
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.