My startup failed, then I found out I was unemployable
In this postmortem from 2021, @dave_sullivan candidly breaks down the dissolution of their startup, examining the fatal assumptions, misallocated resources, and market dynamics that led to its shutdown.
Core Principles for Independent Builders:
Early signals were often rationalized away instead of prompting an immediate pivot in distribution or pricing.
The psychological toll of running out of capital compounds operational friction in a solo or small team setup.
Key Antidote: Validate paying willingness before committing months to building sophisticated product features.
Community Debate Themes:
Community discussions on HN centered on identifying product-market fit early, avoiding vanity metrics, and the emotional recovery process after shutting down.
CATEGORY Postmortems & Failures →
HISTORICAL ERA Pandemic Bubble (2020–2022)
COMMUNITY SCORE ★ 460 points
TOTAL DISCUSSIONS 595 comments
Wow this could be me!
Almost the same experience, except without the obsessive marriage to poor products and I actually did learn how to pass those l33t code and behavioral interviews.
Basically I left the software career and did a tech startup that essentially failed but made me an okay amount of money (yay no dilutive capital), tried to leverage my newly awesome network to get a job and also went to through the recruiter path. Once I started getting good at the interviews and solving them above the average time, I still wasn't getting hired. Like this guy, I did this with about 20 different companies, although when I look at forums people are doing this with way more companies and way more time studying and practicing. So that's kind of a pathetic waste of resources happening industry wide.
All the big tech companies interview me for an L5 or equivalent. All the non-big tech companies just didn't want to pay me more than $180,000. Which eventually turned into a big deal because some disgruntled ex-hiring managers would retroactively contact me and tell me they got overruled and that my skillset and experience should have landed me roles at 180-220k. Improbable and a completely separate discussion, (am I getting overriden by a particular VC board member? nah it doesn't go that deep), any way I honestly just have better things to do. I had begun to be willing to take a much lower more relatable salary or compensation package, but then I found another lucrative project to do (with no dilutive capital yay) and that's been great. Crypto market picked up again too, great way to make money. It is still strange that the private sector doesn't accurately value this skillset yet (employed "blockchain jobs" pay low with startups paying the highest and midsize companies that are dabbling in blockchain are treating it like an intern play thing. all while contract and solo work pays or earns several multiples above market.)
Yes, another similarity is our observation about San Francisco and the Bay Area being just a working class town with high salaries. People there think they are special because the salaries are high. But it's really just like factories, like the article mentioned. The idea that they're special allows for all kinds of cultish abuse.
Use this thread as a collection of anecdotes to get a view of the reality, as soon as I was willing to interview for a role that would pay between $110,000-$135,000 the entire experience was completely different and better. Despite thinking "ah I'm an unemployable founder" or "ah maybe I'm older and I hit the wall I read about" or "ah my google results must not be good" or something, the experience at the lower salary (but high to that company in a different city) matched my positive interview and onboarding experiences earlier in my career. I did not accept as I was on to other things. So really all I have left for comparison purposes is the compensation: industry wide, people just don't want to pay me above a certain amount. They look at me and don't say yes. So there is a glass ceiling for me in that field, not the first person to draw that conclusion. Travel and doing my own thing is more fulfilling - I have a lot of lucrative software projects to continue rolling out - although the earnings are mostly similar to FAANG L5's with vesting stock price appreciation, its not as risk free as just showing up to a FAANG job as I meet many of them in my travels (over the last 6 months any way) and get a feel for their obligations or lack thereof, hope the industry gets better!
I enjoyed the blog post. It didn't break new ground, but it is still useful and a little therapeutic for me to read these posts.
I have made it a personal goal to have a career in the tech industry that doesn't require taking technical exam interviews. It's something I understand I need to work on - to earn, really, it's not something that just happens. My approach is to do this by consulting, speaking, teaching workshops, doing projects, and eventually building a network, mainly through contacts with non-technical people who value my assistance. It actually has been working.
This approach has, however, required taking a hard pass on what have turned out to be very good career opportunities. But since I very rarely pass a technical exam interview, I'm not really sure what I've lost.
Another factor - I was a math major and did a grad degree in operations research, so while I've written lots and lots of code and wouldn't really call myself "self-taught", I'm not really a great match for SE roles. Yes, I did code for graphs and trees, factoring primes, solving diff eq's and optimization problems, and so forth, but this was within the context of math classes, not CS. So I never took any formal CS beyond the intro in college. Over time, I realized that's not a coincidence, I actually was't really interested in code per so, I was interested in what questions I can answer with code.
