How Overthinking Burned ₹200 Cr🔥
Plus: how a failed fintech pivoted to ₹9 Cr ARR, bootstrapped.
Hello Minters,
Welcome to this week’s edition!
My goal with this newsletter is simple: To bring you the most interesting and insightful stories from the world of startups, business, and innovation, all in one place.
Let’s start?
The ₹200 Crore Opportunity Dheeraj Jain Missed and the Lessons He Learned
(confession & wisdom from Dheeraj Jain, Founder of Redcliffe Labs, Crysta IVF, PeeSafe & early-stage investor, show him some love on LinkedIn)
In a candid LinkedIn post, seasoned investor Dheeraj Jain shared a powerful story of a missed opportunity that could have turned a ₹50 lakh investment into a staggering ₹200 crore.
The story serves as a valuable lesson for investors and founders alike, highlighting the fine line between prudent analysis and overthinking.
It all began nine years ago. Fresh off an investment in Shipsy, Jain was introduced to the founders of a new startup called Meesho by one of Shipsy's co-founders, Dhruv Agrawal.
At the time, Meesho was raising its angel round at a valuation of around ₹20-25 crore. For Jain, who was regularly writing cheques of ₹40-50 lakhs, this was a familiar scenario.
However, he passed on the investment.
His reasoning was a question many would have asked: "How could a small e-commerce startup compete with the likes of Flipkart and Amazon?" As Jain recalls, "There was too much noise. Too many decks. Too many decisions."
He told himself he would consider it "later," but that moment never arrived.
Today, Meesho, famously backed by Facebook, has not only survived but has grown to become a formidable competitor to the very giants Jain believed were insurmountable.
While he finds it incredible to witness their journey, he admits to still carrying the "miss" of that ₹200 crore opportunity.
From this experience, Dheeraj Jain extracted several key learnings which he generously shared:
Distribution Trumps Product (in the early stages): Jain notes that while Meesho's app wasn't initially the best, their understanding and execution of distribution were unparalleled. They successfully penetrated Tier 2 and Tier 3 markets through a brilliant social selling model.
The Power of Founder-Market Fit: The founders of Meesho had a deep and authentic understanding of their user base. They weren't simply imitating existing models; they were solving real, on-the-ground problems for their customers.
Simple Models Can Scale Exponentially: The technology behind Meesho wasn't revolutionary. Instead, their success was built on flawless operations, strong community-building, and creating cycles of trust.
Jain concludes that he missed this monumental opportunity because he "overthought it." However, he emphasizes that this is an inherent part of the investment game.
His closing message is one of resilience and continuous learning: "You don’t win by never failing. You win by staying in the game long enough to learn, adapt, and back the next Meesho when it shows up."
You can read Dheeraj Jain's original post on LinkedIn here.
A Failed App, 3-Year Detour and ₹9 Crore Bootstrapped Comeback
(shared by Anant Deshpande, Co-founder @ FinBox, go follow him for more wisdom)
How many times have we seen a promising product fail, only for its founders to disappear? The story often ends there. But what if the initial failure isn't an end, but a necessary detour?
Anant Deshpande, co-founder of FinBox, recently shared a powerful story that turns the conventional failure narrative on its head.
It’s a masterclass in resilience, learning, and recognizing hidden value and it culminated in a ₹9 Crore ARR (Annual Recurring Revenue) business, built without a single rupee of outside funding.
The Story: From a Failed App to FinBox v2
It began with a common startup dream: a consumer fintech app designed for personal finance management. Anant and his co-founders spent months building, launched their product, and went out to raise funds.
They quickly hit a wall. As Anant puts it, they were "too early and maybe just too naïve."
They had a functional product, but no viable business model to support it. The market wasn't buying what they were selling. Instead of forcing the issue, they made a tough call: they put the app on hold.
What came next is the most crucial part of this story.
The team didn't immediately jump to a new idea. Instead, they took a three-year "sabbatical" from being founders to become, in Anant's words, "students of the ecosystem."
