Alkarim Jivraj and the price of keeping control

Nancy Peterson had built a business she wanted to keep. HomeStars, the home improvement review service she founded in 2006, needed money to grow. By 2013 she had already raised three rounds of equity. Another round threatened her majority ownership. A first attempt at borrowing had disappointed her. When she reached Espresso Capital, Alkarim Jivraj admired the founder. The loan would have to wait.

Espresso introduced Peterson to a new chief financial officer. The work began with operating numbers, cash forecasting and pricing. Months later, HomeStars returned with a turnaround plan, and financing followed. A lender had found a useful way to say: come back when this will work. In a trade whose product is money, the introduction was an unusually revealing piece of inventory.

The episode gives Jivraj's career a practical starting point. Founder control has a price, whether the bill arrives as surrendered shares or scheduled repayments. Choosing a loan does not make that bill disappear. It changes the obligations. His work sits in the space between a founder's wish to remain in charge and a business's ability to support the arrangement.

“We were thoroughly impressed with Nancy.”

Alkarim Jivraj, on meeting HomeStars’ founder

A history degree, then the deal table

Jivraj studied history at the University of Toronto and earned an MBA in finance at Western's Richard Ivey School of Business. The combination makes a pleasing entry on a financier's résumé: one discipline studies what people did; the other asks what they can afford to do next. He completed the Toronto degree in 1991 and the Ivey MBA in 1996.

He began at Yorkton Securities in 1996. There he eventually led the technology investment banking practice and co-managed two investment funds. This was an education in capital from several directions: advising companies on transactions, assessing investments and participating in the machinery that connects businesses with money. Later, he would work through both venture capital and venture debt.

That early period also includes a regulatory settlement. In December 2001, the Ontario Securities Commission approved an agreement concerning his 1998 purchase of Games Trader shares while involved in its financing and proposed reverse takeover. The agreement characterized the purchase as contrary to the public interest because of his role and his knowledge of, or access to, undisclosed information. It provided for a reprimand, a $10,000 voluntary payment and $5,000 in investigation costs. Jivraj accepted the facts for that proceeding.

The episode belongs in the career alongside the subsequent appointments. It concerns the boundary between a banker's work and a banker's own investment. It also leaves a precise record of the conduct and the settlement, without requiring a speculative story about his private response. A career in finance is made of transactions; its record includes the conditions under which those transactions were made.

He had already sat on the equity side

In 2004, Jivraj founded Intrepid. His work included the Intrepid Business Acceleration Fund and the advisory business Intrepid Equity Finance. Before becoming known for lending, he had been involved in raising equity and helping companies develop. He arrived at venture debt having participated in the ownership negotiations founders were trying to manage.

At Streamlogics, he helped arrange institutional financing and a management buyout of a strategic investor, joined the board in 2006 and later advised on the 2009 sale to Thomson Reuters. He also led eSentire's Series A financing and served on its board. These were relationships that extended beyond a funding announcement to the subsequent work of building and selling a business.

He joined Espresso in 2013 as managing partner. In August 2015, co-founder Gary Yurkovich announced that an investor group led by Jivraj had acquired majority ownership of the funds' management company. Yurkovich continued as executive chairman. Jivraj became CEO in 2015. The change was a succession in an existing business, with an existing team and lending history.

Owning the management company put him on the operator's side as well. He now had a financing business to develop while assessing other people's businesses. The relationship between ownership and responsibility, already familiar from his advisory work, acquired a rather direct application. He was making decisions about capital for clients while making decisions about the firm supplying it.

Twenty-four months, one different calculation

Espresso began in 2009 with tax credit financing and shifted fully into venture lending in 2016. Software offered a particular problem to solve. A company could have customers paying regularly, promising economics and a substantial growth budget, yet little equipment or property a conventional lender could take as security. The value was in a continuing commercial relationship.

Jivraj's June 2020 writing on venture debt examined that mismatch. Young technology companies spend on sales, marketing and product development. Those expenses can make growing businesses look unprofitable in conventional accounts. Evaluating them requires attention to the business underneath the reported loss: customers, recurring revenue and the economics of acquiring more of it. Optimism still needs a calculation.

