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Posts tagged startup

40 posts
2026
  1. № 075 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. Jan 12, 2026
2025
  1. № 074 Good, Better, Best Never let it rest! Until your good gets better and your better gets best! Dec 29, 2025
  2. № 062 Issue #61: The Seasons of Scaling Behind every neat growth curve is a messier reality worth talking about. Aug 19, 2025
  3. № 059 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. Jun 09, 2025
  4. № 058 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. Jun 02, 2025
  5. № 057 Issue #56: Building a Superstar Leadership Team The best leaders aren’t building their résumés — they’re building something that matters. May 19, 2025
  6. № 053 Issue #52: Announcing Cargado’s Series A Announcing Our $12M Series A: Building the Future of Cross-Border Freight Apr 07, 2025
  7. № 050 Issue #49: The “MCA” of the USMCA Bridging Borders: The Flow of Trade Between Mexico and Canada Feb 24, 2025
  8. № 048 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. Jan 13, 2025
2024
  1. № 047 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. Dec 30, 2024
  2. № 046 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. Dec 16, 2024
  3. № 045 Issue #44: Life in Startup Land Bean bags. Dec 09, 2024
  4. № 044 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. Dec 02, 2024
  5. № 042 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). Nov 25, 2024
  6. № 041 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. Oct 21, 2024
  7. № 040 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. Sep 23, 2024
  8. № 038 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. Aug 19, 2024
  9. № 036 Monthly Digest - July Read on for some Mexico resources and job opportunities with Cargado! Jul 29, 2024
  10. № 035 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. Jul 22, 2024
  11. № 033 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. Jul 08, 2024
  12. № 031 Issue #30: Monthly Digest – June Coyote is being acquired by RXO as we approach the end of Q2. Jun 24, 2024
  13. № 030 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. Jun 17, 2024
  14. № 029 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. Jun 10, 2024
  15. № 028 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. Jun 03, 2024
  16. № 027 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. May 28, 2024
  17. № 025 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. May 13, 2024
  18. № 024 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. May 06, 2024
  19. № 023 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. Apr 29, 2024
  20. № 022 Feedback Loop Feedback from customers can make or break your product. Read on for a deep dive on early product feedback loops. Apr 22, 2024
  21. № 021 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. Apr 15, 2024
  22. № 019 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. Mar 25, 2024
  23. № 018 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. Mar 18, 2024
  24. № 017 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. Mar 11, 2024
  25. № 016 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. Mar 04, 2024
  26. № 015 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. Feb 26, 2024
  27. № 012 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. Feb 05, 2024
  28. № 010 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. Jan 22, 2024
  29. № 007 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. Jan 02, 2024
2023
  1. № 005 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! Dec 18, 2023
  2. № 002 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. Nov 27, 2023