Rob Darling likens it to a first date.

The founder and CEO of WellRead, a startup that helps businesses find the right expertise through platforms such as LinkedIn and Twitter, is gearing up to meet with four or five venture capital firms at Communitech’s Techtoberfest.

The goal is to raise investment cash for his fledgling company but he has no illusions that the funds will materialize right away.

“Today it will be more like a casual conversation,” says Darling, whose startup has three employees and launched its product, LaunchSpot, about a year ago.

(Photo: Darin White for Communitech)

(Photo: Darin White for Communitech)

But he has high hopes that Friday’s encounters with potential VC partners will eventually lead to a steady relationship and some dollars down the road. Darling’s goal is raise $2.5 million in venture funding to “ramp up sales and marketing.”

Asked if he’s optimistic about the upcoming pitches, he smiles and says, “Always.”

Darling was one of about 30 startup founders who gathered on the fourth floor of the Tannery building Friday afternoon to pitch to about 25 venture capital firms. Entrepreneurs met with investors in one-on-one sessions of about 30 minutes each.

Space was provided free of charge by Desire2Learn and furniture was supplied by Mayhew in the unfinished corporate office.

Among the venture capitalists on hand was Sunil Sharma, managing partner with Extreme Venture Partners of Toronto.

Sharma was hoping to meet with as many early-stage companies as possible during the two-day Techtoberfest event. Communitech and the Waterloo Region community do a great job of “curating companies,” says Sharma whose firm has invested in about 30 startups in the Toronto-Waterloo corridor over the past few years.

On his radar screen were entrepreneurs specializing in connected, mobile and wearable devices. A new area that has piqued his interest is “open data.” Governments are making more and more information available on topics such as pollution, population, crime and census data, he says.

The ground is fertile for startups in this field, Sharma adds.

Pitching to venture capitalists might seem like a nerve-jangling exercise for most young entrepreneurs. But not Justin Bailie. He was cool as a cucumber as he waited his turn in a lounge area next-door to the pitch room.

FR8nex co-founders Justin Hein (right) and Justin Bailie. (Photo: Darin White for Communitech)

FR8nex co-founders Justin Hein (left) and Justin Bailie. (Photo: Darin White for Communitech)

Bailie, whose company FR8nex helps small and medium-sized companies simplify their freight shipments, pitches every week to customers and other investors.

“We’re well practised,” he said confidently.

Founded nine months ago in Toronto with partner Justin Hein, the company has six employees and is hoping to raise “a million plus” in seed financing to expand its team, build more features into its platform and kickstart more sales, says Bailie.

But he’s not expecting any cheques to be signed today. “We’re not here to get a deal today,” he says. “Our ambition is to build a good business first and if we do the right thing, the money will come.”

Bailie describes FR8nex as “Expedia for freight.” With one keystroke, a customer can call up all the trucking companies in the area and tender every shipment, he says.

A venture capitalist who has been through all this before is Jim Estill, founder of Canrock Ventures. Through Canrock and on his own years before, Estill estimates he has invested in more than 150 startups. He was planning to meet with six startups Friday afternoon after picking candidates from a list of about 30 early-stage companies.

Traditional tech firms are mostly what he likes to invest in, says the former computer distributor who founded EMJ Data Systems, then sold it to Synnex Corp. “I don’t do biotech or games companies,” he explains.

Estill was looking for more than just a good idea or product. The key is in the execution, he says. Any city has tons of restaurants, he notes, but only the ones who execute well survive over the long term.

Brian Hunter, a venture capitalist from Cambridge, was calm and laid-back as he relaxed in the lounge prior to meeting with several entrepreneurs.

Brian Hunter, founder, NorthSpring Capital Partners (Photo: Darin White for Communitech)

Brian Hunter, founder, NorthSpring Capital Partners (Photo: Darin White for Communitech)

“I’m not necessarily looking for new companies to invest in,” said the partner with NorthSpring Capital Partners. “They find me.”

Hunter founded NorthSpring five years ago with two other partners. The company invests in small and medium-sized firms in tech and traditional industries. It typically does deals in the $250,000 to $1 million range.

While he was decidedly low-key about finding the next big thing among the early-stage firms in attendance, Hunter admitted he didn’t want to miss out on anything.

“I like to keep informed. There are a lot of great startups in this town.”

John Read, founder of Colibri Software, travelled a long way to pitch to venture capitalists on Friday. His four-year-old company, which makes an “exploration tool” that helps people set up guided tours on mobile devices, is based in Wolfville, N.S.

Despite travelling such a distance, he had modest ambitions for his upcoming encounter with VCs.  He’s hoping to raise “awareness” about Colibri. “We’re not at the point of raising X amount of dollars yet,” he says.

Read was also eager to get some tips from the VCs on how he can bid more effectively for investment cash.

“I’m pitching for feedback,” he says.

As for WellRead’s Rob Darling, he ended up meeting five VCs, secured follow-up meetings with all of them, and sold two of them on LaunchSpot.

“The afternoon was well-organized; it was great to meet all those people,” he said. “Where else would you get this kind of opportunity?”