[HN Gopher] Five years as a startup CTO: How, why, and was it wo...
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Five years as a startup CTO: How, why, and was it worth it? (2024)
Author : mooreds
Score : 103 points
Date : 2025-10-01 12:45 UTC (3 days ago)
(HTM) web link (distinctplace.com)
(TXT) w3m dump (distinctplace.com)
| laurent_du wrote:
| Good read, thank you. It feels nice to read something that was
| fully written by an actual human being.
| thrown-0825-1 wrote:
| where does the startup end and the small business begin?
| givemeethekeys wrote:
| A business is a startup when its goal is to raise investment
| with the understanding that it will use all the money towards
| rapid, aggressive growth, and then raise the next, much bigger
| round of investment, or get acquired, or go bust.
| gordonhart wrote:
| Solid definition. Being on the VC treadmill, and all of the
| "vibes" that come with that, is really what it boils down to.
| collingreen wrote:
| I like to say a startup is a business where growth is far
| and away the primary goal and it becomes a regular business
| as that shifts toward revenue or stability or
| specialization. I don't think it HAS to be VC but a big
| chunk of VC cash is a great way to bet everything on growth
| so it might be the defacto definition anyway and I'm
| splitting hairs.
| everybodyknows wrote:
| What's the current term then for a _newly founded_ business
| that is pursuing some other strategy? For instance,
| bootstrapping to organic growth, or self-funding toward a
| long-term profitable "lifestyle" business?
| jenadine wrote:
| A "new business" or a "small enterprise"
| dilyevsky wrote:
| By your definition OpenAI and Databricks are startups.
| mooreds wrote:
| Seeking or taking funding is my personal rule-of-thumb.
| palata wrote:
| My definition is that a startup hasn't found its product-market
| fit yet. As soon as you are profitable, you're a business,
| whether or not you take investments to grow faster.
|
| You're a startup when you're testing a new business model. If
| you realise that it works, then you're a business.
| Simon_O_Rourke wrote:
| I respect the honesty that went into that writing.
| mikert89 wrote:
| Generally speaking if you are capable of leading a startup as a
| CTO, you should just found your own, with the legal CEO
| designation, so that you can control what happens to the equity.
| CTOs in general are very naive about how all of this works once
| PMF/traction is hit, and how little power they have over the
| platform they built
| nextworddev wrote:
| One perhaps (cynical) view is that CEOs with business
| background are basically just arbitraging between investors and
| product teams.
| raincole wrote:
| I'm not sure if it's a cynical view. Isn't it what business
| guys do in most people's minds? To bring together investment,
| marketing and product because they don't just magically
| blend.
|
| I knew someone who chose to major business despite he got an
| offer for top biology degree in my country, for this exact
| reason. By the way, when he told me this decision we were
| both only 17.
|
| (I really should ask whether he still thinks that's what
| business is all about today though.)
| mikert89 wrote:
| Alot of CEOs dont start out thinking this way, but it
| definitely occurs to them as they run the business that its
| the case. Once the platform is built with sticky customers,
| the CTO is replaceable with a generic high performing
| engineering manager. Not always, but for run of the mill b2b
| saas, they are
| justapassenger wrote:
| CTOs just arbitrate between dev teams and product teams.
| mooreds wrote:
| CPAs just arbitrage between cash flows and legal
| requirements.
| mikert89 wrote:
| Nah, CTO is usually deep in the code base, hiring, firing,
| coding, pulling long hours to ship features, etc
| simonswords82 wrote:
| Yes! That's exactly what we're doing. It's not as easy as it
| sounds.
| nextworddev wrote:
| Definitely hard emotionally if the ceo job entails a lot of
| "managing up"
| Aurornis wrote:
| In the same way that engineers are just arbitraging between
| the company and the computers, I suppose.
|
| Every job sounds much easier from the outside.
| nextworddev wrote:
| Yeah. Everyone's just arbitraging. Not sure why the problem
| is
| mooreds wrote:
| Disagree.
|
| I helped found a startup[0] and have been around a number of
| them, in slacks and on email lists[1].
|
| I think that domain knowledge is so so important for startup
| success. Even more important than technical expertise.
