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How my role as CTO has changed as we've grown from 1 to 100 engineers

engineering.gusto.com

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Re: How my role as CTO has changed as we've grown from 1 to 100 engineers

#61

Post by bdcravens »

eropple wrote: post #50
enraged_camel wrote: post #47

Earlier quoted context omitted.

>>people running successful startups don't have time to write about it This is both offensive and incorrect. Offensive because it implies that if someone manages to find the time to write about how they are running their company they probably aren’t successful. Incorrect because the startup world is in fact full of leaders who do manage to find the time to write about how they run their companies (kalzameus comes to…

Patrick works at Stripe. Before that, he consulted and ran a bingo card creator. I love the dude and his advice has been invaluable to me--but it has been invaluable because he is not a guy who has run startups, he's a guy who's had to make a buck.

Plus it seems his output (on his blog and here on HN) has decreased quite a bit since he moved to Stripe, so this validates what happens when you get busy.

Re: How my role as CTO has changed as we've grown from 1 to 100 engineers

#62

Post by stevehawk »

volaski wrote: post #28

it's refreshing to see someone who actually successfully scaled a company write an article about "here's how we did it", instead of bunch of failed entrepreneurs who write medium posts about why they think their startups failed to either feel better about themselves or to capitalize on their failure with the attention they get from the blog post (answer: they don't know why they feailed, and that's why they failed. T…

the thing is... it's a lot harder to succeed than to fail.. so the pool of people who can supply those articles is pretty limited..

Re: How my role as CTO has changed as we've grown from 1 to 100 engineers

#64

Post by legohead »

I was an engineer #1 hired by a "CTO" and we grew to 50 engineers. His story/growth didn't really change much, however. He was a coding machine, a true "10x engineer", and programmed day and night. He even started up a second company while working on the first. He built both codebases from scratch, and even re-wrote the first company's core codebase at one point.

He did attend exec meetings and make all major technical decisions, but I never really felt he had to grow into anything.

When we got big enough to start worrying about compliance, security, and HR tools, we did it together and moved on to the next thing.

Re: How my role as CTO has changed as we've grown from 1 to 100 engineers

#65

Post by volaski »

dasil003 wrote: post #59
volaski wrote: post #42

Earlier quoted context omitted.

you're right i'm being cynical, because i genuinely believe you have not much to learn from people who have failed but haven't succeeded yet. That said, there are PLENTY of successful people who used to be a failure. In fact 99% of the successful people have been a failure at some point in their life. THESE are the people you listen to. The things you read in the media about a genius who got it right on their first a…

How do define success? I get there are a lot of clueless Dunning-Kruger cases writing Medium posts who are so far from competence that their ideas are worthless to anyone else, but those cases are straw men. What about the people who have some modest success but haven’t created a household name? There’s a lot more of those out there and yet they seem to get less credibility than some middle manager at Google who real…

any success is a success as long as you truly believe it was a success deep inside.

Which means the people you're talking about are all success cases. You don't have to be a household name to be considered a success.

A food stand guy who makes a good living and has learned tons of things about life and street smarts is a huge success and we have much more to learn from those people than idiot VC funded startup entrepreneurs who con their way into raising capital and burn through all their money without making anything work. These people may even pretend they're a success by "acq-hiring" themselves to a larger company, but anyone who's actually been in a startup know that's all fake bullshit. If you get acq-hired you have failed, period. Don't listen to these people's advice either.

The specific category of people I'm criticizing are those who have nothing to show for themselves but failure. They write Medium articles on their way out, so that they can:

1. get a pat on the shoulder

2. get more exposure so that they can get a job now that they're jobless.

3. get more exposure so that they can use that false influence to keep their charade going.

4. just do what everyone else does (they genuinely think for some reason that writing a post-mortem is some sort of a ritual to celebrate the liquidation of their startup for which they raised tons of money from strangers)

Most genuine entrepreneurs I know don't do this. They instead try to analyze what they did wrong, but they're humble enough to not shout out loud to the world to listen to what they have to say about why they failed. They show the lessons learned through action, not through medium post.

