Yes, you can email investors and other hard to reach mentor-types. Many of them are on LinkedIn and Twitter; some even have their contact information listed on their blogs. But will it work? Often, no.

While persistence is key in many instances in business, emailing incessantly will likely just turn people off. It's like the deciding moment in the World Cup. You don't get multiple shots, just that one glorious kick that either hits or misses the mark.

So, you've got to score. But how? Like goalkeepers, star players in the business world should be taken by surprise. Here are three unconventional ways that entrepreneurs have used the power of surprise to successfully attract investors' attention:

 inline image

1. Go out of your way. 
This is probably the most expensive taxi ride that Dave McClure of 500 Startups has ever taken. Four years ago, Alex Moore, the co-founder and CEO of Baydin, a Silicon Valley email plugin maker and a TechStars alum, got the chance of a lifetime. He spotted a tweet by McClure asking for a ride to his mechanic, and he jumped.

Moore had been trying to set up a meeting with McClure for a month but hadn't gotten anywhere. This seemed to be a now-or-never moment for the young entrepreneur. He hopped into his car, showed up in front of the investor in 30 minutes, and gave McClure a 40-minute taxi pitch on their way to the mechanic.

After hearing Moore talk about Baydin's main product Boomerang, an email extension that allows users to send email at a scheduled time and reminds them to follow up, McClure made up his mind. He had heard of such tool from several people before, including venture capitalist Katherine Barr and entrepreneur Hiten Shah, who made introductions for Baydin.

"I'm in for 50, maybe 100," McClure said in Moore's car.

Baydin finally secured a $100,000 investment from 500 Startups. As if there was any doubt, it's now confirmed: Eighty percent of life is just showing up.

 inline image

2. Seek one-on-one moments. 
If giving a ride to Dave McClure doesn't sound appealing to you, how about running with Brad Feld?

That's what founder and CEO Reece Pacheco did back in 2009, when he was still developing the New York City-based video aggregation site that was acquired by Samsung earlier this year. When Feld, the managing director of the venture capital firm Foundry Group came to the Big Apple for an event, Pacheco caught the opportunity to meet the famous VC in person.

Feld is known not only for his investment in early stage companies, but also for his passion for running. Pacheco knew that well. At the night of the event, he tweeted Feld to go running the next day. Feld accepted the offer and went jogging with Pacheco at 6 a.m. the next morning. That was just two hours after the founder finished his bar tending job.

Since then, Feld would run with Pacheco every time he was in New York, and even though his company did not invest in, he became a mentor.

 inline image

3. Do something eye catching.
Many investors have their own blog, and entrepreneurs should take advantage of that. That doesn't mean only leaving comments or tweeting about their posts. You can (and should) be more creative--and more willing to take risks.

VoiceBunny, a company that offers professional voiceover at a competitive price, caught Fred Wilson's attention using the investor's own blog. Led by CEO Alexander Torrenegra, the team converted Wilson's articles into a podcast through VoiceBunny's functions and posted them to, as if it were a part of Wilson's blog, Wilson didn't even realize the existence of the podcast until he was alerted by emails asking about

To the team's surprise, Wilson tweeted about the company before they approached him. The venture capitalist was more impressed than annoyed, and wrote an article about the company on the true

"In any case, I like they way they used a stunt to get my attention. So much more effective than sending me an email saying 'I'd like to come talk to you about a new project we are working on,'" says Wilson on his blog.

Wilson ended up embedding the audio files into his blog. Though he did not invest in the company, the mentor met up with Torrenegra several times and gave him the advice to put VoiceBunny and the founder's other project, Voice123, under one umbrella. Now the two firms operate under the company Bunny Inc., together with a music licensing service TuneBunny. VoiceBunny's attempt also amounted to some pretty stellar, cost-effective PR that attracted coverage from media outlets such as Bloomberg TV.

Now, you might think those are fun stories, but they can't be replicated. After all, not every investor will ask their Twitter followers for a ride, neither would every VC go jogging with you. But one thing's for certain: Doing nothing isn't a strategy.