|
| Why? Because the main problems for 0->1 startups are business
| problems, not technical ones:
|
| * where do possible customers hang out
|
| * what problems will they pay you to solve
|
| So in that case, a good CEO who knows the domain is critical.
| They'll have good answers to these questions, which will help
| guide the technical decisions. Or they'll know who to talk to
| in order to find the answers. There's no shortcut to that
| knowledge; you have to spend years to get experience in the
| domain. Learning and reading about the domain can help, but you
| still have to spend the time.
|
| The main exception, and it's a big one, is if you are building
| something in the devtools space, where you can be your own
| customer.
|
| 0: https://www.thefoodcorridor.com/ (I left after a few years,
| but they are still going strong!)
|
| 1: https://ctolunches.com/ (free email list for engineering
| leaders, so many good discussions happen there)
| mikert89 wrote:
| Right, sure, there is an initial pain of building domain
| knowledge. But that one year of knowledge building,
| distribution, early customers, then dominates who has control
| over the cap table for a decade. Why not just do this work
| yourself? Its some weird myth that someone capable of being a
| technical leader cannot also flesh out the distribution
|
| Especially with the existence of AI, it really makes no sense
| and is some weird hierarchical system built by business
| people
| abrichr wrote:
| > But that one year of knowledge building, distribution,
| early customers, then dominates who has control over the
| cap table for a decade.
|
| Can you recommend any resources for learning how to do this
| work yourself?
| mikert89 wrote:
| One shortcut would be to:
|
| 1. pick a vertical (construction, legal, accounting, etc)
|
| 2. look at how to apply ai (compliance, voice customer
| service, email)
|
| 3. find sales people from a would be competitor or old
| school b2b saas in that area, and pay them 150$ an hour
| to tell you what customers are paying for
|
| 4. at the direction of how to do sales, come up with the
| product and either do the sales yourself without
| building, or pay someone to do cold calls and pitch the
| product
|
| 5. build the product
| mooreds wrote:
| I'd recommend:
|
| - the lean startup: https://www.amazon.com/Lean-Startup-
| Entrepreneurs-Continuous...
|
| - Amy Hoy's blog: https://stackingthebricks.com/
|
| - working in the domain you are interested in for a year.
| Go be a realtor. Go work in a lawncare business. etc.
| etc.
|
| - read Patrick's advice about how he found customers for
| Appointment reminder:
| https://www.kalzumeus.com/2010/05/14/unveiling-my-second-
| pro...
|
| edit: added link to Patrick's piece
| mooreds wrote:
| Maybe AI has changed things, but I think it takes more than
| one year to gain sufficient domain expertise.
|
| But your argument still has validity even if it takes 2-3
| years to gain the knowledge, so let me address that.
|
| My response is: if I wanted to be an expert in <startup
| domain> to the point I didn't need a co-founder CEO, I
| would take the time, the years I mention above. But that
| has costs (opportunity costs if nothing else).
|
| Instead, I prefer to be an expert in software development.
| This gives me less control in each given startup as you
| point out, but more optionality across startups (and other
| companies)[0]. This choice also means that I give input on
| the hard decisions that company leadership has to make, but
| I don't have to make the final call. Frankly, that's more
| weight than I care to bear.
|
| That's a personal choice. I've watched friends be CEOs of
| successful startups and it's not always (nor usually, even)
| fun or easy.
|
| 0: I wrote more about that optionality here:
| https://www.mooreds.com/wordpress/archives/3445
| lurk2 wrote:
| > Its some weird myth that someone capable of being a
| technical leader cannot also flesh out the distribution
|
| This idea often gets repeated here but it's based on ZIRP
| from 2010s driving up developer salaries to a point where
| every kid with some portion of a CS degree thought he was
| the next Zuckerberg. "Technical" contributors became
| convinced they were the only contributors. Lots of stories
| about "idea guys" and useless upper management who Just
| Don't Get It (meanwhile most guys posting things like this
| have never even seen a balance sheet). It's a popular idea
| here because it establishes devs as the smartest guys in
| the room, but it doesn't have a lot of bearing on reality.
| Plenty of devs have neither the aptitude nor inclination to
| learn the business side of things, as evidenced by some of
| the lifers who post here about upper management.
