By Peter Berton

Toronto premium escort Madison Winter (www.madisonwinterto.com) is renowned for her beauty, brains, and business sense. 

She is a success story (my words, not hers) who is willing to share her story and personal experiences with the Naked Truth’s blog.

Peter Berton: How did you get in escorting, and why?

Madison Winter: As many people know, before escorting I worked full time in corporate asset management. At the time, while I loved aspects of what I did such as creating relationships, networking, and sales, I didn’t love other aspects; like the long hours, fluorescent lights/cubicle environment, and everyone’s favourite — office politics.
It didn’t even occur to me that escorting, or the world of companionship, even existed until stumbling across movies and TV programs including Sugar Babies and Secret Diary of a Call Girl.
I’ve always lived alone and, for the most part, enjoyed the single girl lifestyle. While most of the media portrayals of escorts are sad and relatively dark, that wasn’t how I perceived it. Watching these shows all I saw was financial freedom, independence, and sexy adventures.
As it turns out, I was correct.
Almost immediately upon dabbling in the industry, I quit my job, built a professional website, hired a stellar accountant, and never looked back. 

Peter Berton: What your first escort experience was like?

Madison Winter: I still know and keep in contact with my very first client! He is a soft-spoken, quite good looking (in my opinion), mid-forties gent with an Australian accent. The physical and emotional attraction was mutual, and it didn’t feel like “work” in any sense.
This particular client was familiar with seeing escorts — he was always conscious of the time, my boundaries, and made an effort to be considerate and respectful. We both immediately clicked and spent numerous wonderful dates together.
I’m extremely lucky in the sense that he set a standard. I had no idea men could be so lovely.

Peter Berton: How has your career evolved over time?

Madison Winter: Evolve it has! In numerous ways, I’ve had to adapt to the varying supply/demand of my time. I’ve learned of peak and not-so-peak calendar periods, and make an attempt to structure time off around that.
Additionally, altering my rate structure and fees relatively regularly has helped me to mitigate demand and balance it with my own personal burnout.
When I began my career, I met with most clientele for short durations; an hour here, an hour there. Often at times, I saw numerous clients a day.
As I get older, I’m learning that I can’t accept every request, and have to structurally organize downtime in my calendar. Now, I strategically promote dates of longer durations and focus on the quality of our interaction, rather than the quantity of clientele. 

Peter Berton: What you have learned about marketing/protecting yourself in the escort industry?

Madison Winter: I take a relatively unusual approach to marketing in the sense that I’m completely transparent online.
I utilize social media almost to an extreme and post almost everything that occurs in my daily life, on numerous platforms. I’m always conscious not to reveal details that would put my safety at risk, but still maintain a relatively open-book marketing policy.
It’s time-consuming, but it’s free, and I believe brings in a more suitable  client for me.
When I first began my career, I truly believed that respect from my peers and clients would come if I appeared to be a “luxury” provider. The jury’s still out on what that means, but essentially, I’d organize photoshoots wearing beautiful dresses, designer shoes, and try to appear more ethereal and feminine.
Over time, and after many mismatched dates where I couldn’t meet the expectations I’d set about myself, I learned to market myself more truthfully.
Now, I refer to myself as the “girl next door.” I’m into rock music. I’m into ripped jeans. I’m probably going to curse.
I became unapologetic and honest about the kind of girl you’d be meeting, and it worked.

Peter Berton: What are your thoughts on current client attitudes and trends; including the impact of cybersex on client behaviours?

Madison Winter: You know, I have mixed feelings about this one.
On one hand, I see trends towards longer engagements, more social interaction and relationship-based dates, and on the other, I see a rise in porn’s influence in PSE style requests, particularly from the younger clientele.
Over the course of my career, and my friends’ careers, we’ve seen a shift from single hour bookings to multi-day bookings where we truly connect with our date and establish this long term relationship. I can’t help but wonder if that’s due to our branding and the growth that’s occurred within it over the years — or because client attitudes are shifting.
Simultaneously, sexual content is everywhere. It’s in our media, and for free on just about any platform imaginable.
I find that some clients — in my experience the men under 35 — seem to visit with a preconceived screenplay for specifically how the date’s going to go down. They’ll arrive with a checklist, and it’s more about the sexual act and agenda than the entirety of the experience.
I don’t believe one is good and the other is inherently bad, or vice-versa;  but it seems to come at both extremes. I suppose as a provider, it’s our job to either become a chameleon and cater to both, or choose whichever niche you enjoy most.

Peter Berton: What are your words of wisdom for other SPs (especially newbies),  and your plans for the future?

Madison Winter: This is going to sound cliche, and super bumper-stickeresque, but please — BE YOURSELF.
That is the single most valuable piece of advice I could give any fellow provider. It’s the thing that revamped and revitalized my business.
Too often, we compare ourselves with others; especially given the rise of marketing and interaction on social media. However, it’s easy to forget that we all have different strengths, weaknesses, things that we enjoy and don’t enjoy.
There is no ‘right’ way to escort. The industry is vast and complex. So market yourself AS yourself (to the extent of your comfort, of course) and choose a clientele and business plan that suits your personality.
It’s the easiest way, I’ve found, to enjoy your work more and reduce emotional burnout. 

About the Author

Winner of the NakedTruth.ca award for Favourite Adult Journalist, Peter Berton has written for Adult Video News, Klixxx, XBIZ, Xtra, and YNOT.com. He likes to interview sex workers to tap into their vast knowledge about human nature, business marketing, work/life balance and succeeding as entrepreneurs.