From Bootstrapped to VC-Funded and Back Again - Introducing Formbot

I'm super excited to be building again after almost 4 years since I launched my last product.

For a quick summary of my story:

• I left my job in 2020 to build self-funded startups
• I launched my first product in 2021
• I sold that product in 2023
• I raised VC investment for my next startup and failed within about 9 months
• I'm back to building startups as side-projects for now!

That just about covers it all, but I think a longer post unpacking this journey might be worthwhile. So here we go...

The Bootstrapped Beginning (2020-2021)

At the end of 2020, in the height of the pandemic, I made what seemed like a crazy decision. I left my Director-level position at GitHub to become a solo indie founder. I attended a coding bootcamp to sharpen my technical skills and then got to work building.

In early 2021, I launched Thread Creator, a tool for creating and scheduling Twitter threads. I built it because I couldn't find a scheduling tool that worked for me, and I was determined to actually finish something instead of letting it become another abandoned side project.

The product gained traction slowly but surely. Over the next two years, it grew to over 10,000 users with 250+ paid subscriptions. It wasn't life-changing money, but it was ramen profitable and proof that I could build something people would pay for.

The Unexpected Exit (2023)

Then Elon Musk acquired Twitter.

The API changes that followed completely upended the economics of Thread Creator. The new API pricing structure would have destroyed the unit economics of the business. When someone reached out with an acquisition offer, I didn't hesitate. The deal was done in a couple of days.

Just like that, my first product was sold.

The VC Experiment (2023-2024)

With some capital from the exit and a taste for building startups, I decided to try something different. I joined Antler, a London-based startup accelerator, for their 10-week program.

I teamed up with two co-founders and we pitched an AI-powered compliance tool for large financial institutions. The idea was solid: help banks and financial services companies navigate their complex regulatory obligations more efficiently using AI.

We raised £120k (~$150k USD) in pre-seed funding. We built a working prototype. We even signed several proof-of-concept deals with potential customers.

And then reality hit us in the face.

Enterprise sales cycles are LONG. Much longer than we anticipated. Much longer than our runway could support. We ran out of cash before we could convert those POCs into paying contracts.

About 9 months after we started, it was over.

Back to Reality (2024)

After the startup failed, I returned to GitHub. I'm grateful they welcomed me back, and honestly, it was a relief to have stability again while I processed what had happened.

The lessons from that experience were invaluable:

• Enterprise sales require patient capital
• Team dynamics matter more than you think
• Having co-founders provides support, but also introduces complexity
• Sometimes the best idea isn't enough if the timing or go-to-market isn't right

I decided that my next venture would be different. I'd build side projects while working full-time. I'd only consider going full-time again once a product started generating decent monthly recurring revenue. No more betting everything on one shot.

The Spark for Formbot

In late October 2025, I came across a tweet from Greg Isenberg that stopped me in my tracks:

AI-Native Conversational Forms ($1M+ ARR)

every website uses forms, but they're outdated yet typeform does $140M+ In ARR

imagine replacing those static boxes with an AI that talks to you, asks follow-up questions, and fills itself out as you type. onboarding, applications, and surveys suddenly feel human instead of robotic.

feels like the obvious next evolution of where the internet is going

He was absolutely right. Forms are everywhere, on every website, in every app, but they haven't fundamentally changed in decades. You fill out static fields, one after another, in a rigid structure that feels robotic.

I couldn't stop thinking about it. What if forms could feel like a conversation instead?

Introducing Formbot

The project I'm now working on is Formbot, an AI-native conversational form builder.

Here's the core idea: instead of filling out boring static forms, your users can simply have a conversation. They type naturally, and the AI asks follow-up questions, clarifies ambiguous responses, and ensures all the necessary information is captured before marking the form as complete.

What makes Formbot different:

1. Build forms in seconds using AI - Describe what information you need, and AI generates the form structure for you
2. Conversational experience - Users chat with your forms instead of filling out rigid fields
3. Intelligent parsing - Behind the scenes, LLMs parse user responses in a structured way, ensuring data quality
4. Natural and human - The experience feels like talking to a helpful person, not filling out a bureaucratic document

I think it's a pretty neat use case for AI, and I'm really interested to see how folks use it.

The obvious applications are things like:

• Customer onboarding
• Lead qualification
• Survey responses
• Job applications
• Support ticket intake
• Event registrations

But I suspect people will come up with use cases I haven't even thought of yet.

What's Different This Time

Building Formbot feels different from both Thread Creator and the VC-funded startup:

Compared to Thread Creator (2021):

• I have 4+ years more experience building and shipping products
• I understand the importance of distribution and marketing from day one
• I'm not betting my livelihood on it, so the pressure is different (better)

Compared to the VC startup (2023-2024):

• I'm targeting SMBs and individuals, not enterprise, which means faster sales cycles
• I'm building solo (for now), which means simpler decision-making and faster iteration
• I'm bootstrapped, which means sustainable growth with no pressure to scale prematurely
• I can take my time to find product-market fit

The biggest difference? I'm patient this time. I know that SaaS is a long game. I've lived through "the long, slow SaaS ramp of death" before. I know it takes time.

What's Next

Formbot is live at tryformbot.com. I'm actively talking to early users, iterating on feedback, and improving the product every day.

I'm building in public and sharing the journey as I go. If you're interested in conversational forms, AI-powered form building, or just want to follow along on another indie hacker journey, I'd love to have you along for the ride.

Let me know what you think of Formbot! I'm always eager to hear feedback, ideas, and use cases I haven't considered.

You can also follow along on X to see how things progress!