Tuesday, July 22, 2025
Today on Bookpleasures.com, I am delighted to welcome Terry Kirk, a dynamic force in both the literary and finance worlds.
Based in downtown Toronto, Terry brings a multifaceted background to her craft—holding degrees in journalism, English literature, and a Juris Doctor (Law), along with a master's focused on digital transformation.
Widely recognized for her innovation in the finance and fintech sector, Terry's broad professional journey includes founding and leading the Funding Portal, a groundbreaking fintech platform dedicated to helping companies secure crucial funding.
After more than a decade practicing law and eventually guiding her company through a successful acquisition by a global firm, Terry turned her keen analytical mind and storytelling talent toward fiction.
Her novel, Pitfall is a gripping explorations at the intersection of financial intrigue and historical events.
Join us as we dive into Terry's inspirations, experiences, and the creative process behind her work—uncovering what it takes to turn real-world high stakes into riveting fiction.
Good day Terry and thanks for taking part in our interview.
Norm: How did your own background as a legal professional and fintech founder shape the way you portrayed high-stakes finance and legal intrigue in Pitfall?
Did your experience in fintech lead you to include any specific technologies or financial instruments in the story that readers might find intriguing?
Terry: Although you won't require any background in law or finance to enjoy my stories, my years of experience in these sectors inspired me to write these stories, which are designed to make complex financial stories entertaining and accessible.
My literary hero is Michael Lewis, author of The Big Short, Moneyball, and other books that demystify financial events.
Think Margot Robbie soaking in her bubble bath, explaining why markets collapse. As a lawyer, I learned to weave gritty facts into winning cases.
Above all, I love to communicate. I once delivered an 18-minute TEDx Talk under a bright spotlight with no notes.
Norm: What drew you to set Frank Cork's story against the backdrop of the 1929 market crash, and what parallels do you see with financial crises today? Can you share any personal or historical anecdotes that particularly influenced your depiction of the 1929 market crash?
Terry: The 1929 Crash was the most disruptive economic change in world history. Could the market crash again in a similar way? The answer is unabashedly yes.
True, there are more protections and oversights in place. However, we are living at a time when some are hellbent on tearing them down.
And there are exceptional levels of volatility and uncertainty not just in our stock markets, but also in housing and day-to-day financial decisions, including what groceries to buy.
My understanding of the Crash, at a visceral level, beyond the research, is informed by the stories my mother told of her people, who lived on the Canadian Prairies during that era.
Hunger and drought were the defining elements of their lives, yet they went on to raise strong families and live productive lives.
Norm: Frank faces complete financial ruin in a matter of hours. What kind of research did you undertake to authentically capture the raw emotion and chaos of "Black Tuesday?"
Were there any surprising or unexpected findings during your research that changed how you wrote key scenes?
Terry: I used a two-pronged approach through texts and novels, ranging from John Kenneth Galbraith's seminal treatises on the '29 Crash to Steinbeck's Of Mice and Men.
That was the easy, fun part. The second approach was micro-level fact-checking, including how people swore and what they wore. Did my research reveal surprises? You bet! I was struck by how constrained women's lives were, and this sweetness in the expressions of the day. You can hardly imagine a hard-bitten trader like Frank exclaiming "Bee's knees!" today.
Norm: Frank's journey from success to downfall and exile is dramatic. What psychological qualities were most important to you when constructing Frank's character?
How did you ensure that Frank's psychological struggles felt authentic and relatable to readers?
Terry: Frank was not a very imaginative person before his adventure. As a trader, events are binary: winners and losers, buy or sell, markets trending up or down.
He likes ledgers, lining up arguments on one side of the line or the other. But when his life changes, the clear choices no longer exist. One of the core themes in Pitfall is the positive role that imagination plays in managing through crises.
Success requires accepting that the life you've built no longer exists and that you need to reimagine it in some other way. It is a journey that many experience, as immigrants, or through the loss of a loved one, or divorce.
As a lawyer, one's role is to help people and organizations navigate through these changes and worse. As a writer, I draw on these experiences to make my characters' crises and responses authentic and real.
I hope this emphasis on the power of imagination will inspire readers facing their own challenges.
Norm: The Canadian Prairies and Chicago both play central roles in Frank's story. How did you approach rendering these unique settings, and what do they symbolize in Frank's journey?
What role do the contrasting settings play in highlighting Frank's internal conflicts and transformation?
Terry: The 1929 Crash stands out among the great market upheavals because the highs and lows on either side of it were exceptionally so.
In short, it was a period of drastic contrasts—from the soaring heights of the 1920s to the desperate lows of the 30s, transformed from one to the other in a matter of days and hours.
Befitting that era, my story is one of like-minded contrasts, as Frank and Katrina's lives gyrate from rich to poor, and urban to rural—from America's second-largest city to the wide-open expanse of the Canadian Prairies.
And that's just the physical! Frank's mental state also changes—from the hyper-cocky trader to someone struggling to redeem himself.
Norm: The subplot involving Canadian whiskey smuggling and the Chicago mob introduces a criminal element. How did you weave together real historical figures or events with your fictional characters?
