Timing and Capital - What your spreadsheets can't tell you

Two things about Venture Capital nobody talks about enough

Venture capital looks magical from the outside. Billion-dollar exits. Founder stories splashed across the media. Returns that make public markets look boring. But finding these outliers early? It’s like finding a needle in a haystack. As Nithin often says, and he’s right.

Ask any seasoned investor what makes a good venture bet, and you’ll hear the usual suspects. Massive market size, exceptional team, innovative product, fanatical customer love, and defensible moats.

All of these matter. But not as much as two things that rarely top the list - timing and the ability to continuously raise capital.

Why timing trumps almost everything

Consider an example. A startup has assembled the perfect team. The product is elegant. They’ve raised a solid seed round. But if they launch at the wrong moment, when customers aren’t ready, when the technology hasn’t matured, when economic conditions are bad, none of it matters.

No customers means no revenue. No revenue means burning through that seed capital. And seed capital, however generous, runs out.

The AI graveyard of 2017-2018 tells this story perfectly. Dozens of well-funded AI companies with legitimately smart founders built products too early. The models weren’t good enough. The compute was too expensive. The market wasn’t educated. Most died quietly.

But the handful that survived, that found believers willing to fund them through the tough years, got to ride the ChatGPT moment in 2023. Same founders, similar ideas, completely different outcome. The only variable? Timing.

Or look at video conferencing. Zoom wasn’t the first player, not even close. WebEx had been around since the 1990s. But Zoom launched when bandwidth was cheap and reliable, when remote work was becoming normal (even before the pandemic), when enterprise software was finally expected to be beautiful and easy to use. The timing was perfect.

Look at Razorpay. Harshil Mathur and Shashank Kumar were rejected by every major VC in India in 2014. The pitch was simple. Make online payments easy for small businesses. Everyone said the market was too small, that PayU and CCAvenue had already won. They got into Y Combinator, raised a tiny seed round, and kept at it. By 2015, UPI was announced. By 2016, demonetization hit. Suddenly, their timing was perfect. The same VCs who passed came back. That persistence through rejection, that ability to survive until the market caught up, that’s what turned Razorpay into a company worth billions.

Or PhonePe. It launched in 2015, right when digital payments were just noise. The Flipkart acquisition in 2016 seemed like an acqui-hire. Then demonetization hit in late 2016. UPI launched properly in 2016-2017. Suddenly PhonePe was in the perfect position. They scaled from almost nothing to India’s largest UPI platform. Same team, same product idea, but launched exactly when India was ready for it. Paytm was bigger and better funded, but PhonePe’s timing on UPI was perfect.

Meanwhile, Tesla, which started around the same time, survived long enough (barely) to see the market mature. Same industry, same era, different timing choices, completely different outcomes.

The fundraising ability nobody models

Here’s the uncomfortable truth. Most successful startups need multiple rounds of capital. Often many more than anyone planned for.

The ability to keep raising money, to find new backers when the previous check is running low, to convince investors during down markets, to change the story when the original thesis isn’t working, this skill is seriously underrated.

I’ve seen brilliant teams with genuine traction fail because they couldn’t raise their next round. Maybe the market turned. Maybe their numbers weren’t venture-scale enough. Maybe they just weren’t good storytellers. It almost doesn’t matter why. No capital means game over, regardless of how good the business might have been.

On the other hand, I’ve watched companies that seemed to be constantly figuring it out to keep raising rounds. Not because they had product-market fit, but because the founders were exceptional at fundraising. Some eventually found their way. Many didn’t. But they all got more chances than their peers who couldn’t keep capital flowing.

This isn’t saying that fundraising velocity is good. It’s recognizing that runway equals options. And in venture, options mean survival.

Look at Airbnb. They were rejected by investors repeatedly in 2008 and 2009. They sold cereal boxes to stay alive. But Brian Chesky kept pitching, kept refining the story, kept finding believers. By 2011, they raised a proper Series B. That ability to persist and fundraise through rejection saved the company.

Or take Freshworks. Girish Mathrubootham was rejected by Indian VCs in 2010-2011. They said SaaS doesn’t work from India, that customers won’t pay, that Zendesk had already won. He raised from Accel (through their US team), kept the burn low, focused obsessively on customer love. By 2014, the model was proven. By 2021, Freshworks IPO’d. Those early rejections forced discipline. The ability to find believers outside India when the local market didn’t get it, that saved the company.

Or look at Meesho. Vidit Aatrey and Sanjeev Barnwal started in 2015 as a platform for small resellers. For years, investors didn’t get it. The model seemed too complicated. Why not just be another e-commerce site? They kept pitching the reseller angle, kept refining. By 2019-2020, when social commerce was exploding, suddenly everyone understood. They raised massive rounds from Facebook, Softbank. That persistence in telling a story nobody believed initially, that’s what built a company now valued at $5 billion.

Then there’s Postman. Abhinav Asthana built it as a side project in 2012. For years, it was free, just developers sharing tools. Investors said there’s no business model, that developer tools don’t make money in India. He kept building, kept the community growing. By 2016, the API economy was exploding globally. By 2021, Postman raised at a $5.6 billion valuation. That ability to build for years without pressure to monetize immediately, to wait for the market to mature, that patience created enormous value.

Or consider Stripe. Patrick and John Collison were so good at building relationships with investors that they had term sheets from multiple top-tier VCs before they even had a product. That network gave them room to build without pressure, to iterate without panic.

What this means for you as an analyst

If you’re building your pattern recognition as a VC analyst, add these to your checklist,

Timing: Is the market pulling or are you pushing? Are you having to convince customers this problem exists, or are they already searching for solutions? Are the economic, technological, and social conditions aligned?

Ask yourself what needs to be true about the world for this to work? Is that true now, or will it be true soon? Can you see the path clearly?

Sometimes the answer is “not yet,” and that’s okay if the trajectory is obvious. But “not yet” requires exceptional founders who can survive until “now” arrives.

Fundraising ability: Watch how founders tell their story. Do they understand their numbers? Can they explain why now in a way that makes you lean forward? Have they built relationships with other investors, even if they’re not raising? Do they have advisors who actually open doors, not just lend their names?

The best founders are always fundraising, not because they’re desperate, but because they’re building options.

Pay attention to how they handle your questions. Do they get defensive or do they engage? Do they admit what they don’t know? Investors remember these interactions. The founders who leave a good impression, even when you pass, are the ones who can come back later and still get meetings.

The spreadsheets won’t tell you this

You can model TAM until your eyes glaze over. You can score teams on frameworks. You can stress-test unit economics across a dozen scenarios.

But if you’re not asking “Is this the right moment?” and “Can these founders keep the capital engine running?", you’re missing two of the biggest drivers of outcomes.

The graveyard of venture capital is full of companies with the right idea at the wrong time, and great businesses that simply ran out of money.

The best investments? Right idea, right time, with founders who know how to keep the lights on long enough to win.

Final thoughts on pattern recognition

Early in your career, you’ll see investments that seem obviously good fail for reasons that don’t appear in the IC memo. You’ll see investments that seemed marginal turn into home runs because something shifted at just the right moment.

Pay attention to these moments. They’re not random. They’re usually about timing or capital, or both.

The framework everyone teaches you (TAM, team, product, traction) is necessary but not sufficient. It’s table stakes. The real edge comes from developing intuition about when the world is ready for an idea, and whether the founders can survive long enough to be there when it is.

That intuition doesn’t come from spreadsheets. It comes from watching companies over time, from seeing which ones adapt and which ones don’t, from noticing who can raise in tough markets and who can’t.

Build that muscle. It matters more than most people admit.

That’s the game.