things I've learned since becoming a GP

Every aspect of your job is 100x harder than it was when you were an individual contributor. My job used to be simple as an analyst, associate, then principal. I saw deals, I underwrote deals, and I gave a firm reasons to put money out the door. I was shield from fund admin, K-1s, wire tracking, capital calls, investor updates, SPV accounting - oh and I’m still responsible for building pipeline, winning founders, writing memos, and supporting founders in any way after the check is written.

When starting out, you should be ruthlessly pursuing GP-LP fit. Either find what LPs match your model, or you’ll be banging your head against a wall.

As dumb as it sounds, vibes matter during your raise. Assuming you have done the step above correctly, a lot of LP decision making comes down to whether a) they trust you, b) they believe you can execute on your strategy, and c) they like you and want to work together for the next decade plus. Most people over-index on a and b and under-index on c.

You should be prioritizing dialogue > pitch meetings. Give people a reason to talk to you so you can passively give them updates (ideally showing momentum) instead of asking for more time on their calendar for another pitch. Nobody likes being pitched.

People dislike hate HATE posturing. You don’t have to pretend you have it all figured out (you don’t). People usually want to help, but they’ll assume you don’t need any help (or they won’t want to help) if you’re pretending to be more established than you are.

The best people who can actually help you are people who are a few steps ahead of you (GPs deploying out of fund I / raising fund II). Do whatever you can to create reciprocity with these people so that you can play long-term games with them.

The world absolutely does NOT need another venture fund. There are so many other talented GPs out there. I’m reminded of this every day.

What was rewarded in W2 life is no longer remotely relevant to your situation. Showing face in the office? Playing the corporate politics game? Being fast to resolve comments? None of it matters - only results do.

Results from your first fund will largely be graded based on access. Especially as a pre-seed / seed fund, you will not be expected to show distributed capital (yet). You will be expected to be able to craft a narrative around how the existing portfolio will shape into distributed capital in the future, and that story starts with proving your ability to win allocations to special companies, early.

You will get no re-ups if you deviate from the story you told initial LPs. If you raise on the idea of building a curated portfolio of pre-seed founders, and your average entry price is $25m+ post, you’ve violated your fiduciary duty to your LPs.

LPs play the same game of telephone as GPs and founders do. You shouldn’t expect everybody to love you, but if you piss people off, don’t expect for that to not come around eventually. The list of decision makers in this asset class is a lot smaller than most people realize.

It is very easy to spot who actually wants to be here. Who has actually suffered to sit in the seat they’re in? Pain is a moat, and the more suffering you’ve gone through (months quarters of not paying yourself, constant rejection, loss of social status, etc.), the more conviction you have in what you’re building. The gauntlet that some of the investors I respect the most have gone through would make the average person fold several times over.

Solo GPs are some of the most talented salespeople on the planet. You have to tell a convincing story to LPs, or else they won’t invest with you. You have to tell a story to founders, or else they won’t want you on the cap table. You have to tell a compelling story to other GPs, or else they won’t want to co-invest with you.

Related to the above, if you don’t like sales, don’t become a GP. No shame in acknowledging this. I can promise you that it is not for everybody.

The most interesting investors I’ve met have the most unique backgrounds. Not saying it’s impossible to become a great investor by following the standard path, but more lived experiences equate to broader mental models. On that note, if you want to be more interesting, do interesting stuff outside of work.

The default response from LPs is to come back to them for your next fund once there is more to prove. You can’t take this personal. The best you can do is to disqualify early so that “no’s” come quick and are not drawn out.

You’re not real until you’re real. You will feel imposter syndrome, especially when you’re raising but haven’t had a first close yet. I am not there yet, but the general consensus is that this feeling does not go away for at least 2-3 funds.

You’ll never be able to repay the people that put you into business. There are a million reasons to not invest into a fund I; anybody who says “yes” to you is acting irrationally. You are indebted to these people forever, and you should go above and beyond to make them feel your appreciation.

LPs love specialists, so GPs are encouraged to become specialists. Ironically, most of the specialists I know want to be generalists. Part of the game of investing as a generalist is not explicitly labeling yourself as one (saying what you do not invest in also helps create parameters in people’s heads).

An audience is no longer enough. There was a period where LPs loved the idea of solo capitalists, but that has largely died off. Differentiator? Sure. Part of the firm story? Great. A reason for somebody to back you? No. You need more.

Attention =/= trust. Eyeballs are a proxy for distribution, but conversion rate is a proxy for trust.

You are now expected to produce content, create ecosystems, and be able to tangibly show your inbound funnel (thanks, a16z). At the same time, I would argue that some of the best investors of all time have been the most secretive with their thinking.

Being a solo GP is incredibly lonely. Some of the best advice I got was to not pigeonhole myself as a solo GP, but you’ll have to wear that badge at least to get started (you probably will too for Fund I). Unless you’re wired for isolation and can self-generate momentum, it will wear you down.

However many LP meetings you think you need to take in order to raise your first fund, double triple it. Getting meetings is hard. Closing new investors is hard. Getting them to sign docs is hard. Chasing them down through capital calls is hard.

Very little work done within a venture capital fund is repeatable. Writing quality investment memos takes time. Making reference calls takes time. Putting together LP reports takes time. The people trying to skip corners are risking their reputation to do it.

The better questions you ask, the more memorable you become. If you want to stand out to LPs, GPs, and founders, stop asking the same things as everybody else. Go a level deeper, and see what happens.

ChatGPT will create less entry-level VC roles, but it will give entry-level investors way more leverage. It becomes harder and harder to justify an analyst’s salary below a certain AUM.

Positioning is the most important skill you will ever learn, and it’s by far the most important part of venture investing. Good positioning means that the best opportunities come to you instead of you having to constantly find them. Once you reach this point, it’s hard to lose.

Venture capital = money + deal flow + access + judgment. If you don’t have one of these, you don’t have any.

There is no way to scale warm outreach (or at least I haven’t found one yet). Finding the right person to intro you takes time. Writing a thoughtful connection request takes time. Winning that new person’s approval takes time. There are no shortcuts.

Closing deadlines aren’t real for 98% of opportunities. This applies more in fund investing than direct investing, but it applies in both worlds; it’s not very difficult to adjust legal docs to make more room for investors.

The era of LP investing based only on markups is over. Distributed capital is what funds are being graded on in LP meetings.

Institutional LPs can’t back you (even if they want to). Most allocators have check size minimums that disqualify you automatically. The $2M+ ticket rules out 95% of emerging managers. That leaves you hunting HNWIs, family offices, or fund-of-funds who specialize in tiny allocations.

Raising capital and deploying capital are two completely different skill sets. Fundraising is narrative-driven. Investing is pattern recognition and conviction. Almost nobody is elite at both. You’ll need to learn the one you’re weaker at fast, or hire for it.

The math works against you early. A $10M fund with a 2/20 structure means $200K in annual management fees before expenses. If you’re starting a fund to get rich off fees, I have some bad news for you.

Your portfolio doesn’t care about your IRR. No founder optimizes for your fund metrics. They care about you delivering for them in the form of intros / feedback / whatever else was promised to them. On the bright side, very few other investors are willing to do this work, so the bar is pretty low.

It takes one “yes” to completely change your trajectory.