D. Boral Capital Served as Exclusive Placement Agent to Pineapple Financial, Inc. (NYSE: PAPL) in connection with its $1.0 Million Registered Direct Offering

D. Boral Capital Served as Exclusive Placement Agent to Pineapple Financial, Inc. (NYSE: PAPL) in connection with its $1.0 Million Registered Direct Offering Toronto, Nov. 14, 2024 (GLOBE NEWSWIRE) — Pineapple Financial, Inc. (NYSE: PAPL) (the “Company”), Canada’s tech-focused mortgage brokerage with an integrated network of partner brokerages and agents across the country, today announced the closing of its registered direct offering (the “Offering”) with aggregate gross proceeds to the Company of approximately $1,000,000, prior to deducting fees and other expenses payable by the Company.

The Offering consisted of 1,666,667 common shares and pre-funded warrants. Each common share (or pre-funded warrant in lieu thereof) was sold at a purchase price of $0.60 per share (or $0.5999 per pre-funded warrant after reducing $0.0001 attributable to the exercise price of the pre-funded warrants). D. Boral Capital LLC acted as exclusive placement agent for the offering.

Sichenzia Ross Ference Carmel LLP acted as U.S. legal counsel to Pineapple Financial, Inc.

The proposed offering of the securities described above was offered by the Company pursuant to a “shelf” registration statement on Form S-3 (File No. 333-282629) filed with the Securities and Exchange Commission (SEC) and declared effective by the SEC on October 29, 2024, and the accompanying prospectus contained therein. The offering was made only by means of a prospectus supplement and accompanying prospectus. A final prospectus supplement describing the terms of the public offering was filed with the SEC and forms a part of the effective registration statement.

Copies of the prospectus supplement and the accompanying prospectus relating to this offering may be obtained, when available, on the SEC’s website at http://www.sec.gov or by contacting D. Boral Capital LLC Attention: Syndicate Department, 590 Madison Avenue, 39th Floor, New York, NY 10022, by email at syndicate@dboralcapital.com, or by telephone at (212) 970-5150. This press release shall not constitute an offer to sell or the solicitation of an offer to buy any of the securities described herein, nor shall there be any sale of these securities in any state or jurisdiction in which such offer, solicitation or sale would be unlawful prior to registration or qualification under the securities laws of any such state or jurisdiction.

About Pineapple Financial, Inc.

Pineapple is a leader in the Canadian mortgage industry, breaking the mold by focusing on both the long-term success of agents and brokerages, as well as the overall experience of homeowners. With approximately 600 brokers within the network, Pineapple utilizes cutting-edge cloud-based tools and AI-driven systems to enable its brokers to help Canadians realize their ultimate dream of owning a home. Pineapple is active within the community and is proud to sponsor cancer charities across Canada, improving the lives of fellow Canadians touched by cancer.

Company Profile

D. Boral Capital

Industry: Financial Services

For more information please contact:

Investment Banking

Gaurav Verma
Co-Head of Investment Banking
Direct: +1 (929) 528-0912
gverma@dboralcapital.com

Stephanie Hu
Co-Head, Investment Banking
Direct: +1 (929) 586-0272
swafalosky@dboralcapital.com

Stephen Wafalosky
Associate
Direct: +1 (929) 586-1338
swafalosky@dboralcapital.com

Equity Capital Markets

Philip Wiederlight
Chief Operating Officer
Direct: +1 (929) 625-1539
pwiederlight@dboralcapital.com

Mark Iorio
Director, Equity Capital Markets
Direct: +1 (929) 528-0913
miorio@dboralcapital.com

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Ryan J. Whalen

General Counsel

Ryan J. Whalen has been the General Counsel of D. Boral Capital since January of 2023, previously serving as Deputy General Counsel & Head of Litigation at D. Boral Capital, since November of 2021.

Prior to joining D. Boral Capital, Ryan spent over two decades as a litigator representing clients faced with complex business disputes. His experience includes handling securities litigation, financial disputes, corporate governance/director and officer litigation, breaches of fiduciary duty, fraud, professional malpractice, employment law, and whistle-blower claims. Ryan also has experience in the Financial Services industry representing investment banks, hedge funds, public companies, and investors. Most recently, Ryan was a Partner at Gusrae Kaplan Nusbaum PLLC. Law, and prior to that, he was a Partner at Brown & Whalen, P.C.

Ryan holds his Juris Doctor degree from Fordham University School of Law and his bachelor’s degree from the University of Rhode Island.

David W. Boral

Chief Executive Officer & Founder

David W. Boral is the Chief Executive Officer and Founder of D. Boral Capital.

Prior to D. Boral Capital, David held several leadership positions in the Investment Banking and Capital Markets industry. His 16 years of expertise spans both public and private transactions, including IPOs, Secondaries/Follow-On Offerings, SPACs, PIPEs, Reverse Mergers, M&A, Bankruptcy/Restructurings, Cross Listings, and other private and public offerings, in the US and abroad. Most recently, David was Co-Head of Investment Banking & Managing Director at Aegis Capital Corp, and prior to that, he was a Director of Investment Banking, at Maxim Group.

