Financial Performance - The company generated $381.987 million in residential mortgage loans for the three months ended November 30, 2023, a decrease of $4.791 million or 1.24% compared to $386.778 million in the same period in 2022 [77]. - The net loss for the period was $897,757, compared to a net loss of $762,073 in the same period in 2022, representing an increase in loss of 17.80% [99]. - Adjusted EBITDA for the three months ended November 30, 2023, was a loss of $608,575, a decrease of $91,642 or 16.55% compared to a loss of $516,933 in the same period in 2022 [77]. - Total revenue, net for the three months ended November 30, 2023, was $569,355, a decrease of $322,669 or 36.17% from $892,024 in the same period in 2022 [99]. - Sales revenue decreased by $376,880 or 8.29% to $4,169,428 for the three months ended November 30, 2023, compared to $4,546,308 in the same period in 2022 [99]. - The company’s subscription revenue for the three months ended November 30, 2023, was $183,245, a slight decrease from $187,886 in the same period in 2022 [89]. - Sales revenue decreased from $4,546 million in Q3 2022 to $4,169 million in Q3 2023, representing an 8.29% decrease [100]. - Gross margin decreased to 36.17% in Q3 2023 compared to the same period in 2022, attributed to higher volume by low-margin agents [101]. Expenses - The company reported a commission expense of $3,600,073 for the three months ended November 30, 2023, down from $3,654,284 in the same period in 2022, a decrease of 1.48% [99]. - The company experienced a significant increase in depreciation expenses, which rose by 55.52% to $137,427 for the three months ended November 30, 2023, compared to $88,368 in the same period in 2022 [99]. - Cost of revenue decreased to $3,600 million in Q3 2023 from $3,654 million in Q3 2022, reflecting the decline in revenue [102]. - Selling, general and administrative expenses decreased by $139,574 from $699,724 in Q3 2022 to $560,150 in Q3 2023, a 19.95% decrease [104]. - Advertising and marketing expenses increased to $133,470 in Q3 2023 from $121,567 in Q3 2022, a 9.79% increase due to continued investment [108]. Cash Flow and Investments - Net cash used in operating activities decreased to $1,022,782 in Q3 2023 from $1,159,829 in Q3 2022, a decrease of $137,047 [117]. - As of November 30, 2023, the company's cash balance was $2,341,537, down from $2,381,866 a year earlier [119]. - The company invested $0.267 million in software development for mortgage applications in Q3 2023 [119]. - The company invested in a commercial mortgage firm, MCommercial, representing 5% of the total issued and outstanding shares, enhancing product offerings and service levels [134]. - The company acquired 5% of the total issued and outstanding shares of Mortgage Alliance Corporation, a mortgage brokerage firm, through a share purchase agreement [135]. - The total amount of both investments was recorded at fair value, with any impairment loss recognized in the profit and loss account [136]. Stock and Financial Instruments - The company issued 875,000 shares at $4.00 per share during the IPO, raising $2.732 million after expenses [118]. - Stock-based compensation expense recognized for the three months ended November 30, 2023, was $Nil, compared to $52,904 for the same period in 2022 [141]. - The Chief Financial Officer's stock options, with a fair value of $141,885, were forfeited during the year ended August 31, 2023 [142]. - As of November 30, 2023, the company's financial instruments included cash of $2,341,537 and investments valued at $9,976 [149]. - The company issued 26,250 warrants to underwriters of its initial public offering, with a strike price of $4.00 per warrant [143]. - The company completed a 1-for-3.9 reverse stock split, retroactively adjusting all share numbers and prices in the financial statements [143]. Internal Controls and Compliance - The company is implementing plans to improve internal controls over financial reporting, which currently lack adequate segregation of duties and documentation [144]. - The company conducted an evaluation of its internal control effectiveness, concluding deficiencies in accounting and financial reporting processes [144]. Market Conditions - The company has noted that the mortgage origination market has shrunk significantly due to rising mortgage interest rates and economic uncertainty, impacting demand for mortgage originations [74].

