5 ms·

Five years as a startup CTO: How, why, and was it worth it? (2024)

155 points by mooreds 1y ago

globalise83 1y ago
So how much money for 5 years of effort?
- cwbrandsma 1y ago
  * How much stress? * How many hours?
- gansbrest 1y ago
  I don't look at this like that, not any more at least. It's been great five years for me and my family, exactly what I was looking for before the transition from stable corporate world. I guess it depends a lot of personality and the type of work you enjoy. I thrive at early stages, where most things a built on common sense and you have enough power to shape things into something meaningful. These days I try to appreciate "the process" (day-to-day) over "results" (exits). You don't really have too much control of how things unfold in your life really, be blessed you are alive and kicking. Do I say money is not important? Of course not - it's very important, but in a challenging times you have to test your limits and re-assess your priorities (whether you like it or not...) It's easy to look at things in hindsight - the question is what is the alternative? 5 years of what?
laurent_du 1y ago
Good read, thank you. It feels nice to read something that was fully written by an actual human being.
- gansbrest 1y ago
  My pleasure.
thrown-0825-1 1y ago
where does the startup end and the small business begin?
- givemeethekeys 1y ago
  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 1y ago
    Solid definition. Being on the VC treadmill, and all of the “vibes” that come with that, is really what it boils down to.
    - collingreen 1y ago
      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 1y ago
    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 1y ago
      A "new business" or a "small enterprise"
  - dilyevsky 1y ago
    By your definition OpenAI and Databricks are startups.
Simon_O_Rourke 1y ago
I respect the honesty that went into that writing.
mikert89 1y ago
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 1y ago
  One perhaps (cynical) view is that CEOs with business background are basically just arbitraging between investors and product teams.
  - raincole 1y ago
    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 1y ago
    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 1y ago
    CTOs just arbitrate between dev teams and product teams.
    - mooreds 1y ago
      CPAs just arbitrage between cash flows and legal requirements.
mooreds 1y ago
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 1y ago
  > 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 1y ago
    That's fair. Depends on the CEO, PMF, and the bank account size. Sales driven growth is great until it isn't.
  - Sammi 1y ago
    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.
    - javier2 1y ago
      Even having worked on many such projects, it can be hard to tell if it was the correct choice. In any case, it came at great expense to the other projects we could have improved
sgt 1y ago
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?
- gansbrest 1y ago
  We are still going, but it's a bumpy road. One of main products got delayed by partnering financial institution, which sent us into money crunch mode. At the moment our engineering is ahead of our sales - which gave me some capacity to lift my head up and test my skills relevance against the market on the fractional/advisory capacity potentially turning into revenue stream with more control from my side. You know how it works for us with engineering minds - you always consider worst case scenarios and try to mitigate them before they become real problems. Based on my experience it typically works in cycles, where you need some sort of fresh blood every five or so years to re-kindle the spark and keep going.
hn_throwaway_99 1y ago
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 1y ago
  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 1y ago
    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 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 1y ago
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" :)
- gansbrest 1y ago
  It pretty much boils down to: - Jira Epics (describe the why from the business standpoint) - HQ meets two times a week to re-asses priority (drag up Epics up or down, or change priority) and monitor status - Two week sprints where engineering leads along go through epics - New sub-tickets created by engineering (including design) and assigned to specific people. - Once thing are getting done, they are move to QA test status. After testing it either goes back to engineering or to Release Approved status. - Engineer initiates and monitors the the release via CI/CD Jenkins pipeline. That's pretty much it on the high level, unless I'm forgetting something. One important note here - some time ago we made a decision to ignore "good ideas"/backog. We don't keep them in Jira until business is sure that we really need this particular functionality and ready to start building it right now. That was somewhat radical and took some time to get used to, but it allowed everyone to focus on what's important now vs nice to haves to keep people busy with things noone really needs. Overall there is no "generic" advice, everything is very org and stage specific. Common sense is the main guiding principle.
sandeepkd 1y ago
I was happily surprised to see the role and importance of QA being acknowledged.
aurelien_gasser 1y ago
The author states that a CTO should ask questions rather then give orders. What kind of questions?
- Terretta 1y ago
  One could do worse than asking for major decisions to come with a (ultralight, readme like) platform/product enhancement proposal (PEP). Then, in a group, probing together for 12 factor app or AWS well architected type principles as well as something like BSA security principles, gets you a very long way. The framework doesn't matter, just something to cause a beat of design, ops, and threat modeling and "rugged manifesto" thinking. https://ruggedsoftware.org https://ruggedsoftware.org
- gansbrest 1y ago
  All sorts of questions - "What's the best way to do X?", "How would it impact security?", "Why we need this?", "What happens if this fails?", "Remind me how this works?", "Am I thinking in the right direction?" Even more questions to the business / CEO ( Why this, why now ) "why", "how", "can we", "who can"? Just try to be humble in the world where nobody knows anything (including yourself)... :)
  - aurelien_gasser 1y ago
    Thanks!
iamcreasy 1y ago
> When I was younger I thought QA was the thing from the good “old days” that should be replaced with the automated tests suit. After accidentally hiring one great QA engineer I quickly changed my mind. Today I would say it’s one of the most important departments on my list. The amount of my time saved by QA team is insane. If the author is reading - can you elaborate on this?
- cialowicz 1y ago
  Not the author, but I'm a VP of Eng, and one of my sub-orgs is QA. Here's my take... Aside from writing end-to-end test automation, the best SDETs add value in many other ways. They triage bugs, use their deep product understanding (frequently the best on the team) to refine requirements and build test plans, coordinate bug-bashes and large scale releases, measure and report on quality metrics, and much more. All of this takes considerable load off other members of the team (SWEs, PMs, EMs, etc), allows the whole group to ship with much higher confidence, and increases the number of defects caught before making it to production. If you have an organization where end-to-end tests are easy to write and very quick to execute, then I think the need for QA folks is greatly reduced. In my experience, once there's enough complexity and scale to a product, it's basically impossible to have a rapid TDD loop with enough end-to-end coverage that allows devs to ship features with perfect confidence. Combine that with all the other "hats" QA folks wear, and I think it's is a role that pays dividends in product quality and the efficiency of others across the org.
- gansbrest 1y ago
  Pretty much what cialowicz said. At the end of the day someone needs to answer a simple question - "Is the product functional right now / after the last release?". If you don't have QA team you either rely on your product person to "give it a spin" or your engineering who are generally not very excited about clicking through the product multiple times (more often than not, they'll just leave it at the unit test phase and move on). In small orgs that product person could be your CEO or CTO, meaning this will give them an easy false-escape into "micro-management" mode (aka feeling productive by doing low priority tasks) vs forcing them to make strategic decisions or worse, they'll just block the entire pipeline. QA creates a natural quality gate looking at the product from the user's perspective, putting pressure at the engineering to deliver quality work and gathering leadership feedback at critical points only.

