Overcoming Startup Challenges

"Why are you building from Kolkata?" - Wrong question. The right question is: "Why isn't everyone?" Last week, I sat with Vikram Gupta (Ex-Army Major, Founder of Flexi) and 12+ founders who chose Kolkata as their base. Not by accident. By design. Here's what the "smart money" in Bangalore doesn't want you to know: - While they burn ₹2L/month on office rent, Kolkata founders get premium space for ₹50K. - While they fight for overpriced talent, Kolkata has hungry, skilled professionals waiting. - While they chase the same 100 VCs, Kolkata founders bootstrap to profitability. The 3 insights that blew my mind: → Quality trumps location: Customers don't care about your office pin code when you deliver consistently. They care about results. → AI levels the playing field: These founders are using AI to leapfrog - customer support, hiring, product intelligence. Geography becomes irrelevant when your operations are smarter. → Strategic expansion wins: Half these founders are opening Bangalore offices next. Not to relocate - to dominate markets they're already winning from Kolkata. That building from Tier 2 cities is settling for less. Lower costs = longer runway = better decisions = sustainable growth. While Bangalore founders are on their 3rd funding round, Kolkata founders are hitting profitability. Geography isn't destiny. Capital efficiency is. Maybe we should stop asking founders to justify their location. And start asking why everyone's crowding into the same expensive cities. Which Tier 2 city will surprise us next?

Most startup finance functions weren’t built for scale. They were patched together by founders. Which means when you step in, you’re inheriting: – A founder-led forcast built for fundraising not how your business actually make money – A chart of accounts designed in a panic – “Reporting” that’s basically a spreadsheet stitched with hope – And KPIs no one can agree on Let’s be honest: It’s a mess. And worse? It’s blocking the decisions that matter most. I’ve rebuilt five finance functions - two in-house, three as a fractional partner. Every time, the pattern is the same: You’re not just cleaning up numbers. You’re rewriting the financial story of the company. Here’s how I turn finance from a lagging function into a strategic driver: → Step 1: Rewire the chart of accounts If you’re SaaS and services, your P&L should reflect that. We make it readable and actionable, not just GAAP compliant. → Step 2: Connect the stack Automate billing. Tighten up payroll. Sync tools across the funnel. Your finance ops should reduce friction, not add to it. → Step 3: Rebuild the model Most founder-built models are optimism on steroids. We anchor it to real unit economics and GTM motion, not just investor dreams. → Step 4: Define the right metrics If your CAC and LTV don’t line up between Sales, Marketing, and Finance, you're playing broken telephone. We build alignment across functions and drive confident decision-making. → Step 5: Standardize reporting Cash for survival. Accrual for strategy. One monthly pack. Built to inform execs and impress investors. → Step 6: Build the finance ecosystem RevRec. Scenario planning. Burn runway modeling. We design the function around your real inflection points. Because finance shouldn't just report on performance. It should enable it. Done right, it becomes the backbone of your decision-making, not a spreadsheet you scramble to update the night before a board call. And frankly? This is the work I love the most. Because every time we rebuild it right, the fog lifts and founders lead with clarity again. PS: What’s the one part of your finance function you know is holding you back, but haven’t had time to fix? PPS: If you're scaling with duct-taped dashboards and gut-feel forecasts, let’s talk. You don’t need to build your operating system alone.

In 66 months, I helped grow Gong from $200k ARR to $7.2B in valuation and worked alongside some of the planet's best sales leaders. Here's the 6 biggest lessons I learned: 1. Overinvest in great marketing early on. I’m still shocked at how few startups do this. Sales with no (effective) marketing early on to pave demand and provide air-cover is a brute-force way to build. 2. Measure twice, cut once when hiring leaders. Your first leadership hires will have cascading effects on your company that ripple through many years. Their fingerprints will weigh heavy on everything from your sales motion, to company culture, to the people they hire, whether you want it to or not. Even after they’re gone. Recruit and hire accordingly. 3. Beat the hell out of what’s working. Finding what works in growing a startup is like drilling for oil. You’re going to drill a number of "wells" and come up dry. But soon, you’ll find one to go DEEP with. Drill it for all it’s worth. Don’t screw around trying to find too many other oil wells when you haven’t even maxed out your best one. 4. Hire salespeople who thrive on ambiguity. Not just those who CAN do that, but those who LOVE to do it (because they'll be doing this for a while as your market evolves). Do this, and you’ll accelerate your learning curve to a repeatable sales motion. Hire entrepreneurial reps. 5. Inject risk into the business as you scale. As you scale, your “portfolio” of growth initiatives should contain more and more risk. It's as if you're a fund manager. Early on, find what works and cling to it. But as you grow and you’re able to rely on several well-established growth vectors, start to introduce risk into your portfolio. Examples: Experimenting with channel partnerships, international, new segments of the market or use cases. 6. Realize the "growth at scale" playbook is different than the "scale up" and "startup" playbooks. What got you to $50M or $100M will not get you to the next level by itself. The path to $100M, and going beyond that (“growth-at-scale”) are two very different situations demanding different means of growing. Early on, nothing matters but (the right) customer acquisition, controlling churn, and making your product absolutely amazing. But if you’re going to continue growing at a fast rate, several other methods have to start firing: high net dollar retention (NDR), multi-product and multiple streams of ARR, going hard and fast on international expansion, and crossing the chasm into “low tech” industries. This list is non-exhaustive. For those of you who have ridden that tornado, what would you add? P.S. Turn "open opps" into paying customers at any phase of growth with these 10 closing motion scripts: https://lnkd.in/gtxYd9Vs

