[HN Gopher] Solo founder dilemma; CEO or CTO?
       ___________________________________________________________________
        
       Solo founder dilemma; CEO or CTO?
        
       Author : navaneethpk
       Score  : 202 points
       Date   : 2022-10-01 12:23 UTC (10 hours ago)
        
 (HTM) web link (nvnt.substack.com)
 (TXT) w3m dump (nvnt.substack.com)
        
       | mannyv wrote:
       | The important point here is that he got funding first, and it
       | sounds like at least half a million because he didn't talk about
       | begging angels for money or running out of runway.
       | 
       | He was able to hire someone fast.
       | 
       | You won't be this good/lucky.
       | 
       | In the traditional non-traditional startup you need a salesperson
       | and engineering to be free, because money. I suppose with dev
       | tools you can get rid of the salesperson because you're selling
       | tools to individuals? Which is more risk, but if it works then go
       | for it.
        
         | mannyv wrote:
         | FYI, people believe that dev tools don't make money, but
         | atlassian, pagerduty, zendesk, etc show that there is a market.
         | 
         | And most tools kind of suck.
        
           | mannyv wrote:
           | As a note, if you're in a startup you have no idea how far
           | ahead of most developers you are.
           | 
           | I keep forgetting that most developers throw their stuff over
           | the wall to IT and probably don't have a ci pipeline, do IaC,
           | , and probably don't deploy their own microservices or
           | understand the AWS stack. They probably have a 60% chance
           | they use source control instead of just copying folders and
           | changing the folder name. They don't do logging or security.
           | They scale by buying bigger instances. Docker is their
           | current tech boner instead of puppet.
           | 
           | Although pathetic, it is an opportunity.
        
             | freedomben wrote:
             | This is true, but most of those devs are in that situation
             | because they _want_ to be. They have less than zero
             | interest in taking on more. Often these people also value
             | job security /stability above advancement/novelty. Many of
             | them also do coding only while at work, and if they will
             | learn a new skill/tech it will be because their employer is
             | paying them to. Often this group will not follow any tech
             | news/blogs/anything and isn't even reachable.
             | 
             | In short it's a pretty tough group to market to.
             | 
             | To be clear, I'm not making a value judgment on this. If
             | those people are happy with life, that's great! That's
             | mostly the point IMHO.
        
         | navaneethpk wrote:
         | The part where I begged for funding is another story:
         | https://blog.tooljet.com/raising-vc-funding-for-open-source-...
         | 
         | Also the link to HN launch that helped a lot:
         | https://news.ycombinator.com/item?id=27421408
        
           | e1g wrote:
           | It's perhaps worth highlighting how much of an outlier your
           | experience was - having a social circle to intro investors,
           | inbound interest, and closing a $1.5M institutional seed
           | round within two weeks is a highly atypical trajectory for
           | solo founders with negligible traction.
        
             | navaneethpk wrote:
             | > having a social circle to intro investors
             | 
             | > with negligible traction
             | 
             | Disagreeing to these two points. The traction from HN &
             | ProductHunt launch was good that ToolJet got 1000+ stars on
             | GitHub in under 8 hours. The intros were made mostly by
             | great open-source founders who were totally strangers at
             | the time who discovered the project mostly from HN.
        
               | e1g wrote:
               | "GitHub stars", like "the number of downloads", is a weak
               | signal, rarely meaningful in traction talks unless
               | there's nothing more substantial to discuss. Traction
               | indicators for a low-code platform would be revenue,
               | number of paid users, number of apps deployed/updated
               | with ToolJet, number of different people using ToolJet
               | apps, the volume of data captured/processed per week,
               | etc.
        
               | nickstinemates wrote:
               | for 1.5m, any signal is important to build a story. all
               | of the things you list are important, but typically only
               | in later stages.
        
           | dnadler wrote:
           | FYI, the Tutorial link in the footer of the tooljet site
           | seems to be dead: https://docs.tooljet.com/docs/intro
        
             | navaneethpk wrote:
             | Thanks for noticing, fixing in some time.
        
       | asim wrote:
       | Be careful with advice like this. You don't know if the company
       | has yet succeeded. A lot of it is quite logical but at the same
       | time many things are an anomaly e.g the tool launched and closed
       | fundraising within a short period of time. That's not always how
       | it works out. Just because first commit to funding was 3 months
       | doesn't mean you'll experience the same thing. I struggled for 4
       | years alone on an OSS project before raising funding. Hiring
       | people, defining the product and executing was even harder. A
       | person's experience only tells you what worked or is working for
       | them or lessons they learned, it can't be cookie cutter fitted to
       | your own journey.
        
