Registration No. 333-___333-259619

UNITED STATES

SECURITIES AND EXCHANGE COMMISSION

Washington,WASHINGTON, D.C. 20549

PRE-EFFECTIVE AMENDMENT NO. 2

TO

FORM S-3

REGISTRATION STATEMENT

UNDER

THE SECURITIES ACT OF 1933

1 Venture,501 Brickell Key Drive, Suite 150300

Irvine, CA 92618Miami, FL 33131

(888) 798-9100

(Address, including zip code, and telephone number, including area code, of registrant’s principal executive offices)

Scott W. Absher

Chief Executive Officer

ShiftPixy, Inc.501 Brickell Key Drive. Suite 300

1 Venture, Suite 150Miami, FL 33131

Irvine, CA 92618

(888) 798-9100

(Name, address, including zip code, and telephone number, including area code, of agent for service)

With a copyCopies to:

Lynne Bolduc

FitzGerald Yap Kreditor LLPIvan K. Blumenthal, Esq.

2 Park Plaza, Suite 850Daniel A. Bagliebter, Esq.

Irvine, CA 92614Mintz, Levin, Cohn, Ferris, Glovsky and Popeo, P.C.

(949) 788-8900666 Third Avenue

New York, New York 10017

Approximate date of commencement of proposed sale to the public: From time to time after this Registration Statement becomes effective.(212) 935-3000

If the only securities being registered on this form are being offered pursuant to dividend or interest reinvestment plans, please check the following box. ¨

If any of the securities being registered on this form are to be offered on a delayed or continuous basis pursuant to Rule 415 under the Securities Act of 1933, other than securities offered only in connection with dividend or interest reinvestment plans, check the following box. x

If this form is filed to register additional securities for an offering pursuant to Rule 462(b) under the Securities Act, please check the following box and list the Securities Act registration statement number of the earlier effective registration statement for the same offering. ¨

If this form is a post-effective amendment filed pursuant to Rule 462(c) under the Securities Act, check the following box and list the Securities Act registration statement number of the earlier effective registration statement for the same offering. ¨

If this Formform is a registration statement pursuant to General Instruction I.D. or a post-effective amendment thereto that shall become effective upon filing with the Commission pursuant to Rule 462(e) under the Securities Act, check the following box. ¨

If this Formform is a post-effective amendment to a registration statement filed pursuant to General Instruction I.D. filed to register additional securities or additional classes of securities pursuant to Rule 413(b) under the Securities Act, check the following box. ¨

Indicate by check mark whether the registrant is a large accelerated filer, an accelerated filer, a non-accelerated filer, a smaller reporting company, or an emerging growth company.  See the definitions of “large accelerated filer,” “accelerated filer,”filer” “smaller reporting company,”company” and “emerging growth company” in Rule 12b-2 of the Exchange Act. (Check one.)

If an emerging growth company, indicate by check mark if the registrant has elected not to use the extended transition period for complying with any new or revised financial accounting standards provided pursuant to Section 13(a)7(a)(2)(B) of the ExchangeSecurities Act. ¨

CALCULATION OF REGISTRATION FEE

Title of Each Class of Securities to be Registered		Amount to be Registered (1)				Proposed Maximum Offering Price Per Share				Proposed Maximum Aggregate Offering Price				Amount of Registration Fee (2)
Common stock, par value $0.0001 per share			36,412,207				1.38				50,248,846			$	6,090
Total			36,412,207								50,248,846			$	6,090

_____________

The registrantRegistrant hereby amends this Registration Statement on such date or dates as may be necessary to delay its effective date until the registrantRegistrant shall file a further amendment which specifically states that this Registration Statement shall thereafter become effective in accordance with Section 8(a) of the Securities Act of 1933 or until thethis Registration Statement shall become effective on such date as the Securities and Exchange Commission, acting pursuant to said Section 8(a), may determine.

2

The information in this prospectus is not complete and may be changed.  A registration statement relating to these securities has been filed with the Securities and Exchange Commission.  The selling shareholders may not sell these securities until the registration statement filed with the Securities and Exchange Commission isdeclares the registration statement effective.  This prospectus is not an offer to sell nor does it seekthese securities and is not soliciting an offer to buy these securities in any jurisdictionstate where the offer or sale is not permitted.

Subject to Completion Dated April 1, 2019

ShiftPixy, Inc.

36,412,207SUBJECT TO COMPLETION, DATED JANUARY 14, 2022

PROSPECTUS

15,423,200 Shares of Common Stock

30,645,161 Shares Issuable upon the Repayment and/or Conversion of Senior Convertible Notes

5,767,046 Shares Issuable upon Exercise of Outstanding Warrants

This prospectus relates to the resale, from time to time, by theThe selling shareholders identified inof ShiftPixy, Inc. (“ShiftPixy,” “we,” “us” or the “Company”) listed beginning on page 18 of this prospectus may offer and resell under the caption “Selling Shareholders,” ofthis prospectus (i) up to 36,412,2072,850,000 shares of our common stock, par value $0.0001 per share (the “Common Stock”), 30,645,161and (ii) up to 12,573,200 shares of which are issuable upon the repayment and/or conversion of Senior Convertible Notes (the “Notes”), and 5,767,046 shares of which are issuable upon exercise of certain outstanding common stock purchase warrants (the “Warrants”), all issued by us to the selling shareholders on March 12, 2019.

We are not selling any shares of Common Stock under this prospectus and will not receive any proceeds from the sale of shares of Common Stock by the selling shareholders. We will not receive any proceeds from the repayment and/or conversion of the Notes. We will not receive proceeds from the 85,228 shares ofour Common Stock issuable upon exercise of Warrants on a cashless basis. warrants, including pre-funded warrants and warrants issued by the Registrant to A.G.P./Alliance Global Partners and its affiliates for compensation as placement agent in connection with the transactions described herein (collectively, the “Warrants”) acquired by the selling shareholders under the Securities Purchase Agreement (the “Purchase Agreement”), dated August 31, 2021, by and among the Company and the investor listed therein (the “Investor”) and the Placement Agent Agreement, dated August 31, 2021, by and between the Company and A.G.P./Alliance Global Partners (the “Placement Agent Agreement”).

We will receive proceeds from any cash exerciseare registering the resale of the Warrants, which, if exercised in cash with respect to the other 2,840,909 shares of Common Stock that may be acquired undercovered by this prospectus as required by the WarrantsPurchase Agreement and Placement Agent Agreement.  The selling shareholders will receive all of the proceeds from any sales of the shares offered hereby, would result in gross proceeds to us of up to approximately $4,971,000; however, we cannot predict when and in what amounts or if the Warrantshereby.  We will be exercised, and it is possible that the Warrants may expire and never be exercised, in which case we would not receive any of the proceeds, but we will incur expenses in connection with the offering.  To the extent the Warrants are exercised for cash, proceeds.if at all, we will receive the exercise price of the Warrants.

The selling shareholders may sell thethese shares of our Common Stock offered by this prospectus from time to time on terms to be determined at the time of sale through ordinary brokeragepublic or private transactions or through any other means described in this prospectus under the caption “Plan of Distribution.” The shares of Common Stock may be sold at fixed prices, at market prices prevailing at the time of sale at prices related to prevailing market price or at negotiated prices.  The timing and amount of any sale are within the sole discretion of the selling shareholders.  Our registration of the shares of Common Stock covered by this prospectus does not mean that the selling shareholders will offer or sell any of the shares.  For further information regarding the possible methods by which the shares may be distributed, see “Plan of Distribution” beginning on page 22 of this prospectus.

