From Impossible to Improbable: The Startup Art of Getting to Yes
Originally a thread on X/Twitter:
1/22: Building a successful #startup requires getting to “yes” every day. Unity of purpose paired with the right team and right incentives is a recipe for greatness. But sometimes getting to “yes” requires a #startup to conquer the “Impossible”. A thread:
2/22: A key commonality of all successful startups is that they’re really good at solving problems that incumbents aren’t able or willing to solve. Most big companies have created environments where decision makers are incentivized to minimize risk vs. manage risk.
3/22: Paranoia around what MIGHT happen is everywhere. Fear drives decisions around how to test new value propositions, products and services. Employees aren’t rewarded for pushing the envelope but are punished if they go to far. The incentive structure is biased towards “no”.
4/22: In contrast, startups are designed to push the envelope and take risk. Teams know that forward momentum is the only option and that failure to make progress could result in EVERYONE losing their jobs. Getting to “yes” allows the startup to continue fighting the good fight.
5/22: But there are problems that can’t be solved by simply putting the right team or right incentive structure in place. There are problems that appear to be “Impossible” to 99% of the world for any of a limitless number of reasons. But to the 1%, nothing is impossible.
6/22: I’ve had the pleasure to spend time with many of the 1% in my career (and might actually be one of them myself). What I find fascinating is how they approach “Impossible” problems. While each “Impossible” situation is unique, how the 1% approach them isn’t!
7/22: Technique #1: Start by proving to the team that the problem isn’t “Impossible”
A common trait of the 1% is that they’re able to shift the mental mindset of their teams from “Impossible” mode to “Possible” mode.
8/22: The easiest way to do this is to offer the team a really horrible or painful solution and use it as proof that solutions exist. Once the team internalizes that bad solutions exist they can stop thinking about the problem as insoluble and work on improving “bad”.
9/22: I’ve used this technique many times in my career and can attest to the tangible shift in attitude that comes from knowing that a solution exists. When forward progress matters, pain is better than standing still and teams will seek out ways of reducing pain over time.
10/22: It’s amazing how many problems can be solved with manual solutions and grunt work. It’s amazing how many processes can be automated after a customer base has been built. Living with your solution can be painful but at least it allows for forward movement.
11/22: Technique #2: Challenge established norms and look to rewrite the rules
Most “Impossible” problems are deemed “Impossible” as a direct result of rules and constraints that define how a business or industry works. The 1% have no problem challenging the rules.
12/22: It’s fun to see how many new solutions emerge once constraints are relaxed. Re-writing the rules of an industry or removing self-imposed constraints shifts the narrative from “Impossible” to “If we can make this specific thing happen then we have a solution”.
13/22: Incumbents typically see this as “cheating” but it isn’t. Challenging norms and slaying sacred cows can be uncomfortable if you’re in a position of power. But defying common wisdom and rethinking traditions, customs and rules can fuel invention and progress.
14/22: There are plenty of real world examples of companies that were built by challenging an industry’s rules, but one of the best examples that I think about all the time happened to take place in the fictional Start Trek Universe.
15/22: In Starfleet Academy, cadets had to take a test known as The Kobayashi Maru. It was a training exercise designed to test their character when faced with a no-win scenario. The objective wasn’t to win – it wasn’t possible. It was designed to study how a Cadet would react.
16/22: James T. Kirk took the test three times, but before his third attempt, he hacked into the system and reprogrammed the simulator so that it was possible to win. Some teachers thought this was cheating but Kirk was awarded a commendation for “original thinking”.
17/22: Technique #3: Convert the impossible to the improbable and then make the improbable happen
It’s amazing how many times a problem is labeled as “Impossible” when it’s actually just “Highly Improbable”. Staying in the game is the most important goal.
18/22: What’s important to internalize is that every time a step in an improbable path is achieved the odds of success improve. And just as important, the environment isn’t static and new options materialize every time a goal is achieved (however small).
19/22: In poker, sometimes it takes a “runner runner” to win a hand (2 unlikely cards in a row) and sometimes winning that hand leads to winning a tournament. All it takes is a chip and a chair to stay alive so embrace the improbable when it’s all you have.
20/22: Examples of this are everywhere. For instance, getting a meeting with an influential person in an ecosystem might not directly solve your problem, but they might know something/someone you don’t or be willing to make resources available that could be helpful.
21/22: The same is true with raising capital or landing an important client or getting an endorsement or even getting a law changed. I know of businesses that were days away from shutting their doors but never gave up and something happened that changed everything.
22/22: The TL;DR: Conquering the “Impossible” is what great Founders and Startup teams do. It’s the “stuff that stories are made of” and every success story encourages future Founders to internalize that “Impossible” is actually just a negotiable concept.