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.
Maine
This last week, I spent my time off in Maine with my wife and son. We went hiking on three different trails, climbing two hills that included rocks larger than any of us that our 3.5-year old was able to climb on his own, which is just insane. The kid loves hiking and wants to go every week. Hilariously, he can’t get down from a jungle gym where he can’t see the ground, but has no issue climbing up a steep hill. Ironically, the photos in this post are from our trip and are not ChatGPT-generated, in spite of what you’re about to read from me.
It was nice taking the week off and not being stressed about anything freight-related. We spent a couple of days in Portland, Maine before heading to Belfast, Maine, where we stayed at an Airbnb. The majority of our time, we hiked in Acadia National Park on Mount Desert Island while enjoying the 4th of July parade in nearby Bar Harbor. It was awesome seeing the mini Bison dry van and a mini Bouchard conestoga. Bison’s presence is prominent in Maine because the massive Canadian carrier, Bison, previously acquired the two largest carriers in Maine, Pottles and Hartt.
ChatGPT has its place in content
It’s no secret that I leverage ChatGPT for the images I use with my newsletter. However, I don’t use it to write the actual content. I’ve used it for research, in the past, mostly for getting data together, and always while checking the underlying references. So I decided to try using it to rewrite my LinkedIn bio. I recently fed all my newsletters into my ChatGPT to get a sense for my writing style and asked it to rewrite my bio in the first person, as if I wrote it.
It took about thirty iterations to get to the point where it is now (feel free to read it in my profile, I have no shame in admitting that I used ChatGPT to write that). I also wrote and rewrote several sections myself. It felt like one of the most productive writing sessions I’ve ever had, no offense to anyone I’ve written content with in the past!
What won’t work well is just dumping in something like “give me the top 5 reasons why nearshoring is exploding and where venture-backable technology investments are needed,” where you end up with the same LinkedIn post that I feel like I’ve seen twenty-five times, from freight people to aspiring entrepreneurs from outside the industry to venture capitalists looking to jump into the market, highlighting supply chain resilience, cost efficiency, trade agreements and policies (USMCA), environmental sustainability, and proximity to market. We get it – there’s a ton of opportunity with nearshoring but there’s still so much opportunity in logistics and supply chain overall, whether that’s in Mexico, the U.S., or even Africa.
As I partnered with ChatGPT to rewrite my LinkedIn bio, we added this section about my experience investing in and advising startups. I learned a lot from my time building Forager and have learned a lot in the past nine months building Cargado and I enjoy passing along those learnings to startups. The ideal intersection is someone really early in the process in a space that I have experience in (like logistics and supply chain) as I’ve been able to be the most helpful in that space, both with my experience and network. If I can help a startup skip six months of bad lessons learned to get to a better spot, I feel great about my contribution to their business.
One of the startups I’ve had an opportunity to work with is FreshX. Clay Curran and Lance Hackney are building the first marketplace for refrigerated LTL freight in the United States. I’m excited about what they’ve been working on as they spent a few months trying to broker reefer LTL freight before dealing with nightmares from bad paperwork, challenges around pricing, and claims from shipping damages. They decided to bail on brokering the freight and build tools to solve the problems they experienced. It’s been fun to watch them build their company out at such a fast clip and now that they raised institutional capital, I talked to them about some advice that I gave myself and my co-founder, Rylan, about taking on capital. I’ll share those thoughts here:
It’s not your money, it’s your budget to build the business and generate revenue.
Just because you have the money doesn’t mean you have to start spending it. Take your time with a plan and make sure you have the right people in place. I know it’s sitting there in your pocket, just burning a hole there, but just leave it until you actually need to start spending more of it. You’ll start to see signs of when it makes sense to ramp up hiring.
Plan on having the capital last longer than you think you’ll need it to last. Something always goes wrong that takes it longer to hit whatever milestone you need from an investor to fund an eventual next round.
Yes, it’s amazing to be able to raise money but don’t consider that your milestone and don’t celebrate like you just won the Super Bowl. Keep the expectations with your team that a funding event is necessary but that the excitement should come when you achieve business-related milestones, like landing key customers or getting to profitability.
Don’t wait until you only have three months of runway before you start raising, start when you have a year remaining so that you actually have leverage and don’t feel under the gun. That means you need a version of an operating plan that shows that money lasting 30-36 months, not just 24 months.
New name
I’ve purchased some fairly funny domains in the past, nothing crazy or expensive, but I bought one that I’ve thought about, on and off again, to use for my newsletter. I figured I would start by asking ChatGPT to suggest some ideas, while leveraging my experience, writing style, and everything else I’ve dumped into that machine. I got back this initial set of ideas. Seven is hilarious but obnoxious and I don’t love any of the other ones. I’m not trying to write a digital newspaper. See the list below:
Freight Forward with Matt Silver
Cross-Border Insights
The Logistics Lens
Freight Frontier
The Forager’s Dispatch
Silver’s Supply Chain Chronicles
Borderline Brilliant
Cargo Chronicles
Freight Focus with Matt
The Supply Chain Sentinel
I’ve never been great with naming things and it wasn’t easy to come up with Cargado. Forager just hit me because it was the nickname I received from a couple UPS executives who had overseen the Coyote acquisition. The nickname came from my ability to generate cross-border truckload opportunities from UPS customers for Coyote, which is why I used the name for my first startup.
When building Forager, we only ever had one term sheet for each round. We received so many rejections from VCs and it really takes a toll when you get that same feedback, over and over again. Thankfully, building Cargado, this hasn’t been the case. Taking those lessons learned from Forager and focusing on a different ICP has resulted in a totally different experience this time around when it comes to fundraising. This time around, I had to tell investors “no” and they had spent a lot of time doing diligence and researching our company. I thought it would be awesome having multiple term sheets, and it’s not bad, but having to let someone down that believes in your company is not that fun.
When I was receiving all those rejections during my time building Forager, I kept seeing the same phrase over and over “congrats on all the progress” before a familiar “but we’re going to have to pass for now.” So I decided to buy CongratsOnAllTheProgress.com, thinking I would use it for a newsletter one day. At some point, we’re going to move some of my Mexico-specific educational content over to Cargado.com and the content of this newsletter will shift to a heavier focus on the life of building a startup. So, I figured the new name for this newsletter should be CongratsOnAllTheProgress.com. Check out the new logo / banner below: