Heading West

Eliyahu’s life began many miles away from his corner office in the glass-walled North American Centre building located in Toronto’s northern urban district. Born in 1968 in Ukraine, he grew up in an era where Soviet Jews lived on edge, as systemic anti-Semitism dominated the country’s social, economic, and academic arenas. His parents, Josef and Ella Kholodenko, were just one of many Jewish couples considering emigration for the safety of their family.

“My parents knew that if we stayed in the Soviet Union, I would eventually be drafted into the Red Army,” explains Eliyahu. “Given the attitude toward Jews at the time, this was dangerous.”

An unsettling encounter sealed the deal. “I was a rambunctious child in school and often got into trouble,” Eliyahu shares. “I was five years old when my teacher called my mother and asked for a meeting to discuss my behavior. She asked my mother to bring my passport.” Ella immediately understood the meaning behind this request. Soviet passports identified the nationality of the passport holder and the teacher clearly wanted to confirm her suspicion as to Eliyahu’s nationality (i.e., that he was a Jew).

The realization that even their five-year-old son would be subject to anti-Semitic prejudice by his own teacher shocked Eliyahu’s parents into the recognition that they had to leave immediately.

In 1974, during an emigration window, the Kholodenkos left the Soviet Union, and after a short stay in Italy, headed for Toronto, Canada’s largest city, where Eliyahu was enrolled in public school.

Three years later, in what proved to be a pivotal development, Eliyahu’s maternal grandparents arrived as well. “My grandfather, Avraham Yitzchak Buntsis a”h, was brought up prior to the Revolution and attended cheder,” Eliyahu says. “He only spoke Yiddish for the first twenty years of his life. When he arrived in Canada and could observe Torah freely, he was rejuvenated. My grandfather insisted that I had to go to a Jewish school and even offered to pay for it from his meager pension. He gave me a foundation in Yiddishkeit and instilled a love for it. He was always b’simchah and filled with appreciation for the opportunity to be a practicing Jew.”

An Entrepreneur Is Born

After high school, Eliyahu headed off to the University of Western Ontario, where he pursued a degree in urban planning.

“I wanted to build skyscrapers in downtown Toronto,” he says. “The Reichmanns were my inspiration. They were openly Orthodox Jews who were defining the city’s skyline and reshaping its financial districts.”

But Eliyahu says, as the saying goes, “Der mensch tracht, un Gott lacht — man plans, and G-d laughs.” Hashem had other plans for him. Eliyahu graduated university in 1991, the worst possible year for an aspiring urban developer to attempt entering the market. Toronto’s real-estate market slowed sharply in 1991 as the recession in the early 1990s, combined with a global real-estate crash, led to rising unemployment, falling consumer confidence, and plummeting property values.

“I sent my résumé to every developer in the city and got zero offers,” says Eliyahu.

Concurrent with Canada’s economic recession, though, was another global shake-up, namely the fall of the Soviet Union. Mikhail Gorbachev, the president of the Soviet Union, introduced policies aimed at transitioning the rigid, centrally planned economy toward market-oriented practices. These reforms included loosening state control over prices and production, allowing limited private enterprise, and encouraging foreign investment.

“What really caught my attention,” he says, “was that in 1990, a Canadian opened a McDonald’s in the heart of Moscow — just one mile from Red Square.” The opening of this iconic establishment in the very center of the Soviet capital held great symbolic meaning. On opening day, more than 30,000 people lined up, many waiting hours just to try some coveted Western fast-food.

Eliyahu made a straightforward calculation. In Toronto, he had little hope for employment in a stagnated economy. He was Soviet-born, familiar with its culture, but Western educated. In these nascent stages of Soviet privatization of enterprise, he should be able to find a place for himself that would allow for opportunity and growth.

“I had nothing to lose,” says Eliyahu. “I was single and had no money. I figured, what’s the worst that could happen?”

This was also the dawn of the private computer era, and Eliyahu reasoned that as the Soviet economy modernized, the burgeoning alignment with Western standards would drive strong demand for such technology.

