This week, I’ve been thinking about fundraising, how I’ve spent my time off, and reading.

Questions

Business

Last week, an angel investor syndicated a Special Purpose Vehical (SPV) to make it easier to collect investments from a large group of people. How can we market the SPV to investors?

Same as any marketing, it comes down to two things: Audience and messaging.

Audience

The main point of an SPV is to cut the minimum investment size to something manageable for more investors. The minimum for our SPV is $1000.

Compare that to our friends & family raise, which we did earlier this year, which had a minimum of $5000.

This means that our audience for the SPV is anyone from extended family and friends to institutional investors who might put a small amount into the SPV to maintain a relationship with the company so they’re top of mind when it comes to raise a more traditional institutional round.

We’re targeting a minimum of $100K but hope to raise at least $300K. That means we’ll need to reach out to a large number of investors.

Messaging

The messaging depends on the audience, so the first step in coming up with good messaging is to segment the audience into different cohorts. One might be ‘angels who have a Harvard affiliation,’ another might be ‘angels who I’ve previously met with,’ and another might be ‘extended family and friends,’ and so on.

Next, I’ll define a core message — what stays the same for each cohort — before personalizing it and making it more relevant for each cohort.

The core message will be something like, “Nayak is a Techstars-backed Bay Area-based sales enablement solution for B2B companies that solves the challenge of upskilling representatives to meet changing buyer expectations and an ever-changing product, market, and technology landscape. 97% of sales leaders identified reskilling as their top priority. Founded by a team that’s experienced this problem first-hand, Nayak’s solution empowers sales leaders to continuously upskill teams with real-time coaching, personalized messaging, and buying committee mapping.”

I’ll include some more details like — “We have $23,000 in pilot revenue, 193+ waitlist members, and 40 users.”

I’m undecided on whether to attach the memo, which includes a brief writeup and a pitch deck, to the initial outreach emails, or if I should ask the recipient if they’re interested in seeing the memo first.

Personal

What worked and what didn’t during my time off? How can I continue to build habits and routines into my daily life after I return to work?

I set some goals for myself for my time off. I planned to get a lot of sleep, exercise, work on some physical therapy exercises for my hip and shoulder, read, and journal. My goal was to do all of these things every day.

I didn’t meet that goal. Here’s what happened:

The Good

I read (listened to audiobooks) every day. I feel mostly caught up on sleep. Journaling was hit or miss, but largely went well. There was one entry in particular I feel really good about that I’m considering publishing in some form — a letter to my younger self.

The Bad

I didn’t exercise nearly as much as I wanted to, walking only four days this week, and I only did my physical therapy exercises on two days.

The Ugly

Food poisoning; unceasing rain for multiple days.

Learnings

I can make excuses, but the truth of the matter is, I underestimated how much rest I needed.

I needed to sleep in without worrying how much of the day I was missing.

The main learning is not any big secret about routines or meeting your goals. The main learning is that I should set smaller goals in fewer areas.

My dad shared this blog post from Eric Barker with me about New Year’s Resolutions, and something resonated — “set goals so minuscule that they're basically homeopathic. Make it too simple not to do until it’s a habit. Then, with inertia on your side, expand.”

He suggested that if your big goal is to floss, set a minuscule goal of flossing just one tooth.

It should be so small it would be embarrassing not to do it. Jog for just one minute, or just five minutes. Anyone can jog for just one minute. The goal here is not the point, the point is to build a habit around that goal.

Misc.

What have I been reading lately and what have I learned from those books?

The main thing I’ve learned reading this week is not from the books themselves but from the act of reading.

Medium

Audiobooks have been my go-to for many years. This week, it stood out to me. One book on my list, Franny and Zooey, has no audiobook available. So I tried to sludge through an ebook form, on my phone. I’m embarrassed to say I’m still not finished with it, and it’s a short book.

I don’t feel bad about listening to audiobooks vs actually reading (research shows the two are almost identical in terms of comprehension). But it does make me conscious of my inability to focus on the page alone for long periods. When I listen to audiobooks, I’m usually doing something else, walking, cooking, cleaning, or playing video games. It almost feels like I’ve lost the ability to single-task.

I blame my smartphone addiction. (More on that later)

Reading and Loneliness

This week, I spent a lot of time alone. I was house-sitting for a friend.

One thing that stood out to me during my time alone is that some activities made me more lonely than others. Sometimes significantly more lonely.

Watching TV, for instance, was a neutral activity. It didn’t make me more or less lonely compared to before I started it. So was playing video games.

Scrolling on social media made me significantly more lonely. Dating apps were a mixed bag — if I was actively talking to someone, it made me significantly less lonely. If I was just swiping, it made me more lonely.

