People often ask me how I got into VC. It’s a difficult question to answer because the truth isn’t sexy or fun. Getting hired in VC was a winding, frustrating, and often draining process during which I repeatedly convinced myself this wasn’t the path I wanted to take, then reignited interest. I’m happy to share the nitty gritty with anyone who asks. While I was lucky to have a few investors believe in me, more often than not, interview processes left me exhausted and underwhelmed.

When I wasn’t “looking,” the opportunity to join NextView Ventures arrived. Getting an offer was a tremendous privilege; I do not take it lightly, and I know my gain was the loss of other candidates who were likely equally if not more qualified. Now two months into the job, I’ve spent a good deal of time reflecting on what would be helpful to share about my early days in venture. There are many resources available on how to get into venture, and millions of “what I’ve learned in my first 60 days as a VC” posts. Instead of contributing to the noise, I decided to get real and share what I’m still struggling with. Which is a lot!

Non-partner venture roles are not easy. They’re high pressure, often no- or low carry, and quite vague. You enter not knowing what you’re supposed to do, and you’re rarely presented with a manual. I tend to gauge my professional confidence based on how frequently I use the word “should” — a trick I learned in therapy. My therapist flags when I’m speaking about what I “should” be doing or feeling, as opposed to what I am doing, feeling, or thinking. After two months in venture, I’m saying “should” a lot.

I share this reality not to downplay my abilities or the support of my team — which is amazing. Nor am I embarrassed by my “should”-ing; it’s a sign that I’m pursuing an opportunity that makes me uncomfortable, and that’s a sign I’m learning. Those who aren’t should-ing have either been at this way longer than I have, or they’re lying. I don’t enjoy being bored, and believe that life is too short to stay professionally comfortable.

I’m being honest about my insecurities and confusions because after cutting my teeth at Bridgewater Associates, one of the most radically transparent workplaces, and building a journalism career rooted in “vulnerability at scale,” I know that pretending you know it all gets you nowhere. I also know that I’m not the only one struggling, and that as a white woman I have an added privilege to speak up.

Alas, I’ve put together the top things I’m not getting about VC. Perhaps it’s because I’m undereducated or inexperienced, or perhaps it’s because these things truly don’t make sense and should change. Either way, I’d love to hear your thoughts.

We’re all doing the same thing but we’re sketchy about collaboration

I work at a seed stage fund. I think it’s a wonderful, brilliant fund, with a differentiated perspective and smart humans. That’s true of pretty much every other seed stage fund, too. Many of us are qualified and smart. We’re all hungry for the best deals. Most of us are looking at the same deals. Yet more often than not, we avoid collaboration and keep our cards close to our chests.

This strikes me as a bit… wild. Not because I am an idiot — I know we cannot all win, and that inviting everyone to your party can amplify competition. This is especially true for partners, as they’re the ones making the calls and setting the terms. But for junior VCs, I think it’s a different story. We’ve open-sourced everything in tech beyond our own success. For many of us, our incentive is to see and surface as many of the best deals as possible. Economies of scale would make all our lives a lot easier.

I’m not suggesting that all junior VCs create a shared spreadsheet, but hey, it’s an “extreme” concept worth contemplating. All I’m saying is that over the past two months, I’ve made a concerted effort to reach out to seemingly high-quality non-partner investors, genuinely get to know them, and make it clear that I’m pro-collaboration. I come from newsrooms and early-stage startups, where our team’s success depends on our ability to collectively source news, ideas, and facts. I intend to take the same approach to venture among those I trust, and those who trust me. I believe our inherent fear of showing our cards is holding us back — especially women and people of color.

A common junior VC experience is being amped up after a first call, bringing the company to a partner, and facing either crickets or an immediate no. Cringeworthy as this experience is, I kind of love it. Getting slapped around a bit hardens your skin and encourages you to come prepared. Tough love is love nonetheless.

That being said, I’m a bit confused by intense skepticism as a form of social currency in this industry. Since my first days reporting on then interviewing with VC partners, I’ve noticed that the ability to quickly (if not instantaneously) call out what’s wrong with a founder’s idea or vision is often equated with intelligence. I find that ironic given our charge is to bet on what’s possible. Rarely does the future match our predictions, which ought to encourage us to see beyond our squints.

Healthy skepticism is undoubtedly key to success. As many folks have said, we’re in the business of saying no. What irks me as someone coming in with fresh eyes is how rarely we emphasize that we’re also in the business of saying yes. Of making visions that seem impossible come true.

This isn’t a call for blind pipe dreams. My parents nicknamed me Eeyore at age five; I quite enjoy pessimism. Rather, it’s a call for asking how “might” this business succeed before talking about what they “should’ be doing differently.

If partners want to groom their junior teammates into nuanced investors, they’d be smart to push the conversation toward what is good or exciting about a business before shooting it down. This is a skill NextView partners come to naturally, for which I’m extremely lucky. When I present an idea — no matter how poorly — they ask what I like about it, and respond to my enthusiasm with questions and comments, rather than immediate critique. They ask why before saying no. What’s more, when they do say no, they distinguish between a “this isn’t for us, but here’s the squint of how I could see it working,” and a “no, this has a fatal flaw, and it’s X.” Even if the ultimate decision is a pass, this approach helps me learn rather than scaring me into silence. I know I speak for more than myself when I say immediate and unqualified rejection isn’t motivating or educative.

All seed funds want to differentiate from other seed funds. Service offerings intended to “be helpful” to founders are a common refrain. We ask what we can do to “add more value,” convincing ourselves that semi-delusional navel gazing is productive. I don’t mean to shoot down service offerings — many are impressive and convert deals. But I’m unsure whether, on an individual investor level, “being helpful” is more important than being kind and real.

To reiterate, I’ve been at this for two months and am a Dalio-certified “dumb shit.” However, with the founders I’ve met through NextView and as an angel, it seems the most helpful thing I can do is to tell them the truth and not be an asshole. Founders are engaging with VCs for money not for fun or new buddies. Our job is to give them that money or get out of the way, while also convincing them that our experience giving other people money makes us a valuable sounding board and differentiates our undifferentiated capital.

When we write rejection or mid-deal emails, we ought to focus less on value-add platitudes and more on honesty: What’s good about the founders’ business, and what’s not working in our eyes. Admission that we could be wrong. The truth about why can or can’t we “get there” — founders have thick skin, they can handle it. What would need to be different for us to have more conviction in this business? Where might we be ignorant of our own blinders. This feedback does take a minute or two extra, but somewhat counterintuitively, it results in higher trust, which translates to founders sending more information and more deals — even if you pass on them.

Perhaps most importantly, both in founder and intra-fund relationships, our honesty should not outweigh kindness and respect. It confuses me when people think being mean or hyper-intense makes them powerful, when in fact, it makes you seem insecure. As investors and teammates, I think we’ll win by being good people — by being genuinely invested in one another’s success (pun intended), and open-minded enough to listen to one another’s perspectives. At NextView we tend to believe that our team’s brain trust is worth more than its independent parts. The same goes for the founders we meet, inclusive of those we pass on. Confidence comes from conversation and consideration, not from being right.

If these reflections resonate, feel free to let me know @LeahFessler. If not, be kind.

Thank you to Jay Drain Jr. and David Beisel for reading my drafts. I appreciate you.

This post originally appeared on Medium and is republished here with the author's permission.

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