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Ask HN: 15 Years, 9 Startups, 0 Big Wins – Should I Quit or Keep Going?

10 points by bibinmohan 1y ago

Hey HN, I'm Bibin Mohan, a 37-year-old founder from India. I started selling firecrackers at 15 and jumped into entrepreneurship full-time at 22. I’ve been at it ever since — 15 years, 9 different startup attempts, and still grinding. I dropped out of college in 2009 to co-found a web and digital marketing agency with three friends. They left within a few years, but I kept it going and still run it today. It pays my family's expenses, but not much more. In between, I got lucky — in 2014, I became the social media consultant to India’s former Central Minister of Shipping & IT through my agency. It was a proud moment, but also a reminder that consulting doesn’t scratch the startup itch for me. Here’s my startup timeline: 1. Quadregal (2009–Present): Web & digital agency. 500+ projects completed. Bootstrapped and sustains my living. 2. Likebids (2010–2011): Social bidding platform using Facebook Likes to win products. It went viral, featured on Mashable. FB changed its ToS and killed the model right before a possible investment. 3. Facebook Apps (2011–2012): Built viral apps like “My Best Chat Friend” (used FB APIs to calculate your most chatted friend). One app hit 1M users in 6 months. All were shut down when FB banned auto-publishing. 4. Glist (2020–2021): A 10-min grocery delivery startup in India (like Zepto). Interviewed at YC, didn’t get in. Got an offer of $120K for 70% equity — we declined and shut it down due to lack of capital. 5. Ippow (2021): 20-minute medicine delivery. No cofounders, no capital, no traction. 6. Healthy (2022): EMI-based healthcare package booking. Stalled due to disinterest and funding issues. 7. 5mino (2023): Mental health + time-focused app. Built it, no downloads. Learned a lot though. 8. Flowstate (2024): Simple app that plays relaxing music. Got 2K+ downloads organically. Growth stalled. 9. Tillit (2024–Now): My current project with two cofounders. It's like Faire for India. We’re turning local homes into mini-warehouses, enabling faster wholesale delivery and giving shopkeepers credit-based inventory. Retailers save money, time, and space. The idea works — I’ve validated it in the field. But we’re constrained financially, funding everything from my agency income. And we need to offer credit, which is hard to scale without capital. Now here’s my dilemma: My wife asked me today if I’m crazy to keep chasing these ideas instead of just taking a job. I’m 37, married, with a child. I've built multiple products, none have "made it", and I'm still hustling every day, believing the next one will. So — do I need more motivation, or should I finally quit? Have you seen someone like me turn it around this late? Am I just being stubborn, or is there still hope if I keep going? Would really appreciate some honest advice from this community. Thank you, Bibin Mohan

bibinmohan 1y ago
Thanks for reading this long post!! Just to add — I’m not looking for sympathy or praise. I genuinely want honest advice from fellow builders and thinkers here. If you’ve been in a similar place — hitting walls, pivoting endlessly, with family pressure mounting — what helped you decide to keep going or step away? Also, if you think there’s a smarter way I should be leveraging my skills or experience, I’m all ears. I’m not married to any single idea — I just want to build something that works and helps people. Thanks again.
pettycashstash2 1y ago
At 37, you're actually at a prime age for entrepreneurship. Research from the Harvard Business Review found the average age of successful startup founders is 45, with the highest-growth startups founded by entrepreneurs with an average age of 45-50. Your accumulated experience is an asset, not a liability. Rather than seeing this as a binary choice between continuing or quitting, consider a third path: being more selective and focused. What if you committed fully to Tillit for 18-24 months with clear milestones and decision points?
- bibinmohan 1y ago
  Thanks a lot. I’m going to sit down and define what success looks like for Tillit over the next 18–24 months — in terms of traction, funding, and team growth. But still with the current situations, I don't know, how long can I move. Would love to know: What kind of milestones or decision points would you recommend for an early-stage marketplace like Tillit that’s solving cash flow and delivery problems for retailers?
  - pettycashstash2 1y ago
    3-Month Milestones: Onboard 20-30 retailers consistently ordering through your platform Establish 3-5 functioning mini-warehouses in one focused neighborhood or district Achieve 70%+ retention rate (retailers placing second and third orders) Demonstrate consistent 1-2 day delivery timeframes vs. industry standard 6-Month Milestones: Develop a simple but scalable credit scoring system for your retailers Implement a minimal credit offering for your best customers (even if limited) Create streamlined logistics model that can handle 3-5x your current volume Document 3-5 case studies showing measurable retailer benefits (time/cost savings) 12-Month Decision Points: Revenue covering operational costs (excluding your time) 10-15% month-over-month growth in transaction volume Clear unit economics showing profitability per delivery At least one key metric where you're 2-3x better than traditional wholesalers Rather than trying to fund everything from your agency, consider a "minimum viable credit" approach - perhaps starting with net-15 payment terms for your most reliable retailers, then gradually extending as you validate repayment behavior. Could you saturate just one neighborhood or product category first to demonstrate density advantages? The key now is focused execution rather than trying to solve every problem at once. What's the absolute minimum version of Tillit that delivers real value and can grow without significant outside capital?

