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I share what I learn each day about entrepreneurship—from a biography or my own experience. Always a 2-min read or less.
Posts from
August 2026
A Few Shipping Lessons I’ve Learned
For the last few weeks, I’ve been helping a friend scale his start-up. His company sells its own branded physical product. One of its biggest pain points has been logistics; specifically, shipping companies picking up and delivering products undamaged and on time. If you don’t have room for error, then a small shipping issue can ripple and cause much larger problems.
I’ve dealt with lots of shipping companies, and I saw them make all kinds of crazy mistakes when I was running CCAW. Over the years, I learned a few things:
- Things are going to happen. When they do, learn from them and try to identify ways to prevent them in the future. Document those learnings somewhere.
- Processes for dealing with shipping companies make resolving errors more efficient and help get things back on track faster.
- The cheapest shipping company isn’t always the best choice because you’ll pay for the money you save with time and energy.
- There’s a big difference between small-parcel (e.g., UPS and FedEx) and less-than-truckload (LTL) shipping. LTL is like the wild, wild west. Small-parcel networks are highly tuned systems built by industrial engineers. LTL networks, not so much.
- Check your bills. Overbilling is rampant in the shipping industry.
- Shipping to consumers and small businesses is very different than shipping to warehouses and distribution centers (DC). The latter have lots of products and trucks coming and going, so it’s hard to get a clear answer on the status of a single shipment. If you’re shipping to a warehouse or DC, it’s helpful to understand how the location operates before you ship there. Some require appointments or other extra steps.
- Small-parcel shipping has historically been a duopoly with FedEx and UPS, but that’s changing now with Amazon Shipping and other last-mile service providers.
- The cost to ship to a residential address is very high, which historically has made it prohibitively expensive to ship certain types of products to residences. Amazon Shipping and other service providers are changing this as we speak, though.
- If you’re shipping a material number of packages daily, a central system where you can see the status of all shipments across all carriers and locations is crucial. Separate systems that don’t talk to each other create chaos and make it difficult to scale and run a smooth operation.
- Labeling and preparing shipments properly can help prevent 50% of issues down the road.
That isn’t a comprehensive list, but if you address everything on it, you’ll drastically increase your ability to scale and the chances that you will scale, and you’ll catch and fix issues faster, prevent issues, and save on shipping expenses.
What I Learned Last Week (8/2/26)
Continuing with my new protocol, here I’m going to share content I consumed and learned from. Last week, I spent time doing general learning about a variety of topics.
What I consumed last week and what I learned from it:
- Test packaging and product names before you create the product – YouTube interview with performance marketer Jason Kutasi. Very interesting. Good take on performance marketing from someone who’s been in the trenches for over a decade. I enjoyed learning the history of performance marketing on platforms like Yahoo and Meta. The most interesting thing in this interview was Jason’s framework for testing new ideas, like packaging and product names, using cheap Facebook ads before the product is created. Saves a ton of time and can be done for a tiny amount of money. The winner is the packaging/name with the lowest cost per lead. The other thing that stood out to me was the importance of getting the timing right on new advertising platforms.
That’s what I learned from what I consumed last week.
My Experiment With Grading Every Workday
A little over a month ago, I began testing a one-page daily report card. Learn more about the idea and my experiment here. I now feel that I have enough data to evaluate this experiment and what I’ve learned from it.
I’ve decided that I like this habit. It feels like a natural extension of my blog-post habit that’s focusing on daily execution. Starting each day by detailing what I want to get done and ending the day by listing what I actually did has helped illuminate the gap between the two every day, which helps me recalibrate for the next day. The sections on mistakes and lessons learned are useful because they force me to stop and think about what I did wrong (no shortage of material there) and what I learned from those mistakes. Reflecting on this daily has led to insights that have helped in my daily recalibration. Grading my time in two-hour blocks has surfaced patterns that I might not otherwise have noticed.
Overall, this habit is a way to create an accelerated feedback loop on how I work. I’m evaluating myself and reflecting every day, which lets me make micro changes every day. I can see how making small improvements daily (e.g., 1%) would compound to big changes over a longer period.
Will it become a long-term habit like this blog? Time will tell. It’s still an experiment, but right now I’m getting value from it, and it’s challenging in a fun way.
