Bootstrapping to $40k MRR after his VC-backed startup failed

Thank you for sharing your journey.

1) I wonder how did you get your first costumers to do the first testing? I am always thinking how to get the first customers to try out the app.

2) Any bad experiences with Bubble? I am thinking to create it there as i want it to maka it with no code builder and I want to use the support from Bubble when i will encounter problems.

I just started in this space, and i love reading this journeys. Keep building. And please keep sharing.

Alex, the Pluto travel insurance startup failing during Covid is one of those cases where the timing genuinely wasn't the founder's fault — a pandemic destroying a travel-dependent business is bad luck, not bad execution. What's interesting is what came after: micro-SaaS flipping to learn the bootstrapped playbook, then founding My AskAI with a cofounder rather than going solo. The AI customer support angle is well-timed — companies are actively looking for ways to handle support volume without scaling headcount, and plugging into Intercom/Zendesk means no rip-and-replace decision required. 75K+ support chats/month at $40K MRR with just two people is exceptional capital efficiency. The "flipping micro-SaaS experiments" phase between Pluto and My AskAI is underappreciated — those projects clearly helped you build pattern recognition for what actually converts. What was the most useful thing you learned from those earlier flips?

this was such a refreshing read, Alex. thanks for being brutally real, especially the “growth is messy” bit. we felt that in our bones.

we’re building gudsho a video-first marketing platform for b2b teams (webinars, video editing, hosting, scheduling all in one). totally relate to the shiny object phase. we explored a bunch of ideas early on, but quickly learned to double down on what actually moves the needle.

also loved the part about treating support tickets like marketing. never thought of it that way gonna start replying like the whole internet’s watching.

cheering you on to hit that $1M! and respect for keeping it lean and swimming three times a week

Cheers buddy!

Great writeup, thanks! How did you go about initially reaching out to customers? Cold-email?

Good information

Great hearing the tech stack and "Shiny‑object syndrome".  

Would love to hear more about the chasing of VC money and the challenges it faces.

Great

Incredible journey — going from VC-backed to bootstrapping $40K MRR is huge.

Curious, how did your startup storytelling or positioning change the second time around?

We’re building ZTH to help founders craft stronger, investor-ready decks, and this shift in narrative is something we’re seeing a lot. Would love to hear your take!

post-vc bootstrap stories are my favorite bc the constraints force clarity. the only thing that matters is what customers pay for.

curious what they did differently after the vc startup failed (pricing, scope, or distribution).

Really inspiring journey. Love how Alex turned a tough VC failure into a focused, profitable bootstrap story. The honesty about mistakes, messy growth, and staying product-obsessed makes this very relatable. Proof that clarity, patience, and consistency can beat hype. 👏

I appreciate your journey Alex

Really inspiring journey, Alex! Love how you bootstrapped, iterated fast with no-code, and found product-market fit. Totally agree that growth is messy — your focus on onboarding and clear positioning clearly paid off. Appreciate the honesty about mistakes too; so many founders can relate. Excited to see where My AskAI goes next!

Interesting numbers and lessons, thanks a lot for posting!

Alex, this is such an inspiring story. Going from a failed VC-backed startup to $40K MRR with just two people shows how powerful focus and resilience can be. I love how you kept the product simple upload content, ask a question, get an answer and then leaned on SEO with clear, bold messaging.

What stood out most is how you proved that bootstrapped SaaS can grow fast without burning cash. It’s a reminder that sometimes the lean path actually creates stronger businesses.

On the AI side, have you thought about adding things like auto-triage or sentiment-based support routing? That’s where machine learning really shines. Teams like ValueCoders are helping SaaS founders bolt on that kind of smart automation without needing a big engineering team.

Really excited to see where you take this you’re well on track to that $1M ARR.

Really break breakdown of your entire thought process. I enjoyed reading this!