GianFabien 1y ago

Your wife is a gem, putting up with your chasing opportunities with poor market fit. The essence of business is delivering something that people want so much that they are willing to pay for it. It appears that with Quadregal (I assume it is the consulting biz you mentioned) you have over 500 successes. Based on the information you have shared it appears to be a successful business. If you were to stop thinking the grass is greener elsewhere, you might realize that the grass under your feet is already green and with more watering and care it would be the greenest. Wouldn't you be making even more money than by taking a job if you were to focus your talents and energies upon the business that is already supporting you and your family? Taking agency income to prop-up a capital intensive idea is not honoring your responsibility to your family and your patient wife. You only need to quit doing what doesn't work and do more of what does.

bibinmohan 1y ago
Thanks for this perspective — truly appreciate your honesty. You’re right in pointing out that my wife has been incredibly patient and supportive through all this. I’m lucky there. And yes, Quadregal has indeed been my safety net all these years. I’ve always seen it as a fallback, not the main bet — but maybe I’ve been undervaluing the fact that it has delivered consistently. I guess I got caught up in chasing bigger “startup-style” wins and forgot that there’s real value (and freedom) in growing something that already works. That said, I still feel there’s something powerful in Tillit’s core idea — but you’ve made me realize that I need to draw a line between ambition and recklessness. Maybe there’s a middle path: treat Tillit like a disciplined side venture (with clear boundaries), and double down on growing Quadregal with the same energy I pour into these “new” ideas. Thanks again for the much-needed reminder Would love to hear how you’ve approached similar crossroads, if you’ve faced them.
- GianFabien 1y ago
  I appreciate you responding to my comments. Rarely do I get any responses from the person originally posing the question. I got involved in my first startup soon after I graduated with my undergrad degree and started on a part-time masters degree. I worked on a day job to pay my rent, food, etc. And I worked for the startup the rest of the time. Sometimes I would work all night and go to the day job without any sleep, just a quick shower. It didn't work out. The startup did a pivot and in so doing screwed me out of at least a million AUD. That was lesson #1. It was decades ago. I have since been involved in many other startups, most on a full-time basis. Varying durations until runway got burnt up. I'm very much the tech guy. In hindsight I put too much faith in the business acumen co-founders and investors. Had to return to consulting work in between those startup attempts. That is how I kept myself afloat. I'm in Australia and VCs are nothing like those in SV. In general risk aversion is high and the success dynamics in the USA don't translate well to local conditions, culture, etc. I think you may be in a comparable environment. So you need to temper your expectations for Tillit in light of your local environment. Read up on Steve Blank https://steveblank.com/books-for-startups/ https://steveblank.com/books-for-startups/ The takeaway: find product market fit. If you don't you don't have a business. I have gone on to get my PhD in software engineering and from time to time I teach at one Australia's best universities. I'm now retired courtesy of some good real-estate investments. I learnt a lot about the business world through consulting work. I now focus technical mentoring for startups on behalf of the investors rather than the founders.