2 x $100k Black Entrepreneur Investment Prize

Made possible by Rep Matters, the $100k Black Entrepreneur Investment Prize is back for its fourth year! With a mission to empower the next generation of Black startup founders, Rep Matters is DOUBLING THE $100K PRIZE and bringing together a team of angel investors and venture capital firms who will award TWO Black-led startups with a $100k investment.

 

Eligibility Criteria

The $100k Black Entrepreneur Investment Prize is open to any Black-led startup in attendance. For the purposes of this prize, we define a Black-led startup as a startup with the most senior member of the executive team being a Black leader.

There’s no application process, no form to fill out, and no video to prepare. You just need to register, get onsite, and be ready to wow our Black Entrepreneurship Investor Judges with a superb pitch that makes the cut.

 

The Process

Pitching
Your goal is to get at least one Investor Judge to shortlist your startup during the first two days of the event.
  • Pitch your startup to the Investor Judges at the $100k Black Entrepreneur Investment Prize space in The Startupfest Village.
  • If you connect with a judge elsewhere onsite, you can ask to pitch to them on the spot! Connect with as many judges as possible; it only takes one to make the shortlist.
  • Judges will be wearing an Investor Judge badge and a green lanyard to pitch onsite. Avoid pitching in bathrooms, but anywhere else is fair game!
  • Your pitch needs to be no more than 1 minute but be prepared for questions from the Investor Judges.
 
The Shortlist Process
  • Each Investor Judge will submit their chosen startup to the shortlist by Thursday afternoon, July 10th. Shortlisted startups will be contacted by a Startupfest team member.
  • The evening of Thursday July 10th and morning of July 11th shortlisted startups will be invited to a pitch and preparation session with select prize mentors. These mentors will help prepare startups for the finals.
  • 10 startups will be named as phase 1 finalists. After additional pitches of these 10 startups 3 will be selected for phase 2 of the finals. 
 
The Finalist Process
  • On Friday, July 11th, phase 2 finalists will have 1 minute to pitch their companies on the main stage to the audience. This is followed by a Q&A with the Investor Judges.
  • The two winners of the $100k Black Entrepreneur Investment Prize will be announced at the closing ceremonies on Friday afternoon.
 

Prize Details

The $100k Black Entrepreneur Investment Prize is an investment from up to 10 angel investors. Our default terms are based on an industry-standard SAFE agreement (for reference, please see this standard SAFE agreement). The winning startup will sign the SAFE agreement with each of the investors individually. The investors are willing to create a voting trust, if and when the SAFE agreement converts to equity.

Think these terms shouldn’t apply to you? Need a tweak? We can discuss that. Not sure how to tweak? Don’t worry that is why we have mentorship and legal support for all finalists. 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.

Startupfest does not guarantee that an investment prize will be awarded. All investment decisions and agreements are made solely at the discretion of the participating investors and the selected startup.That said, we’re proud to share that over 95% of the approximately 30 Startupfest investment prizes awarded over the past 15 years have successfully closed.

 

2025 Judges

Host: Phil G. Joseph

Phil G. Joseph is an investor, changemaker and community builder who explores the intersections of culture, technology and venture capital to build towards a future where all can thrive. He is a Senior Investment Associate at Real Ventures, and the founder of Rep Matters, a non-profit focused on empowering Black tech founders. Rep Matters launched the Black Entrepreneur Investment Prize at Startupfest in 2022, and is proud to bring together Black founders, angel investors, and supporting organizations each year since.

 

Melissa Allen

Melissa Allen launched her career in digital marketing—working at companies like Torstar Digital and Google—before earning acclaim as a wealth advisor at Desjardins. In 2019, she became an angel investor and Limited Partner, then moved into startup advisory roles, including Bay Mills and Alo Solutions. From 2022 to 2024, she served as Executive Director of League of Innovators and Venture Partner at LOI Venture. She is currently the Founding Partner of Capital M Ventures, a venture capital firm backing diverse Canadian founders. 

Frank Baylis

Frank Baylis is a Canadian engineer, entrepreneur, film producer and philanthropist. He led Baylis Medical, the company his mother founded, from 1989 to 2021—which he helped scale into a global medical-device leader before its USD 1.75B acquisition by Boston Scientific. Frank also represented Pierrefonds–Dollard as a Liberal MP from 2015 to 2019, later running for Liberal leadership in early 2025. He now serves as Executive Chairman of Baylis Medical Technologies and President of the Gloria Baylis Foundation, which he founded in an effort to enhance the lives of individuals by providing access to education, healthcare and equal opportunities for community advancement. 

 

Andrea Nicholls

Andrea Nicholls, CPA CA, CPA (US), ICD.D, GCB.D is a seasoned finance leader serving as Chief Financial Officer at Dentons Canada LLP, where she co‑founded Dentons’ Black Professionals Network oversees a team of over 100 professionals and finance strategy for the Canada region. She began her career at PwC Montreal and held senior finance roles at GE Capital, Otéra Capital, Triton Digital, and Metso. Andrea also served on the Board of HSBC Bank Canada before it was purchased by RBC, and currently sits on the board of Centraide du Grand Montréal, The Conference Board of Canada, the McConnell Foundation and CAMH. 