Love seeing this breakdown, especially the part about niching down sooner. In healthcare, focus matters even more because the stakes are higher. One of the best examples I’ve seen is Alora’s hospice platform... they’ve embedded compliance tools directly into the workflow so nurses barely notice it’s there, but surveyors see all the right data. That’s the kind of clarity and product-market fit I want to aim for.

Also, totally agree with “every support ticket is a marketing opportunity.” In my world, every nurse question or family call is a chance to improve trust , same principle, different industry.

$1M!!! inspiring - need encouragement like that at this early stage. Thanks James.

to start a business like that you need a goal tracker first to know what you ae doing everday

Incredible that you're diving into the solopreneur AI space—it's definitely where a lot of innovation is happening. Balancing clarity and value in a lean product is no small feat. One thing I’ve seen work well is using YouTube as a strategic asset: not just for awareness, but to clearly demonstrate use cases, onboard users visually, and build long-term trust with your audience. Storytelling through video can bridge that clarity gap in a way landing pages often can’t. If you ever need ideas or want to explore how to simplify your tool's message through content, happy to share what’s worked in my experience

Really enjoyed reading this, especially how that moment with OpenAI’s embeddings helped everything fall into place. It’s amazing how one change plus becoming a dad can shift your whole direction.

Our CEO’s story is a bit simpler. He once told me that one evening, he was sitting at home and realized how harsh and cold the ceiling light felt. That’s when the idea for Perlglow came to him. He wanted to create ceiling lights that feel warm, calm, and actually make a space feel inviting and comfortable.

So now, that’s what we’re all about making lighting that helps your home feel more cozy and truly like you. It might seem small, but it makes a big difference.

Incredible story—bootstrapped from zero to $40K MRR on the back of a single use-case nailed is precisely how early SaaS scale should look.

I often tell founders: start with a use case so narrow it feels risky—because that's where product-market fit becomes real. Alex’s journey from micro-SaaS pivots to a focused customer support agent is textbook.

Pivoting from shiny objects, simplifying your tech stack, and doubling down on clear, SEO-driven messaging—that discipline isn’t sexy but it works.

Thanks for showcasing what real traction looks like. This is the roadmap for early-stage founders who want to scale smarter—not just chase VC distractions.

Curious—what was the biggest insight you gained during that messy growth phase that other bootstrapped SaaS founders often overlook?

Really inspiring read. Love how you turned a tough ending into a thoughtful and focused comeback -without outside funding. The contrast between the vc-backed journey and bootstrapped success makes the lessons feel very real. Appreciate the honesty and clarity lots to learn from this )

amazing

Thank you. I have learned a lot from you.

Such a great and inspiring story. I’m thinking about something similar myself. But honestly, I still struggle to believe that one or two people can build a service that brings in tens or even hundreds of thousands of dollars. It feels like you’d need a proper team for that — a big one. Or at least outsource development to skilled professionals.

Really admire your journey—from corporate consulting to building My AskAI!
Handling 75k+ chats a month with just two people is impressive. How did you prioritize features early on to scale without a big team?
Also curious, did you find any surprising challenges integrating with multiple support tools?
Thanks for sharing such an inspiring story!

Thanks for sharing! Curious how you originally handled RAG. And did Anthropic’s MCP protocol changed how your team thinks about retrieval, or your stack at all? Congrats on the success!

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Staying focused is a rare feat, with so many distractions vying for our attention.

This was a super refreshing read.

So many “overnight success” stories gloss over the messy middle. I really appreciated how you talked about the false starts, the pivot, the infra pain, and especially the lack of clean attribution. That part hit hard.

Also +1 on the “growth is messy” take. It’s so true how little you actually know about what’s working while you’re in the thick of it. Sometimes it’s just trusting the right things are compounding in the background.

Thanks for writing this up. Bookmarking it as a reminder that the chaos is part of the process.

Thanks for being so open and real. Respect!

Fantastic read! So inspiring to see Alex's journey from a VC-backed startup failing to building something so successful by bootstrapping. The transparency in sharing the challenges and growth is really valuable.