Our Common Stock is listed on the NASDAQThe Nasdaq Capital Market under the symbol “PIXY.” On March 28, 2019, theThe last reported sale price forof our Common Stock as reported on the NASDAQ Capital MarketJanuary 13, 2022 was $1.38$1.05 per share. There is no established public trading market for the Notes or the Warrants, and we do not expect a market to develop. In addition, we do not intend to apply for a listing of the Notes and Warrants on any national securities exchange.

We are an “emerging growth company” as definedInvesting in our Common Stock is highly speculative and involves a significant degree of risk.  Please consider carefully the Jumpstart Our Business Startups Actspecific factors set forth under “Risk Factors” beginning on page 10 of 2012 and, as such, have elected to comply with certain reduced public company reporting requirements for this prospectus and future filings. See “Prospectus Summary -Implications of Being an Emerging Growth Company.”in our filings with the Securities and Exchange Commission.

Investing in our securities involves a high degree of risk. See the section entitled “Risk Factors” appearing on page 15 of this prospectus for a discussion of information that should be considered in connection with an investment in our securities.

Neither the Securities and Exchange Commission nor any other regulatory bodystate securities commission has approved or disapproved of these securities or passed upon the accuracy or adequacy of the disclosures in this prospectus.  Any representation to the contrary is a criminal offense.

The date of this prospectus is            April 1, 2019., 2022

TABLE OF CONTENTS

ShiftPixy, Inc., and our consolidated subsidiary, Shift Human Capital Management Inc., are referred to collectively herein as “ShiftPixy,” “we,” “us” and “our,” unless the context indicates otherwise.

ABOUT THIS PROSPECTUS

This prospectus is part of a registration statement that we have filed with the U.S. Securities and Exchange Commission (the “SEC”) pursuant to which the selling shareholders named herein may, from time to time, offer and sell or otherwise dispose of the shares of our Common Stock covered by this prospectus.  You may rely only onshould not assume that the information contained in this prospectus is accurate on any date subsequent to the date set forth on the front cover of this prospectus or that any information we have incorporated by reference is correct on any date subsequent to the date of the document incorporated by reference, even though this prospectus is delivered or shares of Common Stock are sold or otherwise disposed of on a later date.  It is important for you to read and consider all information contained in this prospectus, including the documents incorporated by reference therein, in making your investment decision.  You should also read and consider the information in the documents to which we have referred you to. under “Where You Can Find Additional Information” and “Information Incorporated by Reference” in this prospectus.

We have not authorized anyone to providegive any information or to make any representation to you with different information.other than those contained or incorporated by reference in this prospectus.  You must not rely upon any information or representation not contained or incorporated by reference in this prospectus.  This prospectus does not constitute an offer to sell or athe solicitation of an offer to buy any securitiesof our shares of Common Stock other than the securities offered byshares of our Common Stock covered hereby, nor does this prospectus. This prospectus and any future prospectus supplement do not constitute an offer to sell or athe solicitation of an offer to buy any securities in any circumstances in whichjurisdiction to any person to whom it is unlawful to make such offer or solicitation is unlawful. Neither the deliveryin such jurisdiction.  Persons who come into possession of this prospectus orin jurisdictions outside the United States are required to inform themselves about, and to observe, any prospectus supplement nor any sale made hereunder shall, under any circumstances, create any implication that there has been no change in our affairs sincerestrictions as to the dateoffering and the distribution of this prospectus applicable to those jurisdictions.

Unless we have indicated otherwise, or such prospectus supplement or that the information contained by reference tocontext otherwise requires, references in this prospectus or any prospectus supplement is correct as of any time after its date.to “ShiftPixy,” the “Company,” “we,” “us” and “our” refer to ShiftPixy, Inc.

4

Table of Contents

9

Table of Contents

The Challenges of Staffing: Employers have difficulty filling open positions for shift work, and shifters have difficulty in securing shift work at times and dates they are available for such shift work.

The Challenges of Compliance: Employment law compliance requirements, including those related to the ACA, present a multi-obstacle ridden employment related compliance landscape, including the need to secure applicable workers’ compensation insurance coverage, to effect employment related tax withholdings and filings, and to navigate laws related to hiring and release of employees, including discrimination (race, color, national origin, sex, age, religion, disability, pregnancy and sexual orientation), sexual harassment, sick pay and time off, hours of work, minimum wage and overtime, gender pay differentials, immigration, safety, child labor, military leave, garnishment and other wage imposition processing, family and medical leave, COBRA, and unemployment claims.

A business can secure assistance in mitigating and even eliminating these challenges by contracting with us.

The ShiftPixy Solution: We are developing an ecosystem comprised of a closed proprietary operating and processing system that helps restaurant or hospitality businesses (and in the future, businesses in additional industries wherein we plan to market our services) as well as shift workers by matching available shifts with available shift workers. The ShiftPixy Ecosystem will provide the following benefits:

Shift Human Capital Management Inc.: We formed Shift Human Capital Management Inc., a wholly­owned subsidiary (which we refer to as “ShiftableHR”), in December 2015, in response to the need to have workers’ compensation policies written in the names of our clients (as may be required by some states) and otherwise in response to client needs for only administrative and processing services rather than the full­service, staffing program we offer. As of November 30, 2018, ShiftableHR had 122 clients with 5,400 worksite employees, including 2,560 employees for whom we provide only payroll administration services.

10

Table of Contents

Significant Developments in 2019

Office Update

Our headquarters are currently located in Irvine, California, from which we can reach the Southern California market. We recently opened offices in Austin, Texas; Orlando, Florida; New York City, New York and Chicago, Illinois from which our local sales/services representatives can secure and service clients in those areas. We are currently focused on clients in the restaurant and hospitality industries. California continues to be our largest market and accounts for approximately 82% of our gross billings. Texas continues to be our second largest market at about 6%. The other locations have not yet impacted our revenue in a meaningful way. Of note, we have onboarded during the second quarter of 2019 large franchisees of national brands in the State of Washington and the Commonwealth of Pennsylvania, and these states now account for approximately 7%, combined, of our gross billings.

Software Development

               The heart of our employment service solutions is a technology platform, including a mobile app, through which our employees (and in the future, shifters not currently in our Ecosystem) will be able to find available shifts at our client locations, solving a problem of finding available shifts for both the shifters looking for additional shifts and businesses looking to fill open shifts. 

THE OFFERING

Throughout this prospectus, when we refer to the shares of our Common Stock being registered on behalf of the selling shareholders for offer and sale, we are referring to the shares of Common Stock sold to the selling shareholders, as well as the shares of Common Stock issuable upon exercise of the Warrants, each as described under “The Offering” and “Selling Shareholders.” When we refer to the selling shareholders in this prospectus, we are referring to the selling shareholders identified in this prospectus and, as applicable, their donees, pledgees, transferees or other successors-in-interest selling shares of Common Stock or interests in shares of Common Stock received after the date of this prospectus from a selling shareholder as a gift, pledge, partnership distribution or other transfer.

RISK FACTORS

Investing in our securities involves a high degree of risk.  You should carefully consider and evaluate all of the information contained in this prospectus and in the documents we incorporate by reference into this prospectus before you decide to purchase our securities.  In particular, you should carefully consider and evaluate the risks and uncertainties described below and under the heading “Risk Factors” in the Annual Report.  Any of the risks and uncertainties set forth below and in the Annual Report, as updated by annual, quarterly and other reports and documents that we file with the SEC and incorporate by reference into this prospectus, or any prospectus, could materially and adversely affect our business, results of operations and financial condition, which in turn could materially and adversely affect the value of any securities offered by this prospectus.  As a result, you could lose all or part of your investment.

