Most founders don’t realize how wide that gap is until after the wire hits.

When I launched dot.LA, we built a cross-firm cap table that gave me a front-row seat to how different VCs actually operate after the wire transfer cleared. It was typically a smaller-than-usual check size for the investor, but I got a unique lens on who really showed up. Some just wanted quarterly updates, which were often ghosted. Others made a point of proactively reaching out and offering ideas and support whenever possible.

Now, two years into the investor seat myself, I’ve also seen that spectrum from the inside. And what I’ve learned is that real support looks less like a dashboard review and more like this:

• Structured, recurring convos that aren’t just about “how it’s going,” but about where to step in

• Hands-on help with recruiting, GTM planning, and downstream fundraising that is systematized but bespoke

• A portfolio community where founders solve problems faster because they’re not solving them alone

• Systems that scale this support without diluting it: async tools, modular platforms, on-demand experts

And at the core, there’s a mindset: this is a relationship. It’s not “call me if you need me.” It’s “I’m already here.”

If you’re a founder picking a lead, don’t just ask who they’ve backed; ask how they show up.

If you’re a VC, ask whether you’re the kind of partner you’d want in your own corner.

That’s been my north star on the other side of the table: be the VC I wish I’d had — the one I glimpsed in pieces across the best of them.

If you’re still pre-PMF, your go-to-market motion should look simple: the founder sells. Not because you’re the best closer, but because no one else can extract the signal you need. Every sales call is a product conversation. Every objection is a roadmap. If you’re not close to the buyer, you’re not close to the problem.

That doesn’t mean you’re flying solo. One of the most useful early hires is a gritty, curious BDR: someone who can run outbound, fill the funnel, and get you in the room. But if you’re still figuring out your ICP, testing segments, or sharpening the pitch, you shouldn’t be handing off the conversation. You need those reps yourself.

The sequencing I recommend looks like this:

→ First: Founder-Led Sales.

Run the calls. Track conversion. Sharpen your narrative.

→ Then: Outbound BDR.

Once you’ve got a rough playbook, bring someone in to build lists, test scripts, and learn what’s working.

→ Only Later: Account Execs.

When you’re swamped with qualified leads and your calendar is full, bring in a closer to help scale.

→ Eventually: Sales Leadership.

A VP makes sense once you’re past $1–2M ARR and need to manage a team, but usually not before.

The mistake I see over and over is hiring too early. Senior salespeople are expensive, but more importantly, they’re not wired for this stage. They expect structure. They want process. And if you don’t have real signal yet, they’ll either stall out or, worse, start chasing the wrong leads.

Founder-led sales is about earning clarity, so that when you do hire, you’re handing over a system, not a mess.

I’ve seen this sequence work firsthand across multiple early-stage teams. The founders who stay closest to the buyer win faster. They don’t just close deals, they learn what they’re really selling.

If you’re figuring that out right now, keep going. The next hire can wait.

It’s not a cop-out. It’s a reflection of how slippery PMF can be in practice, and how founders often try to codify something that’s more diagnostic than definitional.

• There are patterns, though. When you’re close to product-market fit:

• You don’t need to brute-force the top of the funnel with mass outbound.

• Sales cycles compress, feedback loops tighten.

• Buyer personas stop needing nudges and start championing internally, because the solution actually solves something real.

Instead of dragging leads over the line, you find yourself catching up to inbound. The questions change from “why do we need this?” to “why didn’t someone build this sooner?”

Or as Marc Andreessen put it: “The market pulls the product out of your hands.”

That’s the moment I most enjoy with companies: when they’re right on the cusp. Some traction, yes, but still messy enough that support actually matters.

Most of the founders I back are solving real problems. Pain pills, not vitamins. They’re building for customers who really, actually need the product, not just admire it conceptually. And when that’s true, the signals are there if you know what to look for. You’ll see usage patterns that defy your initial assumptions. You’ll lose a deal and still get a thank-you note. You’ll wake up to a calendar full of prospects who found you.

But getting to that point requires discipline. I’ve seen companies stall for quarters because they couldn’t stop selling the version of the pitch they wanted to be true, rather than the one the market was reacting to. The best founders I’ve worked with treat GTM as a discovery process. They adjust the frame until it snaps into place.

That doesn’t mean chasing every shiny logo, especially if that prospect would require some large custom build-out that isn’t universally applicable. It means having enough clarity to recognize what’s working, and enough conviction to focus there, and iterating until you feel the subtle infection point.

So if you’re wondering whether you’ve found product-market fit, ask yourself this:

• Are prospects repeating your value prop back to you in their own words?

• Are you closing faster than before, without steep discounts or heroics?

• Are users showing up without needing to be reminded?

• Are you hearing “this is exactly what we needed” more than “we’ll think about it”?

Want a metric? Sean Ellis’s 40% test is a good one: if you survey your users and 40%+ say they’d be ‘very disappointed’ if the product disappeared, you’re probably in the zone.

It’s not scientific. It’s not even linear. But when it clicks, it clicks. That’s the moment to double down: lock the narrative, focus the roadmap, and pull the team into alignment. Don’t chase every shiny use case. Don’t overhire. Just feed what’s already working, and clear everything else out of the way.

I’ve seen that moment up close, with teams solving real problems for customers who can’t wait. It’s what I look for now when meeting early-stage founders. You can’t fake it. But if you’re close, you can usually feel it.

And like Justice Stewart said: you know it when you see it.