The VC Playbook: How to Win as a Venture Capitalist
In a bubbly VC world, how the hell do I survive?
This is an old post from 2024, originally written in Korean
So, how will I survive as a VC?
What does it actually take to win in venture capital? Having seen the industry from both sides, during my time at KIC, one of the world's largest LPs, where I helped decide which VC funds to back. And now and prior to KIC, from my seat here in Silicon Valley as a VC.
After meeting with and analyzing over 500 VCs, I’ve started to recognize a few distinct archetypes—the different 'playbooks' that top investors use to get an edge.
Understanding the US Venture Capital Game
First, let me quickly break down how I see the VC business. For a primer on the basic VC functions—source, pick, win, support, and exit—you can check out my previous post.
A Market Where the Seller Picks the Buyer
Venture capital is fundamentally different from public market investing. First, because it’s private, information and access are extremely limited. In direct opposition to public stocks: (1) you can't invest, no matter how much you want to, unless the founder chooses you, (2) luck and timing play a huge role, and (3) information is not distributed fairly among all investors.
This means you’re dealing with an asset class that is high-risk, reliant on limited information, and has low accessibility. I believe it's an arena where individual capabilities are paramount. A successful venture fund, in my view, is one that builds an incentive and decision-making structure that empowers exceptional individuals to work harder and smarter. I’ve been thinking a lot about what an optimal VC fund structure looks like and plan to write about it soon.
Because access is limited and you have to be chosen by the seller (the founder), I've never met a successful VC who lacked personal charisma. I’m not just talking about looks. Every single one of them was someone I wanted to spend time with, someone whose network I wanted to be a part of, someone I were eager to work with.
It's a constant reminder that you have to be that magnetic—that capable of demonstrating your value to a founder—to get into the best deals. And frankly, you need that same energy to convince LPs to give you their money. A survey on how founders choose VCs confirms this, with Personal Chemistry ranking at the very top.
As you can see on the left, the most important factor for founders when choosing a VC is Personal Chemistry.
Basically, It's a Sales Job
From that perspective, a VC is not nearly as glamorous as it looks. You're not just elegantly sitting in an office, reviewing inbound deals like in the movies. You are a salesperson, constantly peacocking to two sets of stakeholders: founders and fund investors (LPs). You're also an entrepreneur running your own business in a ruthless market, in a profession where pivoting to another industry after failure isn't easy.
And the higher you climb, the less time you spend investing and the more time you spend fundraising. There's a running joke in the industry for a reason: "Being a VC is 70% fundraising, 20% fund management, and 10% investing."
Like Other Investors, It's an Endless Grind
Furthermore, since the job is not about simple pattern-matching but about finding true outliers, seniority and experience don't guarantee success. In fact, you have to constantly worry about becoming old and missing new trends, or getting stubborn from past wins. It’s a career that demands constant learning and effort, and the workload seems to increase over time.
You can only be happy if you genuinely enjoy the grind of learning, fundraising, and persuading founders. If you're in it just for the money or the prestige, the risk, stress, and exhaustion will be overwhelming.
I've gone on a bit of a tangent because I see so many romanticized ideas about the VC analyst role. Anyway, let's get back to the main topic. Here’s my fun, unofficial breakdown of the playbooks I’ve seen successful VCs use in this unique asset class.
The Playbooks of Successful VCs
1. The Operator
Operators are typically former founders who provide practical advice to a new generation of entrepreneurs, drawing from their own hard-won experience.
Strength
They offer actionable solutions to immediate problems and can genuinely empathize with the immense psychological challenge of building a company. This is a very common archetype in Silicon Valley. Armed with advice and empathy, they have a high probability of demonstrating good judgment in sourcing, picking, winning, supporting, and exiting. Statistics also show that founder-VCs often generate better returns.
Weakness
Their startup experience is in the past. A success formula from yesterday might not work today, and past glory can sometimes lead to stubbornness. While the big picture may be similar, times change, and every company's situation is different. They can also sometimes "forcefully provide" way more advice than the founder actually wants.
Upgraded Version: The Unicorn Builder
Of course, all founder experiences are valuable, but those who have gone through multiple funding rounds and built a unicorn are naturally more sought after. Among them, those who have managed a successful exit via an IPO or a major M&A are at the top of the food chain.
Examples: Marc Andreessen (a16z), Ben Horowitz (a16z), Reid Hoffman (Greylock)
Andreessen and Horowitz, the founders who help founders with massive resources. Hoffman, the founder of LinkedIn and the ultimate connector.
