$100K Best of the Fest Investment Prize

The $100k Best of the Fest Investment Prize has always been the most coveted prize at Startupfest, where dozens of founders compete live onstage. We bring together a fantastic team of angel investors—each of whom short-lists one startup from among the attendees. Those finalists then battle it out to see who will be crowned “Best of the Fest”, walking away with not only $100K in new investment, but access to a network of investors and, of course, the coveted Best of the Fest trophy.


Eligibility Criteria

This prize is open to ANY startup registered and at the event – There is no application process, no form to fill out and no video to submit. All you need to do is register for and attend Startupfest, and be ready to pitch to our esteemed Investor Judges.


The Process

Startups have until 3PM on Thursday, July 13th—the second day of Startupfest—to deliver their pitch to the investor judges. They can do so in the language of their choice, but please be aware that since Startupfest attracts investors from across the country and around the world, many of them only speak English.

How do I pitch?

Your goal over the first two days is to get at least one of the Investor Judges to shortlist your Startup:

  • Judges will be roaming the site and based in the Tent Village. We suggest you connect with as many judges as possible—after all, it just takes one judge for you to make the shortlist.
  • Our judges are wearing an Investor Judge badge and a green lanyard to make them easy to identify and pitch everywhere onsite. You probably want to avoid doing it in a bathroom, but everywhere else is fair game!

What happens next?

Pitching ends at 3PM sharp on Thursday, July 13.

  • Each judge will submit their chosen finalist to the shortlist, at which point they will be contacted by a member of the Startupfest team.
  • At 4:30PM, the shortlisted startups will be invited to take the stage for a one-minute elevator pitch (no slides) in front of our audience, to compete for the Best Pitch Award.
  • Friday morning (the 14th) our finalists will meet with the Investor Judges in a private setting, on site.
  • By 12pm the top 5 startups will be selected and notified that they have made it to finals. 

Friday afternoon’s QA and Due Diligence

We’ll introduce the 5 finalists to our audience on Friday afternoon. They will have a 40 min general QA with our Investor Judges, at which point our judges will have a brief deliberation to narrow the finalists down to a top 3. 

Upon announcing our top three, the startups will take the stage together and go through an abridged due diligence process designed to dig into the main challenges of startup growth:

  1. Product, technology and IP (15 min)
  2. Sales, marketing and finances (15 min)
  3. Team, culture, and leadership (15 min)

We’ll reveal the results of this epic contest, and announce the 2023 $100k Best of the Fest Investment Prize winner during Friday’s closing ceremonies. 


Prize Details

The Best of the Fest prize is an investment from up to 10 angel investors. Our default terms are based on an industry-standard convertible note (for reference, please see this standard convertible loan agreement.) The winning startup will sign the convertible note with each of the investors individually. The investors are willing to create a voting trust, if and when the convertible note converts to equity.

Think these terms shouldn’t apply to you? Need a tweak? We can discuss that. While we adopt industry standard agreements for the sake of simplicity, the judges are willing to discuss alternate terms proposed by shortlisted startups during their meeting on Thursday, July 13, during the 5PM private Q&A.

Meet the judges

Josh Felker

Josh Felker 1 (2) 1

Josh is the founder and managing partner at BoxOne Ventures, an asset management firm whose VC activities are focussed on early stage companies across several sectors including fintech, applied ML/AI, synthetic biology/biotech, crypto/decentralized finance.Prior to BoxOne, Josh Felker was the co-founder of the Montreal based proprietary trading firm Vigilant Global. A leader in the most latency sensitive and technology driven areas of trading, Vigilant was an early pioneer in the use of FPGAs and wireless communication technologies in financial markets. Vigilant was acquired by proprietary trading firm DRW Trading in 2012. As partner at DRW, Josh helped oversee a highly diversified global trading firm spanning liquidity provision operations, risking-taking/directional trading, real-estate, venture investing as well as cryptocurrency trading. Josh has a degree in Genetics from Western University and is a father of three.

Gary Pudles

Gary Pudles

Gary A. Pudles is a “serial entrepreneur” who focuses on helping organizations execute better and become more profitable all while having fun. He is the Founder and CEO of AnswerNet, and the co-founder of TextGen, SA Billing, Splendtastic, and Subout. He is a winner of the SmartCEO Best-Run Companies award and the prestigious “Ernst and Young Entrepreneur of the Year” for business service providers and has led AnswerNet to the 21st spot on the Inc. 500.

