Here's how five entrepreneurs took bold, sometimes off-the-wall approaches, to funding their businesses or expansion plans:

Get to the right place, at the right time

Alex Moore and Aye Moah once struggled to find funding for Boomerang, an email productivity tool under their company Baydin. Meetings with around 35 angel investors led nowhere, and they couldn't seem to lock down a visit to pitch Dave McClure, founder of the business incubator 500 Startups.

That changed when Moah caught McClure's tweet one day:

"Need ride," part of it read. "Will hear startup pitch in yr car."

The duo raced to McClure. And while they say he spent some of the half-hour ride striking a deal--with someone else over his phone--he also discussed Boomerang. As it turned out, McClure's assistant had already been using the program and he verbally committed $50,000 on the spot, which he later upped to $100,000. Moore and Moah soon relocated from Boston to Mountain View, California.

"We decided if things like this happened we'd move out here," says Moore. (In an email to me, McClure confirmed the married couple's account and noted, "I also attended the founders' wedding.")

Make a lasting impression

Sam Rosen once established SpeakerGram to help thought leaders with book speaking engagements. To secure money for his company, he targeted investors such as Gary Vaynerchuk, a partner at Vayner RSE, a seed fund that backs startups.

Upon hearing that Vaynerchuk would be at a nearby book signing, Rosen borrowed a friend's car to get there then staked out a spot --at the back of the line.

"Instead of putting a book in front of him to sign," recalls Rosen, "I took out my convertible note, slid it across the table and said, 'I heard you were in the mood for signing things.'"

The tactic wasn't enough to get Vaynerchuk interested in SpeakerGram, which later shut down. But the investor did recall Rosen's passion in 2013 when an opportunity arose to invest in another startup of his--MakeSpace Labs, a full-service moving company.

"I loved his bravado and intensity--exactly what I look for in an entrepreneur," says Vaynerchuk, who along with his brother invested $25,000 in MakeSpace.

Convert customers into advisers--then investors

When Freshii opened in Toronto in 2005, three customers spent so much time at the restaurant that they became friends then informal business advisers with its owner, Matthew Corrin. In time, Corrin started raising money for Freshii's expansion into the U.S., and while he initially hesitated asking his buddies for money, he eventually found the right, lighthearted wording:

"Between you and your family, you're spending about $3,000 a year at the restaurant. You might as well own a stake in it so that 10 percent of that sale is actually yours."

To Corrin's surprise, each agreed and invested a total of $1 million in Freshii, which has since expanded to more than 100 locations in around a dozen countries.

Customize your ask

In 2012, Tim Sae Koo experienced the kind of meeting many startup founders dread: an investor showed interest in his business but said he'd be in touch.

"Any entrepreneur knows that's probably a 'no,'" says Sae Koo, CEO and founder of Tint, a social media platform service. "I needed credibility."

So he spent about a week customizing Tint's platform for Shark Tank investor Mark Cuban. Then he emailed Cuban (three times) and asked for feedback. When Cuban finally responded, Sae Koo followed-up with his biggest ask--"If I populate a tweet, could you copy and paste it and see what your fans and businesses say?"

It worked. While Cuban tells me he can't recall this particular email exchange, he did plug Tint (then called Hypermarks) to more than 1 million of his followers, which Sae Koo says triggered a rush of new users. Sae Koo then successfully convinced other influencers--Steve Case, Tim O'Reilly and Robert Scoble-- to send supportive tweets of their own.

"The investor decided to finance $350,000 into our company not solely because of the tweets, but because I proved that I could think outside the box and execute the hustle to get to the top," says Sae Koo.

Published on: Feb 17, 2015