AskMen founder Ricardo Poupada: Your small business won’t grow if you just stick to what you know

ricardo poupada

As part of a regular series powered by Dell, BetaKit asks prominent entrepreneurs to share how technology has evolved since they first launched their business, before predicting where it will take them.


Ricardo Poupada has a long history in digital media, having founded AskMen.com before stints at IGN, News Corp, and Ziff Davis. Now the co-founder and CEO of 5th Wall Agency, Poupada works to bring leading-edge AR and VR technology into global corporations. But Poupada faced an uphill battle when it came to leveraging technology to build his businesses.

What was the state of technology when you started your career?

When I first started my career in the mid-1990s, access to a computer was considered “bleeding edge” and fax machines were omnipresent. There wasn’t much else at the time in the way of technology; everything was done manually.

After a few years of working, and just before I started AskMen.com, I started my first venture to help companies make websites online.

The business wasn’t that successful, but I was able to stay miles ahead of competition because I used a personal digital assistant to help me organize my day. Just having automated reminders, electronic task tracking, and other little features helped to keep me informed and ready to act.

It was not until 1999 that I founded AskMen.com, and that’s when the real struggles started.

So what were the biggest struggles you faced getting AskMen off the ground?

One hurdle for AskMen.com that is still crucial today is access to robust real-time data.

When we were first starting, we had to wait for overnight log-files to compile to show us information about our site. For instance, we might have an AskMen article featured on AOL or MSN (two of the biggest websites in the world at the time), but we wouldn’t know where our surge of web traffic was coming from until the day after.

“I think the future of work is headed for more decentralization and working across multiple time zones.”

This hindered our ability to adapt, since real-time data is so crucial to making decisions. Things like analyzing user patterns, A/B testing article titles, and other things easily done today were simply not an option at the time.

Further, collaboration was, and remains, a big challenge. Back then, the ability to communicate beyond email was limited. There were some chat applications, but none were built for business use cases.

The biggest hurdle, though, was changing our mindset to welcome digital innovation.

We had software like spreadsheets on our desktop computers, but many still did data entry manually because that was what we were used to. Overcoming that mindset to embrace change was critical to our success.

Are there tools or support systems available now that you wish you’d had back then?

I wish, starting out, that we had enterprise communication apps that took away the heavy lifting from email and allowed uploading of files, real-time communication, and team chat rooms.

Productivity tools are also a big one. We had rudimentary tracking and reminder capabilities in the early days, but there are so many tools out there now that aid in collaboration and task tracking.

With that added collaboration ability, I wish we had robust CRM (customer relationship management) and marketing automation software, which would have allowed us to garner so much more information about our users and store it in an effective way.

These technologies all existed back when we started, but were so cost prohibitive that we just couldn’t use them.

Is there any advice you’d give to your past self?

My advice to my past self — and any entrepreneur today — is to make sure you understand all of the tools that are available and find out which are a good fit for you.

“Building empathetic relationships is crucial to success because your customers open up more, are more willing to take risks with you, and are more willing to stick around when things get rough.”

I challenge my former self, and current entrepreneurs, to break out of the habit of sticking to what you know instead of looking at what is out there.

For instance, we tested out multiple productivity tools before finding the one that was the right fit for our company and the way we work.

If you stick with a tool just because you spent a lot of money on it or it’s already installed, you risk losing your business because your foundation will not be right for your growth.

You need a different mentality. Especially today, technology is moving fast and you need to be willing to use whatever technology will make your life easier, especially as a small business just starting out or looking to grow.

What do you think is the next big trend in technology and how will it impact the way we work?

I’m a bit biased given my work, but I believe that VR has the potential to fundamentally change how we work in the business-to-business arena because it can help build empathy across borders and time zones, which is increasingly how the world of business is moving.

VR can show you what remote working conditions are like, help you understand new customer training, or other things that enable companies to generate empathy with their employees and their customers.

For small businesses looking to stand out in the pack, building empathetic relationships is crucial to success because your customers open up more, are more willing to take risks with you, and are more willing to stick around when things get rough.

Where do you think the future of work is headed?

I think the future of work is headed for more decentralization and working across multiple time zones.

You can prepare for this change through building up processes and systems — both of which are aided by knowing all the tools out there — and by solidifying corporate culture.

Once you do this, you begin to change another mentality – the belief that work requires a physical office all the time.

Just as I needed to change my mindset to be open to digital innovations when I first started, entrepreneurs today need to be open to the idea that working in an office all the time may not be the best fit for your organization or your clients.

Poupada knows entrepreneurs must understand the tools available to find the ones that best fit their business. Dell has the right tech to fit your work, for today and tomorrow.

Stefan Palios

Stefan Palios

Stefan is a Toronto-based entrepreneur and writer passionate about the people behind tech. He's interviewed over 100 entrepreneurs on topics like management, scaling, diversity and inclusion, and sharing their personal stories. Follow him on Twitter @stefanpalios or send an email to stefan.palios@gmail.com.

  • Good article. Re selecting tools, I agree it’s good to rethink sometimes. I used Google Analytics for my website (https://intently.co) for years and never thought there was a better option until I was getting really frustrated with some of its features. I checked around 10 of its competitors, and have now switched to Heap Analytics – it’s a much better “business intelligence” type of solution to allow you to explore data and trends.