50 brutally honest takeaways about my time in venture capital
The 50 truths you should know about venture capital and startups
Hey everybody! Welcome back to the newsletter.
My name is Guillermo Flor and I’m an entrepreneur turned Venture Capitalist.
I came across a post on reddit recently that caught my attention and I wanted to share with you.
There are many points I agree with and some that I don’t.
Let me know what you think.
PS: DAY ONE VLOG of the SF TRIP TO Andreessen Horowitz Speedrun’s Demo Day live 👇
My entire career has been in venture capital.
I've worked as an intern. I've worked as a junior VC. I've sold software to VCs. I've been a community builder for VCs.
Here are 50 honest takeaways from my time in venture.
There are not enough good companies out there to justify the amount of venture funds in existence.
It used to be a requirement for VCs to have company building experience, but that has gone away as more funds have popped up. The advice you get from most VCs today is based on something they read and not personal anecdotes. Do not take this advice as gospel.
The best founders spend the least time fundraising. If you make your diligence process a burden on the founder, you’ll have to settle for bottom-tier deals.
VC Twitter is the worst place on the internet. Avoid unless you want to lose brain cells.
You'll constantly hear the line "Where can I be helpful?" Most people cannot offer you help. Accept this, and move on.
The most interesting people have side projects and do not tie their identity to their job. If you want to be more interesting, do interesting stuff outside of work.
Everybody in VC claims to want to be your friend. It's up to you to figure out a) who you want to work with and b) who you can actually do business with.
Having your money locked up for 7-10 years is not ideal, and a lot of LPs are starting to realize this.
It is way easier to 3x your money at a $10mm fund than it is at a $100mm fund.
Over the past five years, I’ve known many funds that have invested based off of hype alone. No diligence, no reference calls, no thought out thesis - only an expectation that somebody else will bid higher in 12-18 months.
*The VC tech stack for nearly every fund is ironically horrible.*Spreadsheets and email are the standard.
Building an audience is overrated. Building a skillset is underrated.
You will not build any skillsets on the job as an analyst or associate at a venture capital fund (unless you consider outbound prospecting as a skill).
The larger the fund, the more focused your job is on sourcing. The smaller the fund, the more you'll have to be a jack-of-all-trades.
Most junior VCs are glorified business development reps.
Proprietary deal flow is a myth.
You can raise a fund on influence, but it is very hard to scale one on clout alone (Ashton Kusher + The Chainsmokers are a few of the only ones that have proven this wrong).
*“Partner track” roles are not as popular as you’re led to believe.*Most analyst / associate roles are two-year positions, then you're expected to find something else after that (preferably joining a portfolio company or starting your own company).
If you earn carry at your fund, consider yourself lucky. 90% of junior VCs get no upside for their work.
If you want to be rich, working as an employee in VC is one of the worst fields to do that.
If you want to work directly with founders, you’re better off joining an actual startup. Your involvement with the founding team will peak during the diligence process, and then it will wane off from there.
Selling to VCs is incredibly difficult. These people are some of the most selective people in the world, and they say "no" for a living.
Venture capital rewards being solely focused on your job for long periods of time. If you have any plans of being multi-faceted and not obsessed with your work, there are better careers for you.
Spray-and-pray seed funds do more harm than good to companies that require large amounts of capital. If a fund isn’t able to follow on into your next round of funding, it sends a bad signal to other investors.
Most VCs are extremely lonely in their day-to-day. Small teams and saying “no” all day will do this to you.
Venture capital is an apprenticeship game. Because of this, you’ll be expected to be in the office to get facetime. It’s tough to find roles that are open to remote work.
You don’t have to focus on content all of the time (I’d argue that many new funds over-index on the importance of having a digital presence). The argument is that more content makes you more discoverable, but that really only applies to a handful of funds (most notably First Round + a16z). Benchmark is one of the best funds to ever exist, and their website looks like this.
The best companies want to work with the best brands of investors. If you aren’t a tier one or tier two fund, you have to figure out another way to get meetings (this typically means more work needs to be done before the call).
There are very few contrarians left in VC because almost everybody is scared to say what they actually think.
Seed and pre-seed investing is all based on narrative. The easiest way to raise money is to tell a story that feeds into that narrative (web3 in 2021, creator economy in 2020, fintech / embedded finance in 2018 / 2019).
The biggest asset an investor has is his / her network, but 90% will scoff at the chance to 10x their network overnight.
If you don’t want the life that your boss has, why are you working there?
The best deals come from people you actually take the time to get to know and become friends with. If you view every interaction as transactional ("you send deals if I send deals"), why do you think anybody would send their best deals to you?
Relying only on sourcing software will get you have you competing for the same deals against everybody else. A Pitchbook subscription will not save you.
Most inbound deal flow is worth ignoring, but if somebody is smart enough to break the mold and capture your attention in email, meet with them.
If you find yourself putting higher emphasis on financial projections or fund returns for seed investments, you’re thinking about it the wrong way.
