Does Your Calendar Reflect Your Strategy?
This is Going to Big Big is written since 2004 by Charlie O’Donnell, former VC and current coach to active and aspiring venture professionals and professional pitch deck skeptic.
One of the lessons I’ve learned over two decades in venture—one I genuinely regret not internalizing earlier—is that I spent far too long trying to meet everyone.
In this industry, the more you put yourself out there, the more the world pushes back with opportunities. A blog post hits, a tweet goes viral, you speak at a conference—and suddenly you're inundated. Founders, operators, students, service providers, “Let me show you want I’m working on” DMs. It becomes an unending parade of people you could talk to.
And the mistake most VCs make—especially early in their careers—is confusing volume with progress. Just because you’re taking all the meetings doesn’t mean you’re closer to finding the next big thing.
It’s the same magical thinking as a baseball player believing they could, in theory, hit a home run on any pitch. Sure—anything could happen. But that’s not how plate discipline works. Some pitches are simply more hittable. Some have a massively higher probability of leaving the park.
The real question is: are you structuring your calendar around the pitches that give you the highest probability of success?
Who Asked for Those Meetings?
Try this simple diagnostic:
How many meetings on your calendar this week are there because someone asked you…
versus because you asked them?
If you’re honest, the ratio is probably not where you want it to be.
Inbound meetings are easy.
- They’re flattering.
- They’re available.
- Take enough of them and they will probably pull you toward the median.
Outbound meetings—the ones you initiate—tend to come from intention.
- They reflect curiosity, hypothesis, and strategy.
- They represent people you believe have:
better-than-average networks
better-than-average chances of success
domain expertise you can’t get anywhere else
or simply a track record that skews outcomes upward
Those are top-quartile meetings. And top-quartile meetings are what drive top-quartile fund performance.
VC Time Is Finite. Meeting Quality Is Not.
This business has a built-in illusion: more meetings = more shots on goal. But in reality, you don’t have infinite shots. You have finite hours.
Every meeting you take displaces another one you could have taken—or one you could have proactively sought out.
Start scoring your meetings the same way you score anything else:
Did this meeting have a better than average chance of resulting in a high-quality opportunity?
Did it move your thesis forward?
Did it expose you to real insight rather than generic “spray and pray” ideation?
Was this the best possible use of that hour compared to the meetings you could have sourced?
If not, that hour was expensive.
Take a concrete example.
Who would you rather take your next meeting with?
A cold inbound from a random founder who “invented a new payment solution” coming out of their Harvard MBA program that has a consulting background, or…
The most interesting person you could find in a list of early Stripe alumni—people who have lived inside one of the highest-leverage fintech ecosystems on the planet, who know where the bodies are buried, who understand the infrastructure gaps, who have seen world-class execution firsthand.
Which path gives you a higher likelihood of finding an extraordinary founder doing something truly new? Who is more likely to both identify a legitimate opportunity and attract the talent to go after it? Someone who has the Ivy credentials or someone who could name ten people they worked with at a generational fintech company they’d hire the day the funding closed?
Even if that Stripe alum isn't starting something new, she might be a great co-founder to that recent business school grad who decided they wanted to be a founder before they sought out a problem to solve.
The call to selectivity might sound like gatekeeping, but I would argue that being more intentional about your calendar increases selectivity. Instead of just relying on the kinds of inbound your existing network happens to put in front of you—and given that our networks tend to look both physically and on a resume quite like ourselves, you know that that means—investors should be more thoughtful about who winds up on their calendar.
The Risk of Overcorrecting
This advice can sound like a call to narrow too early. That’s not what I’m arguing. Early exposure is how you develop taste and judgment — focus just ensures that exposure compounds instead of diffusing.
Refactor
Stop believing you’re “missing out” by not taking every meeting. You’re actually missing out by taking too many of them—because they crowd out the high-probability conversations.
Your calendar is not a to-do list.
- It’s an asset allocation.
- It’s exposure management.
- It’s a statement of your strategy.
If you want better outcomes, you need better meetings. And better meetings come from focus, not volume.
I suggested to one of my coaching clients that they cancel the worst meeting on their calendar every week--the one where they're the least excited to meet the founders, and replace it with someone from a list of formerly exited founders in the spaces she cared about.
Within a month, she had a lead on her first deal from those latter meetings.
Refactor your calendar.
- Shift the ratio from inbound to intentional.
- Stack your time with people who genuinely increase your chance of success--that you're really excited to meet.
The biggest unlock isn’t finding more founders. It’s finding the right founders—and making sure you actually have time for them.
Have a rubric for what gets a meeting from you—relevance to your thesis, potential for learning, or perhaps the source.
Who has leant their creditability to this intro and do they lend it sparingly or widely?
Some folks might worry that cancelling a meeting or saying no to an intro might be rude. In my experience, leaning on respect for the other person’s time is always the way to go. If you don’t have the right level of enthusiasm or interest in a meeting, it’s actually best that you give someone their time back.
Along the same lines, I often deflect introductions with a thoughtfully written e-mail that, while it takes me a few minutes to write, takes me far less time than a full meeting would have taken.
Without intention, especially as a venture investor, your time budget will quickly run out and you’ll be left wondering why everyone else seems so much better prepared to find that next big opportunity even though you’ve all been working equally hard.