“The Canadian government was offering small, state-backed loans to support new private businesses and young entrepreneurs,” Eliyahu says. “I requested an appointment where I presented the personal computer concept, and I was granted a loan of $7,500.” With these funds, Eliyahu booked a ticket to Hong Kong, a major hub for electronics trade and distribution that exported PCs worldwide.

“I bought a computer in Hong Kong as an initial sample,” he recalls. “It was enormous. I then flew to Moscow where I hoped to sell it, with the dream of developing the business further.”

The computer did not sell. “What I quickly learned was that doing business in the Soviet Union was all about relationships,” he explains. “If I wanted to have any success, I’d better find the right connections.” At this point, the $7,500 was completely spent. Eliyahu was left with no money and no plan forward.

“I arrived in Moscow on Friday, August 16, 1991. On the following Monday, there were tanks in the street,” he says. Gorbachev was on vacation in Crimea, and a group of hardline communists who opposed his liberal policies and sought their reversal had taken advantage of his absence to attempt a coup.

State-controlled news suspended all programming so Eliyahu was very curious to learn of the goings-on himself.

“I was walking on the main street near Red Square when suddenly, the ground beneath me began to shake. I turned around and saw a column of tanks churning up the asphalt,” he remembers.

The coup failed, ending after three days. But a few months later, on December 26, 1991, the Soviet Union officially dissolved. Overnight, a union of 15 republics became 15 countries, distinguished by their own sets of laws, currency, language, and sovereign borders. Opportunity was knocking for the Canadian-Soviet maverick who was willing to take risks in the still-roiling region.

Sparks of Success

“Over the previous few months, I had met up with a group from Uzbekistan that was in the cotton business,” says Eliyahu. “Uzbekistan had been part of the Soviet Union but was now an independent country. Processing Uzbekistan cotton and distributing it to other countries in the region would now take significant logistics and coordination.”

Eliyahu got to work establishing a business model that would do exactly that.

“We found a factory in Moscow that would process the cotton,” he says. “We then located a factory in Ukraine that would take this cotton and manufacture medical clothing or other healthcare textiles, such as bedsheets or sterile fabrics.” The business saw substantial success.

At the same time, Eliyahu’s personal life was changing as well.

“I got married to a girl who was also born in Ukraine but grew up in New York. So my wife and I share a very similar background,” he relates. They settled in Kyiv where their business continued to flourish. And that was where Eliyahu got his first personalized reminder that there are values bigger than business.

“There was a freestanding building that we used as our office,” Eliyahu says. “Saturday wasn’t a workday per se, but we tended to go into the office to catch up on work. We would wake up late, head to the office for a few hours, and then go home.”

One Shabbos morning, they were sharply awakened at 6 a.m. The alarm system in their building had gone off and a police force was at the scene. Eliyahu quickly headed to the building, but a brief check revealed that there were no security concerns; it was a false alarm. Eliyahu and his wife returned home, perturbed by the disruption, but soon put it out of their minds. Life resumed as usual.

“The next week, the same thing happened, this time at four a.m.,” says Eliyahu. “And then the following week, it happened again. At some point, my wife said ‘You know, maybe this is a sign that we should stop going into the office on Saturday.”

“We decided to stop working on Shabbos,” Eliyahu continues. “We also stopped driving and instead spent the day going on long walks and relaxing. For a while, that was about it.”

But one mitzvah leads to another and shortly thereafter they decided to start keeping kosher.

“We found out that there was a shul in Podol, near Kyiv, where a shochet came once a week and sold freshly slaughtered chickens,” Eliyahu recounts. The Kholodenkos began visiting the shul to purchase kosher chicken.

Even as they saw financial success and some spiritual connection in Ukraine, when they learned they were expecting their first child, they decided to move. Eliyahu sold his business, and the family moved to Toronto.

Divine Dividends

Today, Eliyahu clearly sees how Hashem prepared him for the next phase in his life.