Reading was the only activity that always made me less lonely.

It’s like the activities that made me aware of the people I wasn’t with and the things I wasn’t doing that I could be doing or should be doing always made me more lonely. That party my friends were at without me, even if it was on the other side of the country or abroad, made me feel left out or excluded.

Reading brought me closer to other people’s inner worlds, and that made me less lonely.

What I Read

The Magicians (trilogy) by Lev Grossman, 8.5/10

I was first introduced to The Magicians via the Syfy show — the books are a lot better. Storylines that are spread out across all three books are condensed to single episodes. Powerful writing about solitary journeys is portrayed as a multi-person quest, which is often the case in book-to-film adaptations (film relies on dialogue to move the story forward and show character development in a way that books can do with a character’s inner world).

I found magic, the ability to change reality with words, to be a metaphor for writing, and I found that profound.

A Little Life by Hanya Yanagihara, 9/10

I’ve only just started to reread this one, and I’m reminded how intricately the four main characters are developed, spanning decades for some and a lifetime for others.

Sometimes it can devolve into tragedy porn, but even that has a beauty to it.

The Dawn of Everything by David Graeber and David Wengrow ?/10

(The reason for a ?/10 rating is I’m not yet finished with it).

A friend recommended it to me after reading my Medium article on Hunters and Farmers. The book traces human origins over a long time, including, yes, hunting and farming. The main idea is that ancient humans lived complex lives in complex societies that were anything but nasty, brutish, and short.

One thing I’ve learned is that modern property law comes from Roman property law, which includes three qualities: The ability to use, enjoy, and destroy. Under this framework, a person only owns something if they have all three.

Some cultures, including many Native American cultures, defined property differently and assigned responsibilities to property rights. Ownership came with an obligation to protect, maintain, and, sometimes, share. What does it say about a society that defines ownership as the ability to destroy but not the obligation to maintain?

Quote

Reflection

This morning, I left my phone at home and went on a walk. I was inspired partially by a post from a writer I follow and admire, Billy Oppenheimer, in which he shares a habit of highly creative people. “They all carved time out each day for free floating thought… Periods of time in which they forced their body to be still so their mind could be active.” He goes on to quote a brain scan study of these ‘free floating thought’ periods in which they find “a brain that was actively connecting thoughts and experiences.”

I’d agree with Billy about the importance and effects of these periods, but I’d disagree with Billy on what to call them — I’d call it ‘boredom,’ not ‘free floating thought.’

During the walk, I did actively connect thoughts and experiences, which helped me outline and write this newsletter. I think that’s the brain’s natural response to boredom.

I’m reminded of a time when I was happiest, in Taos, New Mexico, on a COVID retreat, during which time I left my phone at home to write the first draft of my novel. There were other factors at play than just my absent smartphone (community, free time, writing), but I remember my ability to sit with one thought for long stretches, my ability to focus, my ability to concentrate and think deeply, was heightened.

Let’s take this newsletter as an example. As I sit down to write it, my phone buzzes, and I look at it, and then I open a different app, I refresh my email even though I’m not expecting anything, I scan through social media for no reason other than habit. Then I turn my phone to silent, and I return to write this, but there’s a nagging sense, almost a phantom limb, of potential notifications and infinite distractions.

I’m considering taking a break from my smartphone, but I’m not totally sure what that would look like yet. While I was on my walk, I thought about what I do on my phone that I can’t do on my laptop.

Here’s the full list I came up with:

• GPS navigation

• Two-factor authentication & authenticator apps

• Tracking the results of my fitness wearables

But David, you might be thinking, what about texts and calls? What about dating apps? What about social media? What about x, y, or z?

Of those, texts and calls are the only ones I wouldn’t be able to do in every situation, on my laptop. I could port my number to Google voice and do most of everything I need to do from my laptop. But I wouldn’t want to need to find a Starbucks to connect my laptop to wifi to tell someone I’m meeting that I’m running late, or that I’m having trouble finding them.

Most dating apps can be accessed online. Most social media platforms can be accessed online.

If I could find a suitable replacement for my smartphone that can handle GPS navigation, two-factor authentication & authenticator apps, and tracking the results of my fitness wearables, that can also text and call, and that wouldn’t suck me into a whirlwind of notifications and distractions, I’d shelve my smartphone for a period.

So far my best find is the Lightphone (which has texting, calling, and maps) plus a tablet for tracking my fitness wearable and authentication. Two devices seems cumbersome, and my worry about using a tablet for those things is I’d just bring it with me everywhere and use it for everything I hate my smartphone for.

Maybe instead of dry January I can do a smartphone-free January. Although given today’s date, it would probably start mid-January at best.

Qs for Next Week's Newsletter

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?

Personal

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

Misc.

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