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Hotfix to Hot Deal: The Transition from Software Engineer to VC

Estee Rebibo

January 19, 2022

As a software engineer, I loved building things. But as I progressed in my career working at Goldman Sachs and Flatiron Health, I was less drawn to the “how do I build this” and more to the ‘why should this be built’.

I didn’t want to just focus on writing the most space-and-time-efficient algorithm and be done with it; I wanted to know what is the impact of this code on the end-user, why is this driving business value, and how can we improve that.

I started listening to this nagging voice which led me to explore, and eventually, take the plunge into the world of Venture Capital, one of the few industries that put the why under a microscope.

My new position as part of F2 Venture Capital’s investment team has been difficult, but it has also been incredibly rewarding. I would like to share a few of my learnings so far in the hope of promoting transparency and helping anyone interested in a similar transition.

1) Prepare for way less structure

When working in the tech world, everything is structured and concrete. Your life as an engineer is ones and zeros. You write functions with an input and a known output (well at least you hope so). You have a set of tickets, start a two-week sprint, and by the end those tickets are done (again, at least you hope so).

Venture Capital is not that clear-cut and tidy. By definition, the world of a VC investor is far less defined, and it’s mostly up to you how to optimize your day. You want to be keeping your finger constantly on the pulse of hot industries, creating and maintaining authentic relationships, and deep-diving into thesis after thesis to create deal memo after deal memo.

It’s a lot- and can be totally overwhelming for someone used to a world of structure as an engineer.

My number one tip for new VCs coming from a similar background is to set your own weekly, monthly, even daily KPIs- How many meetings do I want to have? How many coffee dates? How many articles to read? By setting these internal frameworks for myself, the undefined workload becomes a lot more doable, and that feeling of accomplishment when you hit your KPIs powers you on!

2) Do not give into bias

Bias is somewhat of a ‘hot topic’ when it comes to investments, and I finally understand why it is so important to recognize and deal with it.

Coming from the operational world as a software engineer, I often catch myself looking at companies through that sometimes-limiting lens. Of course, having technical knowledge is incredibly helpful when assessing tech companies, but it can be easy to fall into the trappings of favoring a company that works in a familiar space because it feels safer or being overly critical of a company working in a space in which you don’t yet have a footing.

To this end, I have learned how important it is to check myself after every meeting, not to fall back on my experience, and to be relentless in checking references and deep diving into research- no matter what industry a company is exploring.

3) Focus on the market

As a technologist, I am naturally fascinated by the product/tech and when I first began meeting founders, all I wanted to talk about was their product.

However, I soon learned that this is not the right approach. Rather, the best approach for a meeting is coming in believing the product will work. Not only does this create better energy and give these entrepreneurs the respect they deserve (this is their heart and soul they are presenting!) but it also puts the focus where it needs to be — the market.

A team can build some incredibly amazing tech, but if the business opportunity isn’t there it doesn’t matter. I have seen some companies with super complex and impressive tech, but ultimately, we couldn’t proceed because we couldn’t find the market need.

In that first meeting, it’s less about “can they build it” and more “if they build it, will they come?” If we have conviction in this, then we can start digging into the product.

4) Trust yourself!

One trap that I have found myself falling into in my short journey as an investor is self-doubt. It is very hard not to question yourself when you have to say yes or no to a company- you’ve only been looking at their industry, product, and business model for 30 minutes while they have been breathing it for months (maybe even years) — who are you to be deciding if it’s viable? I think this is especially prevalent in early-stage VCs when you do not have a lot of data to work with.

Any engineer knows the magic of stack overflow- the public platform where you will find the answer to (almost) any coding problem. It dawned on me early on there is no such equivalent in VC. While there may be resources- your network, Google, Crunchbase, and more- ultimately, you will need to process these inputs and make your own final judgment.

While I am constantly trying to make my decisions as data-driven and as objective as possible, learning to trust myself will always be a challenge as these are big decisions to make. I welcome suggestions on how to alleviate the feeling of self-doubt from other VCs!

I am still learning, making mistakes, finding my footing, and growing every single day and I feel so lucky to have found F2, a VC that encourages questions and transparency as I learn the ropes.

I also feel like, despite all the growing pains, my background as a software engineer on the ground has helped me tremendously- whether it is being able to deep dive into the technology behind a product, being used to long hours, and sometimes seemingly impossible deadlines, or simply (and maybe most importantly) being able to empathize with how incredibly hard it is to build things.

Ultimately, I feel privileged to be in the world of venture capital where I can make a difference and be a resource to the incredible founders that I meet every day.

On that note- if you’re a technologist looking to get involved in the VC ecosystem or a founder starting to think about funding — we are always, always here to chat at any point in your journey!

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