“In Ukraine, the only two English-speaking channels were the BBC and CNBC,” he says. “Because of the time difference, when I was finishing work, the day was just beginning in America. The early morning is always the most exciting time in the stock market. The bell rings, everyone is jockeying for position. Watching this from afar, I was really captivated.

“This was mid-’90s,” Eliyahu continues. “The Internet was just beginning. And day trading was becoming very, very popular. All of a sudden, you no longer had to invest through a middleman — it could all be done online.”

When the Kholodenkos settled in Toronto, Eliyahu felt that these conditions offered the opportunity he wished to pursue.

Concomitantly, Eliyahu discovered a wealth within Judaism he hadn’t known of prior.

“I started learning with Rabbi Levi Jacobson of Chabad West Thornhill,” he says. “I learned of the Rebbe and his incredible legacy, and Rabbi Jacobson taught me his Torah, which I found captivating.

“Shortly thereafter, I traveled to 770 [Chabad headquarters] and the Rebbe’s ohel [gravesite] in New York. It was an unforgettable and life-changing experience. I decided to make the Rebbe a partner in my business and committed to utilize a portion of the proceeds to spread Torah.”

These experiences led to a sharp shift in Eliyahu’s perspective in life and business.

“I began to see how Hashem’s Hand directs everything,” he says. “And I came to recognize that if life presents me with a ‘no,’ that’s a sign from Heaven that there’s a ‘yes’ to be found.”

Pretty soon, Eliyahu had to draw on these reserves of faith.

“I met with a Toronto firm that was selling day trading franchises and I made what I thought was a winning presentation of how I can become a successful franchisee,” Eliyahu relates. “They said no and I was very disappointed.”

But, as Eliyahu had noted, “no” means that the true “yes” lies in another endeavor.

“Their refusal propelled me to say, ‘Okay, I’ll have to start my own brokerage,’ ” he says. And this is how Questrade was born in 2001.

Things were looking hopeful — but then came 9/11. The entire New York Stock Exchange shut down for a week, and the market went into freefall thereafter. But by this time, Eliyahu’s emunah was unshakable. He knew with certainty that Hashem would take him through these challenges.

Climb Right Over

Eliyahu shares how an idea conceived by the Rebbe Maharash, the fourth Rebbe of Chabad, defines much of his life’s approach, helping him overcome challenges such as the post 9/11 economic crash.

“There’s a famous chassidic concept of the Rebbe Maharash on dealing with challenges,” he says. “The Rebbe teaches us: The world says, ‘If you can’t crawl under an obstacle, try to climb over it,’ but I say, ‘L’chatchilah ariber! At the outset, one should climb over!’

“Even in the most difficult moments, I didn’t panic,” Eliyahu says. “I davened, and when the pressure was on, I davened even harder. I would say Tehillim and go to the Ohel. Eventually, with Hashem’s help, I would formulate a plan to deal with whatever the issue was.”

On the wall of Eliyahu’s office hangs a sprawling, magnificent portrait of the Rebbe, his ever-present visage serving as a constant reminder of the values and priorities Eliyahu holds dear.

“The Rebbe teaches, ‘Your livelihood rests entirely in Hashem’s hands and it’s His blessing that brings wealth.’ Therefore, when a challenge comes, you have to turn to the Creator, the Source of all things and see where you can strengthen yourself,” Eliyahu says.

Eventually the economy crawled out of its downfall. Things progressed for the next few years, until they met another hurdle.

“When fast-speed Internet started to become available to private consumers at reasonable prices, our business model had to change on the fly,” says Eliyahu. Undeterred, Eliyahu contacted the titan brokerage firm Charles Schwab to lease a license for use of its leading day trading program.

Negotiations led to an unprecedented transaction: Questrade became Schwab’s only licensee in the world for its cutting-edge platform. This helped to catapult the company and attract the most active traders in Canada.

“Baruch Hashem, today we no longer rely on external technology,” Eliyahu points out. “We have since built our own proprietary platform.”

