I have failed enormously over the past two years. Here's what happened, candidly. 

 

A TICKET FORWARD

A Ticket Forward was an incredibly romantic idea - and it failed dramatically. The idea was simple: "What if we leveraged the momentum of the viral story to create a pay it forward charity that would send deserving people on trips to reconnect families and give a helping hand to those in need?" Amazing, right?

In less than five weeks, we built a team, offering, raised initial donations from Marriott International that covered the cost of setting up the charity, found initial beneficiaries and launched the organization on none other than Good Morning America. 

We thought we would raise millions and millions of dollars. Our advisors, who were seasoned philanthropic experts, believed we'd raise tens of millions of dollars. Our team was motivated to change the face of travel. I borrowed nearly a $100,000 personally from my parents to hire the best public relations people in the business who represent the American Red Cross, The Blue Water Project and The Malala Fund. 

We earned 700-million media impressions globally. And how much money did we raise? Less than $10 per million media impressions... less than $6,000 USD in total. So we tried to forge corporate partnerships with every major player in the travel business - and no one wanted us once the viral story ended. In the end, we couldn't afford to send one beneficiary anywhere without completely killing the organization. It was a humiliating disaster. 

So I made the very difficult decision to freeze everything. And in that shameful state, I eventually deleted the website and didn't even renew the domain name. I was horrified. 


TRIPLUST

During the demise of A Ticket Forward, we believed there would be merit in trying to build a social enterprise side of the charity that we could then leverage the profits of to save the charity. 

The concept came up: Triplust, an app that connected travellers and locals in cities around the world for advice, lessening the need for Tripadvisor and Yelp. Besides we all want to travel like a local, right? 

We put together a prototype and business plan and applied to every accelerator imaginable. We were thrilled to get an offer of admission to join The Brandery in Cincinnati, Ohio, one of the top 10 startup accelerators in the United States. And so we moved down. 

A little over half way through the four month program, the founding team blew up. There were three of us. The details don't matter, suffice to say that challenges relating to trust blew us apart. I was committed to staying in Cincinnati and presenting on Demo Day, the day at the end of every startup accelerator where investors from all over the US fly to see if any startups catch their eye. 

But it wouldn't been Triplust that was presented. It died when the founding team did. 

 


BOUNDE

While living in Cincinnati alone, after Triplust blew up, I was at an all-time low. My long-term depression was in its most severe state. Looking back on it, I was very close to harming myself beyond repair. How could I mess all of this up? How could I have had the world's attention and failed to drastically? (There were other failures, too, beyond these listed here. There was a TV development deal that was mismanaged, a film rights fiasco and other things that nothing can ever prepare you for). 

But the worst of all was that I hated myself. I hated the mess I had created. I hated the person I was before all of this, and especially detested who I had become during all of this. I was wearing a mask. I was a fake. I wanted to be somebody so badly that I'd do anything to get there, wherever there was. 

A mentor came to see me. He cared when very few others did. He knew how bad I was and over a course of weeks he convinced me of a simple truth I refused to believe: That I was more than the viral story, this startup, or any of this shit. I was enough - and I always had been. I had just been scared. 

It turned out that what I needed most was to be able to talk to someone that understood. Someone that I could be brutally open with. Someone that had been there in their own way. 

And it hit us: Using the code of Triplust, an app would be created that would allow for anonymous peer support. So while Triplust was effectively a chat application for travellers and locals, Bounde - as it would be called - would be an app for people that need support matched with people that have been there. It would be organized by key life changes and would be an anonymous, safe space led by moderators and for-hire experts in different areas of personal development. 

I presented this on Demo Day. And, all things considered, it went pretty well. We got the interest of investors and were able to begin to look at a future of building a company. It was coming together. I recruited new business partners, we advanced the product, focused on the business model, got into MaRS (no small feat), and worked with Tom Chi and FactoryX to test the product (also no small feat). 

During this we were putting together a round of investment that would keep us going for 18 months and allow us to build a team. I cannot speak about what happened next publicly because of unfolding legal matters, suffice to say our lead investor turned out to be doing something highly illegal using his close relationship to us and we had to kill the company while criminal charges have been filed against him. 

His actions prevented us from helping millions with Bounde. We had also repurposed A Ticket Forward and rebranded it as Bounde Foundation so that we could closely manage its programming using the resources of the team. We had to freeze the charity too, sitting on all personal donations which will be passed to an effective and life saving charity as soon as we can. 

And as of May 2016, it was all over. Everything was frozen. I had to sell my home to cover immediate debts, while beg our lawyers for fee forgiveness. Bounde could have, and still one day might, help millions of people feel less alone. But that dream was scuttled by the actions of one man - and my failure to not stop him sooner. 

Which brings me to everything I do today. What a journey, right?