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An Interview with AskMen.coms Founders
The year is 1999 — Y2K is on the horizon, “The Sopranos” is airing its first season on HBO, David Beckham and Victoria “Posh Spice” Adams are tying the knot and Pokemon is all the rage. Most importantly, AskMen is on the precipice of becoming a beacon for men of all ages and backgrounds to ask questions without judgment, seek advice on everything from relationships to job interview etiquette and become a part of a community devoted to self-improvement and betterment.
RELATED: AskMen Through the Years
While a lot has changed over the past 20 years, AskMen’s mission has remained the same. To celebrate this major milestone, we checked in with our founders, Ricardo Poupada and Christopher Rovny, to get the real story on how AskMen came to be, what inspired them to start this site and how their lives and how the idea of ‘being a better man’ has evolved over the last two decades.
What made you want to start AskMen?
Chris: It all started at a coffee shop on McGill College street in Montreal. We were supposed to be studying but started brainstorming on business ideas instead. Our initial idea was to start a real estate company (the kind of holding company that buys skyscrapers on Madison avenue). The reality was that we just did not have any equity or connections to make that happen.
That’s when a man in a nice suit walked into the coffee shop. When he sat down, we noticed that he was wearing white socks – a big fashion faux-pas at the time – unless maybe you’re Jay-Z, of course. At that moment the conversation shifted: guys need fashion advice, and they probably need advice on other aspects of their lives too. Simple tips to help them with their look, finances, health, dating situation, etc.
We were avid fans of GQ and Maxim and thought we would focus on helping guys, but through an online property for men instead. That’s how it all started.
Ricardo: Chris sums up the ‘light bulb’ moment very well. A guy walks into a coffee shop wearing expensive suit and shoes, but he sits down we noticed the white socks, a complete fashion fail, and the inspiration for creating a site that told men the little things that distinguish the guys who seem to have that extra 1 percent vs the rest.
Funny enough, this story has been told so many times over the years with this gentleman being the butt of jokes at many conferences, interviews, client meetings, etc, with never a thought as to why he had white socks. Yet, a few years ago, when I was doing physiotherapy for a knee injury, I had a very early morning appointment, so I rushed out of the house. I had taken my jean, blazers, shoes, etc. and dressed in gym gear for physio. At end of session… I realized I had forgotten my dress socks, so I ended up all day in blazer, pants and white socks. So maybe that’s what happened to that guy that day.
How did you come to decide on the name?
Chris: We needed a strong name with the word MEN inside and for SEO reasons, we needed our name to start with an A. At that time, directories (like DMOZ.org) worked in alphabetical order and they had a lot of weight on search algorithms.
Ricardo: I’ll add, that the name came in a completely unromantic, unscientific way. Just like Chris described, the key was for the name to start with ‘A’ so we would be listed in places like Yahoo at the top of their directories (people used to go through link directories seemingly as much as doing searches). So at Chris’ apartment, while we had a little BBQ on, we had a dictionary on his balcony and would pick out a word and add ‘men’ and see if the domain name existed.
We liked ‘AboutMen.com’ until we saw it was taken and we just went down the list until the simplicity of ‘Ask’ and ‘Men’ came together. We also liked the fact that it was short and relatively difficult to misspell, though people have sometimes taken liberties with the name like you can imagine.
What did you see AskMen becoming?
Chris: Frankly, at first we had ambitions of growing traffic and generating revenues from advertising and affiliates. Even after a few months of operating the business, my mom still kept referring to AskMen as a school project.
(Thank you, Mommy, for believing in us and allowing us to use your balcony for brainstorm sessions.)
But as time went on and our stats kept growing, we were looking at becoming the largest online destination for men 18 to 34, something we achieved in a little over 5 years.
Ricardo: Quickly we realized that we were creating a library of content that could be a resource. It was sort of a precursor of Wiki in the sense that we wanted to create an encyclopedic database of articles covering every subject men might be interested in, an impossible task given the size of our team and writers, but that was the goal.
What was your first article was about?
Chris: My first article was on wearing white socks, the Dos and the Don’ts. Thank you to that gentleman in the coffee shop – you really changed my life and hopefully that of many others.
