I'm a non-technical CEO of 20M startup that wants to learn

I feel like you should be learning from your CTO and other engineers. No-one reasonable expects you to know the technical side in detail, and as the CEO, it’s perfectly reasonable for you to be asking your technical people questions like “what are the 3 most important things we need to think about x”. In fact, ideally when you hire engineers, as well as having your engineers confirm their technical knowledge, you should be picking one or two random things on the job description your company posted and asking them to brief you on it. That way you hopefully get engineers who are both technically able and able to communicate to the non-technical side of the business.

Get in touch if you want to chat.

Start by taking to your CTO to understand the basic architecture of your product and tech stack, so you know what tech you are using for frontend, backend, db, etc.

Then pick one and take a look at some beginner tutorials for that technology. See what it would take to build a “Hello, world” type product.

First: I am technical, and there are still technical articles (or conversations) that leave me in the dust. I was reading about advanced memory management techniques the other day and it was very apparent I was out of my depth.

So it's a spectrum, not a switch. You will never understand all of them. But you can increase the proportion.

My suggestion would be to just give yourself permission to play around. Look something up on wikipedia---when it gets boring or hard, stop. Install python on your personal machine. Now install another version. Now you hate pip, and you too are a Real Engineer.

Trick is avoiding the temptation to work hard. "Courageous play" is the phrase to keep in mind.

I created a remote SaaS business for the online coaching space 5 years ago; they were probably hundreds of JavaScript frameworks at the time and most of them are now deprecated.

It's a shame I decided to carefully digest each piece of content about these technologies: I read HN posts, watched Youtube videos, signed up for Coursera Moocs. I eventually made late and bad decisions on tech decisions and this broke our codebase.

One day I searched on Google something and discovered its Knowledge graph feature which links content together. This inspired me to draw mindmaps and cheatsheets on paper of the technological landscape to get a global grasp of it[0]. Each time I read an article or talk with a dev, I can now make the link with the micro and macro ecosystem.[1]

I refer to these mindmaps daily to learn new things (even beyond tech). To push limits, I make a browser extension to smartly organize all my bookmarks.

[0] You can use this site as a boilerplate for your mindmaps and link your Google Searches and what you read to it: https://roadmap.sh/, they have a Youtube channel: https://www.youtube.com/c/theroadmap/videos. You might find Fireship useful too (it popularize many tech topics): https://www.youtube.com/c/AngularFirebase/videos

[1] New tools called "second brains" can be used as supports (Notion, RoamResearch). However I prefer using paper or making my own tool.

I hope this helps! (content overloading is such a problem in education)

The primary question is "why"? Where is your company struggling because you aren't technical?

In my mind (as a technical founder), the things a CEO needs to know are at the conceptual / theoretical level rather than the implementation level. I've seen businesses fail because the CEO silos the technical side of house from the "business" side and then doesn't have enough technical knowledge to parse suggestions that aren't aligned with business goals. That problem is better solved by eliminating the silos and aligning incentives rather than gaining technical knowledge, in my opinion.

There is no an easy answer to gaining technical familiarity. If there were then everyone would be experts. You are going to need an investment of effort.

Understand some basic concepts. Technical subjects can span many domains:

* Accessibility

* Transmission

* Security

* Usability

* Performance

* Data Storage/Analysis

* Legal

* Enterprise Architecture

Understand that various technical domains have competing concerns and goals. Learn about the basics of the domains that are important to you and your business. For example it’s my professional experience as a software developer and former security analyst that most software developers bring a net negative in terms security knowledge/applicability because they have no formal knowledge of the basics. They commonly have unverified assumptions and build upon that faulty premise.

Secondly, communicating anything technical well is a matter of good writing on top of domain knowledge. That doesn’t mean the author should slow down and allow the reader to pause for breadth if they have no formal knowledge of the domain. That said, get some basic domain knowledge and then just jump in. Reading technical publications gets easier as the domain knowledge becomes more familiar, as you become emerged in the subject.

Third, build personal relationships with knowledgeable people. The goal here is to build trust and confidence in advisors. This is better if the trusted sources are people that don’t work for you so that they are more open to tell you things that you don’t want to hear, things that may conflict with your business interests. Trusted confidants aren’t there to reenforce what you can learn independently, but rather to help you make more informed decisions by challenging your assumptions and guiding your future.

Thank you all. To synthesize: - learn what I want to learn, probably by speaking with team to prioritize - leverage team + online to structure learning, starting high-level, 'courageous play' - periodically look for current weaknesses, or future strengths, from [lack of] operational integration within company (likely a benefit of technical learnings)

Youtube has a lot of great content on almost anything but the stuff discussed here is as varied as there are languages and frameworks. Youd have to narrow down your search to specific topics or just general knowledge of computing which will take years at best. I suppose you are busy with non technical stuff so I doubt you'd find the deep dives into the innerworkings of kubernetes interesting.

Yes, there is that gap. My gut feeling is that it is as genetic as other components of intelligence, so I'd say don't worry about it too much.

Yes, absolutely you can learn. A lot. But I doubt you can cross the schism. I know it's an unpopular opinion.

I am on the tech side of the "schism". Anecdata is from observing how my and others' kids approached tech stuff.

I am afraid any answer I give will be too generic and not too useful without knowing more about you, and what you would find more useful. Please feel free to ping me at my_username@gmail and I will be happy to mentor you through the process.

You can always use the phrase "explain it to me like I'm 8".

That usually gets a fairly jargon free answer. I've see those requests and replied to them, as have others.

Also: I'll answer anything I can if you email me. I check it every day or so.

Just to be clear your startup has $20m in revenue or VC? Either way sounds like you're doing a pretty great job as CEO and your CTO knows what they are doing too. Good job.