Letter to My 2017 Self: Starting Out in VC

Letter to My 2017 Self: Starting Out in VC

Letter to My 2017 Self: Starting Out in VC

Eight years ago I started a new career as a venture capitalist

Eight years ago I started a new career as a venture capitalist

BY KIVA DICKINSON

BY KIVA DICKINSON

BY KIVA DICKINSON

PUBLISHED ON July 8, 2025

PUBLISHED ON July 8, 2025

PUBLISHED ON July 8, 2025

Snowy forest path with sun shining through trees
Snowy forest path with sun shining through trees
Snowy forest path with sun shining through trees

Eight years ago I started a new career as a venture capitalist. In some ways it was familiar: I had a finance background, coming from a large buyout private equity firm; I knew how to conduct diligence, build models, and write investment memos.

In many ways though — the important ways — it was brand new. My job was no longer about following direction and completing tasks. No matter how complicated the problems I’d previously solved, I had always had direction from my boss. I had never faced the kind of ambiguity that lay ahead.

Four months in, I got my first performance review — and it wasn’t great. It was the first time I’d ever been told I was underperforming. I was humbled, and admittedly a bit frustrated, but most of all I was motivated. It was early, but I had a feeling this was my dream job, and I really didn’t want to screw it up.

Looking back, that reflection gave me many things — most of all, the catalyst to learn some big lessons. These days, when I talk to young investors early in their careers, I find myself trying to share those same lessons, so they might not have to learn them the hard way like I did.

I’m not sure I could have internalized them at the time, but if I could give some advice to 2017 Kiva, here are five things I’d say:


1. Have Calibration Before Conviction

At some point in your first couple of weeks, you will get very excited about a new company to invest in. You will have talked to 20–30 companies at that point and this one will feel like the undisputed number one. When you bring it up at investment committee, however, none of the partners will be excited. It will be so tempting to dig in and try to prove them wrong (knowing you, that is exactly what you will do), but doing so is trying to swim out of quicksand. It will undermine both the deal’s chances and your credibility.

Years later you will think back to this company and how excited you were, and there is a good chance you will cringe. There is just no way you can be properly calibrated in a couple of weeks. The most exciting company in that first pool of 25 might not even be top 25 once you have talked to 200 — and you’re in a business where, of those eventual 25, you might only invest in 2.

As your network and reps increase, your mental model will calibrate. Your conviction will sharpen. When you voice that conviction a few months from now, your team will listen (as long as you didn’t overdo it in your first few weeks).


2. Quit Stressing About Time Allocation — Just Spend More Time

In your previous jobs, it was possible to be finished with all your work. Not here. Generating ideas and business has no endpoint — there’s always more to read, more people to meet. Add internal processes and a crowded inbox, and you’ll be overwhelmed. When you find yourself deep in a deal that won’t close, or a call with a company that isn’t growing, don’t ask if it’s a good use of your time. Just keep going.

Your competition did not all start on the same day. They are all ahead, and the way to catch up is investing the time to get calibrated. You’re not in a race to find a single company — you’re in a race to have conviction in the right place and the ability to convince the decision maker that you can help. Unfortunately, that just takes a lot of hours.

It will be tempting to cut things that feel inefficient — like calling a CEO by phone to pass rather than sending a quick email. Ironically, those small, inefficient moments will be why people want to work with you years later.


3. Everyone Is Afraid of Writing — Just Get Started

You already know the value of writing. You’ve been urged to do it for years, you admire those who publish, and you’ve tried — but writer’s block always wins. The blank page is daunting. It’s easy to get stuck and over-edit, letting perfect be the enemy of good. Writing is scary — I get it.

You may not believe me, but in eight years you’ll be publishing long- and short-form content weekly. Your writing will be responsible for investments, investors, and friendships, and anytime somebody asks you for career advice, you will tell them to “start writing.” They won’t believe you were once just as afraid — until you realized there was no secret other than just getting started.

Writing compounds like interest — slow at first, then exponential. The sooner you start, the sooner the compounding begins. Being scared is normal, but it’s worth it. Don’t overthink it. Just get started.


4. Have Urgency But Not Impatience

This job doesn’t have a lot of explicit directions to follow, so the most important mindset is a bias for action — and the more urgency the better. Urgency will help you ramp quickly — calibrating your judgment and expanding your network. Most importantly, it will help you internalize that the buck always stops with you, so you will get nowhere assuming “somebody else will handle it.” People who act with urgency earn responsibility — and promotions.

This world is flatter than where you came from. Partnership happens closer to 30 than 40, and many CEOs skew younger. People will take you seriously faster than you expect — and soon, you’ll wonder if you’re ready for your boss’s job. Resist that impatience. It will distract you from growing.

Years from now, you’ll work with an amazing psychologist who will teach you a valuable lesson: “What are you rushing toward? There is no destination — you just die — the point is just how much you grow along the way.” On the other end of some of your looming goals, that lesson will start to make sense.


5. The People Who Inspire and Intimidate You Are Still Just People

You will soon have a new group of people you admire — people that lead investment firms, run companies, and write the content you learn from. They will seem to navigate the world with such confidence and self-assuredness. You will want to meet them but will struggle to reach out — you will think there is nothing you possibly have to offer.

Stop idolizing and start humanizing them. Anticipate what they’re struggling with and try to be a solution. Bring investment ideas to the investors. Introduce the CEOs and content creators to interesting and valuable people. Help them without asking anything in return.

Treat them the way you treat your friends — and in eight years, that’s exactly what they’ll be.


In Conclusion

These five lessons apply far beyond VC. They’re really about navigating ambiguity — and the more we grow in our careers, the more ambiguity we earn.

I have no doubt that in eight years I’ll be cringing at what I thought I knew today. That’s okay — it’s the best sign I have that I’m growing.

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2025 SELVA VENTURES
2025 SELVA VENTURES
2025 SELVA VENTURES