|
| This attitude will change as market cools off, no code and
| LLM output improves, and overseas contractors become more
| accessible.
|
| > Especially with the existence of AI, it really makes no
| sense and is some weird hierarchical system built by
| business people
|
| LLM code output can be tested as it is generated, whereas
| its advice on accounting and contract law can only be
| tested by domain experts, who you can just pay for this
| advice without involving the LLM.
| mikert89 wrote:
| ycombinator, the best very early stage investors of all
| time hold this opinion:
|
| "If you are a technical founder, you do not need a non-
| technical cofounder."
|
| https://x.com/snowmaker/status/1948160642399314188
|
| Its really not up for debate, at this point it is a
| borderline scam to work for a CEO that isnt significantly
| better/bringing in capital. You are basically giving them
| free labor
| mjr00 wrote:
| You don't need a non-technical cofounder, but you _do_
| need a founder willing and capable of handling non-
| technical things.
|
| If nobody in your startup team wants to handle sales,
| marketing, finances, and business operations, you're
| going to end up with working software that nobody's
| paying for.
| bix6 wrote:
| Jared has an (unfinished?) degree in CS and Econ so
| that's a bit rich for him to say. Why'd he bother with
| Econ if it's so UsELeSs?
| CPLX wrote:
| What's YC's track record in the new LLMs-can-code era?
|
| Or are we talking about Dropbox and Airbnb?
| mikert89 wrote:
| most of the recent series A ai companies are YC
| companies, they are absolutely crushing it
| CPLX wrote:
| What are their names?
| kortilla wrote:
| >LLM code output can be tested as it is generated,
| whereas its advice on accounting and contract law can
| only be tested by domain experts, who you can just pay
| for this advice without involving the LLM.
|
| Assuming that passing some tests means it's good code is
| as dumb as asking the LLM accounting and contract law
| advice.
|
| It can be superficially correct and completely broken.
| mooreds wrote:
| > This idea often gets repeated here but it's based on
| ZIRP from 2010s ...
|
| I don't think it is just the ZIRP/2010s. Here's a post I
| wrote about developer arrogance in 2004, well before the
| ZIRP era: https://www.mooreds.com/wordpress/archives/134
| MrDarcy wrote:
| The best combination is a technical CEO founder with deep
| domain expertise. Confirms what you say about the dev tools
| space exception.
|
| Of which LLMs are effectively a dev tool that happens to also
| be a tool for every other industry vertical in the world
| economy.
| benzible wrote:
| 100% agree. I'm a CTO for a vertical SaaS, working with a
| first-time founder with deep domain expertise. He came in
| with a thesis as to why our target customer was still using
| Excel, even though it was completely unsuited to their needs.
| Almost everything he thought at the beginning has been borne
| out, and there's no way I would have figured out this market
| on my own. There's also no way he would have built a usable
| product without someone like me - his original plan was
| bloated and we narrowed it to the core where we have very
| specific value.
|
| I've been a solo founder as well multiple time co-founder /
| CTO at venture-backed startups so I'm certainly capable of
| starting something myself, but I think this combination is an
| excellent model. A couple of other things that make it work:
| the CEO has sales skills, and does not have much of an ego
| and is willing to listen to someone who has been through all
| of this multiple times.
| mooreds wrote:
| > A couple of other things that make it work: the CEO has
| sales skills, and does not have much of an ego and is
| willing to listen to someone who has been through all of
| this multiple times.
|
| Yeah! You definitely need to have a _good_ CEO as a
| partner. A bad CEO is worse than no partner at all.
|
| Those are some great attributes of what makes a good CEO
| and partner.
| etse wrote:
| I have hardly come across aspiring-CEOs who do not have
| much ego and listen to other founders, let alone founders
| or serial-founders. After some founder dating last year,
| I am a bit jaded, though.
| mikert89 wrote:
| yup
| parkaboy wrote:
| Also speaking from similiar experience, ^^^ this is the
| best combo. Where both parties have a certain degree of
| humility and self-awareness and understand how their
| skills, personalities, and personal circumstances (ability
| to travel, life stage, etc.) compliment one another.
| javier2 wrote:
| Just remember that every startup is not a SaaS business...