2. The Networker
This is the player who hits the ground running, attending every networking event, knowing everyone in the industry, and having the widest coverage. It might seem like the easiest path, but it requires an innate social talent—a playbook for the true extroverts.
Strength
They dominate sourcing by getting there first. They win deals the same way. Their support comes from sharing information others don't have and connecting their portfolio companies with the right people.
Weakness
While not always the case, their picking and exiting abilities can be relatively weaker. They can leverage market gossip and references to make good picks, but they are also more susceptible to getting swept up in market-wide FOMO.
Upgraded Version: The Matchmaker
This VC excels at creating the perfect connection. In Silicon Valley, matchmaking is a critical VC skill. It's about knowing who to connect with whom for maximum synergy, how to frame the introduction, and how to manage the follow-up to ensure it's a success for both parties.
This may sound simple, but it requires a natural instinct and quick thinking. As I've said many times, a VC's most scarce resource is time. Making an introduction is asking for someone else's time, which is like taking on a small debt. The recipient will judge you based on the quality of that connection and decide whether to accept future intros from you.
If you make connections that don't benefit both parties, people will start avoiding your intros. If you make great ones, your relationships will strengthen. Once you get a reputation as "the person whose intros are a waste of time," your life as a VC gets very difficult. That's why I believe introductions must be strategic, thoughtful, and executed with care.
Example: Every VC. It's the most fundamental part of the job, and yet, perhaps the most difficult.
3. The Content Creator
This playbook involves producing content—memes, newsletters, podcasts—to source deals. Often, it takes the form of writing a newsletter or hosting a podcast to share one's thoughts, like I do.
Strength
The biggest advantage is that you can do the work of a Networker to some degree, but from the comfort of your own desk. While the depth of personal relationships is shallower, the potential reach can be even wider. It also allows for broader personal branding and relatively rapid growth. My own newsletter is a good example; it allowed me to quickly build a network in Korea, a community I barely knew since I live in Silicon Valley.
Weakness
As someone who has used this playbook for over two years, I worry about a few things: (1) Damaging your brand with inappropriate content. (2) Creating opposition—if you share an opinion, you will inevitably attract dissenters. (3) The danger of chasing clicks and becoming increasingly sensationalist.
While it's great that so many are trying this content-driven approach, I often see it backfire. For founders, too, their social media activity can negatively impact investor perception. Honestly, this fear makes me spend more and more time writing each post as my subscriber count grows, and I find myself becoming more cautious.
I also worry about creating an opposition. For any opinion, there will always be people who disagree, and sometimes they get organized. I've received tips that an "Anti-IanPark" group chat exists, and I know my writing can affect my reputation among founders and LPs, so I am very careful about what I write.
Furthermore, this strategy exposes you to people outside your target audience of founders and investors, which I think creates unnecessary risk. In my experience, it's fine when things are going well, but when something goes wrong, you can face a much bigger backlash. It feels a bit like you're borrowing from the future by making a high-stakes bet in the present.
Finally, I'm wary of the trap of writing increasingly provocative topics just to get views. When you create content, there's a moment when clicks and view counts become the KPI, rather than the original purpose of learning and thinking to support your main job. This can lead to a vicious cycle of (1) low-quality content and (2) creating more opposition.
Perhaps I'm more worried because I'm in the trenches myself. But is this playbook bad? If you can be more strategic and diligent to reach the "upgraded version," I believe many of these concerns can be resolved.
Upgraded Version: The Researcher
The final form is becoming a recognized expert who delivers deep insights on a specific sector or macro trend. In the founder survey mentioned earlier, "sector expertise" was the second most desired VC trait.
In this case, sourcing is primarily a top-down effort, using research to identify and proactively contact companies that fit their thesis. They pick and win by persuading founders with their superior understanding of the sector. They provide support by sharing the latest industry tech and trends. What founder would turn down intel on their competitors, like who's #1, how many new customers they're acquiring, and what their valuation is?
When content has this level of depth and objectivity, the problems I worry about—(1), (2), and (3)—are unlikely to occur. I'm working every day to get there myself.
Examples: Mary Meeker (Bond), Tomasz Tunguz (Theory), Micky Malka (Ribbit)
Meeker of internet report fame, rising star Tunguz, and fintech legend Malka.
4. The Number Cruncher
While Researchers love the big picture and macro trends, Number Crunchers are laser-focused on the company level, investing based on micro trends.
Strength
This analytical type, common among hedge fund alumni but less so in traditional VC, relies on deep valuation analysis, often creating traditional hedge fund-style reports. They tend to be more flexible, sometimes investing in public stocks to capture more opportunities. They use interesting and novel strategies, like macro timing, and show strength in later-stage deals where traditional VCs are relatively weak. Some have shown great performance by carving out this niche.
