This week, I’ve been thinking about productivity, maintaining friendships, and meal prepping.

Questions

Business

What does my day-to-day work look like as the CEO of an early-stage AI startup? How can I improve my day-to-day productivity?

In 2022, one of my Harvard classmates who founded a media startup, faced some backlash after posting a Twitter thread about the ‘work she actually does in a day’.

People described it as ‘15 minutes of work stretched out over a day.’

I recognized it for something else: The work of a CEO is often nebulous, requires frequent context-switching, and sometimes has amorphous metrics attached to it.

When Yehong described some of the things that took up her time in that slice-of-life Twitter thread—poring over designs, responding to journalists, and reviewing marketing materials—I felt sympathy for her in trying to describe the job of a CEO.

Somebody else in my network had a different description for the job: “As a business builder, my job is to build and maintain a well-oiled machine - But I can't personally be a critical piece of that machine.”

My day-to-day can sometimes feel like ‘15 minutes of work stretched out over a day,’ even to myself. But that’s (usually) an illusion based on the specific deliverables of that day, and the illusion is misleading because it ignores the invisible work that goes into it.

Let’s take a step back — at the end of the day, what am I focused on for my business? It always comes down to two things: Capital and customers. Every single thing a business owner does should drive the needle forward in one or both of those areas.

Now let’s dive deeper into what goes into each of those, and some of the visible and invisible work I do to drive those forward. (Spoiler: A lot of the visible work is emails and slide decks, and a lot of the invisible work is meetings and phone calls).

Capital

Capital is about two things, money in and money out. Lately, my attention has been focused largely on capital.

Money in: Have the invoices been paid? How can I drive more investment to the company?

Visible work: The invoices need reminders sent. Fundraising demands writing investment memos, designing slide decks, and sending emails.

Invisible work: My cofounder and I have spent between 5 and 10 hours this past month on the phone with each other, debating the phrasing on this slide, or arguing about whether one graphic or statistic gets the point across better than a different option. (That’s outside of the time we spent working on it asynchronously)

I’ve described our most recent deck as ‘Version 40,’ and I think that’s in the ballpark of accurate. Why so many versions? The product changed, the market changed, the messaging changed, etc.

The work compounds and culminates with sending investors messages/emails and meeting with them. What this actually looks like most days is a lot of time on LinkedIn, looking for different routes to introductions, sending follow-up messages, or asking for introductions. And spending time on LinkedIn often feels like, and sometimes is, a waste of time.

Money out: What bills are due? How much runway do we have left? What can we do to cut expenses?

Our biggest expense right now is development/engineering work.

Cutting expenses is always a priority, although this past month my cofounder and I had a conversation about migrating from OpenAI’s native API calls (where we recently ran out of credits) to Azure OpenAI (where we still have credits) to save money, and my cofounder reminded me that the development hours it would take to make the migration would end up being more expensive than paying for OpenAI usage for ~2 months at our current usage.

Customers

This area comes down to acquisition and retention.

Acquisition: What can we do to get relevant messages in front of the right people? What can we do to make the onboarding experience smoother?

Since we’ve been focused on executing our current pilots, acquisition has mostly taken a back seat recently. But I know once we finish out this SPV fundraise, my attention will return to customer acquisition.

Retention: What can we do to provide more value to our customers?

We’re meeting regularly with our pilot customers to talk to them and get their feedback. Right now, we’re still relatively early in the pilots (thanks, Holidays), and that’s about as much as we can do.

As their usage increases, we’ll monitor for trends in usage and check in more regularly. Right now, we have a small enough cohort of pilot customers that my cofounder and I can keep our ear to the ground for each one.

How can I improve my day-to-day productivity?

I want to timebox more of my schedule and limit context-switching as much as possible.

This week, I plan to choose one activity to do for a set period of time, and turn off notifications, sit down, and do that activity. This could be writing a guest post for a sales blog (which has slipped down my to-do list from 2023), cycling through the investors we’ve talked to with personalized outreach about the SPV, or searching for net new investors to approach about the SPV.

