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The Void.

Essays and insights on growth, challenges, and the experiences that shape us.

From those who've been there.

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Latest1/1/19708 min

The First 90 Days as a CTO: What Actually Matters

Stop coding. Start mapping. Your job is no longer to build the feature, but to build the machine that builds the features.

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The First 90 Days as a CTO: What Actually Matters
Why Your Co-Founder Relationship is Failing (And How to Fix It)
Startups 10m

Why Your Co-Founder Relationship is Failing (And How to Fix It)

65% of startups fail because of co-founder conflict. It’s not about "vision alignment". It’s about role clarity and emotional debt.

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The Art of the "Cold Ask": How to Get Mentorship Without Being Annoying
Networking 5m

The Art of the "Cold Ask": How to Get Mentorship Without Being Annoying

Don't ask "Can I pick your brain?" It's lazy and selfish. Here is the script that actually gets a response from busy people.

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The 0 to 1 Hiring Guide: Who to Hire First?
Hiring 6m

The 0 to 1 Hiring Guide: Who to Hire First?

Do not hire a specialist. Hire a "Swiss Army Knife". The first 5 employees define 90% of your culture.

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Surviving the "Trough of Sorrow": Tactics for Non-Linear Growth
Startups 7m

Surviving the "Trough of Sorrow": Tactics for Non-Linear Growth

After the TechCrunch bump fades, the silence hits. This is where startups die. Here is how to navigate the long, flat middle.

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Impostor Syndrome is a Data Problem, Not a Feeling Problem
Mental Health 6m

Impostor Syndrome is a Data Problem, Not a Feeling Problem

You feel like a fraud because you are comparing your "Inside" (full of doubts) to everyone else's "Outside" (highly curated).

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Salary Negotiation for Introverts: A Script
Career 5m

Salary Negotiation for Introverts: A Script

You don't need to be aggressive to get paid what you are worth. You just need to be silent. The power of the "awkward pause".

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When to Quit: The Difference Between " The Dip" and a Dead End
Career 6m

When to Quit: The Difference Between " The Dip" and a Dead End

Grit is overrated. Sometimes, quitting is the most strategic thing you can do. How to know when to fold the cards.

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How to Fire Someone You Like (With Dignity)
Management 7m

How to Fire Someone You Like (With Dignity)

The hardest part of leadership. If you delay firing a low performer, you are punishing your high performers.

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Mental Models for Decision Making Under Uncertainty
Mental Models 8m

Mental Models for Decision Making Under Uncertainty

You never have 100% of the data. How to use "Regret Minimization" and "Inversion" to make smarter bets.

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Remote Work is Lonely: How to Build "Office Culture" on Zoom
Remote Work 6m

Remote Work is Lonely: How to Build "Office Culture" on Zoom

Slack is not culture. Culture is what happens in the gaps. How to restore serendipity in a distributed team.

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Technical Debt: When to Pay It Down vs. When to Rollover
Engineering 7m

Technical Debt: When to Pay It Down vs. When to Rollover

Not all bad code is bad. Sometimes, speed matters more than quality. The "Credit Card" metaphor for engineering.

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Transitioning from Maker to Manager: The Calendar Audit
Management 6m

Transitioning from Maker to Manager: The Calendar Audit

As a dev, an empty calendar is bliss. As a manager, an empty calendar means you aren't doing your job. The painful shift.

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Fundraising Myths: What VCs Actually Look For in 2025
Startups 8m

Fundraising Myths: What VCs Actually Look For in 2025

It's not about the pitch deck design. It's about the "Secret". What do you know about the world that everyone else is missing?

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The 15-Minute Mentorship Session: How to Prep
Mentorship 5m

The 15-Minute Mentorship Session: How to Prep

You don't need an hour. You need 15 minutes of high-intensity problem solving. How to structure the call.

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