Re: How my role as CTO has changed as we've grown from 1 to 100 engineers

#66

Post by newbie912 »

bdcravens wrote: post #61
eropple wrote: post #50

Earlier quoted context omitted.

Patrick works at Stripe. Before that, he consulted and ran a bingo card creator. I love the dude and his advice has been invaluable to me--but it has been invaluable because he is not a guy who has run startups, he's a guy who's had to make a buck.

Plus it seems his output (on his blog and here on HN) has decreased quite a bit since he moved to Stripe, so this validates what happens when you get busy.

Although a big part of his job is writing about similar topics, so you could also say he's still doing the same thing, only posting to a different end point and getting paid. That too is success.

Re: How my role as CTO has changed as we've grown from 1 to 100 engineers

#67

Post by jiveturkey »

zmitri wrote: post #34

How did you maintain compliance and security before you could have someone full time on it? How did you deal with audits? Did you hire an engineer full-time dedicated to this, outsource it, or do it yourself? (I ask because I do this now but at 8 people it's starting to take up too much of my time as CTO) How does it work at your size now?

I would argue, you need a security specialist at about the same time as you need a build pipeline specialist.

Re: How my role as CTO has changed as we've grown from 1 to 100 engineers

#68

Post by newbie912 »

timr wrote: post #37
volaski wrote: post #28

it's refreshing to see someone who actually successfully scaled a company write an article about "here's how we did it", instead of bunch of failed entrepreneurs who write medium posts about why they think their startups failed to either feel better about themselves or to capitalize on their failure with the attention they get from the blog post (answer: they don't know why they feailed, and that's why they failed. T…

"...instead of bunch of failed entrepreneurs who write medium posts about why they think their startups failed to either feel better about themselves or to capitalize on their failure with the attention they get from the blog post" That's really cynical. For a long time, people were complaining about the opposite on HN: you never heard about the failures, which leads to a massive selection bias. I've always felt that…

It's also well understood that we incorrectly attribute success to the individual and failure to externalities when measuring outcomes, so the successful entrepreneur says "be like me", while the failure lists a lot of factors. Accounting for bias means there's a lot more value in the latter.

Re: How my role as CTO has changed as we've grown from 1 to 100 engineers

#69

Post by kochthesecond »

seibelj wrote: post #60
yarper wrote: post #38

Earlier quoted context omitted.

Giving up coding is what you do for your team, so they don't have to deal with the half finished B grade work you did inbetween doing the serious shit they can't do

Wow! What an extraordinarily unhelpful and bad attitude you have

While crude, I believe he is right.

I have seen it too many times with project managers and now my CTO. Trying to still code and fix that terrible bug with already too little time. Ends up slowing down everyone because he never can get anything finished, or breaking things on a Thursday at 6:49pm because of the half baked solution he thought was good enough, but exploded in production, which he then has to spend 1 more hour fixing and 6 more hours cleaning up the aftermath. Spend your time reviewing and mentoring and try replacing yourself with someone who has time.

You now have important shit to do.

Re: How my role as CTO has changed as we've grown from 1 to 100 engineers

#70

Post by bdcravens »

enraged_camel wrote: post #47
dang wrote: post #33

Earlier quoted context omitted.

That would be great, but there's a structural limit: people running successful startups don't have time to write about it, while people who have wound down their companies do. When a company is going strong and HN sees a post like this, it's usually because they're hiring :)

>>people running successful startups don't have time to write about it This is both offensive and incorrect. Offensive because it implies that if someone manages to find the time to write about how they are running their company they probably aren’t successful. Incorrect because the startup world is in fact full of leaders who do manage to find the time to write about how they run their companies (kalzameus comes to…

patio11 (Patrick McKenzie of kalzumeus.com) hasn't blogged on his personal site since September 2017. His current blogging seems today to support Stripe's business objectives, as he publishes to their site.
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