Even as I write this goal down, I recognize it’s inherently hard to turn off notifications for the activities that live in distraction zones (email, LinkedIn). But, I don’t think there’s a good way around that.

Personal

How do I stay connected to my friends in different places?

I have more friends outside of the Bay than in it, and even in the Bay, my friends are spread out.

Lately, I’ve been missing the serendipitous moments in college when I would look around and see almost all of my friends in a single room.

I wish I had a magic solution, or that all of my friends decided to move to the Bay Area, but I do have two ideas I’m planning on trying out.

1) Scheduled phone calls

This isn’t an earth-shattering idea — it’s easier to stay connected to people if you’re intentional about when and how often you talk to them. But I’ve always struggled to call people out of the blue when I don’t have anything ‘important’ going on.

Some people I know call their friends every few days, no matter what’s going on. And based on my limited observation, it seems like this is more common among women than men.

So a friend and I have a calendar event — yes a calendar event — to check in every week. We haven’t kept it perfectly, but it’s good to know that we plan to talk every week.

2) Games/projects

I’ve always found it easier to keep in touch with folks when we are either playing the same game or working on the same project.

So when a friend got laid off a few weeks ago and asked me to advise him on the ‘12 startups in 12 months’ goal, I agreed — now we’d have a reason to talk frequently, and we’d have something to talk about.

Misc.

What’s a simple way to get started with meal prepping?

When I had planned this question for myself to answer in this newsletter, I was planning on being home for most of this week. Instead, I stayed on housesitting for my friend in Berkeley, and I didn’t see a point to meal prepping here when I’d only be here for a few more days (sorry, Nica).

But I had done some thinking about how I’d approach it. I would cook a large portion of meat, some grains, and some vegetables, and either buy or cook a few different sauces. Then I’d mix and match.

The trick being, the meat probably can’t be seasoned very much at all in case the seasoning works against one of the sauces. So I’d probably boil a few pounds of chicken, cut them into strips or bites, and then use the various sauces to season them, and mix them with the grain and veggies.

Because I’m a nerd, I made a custom GPT to help me meal prep. Maybe you’d be interested in trying it out?

Quote

Reflection

There are a lot of competing demands on people’s time, and as I think about the improvements I want to make in my life it can feel overwhelming.

To name a few: Exercising, eating healthier, making money, being social, getting enough sleep, and writing/reading.

The advice I’ve been given — prioritize and rotate — seems to contradict with my belief that the only way to see recognizable improvements is with consistency and routine.

Priotize and rotate means to pick 1-2 of the options and focus on those for the week. Then pick another 1-2 and focus on those the next week. And so on.

But with things like exercising and eating healthy, you can’t just ignore them for a week or two and expect to pick back up where you left off, or to notice any improvements.

It seems like I probably need to do something like prioritize exercising every week and rotate out from the rest.

This week I’ve been reflecting on how incremental improvements in one area of life, like exercising & health, can carry over and improve overall quality of life. It seems counterintuitive because it feels like I need to make consistent progress on all of these areas. That feeling is very strong — that I will feel unfulfilled if I don’t work on everything.

But what ends up happening is that there’s a stronger sense of overwhelm if I feel pressure to do everything, and then I end up doing nothing.

So I need to believe that improving my exercise habits will raise my overall quality of life, even if in the short term it means I’m less fulfilled or believe I’ll be less fulfilled in areas like being social.

(These two are especially at odds because I don’t live close to many friends, so to be social usually means a 60-90 minute drive, which makes it hard to exercise on the same day I’m social and vice-versa).

The alternative is to accept less exercise more consistently, even if that means just 10 minutes on the days I’m social and need to drive 2-3 hours to do so.

The reality is probably that any positive momentum in any of these areas will raise my quality of life, that consistency is better than infrequent intensity, and that I should feel less pressure to make positive momentum in every area every week.

Qs for Next Week's Newsletter

Business

How has fundraising been going?

Personal

What advice do you have for someone who struggles to consistently drink enough water?

Misc.

What do you do for fun, and how do you think about leisure time?