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The Life of a Private Investigator

April 23rd, 2017 | by Richard Paul
The Life of a Private Investigator

As a young, hungry, entrepreneur, Ashley Cyr sought out her dream—and obtained it. This strong, dedicated and extremely hard-working woman is well on her way to great success. From a young age Cyr was very observant, perceptive and analytical.  She was born in the surroundings of Ottawa, ON and moved around the Ottawa-area many times throughout her youth. As a child, Cyr was raised in the intelligence world. Discontentment working for the federal government, a passion for investigation and growing up in a very analytical environment, Cyr was destined to open up her own private investigation agency.


Ashley 1 (2)

Coming of Age

Cyr worked a number of professions over the years before she opened up her own P.I. agency. Once out of high school, Cyr strongly considered joining the military as an infantry soldier. She hoped to attend the Royal Canadian Military College in Kingston, but life took her down a different path. In her early 20s Cyr worked as a prison guard at a detention center in The North West Territories. Over the course of the eight months that she worked as a guard, she learned an abundance about the prisoner’s mind and mental illness.  Cyr eventually found herself back in Ottawa and working in the federal government. She was extremely skilled at her job, but she just couldn’t take the monotony of working for the government anymore.

In 2015, Cyr quit her job, obtained her private investigation license and opened her own agency. She says, “It was an uphill battle” when she first became a private investigator. She knew it would be nearly impossible to get a full-time job in the Ottawa area, so decided to start her own agency instead. Now, just over a year and a half later, not only does Cyr have one of the most successful P.I. agencies in the Capital, but she was also nominated as a finalist for the 2016 Women’s Business of the Year Award in the Emerging Entrepreneur Category. She has taken several additional courses to give her agency the upper hand, including tactical surveillance, interviewing and interrogation training. Cyr now teaches those same courses, including private investigation, loss prevention and security guard courses as well.

The Life of PI

As Ashley Cyr described, “I’m definitely not James Bond”. When most people picture a P.I.  they probably envision an older man wearing a trench coat, holding a spiked—coffee and smoking a dimly lit cigarette. But, it’s not as glamorous as it looks in the movies; being a P.I. is a very grueling career.  Cyr says she regularly spends 12 hours or more in a car during surveillance stakeouts. Undercover work is not for the weak minded; it requires a great amount of patience and mental endurance.

Cyr deals with tear-jerking cases all of the time, but she says, “You can’t go into a case with any emotion”. As difficult as that may be, she has to remain impartial to the case at all times. Being a private investigator can drain you of all your emotional, mental stamina and energy. Cyr said that sometimes at the end of her workday she feels as if she had ran a double-marathon. Unfortunately, being undercover also goes hand-in-hand with a poor diet, lack of sleep and high stress levels. All of this combined can really take a toll on the body and the mind. Cyr says that sometimes she just needs to unplug from the world. It’s a difficult career, but for those who love it—it’s everything.

Even though Cyr mostly deals with corporate, private and legal cases, she still gets the odd request from the woodworks. Cyr has found that people are extremely distrusting of technology today, almost to the point of where they are afraid of it. Cyr says there is a collective paranoia forming in regard to technology in today’s world. In a world where everyone has a cellphone, computer, tablet or smart TV, it’s not hard to believe that people are skeptical of the capabilities of today’s technology.

The Reward

Cyr says it’s all worth it when she sees the look on a client’s face. Each case brings a different form of reward, whether it’s a corporate, legal or a private matter. Private Eye Investigations takes all of their cases very seriously, specifically missing persons reports. They do everything they possibly can to help those in need find their loves ones. Bringing people back together is one of the greatest feelings says Cyr. In some cases all the family and friends want is closure. Cyr makes a point to take on cases that no one else would. If there’s a will, there’s a way and Cyr will find it. She was recently working on a case that involved overnight rural surveillance in -30 degree weather. Not many investigators would go to those lengths to serve their client.

The Daily Struggle

As a young, female, private investigator, Cyr deals with misogyny on a daily basis. She said people are often thrown off by the fact that she is the owner of the P.I. agency. Most people expect an older man to own the agency, not a young woman. This is unfortunate, but not difficult to believe considering majority of her competitors are male. But, all of that changes as soon as they meet Cyr. Once they see how professional, articulate and knowledgeable she is, all preconceived notions go out the window. But, this can also work to her advantage, not many people would expect a young woman to be a private investigator. This makes it much easier for her to blend in to everyday situations, giving her the upper hand when collecting information.

The Network

Private Eye Investigations is not just a one woman show; it is a network of people that work together in unison. The Private Eye Investigations agency is made up of a carefully chosen staff of young and dynamic investigators. “We’re like a family”, says Cyr. Cyr and her team carefully utilize outside resources for gathering pertinent information. Knowing where and how to get direct information is key to success in the private investigation world. Cyr and her team often work with the Police and other P.I. agencies across Ontario to better serve their clients. Cyr has instilled her own moral beliefs in each of her investigators, and it shows. She believes that in order to move forward and be successful, everyone must be of the same mind set. “I am undeniably grateful for my staff; they are such a big reason as to why my agency is as successful as it is.”

Connecting the Community

Ashley Cyr and the Private Eye Investigations team strive hard to be part of the community. They are eager to connect with the people that make up our great city. Over the last year, Cyr and her team have participated in fundraisers for Operation Come Home and Veteran’s Canada. The P.I. team have also volunteered their time to work with young adults who have Asperger’s Syndrome earlier this year. These are just a few of the many ways Cyr and her team are reaching out to the community. “We’re licensed to operate across all of Ontario, but Ottawa is our home”, says Cyr.

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