep because the more people you have, the less they will care about the business. In a a team of 5, I have a lot of skin in the game and also a lot of influence. In a company with 100K employees, most of us are just a cog and some cogs don't even move anything!

Next is what I found most people doing differently from my ideal - abstract and refactor base on your existing implementation, not because of some framework doing it, nor because the previous project did it this way. Do you need a data access layer, a library, a folder, to talk to database where the first implementation was just storing things as a variable? You probably need a database and plain SQL. Do you need site reliability engineer to keep your site online while your traffic all comes from friends? Do you need a QA for testing? Or do you need a product manager where, as a founder, the value proposition has yet to be proven? How often do you see a code base spinning up all the folders/empty files because "we may need it". And how often when you hire someone, they spin up various incarnation people * time like teams, sprints, squad, function, BEFORE understanding the current implementation. This is why you hire the wrong people. And you know it only 1 year down the road. Wrong abstraction. Using framework has its appeal, where a cookie cutter solution mostly work. But it also has its limitation, bloat.

Once a wrong abstraction is in place, the more code/people depends on it, the more effort it takes to refactor

Theoretically applying all of those requirements to your product might make your product more secure, scalable, or reliable. It'll also make your product harder to maintain, harder to test, and harder to improve.

Many of those requirements are there because vendors put them there. If you're part of the RFP process (and you should be if you're actually selling to that sort of customer) you should be actively pushing back on requirements that you feel are pointless...making them optional instead of required, or at the very least providing a delivery date instead of delivering day 1.

In the enterprise space there's no guarantee you'll get the contract; to an extent the decision more political than technical. You should do a brutal assessment of your actual chances before engaging in any work implementing their requirements before the contract is signed. And since the sales cycle will be at least 6-9 months you'll have plenty of time to figure things out.

Lastly, if your product is highly desired the "requirements" can be bent or delayed. They're guidelines and can be overridden, if you have the right relationships.

In point one they list this. In point 3 he mentions his biggest mistake was hiring someone with starpower from a public company who didn't work.

Unless the founder is an A player in terms of recruiting everyone hired would be a C player or less. And in point 3 we learn he is not an A player.

How do B players ever get hired?

I'm currently knee-deep in the enterprise world, and trust me, the point about selling into these orgs is very true. My team just spent the last year moving our client off a Salesforce Lightning-based solution onto our custom-built one. No one in the org could tell us why they chose to build it in Lightning, but everyone now says they love our solution.

The lessons you learn building a startup are good and always usable, but you need to be ready to learn what it's like to work in and with an enterprise, to figure out how to adapt and sell your product to them. It's an arduous process, but worthwhile.

I have been lucky to work in a field where teams frequently work in parallel and success or failure is pretty clear cut. And teams are often stratified based on the priority of project. Many times-- not always -- the "B" team crushes the "A" team. Why? Some reasons include: the A team is performative and focused on the things that burnish the careers and reputation of its members. B teams have more of a sense of the wolf being at the door and that if they don't perform their task they will feel the consequence. Being underdogs promotes teamwork.

Obviously people have profound differences in their strengths and weaknesses and some people are completely inappropriate. But calling people stars or A player covers up a lot of lazy thinking that includes a lot of bias. I have worked at smaller startups that say "we only hire A players". Obviously that is delusional but worse it covered up the more profound questions. Why did you hire the wrong person? Why did that person or team fail?

Again, I get that the VC-backed status doesn't allow this, but that's such an interesting distinction - this would be a successful $50mill ARR business if not VC-backed, but since it is, the panic button is pressed and that thus leads to decisions and scrambling that upend a lot of what was working.

Guess we all (as usual) need to make decisions about capital sources early and how we want to grow, as well as the real trade-offs between those choices.

> Being at a startup is hard in a way that is almost indescribable to anyone who hasn’t experienced it.

Being at a startup as an employee isn't necessarily hard. You hear this type of "startup is so hard" because running companies well is hard and successful startups will often grow faster than their founders are able to grow their own ability to run companies, which makes their own job challenging. And a lot of startups are poorly run in ways that are entirely avoidable (often as a result of their CEOs not being able to grow as quickly as their company) which can make life hard for the employees as well. But this isn't a necessary part of the startup experience.

Seen it SO many times when startups decide they need "grownups" in big positions to be credible externally

(Added: My Ph.D. in mathematics is useful for something.)

An A player will still make hiring mistakes but they have the skills/ability/aura/whatever to convince other A players to come work with them.

Many A players won't want to work for/with a B or C player because they won't see this as a good opportunity.

Not sure if they actually meant that B players can't hire B players but maybe. This sort of framing is pretty high level though.

Fit matters. You wouldn't hire Jim Carey for a DiCaprio role.

It's clear you don't understand what A and B people are then. If the "B team" is crushing the "A Team", then they aren't the "B team". Also, notice how you switched "player" with "team"? The quote is "A players hire A players", not "team".

The point is that top tier individuals typically hire top tier individuals. The reason this notion isn't so clear cut is because its hard to identify A players before the fact. It's a retrospective truthism.

After spending multiple paragraphs about how they found that they had to dig much deeper into the background of every exec, getting 10+ references from reports, peers, and their managers, and developing specific lists of red flags . . .they end the section with: "Takeaway: Always trust your gut on people. "

Yes, for sure, if you 'gut' tells you something is off about someone, seriously consider and trust that also, but what was really effective was not gut-trusting, but gathering more hard data and observations to evaluate.

Just seems like the author didn't really think it through.

If that is the case, how do the B people get jobs in the first place? Who hires them?

Additionally, people who are not so good tend to be threatened by good people. So they will rather hire someone that won't threaten or "find them out". B hires C.

Contrast this with startup companies, where it's often required to explore and build completely new things from the thin air of the ether. I'm not saying other jobs don't also have elements of this, as new projects and opportunities do emerge, but being at a startup is definitely an extreme situation and arguably a different game. In the meta lens, it can be viewed as the act of mining the veins of market realities for golden ideas.

It's for the risk takers and adventurers. I've witnessed many a great engineer learn it's too undefined which can be uncomfortable, and is not a good fit for them.

It's nothing personal, along the exact same lines as some folks who can't stand working for a large company.

Different strokes and all that. This form of diversity is one of the beautiful things about the spectrum of humanity. In aggregate, it works!