Serious investors back the best companies. They do have to make up metrics or checklists to justify their decisions.
If you hate virtue signaling, you will hate venture capital.
There will always be an MBA that wants your job. If you’re a junior VC and think you’re indispensable, you’re not.
Venture teaches you to pattern match, but by definition, you are supposed to invest in companies that break patterns. Following the same mental heuristics as your peers will get you nowhere.
You don’t have to live in Miami to “make it” in venture today (spent eight months down there in 2021, thought there was a lot of noise, and decided it was not for me).
If you’re doing a lot of in-person meetings, one easy way to stand out is to not dress like everyone else. Not saying to wear loud outfits, but the Allbirds + vest + Apple Watch + tech pants look has been played out, and you look like everybody else.
“The better the weather, the the better the network. The worse the weather, the better the worker.”
“Don’t talk politics” only applies if you have conservative values.
However many LP meetings you think you need to take in order to raise your first fund, double it.
Fundraising is 90% proving track record and ability to get allocation into competitive rounds.
Most “VC” online communities are trash. You’re better off finding the best one and being engaged there than trying to keep up in 10 different Slack / Discord groups.
If you haven’t built a Twitter audience by now, I’d argue that it’s not a great investment of your time. You’re competing for attention on the most-crowded platform, it’s not evergreen content, and good luck consistently saying something that hasn’t already been said.
The earlier you decide what you want out of your career, the better off you are. Some start a career in venture to increase their options in the future, but then they never leave. Nothing wrong with this, but if you have a plan, you can realize what actions you need to take if venture is not your final destination.
Venture is a branding game. You can only earn your brand through building a track record or being loud on the internet. Which of these options do you think LPs prefer?
Let me know your thoughts.
Also, just launched my newest project: The AI Opportunity
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Frequently Asked Questions About Venture Capital – Based on 50 Brutally Honest Takeaways
❓ What is this venture capital newsletter about?
This newsletter shares 50 raw, real insights about working in venture capital, based on years of experience across multiple roles: VC intern, junior investor, operator selling to VCs, and community builder. It’s a must-read for anyone looking to understand how venture capital really works—beyond the polished narratives.
❓ Who should read this newsletter on venture capital?
This content is ideal for:
Aspiring venture capitalists
Startup founders raising venture funding
Limited Partners (LPs) evaluating VC firms
Tech operators considering a VC career
Business students and professionals curious about the VC ecosystem
❓ What will I learn about working in venture capital?
You’ll learn:
The reality of VC analyst and associate roles
Why most junior VCs don’t receive carry or long-term upside
How most venture firms operate with outdated tech stacks
What really matters when sourcing and evaluating startups
Why partner-track positions in VC are rare and misunderstood
❓ How is this different from typical venture capital content?
Most VC content is vague, promotional, or theoretical.
This newsletter cuts through the noise with first-hand VC insights, challenging common myths around:
Proprietary deal flow
The role of content and audience-building in fundraising
What makes a “top-tier” investor or firm
How to actually get a job in venture capital
❓ What are the most surprising truths about venture capital?
A few of the biggest surprises include:
There’s too much VC money and too few great startups
The best founders spend the least time fundraising
Many funds invest based on hype, not diligence
“Helpful VC” is mostly a myth—very few actually offer meaningful support
❓ What are the best takeaways for startup founders?
If you're raising capital, you'll learn:
Why long due diligence processes can kill your momentum
How to spot performative VCs vs. real operators
Why investor brand matters more than most advice
How to stand out with cold outreach to venture capitalists
❓ Is venture capital a good career path?
Not always. This newsletter explains:
Why junior roles rarely lead to partner positions
The loneliness and mental toll of working in VC
How many VCs lack operating experience and rely on theory
Why it’s one of the worst industries to get rich as an employee
❓ Can you learn useful skills in a VC job?
In junior roles (analyst or associate), you’ll mostly learn sourcing and outreach, which are valuable but limited.
If you want to build real skills, consider:
Working at a startup
Building a product or side project
Developing domain expertise before jumping into VC
❓ Is fundraising from venture capitalists still worth it?
Yes—but only if it fits your business model. The newsletter explains:
The difference between spray-and-pray seed funds and long-term partners
Why storytelling and narrative often outweigh financial projections
The trade-offs of working with non-follow-on investors
❓ What’s the tone of this venture capital newsletter?
It’s direct, unfiltered, and based on experience—not theory.
If you’re tired of VC echo chambers and want real, actionable insights about venture capital, this is for you.
❓ Can I share this venture capital newsletter with others?
Absolutely. Founders, investors, and operators will all benefit from the truth bombs inside. If you want to start a career in VC, raise a fund, or just understand how the game really works—forward it to someone in your network.
Talk soon
- Guillermo
Brutal and brilliant at the same time. Behind every “hot deal” is a messy reality—of power dynamics, pressure, and posturing. If we want healthier startups, we can’t ignore how the incentives in VC quietly shape culture from day one. Founders, know what room you’re walking into.
It was a great travel :)