What once seemed like the ultimate strategy—domiciling in the US, Singapore or the Netherlands—has now taken a full U-turn. Indian startups are reversing their earlier decisions and shifting headquarters back to where it all began. The term? “Reverse flipping.” The reasons? A mix of regulatory ease, robust domestic funding, and a thriving IPO market. The stars of this movement include heavyweights like Razorpay, Udaan, Pine Labs, and Meesho, while Zepto has already crossed the finish line. And it’s not just a few isolated cases—industry estimates indicate over 70 startups are currently in the process of shifting back, with another 500 still domiciled abroad, watching and evaluating the trend. Why the Sudden Shift? Historically, startups sought foreign domiciles to tap into global VC funds, benefit from friendly tax regimes, and eventually go public on high-profile exchanges like NASDAQ. But the tide is turning. India’s IPO market has matured significantly, offering startups a compelling alternative. Let me take an example of Mr. Alok Bathija, Partner at Accel, who explained that a software firm with $50-$60 million in revenue can now list in India, whereas a similar listing in the US would require nearly $500 million in revenue. With higher valuations and greater accessibility, the incentive to stay within India’s financial ecosystem has never been stronger. Furthermore, regulatory burdens abroad are becoming more cumbersome, while India is streamlining the process for startups to return. The abolition of the angel tax, RBI’s support for fintech regulation, and a simplified approval system (previously requiring National Company Law Tribunal clearance, now reduced to just government and RBI approvals) have made the transition far less daunting. Perhaps the most high-profile returnee has been PhonePe, which paid a whopping Rs 8,000 crore in taxes to relocate from Singapore to India. CEO Sameer Nigam made it clear: “India is where we started, India is where we are focused, and India is where we will stay for decades.” That kind of commitment signals a major shift in startup thinking. Unlike earlier years when founders felt they had to base themselves abroad to secure funding, today’s ecosystem is equipped with sufficient domestic capital. The Role of Domestic Capital A decade ago, if you were an Indian startup looking for serious capital, you were almost forced to move your domicile abroad to attract global VCs. That’s no longer the case. Siddarth Pai, co-chair at the Indian Venture and Alternate Capital Association (IVCA), highlights how family offices and local VCs are stepping up. “Not just IPO-bound startups, but a whole host of other startups are looking to flip back to India. In regulated sectors, it’s much easier for a company to plan expansion and get approvals when its parent entity is under RBI or SEBI oversight,” he said. The age of startups rushing to incorporate overseas may soon be a relic of the past.

Financial reporting should be about strategic decision-making, not manual data wrangling. Yet, finance teams still spend days pulling data, reconciling numbers, and formatting reports—only to find errors at the last minute. The process is time-consuming, prone to mistakes, and slows down critical business decisions. Robotic Process Automation (RPA) with tools like UI Path is transforming financial reporting. Instead of manually extracting, cleaning, and consolidating data, automation does it for you—accurately, in real time, and without delays. Here’s how it works: ✅ Data is automatically pulled from multiple sources (ERP, CRM, spreadsheets, banks). ✅ Reconciliations happen instantly, reducing errors and improving accuracy. ✅ Reports are generated in minutes—standardized, formatted, and audit-ready. Without automation, finance teams are stuck in reactive mode, spending 80% of their time on report preparation and only 20% on analysis. The result? Slower decision-making, frustrated CFOs, and outdated insights. A company that automated its reporting process cut preparation time by 60%—freeing up finance teams to focus on forecasting, strategy, and real business impact. If your team is still manually preparing reports, you’re already behind. It’s time to automate and turn your finance team into a real-time data powerhouse. 📩 Let’s talk about how RPA can transform your financial reporting. Drop a comment or send me a message if you’re ready to make the shift! #Automation #RPA #FinanceTransformation #CFO #FinancialReporting

My finance team was drowning in manual work, churning out late reports and missing insights. Sound familiar? As a CFO, I turned that chaos into a powerhouse. Here’s how. I joined a firm whose finance crew was stuck in spreadsheet hell. Errors were up, morale was down, and we missed a $500K savings. The fix? One word: automation. We implemented a cloud-based ERP system to streamline reporting. It cut processing time by 30% and freed the team to focus on strategy, like spotting a pricing tweak that boosted margins 5%. The bold insight: a team’s output reflects its systems, not just its people. A 2023 PwC study shows that automated finance teams are 25% more likely to drive strategic wins. Pick one process to automate this month. Start small, maybe with invoice reconciliation, and test a tool. It’s like giving your team a turbo boost. What’s slowing your finance team down? Share in the comments, or tag a leader ready to revamp their systems!

