Matt Silver.ai
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#Founder notes

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Posts tagged Founder notes

46 essays
2026
  1. I've been quiet. Here's what we've been building. A week in Chicago that changed how we build, TMS integrations, and automated coverage that's actually live. 9/1/2026
  2. The Builder's Moment: Why 2026 Will Separate the Founders from the Followers AI isn't replacing company builders — it's creating the greatest leverage opportunity in history. The founders who lean in now will build companies that were impossible just 12 months ago. 3/25/2026
  3. Stop Being a Basic Brokerage Technology is how you survive. Expanding into niches is how you become impossible to replace. 2/5/2026
  4. 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. 1/12/2026
2025
  1. Good, Better, Best Never let it rest! Until your good gets better and your better gets best! 12/29/2025
  2. Building the future of freight collaboration How we’re rethinking how brokers and carriers connect on Mexico and Canada freight. 11/6/2025
  3. Issue #61: The Seasons of Scaling Behind every neat growth curve is a messier reality worth talking about. 8/19/2025
  4. Issue #58: Canada Is Live. Market Rates Are Here. Cargado Just Leveled Up. Canada coverage is live. Mexico quoting just got smarter. And we’re only getting started. 6/9/2025
  5. 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. 6/1/2025
  6. Issue #56: Building a Superstar Leadership Team The best leaders aren’t building their résumés — they’re building something that matters. 5/19/2025
  7. Issue #52: Announcing Cargado’s Series A Announcing Our $12M Series A: Building the Future of Cross-Border Freight 4/7/2025
  8. 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. 1/13/2025
2024
  1. 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. 12/30/2024
  2. 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. 12/16/2024
  3. Issue #44: Life in Startup Land Bean bags. 12/9/2024
  4. 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. 12/2/2024
  5. 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). 11/25/2024
  6. Issue #40: Collaboration: The Key to Success Between Brokers and Carriers This industry is built on relationships and doesn't happen without brokers and carriers. 10/21/2024
  7. 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. 9/23/2024
  8. Issue #38: Engineering in Logistics I posted about this last week, but I figured I would double down on my thoughts around hiring. 8/26/2024
  9. 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. 8/19/2024
  10. Monthly Digest - July Read on for some Mexico resources and job opportunities with Cargado! 7/29/2024
  11. 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. 7/22/2024
  12. 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. 7/8/2024
  13. Issue #30: Monthly Digest – June Coyote is being acquired by RXO as we approach the end of Q2. 6/24/2024
  14. Issue #29: Ops Life in Freight Operating freight isn't for everyone. I've done the job - I understand what goes into it. Let's dive deep on the topic. 6/17/2024
  15. 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. 6/10/2024
  16. 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. 6/3/2024
  17. 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. 5/28/2024
  18. 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. 5/13/2024
  19. Issue #23: We’ve got new swag, and some new funding! We raised more money, got some new swag, and have some new partners who are going to help accelerate Cargado’s growth. 5/6/2024
  20. Issue #22: Put on your carrier sales hat, shirt, and pants The first half of my career was spent in carrier sales and I still talk to carriers on a daily basis. Carriers might be my favorite part of freight as I reflect on the carrier sales function. 4/29/2024
  21. Feedback Loop Feedback from customers can make or break your product. Read on for a deep dive on early product feedback loops. 4/22/2024
  22. Issue #20: Five Opportunities to Improve the Freight Industry Some things in this industry are working, but they're not working great. It's time to build better tech for the industry. 4/15/2024
  23. Issue #18: Our First Product Launch We're days away from our very first product launch. I went into what it took to get here so far and what's next. 3/25/2024
  24. Issue #17: Marketing and Brand Identity in the Freight Industry Marketing can be hit or miss for companies in the freight industry. Most companies focus on shipper acquisition, ignoring carriers and potential employees. 3/18/2024
  25. Issue #16: Advice to an Aspiring Entrepreneur Starting a company can be incredibly difficult and isn't for everyone. Entrepreneurship can also be incredibly rewarding. 3/11/2024
  26. Cross-Border Complexity U.S.-Mexico cross-border freight carries so much complexity that there’s never just a simple path to follow in order to execute it successfully. 3/4/2024
  27. Issue #14: Building In Public Building in public can be fun and exhausting at the same time. It's almost a separate personality that you have to manage and produce. Let's talk a bit about building a company. 2/26/2024
  28. Issue #13: The Cross-Border Blueprint I think the most common phrase I’ve said related to Mexico is “cross-border freight is complicated,” and I mean it. I can’t help it, most shippers and brokers find it to be a black hole. 2/19/2024
  29. Issue #11: The Freight Industry Is Changing The freight industry is changing. It’s evolving for the better. It may not seem like that right now but things are moving in the right direction. 2/5/2024
  30. Introducing Cargado I’m proud to announce that Cargado is out of stealth, with a $3M round from Ironspring Ventures, Wischoff Ventures, Zenda Capital, Proeza Ventures, Sahil Bloom, Craig Fuller, & other angel investors. 1/22/2024
  31. Issue #6: How I got my start with Mexico I've been asked often enough how I, a gringo, got involved in cross-border Mexico freight. It's addicting and I love the complexity of it all. Read more for the backstory. 1/2/2024
2023
  1. Issue #4: Supply Chain Startups I've had the opportunity to meet the founders of so many startups in the past few years and I try to help as many as possible succeed. Read on for how I got my start in tech and angel investing! 12/18/2023
  2. Issue #2: Nearshoring is Booming With all this talk about crazy growth in Mexico, let's do a deep dive on what nearshoring means and why it's here to stay. 12/4/2023
  3. Issue #1: Founder-to-Founder Advice Now that I've had time to really decompress and start working on my next venture, I decided to organize my thoughts into this newsletter in hopes of helping founders avoid some of the mistakes I made. 11/27/2023