1. Bumpy Beginnings

Hey there,

Welcome to where I write about my journey from a stable Big Tech Software Engineering job to the wild and volatile world of Venture Capital.

Why would anyone want to leave a semi glamorous 9-5 job, where they don’t have to work too hard and get paid $100,000s in cash + liquid stock options?

What is wrong with me?

As a technical lead, I led a team of engineers on a project generating 10s of millions a year in savings for our company. For all intents and purposes, things were great.

But… like all people who make questionable decisions, I wanted more. Long term, I knew I wanted to be a founder or business owner. I enjoy working on a diversity of things, and I wanted to work on something meaningful.

With the onset of LLMs and rapid advancements in AI, it seemed like the writing was on the wall for SWEs like me. I wanted to extend and diversify my career beyond just software.

I evaluated what options seemed possible for me at the time:

1. Stay in Big Tech

   • Learning: Continue to scale myself technically and as a Engineering leader

   • Mission: Meh

   • Finances: Make consistent great money (Total Comp was increasing by ~10% YoY)

   • Life: Be comfortable and have work life balance

2. Go to top tier MBA (Booth, Stanford, MIT, Harvard, Wharton)

   • Learning: Diversify career opportunities and learn relevant skills to build my next venture

   • Mission: Indirectly

   • Finances: Eat opportunity cost for 2 years (~-$$$)

   • Life: Would have a ton of fun

3. Join or start a startup

   • Learning: Formative & hands on learning in the heart of the crucible

   • Mission: Choose what I want to work on, super-aligned

   • Finances: Would need founder equity for ROI : Risk ratio to make sense

   • Life: No work life balance and high stress

4. Join a VC

   • Learning: Somewhere between hands-on and theoretical learning. Get exposure to 100s of founders and 100s of ideas

   • Mission: Depending on the firm, could be aligned

   • Finances: Cash compensation would likely drop significantly, but Carry could be highly valuable diversified illiquid assets

   • Life: Likely high stress, but not as much existential stress as working in a startup

After weighing these pros & cons, I decided that VC seemed like the most promising of these paths. With rose-tinted glasses, I excitedly started trawling Linkedin to find some connections at various firms.

What could go wrong?

This sounds great right? If you want to learn more, subscribe and look out for my next post: So you want to join a VC?

Signing off and signing zero checks,

SWEdonym