Many people try out careers in venture and then wind up leaving after a year when it stops feeling novel and starts feeling like they’re floating in lonely limbo without any markers of success. That’s because the craft of venture is not for people who derive their satisfaction from external indicators of progress — it’s for people who find the development of their relationships and refinement of their internal model of the world to be motivation enough to keep going.

If you derive satisfaction from refining a craft, don’t go into venture yet.

Here are five individual investor archetypes I’ve noticed can produce outsized returns in the early-stage venture game:Philosopher: hangs one’s reputation on their predictions about the futureHustler: simply outwork everyone else and are great at networkingHawk: most competitive, gets a thrill out of the fight to win a deal Friend: confidante and coach to founders, often founders’ first callCelebrity: a person widely respected for their work/knowledge/skill

A good archetype for you is whichever one you can sustain the longest. A great archetype for you is one that no one else is doing and you have some sort of signal works.

Some good advice I got: build your fund’s structure and strategy around allowing yourself to invest in whichever way you most enjoy and are naturally good at (admittedly, it will probably get harder and harder to stick to this as your fund scales).

Examples: if you like being a friend to founders and want your fund to function as Switzerland (i.e. not compete with anyone), write small checks. If you like to fight and are naturally hawkish, it might make sense to set yourself up to try to lead rounds. If complex problems and futuristic theories are what get you excited, investing in series A companies that fit into where you see the world going could be quite gratifying. If for some reason you love living in spreadsheets, consider growth investing (and don’t follow literally any of my advice).

In many ways, the job of the writer and the job of a VC are quite similar, in that they both ask you to produce an original end product (in the writer’s case, articulated ideas and stories; in the investor’s case, a differentiated portfolio with outsized financial returns) without much of a map for how you get there. The reason professional writers complain about writing so much is that it’s really difficult to wrangle your brain into producing uniquely interesting thoughts all the time, and highly frustrating when you consider it your job to do so. Making good investment decisions is similar; just with the added element of also being highly social. Taking the quality of your self talk seriously seems superfluous but is an investment that will result in better decisions.

A lot of the game of investing is won by getting people to think of you — a sign that you’ve built the kind of moat we call a strong brand. Remember: a fund is just a pile of money with a person on top to sell it. As an investor, putting down stakes in the ground about what you invest in saves you a lot of time in the long run because it allows people to self-select for fit

I’ve been surprised by how much it’s benefited my fund to make Moth’s brand (i.e. what I invest in and look for) difficult to summarize in a sentence. For small early-stage generalist funds like my own, quality matters much more than quantity. Quality deals almost always come from trusted sources who resonate with my taste, not from a list of random companies for which I have no context.

A brand is a promise to show up in the same way time and time again. Good brands are built on being decent and principled with all of the people you interact with.

Lastly and of utmost importance: remember that fear of failure fades into the background if you focus on leaving everyone you encounter along the way better than you found them.

VCs need to believe that your company could be a billion-dollar business and generally lack imagination — you need to paint a vivid picture of this path for them, starting with the striking protagonist character you play in your company’s story.Your alter ego should never lie, but it should be completely comfortable showing the fullest expression of your ambition to people who probably intimidate you. Fundraising is a snap judgment game — most VCs are trying to pattern-match you to a founder archetype who already won. They index primarily on IQ, self-belief, experience, and personability (in that order). A general rule of thumb is that to be taken seriously in SV, male founders would benefit from acting warmer, while female founders are taken more seriously when they act colder. Both benefit from acting a little entitled.

a VC’s job is to make a diversified portfolio of bets — you are only one. Most founders find being around VCs distracting and draining because they feel pressure to perform the role of ‘impressive person.’ If you can’t immediately capture value from your performance… why waste your energy?

don’t expect the average investor to provide much value beyond money and connections. This makes the 10% of investors who can be legitimately useful to your business worth their weight in gold. Develop litmus tests to identify the valuable ones quickly and avoid wasting your time trying to convince nonbelievers.

our goal here is to spend as little time fundraising as possible — which requires being strategic about the order in which you talk to investors and how you talk about where things stand as you progress through the raise. The combined force of controlling those two variables are what “generates momentum” during your fundraise process.

Make a list of all the investors you know and can get introduced to, ordering them by the ones you most want on board to the ones you couldn’t care less aboutTalk first to a few low-stakes investors at the bottom of your list to practice your pitch and identify common investor questions and critiques you’re going to getIf available to you, next get a few investors who already wanted to give you money on board so you have a dollar amount you can say you’ve raisedWork your way up your investor list, talking to the investors you most-want-on-board-but-still-need-to-convince last (this optimizes your odds they say yes)

This all goes by much faster if you court investors similarly to how hot girls treat their many potential suitors. If your raise is already a little taken and you exude an air that you don’t need them, mimetically-minded investors become much more interested.

If you’re anything like me, you will worry intensely about not making a fool of yourself. It will probably go ok, but not as amazing or illuminating as you’d hoped. You might leave and feel a deep sense of lostness set in. This is all very normal. In time you will see them in increasing clarity, often noticing the differences between your and their values and why you would not enjoy living their life at all.

the people on pedestals probably hate being there. It’s lonely, hard to trust that the intentions of the new people around you are pure, and you often feel like you’re constantly letting people down. In the end, idolization hurts everyone involved.

Beware of intellectual dementors and clout demonsIntellectual dementors will try to eat your ideas and interestingness — not necessarily to copy you, but to wring your brain dry to amass knowledge themselves. They often play mini IQ games/tests of will in conversation and masquerade as investors while never actually investing. Clout demons are similar, but view people less as brains and more as stepping stones towards supreme social status. The power move to protect yourself from both is to simply abstain from playing their games — give as little info on yourself and your ideas as possible and reflect their questions directly back at them.