155 points by mooreds 1y ago

globalise83 1y ago

So how much money for 5 years of effort?

cwbrandsma 1y ago
* How much stress? * How many hours?
gansbrest 1y ago
I don't look at this like that, not any more at least. It's been great five years for me and my family, exactly what I was looking for before the transition from stable corporate world. I guess it depends a lot of personality and the type of work you enjoy. I thrive at early stages, where most things a built on common sense and you have enough power to shape things into something meaningful. These days I try to appreciate "the process" (day-to-day) over "results" (exits). You don't really have too much control of how things unfold in your life really, be blessed you are alive and kicking. Do I say money is not important? Of course not - it's very important, but in a challenging times you have to test your limits and re-assess your priorities (whether you like it or not...) It's easy to look at things in hindsight - the question is what is the alternative? 5 years of what?

laurent_du 1y ago

Good read, thank you. It feels nice to read something that was fully written by an actual human being.

gansbrest 1y ago
My pleasure.

thrown-0825-1 1y ago

where does the startup end and the small business begin?

givemeethekeys 1y ago
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 1y ago
  Solid definition. Being on the VC treadmill, and all of the “vibes” that come with that, is really what it boils down to.
  - collingreen 1y ago
    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 1y ago
  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 1y ago
    A "new business" or a "small enterprise"
- dilyevsky 1y ago
  By your definition OpenAI and Databricks are startups.

Simon_O_Rourke 1y ago

I respect the honesty that went into that writing.

mikert89 1y ago

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 1y ago
One perhaps (cynical) view is that CEOs with business background are basically just arbitraging between investors and product teams.
- raincole 1y ago
  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 1y ago
  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 1y ago
  CTOs just arbitrate between dev teams and product teams.
  - mooreds 1y ago
    CPAs just arbitrage between cash flows and legal requirements.

mooreds 1y ago

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 1y ago
> 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 1y ago
  That's fair. Depends on the CEO, PMF, and the bank account size. Sales driven growth is great until it isn't.
- Sammi 1y ago
  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.
  - javier2 1y ago
    Even having worked on many such projects, it can be hard to tell if it was the correct choice. In any case, it came at great expense to the other projects we could have improved

sgt 1y ago

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?