Love this. Im a new solo dev in the stages of an MVP now and reading this is extremely motivating and comforting knowing im not alone.

Love this story — such a great example of resilience and focus. Bootstrapping to $40k MRR after a failed VC-backed attempt is no small feat. Especially inspiring how you leveraged no-code tools and stayed scrappy while learning from early mistakes. Huge respect for staying product-obsessed and prioritizing real customer value. Thanks for sharing the journey so transparently

SEO in 2025, interesting

Really interesting how My AskAI leaned heavily on SEO and organic visibility for growth.

We’re noticing a shift where people don’t just search on Google anymore — they ask ChatGPT, Gemini, and other AI tools for recommendations. That raises a new challenge: how can startups ensure their brand actually shows up in those AI-driven answers?

Curious if you’ve seen any impact from generative AI on how new users are finding you. Are you adapting your visibility strategy beyond Google?

yeah not easy but totally worth it

good work!

Love how honestly you’ve broken down the messy reality behind those clean MRR charts we see online. A few reflections:

1. Selling before building is underrated, even with AI hype.

2. Picking one clear niche early saves a year of pivots.

3. SEO and specific copy still outperform fancy tactics.

4. No-code isn’t a hack; it’s a force multiplier if you stay focused.

5. Growth is never linear, but consistent small actions stack up.

Thanks for sharing real numbers and hard lessons. Posts like this are gold for early-stage builders trying to filter noise and move deliberately.

Congrats Alex!

Love this. Im a new solo dev in the stages of an MVP now and reading this is extremely motivating and comforting knowing im not alone.

Love this. We’re bootstrapping our own SaaS right now, and posts like this really help keep the motivation up. Always makes me wonder how much of VC success is just burn runway vs actual traction.

Turning failure into fuel, he bootstrapped his way to $40k MRR after his VC-backed startup collapsed. 💥 With no outside funding and lessons learned the hard way, he built smarter, leaner, and with laser focus. Proof that resilience, grit, and product-market fit can outshine venture capital. This is how real founders rise after the fall. #BootstrapSuccess #MRRJourney #FounderComeback

Damn Alex, this hit close. I totally fell into the overbuilding trap — trying to make everything perfect before even getting feedback. I’ve made free tools, cleaned up UX, even baked in SEO from day one… but getting those first real users feels like pushing a boulder uphill.

Your honesty around growth being “messy” and that even you didn’t have a perfect playbook — that gave me a weird kind of peace. Appreciate you sharing the reality, not just the MRR screenshot.

Respect for keeping it lean, focused, and human.

Love this. Super inspiring how you kept it lean, pivoted with clarity, and found traction without chasing hype. $40k MRR with just two people is no joke — thanks for being transparent about the mistakes too. Lots to learn here.

Great Article

Bootstrapping to $40k MRR！good team！

Do we think the rise and release of agentic browsers this summer are a threat or opportunity for businesses like this?

This was such a refreshing and honest breakdown—thank you, Alex.

The “growth is messy” part hit especially hard. So often we look for silver bullets or perfect attribution, when in reality it’s just showing up consistently, staying close to users, and iterating through the fog.

Also really appreciate the mistakes section—particularly the point about shiny-object syndrome and going too broad early on. It’s comforting (and validating) to hear that even success stories had chaotic, uncertain beginnings.

One question: looking back, was there a specific moment or decision that you feel really shifted momentum from “experiment” to “real traction”?