         | navaneethpk wrote:
         | Exactly the reason why I wrote the article in a way that it
         | just walks through the journey. The outcome of anything is a
         | function of the context & timing and hence whatever worked for
         | someone at a specific point of time to get to a specific stage
         | might not be relevant for everyone.
        
       | dadoge wrote:
       | Interesting...maybe we should normalize/de-stigmatize Dev tooling
       | companies to have a ceo who is an eng for the first ~ 3 yrs, and
       | then hiring a replacement (maybe even some early "vp of product
       | person")
       | 
       | There are probably so many good ideas that devs have, but they
       | don't have enough interest in being a ceo of a big unicorn
       | company, but understand the problem and can get a prototype up
       | with no red tape
        
         | Bilal_io wrote:
         | > Interesting...maybe we should normalize/de-stigmatize Dev
         | tooling companies to have a ceo who is an eng for the first ~ 3
         | yrs, and then hiring a replacement (maybe even some early "vp
         | of product person")
         | 
         | I wasn't aware there was any stigma there. Considering that
         | Gates, Dorsey and Zuckerberg were engineers who wrote code and
         | continued to be CEOs of their companies for very long.
        
       | qvrjuec wrote:
       | I love the curmudgeonly comment on the blog post:
       | 
       | > A "solo founder" should be too busy with real work to be
       | writing articles like this.
       | 
       | Amazing that they couldn't understand the article's marketing
       | value
        
         | didgetmaster wrote:
         | A solo founder has many things on their plate, but should never
         | pass up an opportunity to raise awareness for their product;
         | especially if it has progressed to what they think is MVP
         | status. Newsletters, blogs, and sites like HN are great places
         | to start 'getting the word out'.
        
         | superzamp wrote:
         | And probably clarity of thought value for the author as well,
         | I've found that writing is usually the best way to clear your
         | thoughts and identify potential remaining blind spots in
         | scenarios like this.
        
       | atdrummond wrote:
       | This was a great post that actually is undersold by the title.
       | Any aspiring solo founder should read this, as ToolJet's founder
       | has provided a great roadmap to getting to product market fit -
       | and understanding the trade offs and concessions a solo founder
       | must make. It absolutely matches my own experiences and expertly
       | lays out the growth plan for a software firm that's bootstrapping
       | and dogfooding off of a single person. Well done Navaneeth.
       | 
       | Will absolutely keep this in my personal list of articles for
       | friends and acquaintances looking to start their own firms.
        
         | navaneethpk wrote:
         | Glad that you found the article helpful :)
        
       | [deleted]
        
       | swyx wrote:
       | TIL about Tooljet from OP's post: https://www.tooljet.com/
       | 
       | between Retool, Budibase, Superblocks, and Tooljet, i'm confused
       | about how to choose. anyone have a good mental map of the low
       | code internal tools landscape?
        
       | justinzollars wrote:
       | Doesn't matter. You need product market fit and focus on your
       | customers.
        
       | blumomo wrote:
       | > if someone from the team steps up and adds a lot of value that
       | is expected from a co-founder, we will definitely promote the
       | person as a co-founder
       | 
       | How can someone get the title of a cofounder of an already (at
       | least) 2 years old company which is already set up an running? I
       | understand that traditionally this person then represents in
       | investor meetings, but why does it need to be a _founder_ title
       | of something that was founded long ago?
        
         | KptMarchewa wrote:
         | Elon Musk
        
         | dilyevsky wrote:
         | Some startups now retrofit co-founder title to employees as
         | recruiting tactic. Part of the overall title inflation trend I
         | presume. I've seen some extreme examples where there are dozens
         | of "co-founders" on the roster.
        
         | CalChris wrote:
         | Agreed. To me, a co-founder is anyone pre-money. Anyone post-
         | money is an employee.
        
