Written by Andrew Seale

From Keren Moynihan's perspective, this persistent risk-averse funder versus bootstrapped founder dichotomy won’t do. The differences are thin, overplayed even.

“These two groups of people – whether they're equity investors, crowd funders, market exchanges, or anyone giving access to capital – I feel like it's so easy to put them in one bucket and say I'm a founder, I'm in a different bucket,” says Moynihan, co-founder of Boss Insights. “But it does not represent reality.”

Truth is the focus on how hard it is to raise funds, neglects how hard it is to be an investor.

“They have to meet with 500 to 1,000 companies to pick one to invest in, repeat that ten times and then one out of ten of those will actually succeed,” says Moynihan, who spent over a decade working in the capital markets. “They could get much easier jobs being corporate bankers working with later-stage companies.”

In a sense, Boss Insights takes aim at the dichotomy in hopes of making life easier for both funders and founders. Investors need information – the early-stage market can be risky – and entrepreneurs are after “smart money” from people who can help them gain access to markets, capital, and talent.

Boss Insights’ cloud-based portfolio management software tracks key information about startup companies and leverages AI models to predict if a company will fundraise, grow their team or exit via an Initial Private Offering or merger. It digitizes a lot of the legwork funders typically undertake, saving them time and helping them make better decisions about where to put their money.

Moynihan’s husband Luke initially came up with the shell of the idea in 2013 while streaming shipping costs for Amazon. “He noticed that if you have great talent and budget for great tools you can really solve any problem,” explains Moynihan. The idea lingered and in 2017, with the startup scene exploding in Toronto, they realized they could create a more efficient way of connecting funders and founders by collecting the right data in one streamlined tool.

They tested their AI prediction models on 2013 data from 1,000 companies. “Our predictions were 63 to 94 per cent accurate compared to an ecosystem that is batting one-out-of-ten,” she says. “Not saying that we’re much better, but we were just making the argument that data science has a role to play.”

Boss Insights went to market in summer 2018 and is in the seed stage with their first customers already onboard. The startup is a part of iBoost at Ryerson and VentureLAB in Markham.

“I feel really lucky… in Canada we have so much more support than you would have in other places and as a result, you sound more sophisticated as a founder,” says Moynihan. “It is way more different running a business from an ecosystem where you learn terminology, have access to mentors, have doors opened to you that would otherwise never be opened, and yes, so much funding.”

She says it’s a pivotal time to be a woman founder, especially in a country like Canada where the conversation surrounding what that truly means is “happening in such a loud way.” It’s an added bonus behind Boss Insights, a platform that affords very little room for biases, something Moynihan will help drive that diversity conversation.

“The point isn't that we need to go hire diversity and hire women, the point is you need to take off whatever blinders you have and go with merit,” she says. “I think a tool that puts merit in front of your face as a snapshot will allow people to do that, it is really hard to argue with the numbers  – that's our approach to it and what we're trying to do to change the score.”

Photo credit: Cameron Bartlett (www.snappedbycam.com)