Here’s what we’ve learned from 9 years and millions of dollars in opportunities and pitch competitions

Each year at Startupfest, founders receive hundreds of thousands of dollars in investment through various pitch contests. Many are aimed at a particular vertical, such as Fintech or new media; others are for specific stages of growth of founder backgrounds.

This year, the investment prizes and opportunities increased significantly—totalling over a million dollars in backing. And while winners were thrilled with the support they received, we want to clarify our pitch programs and investment prizes to ensure they’re working for as many deserving startups as possible.

Why we do it

We run Startupfest because we want the best founders and new business ideas to receive the backing, support, and attention they deserve. In short, we want as many people as possible to be able to create amazing companies.

We do this in a number of ways:

• Deep, long-form content taught by experts, as well as accessible speakers and interactive formats. This content is aimed at specific tiers of growth, from early-stage founders to startups seeking funding.
• Inclusion initiatives that ensure everyone has a shot, with specific emphasis on female founders, indigenous entrepreneurs, and under-represented groups. We greatly appreciate the support of BDC Capital, Fasken, and Microsoft for Startups in making this possible, as well as groups like Queertech Montreal who help us spread the word.
• An inclusive event, with nonbinary washrooms, a clear code of conduct, pronoun stickers, childcare options for speakers, and a welcome environment for young children whose parents want to attend.

• Diverse speakers. We believe that the best way to ensure a broad range of startups is to represent that on stage. Startupfest 2019 had 53% female speakers, and roughly 40% of attendees were female.
• A newly-created $100K investment prize for companies whose most senior executive identifies as female. In addition to supporting the Federal government’s goal to double the number of female entrepreneurs by 2025, this is good business: More diverse organizations produce better results.

Prizes are just one of the ways we can lift up founders.

What we do today

Today, Startups prepare their pitches before arriving at the event, then sign up for those pitches onsite. Lines are often long (even though we encourage founders to come back at their appointed times, the queues for the investor pitches and grandmother pitches stretch a long way across the site.)

While Startupfest organizes many of the pitch contests, some of the programs are run by partners. For example, Banque Nationale brought their very own elevator to the tent village for “elevator pitches.” So a lot of the pitching is onsite serendipity.

The criteria and format of pitches varies. Some are short, 30-second qualifiers for a single speaker; others involve the founding team. Some require nothing but a speech, while others allow documents, demonstrations, or slides. Some are grants or simple prizes, while the larger prizes are actual investment complete with a term sheet.

While there’s basic information on each pitch available on the website, most of the details are in the mailings we send out to attendees in the week leading up to the event, as well as our Medium blog, where we lay out additional information.

How we run the big prizes

While there are dozens of prizes at the event, most of the attention goes to two $100K awards that come in the form of a term sheet. The process favours hustle: Any founder onsite can pitch an investor judge, identified by a blue lanyard, at any time. Founders can also sign up to pitch the judges as a group.

This was our first year running the $100k Women in Tech investment prize. Startups pitched our judges, who didn’t know at the time whether the applicant qualified for the Women in Tech prize. The shortlist of the best pitches was then reviewed to pick a winner, and reviewed a second time to pick a winner that was led by a woman. In other words, a woman-led company could win both prizes.

When we introduced the new prize on Medium and via our newsletter, we defined it as being “for a female-led startup, which is qualified as: the most senior member of your executive team identifies as female.” Elsewhere, we simplified this to “woman-led startup.”

We thought long and hard about the wording of this, and solicited feedback from a number of founders and investors.

• We didn’t want to say “50% women-owned.” While this is a common criteria of some prizes and government programs, it prevents most woman-led companies who’ve accepted investment from qualifying.
• We also recognize that org charts in startups are fluid, with founders wearing many hats. Some companies don’t have a CEO — just a pair of co-founders. So we felt that “most senior member of your executive team” was the best way to capture that.
• And of course, “identifies as female” is worded to ensure we’re inclusive of the many LGBTQ2 founders who participate every year.

Our decision was to cast a wide net and deal with exceptions — such as a pair of co-founders — on a case-by-case basis. Then, as the judges deliberated on finalists, our Occam’s Razor would be, “does the most senior person in this startup identify as female?”

What we can do better

While these initiatives have been incredibly well-received by the startup community, we know we can continue to learn and improve. Some of the issues we’ve encountered include:

• Standing in line too long. Even though we tell applicants they can return just before it’s their turn to pitch, many waited for over an hour. We’d prefer they explore the many amazing connections and talks to make the most of their experience.
• Not knowing what to bring to a pitch. Most founders have an elevator pitch ready to go, but if they need to bring additional material or adjust to a particular time limit, they may have to adapt on the fly.
• Lack of clarity in who can qualify for a prize.
• Lack of information about the specific terms of an investment ahead of pitching. While our investors use industry-standard documents — such as the BDC Convertible Note, for example—some companies may be too far along to accept a predefined term sheet without negotiation When that’s the case, founders may propose what they’d offer in return for an investment.

What we’re changing

While we’re thrilled with the results of this year’s event, we know we can still do better. So here are some of the things we’re planning for 2020:

• A signup model for all pitches and prizes. Attendees will be able to choose which prizes they’re applying for, and receive tailored information in advance on the criteria and format, as well as details of how the award will be delivered (such as the term sheet, or how to access in-kind services.)
• Using SMS and a scheduling model to notify founders when it’s their turn to pitch, so they can make the most of their time on site.
• A dedicated web page for each prize within the Startupfest site, so that even if a startup didn’t select the prizes they intend to pitch for ahead of time they have access to prize terms onsite.

We received hundreds of responses from attendees in our follow-up survey (if you haven’t completed it yet, please do!) that were almost unanimously positive. But we continue to look for ways to create the world’s most inclusive, founder-focused startup event. So if you have suggestions for how we can improve the experience even more, please let us know.