Risks Relating to Our Business

There is no guarantee that our current cash position, expected revenue growth and anticipated financing transactions will be sufficient to fund our operations for the next twelve months. Our sponsorship of various SPACs requires significant capital deployment, entails certain risks and may not be successful, which would likely have a material adverse effect on our future expansion, revenues, and profits.

As of August 31, 2021, we had cash of $1.5 million and a working capital deficit of $10.9 million. We have incurred recurring losses, which has resulted in an accumulated deficit of $149.4 million as of August 31, 2021. The recurring losses and cash used in operations are indicators of substantial doubt as to our ability to continue as a going concern for at least one year from issuance of the audited financial statements incorporated in our Annual Report on Form 10-K for the fiscal year ended August 31, 2021. Our plans to alleviate substantial doubt are discussed below and elsewhere in our Annual Report on Form 10-K for the fiscal year ended August 31, 2021.

Historically, our principal source of financing has come through the sale of our common stock and issuance of convertible notes. In May 2020, we successfully completed an underwritten public offering, raising a total of $12 million ($10.3 million net of costs), and closed an additional $1.35 million ($1.24 million net of costs) between June 1, 2020 and July 7, 2020 pursuant to the underwriter’s overallotment. In October 2020, we closed an additional $12 million equity offering ($10.7 million net of costs). In May 2021, we raised approximately $12 million ($11.1 million net of costs) in connection with the sale of common stock and warrants. More recently, in September 2021, we raised approximately $12 million ($11.1 million net of costs) in connection with the sale of common stock and warrants. Our plans and expectations for the next twelve months include raising additional capital to help fund expansion of our operations, including the continued development and support of our IT and HRIS platform, as well as our activities in connection with our sponsorship of the SPACs described above. We expect to continue to invest in our HRIS platform, ShiftPixy Labs, our sponsorship of the SPACs and other growth initiatives, all of which have required and will continue to require significant cash expenditures.

We do not currently have financing plans but we expect to obtain additional financing in the form of public or private equity offerings over the next twelve months as described above to purchase private placement warrants and to extend loans in connection with the SPAC IPOs of Vital, TechStackery and Firemark and to extend loans to IHC in connection with its IBC.  We are not in a position to state with certainty if or when any of the SPAC IPOs of Vital, TechStackery and Firemark will be consummated, or the terms upon which such SPAC IPOs ultimately will be completed. There is no assurance that IHC will be able to consummate its IBC within twelve months from the closing of the IHC IPO or that each of Vital, TechStackery and Firemark will be able to complete their respective IBCs within twelve months from the closing of their respective IPOs, in which case such SPACs would cease all operations except for the purpose of winding up. While we believe that all of the SPACs, after completing their IBCs, will generate significant revenues for us by virtue of entering into CSAs and/or other contractual relationships with us after completing the De-SPAC process, we are unable to rely with certainty on the SPACs to generate revenue in the future.

Assuming that each of Vital, TechStackery and Firemark consummate their SPAC IPOs for gross proceeds of $100 million, we expect to invest, through Investments, an aggregate of $12,792,306 (or up to $13,917,306 if the over-allotment option of each of Vital, TechStackery and Firemark is exercised in full) in such SPACs to purchase private placement warrants. As previously disclosed, on October 22, 2021, we invested an aggregate of $4,639,102 to purchase private placement warrants in IHC through Investments. Also, as previously disclosed, on February 18, 2021, we invested an aggregate of $100,000 to purchase founder shares in all four of our sponsored SPACs through Investments. We will lose our entire investment in each of Vital, TechStackery and Firemark if such SPACs are unable to complete their IPOs successfully. Furthermore, the combined value of our equity investment in our sponsored SPACs, as carried on the consolidated balance sheet included in the financial statements accompanying our Annual Report on Form 10-K, filed with the SEC on December 3, 2021, is $47,472,000, which we have computed in accordance with accounting principles generally accepted in the United States, and which constitutes the majority of the carrying value of our total assets as reflected on our consolidated balance sheet. If all of the SPACs are unable to consummate their IBCs, then our founder shares and private placement warrants in each SPAC will be worthless. Further, even if all of the SPACs are able to consummate their respective IBCs, we can provide no assurance that the value of this equity investment will not decline significantly based upon a variety of factors, including, without limitation, stockholder and general market reaction to any IBC, redemption requests received from SPAC stockholders in connection with any proposed IBC, and SPAC stockholder dilution resulting from additional capital raises or other financing transactions undertaken by the SPACs in connection with any IBC.

We expect our investment in our HRIS platform to continue over the next twelve months regardless of whether we enter into client services agreements with the SPACs, and regardless of whether our SPACs are able to complete successfully the De-SPAC process, as we believe such investments will be necessary to support our existing clients as well as our future organic growth. While we anticipate that these investments will yield benefits to us in the future in the form of increased revenues and earnings, it is likely that such improved financial results will be delayed or otherwise materially impacted if we are unable to enter successfully into client services agreements with the SPACs on terms that are beneficial to us, or if the SPACs are unable to complete the De-SPAC process, including the IBCs.

We believe that our current cash position, along with our cost controls, projected revenue growth and theanticipated financing from potential institutional investors, will be sufficient to alleviate substantial doubt and fund our operationoperations for at least a year from the next 12 months.date of this Form 10-K. If these sources do not provide the capital necessary to fund our operations,during the next twelve months, we may need to curtail certain aspects of our operations or expansion activities, consider the sale of itsadditional assets, or consider other means of financing. We can give no assurance that we will be successful in implementing our business plan and obtaining financing on terms that are advantageous to us, or that any such additional financing wouldwill be available to us.available.

We will lose our entire investment in each SPAC if each SPAC does not complete its initial business combination and our officers may have warrants and convertible debt that may be converted into shares issueda conflict of interest in the future, which would dilute your ownership in us.determining whether a particular business combination target is appropriate for each SPAC.

On April 29, 2021, we announced our sponsorship, through Investments, of four SPAC IPOs. We purchased founder shares in each SPAC, through Investments, for an aggregate purchase price of $100,000, or $25,000 per SPAC. The June Notesnumber of founder shares issued to us was determined based on the expectation that such founder shares would represent 15% of the outstanding shares of each SPAC after its initial public offering (excluding the private placement warrants described below and their underlying securities). We are likely to be able to make a substantial profit on our nominal investment in the founder shares even at a time when each SPAC’s public shares have lost significant value. On the other hand, the founder shares will be worthless for each SPAC that does not complete an IBC. Accordingly, Investments will benefit from the completion of IBCs and may be converted, at the optionincentivized to complete an IBC of the holders at an initial conversion price of $2.49, subjecta less favorable target company or on terms less favorable to adjustment from down round price protection. However, from and after the maturity date, the conversion price should be the lesser of (a) the initial conversion price of $2.49, subject to adjustment from down round price protection and (b) a 15% discount to the lowest volume weighted average price. The June Warrants may be exercised any time after December 4, 2018 (initial exercise date), until December 4, 2023 (termination date).stockholders rather than liquidate.

