people mix up two very different types of pivots and that it’s important to differentiate which path you’re on: Ideation pivots: This is when an early-stage startup changes its idea before having a fully formed product or meaningful traction. These pivots are easy to make, normally happen quickly after launch, and the new idea is often completely unrelated to the previous one. For example, Brex went from VR headsets to business banking, Retool went from Venmo for the U.K. to a no-code internal tools app, and Okta went from reliability monitoring to identity management all in under three months. YouTube changed direction from a dating site to a video streaming platform in less than a week. Hard pivots: This is when a company with a live product and real users/customers changes direction. In these cases, you are truly “pivoting”—keeping one element of the previous idea and doubling down on it. For example, Instagram stripped down its check-in app and went all in on its photo-sharing feature, Slack on its internal chat tool, and Loom on its screen recording feature. Occasionally a pivot is a mix of the two (i.e. you’re pivoting multiple times over 1+ years), but generally, when you’re following the advice below, make sure you’re clear on which category you’re in.

When looking at the data, a few interesting trends emerged: Ideation pivots generally happen within three months of launching your original idea. Note, a launch at this stage is typically just telling a bunch of your friends and colleagues about it. Hard pivots generally happen within two years after launch, and most around the one-year mark. I suspect the small number of companies that took longer regret not changing course earlier.

ou should have a hard conversation with your co-founder around the three-month mark, and depending on how it’s going (see below), either re-commit or change the idea. Then schedule a yearly check-in. If things are clicking, full speed ahead. If things feel meh, at least spend a few days talking about other potential directions.

Brex: “We applied to YC with this VR idea, which, looking back, it was pretty bad, but at the time we thought it was great. And within YC, we were like, ‘Yeah, we don’t even know where to start to build this.’” —Henrique Dubugras, co-founder and CEO

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.

When I first started meeting founders, I wanted to help with anything and everything. Unfortunately, that's neither realistic or possible. For example, I have many responsibilities at my day job that must come first. Over time, I have honed in my pitch to be explicit about how I can and can't help. See the notes above about ways to be helpful, and find your own unique combination of value to bring to the table.

My contract typically looks like this: We agree to meet ~X hours per quarter/half/year Multiply by Y contracting rate Y ⨉ X = some dollar amount Z Divide Z by the startup's latest price per share to arrive at a number of advisor shares to grant

Be founder-friendly! It's a big deal and a lot of paperwork to get a smaller check or advisor on the cap table (unless they already have a lot of operational infrastructure in place) – this usually means being relaxed about the commitment paperwork or helping out pro-bono for the first few hours while they work through the logistics.

Finding founders you work well with can be a numbers game; you won't be sure what you like doing until you've met a handful of founders, done several advisory meetings, and poked at different types of problems. It's okay to dip your toe and warm up to the process before committing a lot of time and energy to this. I started slow, and have been steadily sharpening my own intuition about what kinds of products and founders get me excited, and where I can add unique value

Most startups end up doing something different than they planned. The way the successful ones find something that works is by trying things that don't. So the worst thing you can do in a startup is to have a rigid, pre-ordained plan and then start spending a lot of money to implement it. Better to operate cheaply and give your ideas time to evolve.

Successful startups are almost never started by one person. Usually they begin with a conversation in which someone mentions that something would be a good idea for a company, and his friend says, "Yeah, that is a good idea, let's try it." If you're missing that second person who says "let's try it," the startup never happens. And that is another area where undergrads have an edge. They're surrounded by people willing to say that.

Look for the people who keep starting projects, and finish at least some of them. That's what we look for. Above all else, above academic credentials and even the idea you apply with, we look for people who build things.

You need a certain activation energy to start a startup. So an employer who's fairly pleasant to work for can lull you into staying indefinitely, even if it would be a net win for you to leave.

Most people look at a company like Apple and think, how could I ever make such a thing? Apple is an institution, and I'm just a person. But every institution was at one point just a handful of people in a room deciding to start something. Institutions are made up, and made up by people no different from you.

What goes wrong with young founders is that they build stuff that looks like class projects. It was only recently that we figured this out ourselves. We noticed a lot of similarities between the startups that seemed to be falling behind, but we couldn't figure out how to put it into words. Then finally we realized what it was: they were building class projects.

Class projects will inevitably solve fake problems. For one thing, real problems are rare and valuable. If a professor wanted to have students solve real problems, he'd face the same paradox as someone trying to give an example of whatever "paradigm" might succeed the Standard Model of physics. There may well be something that does, but if you could think of an example you'd be entitled to the Nobel Prize. Similarly, good new problems are not to be had for the asking.

real startups tend to discover the problem they're solving by a process of evolution. Someone has an idea for something; they build it; and in doing so (and probably only by doing so) they realize the problem they should be solving is another one.

Professors will tend to judge you by the distance between the starting point and where you are now. If someone has achieved a lot, they should get a good grade. But customers will judge you from the other direction: the distance remaining between where you are now and the features they need. The market doesn't give a shit how hard you worked. Users just want your software to do what they need, and you get a zero otherwise. That is one of the most distinctive differences between school and the real world: there is no reward for putting in a good effort. In fact, the whole concept of a "good effort" is a fake idea adults invented to encourage kids. It is not found in nature.

unfortunately when you graduate they don't give you a list of all the lies they told you during your education. You have to get them beaten out of you by contact with the real world.

really what work experience refers to is not some specific expertise, but the elimination of certain habits left over from childhood.

One of the defining qualities of kids is that they flake. When you're a kid and you face some hard test, you can cry and say "I can't" and they won't make you do it. Of course, no one can make you do anything in the grownup world either. What they do instead is fire you. And when motivated by that you find you can do a lot more than you realized. So one of the things employers expect from someone with "work experience" is the elimination of the flake reflex—the ability to get things done, with no excuses.

Fundamentally the equation is a brutal one: you have to spend most of your waking hours doing stuff someone else wants, or starve. There are a few places where the work is so interesting that this is concealed, because what other people want done happens to coincide with what you want to work on.

So the most important advantage 24 year old founders have over 20 year old founders is that they know what they're trying to avoid. To the average undergrad the idea of getting rich translates into buying Ferraris, or being admired. To someone who has learned from experience about the relationship between money and work, it translates to something way more important: it means you get to opt out of the brutal equation that governs the lives of 99.9% of people. Getting rich means you can stop treading water.

You don't get money just for working, but for doing things other people want. Someone who's figured that out will automatically focus more on the user. And that cures the other half of the class-project syndrome. After you've been working for a while, you yourself tend to measure what you've done the same way the market does.

the most important skill for a startup founder isn't a programming technique. It's a knack for understanding users and figuring out how to give them what they want. I know I repeat this, but that's because it's so important. And it's a skill you can learn, though perhaps habit might be a better word. Get into the habit of thinking of software as having users. What do those users want? What would make them say wow?