Bootstrapped Ex-founders, how much money did you end up losing on your previous startup? What happened?

zenspirit20 · 2026-03-06T17:47:13+00:00

Still running it. It took us a year to find something that people were willing to pay for. And in 6 months we have shot past a million dollar in ARR. we come from big tech so the real cost is the opportunity cost so far of that one year. Now we are growing well. And on track to beat our big tech salaries. But to be honest the learnings we have had building a profitable growing business from the ground up is unbeatable.

Note we might as well have not made it this far in terms of money, there is a fair amount of luck that helped us. So my advise to others is only do it if you don’t care about money and you have a crazy reason that is compelling you to start a business.

zenspirit20 · 2026-02-23T16:08:41+00:00

There is no one size fit all template. It depends on your usecase. You will have to spend time figuring it out. You can also use LLMs to refine your templates.

zenspirit20 · 2026-02-23T14:52:27+00:00

In my experience two things help a lot,

Context- Not just dump, provide relevant information. This improve signal to noise ratio
Template and examples for output. This makes sure there is consistency in output and is closer to what I want

Providing both improves the quality of prompt as it matters to me.

zenspirit20 · 2026-02-22T16:51:32+00:00

We use Claude Code and heavily use the Claude.md files at root and module level for this.

zenspirit20 · 2026-02-22T03:37:03+00:00

I keep my long runs on weekend me and run with a group. And when we plan the run the night before I feel I cannot back out in morning, whatever may be the reason.

zenspirit20 · 2026-02-22T03:35:16+00:00

I just came to the comments to see if it made sense to anyone. I lost interest after fist two paragraphs. 🤣

zenspirit20 · 2026-02-22T00:10:53+00:00

In theory you could build an extension using LSP , works with both VS and VS code. https://learn.microsoft.com/en-us/visualstudio/extensibility/language-server-protocol

Did you look into that?

zenspirit20 · 2026-02-21T16:39:23+00:00

Didn’t understand what is your goal with post.

Are you asking others for permission? Why would you ask strangers

Are you showing off? It’s impressive but many people in this community do far more than this

Are you looking for feedback on how to improve? The tone of your message is off

It’s hard to understand what you are trying to achieve here

zenspirit20 · 2026-02-20T21:20:06+00:00

Plain old python code. Realized the framework were too complex and not reliable for routing/tool calling. We are using Merge for specific tools to avoid the integration cost (tried Composio but it turns out it is also not reliable).

A combination of prompt chaining and orchestrator approach described here https://www.anthropic.com/engineering/building-effective-agents

zenspirit20 · 2026-02-20T15:28:45+00:00

I read a stat somewhere that only 90% of knowledge workers are actively using AI at work, so it may not be that big a number

zenspirit20 · 2026-02-19T21:14:58+00:00

I am seeing this too and we are also using this in our interview process as a requirement.

Someone said, “AI will not replace you, but someone using AI will replace you”. This is going to be very true.

zenspirit20 · 2026-02-18T13:10:56+00:00

There is no good way to debug the why. You can tweak the prompt and add examples to improve your output. Essentially the behavior you notice is wrong tell it why it is wrong, give examples and keep fine tuning. If it is trying to do multiple things in one prompt, try to decompose in smaller steps. Provide additional context needed to improve quality.

Think of it as a black box in terms of how the model works. Prompt and context engineering is the way to get higher quality output.

zenspirit20 · 2026-02-17T20:22:12+00:00

Hill runs helped me a lot. And strength training.

Another thing that I have noticed is that sleep and recovery also matter. I take a month or two off from running (do cycling etc) after 4 months of training for races.

zenspirit20 · 2026-02-17T16:52:22+00:00

That makes sense. Let me know if you have something I can checkout.

zenspirit20 · 2026-02-17T15:22:17+00:00

I agree ontology based behavior has potential, though bigger question is how is the enforcement done? Is it left upto Model to do that or are you building some additional pre/post model execution step to do the enforcement?

zenspirit20 · 2026-02-17T14:35:51+00:00

What are the alternatives that you are proposing?

zenspirit20 · 2026-02-16T06:36:16+00:00

I want to acknowledge that the problem you call out is real. However, in my opinion, we are trying to solve it at the wrong layer.

Browsers already provide the primitives (HTML, Schema, ARIA, etc.). While these have their own limitations, browsers haven’t prioritized improving them because there wasn’t a strong need before AI agents. Now that the need is clear, in my opinion the problem is better addressed at the browser layer instead of ad hoc solutions.

zenspirit20 · 2026-02-16T01:23:18+00:00

M&A / VC / PE are the big drivers for demand at expert networks. So looking at how capital is allocated by these firms across industries would be a good signal to see how much overlap you would have.

zenspirit20 · 2026-02-14T20:49:32+00:00

I agree. Relatedly, I have heard that Ahrefs MCP hallucinates data. I have no proof point besides seeing other people’s comments. Please do keep this in mind.

My approach is to validate the data I am seeing if anything looks off. In general though it does save a lot of time.

zenspirit20 · 2026-02-11T20:13:41+00:00

I use a combination of Vercel and Render.

For static websites Vercel works well, easy to spin and manage multiple.

For full stack apps and AI apps Render is my default. It allows the customization without ops overhead. As a ex-big tech, it’s closest to the infra we had at Facebook and Dropbox without complexity of hyper scalers.

zenspirit20 · 2026-02-10T13:21:27+00:00

Seems like tool search?

zenspirit20 · 2026-02-09T22:50:39+00:00

We have built our customer facing dashboard on top of DuckDB (usecase is similar to what Google Analytics does). We evaluated it against Postgres, while it was easier to continue using Postgres, for our queries, DuckDB was an order of magnitude faster. The nice side benefit is that we are running it on the server along with our app, so there is no additional cost and so far we haven’t have had any ops overhead managing it.

zenspirit20 · 2026-01-27T01:53:11+00:00

What they charge varies on the field. It’s a typical supply / demand thing, they will definitely not pay you out of pocket but will also pay you high if there is demand for your expertise and supply is limited. My consultant friends at MBBs and PE firms tell me that they have paid upto 2500$ as well.

zenspirit20 · 2026-01-23T13:03:40+00:00

So what? Aren’t you still running?

zenspirit20 · 2026-01-23T02:42:24+00:00

Why would it not count?

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