gansbrest 1y ago
We are still going, but it's a bumpy road. One of main products got delayed by partnering financial institution, which sent us into money crunch mode. At the moment our engineering is ahead of our sales - which gave me some capacity to lift my head up and test my skills relevance against the market on the fractional/advisory capacity potentially turning into revenue stream with more control from my side. You know how it works for us with engineering minds - you always consider worst case scenarios and try to mitigate them before they become real problems. Based on my experience it typically works in cycles, where you need some sort of fresh blood every five or so years to re-kindle the spark and keep going.

hn_throwaway_99 1y ago

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 1y ago
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 1y ago
  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 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 1y ago

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" :)

gansbrest 1y ago
It pretty much boils down to: - Jira Epics (describe the why from the business standpoint) - HQ meets two times a week to re-asses priority (drag up Epics up or down, or change priority) and monitor status - Two week sprints where engineering leads along go through epics - New sub-tickets created by engineering (including design) and assigned to specific people. - Once thing are getting done, they are move to QA test status. After testing it either goes back to engineering or to Release Approved status. - Engineer initiates and monitors the the release via CI/CD Jenkins pipeline. That's pretty much it on the high level, unless I'm forgetting something. One important note here - some time ago we made a decision to ignore "good ideas"/backog. We don't keep them in Jira until business is sure that we really need this particular functionality and ready to start building it right now. That was somewhat radical and took some time to get used to, but it allowed everyone to focus on what's important now vs nice to haves to keep people busy with things noone really needs. Overall there is no "generic" advice, everything is very org and stage specific. Common sense is the main guiding principle.

sandeepkd 1y ago

I was happily surprised to see the role and importance of QA being acknowledged.

aurelien_gasser 1y ago

The author states that a CTO should ask questions rather then give orders. What kind of questions?

Terretta 1y ago
One could do worse than asking for major decisions to come with a (ultralight, readme like) platform/product enhancement proposal (PEP). Then, in a group, probing together for 12 factor app or AWS well architected type principles as well as something like BSA security principles, gets you a very long way. The framework doesn't matter, just something to cause a beat of design, ops, and threat modeling and "rugged manifesto" thinking. https://ruggedsoftware.org https://ruggedsoftware.org
gansbrest 1y ago
All sorts of questions - "What's the best way to do X?", "How would it impact security?", "Why we need this?", "What happens if this fails?", "Remind me how this works?", "Am I thinking in the right direction?" Even more questions to the business / CEO ( Why this, why now ) "why", "how", "can we", "who can"? Just try to be humble in the world where nobody knows anything (including yourself)... :)
- aurelien_gasser 1y ago
  Thanks!

iamcreasy 1y ago

> When I was younger I thought QA was the thing from the good “old days” that should be replaced with the automated tests suit. After accidentally hiring one great QA engineer I quickly changed my mind. Today I would say it’s one of the most important departments on my list. The amount of my time saved by QA team is insane. If the author is reading - can you elaborate on this?

cialowicz 1y ago
Not the author, but I'm a VP of Eng, and one of my sub-orgs is QA. Here's my take... Aside from writing end-to-end test automation, the best SDETs add value in many other ways. They triage bugs, use their deep product understanding (frequently the best on the team) to refine requirements and build test plans, coordinate bug-bashes and large scale releases, measure and report on quality metrics, and much more. All of this takes considerable load off other members of the team (SWEs, PMs, EMs, etc), allows the whole group to ship with much higher confidence, and increases the number of defects caught before making it to production. If you have an organization where end-to-end tests are easy to write and very quick to execute, then I think the need for QA folks is greatly reduced. In my experience, once there's enough complexity and scale to a product, it's basically impossible to have a rapid TDD loop with enough end-to-end coverage that allows devs to ship features with perfect confidence. Combine that with all the other "hats" QA folks wear, and I think it's is a role that pays dividends in product quality and the efficiency of others across the org.
gansbrest 1y ago
Pretty much what cialowicz said. At the end of the day someone needs to answer a simple question - "Is the product functional right now / after the last release?". If you don't have QA team you either rely on your product person to "give it a spin" or your engineering who are generally not very excited about clicking through the product multiple times (more often than not, they'll just leave it at the unit test phase and move on). In small orgs that product person could be your CEO or CTO, meaning this will give them an easy false-escape into "micro-management" mode (aka feeling productive by doing low priority tasks) vs forcing them to make strategic decisions or worse, they'll just block the entire pipeline. QA creates a natural quality gate looking at the product from the user's perspective, putting pressure at the engineering to deliver quality work and gathering leadership feedback at critical points only.