           | konfusinomicon wrote:
           | I'm a co-founder, with the current CEO and one other guy who
           | retired, and have always been on the engineering side of the
           | business. at first, the engineering department was me, and
           | support. I was super green back then and was pretty lucky to
           | be at the right place at the right time and as such, the
           | company grew far faster than myself. I have many superiors
           | now, which is cool with me as I've continued learning and
           | growing professionally by observing them. going from me and 2
           | other guys to late series C has been a priceless experience,
           | and it's nice to have the title. but oh my, the spam email
           | and phone calls I get from having it on my LinkedIn profile
           | is beyond annoying. many assumptions are made by companies
           | advertising to co-founders, mainly that im C level and
           | involved in sales. I struggle to calculate the total cost of
           | all the sales guy time spent targeting me but I can safely
           | say atleast a low end Lamborghini could have been procured if
           | it was all pooled together.
        
         | matchagaucho wrote:
         | "Founder" is not a title you can add casually under US law.
         | 
         | It's determined at the time of incorporation and stock
         | issuance. QSBS, and other legal structures, do not allow
         | transferability of "Founder" to follow-on Investors and
         | employees.
        
           | Ozzie_osman wrote:
           | I don't think QSBS has anything to do with founder titles
           | specifically, but I'd love to be corrected. Anyone who with
           | stock that is QSBS eligible gets the exemption, whether they
           | are a founder, investor, employee, etc, and it's more about
           | the eligibility (ie you paid for the stock, you didn't
           | acquire it on a secondary transaction, the business was <50M,
           | etc). Whether your title is founder or not doesn't really
           | matter.
        
           | navaneethpk wrote:
           | I might be wrong here but "Founder" is just a title and it
           | has nothing to do with law or investors. Adding another
           | "Director"/"Officer" requires some paperwork though.
        
             | bfung wrote:
             | You're correct. I'm not a lawyer, but went through doing
             | own startup:
             | 
             | It varies in incorporation requirements by state, but most
             | only require 2 titles positions - a President and a
             | Treasurer (the "Officers")
             | 
             | Adding or removing a Director, as in "Board of Directors",
             | requires amendment to the Corporation's bylaws, which
             | should state how many seats there are.
             | 
             | Aside from those titles/roles, all the "C" prefixed titles
             | are made up. Usually, one C level person is the President,
             | another the treasurer. Co-founders are usually on the board
             | of directors. Many times, a single person can be on the
             | board, a co-founder, and ceo.
        
       | badrabbit wrote:
       | Do you have to give yourself titles everyone else is using? If I
       | start a company I would rather have "Captain" or "Masterchief" or
       | perhaps just keep the C from CEO and be just a "Chief".
        
         | pitched wrote:
         | It's helpful to align titles with the rest of the industry so
         | that everyone outside of your small group knows what role you
         | play without a long explanation. Custom or non-standard titles
         | is like mixing code styles in the same file. So much fun when
         | you're doing it but such a huge pain when the next person comes
         | in.
        
       | shaburn wrote:
       | So early on CEO is going to be selling customers and employees
       | 80+% of the time but every Founder will need to. So why not
       | delegate that to someone much better than you when you truly need
       | the extra help. If you are not a killer technical founder, than
       | what chance do you have in the market, as you've already signaled
       | you're not the best sales person by not defaulting to the CEO
       | role. Thus I'd argue you have little choice.
        
       | mgaunard wrote:
       | You should look for both a CTO and a COO.
       | 
       | Whatever you cannot find a person for, you do yourself.
        
       | escapecharacter wrote:
       | C1O
        
       | intelVISA wrote:
       | #1 is too true, it's a nightmare to try find someone suitable &
       | non-technical to augment any dev tooling (or similar) venture IME
       | 
       | How did you handle the VC raise or were you entirely
       | bootstrapped?
        
         | navaneethpk wrote:
         | I've written another article that explains how we raised seed
         | round here: https://blog.tooljet.com/raising-vc-funding-for-
         | open-source-...
        
           | xwowsersx wrote:
           | Good post, very helpful. So it sounds a good approach, or at
           | least one, if you can't just quit your job and go full-time
           | without some funding is to launch the project/product and go
           | straight for a seed round which then gives you the resources
           | you need to go full-time. Great to hear this is a plan that
           | can work, assuming the project gets enough love.
        
           | intelVISA wrote:
           | Thanks :) grats on the succesful launch
        
       | lokimedes wrote:
       | Does anyone have similar recommendations regarding sales,
       | marketing and other business critical functions? As someone
       | contemplating the hard roads of B2B and non-SaaS , I feel a lack
       | of basic advice on going from idea to revenue.
        
