Mailbag: Deep research tips, my favorite reads, and living a meaningful life

Hey friends,

Happy penultimate day of 2022!

It feels surreal for another year to be reaching its end.

As many of you know, over the past two weeks, we solicited questions for The Generalist’s first-ever mailbag. I’m glad to say that we got some fantastic prompts, with readers asking for fundraising advice, book recommendations, workflow tips, and what it means to live a meaningful life.

A quick shoutout before we jump into the mailbag…

We’re offering a limited-time 20% discount on membership to The Generalist’s awesome community! We’ve been excited to have a number of you join in the last couple of days and are really looking forward to welcoming more of you aboard.

As a note, this offer will end on January 2, 2023, so time is of the essence.

We don’t tend to offer discounts often, so this will be the best chance to join for the foreseeable future and save between $100 and $240.

Unsure how The Generalist community might help you level up in 2023?

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1. Expanding your professional network. You’ll make real, valuable connections across the tech world, whether that’s with a fintech founder, crypto investor, SaaS operator, or AI expert. Find a business partner, co-investor, or new friend.
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3. Get advice and feedback from smart peers. No one triumphs alone. We all need friends and advisors to help us think things through. We’ve built an amazing community of impressive, collaborative tech practitioners that can help vet your business idea, jam on an investment, or address a strategic issue. Here’s a question one of our community members asked:

Join our curated, members-only community today and lock in a 20% discount. Come meet the people that will help you step up your game and seize the day in 2023.

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Now, onto your questions! As a note, I tried to answer as many as possible, but as we all know, I am not a master of brevity. To keep this from becoming an extremely long post, we’ve saved a few questions for next time. Rest assured that if your query isn’t featured this time around, we’re excited to respond in our next edition.

1. What tools and techniques do you use for deep research? – Ned, Australia

I’m easily intrigued by new research tools and note-taking platforms. Over the years, I’ve tried most. And yet, I still rely on Google Docs to compile information and turn it into usable text. For whatever reason, the simplicity and reliability of Docs make it hard to dislodge, even though there are fine-tuned alternatives for bookmarking, information organization, notes, and so forth.

The tools that have succeeded in achieving regular usage and that I would miss if they disappeared are as follows:

• ​Arc. An elegant next-generation browser. It takes a bit of getting used to, but once you master a few hotkeys and get used to the different UI, it becomes clear that this is a substantial step up from Google Chrome, Safari, Brave, and other challenger offerings I’ve tried in the past.
• ​Alfred. I’ve been using Alfred for years and swear by it. Perhaps because it is run by a small (probably highly profitable) business rather than a venture-backed firm, it doesn’t attract much attention, but it is an incredible assistant. I mostly use it for snippets, which I use as often as possible.

A tool I haven’t used deeply enough to have a sophisticated opinion on yet (but seems promising) is Mem. I’ve tried it here and there, but the team appears to have rolled out new features over the past few months. I’d like to sit down with it at some point and thoroughly assess how I might use it and if it could improve my workflow.

The best thing I do to achieve a deep work state is enter what I call “bunker mode.” I turn my phone and computer to “Do Not Disturb,” block distracting websites (Twitter is blocked for me 99% of the time) and occasionally force myself into using a Pomodoro timer. Usually, I’ll listen to a bit of music to give me a boost, but pretty quickly, I switch it off for better focus. The AirPods do a good job of blocking external noise, and as long as the work is interesting, it's relatively straightforward to work intensely for several hours at a time.

If I’m not feeling inspired, especially on the writing front, I’ll spend fifteen minutes reading quotes from authors I like. (I will search “Coetzee most beautiful quotes” and peruse Goodreads like a weirdo). Reading good, evocative writing activates a part of my brain that makes me want to work, create, and think. Reading about good writing and good writers on LitHub often has a similar effect.

To ensure I don’t miss an appointment while in bunker mode, I tend to set alarms on my phone in advance. I’ll do this most mornings – take five minutes and set alarms that let me know I am about to switch, like a school bell. I picked this habit up from a friend and found it very useful. Not only does it ensure you won’t work through something important, it removes the cognitive stress that the possibility of missing an appointment creates. It feels unnatural at first not to check your calendar every thirty minutes, but this weans you off the habit.

2. What is your information diet? – David, Colombia

I split my time between “hunting” and “foraging.”

Researching a piece for The Generalist or assessing an investment for Generalist Capital is a form of hunting. I have a clear goal and a plan of attack. I have grounds I like to visit and tactics that yield decent results. Above all, my desire is to find the most-informationally rich sources as efficiently as possible. To do so, I visit places like Harvard Business Review (especially the case studies), Bloomberg, The Financial Times, TechCrunch, The Information, Axios, and many others.

Unlike hunting, foraging is done without a specific target in mind. I hope to find something valuable, but I don’t know what. It could be a new idea, a fresh opinion, a writing technique, a bit of wisdom, or something else. By and large, I try and spend my foraging time reading classic books, usually novels. Though there are exceptions, I am broadly skeptical of business books which tend to be twenty-page theses gavaged into four-hundred-page tomes. I’m also mindful that I don’t tend to encounter fiction as part of my day-to-day work – if I want to keep reading these works and benefiting from their wisdom, I must do so concertedly.

3. If you were to restart your journey, how would you seek out LPs without your current audience, and would you choose to raise a fund or spin up SPVs? I have angel invested in a few interesting companies and want to take my game to the next step. I’d appreciate any and all thoughts. – K Man

First, it's important to recognize that venture capital has several different buying profiles. In broad strokes, I would say there are four common LP motivations:

1. The altruistic buyer. This LP believes in you and wants to help, however possible. They tend to be the first people in your fund and are often friends, family, old co-workers, and deeply-engaged supporters. Though having an audience grows this category, most people have some version of this.
2. The access buyer. This LP is investing in your fund to build a relationship with you or your portfolio. They might do this to create social capital (e.g., being able to say, “I’m an investor in Taylor Swift’s fund”) or to get a first look at your deals. Individuals, family offices, and other venture funds (or their GPs) can fit this category. Though the way this relationship is leveraged may differ, the fundamental desire to benefit from proximity is the same.
3. The educational buyer. This LP treats their investment as a form of tuition. They want to learn about tech, venture capital, or a sector you cover and believe this gives them an avenue to do so. High-net-worth individuals – often from older generations – fall into this category, as do professional investors looking to wrap their heads around emergent categories (e.g., crypto, biotech, AI).
4. The returns buyer. This LP wants you to turn their money into more money. They may care about many other things, too, but at the end of the day, they will consider the venture a success or failure based on the numbers you put on the board. Professional fund-of-fund investors mostly fall into this category.