“My parents were poor,” he said. “Dad worked at a gas station; mom worked at a coffee shop. Whatever money my parents had, they put towards living in a nice part of town so I could attend better public schools. Sometimes, it was harder growing up in an area where everyone had money but I didn’t. It felt alienating.”

His parents valued education, which was instilled in Pirani from an early age. Even today, Pirani has a passionate desire to grow intellectually.

He spends his days absorbing as much information about markets, finances, and general business data as much as possible.

Which makes it all the more surprising to learn that he didn’t feel a structured school environment was his ideal setting for growth.

“I like to learn at my own pace,” he said. “My education in entrepreneurship came from making every mistake in the book, not through sitting in a classroom.”

Pirani started a handful of ecommerce companies while still in high school, making as much as $2,000 a week when he was only sixteen years old. After graduating, he attended the University of Texas at San Antonio for a single summer semester then dropped out.

“Academia wasn’t my thing,” he admitted. “I was driven to create wealth and couldn’t just sit in class. I’m glad I went that route.”

He added that, although he was making thousands of dollars in high school, the revenue from his businesses dried up by the time he turned eighteen. Without the finances to pay his college tuition, he was forced to drop out – albeit unregretfully.

Yet, Pirani is quick to advise others not to follow in his footsteps too closely.

“I wouldn’t recommend dropping out; that’s irresponsible advice,” he said. “If you can spend four years learning, especially when you’re between eighteen and twenty-two, there’s nothing wrong with that. That will serve you better than if you didn’t. Trust me, you won’t get this time back later in life. If I could have afforded it, I would have stayed because I think I would have learned a lot that would have helped me on my entrepreneurial journey. The life experiences themselves are valuable, too.

There’s value in learning, especially if you’re broke and eighteen-years-old. Don’t gamble with your life.”

Pirani might be one to celebrate his successes, but he’ll also be the first to share the hard lessons risk taking has taught him.

Risky Business

The short story on Pirani’s success is that he started multiple tech companies, made a couple successful exits in his 20s, and used the liquidity from those exits to invest in stocks using option-based strategies to get outsized returns.

The long story includes a few key details, perspectives, and failures that every young entrepreneur needs to hear.

“I worked hard very early in my 20s but I was probably working hard for the sake of working hard,” he admitted.

He noted how, in one of his companies, he thought that it was necessary to have an employee manning the phones during evening hours. Instead of hiring, he decided to take the responsibility upon himself.

“I was doing 18-20 hour days, sleeping in the office or at my desk,” he recalled. “I was doing three or four people’s jobs while my friends were partying and having fun.”

Though he wouldn’t go back and change his decision, he concedes that he would have slowed down and focused on ways to work smarter, not harder.

“People in their 20s don’t understand the value of youth,” he said. “You’re rich in time at 22, which is arguably worth more than money.”

Pirani now believes that working hard isn’t always the best way to operate. Instead, he feels that slowing down and strategizing allows him to make clear decisions. “My core focus has transitioned from hard work to strategy,” he said. “As an investor and CEO, I need a lot of white space and mental clarity to make the right decisions.”

He admits that his wealth provides him with an opportunity to open himself up to failure. This wisdom allows him to take risks that he wouldn’t have earlier in his career.

“I once felt obligated to hold certain meetings or micromanage because failure was a scary thought,” he said. “Now, I don’t feel the need to keep my hands on everything because I worked my way into a position where I can only fall so far.”

That doesn’t mean Pirani has always sat in a comfortable seat. He mentioned that he made a lot of mistakes over the years, especially in the market with options trading.

Mistakes that cost him millions of dollars.

“I was nearly wiped out in my 20s because I was levered,” he said. “Leverage is the number one way to lose money in the market. I lost 80 percent of my wealth because I was levered and now I never use leverage without appropriate hedging”

Working With Strategy, Not Hardships

What does a normal day look like for Fiyyaz Pirani?

It’s far from glamorous.

He isn’t watching the money roll in from the top floors of a skyscraper nor is he conducting business from a swanky yacht. Instead, Pirani can be found in his home office, pacing away on the phone, which is exactly the way he wants it.