The December Notes may be converted,registration statement and prospectus relating to the IPO of one of our sponsored SPACs, IHC, was declared effective by the SEC on October 19, 2021, and IHC units (the “IHC Units”), consisting of one share of common stock and an accompanying warrant to purchase one share of IHC common stock, began trading on the NYSE on October 20, 2021. The IHC IPO closed on October 22, 2021, raising gross proceeds for IHC of $115 million. In connection with the IHC IPO, we purchased, through our wholly-owned subsidiary, 4,639,102 placement warrants at a price of $1.00 per warrant, for an aggregate purchase price of $4,639,102. Assuming that each of Vital, TechStackery and Firemark consummate their initial public offerings for gross proceeds of $100 million, we expect to invest, through Investments, an aggregate of $12,792,306 (or up to $13,917,306 if the over-allotment option of the holderseach of Vital, TechStackery and Firemark is exercised in full) in such SPACs to purchase private placement warrants. As previously disclosed, on October 22, 2021, we invested an aggregate of $4,639,102 to purchase private placement warrants in IHC through Investments. Also, as previously disclosed, on February 18, 2021, we invested an aggregate of $100,000 to purchase founder shares in all four of our sponsored SPACs through Investments. Each whole private placement warrant is exercisable to purchase one whole share of common stock in each SPAC at $11.50 per share. The private placement warrants of each SPAC will also be worthless if each SPAC does not complete an initial conversion price of $2.49, subject to adjustment from down round price protection. However, from and after the maturity date, the conversion price should be the lesser of (a) the initial conversion price of $2.49, subject to adjustment from down round price protection and (b) a 15% discount to the lowest volume weighted average price.IBC.

The March Notes may be converted at a conversion price of $1.67 per share andinvestment amounts set forth above do not include loans that Investments extended to each SPAC in the March Warrants are exercisable at $1.75 per share.

If the price per share of our common stock at the time of exercise of any June Warrants or March Warrants or conversion of any June Notes, December Notes, or March Notes is in excess of the various exercise or conversion prices of such convertible securities, exercise or conversion of such convertible securities would have a dilutive effect on our common stock.

Further, any additional financing that we secure may require the granting of rights, preferences or privileges senior to those of our common stock and which result in additional dilution of the existing ownership of our common shareholders.

The June Notes contain a mandatory default amount when an event of default occurs

The June Notes contain a mandatory default amount when an event of default occurs. The June Notes define the mandatory default amount as the sum of (a) the greater of (i) the outstanding principal amount of $500,000 (or $2 million in the June Note, plus accruedaggregate), in our role as sponsor (through Investments), to cover initial public offering-related and unpaid interestorganizational expenses of each SPAC, concluding SEC registration, legal and make whole, divided by the conversion price on the date the mandatory default amount is either (x) demanded or otherwise due or (y) paid in full, whichever has a lower conversion price, multiplied by the highest weighted average price for the common stock on the trading market during the period beginning onauditing fees. As of the date of first occurrencethis prospectus, Investments has been fully repaid by IHC and an aggregate of $550,000 remains outstanding to Vital, TechStackery and Firemark. To the eventextent each of defaultVital, TechStackery and ending on the date the mandatory default amount is demanded or otherwise due or paid in full, or (ii) 130% of the outstanding principal amount of the June Note plus 100% of accrued and unpaid interest and make whole and other costs, expenses and liquidated damages due in respect of the June Notes. The make whole amount is defined as the initial 12-month interest amount. Liquidated damagesFiremark do not complete their respective IPOs, such loans are calculated as the product of 2% by the aggregate subscription amount paid by each holder. If we failunlikely to pay any partial liquidated damages in full within seven days after the date payable, we will pay interest thereon at a rate of 18% per annum accruing daily

If any event of default occurs, the outstanding principal amount of the June Notes, plus accrued interest but unpaid interest, liquidated damages and other amounts owing in respect thereof through the date of acceleration, should become, at the holder’s election, immediately due and payable in cash at the mandatory default amount. Commencing five days after the occurrence of any event of default that results in the eventual acceleration of the June Notes, the interest rate on the June Notes shall accrue at 18% daily.

Our ability to adjust and collect service fees for increases in unemployment tax rates may be limited.

We record our State Unemployment Tax (“SUI”) expense based on taxable wages and tax rates assigned by each state. SUI tax rates vary by state and are determined, in part, based on prior years’ compensation experience in each state. Prior to the receipt of final tax rate notices, we estimate our expected SUI tax rate in those states for which tax rate notices have not yet been received for purposes of pricing. In a period of adverse economic conditions state unemployment funds may experience a significant increase in the number of unemployment claims. Accordingly, SUI tax rates would likely increase substantially. Some states have the ability under law to increase SUI tax rates retroactively to cover deficiencies in the unemployment fund.repaid.

In addition, FUTAwe may extend working capital loans to IHC to finance transaction costs in connection with IHC’s IBC. To date, we have not extended any such working capital loans, nor have we determined the terms upon which any such working capital loans would be extended and/or repaid. Up to $1,500,000 of such working capital loans may be retroactively increased in certain states in the event the state failsconvertible into private placement warrants of IHC’s post business combination entity, at a price of $1.00 per warrant at our option. If we extend working capital loans to timely repay federal unemployment loans. Employers inIHC and IHC does not consummate its IBC, such statesworking capital loans are experiencing higher FUTA tax rates as a result of not repaying their unemployment loans from the federal government in a timely manner. The credit reduction is an additional tax on the FUTA wage base for employers in states that continueunlikely to have outstanding federal unemployment insurance loans beginning with the fifth year in which there is a balance due on the loan. States have the option to apply for a waiver before July 1st of the year in which the credit reduction is applicable.

21

Table of Contents

Generally, our contractual agreements allow us to incorporate such statutory tax increases into our service fees upon the effective date of the rate change. However, our ability to fully adjust service fees in our billing systems and collect such increases over the remaining term of the clients’ contracts could be limited, resulting in a potential tax increase not being fully recovered. As a result, such increases could have a material adverse effect on our financial condition or results of operations.

We have claims and lawsuits against us that may result in adverse outcomes.repaid.

We are subjectdo not currently have financing plans but we expect to a variety of claims and lawsuits. These claims may arise from a wide variety of business practices, significant business transactions, operational claims, and employment practices. Adverse outcomes in some or all of these claims may result in significant monetary damages or injunctive relief that could adversely affect our ability to conduct our business. The litigation and other claims are subject to inherent uncertainties and management’s view of these matters may changeobtain additional financing in the future. A material adverse impact on our consolidated financial statements could occur forform of public or private equity offerings over the periodnext twelve months as described above to purchase private placement warrants and to extend loans in whichconnection with the effectSPAC IPOs of an unfavorable outcome becomes probableVital, TechStackery and reasonably estimable.Firemark and to extend loans to IHC in connection with its IBC.

Our failure to implement and maintain effective internal control over financial reporting could result in material misstatements in our financial statements, which could require us to restate financial statements, cause investors to lose confidence in our reported financial information and could have an adverse effect on our stock price or our debt ratings.