| nharada wrote:
| This may be your option for maximum control and leverage, but
| do remember that your day to day will be different, especially
| as the company grows. As someone who enjoys technical/product
| work and doesn't particularly enjoy fundraising, sales, or
| marketing, being the CEO is actually quite a trade-off for my
| personal fulfillment.
| mikert89 wrote:
| Sure, but you should just be aware that "wanting to do
| engineering" probably is stopping you from financial
| freedom/a more interesting life. Just be aware of the
| tradeoff
| nharada wrote:
| I find this a cynical and possibly incorrect take. I'll
| admit, if your goal is to become a billionaire and command
| vast sums of cash from your many vacation homes I'd agree
| with you, but financial freedom and an interesting life is
| absolutely within reach without having to take a career
| path that doesn't bring you fulfillment. Those CTOs that
| get pushed out once the company reaches their series C
| almost certainly achieve financial freedom.
| mikert89 wrote:
| I'm not really talking about unicorns, I am talking about
| some typical b2b saas that makes 500k-5M in ARR.
| Aurornis wrote:
| > some typical b2b saas that makes 500k-5M in ARR.
|
| The typical B2B SaaS startup never gets that far.
|
| You're looking at a survivorship bias subset. If someone
| had an automatic path to get to that promised land then
| it would be an easy choice, but it's never that easy.
|
| A 500K ARR SaaS is also hardly a path to financial
| freedom. That's too small to hire a competent engineer
| while also paying yourself a high salary, so you're
| basically on call all of the time. You're also doing
| sales, customer support, and possibly fretting a sudden
| 100K drop in your ARR if your biggest customer cancels
| their contract because the economy changes.
| mikert89 wrote:
| There is a non tangible level of status that comes with
| being CEO of a profitable startup. People dont know but
| it helps in both dating life and social situations. After
| the startup, employers consider the CEO the guy that was
| responsible for the success. Its a huge deal, most people
| have no clue how the whole thing works
| Aurornis wrote:
| > There is a non tangible level of status that comes with
| being CEO of a profitable startup.
|
| All of your comments in this thread assume success. Great
| if you can get it, but it's not guaranteed.
|
| > People dont know but it helps in both dating life and
| social situations.
|
| Much less than you think. Some people are impressed by
| it, but spend some time in a startup-heavy area everyone
| will see right through the "I'm a startup CEO" schtick
| for someone who has a $500K ARR B2B SaaS, or even just
| someone trying to fork off and do their own thing.
|
| While it is impressive to start and run a successful
| small-scale SaaS, it's far from guaranteed. Thinking it's
| a route to dating success is just weird.
| Aurornis wrote:
| > aware that "wanting to do engineering" probably is
| stopping you from financial freedom/a more interesting
| life.
|
| This only makes sense if you assume the startup will fail
| _and_ you ignore all of the high-paying engineering jobs
| out there.
|
| If financial freedom is the goal, the easier and far more
| reliable path is to pursue the well-trodden road to a job
| in Big Tech and put some minimal effort into the promotion
| process.
|
| The average startup founder does not walk away with
| financial freedom or even a functional company. The average
| outcome is that the startup doesn't work out and they pay
| the opportunity cost of having lost out on years of career
| income.
|
| Even the acqui-hires and small time acquisitions that
| happen in my local startup scene rarely leave the founders
| with more money than they could have earned at a regular
| 9-5 engineering or EM role.
|
| It's only a select few who get that coveted large exit that
| turns into financial freedom after 5-15 years of grinding.
| skeeter2020 wrote:
| Being the CTO at a company with a handful of people (where
| everyone likley has a C-title) doesn't absolve you from the
| responsibility of those tasks though. You really don't get to
| focus on "only" CTO roles until the company is much, much
| larger.
| herval wrote:
| Completely different skillsets. Lots of deeply technical
| startup CEOs kill their startups by not acknowledging that.
| mikert89 wrote:
| I really think society has built some weird narrative that if
| you did a technical undergrad, you arent fit to run a small
| startup. Ycombinator busts this myth constantly, and actually
| prefer technical founders.