In addition to his work at D. Boral Capital, David is dedicated to improving the world around him, specifically the lives of children and veterans. He currently serves on the advisory board for Keep a Child Alive, a nonprofit organization that provides healthcare, housing, and other support services to HIV/AIDS-affected communities in Africa and India. Additionally, David serves on the board for Lifeline Humanitarian Organization, which was founded by Princess Katherine, to reduce and relieve the suffering of physically and mentally disabled children, orphans, and the elderly, as well as to improve medical facilities in Serbia. He also partners with St. Jude Children’s Research Hospital, Heroes Among Us, and Project Rousseau, through corporate sponsorships.

David holds a bachelor’s degree in Business Administration from the Lubin School of Business at Pace University.

Stephanie (Mengjie) Hu

Co-Head of Investment Banking

Stephanie (Mengjie) Hu has been the Head of Asia at D. Boral Capital since May of 2023, previously serving as Vice President, Asia Investment Banking at D. Boral Capital, since November of 2021.

Stephanie has over 9 years of Investment Banking and Financial Services experience. She has completed over 100 transactions across a wide range of industries, representing over $3.5 billion in aggregate value, and has participated in multiple product offerings including IPOs, Follow-Ons/Secondaries, PIPEs, Private Placement, Uplistings (Re-IPO), Reverse Mergers, Registered Directs, CMPOs, ATMs, SPACs and M&As. Her focus is primarily on serving the financial needs of Asian emerging growth and middle-market companies in a variety of industries.

Stephanie holds a Master’s degree in Finance from the University of Rochester, and she is bilingual in English and Mandarin.

Gaurav Verma

Co-Head of Investment Banking

Gaurav Verma has been covering the Technology, Media, and Telecom sector for over 10 years, and has executed over 100 billion in transactions encompassing sell-side and buy-side M&A, IPOs, SPACs, equity offerings, converts, high yield and investment-grade financings. Mr. Verma has advised C-Suite executive teams on M&A assignments, business development opportunities, growth strategies, and capital allocation policies.

Prior to joining D. Boral Capital, Gaurav was a Director at Nomura, spearheading TMT coverage efforts, and previously, was a Senior Vice President at Bank of America Merrill Lynch, within their TMT Investment Banking Group.

Gaurav received his MBA in Finance and Entrepreneurship from the NYU Stern School of Business and BS in Computer Science and Economics from Rutgers University.

Jared S. Merlin

Chief Compliance Officer

Jared S. Merlin has been the Chief Compliance Officer at D. Boral Capital since November of 2022.

Prior to joining D. Boral Capital, Jared spent nine years as a Managing Director at Credit Agricole Corporate and Investment Bank, serving as the Chief Compliance Officer and Head of Capital Markets Compliance. Jared has over two decades of Compliance experience, providing regulatory advice and oversight to investment banks and broker dealers. Prior to Jared’s tenure at Credit Agricole, Jared held various positions in the Compliance Departments of Knight Capital Americas LLC, and Brown Brothers Harriman & Co.

Jared holds a bachelor’s degree from Syracuse University and an MBA from the NYU Stern School of Business.

Phil Wiederlight

Chief Operating Officer

Phil Wiederlight has been the Chief Operating Officer since November 2023, previously serving as Head of Syndicate, Equity Capital Markets, at D. Boral Capital, since May of 2023.

Phil has spent 15 years in Financial Services, where he has held multiple leadership positions at GoldenTree Asset Management, Sculptor Capital, and JP Morgan. He has completed numerous Capital Markets transactions, which have accounted for several billions of dollars, and has participated in multiple product offerings including IPOs, Follow-Ons/Secondaries, PIPEs, Private Placements, Uplistings (Re-IPO), Reverse Mergers, Registered Directs, CMPOs, ATMs, and SPACs. His experience also includes Cash and Position Reconciliations, Private Equity Structured Products, Trade Settlements, Crypto Settlements, Account Setups, Expense Management, Risk Reporting, and Fund Accounting. Phil has also managed numerous service provider and third-party relationships, which has helped streamline processes and improve internal efficiencies.

Phil holds a Bachelor’s degree in Business Administration from the Miami Herbert Business School at the University of Miami.

Sharad Agrawal

Chief Technology Officer

Sharad Agrawal has been Chief Technology Officer at D. Boral Capital since May of 2023.

Prior to joining D. Boral Capital, Sharad worked in Private Equity in a technology leadership capacity, to improve infrastructure, cybersecurity, and technology operations. Sharad was also Chief Technology Officer at Redwood Capital Management, and prior to that, was Global Head of Information Technology at Eagle Investment Solutions, where he was responsible for all firmwide technology efforts globally. His duties included helping develop custom applications and strategy, while leading compliance, data, digital, engineering, and cloud initiatives.

Sharad will be pursuing an Executive Education-Chief Technology Officer program at University of Pennsylvania beginning Winter 2024.

Ben Reed

Head of Wealth Management

Ben has over a decade of experience in the retail markets, focusing on emerging growth, small, and middle market companies in biotechnology, healthcare, technology, and energy.

Throughout his career, he has helped raise capital for numerous IPOs, secondary offerings, PIPES, and SPACs. He currently holds his series 7, 24, 63, 65, and Insurance Licenses.

He graduated from Villanova University with a Bachelor of Arts degree in Economics and remains an avid Wildcats fan.