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Part II: The failure points from $5M to $100M in ARR

tracy.posthaven.com

101–110 of 127 posts

Re: Part II: The failure points from $5M to $100M in ARR

#101

Earlier quoted context omitted.

Given the lack of details, my guess is that your role at those startups is wildly different from your role at the middle-sized company and also that these aren't necessarily comparable companies outside of size and age. 3 is also a stupidly small sample size for what it's worth.

You're moving the goalposts, but keep on digging I guess. I suppose your anecdotal and theoretical stories trump Tracy's lived ones and mine as well. No reason to continue this discussion.

I'm not moving the goalpost, you are. You're not the only one with lived experience and having had a job and founded a couple of companies doesn't allow you to generalize to come to the conclusion that:

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

Because this simply isn't true. The point is also not that my experience trumps yours - the point is that this isn't generalizable and you're not comparing apples to apples.

Being at a startup doesn't have to be hard, at any level. And you and Tracy are certainly ascribing difficulties that arise from having responsibilities that are at times beyond your own capabilities and being extremely emotionally invested in the success of the company to being at a startup.

Re: Part II: The failure points from $5M to $100M in ARR

#102

Earlier quoted context omitted.

> If not for the PM, who will speak with the customers, gather, analyze and understand their needs and problems? The engineers? i.e. the people who will actually be fixing those problems? > Engineers or CEOs building features no one asked for is IMHO one of the major reasons lots of tech startups fail. So why put another layer (the PM) in between the engineers and the customers? Sounds like an unnecessary game of tel…

Yes, I continually dislike why engineers are so discounted in terms of parsing customer problems... we build the damn things, we also happen to know how to use the mobile apps, web apps, and desktop apps we build. I'm likely heavily biased and bitter at this point, but I've yet to work with a good "product manager" - and I still don't know what a good one would look like or do.

Sounds like you should work for a company that has only engineers and no PMs or middle managers. Maybe someone on HN can suggest a good one?

Re: Part II: The failure points from $5M to $100M in ARR

#103
post #35

Earlier quoted context omitted.

There are many shenanigans that startups can play to juice ARR to render it meaningless. The idea isn't terrible, but that's why I invoked Goodhart's Law. > After all, sales is sales and if you don't have repeatable sales you probably don't have much of anything. That's right, but you're missing the key that it's a necessary, but not sufficient requirement. When the pool of investments is 90% with ARR are honest and…

What are some of the shenanigans to juice ARR? I can think of a few; 1) make 2 year contracts cost the same as 1 year contracts (so you're lowering the price by 50% but get the number you want for your report today); 2) give incentives equal to the value of the contract (our software costs $30k but we'll give you $30k of AWS credits). Anything else to watch out for?

Two companies pay each other absurd amounts of money for their (nearly) zero marginal cost services, netting no money transferred, but loads of recurring revenue for each.

Your #2 hint at this, but paying more than lifetime value of a customer to acquire the customer.

Re: Part II: The failure points from $5M to $100M in ARR

#104
post #42

I hate this BS about A managers hire A people, B people hire C etc. This is total MBA thinking (I think it comes form GE, or at least they espoused it) on a forum where people routinely mock MBAs. 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" te…

> A managers hire A people, B people hire C etc If that is the case, how do the B people get jobs in the first place? Who hires them?

https://news.ycombinator.com/item?id=34357689

Re: Part II: The failure points from $5M to $100M in ARR

#105
post #100

Earlier quoted context omitted.

Given the lack of details, my guess is that your role at those startups is wildly different from your role at the middle-sized company and also that these aren't necessarily comparable companies outside of size and age. 3 is also a stupidly small sample size for what it's worth.

3 is greater than 0.

I'm not making a grandiose claim that being at a startup is indescribably hard. There are lots of hard jobs.

I've also had executive roles at startups, personally know tons of founders and tons of people that have worked in executive positions at startups and tons of other people that have worked in big tech companies, management consulting firms and investment banks, big law firms and so on. An executive role at a startup is simply not some type of outlier experience from a difficulty perspective. It all comes down to core competencies.

The issue here isn't that Tracy hired someone who doesn't have startup experience, but more that she hired someone who had been removed from day-to-day technical execution for decades, whose core competency at this point was dealing with bureaucratic complexity at a scale that simply didn't exist at her company and expected him to operate effectively at a level where you need to be significantly more hands-on.

This has nothing to do with startup vs big company. If you put this person as a line manager at a big tech company, it wouldn't go so well either. On the other hand, big tech L6/L7 type managers would be perfectly fine in these roles.

Not quite what I'm saying here but a similar perspective:

https://a16z.com/2010/04/21/why-is-it-hard-to-bring-big-comp...

Re: Part II: The failure points from $5M to $100M in ARR

#106

Earlier quoted context omitted.

