| № 084 |
If your “Mexico person” quit tomorrow, could you still price a load?A 15-minute playbook for benchmarking, spot quotes, and RFPs — and why “gut feel + spreadsheets” breaks down in Mexico. |
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Jun 29, 2026 |
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| № 083 |
The SCOTUS broker ruling: more accountability, not doomsdayA broker-first take on what the Supreme Court actually said, why the internet is overreacting, and what to do next (without panicking). |
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May 19, 2026 |
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| № 082 |
There's No Phantom Capacity. Carriers Just Parked Their Trucks.The US-Mexico capacity squeeze isn't phantom. It's parked equipment, revoked B1 visas, and shippers calling carriers back directly as tariffs lift and the market picks up speed. |
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Apr 30, 2026 |
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| № 081 |
Building the Mexico Team: When to Hire, Who to Hire, and How to ScalePart 4 of the Mexico Freight Playbook — how to staff your Mexico operation at each stage of growth, from your first load to a full department |
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Apr 22, 2026 |
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| № 080 |
The Operations Playbook for Mexico FreightPart 3 of the Mexico Freight Playbook — how the freight actually moves, the documents you need, pricing components, and everything you need to execute flawlessly. |
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Apr 13, 2026 |
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| № 079 |
The Sales Playbook for Mexico FreightPart 2 of the Mexico Freight Playbook — a deep dive on how to actually sell Mexico freight, from finding opportunities in your existing book to closing deals outside RFP cycles |
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Apr 07, 2026 |
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| № 078 |
Why Mexico Freight Is the Biggest Opportunity in Brokerage Right NowThe full business case for Mexico freight — from why it matters to how to find shippers, build the team, and scale the department. |
|
Apr 02, 2026 |
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| № 077 |
The Builder's Moment: Why 2026 Will Separate the Founders from the FollowersAI 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. |
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Mar 26, 2026 |
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| № 076 |
Stop Being a Basic BrokerageTechnology is how you survive. Expanding into niches is how you become impossible to replace. |
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Feb 05, 2026 |
↗ |
| № 075 |
The Age of Builders and DoersHow a small group of operators, plugged into AI agents and modern tools, can tap into effectively unlimited scale. |
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Jan 12, 2026 |
↗ |
| № 074 |
Good, Better, BestNever let it rest! Until your good gets better and your better gets best! |
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Dec 29, 2025 |
↗ |
| № 073 |
Mexico Freight Is Hiding in Your Book — 3 Ways to Find ItYour customers already have Mexico freight. You just haven't asked yet. |
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Dec 17, 2025 |
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| № 072 |
Oh the shippers you'll findLet's do a deep dive on the types of shippers out there. |
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Nov 12, 2025 |
↗ |
| № 071 |
Building the future of freight collaborationHow we’re rethinking how brokers and carriers connect on Mexico and Canada freight. |
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Nov 06, 2025 |
↗ |
| № 070 |
Pouring one out for CanadaWhy brokers need to start thinking north while everyone else fights over U.S. freight |
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Nov 03, 2025 |
↗ |
| № 069 |
Five Tips to Grow Your Mexico and Canada BusinessPractical, high-impact moves to kickstart your Mexico and Canada business this week. |
|
Oct 30, 2025 |
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| № 068 |
Cargado isn’t your father's load boardOnly 60% of marketplace activity is spot freight — the rest is recurring lanes and projects fueled by Cargado’s live market intelligence. |
|
Oct 15, 2025 |
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| № 067 |
It might be time to fire your Mexico or Canada leaderStop paying people to dial for dollars and waste time on WhatsApp and LinkedIn covering freight when software can do it faster — and better. |
|
Oct 01, 2025 |
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| № 066 |
The Many Faces of Carriers in CargadoOh, the Faces of Carriers You’ll See — across the U.S.-Mexico border and Canada’s wide roads. |
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Sep 26, 2025 |
↗ |
| № 065 |
Driver Inc.: The Canadian Trucking ScamHow some Canadian trucking companies are cutting corners and cheating the system. |
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Sep 04, 2025 |
↗ |
| № 064 |
Mexico 101: What Makes It DifferentWhy fear of the unknown — not customs — is the biggest barrier to cross-border freight. |
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Sep 02, 2025 |
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| № 063 |
Issue #62: Clearing the Air on B1 Drivers, Worker Visas, and CabotageB1 drivers are not the enemy — they are a core part of North American supply chain! |
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Aug 22, 2025 |
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| № 062 |
Issue #61: The Seasons of ScalingBehind every neat growth curve is a messier reality worth talking about. |
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Aug 19, 2025 |
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| № 061 |
Issue #60: USMCA on the Clock: What Renegotiation Could Mean for Cross-Border FreightTrump’s Commerce Secretary says USMCA is next. For freight people, the real changes will be capacity-driven. |
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Jul 21, 2025 |
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| № 060 |
Issue #59: Takeaways from the 8th Annual Modernization of Cross-Border TradeA tactical recap of what we covered in Laredo—and the advice I’d give any broker trying to win in Mexico freight right now. |
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Jun 23, 2025 |
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| № 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. |
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Jun 09, 2025 |
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| № 058 |
Issue #57: The Board Meeting Playbook for StartupsA practical guide for founders and operators on turning your board meeting into a working session — not a performance. |
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Jun 02, 2025 |
↗ |
| № 057 |
Issue #56: Building a Superstar Leadership TeamThe best leaders aren’t building their résumés — they’re building something that matters. |
