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by smartbear 1256 days ago
Great questions and discussion, thanks!

Answering the last bit: "What about those ideas ... which carry a significant risk, but also could yield a significant reward?"

This is perhaps the key question for developing any strategy. This dilemma is not limited to this one exercise! It's the classic "risk/reward" question.

There's a lot of literature on this, some of which is conflicting (of course!). One common example is "Three Horizon Planning," which (I'm bastardizing it for the sake of simplicity) asks you to separate work/projects/ideas into three "future horizons": H1=running the business, zero-risk stuff you know is useful, selling the same product to the same customers; H2=new products sold to the same customers and market, so more risk but more reward; H3=new products sold into new markets, new customers, so maximum risk but also maximum reward, potentially entirely new business units. So for example, Google optimizing search is H1, Google adding "Diagrams" to the suite that already contains "Docs and Sheets" is H2, and Google launching GCP or buying YouTube is H3. Then the idea is that you should have proportional investment in these areas; for example 70/20/10 on H1/H2/H3. Finally, you want different processes and expectations for each thing, since "stuff we should be able to predict" should not carry the same expectations as "stuff with high variance that we cannot predict."

Another rule of thumb I like is to find bets that are very asymmetric, i.e. the potential upsides are orders of magnitude larger than the potential downsides. The stock market or VC works like this, because the most an investor can lose by buying stock is 100% of the investment, but there is no limit to the upside. If possible, you'd multiply those by the probability that they occur, but in my experience, we're all very bad at knowing the probability. :-) So, maybe not so much about the specific numbers, but the broad notion that one should be _orders of magnitude_ larger, not just a little larger -- that's something which should be apparent even without a lot of analysis.

In any event, this is a great question, and it's important for any strategic thinking, not specifically connected to this exercise.