Rooting for you to hit that $1M ARR mark. 🙌

This journey is genuinely inspiring—turning a failed VC-backed startup into a hyper-focused, bootstrapped success with $40 K+ MRR (now $45 K) is no small feat. A few highlights that really resonated:

1. Iterate fast and often: Building 10 products in 12 months reflects incredible grit. You embraced failure as a learning engine, not a setback. That kind of persistence pays off

2. Build for growth, not just product: Your “two stacks” approach—one for the product, one for growth—perfectly illustrates why micro‑tools + content-led SEO can outperform feature bloat

3. Bottom-of-funnel SEO is underrated: Ranking for comparison and alternative keywords drove highly motivated users. That’s 💡 smart. Your advice to write alternative pages for existing tools hits the nail on the head

4. Align with what you enjoy: Your reminder that the process must be fun is crucial. Building tools is tough—if it drains you, even good traction won’t last

Huge congrats on reaching ~$45K MRR and aiming for $1M ARR. Your transparency about failure, resilience, and SEO-led growth is a masterclass for founders aiming to bootstrap smart. Thanks for sharing the gritty, tactical details! 👏

Incredible journey

Incredible journey, Alex — love the transparency around the messy middle, especially the pivot from "chat with anything" to focused customer support. Huge respect for building to $40k MRR with just two people.

Loved the point about specificity in website copy being your SEO secret weapon. It’s something so many startups overlook in favor of flashy marketing. What kind of pages or content performed best for you SEO-wise? Feature comparisons? And how early did you start investing in content?

With pure grit and focus, he bootstrapped his way to $40k MRR after his venture-backed startup collapsed. There is no funding, no hype, just solving real problems and listening to users. There is a powerful message here: momentum does not require millions of dollars to be built. There are times when failure fuels the most successful pivots. As this journey illustrates, resilience and clarity can outperform even the most flashy of funding rounds.

when I feel depressed and then I face that kind of articles, I really feel like I need to go further and not give up!

This story is such a refreshing and motivating reminder that failure isn’t the end — it’s often the foundation of something more sustainable and authentic. Bootstrapping to $40k MRR after a VC-backed startup collapses takes not just resilience, but a clear understanding of product-market fit and the discipline to grow without external pressure. What really stands out is the shift from chasing hypergrowth to building something customer-first, lean, and profitable. That kind of intentional growth is underrated but powerful.

It also highlights how failure can teach you what not to do: like overhiring, building features no one asked for, or scaling too fast. By contrast, the bootstrapped journey is grounded in customer validation and thoughtful iteration — it’s slow, but it's real.

And on a personal note, while reading through this journey and reflecting on the grit it takes to rebuild, I glanced at my screen and saw my cheerful Kuromi Wallpaper in the background — a gentle reminder that even in serious entrepreneurial hustle, there's room for joy, color, and personality.

Kudos to the founder — this is the kind of story more early-stage builders need to hear.

This was a masterclass in transparency and clarity. The way you’ve embraced constraints and doubled down on focus is genuinely inspiring. Wishing you a clean shot at that $1M ARR mark 🙌

Very inspiring story

Love this story, Alex — it perfectly captures the resilience and clarity that often come after a painful startup failure.

What really struck me was your shift from chasing scale with VC to embracing control and flexibility with a lean, profitable product. My AskAI is a brilliant use of OpenAI embeddings in a real-world use case (support), and the $0.10-per-ticket value prop is hard to beat.

Also respect the fact that you’re doing this with just two people. Proof that focus and timing > team size.

Curious: how did you validate demand early on, and when did you know it was time to go all-in?

This is such a refreshing story, proof that bootstrapping forces clarity and hustle in a way VC money sometimes doesn’t.

Loved the part about treating growth like product dev, super underrated mindset shift.

I'm currently bootstrapping a wild AI project (called Angry John, basically an unfiltered AI with PTSD and zero chill 😅), and stories like this keep me grounded. Appreciate the transparency and mindset breakdown, bookmarked this one.

Curious: What was your biggest mental shift going from venture mode to solo-builder mode?

Absolutely loved reading this, Alex. There’s something raw, real, and refreshingly honest about the way you’ve shared the journey — especially the pivots, missteps, and growth clarity that came after getting your hands dirty.

I’m at a very similar inflection point — building something I believe could be genuinely useful in this AI wave.

I’m working solo (for now) on a SaaS + content hybrid platform centered around AI tools discovery — something like a supercharged resource hub for devs, marketers, creators, and business folks to not just find, but understand and compare AI tools. We’re focusing heavily on categorization, use-case mapping, pricing transparency, and real-world insights — stuff that's often missing in current platforms.