 

Tania Clarke

Tania Clarke, FCPA FCA, CPA (US), ICD.D, CCB.D, GCB.D is a senior finance executive with broad experience in the public and private sectors across various industries. Tania began her career at KPMG before moving into senior roles at companies such as Grand Toys, Keurig, and New Look Vision Group. She now sits on multiple boards including Futurpreneur, the BDC, and Jamieson Wellness. Tania has remained active in her community by serving on many nonprofit boards, as well as actively mentoring young professionals in their career and personal journeys with Audace aux Feminins and The West Island Black Community Association. 

 

Amoye Henry

Amoye Henry, MBA, is the Co-Founder of Pitch Better Inc., an award-winning market research firm advancing equity by supporting underrepresented founders through national research and data-driven insights. She is also the newly appointed Managing Partner of FoundHers Ventures, an early-stage fund fueling innovation in the digital and green economies. A 3x founder, investor, author, and mission-driven strategist, Amoye has built and led education programs for entrepreneurs across four continents, working at the intersection of instinct and resilience to scale growth-stage ventures led by bold, underrepresented leaders. Her efforts have helped secure millions (approx $20M) in funding for tech entrepreneurs, startups, and innovation-driven organizations, solidifying her as a transformative force in the global business landscape.

Michael Dennis

Michael Dennis is a senior executive specialized in financial systems implementations across a variety of industries. He started his career in corporate accounting before moving to Hyperion, where he held several roles in Consulting and Sales. He then founded ToMont Solutions, which grew to become the largest Oracle EPM Consulting firm in Canada prior to being sold to KPMG. Michael then spent four years as a Partner at KPMG where he continued to drive transformation through technology in the Canadian market. Today, Michael is the Managing Director of Canadian Business Operations at CompIntelligence, a financial solutions consultancy, and also sits on the board of the Trevor Williams Kids Foundation.

Joseph Clement

Joseph Clement is an experienced financial markets professional based in Montreal. Educated at Université de Montréal, he specializes in trading and portfolio strategy for institutional clients covering hedge funds and pension funds. At Raymond James as an Institutional Equity Investor for the past 15 years, Joseph has built a strong reputation for market insight and disciplined execution. He is also dedicated to mentorship and professional development within the financial community, helping emerging traders refine their skills and industry knowledge.

Diogo Barry

Diogo Barry, B.Sc.A‑g, MBA, is an entrepreneur, investor, and operational specialist. Born in Guinea and educated at UQAM (BBA, 2010), he went on to gain deep experience in SaaS, business intelligence, and customer relations, which he put to work at companies like Luxury Retreats (acquired by Airbnb) and Pomelo Health (acquired by Telus). A visionary operator and process-optimization expert, Diogo is passionate about digital transformation and scaling tech ventures through strategic, data-driven execution. Today, he is the co‑founder and Chief Revenue Officer at Chrono Innovation, a Montreal-based software development company, and is also an active investor.

Bola Ogunremi

Bola is a former pharmacist with nearly 20 years of experience in Nigeria and the UK. In 2018, she founded Olorire Inc., an investment company focused on real estate and tech-enabled ventures. She also leads investments at BOG Medical. As a sector-agnostic investor, Bola enjoys identifying and supporting startups that use data insights and technology to enrich human experiences. Her investments to date include ConeLabs, Gloopro, Regimen Ai, and others. Passionate about impact, Bola advises the African Social Enterprise Workshop, a platform that offers training, mentorship and resources to African social innovators to enable sustained impact across the continent.

Gajan Kulasingam

Gajan Kulasingam, CFA, CPA, CA, is the Managing Partner at BOF Capital, a first-of-its-kind initiative dedicated to tackling systemic economic barriers and building generational wealth for Black communities. As a seasoned investment executive, Gajan is leading BOF Capital's strategic direction, ensuring its funds create meaningful, long-term impact for Black entrepreneurs and homeowners. BOF Capital was launched by the Black Opportunity Fund (BOF), a community-led registered Canadian Charitable organization, that supports a prosperous, healthy and thriving Black Canada. The BOF is led by Craig Wellington. 

Alfred Burgesson

Alfred is the Founder & CEO of Tribe Network, a community supporting racialized entrepreneurs with access to capital, coaching, and networks. He also leads Tribe Ventures as Managing Partner, investing in transformative businesses and technologies. A 30 Under 30 Innovator, Alfred serves on boards including the Black Opportunity Fund and Engage Nova Scotia, and has been a trusted voice in national policy making as a former advisor to the Prime Minister of Canada, First Nations Chiefs, and Senators. Passionate about education, economic empowerment, and digital innovation, Alfred creates ecosystems that drive inclusive growth. He is a recipient of the Public Policy Forum's 2025 Emerging Leader Award and a Globe & Mail Changemaker.