Questrade’s real break came — paradoxically — in 2009, in the aftermath of the great economic collapse of 2008.

“We watched as some of the most respected and established brokerage firms — Lehman Brothers, Merrill Lynch, Bear Stearns — suddenly vanished almost overnight. These were companies with which we had developed important connections because we relied on them as counterparties in the US market,” he says.

Their abrupt collapse caused massive disruption but also sparked an extraordinary surge in trading activity. With many traditional players disappearing, investors and traders were forced to seek alternative platforms and brokers — such as Questrade.

“We saw unprecedented growth,” Eliyahu relates.  “We doubled, then tripled our client base.”

Such rapid growth came with its share of challenges. The market volatility demanded heightened vigilance in risk management and constant adaptation of trading strategies.

We had to ensure our risk management systems were not only effective but robust enough to withstand the turbulent environment,” says Eliyahu. “Thank G-d, we navigated those times well.”

Man with a Plan

Today the company provides Canadians with low-cost digital financial products and services including investing, wealth management, mortgages, deposits, real estate, and banking. Eliyahu’s vision is to revoluntionize financial services for the benefit of Canadians by providing the most innovative and cost-efficient financial services online.

Eliyahu’s management style has also evolved. “We are blessed to have a very talented team that is fully dedicated to the mission. When you are fortunate enough to work with such consummate professionals, you should give them the autonomy and authority they need to succeed,” he says.

Smart delegation allows him to use his time and energy to work, as he words it, “on the business — not in the business.” As such, his days are spent evaluating strategy, finance, risk, and future growth.

The scope of his success hasn’t led Eliyahu to relax his religious principles — to the contrary, he’s grown stronger and more committed in his Torah learning and mitzvah observance. He attends regular shiurim in Gemara and chassidus.

He brings that same principled mindset to the office and sees his values-driven approach as the driver of all success.

“At its core, business is about one thing — helping people,” states Eliyahu. At Questrade, this philosophy is constantly reinforced. “We are here to help Canadians become much more financially successful. That mission is reiterated in our boardroom, our town halls, and in everything that we do.”

Eliyahu’s position allows him to help others outside of work, through the family’s many tzedakah commitments. Financial blessing allows the obvious opportunity to provide others with monetary assistance, but he also uses his life and business experience to lend advice to those looking to find their own opportunities.

“What I always tell young people,” says Eliyahu, “is that entrepreneurship is not for everyone. You need a certain mindset and a certain personality. If you think you’re going to be successful, you have to ensure that you will persevere.

“If you want to take this path, then know that there’s no Plan B. Some say, ‘Well, if this doesn’t work out, maybe I’ll try something else.’ I tell people: No. You’re either in or you’re not. If you’re focused on creating a Plan B — if you have one foot out the door — you’ve already lost before you started.”

One of the questions Eliyahu fields often is how to ensure that material success does not hamper spiritual growth.

“Chassidus teaches us that there is only one — everything is one. It’s all working toward one mission,” he explains. And that mission, says Eliyahu, is to take the gifts Hashem blessed you with and use them to fulfill His Will.

“If someone is blessed with financial success, and uses the money for the wrong things, he’s not doing what’s best for him. Not only is it negatively affecting your family and your community, he’s wasting his own potential.”

As Eliyahu leads me through the hallways of the stately office building, he smiles and chats with employees from different departments. The interactions are friendly and respectful. The humility with which he speaks reveals that Eliyahu takes nothing for granted, and attributes his bounty directly to Heaven.

“You have to realize that the success is not about you,” says Eliyahu “It could have been granted to anyone. But when Hashem chooses someone for a particular mission, it’s a privilege and a big responsibility.” This, he says, is the key message of Modeh Ani, the first prayer we say upon waking, which concludes with the words “rabbah emunasecha.” “Hashem has great faith in us!” says Eliyahu. “I find that incredibly inspiring.”

(Originally featured in Mishpacha, Issue 1082)