Our management conducted an evaluation of the effectivenessThe interests of our internal controls over financial reportingofficers who also serve as officers of November 30, 2018. In making this evaluation, management used the criteria set forth by the Committee of Sponsoring Organizations of the Treadway Commission (“COSO”) in its 2013 Internal Control — Integrated Framework. Based on this evaluationeach SPAC, and because of the material weakness described below,Mr. Absher, our Chairman and Chief Executive Officer and Chief Financial Officer have concluded that our internal controls over financial reporting were not effectivewho also serves as Chairman of the endBoard of November 30, 2018. Our management undertook several remediation actions, including additional segregationDirectors of duties within our accountingeach SPAC, may influence their motivation in identifying and financial reporting functions,selecting a target business combination, completing an expansioninitial business combination and influencing the operation of our corporate accounting staff and the additionbusiness following the initial business combination of qualified personnel with knowledge of U.S. GAAP to help address the material weaknesses identified at November 30, 2018. These measures should improve our internal controls and remediate lack of segregation of incompatible duties that was identified as material weakness at November 30, 2018.each SPAC.

The other deficiencies in controls we identified as of November 30, 2018, which were (i) lack of sufficient finance and accounting personnel with the relative U.S. GAAP knowledge, and (ii) lack of effective financial reporting process to prepare financial statements in accordance with U.S. GAAP still existed at November 30, 2018.

Additional material weaknesses in our internal control over financial reporting may be identified in the future. Any failure to maintain existing or implement required new or improved controls, or any difficulties we encounter in their implementation, or in remediating identified weakness, could result in additional control deficiencies, cause us to fail to meet our periodic reporting obligations or result in material misstatements in our financial statements. The existence of a material weakness could result in errors in our financial statementsThere is no assurance that could result in a restatement of financial statements and cause us to fail to meet our reporting obligations. If we are unable to effectively remediate material weaknesses in a timely manner, investors could lose confidence in the accuracy and completeness of our financial reports, which could have an adverse effect on our stock price.

Technology Oriented Risks

If we are unable to protect our proprietary and technology rights our operationsIHC will be adversely affected.

Our success will depend in part on our abilityable to protect our proprietary rights and technologies, including those related to our products and services. Protecting our intellectual property rights and combating unlicensed copying and use of our software and other intellectual property is difficult. Except as otherwise noted herein, we have not applied for any formal patent, trademark or similar protection. Our failure to adequately protect our proprietary rights may adversely affect our operations. Despite our efforts to protect our proprietary rights, unauthorized parties may attempt to copy aspects of our services or to obtain and use trade secrets or other information that we regard as proprietary. Based oncomplete its IBC within the nature of our business, we may ornext twelve months. Additionally, the remaining SPACs may not be able to adequately protect our rights through patent, copyright and trademark laws. Our meanscomplete their IBCs within twelve months from the closing of protecting our proprietary rightstheir respective SPAC IPOs, in which case the SPACs would cease all operations except for the purpose of winding up. While we believe that the SPACs, after completing their IBCs, will generate significant revenues for us by virtue of entering into CSAs and/or other contractual relationships with us after completing the De-SPAC process, we are unable to rely with certainty on the SPACs to generate revenue in the United States or abroad may notfuture.

We expect our investment in our HRIS platform to continue over the next twelve months regardless of whether we enter into CSAs with the SPACs, and regardless of whether our SPACs are able to complete successfully the De-SPAC process, as we believe such investments will be adequate, and competitors may independently develop similar technologies. In addition, litigation may be necessary to support our existing clients as well as our future organic growth. While we anticipate that these investments will yield benefits to us in the future to:

Anyin the form of increased revenues and earnings, it is likely that such litigation could result in substantial costsimproved financial results will be delayed or otherwise materially impacted if we are heldunable to have willfully infringedenter successfully into CSAs with the SPACs on terms that are beneficial to us, or if the SPACs are unable to expend significant resources to develop non-infringing technology and would divertcomplete the attention of management from the implementationDe-SPAC process, including their IBCs.

Certain of our business strategy. Furthermore, the outcomeofficers and directors have potential conflicts of litigation is inherently difficult to predict and we may not prevail in any litigation in which we become involved.

22

Table of Contents

Software products we use ininterest arising from our business may contain defects which will make it more difficult for us to establish and maintain customers.

We are currently using PrismHR software for our payroll processing. We also use MasterTax to process our tax reports and filings. We also use a host of other software products in the course of conducting our business. The mobile app component of our mobile platform, along with our client portal and the ShiftPixy Command Hub, constitute our proprietary software and contain components that are licensed from third parties and that are public domain software. Our payroll processing software and other software products we use in our business may contain undetected design faults and software errors, or “bugs” that are discovered only after they has been installed and used by a greater number of customers. Any such defect or error in new or existing software or applications could cause delays in delivering our technology or require design modifications. These could adversely affect our competitive position and cause us to lose potential customers or opportunities. Since our technologies are intended to be utilized to supply human resources related services, the effect of any such bugs or delays will likely have a detrimental impact on us. In addition, given that our specialized human resources software and services has yet to gain widespread acceptance in the market, any delays or other problems caused by software bugs would likely have a more detrimental impact on our business than if we were a more established company.

If a contract relating to our mission critical software that we use in our business is terminated or not renewed, our business could be seriously disrupted and our revenues significantly reduced.

If a contract relating to our mission-critical software services, such as that applicable to payroll and payroll tax processing, is terminated or non-renewed, and we do not have an effective replacement software, our business and revenues would suffer. Although there are other software vendors we can use, it may take time to negotiate an agreement and make operational this replacement software. Accordingly, if the software agreements that we use in our business are terminated or not renewed, our business could be seriously disrupted and our revenues significantly reduced until we locate and make operational replacement software.

Our systems may be subject to disruptions that could have a materially adverse effect on our business and reputation.SPAC sponsorship activities.

Our business isofficers may not commit their full time to our affairs, which may result in a conflict of interest in allocating their time between our operations and will continuethe SPACs.  All of our officers are engaged in the SPACs and our officers are not obligated to be highly dependent on our ability to process, on a daily basis, a largecontribute any specific number of complicated transactions. We rely heavily on our payroll, financial, accounting, and other data processing systems. We may not be successful in preventing the loss of client data, service interruptions or disruptionshours per week to our operations from system failures. If any of these systems fails to operate properly or becomes disabled even for a brief period of time, we could suffer financial loss, a disruptionaffairs. All of our businesses, liability to clients, regulatory intervention, or damage toofficers serve as officers of each SPAC and Mr. Absher, our reputation, anyChairman and Chief Executive Officer, also serves as Chairman of which could have a materially adverse effect on our resultsthe Board of operation or financial condition.

Because we store data in the cloud with providers such as Microsoft and Amazon, any disruptions in our ability to access this data or any breachDirectors of security concerning this data in the cloud could have a materially adverse effect on our business and reputation.

Our business is and will continue to be highly dependent on data storage in the cloud with providers such as Microsoft and Amazon. These cloud storage systems may fail to operate properly or become disabled even for a brief period of time. There could also be security breaches of our data stored in the cloud. If there is loss of client data, service interruptions or disruptions to our operations related to our cloud data storage, we could suffer financial loss, a disruption of our businesses, liability to clients, regulatory intervention, or damage to our reputation, any of which could have a materially adverse effect on our results of operation or financial condition.

23

Table of Contents

We make significant investments in our software that may not achieve our expectations.

Developing new technologies is complex. It can require long development and testing periods. Significant delays in new releases or significant problems in creating new products or services could adversely affect our revenue.

Third parties may claim we infringe their intellectual property rights.

From time to time, others claim we infringe their intellectual property rights. The number of these claims may grow because of constant technological change in the markets in which we compete, the extensive patent coverage of existing technologies and the rapid rate of issuance of new patents. To resolve these claims, we may enter into royalty and licensing agreements on terms that are less favorable than currently available, stop selling or redesign affected products or services, or pay damages to satisfy indemnification commitments with our customers. These outcomes may cause operating margins to decline. Besides money damages, in some jurisdictions plaintiffs can seek injunctive relief that may limit or prevent importing, marketing, and selling our products or services that have infringing technologies.