His co-founders dove deep into logistics SaaS, while Anant immersed himself in the lending sector, working across credit, partnerships, and risk.
This period of hands-on learning proved invaluable. It was during this time that the "aha" moment struck.
The infrastructure they had built for their original consumer app, the core technology and frameworks wasn't useless. It was incredibly powerful. They had simply been pointing it at the wrong customer.
This insight sparked the pivot. They re-oriented their existing tech towards a new market: B2B SaaS for the lending industry they now knew so well. They launched FinBox v2.
The result? In its first year, the bootstrapped venture hit ₹9 Crore in Annual Recurring Revenue.
Anant’s core insight is profound: "Sometimes, the market doesn’t reject your idea. It just redirects you to the right direction."
Our Takeaways: How You Can Apply This
Anant's journey is more than just an inspiring story; it's a strategic playbook for anyone building a business. Here’s what we can learn and how you can apply these lessons:
1. Your First Idea is a Compass, Not a Map: The FinBox team’s initial app wasn't a failure; it was a starting point that helped them discover a much bigger opportunity.
Actionable Insight: Don't be afraid to launch with an imperfect business model, but be prepared to listen intently to market feedback. Treat your initial launch as a large-scale experiment designed to find the real, paying problem.
2. Get Paid to Learn: The founders didn't burn through cash trying to find their next idea. They went and worked within the industry, gaining deep domain expertise. This de-risked their future pivot significantly.
Actionable Insight: If you're stuck, consider getting a job in the industry you want to serve. Working as an "employee" allows you to understand customer pain points, market dynamics, and operational realities on someone else's dime. This firsthand knowledge is more valuable than any market research report.
3. Conduct an "Asset Audit" Before You Pivot: The breakthrough came when they realized their existing tech was a valuable asset. They didn't have to start from zero.
Actionable Insight: Before throwing a project away, perform an audit. What have you really built? List your assets: codebases, infrastructure, domain knowledge, customer waitlists, brand recognition. Can these assets be repurposed or "re-aimed" at a different customer segment or problem? You might be sitting on your next big thing.
4. The Best Pivots are From Noise to Need: FinBox v2 succeeded because it shifted from chasing a popular trend (consumer fintech) to solving a specific, urgent need for businesses (lending infrastructure).
Actionable Insight: Constantly ask yourself: "Am I solving a 'nice-to-have' problem or a 'must-have' one?" Businesses pay for solutions that directly impact their bottom line: reducing costs, managing risk, or increasing revenue. Find that urgent need, and you'll find your business model.
Anant Deshpande’s story is a testament to the fact that the path to success is rarely linear. By embracing a deep learning phase and recognizing the hidden value in their "failure," the FinBox team built something far more robust and successful than their original vision.
Original story shared by Anant Deshpande on LinkedIn.
Handpicked Jobs in the Startup Ecosystem
1. Producer / Showrunner · Video & Reels Editors · Content Researcher · Social Lead → build Offline’s new creator newsroom
Remote-friendly (India), digital-first storytelling
Shape formats, book guests, cut long-form & meme-ready clips, run socials. Needs taste + speed.
Apply: DM @ offline_members (Instagram) or email via Offline site with work samples.
Posted by: Utsav Somani – Founder, Offline (linkedin.com)
2. Biz-Dev Rep & Partnership/Growth Exec → fintech rain-makers | IppoPay
Chennai / Tamil Nadu • fast-scaling payments start-up
Own new-merchant pipeline and strategic alliances; targets + rev share.
Apply: careers@ippopay.com or WhatsApp +91-89258 47078.
Posted by: Mohan K, Co-Founder & CEO, IppoPay (linkedin.com)
3. Business Relationship Manager – Banks, NBFC & DSAs → first 25 hires | AbleCredit
Bengaluru (Bannerghatta Rd) • 3-5 yrs lending-channel ops • ₹4-10 LPA
Build & scale partner network; full loan-file flow for HL, LAP, PL.