How did it feel to know you were inspiring and motivating millions of men across the world?
Chris: It’s still crazy to think about how a publication from Montreal affected so many guys around the globe. We received thousands of emails from guys asking us questions and thanking us for our content. It was unreal.
I’ll reflect on it every now and then and I’m extremely proud and grateful for what we accomplished as a team. Everyone contributed. [I thank my editorial team, at the time,] for sprucing up my articles, and my two partners for pushing me to surpass myself and help me forge who I am today.
Ricardo: It’s funny, just recently I saw a YouTube interview with Shawn Mendes where he was asked a similar question, and he said that even though he had 700,000 or a million views or something in the early days, on Vine or YouTube, it was when he showed up at a meet and greet with 300 fans that he realized ‘wow, people are paying attention.’
Over the years, we received plenty of validation, mostly through voluntary testimonials of our readers who would tell us ‘I grew up with AskMen, I went through college with you, asking my current girlfriend out thanks to you, aced my first interview because of you, became a great father through you.’ Mothers, divorcees, widows, teens, people with severe depression, or in abusive relationships, or in terrible jobs, it was staggering the amount of feedback we had, it was a tradition to forward all these types of emails to the entire staff as a reminder of the impact we were having.
I was at a wedding a few weeks ago, and I had a gentleman, about 10 years younger than me say: ‘Thank you for AskMen, you will never know how much it helped my life.’ How could that not mark you?
Were there any big hurdles to overcome at the start?
Chris: From day one we overcame hurdles. There are too many to list. I believe the number one hurdle from a business standpoint is that we were based in Montreal. Our key market was the U.S. and everything media-related was happening in New York and L.A. We traveled there regularly but it’s not the same thing as being there day and night. On the flip side, the fact that we were in Montreal also allowed us to keep costs extremely low and, more importantly, keep our focus laser-sharp.
Ricardo: As Chris mentioned, hurdles were endless.
We had to build a brand, from scratch, so every meeting, every interaction, every touchpoint was a chance to advocate and explain the brand. That was probably the biggest challenge, because even though we had a very large audience, we hadn’t passed into the collective cultural conversation as a de-facto must-read when it came to men’s lifestyle content as GQ or Esquire had established over the years.
Thinking back now, it was crazy that three young guys in their early 20s decided to take on the established men’s media world from a small office in Montreal.
What was your most memorable experience in the early AskMen days?
Chris: It’s hard to pick just one as we had so many memorable experiences – good and bad. Our first advertising/business development call came from Howard Stern’s team, and I picked it up. It was a little nerve-racking but the funniest part of the story is that they kept referring to us as ASSMEN.com instead of ASKMEN.com and it took a few times to just clear up that part of the conversation.
Did you have any icons from TV or movies that inspired you when creating AskMen – in terms of style, behavior, etc.?
Ricardo: There was a long list of guys that served as inspiration when we searching for our ‘voice’ in those early days.
If I think back to the names we probably mentioned most often were George Clooney, Hugh Hefner, David Beckham, Bourdain, Steve McQueen, Stallone (who had a short-lived men’s magazine as well), Steve Jobs, DeNiro, Al Pacino and even a skier called Alberto Tomba!
Later years were defined by guys like Agnelli (Fiat Founder), his grandson Lapo Elkann, Apple designer Jonathan Ive, Don Draper, Jay-Z, Mark Ronson, Daniel Craig and I’m biased but also guys like Jose Mourinho and Cristiano Ronaldo for the aesthetic they brought to football (I hate saying soccer).
Each brought a unique element to what it was to be ‘a better man,’ at least in what they were focused on.
How do you think the idea of AskMen’s slogan: ‘Become a Better Man’ has changed over the last 20 years?
Ricardo: When we started... It was a rather vain concept, that myself and probably countless others succumbed to at the time, but luckily along the way, the idea of becoming a ‘better man’ has evolved to much more than just that original idea of image-based self-improvement. Today ‘become a better man’ symbolizes becoming the best possible version of yourself, whether it’s as a friend, husband, father, co-worker, teammate, whatever. It’s a much more real and authentic ideal, and a wonderful legacy of AskMen.
Do you think the idea of masculinity, in general, has changed since ‘99?