Weakness
They are a bit removed from traditional early-stage VC and tend to be weaker at investing in pre-data startups. Even at Series B and beyond, startups carry far more risk and unpredictability than public companies. Furthermore, if their unique strategies don't pan out, they can lose the trust of LPs who invested for a traditional VC strategy.
Upgraded Version: Private Equity, Hedge Fund, Hybrid Fund
Since these types are accustomed to scrutinizing large datasets and public information, PE or public market investing often seems like a better fit. Some operate hybrid funds that invest in both public and private markets. I sometimes wonder why they take on VC risk with their skill set, but they clearly believe there's a gap in the market. While their flashy and unique ideas are impressive, I have questions about their long-term, consistent profitability.
Examples: Lee Fixel (Addition), Neil Mehta (Greenoaks), Brad Gerstner (Altimeter)
Fixel from Tiger, Mehta from D.E. Shaw, and Gerstner, the super-connector with two soccer fields at his house.
5. The Visionary
To put it grandly, this is the philosopher or prophet VC who reads the currents of the world and discovers an investment thesis through original thought. It’s a bit of a results-oriented label, but legendary VCs who are seen as having an eye for the future fall into this category. It seems to require a combination of immense effort, diverse experience, a powerful ecosystem, and a healthy dose of incredible luck for everything to fall into place.
Strength
They make world-changing investments with a unique perspective that differs from everyone else. With great returns and immense industry respect, they can get into almost any deal they want and collaborate easily with other funds.
Weakness
While they may think about the fund's long-term continuity, they often can't shake the feeling of being a one-person team. Their personal brand and performance are so strong that if something were to happen to the Visionary, the entire fund's existence could be called into question.
Upgraded Version: The CEO
The ultimate upgrade is to be a star investor who also succeeds in building an enduring franchise fund that can carry on their legacy. These individuals invest heavily in the fund's structure and systems, experiment with different models, and spend significant time mentoring the next generation.
Examples: Peter Thiel (Founders Fund), Vinod Khosla (Khosla Ventures), Bill Gurley (Benchmark), Hemant Taneja (General Catalyst)
Thiel of the PayPal Mafia, the one and only Khosla, Gurley of the lean elite, and the sage of Boston, Taneja.
So, what?
Okay, so which one are you?
I want to be a Matchmaker & a Researcher!
Unfortunately, I never had the chance to be a founder. I have a bit of a fascination with and an inferiority complex towards operator VCs, and I think many non-founder VCs feel the same way. I honestly considered starting a company just to get over it, but I realized that's a terrible reason to start a company, so I gave up that idea.
And based on my own gut feeling, I like to believe I'm a pretty decent salesperson and have a knack for matchmaking. I put a lot of effort into figuring out who to introduce our portfolio companies to for mutual benefit, which investors to connect to make everyone happy, and even things like how to connect with Professor Andrew Ng to build the right network to eventually meet the president, and what agenda would get his attention. I'm working hard to get even better at this!
I also personally love reading, summarizing, and debating the latest trends, so I'm trying hard to become a Researcher. Lately, I've been obsessed with the consumer space, which is seeing rapid growth at relatively reasonable valuations. I'd love to meet with interested investors and founders in this area! If you have any good reports or information, feel free to email me at ipark@sazze.vc.
So, what should I do?
This might sound presumptuous, but I believe everyone has natural talents and a unique personality. We all have things we are relatively better at and enjoy more. As you've seen, every playbook has its upsides and downsides (or is just plain hard to achieve), so it's difficult to say one is definitively better than another.
There are countless successful VCs in both Korea and the US who have never written a single line for a blog. Media activity is more visible, so it might seem appealing, but it comes with its own risks. Ultimately, your playbook has to fit you, and you have to enjoy it. I have many friends who write great content because they love it, and I cheer them on. At the same time, considering the risks, I don't think everyone should feel pressured to do it. It's the same logic I used when I decided not to start a company.
I believe we are in the service industry, managing our clients' money to grow it for them. In the end, we are judged and evaluated on our returns and our service. Everything else—all of it—is just a tool to do those two things well. The specific tool doesn't matter. Just make money and provide great service.
As you all feel, the VC world is an incredibly competitive market. I think it's far better to focus on your own strengths and talents, on what you truly enjoy, and to sharpen that into your chosen weapon. That's a much better use of your time than trying to compensate for your weaknesses or wasting time with a tool that doesn't suit you.
Our life is too short, and every single day is game day.