Jay Whitelaw | Crain's

In this ongoing series, we ask executives, entrepreneurs and business leaders about mistakes that have shaped their business philosophy.

Jay Whitelaw

Background:  

Givesome is a nonprofit based in Guelph, Ontario that seeks wants to transform how people around the world give to charities, by offering the ability to donate in micro-transactions.  After charitable projects from around the world are funded and completed, users of the Givesome app can see firsthand, through photos and videos, how their contributions have improved lives. With several major charities and corporate sponsors already in place, the Givesome app launches in the Apple App Store March 20.

The Mistake: 

I wish I had shared my plans for a new business with people sooner. 

I had definitely made the decision to go for it, but I wasn't telling anyone else. Because I knew that as soon as I did, then I could fail. I had quit my job, and I was telling people, 'Oh, I'm just looking around,' but I wasn't, really. I was starting Givesome. 

I had told my wife and maybe my parents what I was doing, but I hadn't come out and told my friends or anyone else. They thought I was just job-searching. So as long as I kept it to myself and did things on my own, on my own little mission – then if I failed, only I would know about it. 

I had one guy who knew what I was doing kick my ass one day over coffee. He was an older mentor to me, and he was the one person who knew what I was up to, whom I trusted to share it with.

I'll never forget when I first told him. I could show you exactly where we were sitting. I risked it with him, and when I told him, he broke down and started crying. He's a mentor to a lot of people, but he said 'Look man, as often as you want to meet with me, I'll meet with you, because I want to help bring this vision to life.'

The second time I met with him a couple of months later, I think he picked up on the fact that I hadn't told anyone else yet. He said, 'You've still never talked about it. I haven't heard you say anything once.' So based on his challenge, I said, 'Fine, I'm gonna go for it,' and burn the boats, so to speak.

Good things don't start happening to you until you really go all in. 

The Lesson:

The day after I told him I would be honest and real about it, I was in a dentist's chair. It was my first time at this dentist for a checkup, and the woman doing my teeth was making conversation and asked me what I did for a living. As soon as she said it, I knew this was my opportunity to tell someone, so I stuck to my guns and said, 'I'm the founder of Givesome.'

I explained it to her, and honestly, she took off her mask and turned her chair around, sat down and looked at me, and said, 'You need to tell me more about this.' It turned into about a 15-minute talk. until the actual dentist came in. And he was kind of upset she hadn't worked on my teeth yet, until she said, 'You need to hear what this guy's doing.'

So he sat down too, and I explained it to him, and I had this audience of two people for about 20 minutes. Then they worked on my teeth. And I walked out thinking 'Wow. I've wasted all of this time.' There I was, about eight months to a year into doing this in private, and the very first time I started talking about it, I got this great reaction. 

As soon as I started talking about it, then momentum started to build. One of the first people I told happened to lead me to a speaking engagement a couple of weeks later, and that's what really kicked things off. I saw how much momentum came after that, and wish I had done it a lot sooner. 

So you have to talk to people, especially in the early days, to build momentum. As long as you're playing it safe, it'll never move forward. But as soon as you tell people, especially if it resonates with them, those people will email you, they'll call you, they'll want to go out for coffee with you again for an update. Being safe isn't what's going to move you forward. What pushed me forward was knowing that I was going to have to answer to those people, to tell them what I'd done and what steps I'd taken.

Good things don't start happening to you until you really go all in. 

Follow Jay on Twitter at: @givesome_gives

Photo courtesy of Givesome.

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