|
May 19, 2025 |
↗ |
| № 056 |
Issue #55: Building the Mexico Carrier Network of the FutureWhy our human-led, tech-enabled approach gives brokers what they need — and carriers what they want. |
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May 12, 2025 |
↗ |
| № 055 |
Issue #54: Why Mexico, and Why NowNearshoring is accelerating. If your customers are moving freight in Mexico, you should be too. |
|
May 05, 2025 |
↗ |
| № 054 |
Issue #53: A Guide to Mexico Freight LiabilityUnderstanding the Risks, Insurance Requirements, and Best Practices for Brokers and Shippers to Protect High-Risk Cargo and Navigate Mexico’s Freight Security Challenges |
|
Apr 28, 2025 |
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| № 053 |
Issue #52: Announcing Cargado’s Series AAnnouncing Our $12M Series A: Building the Future of Cross-Border Freight |
|
Apr 07, 2025 |
↗ |
| № 052 |
Issue #51: How Auto Tariffs Will Break More Than They FixWhy a 25% tariff on imported cars could shake the foundations of U.S. supply chains, freight networks, and your grocery bill. |
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Mar 31, 2025 |
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| № 051 |
Issue #50: Beyond the Headlines: Why Mexico Tariffs Aren’t the End of Cross-Border FreightA Strategic Guide to Identifying Tariff-Free Opportunities and Growing Your Mexico Freight Business Under USMCA |
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Mar 20, 2025 |
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| № 050 |
Issue #49: The “MCA” of the USMCABridging Borders: The Flow of Trade Between Mexico and Canada |
|
Feb 24, 2025 |
↗ |
| № 049 |
Issue #48: Stop freaking out, it’s just a trade warTariffs, Trade Wars, and Why Your Supply Chain Isn’t Moving Overnight |
|
Feb 17, 2025 |
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| № 048 |
Issue #47: Freight in the Second Trump Era – Trade, Tech, and TransformationAs Donald Trump prepares to take office for a second time, it’s clear this presidency will look different from his first. |
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Jan 13, 2025 |
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| № 047 |
Issue #46: First-Time Founder FumblesWhat interim head coaches and first-time founders have in common—and how to avoid fumbling your leadership debut. |
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Dec 30, 2024 |
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| № 046 |
Issue #45: AI in Freight: The Right Role for TechnologyBefore 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 |
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| № 045 |
Issue #44: Life in Startup LandBean bags. |
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Dec 09, 2024 |
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| № 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. |
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Dec 02, 2024 |
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| № 043 |
Issue #42: A Car-gobble gobble thank you!Happy Thanksgiving to everyone who reads my newsletter and those in the Cargado community! |
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Nov 28, 2024 |
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| № 042 |
Issue #41: Founder Mode & Defining SuccessWe recently hit several milestones (including sailing past 100 customers) and landed some substantial accounts (getting us to over half of the top 10 brokerages). |
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Nov 25, 2024 |
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| № 041 |
Issue #40: Collaboration: The Key to Success Between Brokers and CarriersThis industry is built on relationships and doesn't happen without brokers and carriers. |
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Oct 21, 2024 |
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| № 040 |
Issue #39: What we're building and whyI'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. |
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Sep 23, 2024 |
↗ |
| № 039 |
Issue #38: Engineering in LogisticsI posted about this last week, but I figured I would double down on my thoughts around hiring. |
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Aug 26, 2024 |
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| № 038 |
Board MeetingsI remember when building Forager, I had a conversation with our Series A investor right after we closed our financing with his firm. |
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Aug 19, 2024 |
↗ |
| № 037 |
Issue #36: Back to Laredo and some panel topicsI’m on my way back to Laredo for the 7th Annual Reliance Partners' Modernization of Cross Border Trade, hosted by Mark Vickers, who had started Borderless Coverage originally. |
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Aug 05, 2024 |
↗ |
| № 036 |
Monthly Digest - JulyRead on for some Mexico resources and job opportunities with Cargado! |
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Jul 29, 2024 |
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| № 035 |
Issue #34: Five themes from a founders summitI spent most of Sunday at a founders summit that Ezra Galston of Starting Line organized in Chicago. |
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Jul 22, 2024 |
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| № 034 |
Issue #33: The Cross-Border Blueprint, Part IIBack in February, I wrote Issue #13: The Cross-Border Blueprint, which covered some of the first steps it takes to expand into Mexico. |
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Jul 15, 2024 |
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| № 033 |
Issue #32: ChatGPT and a new name for The Silver SubstackChatGPT didn't write this post but I wrote this post about ChatGPT. And we've got a new name for this newsletter. |
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Jul 08, 2024 |
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| № 032 |
Issue #31: Time off in MaineI decided to head to Maine with my wife and son and take the week of the 4th off this year. |
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Jul 01, 2024 |
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| № 031 |
Issue #30: Monthly Digest – JuneCoyote is being acquired by RXO as we approach the end of Q2. |
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Jun 24, 2024 |
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| № 030 |
Issue #29: Ops Life in FreightOperating freight isn't for everyone. I've done the job - I understand what goes into it. Let's dive deep on the topic. |
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Jun 17, 2024 |
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| № 029 |
Issue #28: Building the right culture in the freight industryI 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. |
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Jun 10, 2024 |
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| № 028 |
Issue #27: Sixty Days Post-LaunchWe'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. |
