NYC Founders & Operators: Managing Your Calendar as a Founder | Upcoming Events

This Week: Launching Our New Membership Program, Managing Your Calendar as a Founder, and Upcoming NYC Events.

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Calendar discipline is one of the highest-leverage things a founder controls. Your schedule is your strategy, and how you spend your time will determine your success or failure.

In my recent conversations with founders, I keep hearing the same thing: their week is packed, they are behind on everything, and they have not had time to think. When I ask what consumed the week, the answer is usually some combination of networking and fundraising, or too much time spent in meetings. These can be valuable. They can also become sophisticated forms of procrastination. Here is how I manage my own calendar and where I most often see founders lose time.

Leak 1: Indiscriminate networking

Founder dinners, panels, coffees, and community events can create valuable relationships and perspective. They give you signal on what other founders are seeing. They give you a break and expand your perspective, which can be valuable.

But they are not in the same category as business development, recruiting, fundraising, or product work. They do not replace the ten cold emails you did not send this morning because you were up late at dinner the night before. The founder calendar is a zero-sum object. Time spent meeting other founders is time not spent meeting prospects, recruits, or investors who could meaningfully move your business forward this quarter.

I run an events-based community, and I still tell founders to be selective about the events they attend, including ours. The best founders I know show up to one or two carefully chosen touchpoints a month and put the rest of their calendar toward people and work that will move the needle.

Leak 2: Fundraising before you’re ready

Founders often start investor conversations before reaching the milestones they need to unlock investor interest. They burn through warm introductions while the company is not ready, and their story is not yet compelling enough. The time they’re spending in investor conversations is time they’re spending away from the areas that they should actually be focusing on at this stage: executing on growth, product, or hiring.

The winning approach is to be strategic. Heads-down building comes first. This will unlock real traction. Once you have that foundation, investor conversations will convert with much less time and effort, at better terms.

Leak 3: The 30-minute/60-minute meeting default

My default meetings these days are 15 minutes. Some meetings run over. Some warrant a longer call. But in many cases, 15 minutes will be enough to discuss and align. It may not be the right default for everyone, but I challenge you to experiment with 15 or 30-minute meetings. They’re sufficient more often than you’d expect.

The Fix: Weekly Calendar Audits

At the end of every week I run a short review. What did I want to accomplish, what did I finish, and what got in the way. Then I look at my calendar with a critical eye. The question is simple: What did I actually get done this week? If the answer is ‘less than I wanted’, the reason is likely in my calendar. If I lost focus time because of how I set up the week, that is what I fix for the next one. Done consistently, this is how I build the schedule I actually want, one adjustment at a time.

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See you soon,

Stephan