Born and raised in Wollongong, McQueen had spent the whole night in dissecting the financials of his software company, AffinityLive, trying to find a way to make it work. He had called his cofounders back home to discuss options, as well as a range of prospective investors from his new base in San Francisco trying to bring them across the line.

The company credit cards were at their limits, his personal savings from previous companies were at zero. He was barely sleeping, a long way from home, and running out of options.

When he realised the upcoming payroll would take AffinityLive's bank accounts well into the red, a wash of panic silenced his feverishly plotting brain.

"I was staring into the abyss, and it was numbing. It just felt like I had died inside," McQueen told Fairfax Media.

McQueen had been building AffinityLive, his cloud-based small business management software company, since 2009.

Three years later, the team had survived multiple rejections from venture capital investors to launch the product, develop the team on NSW's south coast, sign up customers and set up in San Francisco.

"A lot of investors at home told me I was nuts. I kept being told the reason a do-it-all-business-management software for small business software didn't exist was it was just too hard. Some were actually pretty unpleasant about it."

With no spare cash, AffinityLive grew slowly. Most of the early growth was word-of-mouth marketing by customers. McQueen had the added cost of moving to San Francisco to be able to open a merchant account that accepted US dollars to cater for the market beyond Australia. He was needed to to American investors.

"Raising in Silicon Valley in 2011 as a small business software solution sucked. Everyone wanted mobile, social and local plays in the wake of Facebook's rise," McQueen said.

"I kept being told, usually quite politely, that I was crazy. Many were gracious enough to say if it took off, it would be huge, but then they would say we don't play our bets like that, it's too far out."

While obtaining investment was hard, customer growth was less so. Subscriber numbers burgeoned, but slowly.

The company had enough revenue to sustain it for the first two and a half years and McQueen drew on savings from his previous successful technology businesses, but when a few key invoices became overdue, McQueen said he had to face maybe the idea was too crazy to work.

"I probably could have raised enough to cover expenses for the next few months, but I didn't want to raise and take it, and then hit a wall a month later. Stretching out the inevitable was morally unacceptable to me," McQueen said.

Out of options, he turned to the only group of people beyond his team who believed in the software: his customers.

He sent a carefully worded two-line email to several who had expressed interest in investing previously but were yet to commit. He told them they had 24 hours to wire the funds or they were going to miss out.

"I didn't say because it's because we were going to crash and burn. They thought they were going to find their seat at the table would be gone."

McQueen shut his laptop, breathed out and waited. He was definitely out of options now.

Surprisingly, even for McQueen, it worked. A handful of investors wired money within hours, followed by a long overdue invoice. It was enough to sustain the company over the next tight few months as they closed a series of key deals and gew the business to the next stage.

AffinityLive now has hundreds of customers and a team of about 20 based in Wollongong and another 20 in San Francisco.

The company had just announced the closure of a $2 million round led by Sydney's Blackbird Ventures.

"We won't get the best headlines for it but we only wanted to raise as much as we needed," McQueen said.

"We don't want to get fat and entitled, and have enough staff to waste time sitting on beanbags talking about all ideation and strategy. Let's get back to work."

The funds will enable AffinityLive to develop its team, particularly in engineering and sales. It also provides the necessary capital reserves for software-as-a-service customer acquisition, which requires significant amounts of capital to sustain customers through their trial periods and into a contract.

Now, McQueen just needs the United States to let him back into their country and his office. McQueen spoke to The Financial Review from a hotel room in Vancouver, Canada, where he had been stuck for weeks after he stepped out of the United States to renew his visa, just as the computer system for the relevant department crashed.

"I'll get back in. But it's one of the many joys of being an Australian entrepreneur I guess. Although, being stuck in Vancouver is nowhere near as good as being able to walk to work in Wollongong and go surfing at lunch time."