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Jun 03, 2024 |
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| № 027 |
Monthly Digest – MayAfter 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. |
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May 28, 2024 |
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| № 026 |
Issue #25: Cross-Border CapacityCarriers that service Mexico aren’t your average carrier. In fact, some cross-border carriers don’t let their trucks cross the border, just their trailers. |
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May 20, 2024 |
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| № 025 |
Issue #24: A conversation with a co-founderI talked to over a dozen potential technical co-founder candidates and Rylan ended up being the perfect person. |
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May 13, 2024 |
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| № 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. |
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May 06, 2024 |
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| № 023 |
Issue #22: Put on your carrier sales hat, shirt, and pantsThe 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. |
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Apr 29, 2024 |
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| № 022 |
Feedback LoopFeedback from customers can make or break your product. Read on for a deep dive on early product feedback loops. |
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Apr 22, 2024 |
↗ |
| № 021 |
Issue #20: Five Opportunities to Improve the Freight IndustrySome things in this industry are working, but they're not working great. It's time to build better tech for the industry. |
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Apr 15, 2024 |
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| № 020 |
Issue #19: What Drives a DriverIn seventeen years in brokerage, half of my time was spent focused on cross-border freight. The other half was mostly carrier sales-related work. Let's talk about what I learned during that time. |
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Apr 01, 2024 |
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| № 019 |
Issue #18: Our First Product LaunchWe're days away from our very first product launch. I went into what it took to get here so far and what's next. |
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Mar 25, 2024 |
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| № 018 |
Issue #17: Marketing and Brand Identity in the Freight IndustryMarketing can be hit or miss for companies in the freight industry. Most companies focus on shipper acquisition, ignoring carriers and potential employees. |
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Mar 18, 2024 |
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| № 017 |
Issue #16: Advice to an Aspiring EntrepreneurStarting a company can be incredibly difficult and isn't for everyone. Entrepreneurship can also be incredibly rewarding. |
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Mar 11, 2024 |
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| № 016 |
Cross-Border ComplexityU.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. |
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Mar 04, 2024 |
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| № 015 |
Issue #14: Building In PublicBuilding 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. |
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Feb 26, 2024 |
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| № 014 |
Issue #13: The Cross-Border BlueprintI 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. |
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Feb 19, 2024 |
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| № 013 |
Issue #12: Produce from MexicoWalking through a grocery store, you'll find a ton of brands with products made in Mexico. When it comes to the produce section, most of what you pick up will have a Mexico label on it. |
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Feb 12, 2024 |
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| № 012 |
Issue #11: The Freight Industry Is ChangingThe 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. |
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Feb 05, 2024 |
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| № 011 |
Issue #10: How freight gets across the U.S.-Mexico borderThere is so much complexity to cross-border freight. It's not just the language or the border, it's every part of the process. |
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Jan 29, 2024 |
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| № 010 |
Introducing CargadoI’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. |
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Jan 22, 2024 |
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| № 009 |
Issue #8: Security in MexicoCargo theft is one of the hottest topics in cross-border logistics. It's less daunting than it feels. |
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Jan 15, 2024 |
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| № 008 |
Issue #7: A Carta Porte Deep DiveTowards the end of 2020, Mexico introduced plans to roll out the Carta Porte 3.0. As of January 2024, we still don't have a fully implemented Carta Porte 3.0 but will soon. |
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Jan 08, 2024 |
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| № 007 |
Issue #6: How I got my start with MexicoI'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. |
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Jan 02, 2024 |
↗ |
| № 006 |
Christmas EditionA quick post on wrapping up 2023 and getting ready for 2024. |
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Dec 22, 2023 |
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| № 005 |
Issue #4: Supply Chain StartupsI'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! |
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Dec 18, 2023 |
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| № 004 |
Issue #3: Hecho en Mexico / Made in MexicoAfter a busy trip to Laredo, TX, I decided to cover what moves through this amazing border city. With only 250k people, it's so much bigger than the population would tell you. |
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Dec 11, 2023 |
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| № 003 |
Issue #2: Nearshoring is BoomingWith 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. |
|
Dec 04, 2023 |
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| № 002 |
Issue #1: Founder-to-Founder AdviceNow 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. |
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Nov 27, 2023 |
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| № 001 |
Introducing the Silver Substack.Ramblings about the intersection of freight and tech. |
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Nov 25, 2023 |
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