We may not be able to protect our source code from copying if there is an unauthorized disclosure of source code.

Source code, the detailed program commands for our operating systems and other software programs, is critical to our business. We take significant measures to protect the secrecy of large portions of our source code. If a significant portion of our source code leaks, we might lose future trade secret protection for that source code. It may become easier for third parties to compete with our products by copying functionality, which could adversely affect our revenue and operating margins. Unauthorized disclosure of source code also could increase the security risks described in the next paragraph.

We may have outages, data losses, and disruptions of our online services if we fail to maintain an adequate operations infrastructure.

Our increasing user traffic, growth in services, and the complexity of our services demand more computing power. We spend substantial amounts to build, purchase, or lease datacenters and equipment and to upgrade our technology and network infrastructure to handle more data. These demands continue to increase as we grow our workforce. Maintaining, securing, and expanding this infrastructure is expensive and complex. It requires that we maintain an Internet connectivity infrastructure that is robust and reliable within competitive and regulatory constraints that continue to evolve. Inefficiencies or operational failures, including temporary or permanent loss of customer data or insufficient Internet connectivity, could diminish the quality of our products, services, and user experience resulting in contractual liability, claims by users and other third parties, regulatory actions, damage to our reputation, and loss of current and potential users, subscribers, and advertisers, each of which may harm our operating results and financial condition.

Our software may experience quality or supply problems.

Our software may experience quality or reliability problems. The highly-sophisticated software we have been developing may contain bugs and other defects that interfere with their intended operation. Any defectsSPAC. While we do not detect and fix in pre-release testing could cause reduced sales and revenue, damagebelieve that the time devoted to the SPACs will undermine their ability to fulfill their duties with respect to our reputation, repair or remediation costs, delays inCompany, if the releasebusiness affairs of new products or versions, or legal liability. Although our license agreements typically contain provisions that eliminate oreach SPAC require them to devote substantial amounts of time to such affairs, it could limit our exposure to liability, there is no assurance these provisions will withstand legal challenge.

We intend to use open source blockchain technology in its technology platform. This technology has been scrutinized by regulatory agencies and therefore we may be impacted by unfavorable regulatory action in one or more jurisdictions.

The Company intends to use open source blockchain technology as a secure repository for “device reputation” information acquired by its technology platform. Blockchain technologies have been the subject of scrutiny by various regulatory bodies around the world. We could be impacted by one or more regulatory inquiries or actions, including but not limited to restrictions on the use of blockchain technology, which could impede or limit the use of this technology within our product offerings.

We intend to use and leverage open source technology in our technology platform which may create risks of security weaknesses.

Some parts of our technology may be based on open-source technology, including the blockchain technology that we intend to use in our technology platform. There is a risk that the development team, or other third parties may intentionally or unintentionally introduce weaknesses or bugs into the core infrastructure elements of our technology solutions interfering with the use of such technology or causing loss to us.

The use of new and untested technologies, including blockchain technology, may result in risks that we may not be able to currently anticipate.

Blockchain technology is a relatively new and untested technology. In addition to the risks set forth here, there are risks with the use of this technology that we cannot anticipate. Risks may further materialize as unanticipated combinations or variations from the risks set forth here.

24

Table of Contents

Risks Related to Management and Personnel

We depend heavily on Scott W. Absher, our Chief Executive Officer and a director. The loss of his services could harm our business.

Our future business and results of operations depend in significant part upon the continued contributions Scott W. Absher, our Chief Executive Officer and a director. If we lose his services or if he fails to perform in his current position, or if we are not able to attract and retain skilled employees in addition to Mr. Absher, this could adversely affect the development of our business plan and harm our business.

Mr. Absher has limited experience managing a public company, which may inhibit ourtheir ability to implement successfully our business plan.

Mr. Absher is the beneficial owner of approximately 41.9% of our Common Stock as of November 30, 2018, has limited experience managing a public company, which is required to establish and maintain disclosure controls and procedures and internal control over financial reporting. We are endeavoring to comply with all of the various rules and regulations, which are required for a public company that is reporting company with the SEC. However, if we cannot operate successfully as a public company, your investment may be materially adversely affected.

Our business depends on our ability to attract and retain talented employees.

Our business is based on successfully attracting and retaining talented employees. The market for highly skilled workers and leaders in our industry is extremely competitive. If we are less successful in our recruiting efforts, or if we cannot retain key employees, our ability to develop and deliver services successfully may be adversely affected. Effective succession planning is also importantdevote time to our long-term success. Failure to ensure effective transfer of knowledge and smooth transitions involving key employees could hinder our strategic planning and execution. How employment-related laws are interpreted and applied to our workforce practices may result in increased operating costs and less flexibility in how we meet our workforce needs.

Industry Risks

Providing specialized Gig Economy oriented staffing management products and services is an emerging yet competitive business, and many of our competitors have greater resources that may enable them to compete more effectively.

We will compete in the same markets with many companies that offer not only staffing management products and services focused on the Gig Economy but also more traditional staffing management products and services. There are limited barriers to entry. Price competition in the industry, particularly from larger, more traditional industry model competitors, is intense, and pricing pressures from competitors and clients are increasing. New competitors entering our markets may further increase pricing pressures.

Clients may competitively bid new contracts; a trend is expected to continue for the foreseeable future. Some of our competitors have greater resources than we do,affairs which may enable them to compete more effectively in this market. Our competitors may devote their resources to developing and marketing products and services that will directly compete with our product lines, and new, more efficient competitors may enter the market. If we are unable to successfully compete with existing companies and new entrants to the market this will have a negative impact on our operations. The interests of each of these individuals in our Company and the SPACs may influence their motivation in identifying and selecting a target business combination, completing an initial business combination and financial condition.influencing the operation of our business following the initial business combination of each SPAC.

We operateNone of our officers or directors (i) hold any equity interest in the SPACs, (ii) receive any form of compensation from the SPACs, or (iii) have any pecuniary interest related to the SPACs separate and apart from their pecuniary interest in our Company. While Messrs. Absher, Carney and Gans, as officers and/or directors of both our Company and the SPACs, owe fiduciary duties to each entity, our Board has considered this matter and determined that no disabling conflict of interest has arisen or is likely to arise that would prevent these individuals from discharging their fiduciary duties on behalf of our Company. As a result, our Board has (i) approved our sponsorship of the SPACs through our subsidiary, Investments, (ii) approved Messrs. Absher, Carney and Gans serving as officers and/or directors of the SPACs, and (iii) approved the allocation of additional ShiftPixy resources, including financial backing and personnel, for the purpose of supporting the activities of the SPACs as they pursue their initial business combinations. Further, we do not anticipate that any of the SPACs will enter into an immatureinitial business combination with a target business affiliated with us, Investments, or any of our officers or directors. To the extent one of the SPACs were to propose a business combination with such an affiliated person or related party, such transaction would be negotiated on an arms’ length basis and rapidly evolving industrybe subject to Board and have a relatively new business model, which makes it difficult to evaluate our business and prospects.shareholder approvals, as appropriate.