“Your environment needs to be right to be productive,” he said. “On my Instagram, I might show the flashier side of my life because that’s interesting, but no one wants to see me pulling my hair out on a red day.”

He agrees that the skewed impression that many successful entrepreneurs promote on social media hides the mundane activities and daily frustrations that sustain success.

On any given day, Pirani starts his morning with a pre-market meeting to check his open positions and catch up on market news. He limits his time spent in additional meetings, preferring to spend his hours focusing on in-depth research and analysis.

Is Pirani still putting the pedal to the floor and his nose to the grindstone for endless hours each day? Far from it. In fact, he believes that the concept of hustle culture makes no sense.

“There are two camps right now,” he explained. “One tells you to pursue wealth at all costs and work twenty hours a day. If you’re just constantly working, it’s hard to think. You need to slow down to make high quality decisions. It’s better to make two or three high quality decisions a day than dozens of degraded decisions.”

He continued: “The other camp says you should aspire to live the four-hour workweek by putting in as minimal effort as possible and automating your business. You need a lot of capital to do this successfully, and if you’re against hard work on Day One, then success is not going to happen for you.”

Instead, Pirani says it’s vital to find the middle ground. Eating right, sleeping, and spending time with friends and family is crucial because operating from a cool, calm and collected perspective allows you to make higher quality decisions for your business and your life.

On the other hand, he also admits that being a business owner means always devoting a portion of your headspace to your work. He believes that as long as these thoughts don’t create undue stress or anxiety, then you’ll develop an excitement for getting back to work and overcoming your challenges.

“If you want to turn your brain off, get a nine-to-five job. But if you want to be a successful entrepreneur, you need to understand that your responsibilities don’t end at five o’clock.”

While Pirani has goals of growing his hedge funds to a billion dollars in the next decade, he cautions entrepreneurs who are chasing money as the key to happiness.

“Money is weird,” he said. “You never have enough even when you have so much that you can never spend it all. The goalposts keep moving during your journey and there’s always another mountain to climb. To think that you’ll gain happiness once you earn a certain amount doesn’t make sense.”

If there’s one lesson entrepreneurs should take from Fiyyaz Pirani’s journey, perhaps it’s that education and money are merely tools, not tickets, for success. Income can be gained and lost. Education can be applied correctly and incorrectly.

Maybe the phrase “work smart, not hard” is better rewritten as “work with strategy, not with hardships”. Fiyyaz Pirani proves that the road to becoming a Self-Made Man is filled with successes and failures, but with a calm perspective and a clear strategy, wealth can be achieved no matter your education level or financial background.

Advice Allocated From a Self-Made Man

How do you stay motivated to continue growing your businesses and hedge funds?

I don’t think that success or hard work comes from a place of motivation; it comes from discipline. It’s difficult to be motivated all the time. I don’t want to work some mornings, but no matter how much of a garbage day I’m having, I get up and I do my job because I have discipline. I have goals and responsibilities, two things that rely on discipline for success. The most important attribute of a man is to control his emotions and his mental state. If you’re supposed to be thinking about work or a problem, and your mind wanders, then you need to have the discipline to keep your head in the game. You’ve got to be able to snap out of it.

What advice do you have for someone in their early 20s who still is unsure about what to do with their career?

Whether or not you went to college, figure out what you’re good at and focus on that. Everyone has at least one skill that they’re good at and enjoy. The key is to figure out how to turn that skill into value for others then into wealth for yourself. In my 20s, I was good at building tech businesses and software. It wasn’t until I was older that I learned how to be successful in finance.

Do something you enjoy; you’re going to have a tough life if you don’t. It’s really hard to be successful at something that you don’t enjoy doing.

Do you have any advice for someone in their early 30s facing the same situation?

If you’re in your early 30s and don’t enjoy what you’re doing, you’re running out of time. I would quit my job and switch career paths, even if that means making less money. Money won’t make you happy. I’d rather go all-in on and fail than live my life not trying. In high school, I volunteered at a hospice center. My job was to simply talk to the people there and it was an enlightening experience. When I asked what their regrets were, no one ever said they regretted taking a risk. It was always the opposite. They regretted staying too long in something – like a career – that they didn’t love.