A hard truth about startup growth teams: Being on all sides of the table (operator → investor → board member → full-stack fractional CMO), I've noticed founders often build their growth teams backwards. The typical approach: - Hire specialists for each channel - Focus solely on marketing metrics - Create departmental walls - Chase "best practices" blindly Here's why this fails: - Burns cash 2-3x faster than you gain market understanding - Creates silos that kill early-stage agility - Forces premature channel commitments - Misaligns incentives (vanity metrics vs. real growth) What actually works: 1. Start with strategic alignment - Map company metrics to marketing activities - Build systems for cross-team collaboration - Create clear feedback loops between product and marketing - Focus on scalable processes over hasty campaigns 2. Hire a strategic generalist first - Look for someone who can craft strategy AND execute - Prioritise data-driven decision making over channel expertise - Find people who can teach and enable others - Value business acumen over marketing-only experience 3. Get the foundations right - Deep customer understanding before channel selection - Cross-functional collaboration (marketing + product + sales) - Data infrastructure for measuring true growth (not vanity metrics) - Clear stakeholder communication (drop the marketing jargon) After working with hundreds of startups, here's the truth I keep coming back to: The cost of fixing a poorly structured growth team is always higher than the time it takes to build it right. The most successful founders I work with focus on the bigger picture: Building teams that operate as scalable growth systems. How are you structuring your growth team for scale? ♻️ Found this helpful? Repost to share with your network. ⚡ Want more content like this? Hit follow Maya Moufarek.

Y Combinator Demo Day is just the starting line, not the finish. I've seen too many promising startups hit a wall right after. Don't let that be you. The secret? Brutal focus. Double down on the very things that got you into YC: building a product people obsess over and relentlessly chasing growth. Forget shiny objects and distractions. Resist the urge to get bogged down in "strategic planning" or premature PR stunts. That's fake work. Momentum is the only thing that matters in those early days. Stay lean. Talk to your customers. Iterate like your life depends on it. And for many of you, it does. Keep your investors in the loop—show them you're still hungry. Hold yourself accountable. Build a board that challenges you. Never think you've "made it" too early. The companies that truly crush it are the ones that maintain that Day One intensity, long after the YC confetti settles.

As the founder of a Kolkata-based tech startup, I'm often asked why we haven't moved to Bangalore or Hyderabad yet. While it's true that these cities boast stronger startup ecosystems with greater access to VCs and networking opportunities, we’re in the knowledge economy now. In 2023, the potential to build and scale a startup is no longer confined to geographical boundaries. For India to emerge as a global superpower, we need more than one Bangalore, Delhi or Bombay. What we need is a network of 100 such power cities – each acting as a hub of innovation and growth. It's high time we turn our attention towards unlocking the potential of Tier 2 and Tier 3 cities. Kolkata serves as a case in point. It is India's third-largest city in terms of GDP. Building flutrr here has presented numerous advantages – lower costs for skilled talent, operational expenses, existing network, geographical significance for East India, accessibility to a neglected market. What Kolkata lacks, however, is a vibrant startup ecosystem. This is where companies like ours can drive change. If we want to see India grow into an economic juggernaut, we need to expand beyond the current startup destinations. After all, there are startups in Bangalore without funding, too #startup #entrepreneurship #india #innovation

The Real roadblocks for Entrepreneurs When I first launched my business, I thought the biggest hurdles would be, Technical—figuring out the best strategies, finding clients, scaling up. But the real challenges? They were all in my head. It was fear of failure. Fear of judgment. A nagging voice asking, “Am I really cut out for this?” I’ve found that these mindset barriers are all too common among entrepreneurs. We dream big, but our inner critics get in the way, convincing us we’re not ready, not worthy, or just “not there yet.” Sound familiar? Here’s how I began breaking through: 1. Made mistakes, and that’s okay. 2. Saw setbacks as lessons, not failures. 3. Get clear on your goals, even if the path isn’t perfect. 4. Surround myself with people who uplift and hold me accountable. Every mindset shift takes practice, but each one can be transformative. PS. What mindset barriers are you working to overcome? Let’s share and support each other in the comments! 👇 #Entrepreneurship #Mindset