CAUTIONARY NOTE REGARDING FORWARD-LOOKING STATEMENTS

The industry in which we operate is characterizedThis prospectus and the documents incorporated by rapidly changing regulatory requirements, evolving industry standardsreference into this prospectus include forward-looking statements within the meaning of Section 27A of the Securities Act of 1933 and shifting user and client demands. Our business model is also evolving and is different from models used by other companies in our industry. As a resultSection 21E of these factors, the success and future revenue and income potentialSecurities Exchange Act of our business is uncertain. Any evaluation of our business and our prospects must be considered in light of these risks and uncertainties, some of which1934, as amended, that relate to future events or our ability to:

25

Table of Contents

If we are unable to successfully address the challenges posed by operating in an immature and rapidly evolving industry and having a relatively new business model, our business could suffer.

If we are not recognized as an employer of worksite employees under federal and state regulations, or we are deemed to be an insurance agent or third-party administrator, we and our clients could be adversely impacted.

While through our professional employer organization client engagements with ShiftableHR, we typically arrange for clients to act as sponsor of employee benefit plans, we sponsor the benefit plans applicable to our employees. In order for us to sponsor employee benefit plan offerings for our worksite employees, we must qualify as an employer of our worksite employees for certain purposes under the Code and ERISA. In addition, our status as an employer is important for purposes of ERISA’s preemption of certain state laws. The definition of employer under various laws is not uniform, and under both the Code and ERISA, the term is defined in part by complex multi-factor tests.

26

Table of Contents

Generally, these tests are designed to evaluate whether an individual is an independent contractor or employee and they provide substantial weight to whether a purported employer has the right to direct and control the details of an individual’s work. Some factors that the IRS has considered important in the past have included the employer’s degreemay cause our actual results, levels of behavioral control (the extentactivity, performance or achievements to differ materially from any future results, levels of instructions, training and the nature of the work), the financial control and the economic aspects of the relationship, and the intent of the parties, as evidencedactivity, performance or achievements expressed or implied by the specific benefit, contract, termination and other similar arrangements between the parties and the on-going versus project-oriented nature of the work to be performed. However, a definitive judicial interpretation of “employer” in the context of joint employer relationshipsthese forward-looking statements. Words such as, but not limited to, “anticipate,” “aim,” “believe,” “contemplate,” “continue,” “could,” “design,” “estimate,” “expect,” “intend,” “may,” “might,” “plan,” “predict,” “poise,” “project,” “potential,” “suggest,” “should,” “strategy,” “target,” “will,” “would,” and similar expressions or phrases, or the negative of those in which we engage hasexpressions or phrases, are intended to identify forward-looking statements, although not been established. For ERISA purposes, for example, courts have held that test factors relating to ability to control and supervise an individual are less important, while the U.S. Department of Labor has issued guidance that certain entities in the HR outsourcing industry do not qualify as common law employers for ERISA purposes. Moreover, when our app is fully functional, the scope of our employer status will increase, changing the legal analysis.all forward-looking statements contain these identifying words. Although we believe that we qualify as an employer of our worksite employees under ERISA, and the U.S. Department of Labor has not provided guidance otherwise, we are not able to predict the outcome of any future regulatory challenge.

If we are not recognized as an employer under the Code or ERISA, we may be required to change the method by which we report and remit payroll taxes to the tax authorities and the method by which we provide, or discontinue providing, certain employee benefits to our worksite employees, which could have a material adverse effectreasonable basis for each forward-looking statement contained in this prospectus and incorporated by reference into this prospectus, we caution you that these statements are based on our business and results of operations.

We must also qualify as an employer of our worksite employees under state regulations, which govern licensing, certification and registration requirements for PEOs. Nearly all states have enacted laws and regulations in this regard. While we believe that we qualify as an employer of our worksite employees under these state regulations, these requirements vary from state to state and change frequently and if we are not able to satisfy existing or future licensing requirements or other applicable regulations of any states, we may be prohibited from doing business in that state.

Failure to secure any necessary registrations or licensure could affect our ability to operate certain segments of our business in certain jurisdictions.

Some states require licensure or registration of businesses offering PEO services. Oneprojections of the service offeringsfuture that we provide is PEO services. If we need and are unable to secure registration or licensure of such service offering in a particular state, our ability to grow that segment of our business in such state would be impaired and could affect our ability to increase our revenues and meet certain customer requirements in such states.

Economic, Catastrophic and Geopolitical Risks

Catastrophic events or geopolitical conditions may disrupt our business.

Monetary and fiscal policies and political and economic conditions may substantially change. When there is a slowdown in the economy, employment levels may decrease with a corresponding impact on our businesses. Clients may react to worsening conditions by reducing their spending on payroll and other outsourcing services or renegotiating their contracts with us.

Worsening economic conditions, including inflation, recession, or other changes in economic conditions, may cause businesses to rely less on vendors in our business, which could adversely affect our revenue. If demand for our services declines, or business spending for such services declines, our revenue will be adversely affected.

Challenging economic conditions also may impair the ability of our customers to pay for products and services they have purchased. As a result, allowances for doubtful accounts and write-offs of accounts receivable may increase.

27

Table of Contents

We are dependent upon various large banks to execute Automated Clearing House and wire transfers as part of our client payroll and tax services. A systemic shutdown of the banking industry would impede our ability to process funds on behalf of our payroll and tax services clients and could have an adverse impact on our financial results and liquidity.

A disruption or failure of our systems or operations because of a major earthquake, weather event, cyber-attack, terrorist attack, or other catastrophic event could cause delays in completing sales, providing services, or performing other critical functions. Our corporate headquarters, a significant portion of our research and development activities, and certain other essential business operations are in the Irvine, California, area, which is a seismically active region. A catastrophic event that results in the destruction or disruption of any of our critical business or IT systems could harm our ability to conduct normal business operations.

Abrupt political change and terrorist activity may pose threats to our business and increase our operating costs. These conditions also may add uncertainty to the timing and budget for technology investment decisions by our customers and may cause supply chain disruptions for hardware manufacturers. Geopolitical change may result in changing regulatory requirements that could impact our operating strategies, hiring, and profitability.

Market Risks

Our Common Stock is thinly traded, which can cause volatility in its price.

Our Common Stock is listed for trading on the Nasdaq Capital Market, LLC, and is thinly traded. Thinly traded stock can be more susceptible to market volatility and can be particularly targeted by short sellers. This market volatility could significantly affect the market price of our Common Stock without regard to our operating performance. Securities markets worldwide experience significant price and volume fluctuations. In addition, the price of our Common Stock could be subject to wide fluctuations in response to the following factors, among others:

The market price of our Common Stock will also be impacted by our quarterly operating results which can fluctuate from quarter to quarter.

Uncertainties in the interpretation and application of the 2017 Tax Cuts and Jobs Act could materially affect our tax obligations and effective tax rate.

The 2017 Tax Cuts and Jobs Act (the Tax Act) was enacted on December 22, 2017, and significantly affected U.S. tax law by changing how the U.S. imposes income tax on U.S. and multinational corporations. The U.S. Department of Treasury has broad authority to issue regulations and interpretative guidance that may significantly impact how we will apply the law which could impact our tax obligations in the period issued.

The Tax Act requires complex computations not previously required under U.S. tax law. As such, the application of accounting guidance for such items is currently uncertain. Further, compliance with the Tax Act and the accounting for such provisions could require accumulation of information not previously required or regularly produced. Additional regulatory guidance as issued by the applicable taxing authorities, could materially affect our tax obligations and effective tax rate

28

Table of Contents

Risks Related to this Offering

The market price of our Common Stock may fluctuate, and you could lose all or part of your investment.