> If not for the PM, who will speak with the customers, gather, analyze and understand their needs and problems? The engineers? i.e. the people who will actually be fixing those problems? > Engineers or CEOs building features no one asked for is IMHO one of the major reasons lots of tech startups fail. So why put another layer (the PM) in between the engineers and the customers? Sounds like an unnecessary game of tel…

The same reason when every year a new iPad comes out, you have a thread on Hacker News with engineers complaining they can’t run Kubernetes cluster on it even though it has the technical capability to do it. Engineers don’t understand iPad’s product positioning, that it’s not built for them and they’re not the target market. Want to get a portable Docker developer machine? MacBook Air is cheaper and lighter than a 12…

Apple famously manages to do this with no Product Managers in its hardware or core software development organizations.

Re: Part II: The failure points from $5M to $100M in ARR

#107

Earlier quoted context omitted.

> If not for the PM, who will speak with the customers, gather, analyze and understand their needs and problems? The engineers? i.e. the people who will actually be fixing those problems? > Engineers or CEOs building features no one asked for is IMHO one of the major reasons lots of tech startups fail. So why put another layer (the PM) in between the engineers and the customers? Sounds like an unnecessary game of tel…

I think you’re getting bad answers here. It’s not just about talking to customers and understanding what they want, it’s about taking that and matching it against bigger business goals, budgets, and priorities plus making sure you’re not duplicating or messing up things other teams are planning plus prioritizing within all the features all the customers want. If you have time to do all that then why is the company pa…

If you’re doing all that, the company could be paying you staff engineer or senior manager salaries?

Re: Part II: The failure points from $5M to $100M in ARR

#108

As employee #36 I lived through some of these things first hand and definitely agree with them (I think we were over 200 people when I left). 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 fo…

As an outsider to the tech industry, it seems to me that the Product Manager/Product Owner role seems to be not only the most BS role, but also the most damaging role? Considering that I saw a post a few weeks back, I saw a similar post (I think on HN itself) where PMs were being fired en masse, I wonder if there is any real utility with the product team, or if it's just a holdover from Google doing its thing back in…

I’ve worked with a few good product managers. I always equate PM to project manager which is totally different and typically useless in software development. The most useless BS role is when companies hire for scrum master.

Re: Part II: The failure points from $5M to $100M in ARR

#109

Earlier quoted context omitted.

Of course there is. If not for the PM, who will speak with the customers, gather, analyze and understand their needs and problems? There should be a person that drives the product in the right direction based on customer conversations. In the early stages founder is the product owner. But as the company grows, the role of the founder/CEO changes. You now build the people, and people build the business. Engineers or C…

> If not for the PM, who will speak with the customers, gather, analyze and understand their needs and problems? The engineers? i.e. the people who will actually be fixing those problems? > Engineers or CEOs building features no one asked for is IMHO one of the major reasons lots of tech startups fail. So why put another layer (the PM) in between the engineers and the customers? Sounds like an unnecessary game of tel…

You still need to aggregate and contextualize these in terms of overall business and product strategy. Yes, engineers can do that too and some percentage of engineers are good at this as well - and being able to understand and formulate product strategy can be an important part of an engineering leader's skill set - but that's not that common and ultimately you need some level of specialization and you can't run an org expecting everyone to be able to do everything.

I've done both Eng and Product and most engineers don't have sufficient understanding or appreciation for the importance of product strategy. It's also important to be able communicate strategy coherently at some scale, especially if execution isn't expected to be completely top-down. At some point, engineers just have too much else to do and you need coordination.

Edit: I'll also add that engineers aren't the only ones doing work - Product Managers are expected to be able to coordinate across functions and get everyone on the same page, not everything is about just providing input to engineers.

Re: Part II: The failure points from $5M to $100M in ARR

#110

Earlier quoted context omitted.

> If not for the PM, who will speak with the customers, gather, analyze and understand their needs and problems? The engineers? i.e. the people who will actually be fixing those problems? > Engineers or CEOs building features no one asked for is IMHO one of the major reasons lots of tech startups fail. So why put another layer (the PM) in between the engineers and the customers? Sounds like an unnecessary game of tel…

The same reason when every year a new iPad comes out, you have a thread on Hacker News with engineers complaining they can’t run Kubernetes cluster on it even though it has the technical capability to do it. Engineers don’t understand iPad’s product positioning, that it’s not built for them and they’re not the target market. Want to get a portable Docker developer machine? MacBook Air is cheaper and lighter than a 12…

Open ecosystems foster growth and innovation though. Yes, companies have tried making something hackable and failed but other companies have tried closed eco systems and failed.

There is a reason I have a PineWatch instead of an Apple watch or Fitbit and Wyze cams instead of Nest or Ring.

I want to build an encrypted local mesh network with my iPhone for emergencies, I'll probably just do it on Android and have a few spare phones for family though.

I guess it is a profit incentive vs building the future. Running a Kubernetes cluster on an iPad would be cool, like that poster who leveraged an iPhone for OCR'ing memes. [1]

1. https://news.ycombinator.com/item?id=34315782

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