| justapassenger wrote:
| Cynical view is that technical founders who don't know who
| business work are easier to manipulate into bad decisions
| for their business, as long as VC makes money.
| Aurornis wrote:
| There are a lot of defunct startups in my city that were
| started by engineers and CTOs. Some of them had good ideas and
| a few even had great execution of the product.
|
| They all failed at sales, scaling, retention, and generally
| running the business.
|
| I did work for one very successful company that was founded by
| an engineer. However, he was focused almost exclusively on non-
| engineering business functions from the start.
|
| If you want to be a CTO and do engineering things, don't assume
| founding your own company is the best way to get there.
| epicureanideal wrote:
| > They all failed at sales, scaling, retention, and generally
| running the business.
|
| This also applies to most non-technical, "business folks"-led
| businesses as well.
| Kholin wrote:
| I believe it depends on the industry your business is in. In
| many businesses, technology is only a small component, and
| other factors such as connections, sales, and marketing can be
| more important than the technology itself.
| sjtgraham wrote:
| This is of the classical genre of HN cynicism framed as advice
| that if you were to follow you're pretty much guaranteed to
| never go anywhere in life.
| mikert89 wrote:
| nah I have been in the venture scene in nyc for a while, have
| seen the same song and dance play out over and over
| palata wrote:
| IMHO it doesn't matter whether you are CEO, CTO, CFO,
| C-whatever-you-feel-like-O, as long as you are a founder.
|
| A startup is a kind of ponzi scheme benefitting the founders
| (and VCs).
|
| Successful founders will happily tell everyone and their dog
| how being a founder was _so much work_ , how they didn't go on
| holiday for a few years, how they worked long hours, etc. And
| mostly why they deserve to be rich now while none of their
| employees is. None of them will talk about how being one of the
| first employees was also _so much work_ , usually with a pretty
| bad salary and order of magnitudes fewer options than the
| founder.
|
| I always wonder how the founders can genuinely believe that
| they are actually worth thousands of me. I am pretty damn sure
| that with a thousand me, we produce more than the founders
| alone.
| mikert89 wrote:
| Maybe, but there are levels to the game. The CEO has legal
| rights to fire cofounders, often with the board on their
| side. Early stage this doesnt get exercised often. But when
| the CTO has ten million of equity to vest over two more
| years, questions get asked behind closed doors about whether
| they are worth that amount. Thats when the "professional CTO"
| is brought in. Its extremely common, and letting him vest
| that amount is coming out of the pocket of the CEO and the
| investors
| palata wrote:
| > The CEO has legal rights
|
| I don't think that anything in the law says that if your
| title is "CEO", then you can fire cofounders. I'm guessing
| it depends on the contract the cofounders sign in the
| beginning.
|
| > often with the board on their side
|
| I have seen the CTO convince the board to fire his
| cofounder who was more the CEO? Well I don't know if the
| titles were written in the contracts, they changed over the
| years. But the guy who got his cofounder fired went from
| calling himself CTO to calling himself co-CEO to getting
| his "buddy" fired.
| roadbuster wrote:
| > I am pretty damn sure that with a thousand me, we produce
| more than the founders alone
|
| Engineers generally never acknowledge the value of knowing
| _what_ to build, only whether something is built.
|
| As an engineer, I don't pretend to know or understand what
| the market wants or what people are willing to pay for.
| That's a problem I leave to business/product-oriented people.
| In exchange, they leave the building to me.
| palata wrote:
| > Engineers generally never acknowledge the value of
| knowing _what_ to build, only whether something is built.
|
| Nobody knows what to build, that's why VCs give money to
| many startups, _almost all of them_ bankrupting.
|
| The sole value of the founders is to be able to convince
| VCs for as long as they can. VCs generally have no clue
| about the technology, so it's about getting good at selling
| bullshit. Granted, I am not great at selling bullshit, so
| it doesn't make me a great founder.
|
| Now if we get back to knowing what to build, if you give me
| a thousand me, we can try a whole bunch of different ideas
| hoping that one works. This is what VCs do, and it works
| for them even though they have no clue either.
|
| No, a founder is never worth thousands of employees,
| period.
|
| And I'd like to note the asymmetry here: I am arguing that
| I am not thousands of times less valuable than them. I am
| not remotely saying that I am better.