Chris: The idea of masculinity has definitely evolved over the years. I believe there are a lot more versions or perceptions of what masculinity is today. I think masculinity is less stereotypical today. It has evolved like everything else and generally, there is more openness to the different versions… at least where I live and within in my entourage. You just need to think of the evolution of James Bond 007 from the '70s to today.
Ricardo: I think Chris nails it, and the James Bond analogy is especially apropos.
I have no doubt the concept of what constitutes a great man, or a man fulfilling his potential today is different from what it was 20 years ago. I’m not saying that 20 years ago masculinity was as one-dimensional as the stereotypical post-war working stiff, but today there isn’t a conversation I have with male friends that doesn’t cover the ‘all-round’ needs of what it is to be a man today.
You need to check many more boxes to fit into the masculinity box and not in the chauvinist one. Changing diapers, showing emotion, being a mentor, fulfilling your partner emotionally, they are not new concepts but certainly examples of attributes that are now accepted as necessary in defining what a great man is. I’m also glad the movement of bringing back the ‘gentleman’ is in full force, respect for others, discretion in words, manners, even the aesthetics of ‘gentlemen’ is a welcome relief from the overly casual movement of just a few years ago.
What are you up to these days?
Chris: I am a proud family man and father of two beautiful and clever little girls. On a professional level, I am a serial entrepreneur.
My main focus is on a new-age media company called OBOX. I am also an investor/advisor in a few real estate projects, a food distribution business (Monpetitmarche.ca), a CBD/online marketplace related business (Tillitcorp.com), and a protein-based brand called Maillard (Maillard.co).
Ricardo: Right now, I’m changing diapers, I had a new addition just a few days ago.
But seriously, I’m actually on a sabbatical, and loving it. I can’t explain how time seems to be flying even without the 60-hour work weeks. I’m practicing what we preached at AskMen for years, that life has so many more components than your 9-to-5 gig.
I had started a VR/AR company called 5th Wall a few years ago that had incredible early success and spectacular growth, but it wasn’t a business model I loved, so I stepped away. It’s a cliche but you have to love what you do. I’m still a very active angel investor, I tried to pay it forward with younger entrepreneurs in the same way we were supported when we were starting. Some would say too much, at my peak. I’m scaling that back now to a much more manageable number.
Has becoming a father changed the way you think of what it means to be a great man?
Chris: I am not sure being a good father makes you a great man, but it makes you a good man. All I can say is that having kids has given me a meaning to life. Call me cheesy but it’s true. There is absolutely no amount of money that can beat the feeling of having your kids jumping in your arms when coming back from work and having a genuine: ‘’I love you daddy’’… it makes everything else around you secondary.
Ricardo: Agree with Chris. I think if you have kids, and you are able to be their hero because you set the bar high on what fatherhood is, then you become a great man, at the very least for the people that are most important to you.
There is no doubt, if we all had kids when we started AskMen (our average age was 23 of the whole staff in our first year), we would have gone in a very different direction, with a very different approach to content, brand positioning and even work ethic.
But there are many men I know that I consider great because they are great fathers, so yes my perspective has changed.
Great taste is something you’ll always have. Are there any products/brands that you think are changing the game for men?
Chris: I am just amazed at how quickly brands, concepts, and products are popping up in just about every category. It’s hard to keep track. But companies like Amazon, Google, Apple, Facebook, etc. allow us to discover those cool brands and trends. Those are the companies I think are changing the game for all of us.
Ricardo: Brands like Adidas, Tesla, Apple, even Dyson have fanatical followings. Talk to a Tesla owner and you get the epitome of ‘drinking the Kool-Aid,’ they are forcing everyone to up their game and even if they don’t ultimately become the biggest automaker they will certainly be seen in the history books as the catalyst for an industry-wide revolution.
Other brands that I admire that nail their ‘why’ are companies like Asana, Dollar Shave Club, Frank & Oak, or especially Rapha, who seemingly single-handedly revived the cyclist fashion industry. Even old-timers like Aperol is showing you can regain relevancy, it seems like an Aperol Spritz is the drink of summer for the last few years not only in Europe but here as well. That’s a credit to understanding a new way to target and market to men (and women).
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