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.

In their quest for social change, givers like Arnold are reluctant to support “causes”; they want to “solve problems—big ones,” as Callahan puts it. But, in Arnold’s case, lessons had to be learned along the way. His early forays into philanthropy, including an effort to reform public pensions, were scorned, with critics noting that Enron’s collapse had resulted in the loss of billions of dollars in pension funds.

Moskovitz and Tuna weren’t keen to embrace traditional development organizations, which they are inclined to view as lethargic and bureaucratic. For them, grant making is akin to venture-capital investing: they want to act decisively and disrupt traditional models and structures. They have contributed $32 million to a group called Give Directly, which is not interested in vaccinating children, digging wells, building toilets, and creating schools. Rather, it gives cash handouts to the poor, who are free to spend the money as they wish. Callahan is skeptical of the ideology guiding Moskovitz and Tuna—who favor Silicon Valley mantras such as “empower individuals over institutions”—but he knows they are too influential to ignore. The couple will give away hundreds of millions of dollars every year. They are not yet thirty-five years old.

There are growing concerns about the influence and reach of the superwealthy: “Philanthropy is becoming a much stronger power center,” Callahan says, “and, in some areas, is set to surpass government in its ability to shape society’s agenda.” The state has retreated; the givers have advanced.

in many U.S. cities, elected officials are overwhelmed by debt obligations, and as a result have precious little money to spend on parks, museums, and other public services. The givers have no such constraints. In Boston, the Barr Foundation has done much to shape the city’s arts, culture, and political milieu. In Houston, Richard Kinder is helping to forge a massive network of urban trails. In Detroit, the Kresge Foundation is contributing funds for a new light-rail system. In New York, the Leon Levy Foundation has helped to revitalize a pair of Brooklyn landmarks, the Brooklyn Public Library and the Brooklyn Botanic Garden. These are worthy endeavors, but Callahan is right to express concern about a fundamental shift of power from a “hollowed-out public sector” to elite private givers who are not fully accountable and operate in dark corners.

In 2008 Stephen A. Schwarzman, another cofounder of Blackstone, gave $100 million to the New York Public Library at a moment when the Library was secretly undertaking a dubious real estate and construction scheme. For nearly a decade, the NYPL refused to reveal how Schwarzman’s money was being utilized. Only in recent months did the Library account for the gift’s use: the $100 million formed part of the endowment and will soon be used for new renovation projects.

Under an initiative backed by Broad and like-minded funders, L.A. could add hundreds of new charter schools in a decade. Broad is quick to refute allegations that he is overreaching: “I think everyone is getting heard,” he informed Callahan. “We’re getting heard, the philanthropists. The unions and administrators are getting heard. Overall, we’re creating debate.”

That may be so, but increasingly the debate is among people who already agree. The Givers makes a persuasive case that the superwealthy are expanding their influence at a moment when many Americans are bolting from civic and political life. The author, drawing on the scholarship of Theda Skocpol, evokes an earlier era when mass-membership organizations such as trade unions flourished, giving ordinary citizens a certain degree of influence vis-à-vis elite power structures. These days, he writes, “We’re fast moving toward a future where private funders, not elected officials and the citizens they answer to, choreograph more of public life.”

Of the top eighty American foundations, only twenty-six post detailed information about their current grant making on public databases. The Susan Thompson Buffett Foundation, endowed by Warren’s wealth, “has no real website and the information available on its grant making through tax returns is always a few years out of date,” Callahan notes.

The Givers is alive to these and other contradictions in the philanthropic sector and poses thorny questions for elected officials and nonprofit leaders: why is a check to a right-wing think tank tax-deductible but a check to a conservative senator is not? Why are many large foundations spending a mere 5 percent of their assets each year when they can easily afford to spend more? Why do so many foundations exist in perpetuity, instead of “spending down” and closing their doors? Why is the sector so lightly regulated by government, particularly the IRS? Finally, what exactly is the public getting in exchange for colossal tax breaks granted for philanthropy, which mainly go to rich people?

The Givers, which went to press before Donald Trump was elected, concludes with a stark and prescient warning: the nonprofit sector should initiate its own reforms, before politicians do it with a heavier and more mischievous hand. “It’s not okay,” he warns, “to settle for a status quo in which the foundation world remains forever a black box.” His proposals for change—the creation of a new U.S. federal office of charitable affairs, a reevaluation of what should qualify for tax-exempt status, trustee boards that are more inclusive and transparent—are not likely to be embraced in Trump’s Washington, however.

Katz, writing after Trump’s victory, argued that Callahan has sidestepped the central issue: Our current dire political situation is the product of both traditional American anti-statism and a very different and deliberate assault on the state by plutocrats. We do not have so many billionaires, and thus mega-foundations, because we now have a larger and more adept entrepreneurial class, but because the structure of (mostly federal) economic policy has been captured by people of wealth, who have rewritten the laws to enable themselves to become extraordinarily rich…It seems to me that the new plutocrats are in fact the problem, and they are quite unlikely to be part of the solution, as Callahan contends.

My own wish is that Callahan had confronted, in a more pungent way, the structural features of the behemoth that looms before him: the grant-making model itself, upon which modern American philanthropy rests. Foundation leaders advocate transparency, inclusion, and equality, but they operate in a strikingly hierarchical manner. They are a cloistered elite.

Does this top-down model—in which grantees spend immense time and energy chasing cash—inhibit the growth of dues-paying organizations, which may be more vibrant and democratic than nonprofit organizations dominated by an aloof board of trustees and an executive director? Passages in The Givers suggest that Callahan has pondered these matters, but he stops short of a full critique.

There are now more than ninety thousand private foundations, whose assets total $700 billion. These foundations supply money to more than a million tax-exempt, nonprofit organizations. Some of these nonprofits are financially secure, but many chafe under immense anxiety as they await annual grants from their masters in the foundation suites.