         | dahart wrote:
         | That's a legit & hard question, and my startup experience is in
         | consumer SaaS products, but my first thought is: are sales &
         | marketing truly critical to your bootstrapping process, if
         | you're going B2B? I ask just because I've heard a lot of B2B,
         | especially for young companies, happens via referral.
         | 
         | Like the article, one way is to do it yourself until you grow
         | and can hire someone into the positions you need. Do you have 1
         | customer ready to go who will fund solo development? Do you
         | have a team who will jump in if you land a seed round, or will
         | you start building solo? This all depends a lot on your funding
         | & runway situation.
        
       | moralestapia wrote:
       | >do not nitpick - every fight is not worth picking
       | 
       | This is quite valuable. Great article Navaneeth, thanks for
       | sharing.
        
       | rubenfiszel wrote:
       | Just want to add, I followed pretty much the same path with
       | Windmill [1], which is also in the developer tool space, and also
       | open-source. Built everything solo for 5 months. I thought it
       | would be impossible to get into YC, it is not and I was fortunate
       | enough to join YC on the latest batch, on my first try [2].
       | 
       | Getting into YC changed the course of the company, increased many
       | orders of magnitude my ambition and made fundraising much easier.
       | Most importantly, even though I worked in tech in the bay many
       | moons ago, at the time I was very isolated in Paris and thought I
       | understood the startup game but I did not really. Being part of a
       | cohort like YC with like-minded amazing peers, truly felt like I
       | was able to go up to speed on many subjects that would have been
       | out of reach for a solo founder.
       | 
       | If you are a solo technical founder and considering applying to
       | YC, reach out to me, I am more than happy to help.
       | 
       | [1]: https://windmill.dev
       | 
       | [2]: https://news.ycombinator.com/item?id=31272793
        
         | malux85 wrote:
         | Congrats on getting into YC!
         | 
         | I'm the Solo Founder of https://atomictessellator.com, also
         | applied to YC this batch
         | 
         | (Actively looking for co-founder), wish me luck!
        
         | mgaunard wrote:
         | There are a lot of tech incubators in the Paris area.
        
           | rubenfiszel wrote:
           | And VCs, but as much as I'd like it to not be the case, the
           | US and the bay area in particular play at another level. The
           | french ecosystem is getting really good at some forms of deep
           | tech, but developer tools is not one of them, yet. The
           | current government and station F have done wonders, we were 8
           | french startups at YC this year, the most populous of any
           | other EU countries. Things are starting to change in the
           | right direction and french engineers don't lack the drive and
           | talent.
           | 
           | On the other hand, French people/VCs will wonder what can go
           | wrong whereas in the US they look at what can go right. There
           | are enough hurdles to face when trying to build a global tech
           | companies as a solo founder and it can definitely make a
           | difference.
        
           | jokethrowaway wrote:
           | Sure but they'll bring you some croissants and half a desk
           | for 3 months for your seed round.
           | 
           | If you're a startup in Europe you can forget about the scale
           | you can experience in the US and you should dedicate someone
           | in your team to apply to every European grant out there to
           | survive.
        
         | xwowsersx wrote:
         | Very cool, thanks for sharing. Windmill looks well done. I've
         | got a few ideas I'm mulling over in the dev tools space and
         | would consider going the solo technical founder. Will
         | definitely reach out for some advice when the time comes. Out
         | of curiosity, any downsides to use the .dev tld?
        
           | rubenfiszel wrote:
           | I would prefer the windmill.com domain but a cool windmill
           | museum has it. I have not seen any downsides except Google
           | (who owns the .tld) kept refusing to approve our oauth
           | because the approval team was convinced that .dev could only
           | be for testing.
        
             | xwowsersx wrote:
             | Good to know. It works well for products like yours.
        
         | bcjordan wrote:
         | Off-topic but have to say OSS Pipedream is something I've
         | wanted to see for so long. Definitely checking that out!
        
           | rubenfiszel wrote:
           | Thanks! and let us know what you think, we are still rapidly
           | iterating (to the point where the landing page and video is
           | quite obsolete)
        
             | RcrdBrt wrote:
             | Hi Ruben!
             | 
             | Great to see Windmill advancements
        
       | kukabynd wrote:
       | This is an excellent and pragmatic way of looking at scaling team
       | as an engineer. The defragmentation comparison really
       | demonstrates this clearly, thank you for sharing this.
        
