Selling 50 Million Calendars

Selling 50 Million Calendars

WOW. 2014 has been a crazy year with so much change and it’s only half over!  I am typing this from Canada, in a cool live/work space!  Personal life mostly aside, I’ve completely left the corporate world to hang out with a start up and build Gay Ambitions.  This change all happened because of what I started two years ago.

It began as a passion project because I felt unfulfilled sitting in a cubicle for 40 hours a week.  While I appreciated the job that offered me a chance to start my career in the middle of the worst recession since the great depression, I felt under-utilized, like the company could never quite figure out how to make the most of me.

Furthermore, I had a passion for the LGBT community and learning from inspiring leaders, which probably couldn’t ever be fulfilled in such a structured corporate environment.  Drawing from inspiration of others who were doing cool things, this project was born.  The podcast launched eight months later and I’ve now interviewed over 50 people altogether.

The fifth guest on the podcast was Bradley Roulston, an exciting entrepreneur from Canada who I met on LinkedIn.  I was really impressed by what he was doing with his start up, Timely.  The vision of Timely is bold.  The team wants to strengthen communities through their state of the art calendar technology, transforming the calendar into a promotional and distributional platform.  With Bradley and I both being members of the LGBT community, we shared a personal vision for using this technology to help strengthen our community in particular.

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Over the next several months following the interview, I connected Bradley to people who might be able to help make this happen.  We had a call with Here Media, the company that owns The Advocate, OUT,, HIV Plus, She Wired, and more. We met with StartOut and Gay Cities.  I talked Timely up to influencers and those I met at conferences such as Community Marketing, StartOut, NGLCC, SalonLGBTQ, and IGLTA.  We even had a call with a potential investor who wanted to fund this project to success.

At the time however, the timing wasn’t right to do this and the product wasn’t quite ready.  Bradley and I kept in touch almost every single week though, and I knew there was a synergy between us that would be unstoppable when the opportunity presented itself.

That opportunity came on Memorial Day. I was hanging out in the beautiful Los Angeles, considering relocating to the city and scoping out neighborhoods. <<There were many reasons I was considering moving there and for once the strongest reason was following my heart, not my head – but perhaps that’s for another post :)>>. I chatted with Bradley that Monday morning on Skype from my West Hollywood hotel room.  He said that the company had just completed a round of funding and that if I were still interested in coming on board – now would be a good time.

After a wonderful day driving around LA and Malibu with my best friend in a black convertible Mustang, I was really nervous getting ready for an important dinner.  Right before I left to pick up my date, Bradley called and said, “This is happening!”

After dinner, which was promising but not all that I had hoped for, I realized that I had to take the opportunity with Timely.  The deal was that I had to hang out in Vancouver for a few months to get more familiar with the product, people, and processes so that I could really become part of the team.  Once I felt ready, I could move back to the United States – probably Denver, Los Angeles, or New York.

So it happened.  My longtime job and I parted ways (a mutual decision as it turns out that there was some restructuring going on anyway) and I prepared for the next step.

The job started on July 14th.  I picked Bradley up in San Jose, California and we had several meetings in the bay area.  We met with Gay Cities.  We spent two days in Napa at a trade show as they rolled Timely out across 800 wineries in the region as part of CANVAS.  We met with a major German publishing house and with Eventbrite to talk about our deal with them, sharing an elevator ride down with Kevin Hartz, the CEO & co-founder of Eventbrite.  It was an exciting first week!

Our California trip wrapped up yesterday and we arrived in Vancouver, BC at about 2pm. I’m now ready for my first week at the headquarters!

I was brought on to do marketing and sales, not build this out in the LGBT community necessarily.  But Bradley and I still share the vision of wanting to connect the LGBT community through the calendar and at least some of my efforts will be focused on that. The LGBT community has always been ahead of the general population when it comes to technology and so I wouldn’t be surprised if we were one of the first big groups to adopt this platform.  Obviously we have some competitors in the calendar world but have some key competitive advantages and are the thought leaders in this space (reason I was attracted to the company in the first place).

As things progress, I will update the blog and my online channels.  The plan is still to return to the U.S. in a few months.

If you would like to know more about and how it can monetize your business and strengthen your community, please email me at