He also teaches Entrepreneurship at the University Of Pennsylvania’s Wharton School Of Business and is a regular participant in Startup Camp and the Intl’ Startup Festival. Pudles’ philosophy is that every project he is involved in must be with the intent of helping companies run their businesses more efficiently and profitably. However, it must be according to their unique style – not by forcing them into a predetermined template, but by replicating proven processes and adding that custom twist unique to their needs.

Heather Adelson

Heather Adelson (1)

Ms. Adelson has been investing in growing companies for the past 30 years. With over 15 angel investments over the past 8 years, as well as investments in numerous funds and funds of funds, Ms. Adelson’s contributions to the startup community have touched nearly every industry in the Quebec startup ecosystem. With a degree in Commerce from McGill, Ms. Adelson brings her skills in finance, strategy and behavioural elements of business into every deal she explores. Her ability to identify critical success factors and obstacles have led her to a career of interesting investment opportunities and ongoing business relationships.

A consummate “student of investing”, she keeps current with the latest business and technological developments, hones her analytical skills and polishes her professional skepticism through attendance of trade conferences, reviewing business plans and communication with various professional advisors. She is an active member on several boards of both for profit businesses and non-for profit organizations.

Ms Adelson is extensively involved in philanthropic ventures, an area close to her heart. She always seeks opportunities to use her skillset and relationships to amplify the efforts of socially minded organizations. Ms. Adelson has been recognized for these efforts as the recipient of several awards highlighting her invaluable contributions to society.

Anne Martel

Anne Martel Min 1

Anne Martel is a serial entrepreneur, most recently Co-Founder and CAO of Element AI, a Montreal-based AI company acquired by ServiceNow. There, she was responsible for the vision, design, implementation and continuous improvement of operations groups, namely finance, human resources, brand and marketing, government relations and public affairs, and legal functions. 

Anne previously had a successful exit in the medical sector in 2014, where her focus was on manufacturing and distribution of medical devices. She holds an MBA from Kellogg School of Management (Northwestern University), and bachelor’s degrees in Finance and in Fine Arts from Concordia University.

A passionate art enthusiast and philanthropist, she is involved in Montreal’s thriving community of entrepreneurs as a spokesperson, an angel investor, and a board member of OSMO Foundation, a non-profit established in 2009 to help grow the local startup community. She also sits on the boards of the Université de Montréal and of the Montreal Museum of Fine Arts Foundation.

Ian Jeffrey

Ian Jeffrey

Ian Jeffrey is an experienced Montreal-based entrepreneur, startup advisor, and mentor in both Montreal and Silicon Valley. He has a proven track record of building and scaling tech businesses and is a forward-thinking leader in the industry.

Ian's career began after he earned a degree in communications from Concordia University. He co-founded several successful tech startups, including Breathe Life (which was acquired by Zinnia in 2022) and FounderFuel (the first Canadian mentor-driven startup accelerator). Ian also served as the VP of Product Marketing at PasswordBox, which was later acquired by Intel, and the VP of Marketing & Communications at Tiny Pictures, which was acquired by Shutterfly.

Ian's success in the tech industry is driven by his deep understanding of technology, his entrepreneurial spirit, and his commitment to creating work environments where team members are excited to contribute to the company’s purpose, empowered to make decisions, and fulfilled in their daily work. He deeply cares about every individual on his team and ensures that everyone feels a sense of accomplishment in their roles.

Throughout his career, Ian has been recognized as a thought leader in the tech industry. He has been invited to speak at numerous conferences and events and has shared his expertise with audiences throughout North America. He is also a frequent contributor to industry publications.

In his free time, Ian is an avid snowboarder and often hits the slopes with his wife and two kids

Cary Goldwax

Cary Goldwax

Now a veteran Judge at the festival, Cary has been working for over 25-years to bring companies to the next level as a hands-on Angel Investor, seasoned C-Level Executive, active Board Member and a very outspoken accelerator program Mentor.

After co-founding and successfully bringing Web APM company Coradiant to exit, he’s managed several prosperous ventures and exits, currently he is helping bring bleeding edge AI and cloud camera technology to the world as COO of IONODES. He has over 300 million dollars in exits under his belt and is a strong proponent of boosting Canada’s tech scene on the world scale.


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