Entrepreneurship

Feb 5, 2026

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10 min read

Stop Being a Basic Brokerage

Technology is how you survive. Expanding into niches is how you become impossible to replace.

Matt Silver

Entrepreneurship

Jan 12, 2026

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15 min read

The Age of Builders and Doers

How a small group of operators, plugged into AI agents and modern tools, can tap into effectively unlimited scale.

Matt Silver

Logistics

Dec 29, 2025

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8 min read

Good, Better, Best

Never let it rest! Until your good gets better and your better gets best!

Matt Silver

Canada

+10

Building the future of freight collaboration

Nov 6, 2025

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8 min read

Building the future of freight collaboration

How we’re rethinking how brokers and carriers connect on Mexico and Canada freight.

Matt Silver

Entrepreneurship

Aug 19, 2025

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6 min read

Issue #61: The Seasons of Scaling

Behind every neat growth curve is a messier reality worth talking about.

Matt Silver

Entrepreneurship

Issue #57: The Board Meeting Playbook for Startups

Jun 1, 2025

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10 min read

Issue #57: The Board Meeting Playbook for Startups

A practical guide for founders and operators on turning your board meeting into a working session — not a performance.

Matt Silver

Entrepreneurship

Issue #56: Building a Superstar Leadership Team

May 19, 2025

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4 min read

Issue #56: Building a Superstar Leadership Team

The best leaders aren’t building their résumés — they’re building something that matters.

Matt Silver

Mexico

Issue #52: Announcing Cargado’s Series A

Apr 7, 2025

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4 min read

Issue #52: Announcing Cargado’s Series A

Announcing Our $12M Series A: Building the Future of Cross-Border Freight

Matt Silver

Nearshoring

Issue #47: Freight in the Second Trump Era – Trade, Tech, and Transformation

Jan 13, 2025

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6 min read

Issue #47: Freight in the Second Trump Era – Trade, Tech, and Transformation

As Donald Trump prepares to take office for a second time, it’s clear this presidency will look different from his first.

Matt Silver

Entrepreneurship

Dec 30, 2024

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3 min read

Issue #46: First-Time Founder Fumbles

What interim head coaches and first-time founders have in common—and how to avoid fumbling your leadership debut.

Matt Silver

Logistics

Issue #45: AI in Freight: The Right Role for Technology

Dec 16, 2024

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5 min read

Issue #45: AI in Freight: The Right Role for Technology

Before diving in, let’s thank our friends at FreightCaviar for the shoutout in this morning’s newsletter about my X debate with my brother, Andrew.

Matt Silver

Logistics

Dec 9, 2024

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6 min read

Issue #44: Life in Startup Land

Bean bags.

Matt Silver

CrossBorder

Issue #43: Forager vs Cargado, what’s the difference?

Dec 2, 2024

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9 min read

Issue #43: Forager vs Cargado, what’s the difference?

On a very consistent basis, I regularly get asked about the main differences between Forager and Cargado.

Matt Silver

Entrepreneurship

Issue #41: Founder Mode & Defining Success

Nov 25, 2024

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7 min read

Issue #41: Founder Mode & Defining Success

We recently hit several milestones (including sailing past 100 customers) and landed some substantial accounts (getting us to over half of the top 10 brokerages).

Matt Silver

Nearshoring

Sep 23, 2024

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9 min read

Issue #39: What we're building and why

I've tiptoed around what we're building but we're finally ready to talk about what we're building and why we're building it the way we're building it.

Matt Silver

Logistics

Aug 26, 2024

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7 min read

Issue #38: Engineering in Logistics

I posted about this last week, but I figured I would double down on my thoughts around hiring.

Matt Silver

Entrepreneurship

Aug 19, 2024

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5 min read

Board Meetings

I remember when building Forager, I had a conversation with our Series A investor right after we closed our financing with his firm.

Matt Silver

Nearshoring

Jul 29, 2024

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4 min read

Monthly Digest - July

Read on for some Mexico resources and job opportunities with Cargado!

Matt Silver

Entrepreneurship

Issue #34: Five themes from a founders summit

Jul 22, 2024

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4 min read

Issue #34: Five themes from a founders summit

I spent most of Sunday at a founders summit that Ezra Galston of Starting Line organized in Chicago.

Matt Silver

Entrepreneurship

Issue #32: ChatGPT and a new name for The Silver Substack

Jul 8, 2024

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9 min read

Issue #32: ChatGPT and a new name for The Silver Substack

ChatGPT didn't write this post but I wrote this post about ChatGPT. And we've got a new name for this newsletter.

Matt Silver

Nearshoring

Jun 24, 2024

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6 min read

Issue #30: Monthly Digest – June

Coyote is being acquired by RXO as we approach the end of Q2.

Matt Silver

Logistics

Issue #28: Building the right culture in the freight industry

Jun 10, 2024

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3 min read

Issue #28: Building the right culture in the freight industry

I had the opportunity to take our two new hires, Julie Castelbaum and Caroline Celis (CC), to the FreightWaves Future of Supply Chain conference in Atlanta last week.

Matt Silver

Nearshoring

Jun 3, 2024

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4 min read

Issue #27: Sixty Days Post-Launch

We've been live for two months and have twenty-two brokers using our software. This one is a review of those last two months and an update about a couple new hires we made.

Matt Silver

Logistics

May 28, 2024

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8 min read

Monthly Digest – May

After essentially writing a long-form newsletter every week, I decided to try something different with more of a digest format for this week. Turns out this one is still long.

Matt Silver

Logistics

Issue #24: A conversation with a co-founder

May 13, 2024

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12 min read

Issue #24: A conversation with a co-founder

I talked to over a dozen potential technical co-founder candidates and Rylan ended up being the perfect person.

Matt Silver

Entrepreneurship

Stop Being a Basic Brokerage

The Age of Builders and Doers

Good, Better, Best

Building the future of freight collaboration

Issue #61: The Seasons of Scaling

Issue #57: The Board Meeting Playbook for Startups

Issue #56: Building a Superstar Leadership Team

Issue #52: Announcing Cargado’s Series A

Issue #47: Freight in the Second Trump Era – Trade, Tech, and Transformation

Issue #46: First-Time Founder Fumbles

Issue #45: AI in Freight: The Right Role for Technology

Issue #44: Life in Startup Land

Issue #43: Forager vs Cargado, what’s the difference?

Issue #41: Founder Mode & Defining Success

Issue #39: What we're building and why

Issue #38: Engineering in Logistics

Board Meetings

Monthly Digest - July

Issue #34: Five themes from a founders summit

Issue #32: ChatGPT and a new name for The Silver Substack

Issue #30: Monthly Digest – June

Issue #28: Building the right culture in the freight industry

Issue #27: Sixty Days Post-Launch

Monthly Digest – May

Issue #24: A conversation with a co-founder

Congrats on all the Progress