       | fuzzieozzie wrote:
       | [unpopular opinion] If you struggle with this decision then you
       | have other problems.
       | 
       | There is no time for Worrying about titles -- I was "Jack of All
       | Trades" for 4 years at the company I co-founded before I became
       | CEO!
        
         | Etheryte wrote:
         | A perhaps not so unpopular opinion is that it would be better
         | to read the article before you comment on it. Despite the
         | title, the article is not about mulling over what title to call
         | yourself.
        
         | cercatrova wrote:
         | Perhaps you should read the article before deciding to comment.
        
       | didgetmaster wrote:
       | It seems to me that every great tech company needs two things to
       | get off the ground. A product that actually works well and
       | execution on the business side. Few people have the skills to do
       | both of these things well. Apple got started with the two Steves
       | (Jobs and Wozniak). One built the first couple of computer
       | designs. The other was a sales and marketing genius.
       | 
       | If you have a product that is possible to launch in just a couple
       | months, then you might be able to get by as this guy did. If your
       | product is much more complicated and takes several years for a
       | solo developer to build, then you have to pick the CEO or CTO
       | role and go with it.
       | 
       | My own project has been a work in progress for several years now.
       | I can build it, but my sales and marketing talents are quite
       | lacking. It is a new kind of data management system and it can be
       | really tough to raise awareness and get people to try it out.
        
         | NetOpWibby wrote:
         | Link to your project (if it has a site)?
        
           | didgetmaster wrote:
           | https://www.Didgets.com Here is a short demo video:
           | https://www.youtube.com/watch?v=2ScBd-71OLQ
        
             | NetOpWibby wrote:
             | Neat! I see a market for this; devs who have inherited a
             | mess of a project and want a low-stress way of managing
             | data.
        
         | enraged_camel wrote:
         | People always describe Steve Jobs as a "sales and marketing"
         | person but IMO that grossly undersells his value. He was also
         | an amazing product visionary, and could bridge the gap between
         | sales/marketing and technical.
        
           | didgetmaster wrote:
           | Yeah. That too!
        
         | navaneethpk wrote:
         | Agreed.
         | 
         | >I can build it, but my sales and marketing talents are quite
         | lacking.
         | 
         | Can relate to this. What worked well in the case of ToolJet is
         | that the product did not require marketing efforts to get the
         | initial traction since the project is open-source.
        
         | Ozzie_osman wrote:
         | You need a third thing, which is the ability to "sell" what
         | you're doing to some combination of customers/users, investors,
         | and people you want to hire.
        
           | didgetmaster wrote:
           | Absolutely. I have had a few hundred people tell me that they
           | think the technology is amazing and can't believe how fast it
           | is; but so far only a few paying customers and no investors
           | (other than myself) yet. Bootstrapping is hard.
        
         | matchagaucho wrote:
         | Developers selling to Developers is the exception.
         | 
         | There are many talented Sales/Marketing people. But few who can
         | effectively target Developers.
         | 
         | The Authors path of bootstrapping via open source is a known
         | tactic/strategy.
         | 
         | Ultimately growth will require directly approaching other
         | Developers with a commercial proposal.
        
           | freedomben wrote:
           | The importance of this cannot be overstated. Developers are
           | extremely difficult to market to if you're not a developer
           | yourself. It can be done, but very few sales/marketing people
           | will be successful unless they have much experience in it.
           | The reason why is that developers break all the rules you
           | learn in marketing departments and schools. What works with
           | normal people will not just be ineffective on devs but will
           | actively repel them.
        
             | didgetmaster wrote:
             | As a developer, I take exception to your insinuation that
             | developers are not 'normal' people. :)
        
         | hellolemon wrote:
         | Getting products to market cost a lot of money. It's hard to do
         | organically unless you have your niche well defined.
        
       | awesomegoat_com wrote:
       | CEO and CTO sounds like too much work.
       | 
       | I call myself head of research in my own bootstrapped start-up.
       | :-)
        
         | remexre wrote:
         | Yep, the founder of my company is still the "Vice President of
         | Research"!
        
       | bitL wrote:
       | CEO all the time. CTO only if you absolutely trust your CEO. But
       | as the saying goes, the optimal number of co-founders is an odd
       | number and three is too much.
        
       | darthrupert wrote:
       | Since a solo founder is a dreamer role, CMPO: Chief Metaphysical
       | Officer.
        
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