Learning about project management from Undercover Billionaire

Yoyo Yuan
6 min readMar 24, 2022

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How do billionaires think and lead?

In the documentary Undercover Billionaire, Glenn Stearns takes on the challenge of creating a million-dollar business from scratch in 90 days.

“Scratch” means: He is flown to a random city (Erie, Pennsylvania); given only a pickup truck, a phone and 100 and isn’t allowed to use his real name.

The entire documentary is full of wisdom. Here we’ll focus on leveraging experts and leading a team under pressure.

Leverage experts

As a bit of background, here are three sources of revenue for the final created brand, “Underdog”.

Glenn consults experts as soon as possible. Starting from the ideation stage, he asks the local small business development centre about which industries grew the fastest in Erie in recent years.

He visits the local coffee shop and beer restaurant to discover problems before jumping into an industry.

Glenn also recruits good players for his team: Those who believe in the company, who can fight hard and have expertise.

Expertise can save weeks of going down the wrong path. Efficiency especially matters in charity because it can prolong suffering.

Well-intended and reasonable programs fail because there are hidden assumptions about people and local conditions.

For example, the Gyandoot program in Madhya Pradesh, India intended to make government services accessible by setting up computer kiosks in villages.

However, as local conditions weren’t considered — Electric power and connectivity at the village were too poor for good computer kiosks — it was a flop.

There are many other failed charity programs. To launch effective programs, we should be willing to change our minds amidst the excitement. There should be pilot projects and feedback from locals, or experts before implementation.

Another instance of ineffectiveness is the seal hunting campaign by the Inuit.

Seal hunting is the main economy of the Inuit. When seal products were banned by the European Union in 2009, the Inuit population further suffered from food insecurity and increased suicide rates.

As they campaigned, they wondered why their voices weren’t heard. This is partly because, in the early stages, the Inuit directly jumped onto an idea suggested by a fellow Inuk — e.g. posting seal hunting pictures with #sealfie on Twitter (not the best idea) — instead of asking for best awareness strategies from campaigning experts or talking to an out-group person about blindspots.

Managing teams under pressure

Myth #1: People are more likely to listen when you assert your opinion, especially when you sound strong.

Myth #2: Logically disproving someone could always change their minds.

How to motivate

Glenn pushes the team members under stress by first “tapping into the herd mentality” and then leading. Note how Glenn calls them out but he never bashes team members.

Example

Glenn hasn’t heard from a team member for a month and now speaks to them in person.

Glenn: Memorial Day weekend is our big push. Do you have a plan for the website and social media?

Chris (paraphrased): Not really sure yet. But I just need a logo and a paragraph about us, so I can start posting.

Glenn: So, I think since you’ve taken that leap from employee to an employer, you’re gonna be on your own (Empathizing). If you’re the employer, you’re gonna be the self-starter — the leader. You can’t be the follower; You’re the one that I said do all of it, from website to social media (Goal); You can’t wait; You have to be aggressive; You called me one time during the last month (Calling them out); You don’t know what our logo is. That is not being aggressive.

Social facilitation

When Dawn isn’t as enthusiastic, Glenn calls in everyone for a meeting: the effort that everyone is putting in motivated her.

Authenticity

Glenn sounds authentic when he motivates since he is already optimistic. (More about this next section).

Near the end, a member asks why he chose Erie. Glenn says he asked the pilot to deliver him to any city with the potential for a million-dollar business. It is authentic praise.

Mindset during conflict

When setbacks happen, Glenn is sure they can be improved. In psychology jargon, he is a person with a positive explanatory style who views causes as external, specific and situation-unstable.

Let’s see an example.

During rib fest, a 4-day event where Glenn’s team Underdog Barbeque sells smoked ribs, they repeatedly run out of ribs.

Christine, who Glenn tasks with inventory, insists it is impossible (global) that she knows (internal) when the inventory is going to run out. It is our first rib fest, she explains, implying nothing is perfect on the first try (situation-stable). “He is so infatuated with his inventory!” She says to another team member.

Her ego gets in the way, causing overwhelming stress for her mistakes. She leaves halfway and misses out on further networking opportunities, or Glenn’s identity reveal on day 90.

Meanwhile, Glenn explains it as:

Due to miscommunication (external, specific, unstable), Christine wasn’t in the frame of mind to get the importance of taking responsibility.

Though Christine starts yelling, Glenn never states “you’re wrong” and always says, we need to communicate more.

Likewise, when RJ rages at the delivery people, Glenn again empathizes and leads. He says, “father to son conversation”, and told RJ not to get angry with these delivery people because it won’t do us any good.

Lastly, Glenn knows pushing team members is necessary under a short timeline and setbacks are bound to happen. Instead of constantly apologizing, he says: I know I threw a lot at you. I just want to see you succeed.

Being concise

When one of the brewers rejects Glenn’s offer to pour beer into the restaurant, Glenn thinks that “no” is just the start of the conversation; Problems can usually be attributed to confusing communication.

Thus, Glenn polishes his elevator pitch and returns to the brewer. He stays concise while talking about a win-win game.

Some phrases used are:

  • I like to pick up where we left off.
  • I know your concern, however —
  • We threw a five-year plan at you. However, we’d still like to maintain a relationship with the local brewers.
  • You brew, I brand, we profit

Likewise, bad news should also be delivered concisely to avoid re-explanation and spending emotional energy.

Example

Glenn: We’re not gonna be opening on memorial day weekend. Here’s why…

Recap

The next time you PM, or simply just experience life, keep the following in mind:

  1. Leverage experts early
  2. Empathize and motivate; don’t bash
  3. Don’t let setbacks kill your confidence
  4. Concision for pitching and bad news

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Yoyo Yuan
Yoyo Yuan

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