How did you balance historical accuracy with creative license when incorporating the mob and smuggling elements?
Terry: Historical fiction is my favorite genre for the very reasons you cite. You build this robust foundation of facts, then layer on creativity, like a light-hearted breeze blowing across the top.
My storytelling engages both the left and right brain; in technological terms, it combines the rigors of Excel with the wide open white spaces of Microsoft Word.
The rampant underground market for alcohol during the Prohibition era provides just such an opportunity. The fictional Frank is inserted into the real-life world of Al Capone and Bugs Moran.
Norm: Can you discuss the challenges and rewards of blending fast-paced plotting with detailed historical research? What strategies did you use to keep the pacing tight without sacrificing historical detail?
Terry: I love the pacing challenge. It's there in almost every word. I'm a bit of a speedster myself, and as a lawyer, you bill by the hour—or the minute, it seems—so you are constantly moving things along.
But you have to avoid old tropes like "Suddenly . . . ." I avoid it like the plague. You have to find more sophisticated ways of communicating that events are unfolding quickly.
You're right that detail can be a counterpoint to pace, but that is what makes for good literature—internal tensions, push and pull, and the yin and yang of it all.
Norm: In writing a multi-generational saga, did you have the overarching Cork family arc planned from the beginning, or did it evolve as you wrote?
As the saga progresses, how do you plan to develop the themes of legacy and generational change?
Terry: Yes, I did plan the narrative arc of the three books from the outset, with the goal of bringing the cataclysmic financial events of the last century alive for a new generation through fast-paced and entertaining stories.
As time passes from one event to the next—from the Crash of '29 to the outbreak of World War II in '39, and the space race in '57—the Cork family evolves.
By Book 3, Katrina and Frank are minor characters, and their daughter, Franny, emerges as the protagonist. The firm moves from Chicago to New York, and Hector Ray, the Black trader we meet in Book 1, also emerges as a leading character.
But Frank and Katrina's legacies—including old lovers and new financial pressures—are never far behind.
Norm: What moral or thematic questions did you most want readers to wrestle with through Frank's descent and quest for redemption?
Are there any particular scenes or moments in Frank's journey that you hope will provoke deep reflection in readers?
Terry: Frank's journey is both literal—as he flees his home and family—and metaphorical. Who is he as a man when stripped of everything he thought was important?
It is immediately clear that a return to his old role and way of life is out of the question with the market torn asunder. Frank's journey prompts us to consider how we would behave in the face of such cataclysmic losses, whether it be the loss of a job or a spouse.
What would we do if we were Frank or Katrina? Did they make moral and ethical choices? Would we?
Scenes that are particularly pivotal for Frank include his arrival at the Canada-US border, literally the line between his old life and the new, and again, when desperate for money, the only opportunity in sight requires skirting the law.
Norm: Family plays a pivotal role—how did you seek to reflect the impact of financial disaster on personal relationships, especially between Frank and Katrina?
How do you think financial hardship reshapes family dynamics, based on Frank and Katrina's relationship?
Terry: In my experience from practicing law and more broadly, finances play a pivotal role in personal relationships, especially when there is a disruptive change.
What happens when the sole breadwinner loses it all? It is a colossal challenge to navigate at every level—from practical issues like "How will we survive?" to volatile feelings, including shame and betrayal. Frank and Katrina experience it all.
Norm: Where can our readers find out more about you and Pitfall?
Terry: To learn more about my author journey and my debut novel, Pitfall, visit any of these:
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My author WEBSITE
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Social Media
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Purchasing platforms
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Amazon.com: Amazon.com_PitfallbyTerryKirk
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Amazon.ca: Amazon.ca_PitfallbyTerryKirk
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Indigo: Indigo_PitfallbyTerryKirk
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Other great Links:
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Watch the television interview: LIVE TV I TERRY KIRK ON CP24
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Listen to the Podcast: PODCAST I LIVING THE NEXT CHAPTER I PITFALL BY TERRY KIRK
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Goodreads: Goodreads_PitfallbyTerryKirk
Norm: As we wrap up our interview, Pitfall is the start of a trilogy, what can readers look forward to as the Cork family navigates World War II in your next novels, Plunder and the Space Race in Probe?
Without giving too much away, can you hint at some of the major challenges the Cork family will face in the upcoming books?
Terry: Book 1, Pitfall starts in 1929 as the Cork family navigates the 1929 Market crash.
In Book 2, Plunder, ten years have passed. World War II has erupted in Europe, and Frank is charged with raising a war chest—$7 trillion in today's dollars—to fund America's possible entry into the rapidly escalating war. Frank and his family relocate to London, the nexus action.
Will America enter the war? How will the family fare? I'm expecting Plunder to be out next spring. Book 3, Probe, moves forward to 1957 when the Russians shock the world by launching a telecom satellite that triggers the space race.
Frank's daughter, Franny, has succeeded her father at the helm of the firm and works with her client, a struggling defense contractor, to finance and launch the US response.
Norm: Thanks once again and good luck with all of your future endeavors
Norm Goldman of Bookpleasures.com