| mbesto wrote:
| I would take a market-domain expert as CEO over a CTO any day
| of the week. Unless of course your product is to sell to other
| software providers.
| mooreds wrote:
| From 2024. Sorry, should have added that to the title when I
| submitted it.
|
| I personally loved the takeaways. They resonated with my startup
| experience, esp: "Not all business problems require technical
| solutions". I think as devs/engineers, we're in love with
| technical solutions, but they are not always the right choice.
| Other options include:
|
| * customer support
|
| * duct tape solutions with platforms like Zapier
|
| * saying "we are not going to solve that problem" and letting
| folks that need that solution go somewhere else
| javier2 wrote:
| > saying "we are not going to solve that problem" and letting
| folks that need that solution go somewhere else
|
| I know more technically inclined than not that can easily
| identity this situation. At least my CEOs have a tendency
| toward thinking we should pursue any path that likely leads to
| some income stream...
| mooreds wrote:
| That's fair. Depends on the CEO, PMF, and the bank account
| size.
|
| Sales driven growth is great until it isn't.
| Sammi wrote:
| You know the best selling pop psychology self help book The
| Subtle Art Of Not Giving A Fuck might actually be a good
| business book for people who haven't internalised that you
| have to say no to most things in order to be able to
| emphatically say yes to the actually important things.
| sgt wrote:
| I wonder what happened with this current company,
| helioscompanies.com ? Did it go under and is that why he's
| looking for a new role?
| globalise83 wrote:
| So how much money for 5 years of effort?
| cwbrandsma wrote:
| * How much stress? * How many hours?
| hn_throwaway_99 wrote:
| While I thought this was a pretty good read, I didn't really feel
| like it answered the question in the title: "was it worth it"?
|
| First, this post was from 2024, and as another commenter
| mentioned, it doesn't look like Helios Companies
| (www.helioscompanies.com) is a going concern anymore. That's not
| that surprising - the change in the interest rate and VC funding
| environment killed off lots of unprofitable fintechs that were
| originally funded in 2021 or earlier.
|
| I'm not saying money is the end all and be all, and this guy
| certainly got a lot out of it. But assuming this company is now
| defunct and he didn't get any substantial payday out of it, would
| he do it again knowing what he knows now? When you think about
| it, we all have relatively very limited time in our careers -
| while VCs can fund 100 different companies with the expectation
| that 95% will fail, workers don't have that luxury. Putting in 5+
| years of lots of late nights and blood, sweat and tears can be
| tough if the outcome isn't a winner.
|
| So I'm left wondering if the author feels like it was still worth
| it.
| hakunin wrote:
| I work with him at this company. We are still going, just don't
| have much of a public facing side, because most of the sales
| are direct b2b. We're working on showcasing more of what we do,
| but it hasn't been our top priority.
| hn_throwaway_99 wrote:
| Thanks very much for the correction. FWIW, the reason for my
| apparently faulty assumption is that when searching for your
| company online, the top result is the Crunchbase entry,
| https://www.crunchbase.com/organization/helios-companies, and
| it shows web (www.helioscompanies.com) and LinkedIn links
| that are both defunct.
|
| To be honest, I find it kind of bizarre that your company
| doesn't appear to have _any_ public web presence. I also
| worked at a B2B-only fintech very recently, and we still had
| a website. Heck, my neighborhood barbershop has a website. I
| know it sounds like I 'm knocking y'all (and maybe I am a
| little), but I'm honestly just curious. If I were a tech
| leader at a bank and got a direct sales call from a vendor
| and they said they didn't have a website, I'd just assume it
| was a scam. It must be working for your company so I'm very
| interested in how you haven't found the need to have a
| website in 2025. That I think would actually be a more
| interesting blog post!
| sarabande wrote:
| I'm curious about the simple, lightweight change management
| process listed in the article. Anyone have any tips on doing this
| well? I kind of hate the part of having to convince everyone of
| something "obviously better" :)
| aurelien_gasser wrote:
| The author states that a CTO should ask questions rather then
| give orders. What kind of questions?
| sandeepkd wrote:
| I was happily surprised to see the role and importance of QA
| being acknowledged.
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