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Two Hundred Nine Thousand Lost on a Tourism Marketplace

The Story

Before Mostly Metrics, CJ Gustafson and his wife spent three years and $209,640 of their own money trying to build a tourism marketplace. He wrote about the loss publicly in January 2023 (Source 1).

The product: “Think of it as Hotel Tonight x OpenTable x ClassPass. The idea was to bring live connectivity to an industry where 80% of bookings were still done using pen and paper, months ahead of time” (Source 1).

The funding source was personal: “The initial money came from wedding gifts, the rest from our house fund and paychecks. We moved out of a fancy high-rise and into my parents basement to plow our ‘rent’ money into the third-party development. During the tail end of COVID, we packed up the truck and moved our lives from the East Coast to Florida, where we could market to year round tourism” (Source 1).

He referenced the same loss on the What Worked podcast: “I had one company where I lost over $209,000 of my own money trying to build something in the tourism industry. And that didn’t work out” (Source 2).

The post-mortem covers ten specific failure modes. The ones that recur most often in his later writing:

On founding without coding ability: “There were 1,000 times I felt absolutely helpless, knowing what needed to be done, but not being able to jump in and fix it myself. I’ll never depend on a 3rd party dev as the main means of production again. We would have been better off finding a technical co-founder rather than outsourcing flexibility and control” (Source 1).

On launching everywhere at once: “We tried to launch tours in +20 states at once, but quickly found we didn’t have the time or budget to market everywhere… We honed in multiple times. USA ⇒ Southern USA ⇒ Florida ⇒ South West Florida ⇒ Tampa, Florida. Nail it at the (hyper) local level and build a playbook. If you are everywhere at once, you are really nowhere” (Source 1).

The same niche-down lesson became part of his What Worked advice years later: “Start extremely small. And that was a mistake that I made at my first company that I tried to start in the tourism industry. I tried to launch it in every state at once, that was stupid. I should have went and niche down to the South of the US, then to Florida, and then to Tampa within Florida launching it” (Source 2).

On sales as the founder’s job: “I hated cold calling. I hated walking into a scuba shop and nervously asking for the owner. I hated getting rejected. But I couldn’t hide behind a screen and work on strategy. I had to sell. A product without distribution is nothing” (Source 1).

The unexpected return on the failure was the newsletter itself. “It led me to start this newsletter, since I was learning so many business concepts and didn’t want to forget them. And I never would have developed the guts to put myself out there if I hadn’t been shot down by hundreds of tour operators, tourists, hotels (and even family members)” (Source 1). And: “I ended up landing my first CFO role at a venture-backed tech marketplace. Talk about unexpected outcomes… I finally found somewhere to apply my marketplace knowledge. And if I didn’t have this previous entrepreneurial experience, or this newsletter, it wouldn’t have been possible” (Source 1).

His own framing of the cost-benefit: “Does losing $200K hurt? Yes. Absolutely. But I also look at it as my ‘real world MBA’” (Source 1). And the moat-line that came out of the same essay: “If something doesn’t scare you, it’s probably not worth doing at all” (Source 1).

The Growth In Reverse deep dive captures the inverted lesson: “It’s funny that the thing that took the least amount of capital investment, it took a lot of time to start… like it’s funny that the thing that costs like no money to start other than buying a domain was the thing that took off the most, that all the stupid stuff I’ve tried” (Source 3).

Lesson for Creators

The failure that costs you cash and humility is the one that funds everything you build next. CJ paid $209K for a real-world MBA in marketplaces, sales as a founder skill, and the cost of trying to be everywhere instead of somewhere. He wouldn’t have started Mostly Metrics without the failure, and he wouldn’t have gotten the CFO job at a marketplace company without both. Most “overnight” creator stories are built on top of a write-off that the writer eventually frames as tuition. Constraints drive focus, distribution beats strategy, and the thing that costs only a domain is often the thing that compounds.

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