Apply: LinkedIn Easy Apply or reach out to poster.
Posted by: Deepak Seshadri, Founders’ Office & New Initiatives, AbleCredit (linkedin.com, in.linkedin.com)
4. 10 hand-picked marketing & design roles across D2C, space-tech & wellness brands | SuperStuff.ai
Bengaluru / Ahmedabad / Gurgaon • 2-9 yrs • ₹10-42 LPA
Community, Brand, Growth, Product-Mktg & Design positions—all vetted.
Apply: filter & apply at apply.superstuff.ai (link in post).
Posted by: Pranay Swarup, Founder, SuperStuff.ai (linkedin.com)
5. SEO Manager → own organic rocket-ship | Jaagruk Bharat
Delhi NCR (on-site) • plan + execute SEO, KW & competitor audits.
Apply: DM Akshit with case-study links.
Posted by: Akshit Goel, Co-Founder, Jaagruk Bharat & TNW (linkedin.com)
6. Chief Financial Officer → leadership bench | 4baseCare (precision oncology)
Bengaluru / hybrid • scale Series-A health-tech across regions.
Drive strategic finance, capital planning & investor reporting.
Apply: Refer qualified profiles directly to Hitesh on LinkedIn.
Posted by: Hitesh Goswami, CEO, 4baseCare (linkedin.com)
7. Meta Ads Freelancer (Facebook + Instagram) → growth partner | Etzu (women’s D2C fashion)
Remote (India) • 2+ yrs paid-social • ROAS obsessions.
Apply: info@etzu.in subject “Meta Ads Freelancer – Etzu” + portfolio.
Posted by: Akshay Nath, Founder, Etzu (linkedin.com)
8. Founding Full-Stack Engineer (SDE-1) → equity-only co-builder | Kagaar
Remote • 4–5 hrs/day • Next.js, Node, Mongo, LLM APIs.
Build India’s founder-investor network from ground zero, in return, real ownership.
Apply: https://lnkd.in/g5KmkESE or hireme@kagaar.in.
Posted by: Prashant X, Founder & CEO, Kagaar (linkedin.com)
9. Finance / FP&A / Commercial team (multiple levels) → IPO-ready journey | Ultrahuman
Bengaluru WFO • 3-10 yrs controllership, treasury, business finance.
Preference for manufacturing-plus-D2C exposure; ERP & IPO prep a bonus.
Apply: finance-careers@ultrahuman.com (subject: domain + notice period + CTC).
Posted by: Bhuvan Srinivasan, Chief Business Officer, Ultrahuman (linkedin.com)
10. Senior Creative Strategist → shape creator-led campaigns | Monk Entertainment (Monk-E)
Mumbai office • 2-4 yrs agency/brand strategy • pop-culture native.
Craft big ideas for top global brands in the creator economy.
Apply: careers@monk-e.in subject “Here’s your best creative strategist” + portfolio.
Posted by: Viraj Sheth – Co-Founder & CEO, Monk Entertainment (linkedin.com)
11. Founding Software Engineer (0–2 yrs) & Senior Software Engineer (2–5 yrs) → early builder’s seat | Heizen
Hyderabad / Remote • “quick-software” startup growing 20 % MoM • 6 openings
Ship customer MVPs end-to-end, own features, and work directly with the founding team.
Compensation: ₹12 L + ESOPs for Software Engineers, ₹24 L + ESOPs for Senior Software Engineers.
If you thrive on autonomy, fast cycles, and purposeful work, this is your playground.
Posted by: Aman Arora, Co-Founder & Chief of Growth & Technology, Heizen (linkedin.com)
Apply: Fill out the Google form or email hiring@heizen.work with the subject “Founding Engineer – Heizen”.
Share this list with hustlers hunting their next rocket seat, referrals always win!
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Thank you for reading.
Until next time,
Aditya