Essay 01 · 4 min read
How a VC decides whether to take a meeting.
Before anyone reads your full deck, a much smaller, faster filter runs first: does this fit the fund at all? An analyst or associate scanning inbound deal flow is usually asking three quick questions in the first 30 seconds — right stage, right sector (or clearly sector-agnostic), and is there any signal of quality (a specific number, a notable early customer, a sharp one-line pitch) versus generic language.
This is why so much of the advice about cold emails converges on the same point: lead with the specific thing that would make a busy person's filter say "keep reading" instead of "pass." A vague opening line does the filter's job for it — in the wrong direction.
Once past that first filter, the decision to actually take a meeting is really a bet on your own time versus the odds this becomes something. A fund that takes 30 first meetings a month and invests in 2 companies a year is making that trade-off constantly — a fast "yes" to a meeting is cheap for them; a slow, generic pitch that wastes it is not.
Practical takeaway — Your first email or intro isn't trying to convince someone to invest. It's trying to survive a 30-second filter. Optimize for that specifically, separately from the deck itself.
Essay 02 · 5 min read
Why VCs ask "Why now?"
Almost every VC, at some point in a pitch, asks a version of "why hasn't this been done before, and why is now the right moment?" It can feel like a gotcha question, but it's actually one of the most useful diligence questions in the entire process, because it forces a founder to locate their company inside a real trend rather than a timeless idea.
Good ideas that are ahead of their moment fail just as often as bad ideas — a product that needs infrastructure, behavior change, or regulation that doesn't exist yet can be right and still be unfundable today. "Why now" is really asking: what changed recently — a cost curve, a new platform, a regulatory shift, a behavior shift — that makes this newly possible or newly urgent?
A founder who can point to a specific, recent, external shift (falling compute costs, a new API, a post-pandemic behavior change, a new regulation) is showing they understand market timing, not just their own product. A founder who answers with "the market is just ready" is giving the investor nothing to underwrite.
Practical takeaway — Have a specific, external, dateable answer to "why now" ready before you ever get asked — it's one of the highest-leverage sentences in your entire pitch.
Essay 03 · 5 min read
What makes a startup "venture-backable."
This phrase confuses a lot of founders because it sounds like a judgment on whether your company is good. It usually isn't — it's a judgment on whether your company's potential ceiling fits the math a VC fund needs. A profitable, well-run business that will plausibly reach $20M in revenue and stay there is a genuinely good business. It is often not venture-backable, because it can't return a fund on its own (see: Power Law).
What VCs are actually screening for is whether a company has a plausible, if uncertain, path to a very large outcome — usually meaning a market big enough, a business model with real operating leverage (revenue can scale faster than costs), and some structural advantage (network effects, data, distribution, switching costs) that lets it defend that scale once reached.
This is also why "not venture-backable" isn't an insult — plenty of excellent businesses are simply the wrong shape for this specific type of capital, and are far better served by revenue-based financing, a small angel round, or no outside capital at all.
Practical takeaway — Before pitching VCs, honestly stress-test whether your business needs to be venture-scale to be worth building — the answer changes who you should actually be raising from.
Essay 04 · 5 min read
Why VCs reject startups (and why most rejections aren't about you).
Given how the funnel actually works — a fund seeing thousands of opportunities a year and funding a tiny handful — most rejections have nothing to do with whether your company is a good business. Common, unglamorous reasons include: wrong stage for that fund, wrong sector for that fund's current thesis, a portfolio conflict (they already backed a competitor), a partner who's already at capacity on new boards, or simply timing — they saw you before you had the traction to make the case, and by the time you do, you've stopped following up.
The harder, real rejections are usually one of a few patterns: the market genuinely doesn't look big enough once modeled bottom-up, the team lacks a specific, relevant edge for this exact problem, the traction doesn't show the underlying growth is durable, or the "why now" story doesn't hold up under a few follow-up questions.
Investors rarely explain which of these it was — a generic "not a fit right now" covers both a genuine pass on the business and a fund-level mismatch that had nothing to do with your pitch. This ambiguity is frustrating but also useful to internalize: a string of "no"s is data, but it's noisy data, and over-updating on any single rejection is a mistake in both directions.
Practical takeaway — After a rejection, if you can get even one specific, honest reason, treat it as gold — it's rarer than the rejection itself, and worth directly asking for.