A key investment mistake was misjudging the length of the destocking cycle in the alcohol industry post-COVID. After a demand boom led the entire supply chain to over-order, the subsequent "hangover" period of working through excess inventory lasted much longer than anticipated, depressing prices and returns.

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Major alcohol stocks are down as much as 80% over five years, vastly underperforming the S&P 500. This is not a temporary dip but a secular decline driven by a confluence of factors: cannabis legalization, the appetite-suppressing effects of weight-loss drugs like Ozempic, and general health consciousness, creating a potential contrarian investment opportunity.

The Froyo industry's previous decline wasn't due to a lack of demand, but a surplus of supply. The business model—low-cost self-serve machines and minimal labor needs—was so attractive and easy to replicate that it led to oversaturation. The industry essentially became a victim of its own success.

Explosive growth after a Shark Tank appearance created a massive cash flow problem. The four-month lead time on inventory meant the company had to fund orders 8-10 times larger than their current bank balance, pushing them to the financial brink.

While generating massive demand is a goal, it creates significant operational challenges. Actively Black's initial success outstripped its supply chain, leaving revenue on the table and highlighting that fast growth can be as dangerous as no growth if operations cannot keep pace.

Contrary to common belief, the home goods sector is facing a more challenging period now than during the 2008 recession. The massive pull-forward of demand during the pandemic created an artificially high peak, resulting in a deeper and more prolonged subsequent trough that is harder for businesses to navigate.

After a costly mistake left him with thousands of extra units, Solgaard's founder learned a key inventory lesson. He advises founders to avoid overly optimistic forecasting and go lean on inventory. Being slightly back-ordered is a better financial position than being overstocked with capital tied up in unsold goods.

Prosperity breeds complacency, leading businesses to overspend and expand into non-core areas. This dilutes focus and creates vulnerabilities. In contrast, bad times force the discipline and process improvements that build resilient companies, exposing what's missing in the operation.

Callaway is selling Topgolf for $1B after paying $2.5B four years ago. This loss highlights that businesses booming due to unique pandemic conditions may not sustain that growth, creating significant risk for acquirers who buy at the peak.

The boom in tools for data teams faded because the Total Addressable Market (TAM) was overestimated. Investors and founders pattern-matched the data space to larger markets like cloud and dev tools, but the actual number of teams with the budget and need for sophisticated data tooling proved to be much smaller.

Today's DRAM shortage stems from the post-COVID downturn. Expecting weak demand, memory producers became conservative with capital expenditures and didn't expand capacity. This left the industry unprepared for the sudden, explosive demand for memory driven by the AI boom.