In July 2018, Espresso announced a SaaS lending program offering qualifying companies up to 24 times monthly recurring revenue, with loans up to $10 million. Those were program limits, not a cheque for every applicant. They made a specific argument about how a subscription business could be financed: revenue relationships deserved to feature in the lending calculation.

The numbers also explain the appeal of the HomeStars story. Peterson eventually used Espresso funding to build her team and sales operation. HomeAdvisor acquired HomeStars in 2017. She had maintained control through to the sale. The financing was one part of that outcome, alongside the operating improvements that made the loan possible. The loan followed the repair work, a less glamorous chapter than the sale.

A Canadian lender crosses the border

Jivraj's ambitions for Espresso soon required a wider map. The firm opened a Montreal office in December 2018. In February 2019, announcing the arrival of former BMO technology banker Mark Gilbert, he said Espresso had doubled its business the previous year and was expanding into the United States. Growth meant building origination and underwriting capacity as well as finding borrowers.

A $200 million KeyBank credit facility followed in November 2021, complementing existing facilities with BMO and Scotiabank. This was borrowing capacity for Espresso's lending activities. It was a different kind of transaction from a venture equity round, and a different number from the amount Jivraj himself had invested. At that point the firm said it had financed more than 300 companies across Canada, the United States and the United Kingdom.

By November 2023, Espresso's portfolio was three-quarters American, with the remainder divided evenly between Canada and the United Kingdom. Jivraj was still discussing Canada's financing market, particularly its strong bank participation, while running a business whose borrowers were largely elsewhere. Geography had become part of the operating model rather than merely a line beneath the company name.

The paperwork has a purpose

There is a less photogenic side to this expansion: getting the numbers after the money has gone out. A lending relationship continues through reports, changing forecasts and conversations about performance. The announcement photograph records the beginning. The subsequent spreadsheets carry considerably more of the plot. Unfortunately for magazine designers, spreadsheets seldom wear an interesting jacket.

Jivraj has put attention into this machinery. In 2021, he said Espresso had helped shape the vision for FlowPoint, software designed to automate the collection of business performance information. Separately, Espresso developed its own portfolio analytics and risk management platform, Espresso Insights. His 2023 writing on selecting credit managers emphasized data infrastructure and comparisons that account for risk.

That work makes sense of his public argument for specialized lending. Recognizing a promising company at the outset is only one task. Keeping track of what changes is another. Customer retention, costs and cash consumption can alter the position long before a financing milestone arrives. Better reporting gives a lender more chances to discuss those changes while choices remain.

His public conversations include an April 2020 Elevate session on founder financing with Michele Romanow and Kaz Nejatian, and a 2022 podcast with wealth manager Brian Ginsler. He also served on the Upside Foundation of Canada's board from 2017 to June 2023. The foundation connects company equity pledges with future charitable donations, another setting in which the eventual destination of ownership matters.

The clock on the balance sheet

In March 2026, Jivraj returned to software lending with an argument about valuation. A lower revenue multiple does not by itself describe the whole change in a company's value; revenue may have grown during the same period. And a decline in equity value does not automatically mean a lender has lost money. Loan size, valuation assumptions and the equity beneath the debt all affect the result.

In May he turned to durability. His emphasis was the ability to preserve cash as conditions change, including pressure from AI. A business must retain customers, adjust spending and respond soon enough to keep options open. These are his underwriting arguments, rather than promises that software lending is protected from disruption. They make the calendar an active participant in the balance sheet.

“Structure creates time. Durability determines how that time is used.”

Alkarim Jivraj / May 2026

The current writing gives his earlier dealings a useful continuity. At HomeStars, operating repairs came before the loan. At Espresso, expansion came with investment in staff, borrowing facilities and monitoring. Each arrangement needed something beyond enthusiasm for growth. A founder's confidence can persuade a room. It still has to survive the arrival of next month's expenses.

Jivraj has worked on several sides of that table: banker, venture investor, adviser, management-company owner and lender. The personal story visible through those roles is about the consequences of financing choices. Who remains in control? Which obligations arrive next? How much room is there to act? The questions are ordinary enough to fit on a small sheet of paper. Answering them can occupy a career.