Founder Psychology: The High Ground Maneuver

One may be the greatest entrepreneur of all time. The other is Steve Jobs.

I’ve got two stories to share.

One involves arguably the greatest entrepreneur of all time: Steve Jobs. The other involves a somewhat less notable entrepreneur (but he’s only 19 so the jury is still out): my younger brother Tiger. The purpose of these tales is to illustrate a powerful psychological counter: the high ground maneuver.


First: Steve Jobs. Eight years ago, Steve introduced the iPhone 4. This was an important product for Apple. The smartphone wars were just starting to heat up, and Apple was feeling the heat from both Android and (believe it or not) Blackberry. I had just quit my job to work on my startup full time, so I distinctly remember the iPhone 4 launch because it was the main reason I switched from Android to the iPhone. The phone was gorgeous, resembling more of a classic timepiece than a tech gadget. This was a time before “best iPhone we ever made” became a meme and every iteration seemed like a quantum leap over its predecessor.

A few days after the launch, disaster struck. Reports surfaced that holding the new iPhone a certain way would kill reception. Users were outraged. Bloggers heaped ridicule on Apple. It appeared that Steve’s famous reality distortion field had crumbled. Any other CEO would have gone into crisis mode and hired a PR firm to put out the fire. They would have issued a public apology and made a hollow promise to “do better next time”. Not Steve. He called a press conference and personally spoke to the media. He didn’t apologize. He didn’t explain. He didn’t do anything a PR firm would have recommended. His response? “All phones have problems.”

Mamba Mentality

Now onto my cofounder and younger brother: Tiger. Entering his junior year of high school, his goals were a bit different from his classmates. While they were busy studying for the SATs and applying to college, he was applying for a full time software engineering job. Why? Because for as long as I can remember, Tiger always had a mamba mentality. Kobe Bryant was his favorite player, and like Kobe, he had a pathological drive to succeed and win. I first noticed this at an early age, when I invited my college friends to play Scrabble and Tiger beat all of us so soundly he felt bad and started to help us instead. Two details that illustrate the ridiculousness of this situation. One: Tiger was five years old at the time. Two: The first game was so lopsided that my friends and I decided to play on the same team to take him down. Yes, you read that right. Six 20 year old Cal students colluded against a single five year old and got demolished. If memory serves, he quadrupled our score. That was my brother in a nutshell. His work ethic and competitiveness were so extreme that our asian tiger parents actually pressured him to stop working so damn hard!

With that in mind, it’s no surprise that Tiger wanted to follow in the footsteps of his idol and skip college. For Kobe, the goal was the NBA. For Tiger, it was a software engineering job at a tech company. I recall talking him through his decision at the time. Our parents thought he was nuts. I tried to be encouraging, but in the back of my mind I didn’t really think he had a shot. Silicon Valley tech companies routinely reject the best and brightest computer science grads from Stanford and Berkeley. What chance did a 16 year old have? It was a slow start, but sure enough offers started to come in. At first part time, then internships, then full time lowball offers. Then one day Tiger texted me and I almost dropped my phone in disbelief. PayPal had made him a full time offer to join the Braintree core payments team. His compensation was higher than what I paid my college grads at Yahoo. I was floored to say the least.

How did he do it? I’ll let him explain in his own words here, but in a nutshell he turned his youth from a perceived weakness into a strength. It was a perfect example of controlling the frame. Tiger’s message to potential employers was “Youth = high energy”.

Taking the high ground

The high ground maneuver is not about morality, or taking a holier than thou attitude. Simply put, it is the process of taking an argument out of the weeds and onto a higher plane where everyone is in agreement.

Have you ever been in a political argument online? Most of the time, it turns into mutually assured destruction due to confirmation bias (which is a post for another time). The only way to get out of the weeds of such a discussion is to zoom out and find common ground that is impossible to argue with.

Steve Jobs did this with “all phones have problems”. Everyone knows this to be true, but once Steve said it, the situation was completely diffused. All of the details of why antenagate was or was not a big deal evaporated and everyone started looking at other phone manufacturers to see if Steve was right (which of course, he was!). Antennagate articles essentially disappeared overnight.

Tiger’s high ground maneuver was “youth = high energy”. When an employer looks in the weeds there are a lot of reasons not to hire a high schooler. But by associating his youthful brand with energy, he became the youngest engineer in PayPal’s history.

Notice that the two statements I highlighted are simple and vague on purpose. A high ground maneuver cannot be complex or specific, because that invites critical thinking. The goal is to end the logical argument by appealing to emotion.

So when can you use the high ground maneuver? It’s best used when a logical argument is likely to end unfavorably for you or in a stalemate. It’s a psychological Ctrl + Alt + Delete. It’s also important to note that this is not for winning arguments, but rather for ending them with minimal bloodshed. As an early stage entrepreneur, logic is not on your side. Almost anything involving logic will not withstand critical scrutiny. When you are pitching investors, you are selling a dream. When you are talking to customers, you are selling a potential future. When you are recruiting employees, you are crafting an idealized scenario that likely won’t pan out. In each of those cases, the logical answer will always be no. To get to a yes, your best option is the high ground maneuver. For example:

Investor: we would love to invest but your metrics are not that attractive

The trap here is to justify your metrics. This is a mistake! What you should say instead is:

You’re right, our metrics are not where we want them to be. But we are a small, nimble company with capable founders and we will outmaneuver our larger competitors. And with your help, we can take that journey together. Imagine looking back at this day when we go public!

See what we did there? We moved from the weeds (metrics) to a point that’s inarguable (small companies are more nimble). We also invited the investor into an epic adventure. Who doesn’t love that? Finally, we helped them think beyond the sale (which is another post for another time).

If you doubt the effectiveness of this tactic, pay close attention to the next time you witness an argument. How does it end? Is it because someone has superior logic? Or is it because someone appealed to higher ground?

I usually like to avoid politics but the political realm is ripe with examples of the high ground maneuver. To avoid bias I’m going to use one example from each side.

When Barack Obama tried to pass his healthcare plan, the debate was in the weeds: premiums, pre-existing conditions, long term budget projections, etc. How did Obama cut through the noise? “Americans are dying unnecessarily due to poor healthcare. We need to do better”. BOOM. High ground maneuver. Bill passed.

Several months ago, Kanye West voiced his support for President Trump. The internet erupted. Did Kanye get into the weeds of policy and defending Trump’s many transgressions? Nope. What did he say (check his tweets if you don’t believe me)? “There is so much hate right now in this country. Why not try love?” BOOM. High ground maneuver. Media uproar diffused.

Now, I’m well aware that both of these maneuvers didn’t change a lot of minds. Everyone I just mentioned is still highly controversial (as is the nature with politics, which is why it makes such a great example). But in both cases the national debate was effectively nerfed.

So, next time you find yourself battling in the weeds, stick your head up and seek higher ground. You might be surprised at the result.