One of the most common questions I get from early-stage founders is:
“WHEN IS IT TIME TO PITCH??”

Usually shouted, or at least emotionally typed.

It almost always comes after I suggest they prep a bit more before going out to raise. The idea of prep drives some people up the wall. I get it. If you’ve been heads down building something and someone tells you, “You’re not quite ready,” it can feel like a slap. Especially if the clock is ticking.

What they want is a bright red indicator light, something that tells them: Now’s the moment. Go raise.

They want a number. A signal. A clear yes.

But it doesn’t really work like that. Not in practice.

Still, I’ve spent a lot of time thinking about the patterns behind good fundraises and trying to give founders a mental model that’s useful. And over time, I landed on a weirdly simple formula that’s helped explain it better than anything else I’ve used before.

Let’s start there.

A mathematical definition of fundraising success

When it comes to “Am I ready?” or “Will I be successful?” there are multiple factors that can impact the answer. They’re dependent on multiple parties and elements.

But I do believe I’ve been able to distill whether or not you have a chance of getting investment into a simple formula:

In other words, as long as t(g) is greater than t(ti), you have a shot at convincing an investor.

This means nothing unless I define the variables:

• t(g) = Time Given — how much time an investor allows you to spend with them
• t(ti) = Time To Interest — how much time it takes an investor to think what you’re working on is interesting

For the less math-inclined: you want t(g) to be as large as possible, and t(ti) to be as small as possible. This equation is basically a way of thinking about the core dynamic in a pitch.

When someone says no to a fundraise, it’s often not because your idea is bad—it’s because they didn’t get interested fast enough and the meeting ended. The clock ran out before the hook landed. What you want is more time to explain what you're doing than it takes for them to care.

That’s the gap you’re trying to create: t(g) - t(ti) > 0

If you can keep someone engaged long enough for the light bulb to go off, you’ve got a shot. If not, you’re probably walking out with a polite “pass.”

This is easier to see in action, so I’ll walk you through how this showed up for me personally.

A t(g) - t(ti) story

t(g) - t(ti) is a formula I came up with after an “aha” moment I had with a founder. The story will help you understand the dynamics at play here.

I went to a party hosted by a VC friend of mine. This wasn’t a work event at all, but given the social nature of VC investing, many people at the party were investors and founders. While in line for food, a stranger struck up a conversation with me. He made a joke about the amount of food I had piled on my plate (I can’t resist a good food platter). We got to chatting, and it turned out we had a ton of mutual touch-points, including the party’s host, obviously.

He was an entrepreneur with an impressive background and a lot of charisma. I really enjoyed talking with him. At some point in the conversation, he mentioned he had a new startup. His short description made me cringe.“Oof… not something that’s going to do well,” I thought to myself. No matter. I enjoyed hanging out with him, and at the end of the party, he suggested grabbing coffee before he flew back to NYC. I agreed—was looking forward to hanging more in the future.

Three days later, we met up for a morning coffee and struck up an equally compelling conversation. We bounced from personal development to comics to life in NYC and LA. Good times all around.

Early in the conversation, his startup came up. He had a slightly different description from the one he used at the party, but my reaction was the same: “Not a good idea.” About 45 minutes in, as I mentioned something I’d recently read in a book, he replied, “You know… that’s why my startup has such an interesting opportunity.”

And in that moment, I thought to myself, “Huh… that IS interesting.” So, after a 90-minute hang at a party and 45 minutes into a coffee chat three days later… his pitch finally landed. He did what I would consider a terrible job getting me interested in his company. But the amount of time I was willing to spend with him was even longer.

That’s the dynamic I wanted to capture in a formula.

It wasn’t the strength of the pitch that pulled me in—it was how much I liked talking to the guy. I gave him hours before I actually got interested. But that was enough... because he had that gap.

His time to interest was long… but the time I was willing to give was longer.

That’s the core thing this formula is trying to show. Sometimes your story isn’t that tight yet. Or your idea doesn’t click right away. But if you can get someone to want to be around you, they’ll give you more rope. That rope buys you time.

So then the real question becomes: How do you increase the time someone’s willing to give you, or, decrease how long it takes to get them interested?

Optimizing the inputs to t(g) - t(ti)

So let’s break down that story in terms of the formula.

I eventually became interested in the founder’s pitch, but t(ti) was extremely long—it took nearly 3 hours, spread across 4 days, for me to want to learn more. He described his company in a very esoteric way, used a lot of insider terms, wasn’t crisp in explaining the problem or the unique solution, and overall… was long-winded.

But I was willing to spend a lot of time with him. t(g) was extremely long.
The combination of his credibility, shared interests, mutual connections, likability, and charisma kept me in the conversation.

So when it comes to optimizing t(g) - t(ti), here are the things that impact each in the positive:

t(g) – Time Given
Things that increase how much time someone is willing to give you:

• Reputation
• Credibility / Track Record
• Strength of Introduction
• Relationship
• Charisma / Likability
• Testimonials

t(ti) – Time to Interest
Things that reduce the time it takes for someone to care:

• Crispness of Story
• Quality of Deck
• Compelling Data / Traction / Progress
• Momentum
• FOMO

None of this is revolutionary—but putting it in this frame helps you see where the levers are. If people aren’t leaning in yet, figure out whether you have a t(g) problem or a t(ti) problem.

Are you not getting enough time with people? Or is the time you’re getting not converting into curiosity?

Once you know which side is off… you can actually work on it.

A sign that t(g) - t(ti) > 0

The most compelling way to begin a fundraise is to be pulled in by investors.

This approach lets you stay focused on building your company while investors learn about your progress along the way. Say you meet a few investors outside of an active fundraise, describe what you’re building, and mention the milestones you're working toward. The interested ones will stay close. As they see you hit those milestones, they’ll lean in. They’ll want to have more conversations—often initiating those meetings themselves.

Of course, not everyone has the flexibility to wait for interest to come to them. But it should be clear in this situation that t(g) - t(ti) > 0. Understanding that ideal helps you work toward a personal setup where you're as close to that dynamic as possible—before your own timelines require you to formally kick off the fundraise.

That’s my technical walkthrough of “Am I ready to pitch?”

For the math nerds out there, I hope it helped. Let me know if you have any questions!

Be chased,
Jason