His real point is that isolation traps you with your own inner monologue. Agassi would know. He spent an entire career winning at a game he has said he hated “with a dark and secret passion.”

I am the runner he waves off. And for most of the last five years, he was right about me, just not in the way he meant.

What the solitude cost me was not company. It was an accurate picture of myself.

When the work is solitary, the map in your head slowly stops matching the territory under your feet, and you are usually the last to know, because you are the one holding the map.

I came back to running about a year into the pandemic, when the isolation had ground me down and I had stopped taking care of myself. I signed up for the Malibu Half Marathon to force some structure back into my weeks, and it worked better than I had any right to expect. By that fall I had quit drinking, lost twenty pounds, and finished the race.

The discipline stayed. Fifty to seventy miles a week, usually before dawn, became the scaffolding under everything else: marriage, the sale of the company I had built, and eventually the start of my own fund and advisory practice. I also went from a decent runner to a genuinely good one. I broke three hours in the marathon, qualified for Boston, and then cut another ten minutes off the time.

Almost all of it happened alone. Running was solitary. So was building a company, even with a co-founder. So is running a fund as a team of one. When a marathon build was already consuming so much of my time outside of work, I did not want to spend my limited social hours driving across the city for group runs. So I rolled out of bed and ground out loops around my neighborhood by myself, just me and an audiobook and the inner monologue Agassi was talking about, the voice that on bad mornings sounds a lot less like a coach and a lot more like a prosecutor.

A few months ago I finally joined a run club, a Wednesday night track workout under the lights with about a hundred people of every level. I had always written off run clubs as either glorified dating clubs or workouts for semi-pros, and I am not sure which I was more afraid of.

What I found instead was a mirror.

I was not the fastest person there, but I could run with the fast group without much trouble, and I could push harder in the 400-meter repeats than I had ever managed on my own. The part that actually rearranged something in my head was the warmup. For years I had treated ten-minute miles as my easy pace, because that was true back in 2020.

Jogging the warmups and cooldowns with the group at eight- and nine-minute pace felt like nothing.

It was not that I had suddenly gotten faster that night. The fitness had been there for months. I just had no way to see it while I was running alone. I had been carrying a five-year-old picture of myself and calling it the truth.

That is the trap of doing hard things in isolation. The same discipline that lets you get good at something alone is the thing that hides how good you have gotten. You put your head down and do the work for years, and because no one is beside you keeping score, your estimate of yourself quietly stops updating.

The people most capable of achieving hard things in isolation are often the ones running on the most out-of-date information about themselves.

So we wait. We tell ourselves we will have arrived once the round closes or the whale customer signs or the next milestone certifies the person we are trying to become. But sometimes we passed that point a while ago and never noticed. It is almost the inverse of “fake it till you make it.” We are not pretending to be something we are not. We are refusing to notice we already are.

I have done this my whole career. When I was running my last company, I did not count myself as a CEO, even while I was managing a team and raising money. When I started writing angel checks, I did not count myself as an investor. When I launched my fund, I was still operating off the self-image of someone trying to figure out how funds work.

None of that was modesty. It was stale information. Other people had updated their read on me years before I updated mine, and my easy pace was eight-minute miles long before I let myself run them.

I see the same lag in nearly every founder I work with. Not long ago I spent a few weeks with a first-time CEO building software for one of those sleepy, paperwork-heavy industries nobody disrupts because it is genuinely hard. He had a real product, a couple of paying customers, and one specific type of customer he could win again and again.

But every time we talked, he pulled toward a bigger, shinier, untapped segment, convinced the real prize was out in the territory he had not reached yet. He was still the founder who had to push in every direction at once and personally touch everything, when the business had quietly become something steadier than that.

The thing already working was the business, and he could not see it, because seeing it meant admitting he was further along than his picture of himself allowed. Most days, my job is just to be the mirror that shows a founder which part of the map has gone out of date.

You still have to do the work alone. But solitary work quietly erodes your ability to calibrate, and at some point you need something outside your own head to tell you where you actually stand.

Sometimes that is a coach or a peer. Sometimes it is a hundred strangers on a track on a Wednesday night.

So check your map. The danger is not that you are incapable of the thing in front of you. The danger is that you are navigating by an old version of yourself, a picture drawn years ago and never revised, and you cannot redraw it entirely from the inside.

Put yourself somewhere your assumptions get measured against other people: a track, a dinner table, a pitch meeting. Not to become someone new, but to find out, faster than you ever could alone, where you already stand.

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.