Four Ways to Hustle at Startups with No Skin in the Game: Part II

I had dinner with my boss earlier this month and we had a very insightful discussion. We come from very different worlds.

Most of the guys at the office come from banking backgrounds. He gave me a useful perspective on the corporate culture. Although the startup culture is inexplicably different, many in the startup world come from finance backgrounds, which is heavily influenced by corporate culture.

Here was his advice.


The word “everything” is not to be taken literally. It’s merely to illustrate the importance of perception. Perception can be your best friend or your worst enemy.

My boss told me a story of when he was starting out as an analyst for a Wall Street investment bank. He was obsessive about checking his work; triple-checking, quadruple-checking, a strict attention to detail. His co-worker on the other hand, was not as zealous and made quite a few errors in the first few months of his tenure as an analyst. He was perceived as sloppy and unreliable. This compromised his trustworthiness. A year later, his boss still has someone double checking his work. Fighting bad perception is a tough, uphill battle.

My boss on the other hand, was flawless. By being a perfectionist, he was able to gain trust quickly and was rewarded with more responsibilities and higher pay. When he eventually did make a big mistake, he was able to avoid severe consequences. This just goes to show the power of perception.


These three interrelated pieces of advice are especially important if you have no stake in the company yet. It’s simple yet effective, and although it sounds like common sense, it’s still worth mentioning.

The first advice is to make your boss’s life easier. Being proactive is a quality sought by many employers. Take on responsibilities that will free up time for your boss to focus on more important things. They also appreciate it when you do the leg work. It’s like getting the bases loaded for him to hit a grand slam.

SEE ALSO: Working for Startups with No Skin in the Game: Part I

The second piece of advice is tied to the first one: make your boss look good. Make sure the work you do reflects well on your boss. If you have a meeting coming up, do the prep work and more importantly, your homework. Make sure to pay attention to the details. You make his life easier and he looks good in front of clients.

The third piece of advice is to be a man/woman of his/her words. My boss said to me, “If you make it a habit to say you’ll do something and then do it, you’re already better than 90% of the population.” It’s so simple and yet effective. People will perceive you to be reliable and trustworthy and in turn, you’ll be given more opportunities to prove yourself. Keep doing this and you’ll be sure to move up the corporate ladder.


During dinner, my boss told me a story about a lumber yard. Apparently it was somewhat of an heirloom in the sense that it was a story passed down from generation to generation.

He first established the characters. There’s the CEO of the lumber company. He was in a situation to promote one of his employees to the vice president position. Enter the two candidates. One of them is a 10 year veteran in a senior position. The other one is a young manager; the one that ends up getting promoted. Of course, the veteran is furious. He felt he deserved the position on the account of his seniority. The veteran confronts the CEO about this matter.

The CEO listens carefully to the veteran’s objections, then responds.

“I’ll explain why,” he says, and proceeds to ask a series of questions.

“What’s in shipping dock five?”

“I’ll go check sir,” says the veteran.

He comes back and tells the CEO it’s douglas fir.

“How much is there?”

The veteran comes back a few minutes later and announces there’s three tonnes of lumber.

“Where’s it from?”

The veteran comes back a few minutes later and says it’s from the mountains up north.

The CEO tells the veteran to wait outside and calls in the young manager.

“I want to know what’s in shipping dock five.”

The young manager comes back a few minutes later and says, “There’s three tonnes of pressure-treated douglas fir from the ABC treatment centre. The wood came from an old-growth forests up north.”

The young manager demonstrated superior critical thinking skills. He was able to think for himself. He was able to discern what was truly important and provided the vital information. The CEO trusted him more to take on important responsibilities without oversight.


Here’s some advice not from my boss. Tony Hsieh, the CEO of Zappos, is trying to transform Las Vegas. He’s moved the Zappos headquarter to Las Vegas’ City Hall. He’s investing hundreds of millions of dollars in real estate, small businesses, education and culture, and funding for tech start-ups.

“Money is just a way for Tony to get to his endgame,” says Erik Moore, an early Zappos investor. “Money just doesn’t matter to him. If he only had a million dollars left, he’d spend $999,999 to make Vegas work. He would be just as happy with a dollar in the bank and being around people he cares about and care about him.”

Money is a means to an end for me, not an end in and of itself. Money takes care of survival needs which allows me to develop my skills to become indispensable. That builds scarcity and that makes me more valuable. If you think about it, being indispensable has a priceless quality to it.

Steve Martin the comedian once said, “be so good they can’t ignore you.” Make that your focus and the money will come.