It’s still pre-launch, but my vision is long-term: to build a living system that combines product hunt-style freshness with deep blog-style breakdowns and SEO-first structure. Monetization will be SaaS-style (premium listings, analytics, lead-gen) with a strong inbound content engine under the hood.

Right now, I’m:

• Finalizing MVP with a custom CMS + dynamic tool pages

• Building contributor/editor tools for verified AI makers

• Working on recommendation logic by user persona (e.g., “I’m a founder looking to automate customer onboarding — what should I use?”)

What I don’t have yet is a team, feedback loop, or experienced co-builders who've been through the trenches like you.

So, for anyone reading:

• If you're into product-led SEO, tool discovery, AI workflows, or SaaS ops, I’d love your thoughts

• If you’ve scaled a SaaS like Alex and want to mentor/advise/collaborate, I’m all ears

• If you’re exploring new acquisitions, and this aligns with your thesis — happy to chat

Not here to pitch anything — just trying to build something real, share the journey, and find people who resonate with the mission.

Thanks again for this post. Genuinely inspiring 🙌

Hey Alex,

Thank you for sharing your inspiring story! I'm also in the process of building a SaaS product on Bubble.io.

I had a question regarding your analytics setup, particularly since I see you're using Amplitude. It seems to me that this tool should allow you to easily connect the acquisition channel, first visit, first landing page, and plan purchase.

If you're having trouble with this, it might be a good idea to consider hiring someone to ensure proper implementation of your analytics. As an official Mixpanel partner, I can’t directly assist, but I believe your challenges can be resolved with the right contractor.

Thanks again for sharing your journey—it's truly inspiring!

That’s an inspiring turnaround! Bootstrapping to $40k MRR after a VC-backed failure shows real resilience and smart strategy.

Really curious what their onboarding process looks like now. Dropping churn from 9% to 3% is no joke, especially at $40k MRR. That kind of retention is way more impressive than the revenue, honestly.

🎯 I’m looking to interview 50 people. You’ll get a $5 gift card for your time.

I’m building a new assistant tool — early stage — and I want to hear from real users before I go further.

If you fall into any of these categories, I’d love to talk for 10–15 mins:

✅ You sometimes struggle with websites, apps, or digital tools

✅ You help others use technology (parents, clients, coworkers)

✅ You’re neurodivergent (ADHD, Autism, etc.) and want simpler tools

✅ You love productivity tools like Notion, ChatGPT, Obsidian

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I’m not selling anything — just testing an idea and would really value your take.

👉 Drop a comment or DM me if you’re open to a quick Zoom chat — I’ll send a link + the $5 after we talk.

Thank you 🙏

great article, in terms of client profile and adhering to regulatory requirements, I presume the model is trained wholly on the document the client provides?

Thinking as a use case for a fintech which is subject to FCA guidelines re advisory etc..

"Treat constraints as features, they force focus."

🔈🔈 That's a precious advice

As an indie hacker, you have to be laser focused on what you want to do

And want you CAN do differently than already established competitors

One single small feature can make all the difference

Super inspiring. Love how failure didn’t stop you—it just redirected the path. Crazy what focus (and no funding pressure) can unlock.

Shiny object syndrome...death.

Love this Article! This resonates so much. The failure taught you what NOT to do, but what specific lessons from the VC experience actually helped you bootstrap successfully?

Loved this. I'm running a POD store solo and totally relate to the growth mess and shiny-object trap. "Constraints force focus" hit hard. Respect for building it lean.

Small team can lead to success

Very informative post! Thank you for sharing your journey, and also - congratulations!

Thanks for “Mistakes were made”, quite insightful

Me parece genial la idea de combinar AI con diseño. ¿Probaste cómo responde en mercados fuera de EE.UU.? Yo estoy intentando algo similar para LATAM y cambia mucho el comportamiento.

Buena forma de generar igresos