Dru's Notes

I left my job in 2017. People thought I was crazy. Almost 10 years later, the safe path turned out to be the dangerous one.

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I left my job in 2017. People thought I was crazy. Almost 10 years later, the safe path turned out to be the dangerous one.

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Dru Riley
Founder of Trends.vc

What is Dru's Notes?

One mental model each day in a few minutes. Habits, business, building products and thinking clearly. From Dru Riley, founder of Trends.vc.

I left my job in 2017.

People thought I was crazy.

"That is so risky."

I saw it differently. I ran my own consulting company. One main client, side work when it came. People were still trying to hire me. I could pick up another contract in weeks.

I had two safety nets. Savings that bought me three or four years of runway. And skills the market wanted. The people calling it risky couldn't see either one.

There was a gap between what they knew and what I knew.

I called it a mini-retirement. Three years off from client work. Jiu Jitsu, reading and biking around Atlanta.

By 2020, money was running low. Either make money or go back to work for someone else.

I built Trends.vc.

Even if I hadn't, the net was still there. The worst-case scenario had an upside.

I could've stayed two more years and reached FIRE through the traditional path. But I would've missed years of exploration. I probably wouldn't have started Trends.vc. I wouldn't have the network, the product skills or the understanding of how I work best.

It's almost 10 years later. Companies are cutting engineering roles. The market that couldn't hire fast enough is contracting. The job I used as my backup plan is under pressure right now.

If I'd stayed, I'd be a software developer in 2026. The skill that was my safety net is accessible to everyone now.

Instead, I spent those years building products, writing and running experiments.

The people calling it risky saw my downside. I saw my options.

The "safe" path was the dangerous one.

What would your life look like in 10 years if you stay where you are?

Previous answers integrated:
- Left job = stopped taking main client, took time off. Jujitsu, reading, improv, biking Atlanta.
- Runway = told himself 5 years, actual burn rate 3-4 years.
- FIRE calculation = knew at the time.
- Everyone's a developer + companies need fewer = pressure from both ends. Full analysis is a separate post.
- Risky path built self-knowledge, time to explore, health.
- Spike = discerning perceived vs real risk, trusting your voice. 10-year update is evidence.

- The opening says "people thought I was crazy." Was it specific people (family, friends, colleagues) or a general vibe? A specific voice makes the story land harder.
- "I had two safety nets." Did you think of them as safety nets at the time or only frame it that way later?
- You told yourself 5 years but had 3-4. Did that gap create urgency earlier than planned?
- "The worst-case scenario had an upside." What's the most concrete version of that upside? If you'd gone back to consulting in 2020, what would you have kept from those three years?
- The spike is discernment: telling perceived risk from real risk. Is there a test you use now? How do you tell "this feels risky because it IS risky" from "this feels risky because other people say so"?