People will help you if you ask for what you want clearly and concisely

Knowing what you want requires a lot of upfront soul-searching, followed by strategic and long-term thinking once you’ve committed to a thing (I can’t really demystify this more). Once you’re all in, I highly recommend diligently keeping a list somewhere of the top three things you currently need help with so when people ask, you’re ready.

You don’t want to make people feel like you’re using them but you do want to use your social capital for things you care about. General rule of thumb: ask for things either 1) after a positive interaction or 2) completely out of the blue with a concisely written and compelling email/text. Tone matters because you don’t want to sound desperate and you do want to show you know how to play the game (write like the founder you most admire talks).

once we’ve taken action on behalf of something, our brain assigns more value to said thing. Tim Keller: “The feeling of love follows the action of love.” Love is a strong word here, but the point stands — help people help you. Startups are long-term games, so it only makes sense to do them with people you truly want to be around for a very long time.

I think a lot of folks feel like you should be doing these certain things like writing the great American novel or reading the 100 Greatest Movies of All-Time when in actuality these are achievements that have no real guarantee of happiness. Unless you are truly enjoying those journeys, there is no reason to set upon them.

I don't think there is anything wrong with having hopes and dreams, but I do feel that maybe we allow those things to be excuses for not living a content life. I also think at times we hold onto old dreams that no longer serve us, instead of focusing on something new and more applicable to your current situation.

adulthood wasn't full of Ferraris and mansions, and I found out rather quickly that I wasn't going to save anyone, because I was struggling to save myself.

The life of an optimist is hard but exciting. Pessimism is easy because it costs nothing. Optimism is hard because it must be constantly reaffirmed.

Dreams are delicate and easy to destroy. When an idea presents itself, try to imagine the best version of it — what would make this idea great?

Pessimism and optimism share a trait: both are self-fulfilling. Your intention influences the outcome. Call it karma or, simply, effort.

Real life doesn't start tomorrow, or on the weekend. It doesn't start when you graduate, or when you land a job, or when you quit your job. It doesn’t start once you get a handle on your anxiety, or fix your sleep schedule, or finish all the tasks in your to-do list.

Real life is made of moments like this. It’s waking up with dread and clutching at your phone for relief. It’s being mildly frustrated at all your friends for the various ways in which they don’t understand you. Real life is wiping the lint from your dryer, it’s scrubbing the same pan clean for the hundredth time, it’s being surprised that even with all the fun of a friday night, you’re just as sad to say goodbye, just as sad as when you were a child.

We spend most of our time waiting, and very few precious moments feeling like we’ve finally arrived. We defer our willingness to bask in reality to tomorrow, and then the next day, and then the next, until we forget we ever deferred anything.

But what if you don’t need to wait until you’ve meditated for decades, what if you’re closer to that than you think? What if you were more often baffled by the fact that you’re still alive, if you began to ask of this moment, of every moment: what do you have to teach me?

You know that feeling you get when you hear the good news you’ve been waiting for, or when you’re so enthralled in conversation you forget that you haven’t checked your phone for hours, or when the rain has settled and you step into the forest and the freshness of the air wrests your lungs open and everything feels perfectly in place?

You’re inflight, you’re falling through the sky, everything feels half-complete, there is so much more you meant to do, there are so many things you’re behind on, so many things you haven’t said. I’m right there with you. This is it, the madness we were born into and have no choice but to face. Real life is more and more of this and then it’s over.

Last year I burnt myself out on introspection and developed a personal philosophy to “take action towards things I think I want until I can come up with a good reason to stop.” Operating in this way might make me look flighty from the outside but on the inside, I know it’s one of the main reasons my life continues to feel like it’s getting better and better — experimentation till I find the things that feel really right.And really right is what I’m going for. Not right on paper, not right only if I turn off my brain, and definitely not right only in the eyes of others. In my book, a good decision is one you know in your heart, mind, and body to be true for you. Some call this discernment, others call it wisdom. All I know is that it’s really hard to find.

Now, uncertainty is a fact of life — one of the few universal rules to this grand, intricate game we’re all playing. As I understand it, the game goes as such: First, conquer your fear of rejection. Second, conquer your fear of uncertainty. Along the way, you’ll need to reckon with your fear of cringe.

But you know what helps? Actually listening to yourself. Not just the insecure parts of you that have something to prove and find it fun to root around for meaning in the struggle. No. It’s the voices that care about your experiencing day-to-day contentedness, belonging, and don’t believe that everything should feel hard that deserve the megaphone — they often sound quite similar to a best friend or parent.

being loved completely actually does the opposite — it motivates me to become more concentratedly myself by providing the comfort of verified belief in my own value. I mention the love thing because I think it has a lot more to do with what makes a decision good than we like to admit (maybe because it’s cringe!). But as Julie Dempsey says in Before Sunrise: “Isn't everything we do in life a way to be loved a little more?”

Gatekeepers could see themselves not only as talent hunters for their own organization, but also as managers of society’s collective supply of ambition. We could demand that they consider it a responsibility to waste as little of their applicants’ ambition as possible. That they strive to redirect and allocate that ambition wherever it is most needed.

In practice, there isn’t any single solution. Rejection is a facet of life, and everybody needs to figure out their own strategies to cope with it. The most I can offer is that it’s better when you’re aware of how it works. It isn’t enough to know, on an abstract level, that rejection is typically random and impersonal — but it helps.