Financial Performance - The company generated $1.399 billion in residential mortgage loans for the year ended August 31, 2023, a decrease of $386 million or 21.63% compared to $1.790 billion in the previous year[144]. - The net loss for the year was $2.874 million, an improvement from the net loss of $3.015 million recorded in the previous year[144]. - Adjusted EBITDA for the year was a loss of $1.239 million, representing a decrease of $0.376 million or 23.26% compared to the previous year's loss of $1.615 million[144]. - Total revenue for the year ended August 31, 2023, was $2.502 million, down from $3.600 million in the previous year, indicating a decline of approximately 30.61%[151]. - Net revenue decreased by 30.51% from $3,600,851 in 2022 to $2,502,264 in 2023[165]. - Gross revenue fell by 19.37% from $20.381 million in 2022 to $16.434 million in 2023, attributed to a decline in real estate transactions[166]. - Gross profit margin decreased from 17.67% in 2022 to 15.23% in 2023 due to increased volume by low-margin agents[167]. - Total expenses decreased by 17.58% from $6,410,911 in 2022 to $5,284,158 in 2023[165]. Mortgage and Real Estate Market - The company's mortgage volume decreased to $1.398 billion in 2023 from $1.785 billion in 2022, reflecting a decline of 21.63%[155]. - The Bank of Canada's prime rate increases have led to a significant shrinkage in the mortgage origination market, impacting demand for mortgage originations[143]. - The number of real estate transactions in Canada decreased by 21.02%, from 558,591 in 2022 to 441,536 in 2023[166]. Revenue Streams - Subscription revenue increased to $736,708 in 2023 from $616,734 in 2022, showing a growth of 19.43%[155]. - The company reported a commission expense of $13.932 million in 2023, down from $16.780 million in 2022, a decrease of 16.96%[155]. - Approximately 40% of deals originated by users utilized the pre-assessment underwriting service, indicating a significant uptake of this offering[159]. Investments and Development - The company invested $1,300,225 in software development for mortgage applications during the year[183]. - Depreciation increased by 72.41% from $255,871 in 2022 to $441,159 in 2023, driven by investments in software development[174]. - The Company invested $36,830 in two mortgage-related firms, representing 5% of the total issued shares of each firm, enhancing its service offerings and revenue potential[199]. Cash Flow and Liquidity - Cash used in operating activities increased to $2,116,105 in 2023 from $1,834,909 in 2022, primarily due to a net loss of $2,809,036[181]. - Cash and cash equivalents decreased from $3,896,839 in 2022 to $720,365 in 2023, a decline of $3,176,474[186]. - The Company reported cash and cash equivalents of $720,365 as of August 31, 2023, a significant decrease from $3,896,839 in the previous year[221]. - The Company has a liquidity risk management strategy to ensure sufficient liquidity to meet obligations, with accounts payable and accrued liabilities totaling $605,318 due within one year[222]. Internal Controls and Compliance - The Company’s internal controls over financial reporting were assessed as lacking adequate segregation of duties and documentation as of August 31, 2023[209]. - The Company has adopted ASC 606 for revenue recognition, ensuring revenue reflects the consideration expected from customers[189]. Other Financial Metrics - Share-based compensation dropped by 95.42% from $723,217 in 2022 to $33,091 in 2023, with no options granted during the year[175]. - The total stock-based compensation expense recognized for vested options was $57,340 for the year ended August 31, 2023[206]. - The Company’s lease obligations total $1,107,961, with $138,372 due within one year[222]. - As of August 31, 2023, the Company’s total assets included cash of $720,365 and investments valued at $10,013[213]. - The Company operates an online platform powered by Salesforce, facilitating efficient deal closures for brokers and agents[191].

As filed with the Securities and Exchange Commission on September 28, 2023 Registration No. 333-268636 UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Amendment No. 6 FORM S-1 REGISTRATION STATEMENT UNDER THE SECURITIES ACT OF 1933 PINEAPPLE FINANCIAL INC. (Exact Name of Registrant as Specified in its Charter) (State or Other Jurisdiction of Incorporation or Organization) (Primary Standard Industrial Classification Code Number) Canada 6199 Not applicable (I.R.S. Employer Identificati ...

As filed with the Securities and Exchange Commission on September 15, 2023 Registration No. 333-268636 UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Amendment No. 5 FORM S-1 REGISTRATION STATEMENT UNDER THE SECURITIES ACT OF 1933 PINEAPPLE FINANCIAL INC. (Exact Name of Registrant as Specified in its Charter) (State or Other Jurisdiction of Incorporation or Organization) (Primary Standard Industrial Classification Code Number) Canada 6199 Not applicable (I.R.S. Employer Identificati ...

As filed with the Securities and Exchange Commission on July 5, 2023 Registration No. 333-268636 UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 (Primary Standard Industrial Classification Code Number) Ontario, Canada 6199 Not applicable (I.R.S. Employer Identification Number) Unit 200, 111 Gordon Baker Road North York, Ontario M2H 3R1 Tel: (416) 669-2046 (Address, including zip code, and telephone number, including area code, of Registrant's principal executive offices) Amendment No ...

As filed with the Securities and Exchange Commission on June 21, 2023 Registration No. 333-268636 UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Amendment No. 3 FORM S-1 REGISTRATION STATEMENT UNDER THE SECURITIES ACT OF 1933 PINEAPPLE FINANCIAL INC. (Exact Name of Registrant as Specified in its Charter) (State or Other Jurisdiction of Incorporation or Organization) (Primary Standard Industrial Classification Code Number) Ontario, Canada 6199 Not applicable (I.R.S. Employer Identifi ...

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Amendment No. 2 FORM S-1 As filed with the Securities and Exchange Commission on May 16, 2023 REGISTRATION STATEMENT UNDER THE SECURITIES ACT OF 1933 Registration No. 333-268636 PINEAPPLE FINANCIAL INC. (Exact Name of Registrant as Specified in its Charter) (State or Other Jurisdiction of Incorporation or Organization) (Primary Standard Industrial Classification Code Number) Ontario, Canada 6199 Not applicable (I.R.S. Employer Identific ...