How I Learned to Ask Investors for Money

I've really never liked asking other people for money. But until I make it to the PGA Tour, relying on investors is part of my business model. Sponsorships and tournaments alone aren't enough to pay for me to travel 300 days a year. And it takes quite a chunk of change (about $96,000) to keep things moving.

Unfortunately, when you're trying to raise money as a young, professional golfer, you don't have any business development people to do the deal for you. It's just me cold calling potential leads and walking into meetings to give my own pitch. When I was first starting out, I made all kinds of rookie mistakes. Here's what I learned along the way:

I couldn't answer the "why" question. I'd be in front of someone who I was hoping would invest anywhere from five to seven figures in my golf career and when he'd say, "So tell me why it makes sense for me to back you," I would have no idea how to answer him. I think I figured that if I could just prove I was a nice guy, the investor would write a check. (Didn't happen.)

I lacked confidence in who I was and what I was about. Over time, I've learned how to explain myself. I tell a simple story about an honest southern guy from Knoxville, Tenn., who is willing to do whatever is necessary to get to the PGA Tour. There's no gimmick.

I didn't own the conversation. Early on, I thought that maybe if I rehearsed my answers to certain questions, the meetings would go better. (They didn't.) I found myself coming out of these meetings frustrated that the investor didn't ask me any of the questions I was prepared to talk about.

The real problem was that I didn't know how to answer the question I wanted to answer. I'd let the other guy dictate the terms of the conversation. Now it's much more of a give and take. I've become better at telling my story, which helps, but I've also realized that this isn't just about an investor making a decision -- I'm making a decision, too, and I want to make sure the arrangement is a good fit for me. That's helped give me more confidence.

It took me awhile to realize that I didn't always have to ask for money. I used to look at my projected expenses and think, "OK, that's a lot of cash I need to raise." So I'd go to these investor meetings and if someone decided not to give me money, I'd leave and that was the end of it. I met one guy in particular who was the nicest guy in the world but after a long conversation, he said he wouldn't give me any money. I was ready to get up and walk out, but he kept talking. No, he couldn't give me any money, he said, but he could give me something that might be more valuable: Delta SkyMiles.

I had one of those why-didn't-I-think-of-that moments. Those SkyMiles help take care of a huge chunk of my travel budget and the arrangement turned out to be better than a straight cash investment: Unlike my other investor deals, I didn't owe him any future winnings. In exchange for the miles, I wear his company logo on my sleeve. It's good old-fashioned bartering.

I still don't really like asking other people for money, but it's no where near the frustrating task that it used to be. Have any of your own fundraising tips? Tell me in the comments.