Deep Sea Fishing is Like a Startup

A couple weeks ago I went fishing in the ocean for the first time. I grew up fishing on lakes in the Midwest so fishing in the ocean was an extremely different experience for me. My brother-in-law, father-in-law and I chartered a boat for five hours just off the coast of Cape Cod and that’s where the similarities began.

We had a finite amount of time to do something we hadn’t done before and we needed to figure it out fast. The good news was we had help and went out with a gentleman by the name of Captain Ron. He was the Captain of a fishing boat called the Stray Cat and was glad to show us the way.

It may sound odd to compare fishing to a start up and I had no idea it would be similar, but as I was out on the water, it started to feel strangely familiar to me. Here’s what happened.

Iterate and Fail Fast

When we initially made our way out of the harbor, Captain Ron had us get started immediately. He quickly showed us how to troll and jig the lines in order to attract the type of fish we were looking for. We were on the hunt for striped bass and, just as with lake fishing, there’s a method to attracting them while trolling. Once he showed us, we were on our own. He was driving the boat and didn’t have time to hold our hands. He was just there for direction.

Within about 5-10 minutes, Captain Ron had seen enough at the original location we started and was ready to move. Just like a startup, we tested, gathered data quickly and found what we were doing wasn’t going to work and we needed to try something else.

I’ve never given up on a fishing spot that quickly, so it was great how Captain Ron helped expedite the process. This was lesson number one and it was exactly how a successful startup moves. Test quickly, gather data, and if it doesn’t work, move on fast.

Landing the First Fish

After Captain Ron had us quickly try several more locations to no avail, we took off to a location he felt confident we’d find our target. He was right. We found a sandbar a couple miles off the coast and began trolling without moving much due to high winds. Within a few minutes of being near the sandbar, we started slamming striped bass.

Captain Ron had his first mate help us change all our bait over to the same lures. We began catching a fish every couple minutes for about an hour and a half. Sure, many of them were too small, but it was awesome!

Finding that school of fish off the sandbar felt just like finding the first group of customers we found at our startup. We had put in a lot of work and it was starting to pay off. Not all of them were keepers, but just having the validation was a great feeling and it was fun as hell to bring them in the boat.

After we trolled for a couple hours, we moved to a spot where Captain Ron knew we’d catch Sea Bass. He was spot on. We hovered over a shipwreck and caught keeper after keeper. There’s not a chance we could have ever found a location like that without an experienced guide. Forgive the pun, but it was truly like shooting fish in a barrel. We continued to catch over a dozen Sea Bass as we finished our time on the charter.

Experience Makes a Difference

The biggest lesson of the day was how important Captain Ron was to the operation. We couldn’t have possibly had as successful of a day without his guidance. Yes, we could have figured it out over a long period of time, but like a startup, we didn’t have much time. Having him with us crushed the learning curve. I liken him to a venture capitalist or an outstanding advisor. We have several of both at Stitch Labs and they have helped us greatly accelerate our learning there, too.

When we started the day, we were all new to the process and on the clock. We had to test, learn and move on quickly in order to accomplish our goal in five hours. Captain Ron was the linchpin. Because of his help, we were able to have a feast of fish the following evening.

I thought a lot about Captain Ron, his experience and even his age. I thought about how those things can sometimes be viewed in Silicon Valley and beyond. The Valley is an interesting place. At times there are biases toward people having been in the game for “too long” or toward people who are “older.” I personally think those biases are bunk. It’s about finding the right people for the right job. Age has nothing to do with it and the right experience can be a great equalizer no matter what a person’s age may be, young or “old.”

Captain Ron has been fishing with people in the Cape for over 30 years. His experience is invaluable. He was the right guy for the job at the right time. I strive to always work with and hire people that are outstanding at what they do. He was one of those people.


If you’re ever in the Cape, I highly recommend looking him up in Hyannis. He’ll make your day a success! Thanks, Captain Ron.

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