One thing I mention here on HN - I can absolutely create and search a binary tree, DFS and BFS. I've been able to implement merge sort and recursively print all permutations of a string or set. I believe the claim that a tech interviews are used to filter out those who "just can't code" is a myth. The questions I get in later rounds of tech interviews are far more elaborate than this (for example: find all matching subtrees in a binary tree at the whiteboard, in 45 minutes). Here's the thing - I actually have used trees extensively in my work (I needed to find the shortest path to passing a series of interrelated tests where various groupings were adequate). I looked it up, learned it, coded in it... but eventually it left short term memory. Had I taken a tech interview test on exactly the same topic aa year later, I would surely have failed. I just don't walk around with this all loaded up in my head, and I feel that I've re-loaded it for an interview for the last time (I would happily reload it for a real project).
And I'll sign off with my usual: companies are free to filter out candidates based on very intricate technical tests, but I have zero sympathy when they complain about a shortage of good candidates. And this becomes sinister when they claim that this shortage means that they should be empowered to bestow limited residency rights on someone where they control how the person interviews, what the person works on, where the person lives and works, and when the person shows up at the office.
Some of the views you will find below are conflicting. No need to call me a hypocrite, I am familiar with my dissonance on this matter.
I'm a self-taught engineer and I work in the SV and SV-adjacent scenes. People who are self-taught genuinely have a hard time at the beginning and middle stages of their careers, to the extent that it can break you. If you try to explain this to any CE or CS graduate it's like they lift their magical empathy goggles and provide a full stream of excuses for the current paradigm that excludes both good and bad talent.
Where I'm about to be a hypocrite is now. My unpopular opinion is that gatekeeping is just fine, but it's all in the details. If you are gatekeeping based on knowledge that is commonly acquired in college, then you are gatekeeping for education and by proxy gatekeeping for status. If your interview process involves binary search but you don't do binary search by hand during your day to day, you are gatekeeping for education and by proxy status. That said, I'm a curious person and I know how to implement some recursive binary search because fiddling with sorted numbers can be fun when I'm inebriated and bored. It also shows some uncommon competency, so it is a great gatekeeping tool for curiosity and quality. The question I began asking myself is how I balance the equation. If a non-college/CS/CE educated person struggles with more fundamental math, then the trick is to introduce tasks which also disqualify them in higher numbers. For this, I found systems design to be an incredible tool, and one that non-college/CS/CE people tend to excel at. I'm sure there's more. At the end of the day, my team has a high bar for quality needs, but balancing the equation was important so that people like me would still get through the pipeline.
This resonates with me, I lost my job just before my forties. It was in a pretty specialized field using a proprietary language not known outside of it. I was also in a non native country. While I could have probably found another job in the same field using the same skills, it would most definitely involve moving to another country and I was really settled where I was. I was also having visions of slowly becoming too specialized and ending up in a basement somewhere looking after a legacy system.
I'd been working on an OSX app as a side project for fun and decided to develop that, if only to add an other skill while I still looked for another job. After a little interest this developed into an iOS app and that started selling a few units a week, but nowhere near enough to pay the bills. (It still brings me in beer money every month)
All the time I was looking for another job, slowly running out of money, this was for 4 years. I'm not university trained, had worked with this language no knew about for near twenty years, now over 40, in a country where I wasn't completely fluent in the language and getting interviews was hard, really hard. Of the interviews I did get, one interviewer told me the app I had written wasn't technically possible, another told me I'd never keep up with younger kids.
I had just about run out of money when I finally landed an interview at a company looking to develop an iOS app and also in a similar field to what I worked in before, luckily they needed someone right away and I aced the interview. I've been there 3 years now maing a great impact on their existing app, and now after developing and proposing a new app to the company, I now work on that. I feel my employment prospects are in a much better place for the future, with a successful app under my belt in an environment people actually know about.
It was tough though, just sorting out the mess I had got into with surviving on my last pennies and getting into a pretty bad state psychologically is something I'm still dealing with.
Sure, that’s a little bit understandable if the problem came at you out of nowhere, but...that basic algorithms questions are common technical screens is hardly hidden knowledge. Abd that aside, even without having studied it specifically, reversing a binary tree isn’t, as problem solving challenges a developer might face, a particularly challenging one.
Examples here would be useful to understand the complaint; I mean, since you say you were actively looking for data scientist vacancies, I would assume that both understanding and identifying needed clarification on statistics word problems ought to be in your wheelhouse.
While you may not usually write queries by hand, using an ORM doesn’t prevent you from needing to understand complex SQL for complicated queries, and, I mean, I don’t known what position this was an interview for, but if you aren’t the person dictating tech stack decisions (as presumably you were as a founder), you may not have the luxury of avoiding get your hands dirty with SQL, so its not an unreasonable thing to test.
So why weren’t you either:
(1) Continuing to work as a consultant, either independently or in a consultancy?
(2) Applying for the types of b2b sales, or other business-oriented positions for which starting a company or independent consultancy experience would be relevant?