The offering price for our Common Stock will be agreed between us and the underwriters based on a number of factors and may not be indicative of prices that will prevail on NASDAQ or elsewhere following this offering. The price of our Common Stock may decline following this offering. The stock market in general, and the market price of our Common Stock will likely be subject to fluctuation, whether due to, or irrespective of, our operating results, financial condition and prospects.

Our financial performance, our industry’s overall performance, changing consumer preferences, technologies and advertiser requirements, government regulatory action, tax laws and market conditions in general could have a significant impact on the future market price of our Common Stock. Some of the other factors that could negatively affectmay cause our share priceactual results, level of activity, performance or resultachievements expressed or implied by these forward-looking statements, to differ. The section in fluctuationsthis prospectus entitled “Risk Factors” and the sections in our share price include:

29

Table of Contents

We may not be able to maintain compliance with the Nasdaq Capital Market’s continued listing requirements.

Our common stock is listed on the Nasdaq Capital Market. There are a numberperiodic reports, including our Annual Report entitled “Risk Factors” and “Description of continued listing requirements that we must satisfy in order to maintain our listing on the Nasdaq Capital Market. Although we intend to comply with all of the continued listing requirements, it is possible we may fail to do so. If we fail to maintain compliance with all applicable continued listing requirements for the Nasdaq Capital Market and they determine to delist our common stock, the delisting could adversely affect the market liquidity of our common stock, our ability to obtain financing, to repay any future debt we could incur and fund our operations.

We do not expect to declare or pay dividends in the foreseeable future.

We do not expect to declare or pay dividends in the foreseeable future, as we anticipate that we will invest future earnings in the development and growth of our business. Therefore, holders of our Common Stock will not receive any return on their investment unless they sell their securities, and holders may be unable to sell their securities on favorable terms or at all.

Sales of our Common Stock under Rule 144 could reduce the price of our stock.

There are as of November 30, 2018, 4,595,598 of our Common Stock held by non-affiliates and 25,227,224 shares of Common Stock held by affiliates that Rule 144 of the Securities Act (“Rule 144”) defines as restricted securities that can only be resold if the conditions of Rule 144 are met. In general, persons holding restricted securities, including affiliates, must hold their shares of Common Stock for a period of at least six months, may not sell more than one percent of the total issued and outstanding shares of Common Stock in any 90-day period, and must resell their shares in an unsolicited brokerage transaction at the market price. The availability for sale of substantial amounts of Common Stock under Rule 144 could reduce prevailing market prices for our securities.

Because our audit committee is new and small, we are subject to increased risk related to financial statement disclosures.

Our audit committee currently consists of three independent directors. While we endeavor to keep our independent directors informed regarding the state of the internal controls over financial reporting, our independent directors rely upon our financial personnel to advise our audit committee with regard to such matters. Accordingly, we are subject to increased risk related to financial statement disclosures.

Certain of our shareholders hold a significant percentage of our outstanding voting securities, which could reduce the ability of minority shareholders to effect certain corporate actions.

As of November 30, 2018, excluding unvested shares of Common Stock that they may acquire through the exercise of options issued pursuant to the 2017 Plan, our majority shareholders are the beneficial owners of approximately 74.9% of our outstanding voting securities. As a result of this ownership, such shareholders possess and can continue to possess significant influence and can elect and can continue to elect a majority of our board of directors and authorize or prevent proposed significant corporate transactions. In addition, upon the exercise of the options to purchase shares of our preferred stock, the holders of the preferred stock would be entitled to elect a majority of the board according to the terms of the preferred stock. Their ownership and control may also have the effect of delaying or preventing a future change in control, impeding a merger, consolidation, takeover or other business combination or discourage a potential acquirer from making a tender offer.

30

Table of Contents

Despite our election to become a public reporting company under the Exchange Act, we will publicly report on an ongoing basis as an “emerging growth company” under the reporting rules set forth under the Exchange Act. If we terminate our election to operate as a publicly reporting company under the Exchange Act, we will nevertheless be required to publicly report on an ongoing basis under the reporting rules set forth in Regulation A for Tier 2 issuers. In either case, we will be subject to ongoing public reporting requirements that are less rigorous than Exchange Act rules for companies that are not “emerging growth companies”, and our shareholders could receive less information than they might expect to receive from more mature public companies.

Although we have elected to become a public reporting company under the Exchange Act, we will be required to publicly report on an ongoing basis as an “emerging growth company” (as defined in the Jumpstart Our Business, Startups Act of 2012) under the reporting rules set forth under the Exchange Act. For so long as we remain an “emerging growth company,” we may take advantage of certain exemptions from various reporting requirements that are applicable to other Exchange Act reporting companies that are not “emerging growth companies”, including but not limited to:

We expect to take advantage of these reporting exemptions until we are no longer an emerging growth company. We would remain an “emerging growth company” for up to five years, although we will cease to be an emerging growth company upon the earliest of the:

If we cease to become a public reporting company under the Exchange Act, we will be required to publicly report on an ongoing basis under the reporting rules set forth in Regulation A for Tier 2 issuers. The ongoing reporting requirements under Regulation A are more relaxed than for “emerging growth companies” under the Exchange Act. The differences include, but are not limited to, being required to file only annual and semiannual reports, rather than annual and quarterly reports. Annual reports are due within 120 calendar days after the end of the issuer’s fiscal year, and semiannual reports are due within 90 calendar days after the end of the first six months of the issuer’s fiscal year.

In either case, we will be subject to ongoing public reporting requirements that are less rigorous than Exchange Act rules for companies that are not “emerging growth companies,” and our shareholders could receive less information than they might expect to receive from more mature public companies.

31

Table of Contents

The preparation of our consolidated financial statements involves the use of estimates, judgments and assumptions, and our consolidated financial statements may be materially affected if such estimates, judgments or assumptions prove to be inaccurate.

Financial statements prepared in accordance with accounting principles generally accepted in the United States of America (“GAAP”) typically require the use of estimates, judgments and assumptions that affect the reported amounts. Often, different estimates, judgments and assumptions could reasonably be used that would have a material effectmost recent quarterly report on such financial statements, and changes in these estimates, judgments and assumptions may occur from period to period over time. Significant areas of accounting requiring the application of management’s judgment include, but are not limited to, determining the fair value of assets and the timing and amount of cash flows from assets. These estimates, judgments and assumptions are inherently uncertain and, if our estimates were to prove to be wrong, we would face the risk that charges to income or other financial statement changes or adjustments would be required. Any such charges or changes could harm our business, including our financial condition and results of operations and the price of our securities. SeeForm 10-Q entitled “Management’s Discussion and Analysis of Financial Condition and Results of Operations” for a discussionOperations,” as well as other sections in this prospectus and the documents or reports incorporated by reference into this prospectus, discuss some of the accountingfactors that could contribute to these differences. These forward-looking statements include, among other things, statements about:

We may not actually achieve the plans, intentions or expectations disclosed in our forward-looking statements, and you should not place undue reliance on our forward-looking statements. Forward-looking statements should be regarded solely as our current plans, estimates judgments and assumptionsbeliefs. We have included important factors in the cautionary statements included in this document and incorporated by reference, particularly in the section entitled “Risk Factors” beginning on page 19 of our Annual Report that we believe could cause actual results or events to differ materially from the forward-looking statements that we make. Moreover, we operate in a very competitive and rapidly changing environment. New risks emerge from time to time. It is not possible for our management to predict all risks, nor can we assess the impact of all factors on our business or the extent to which any factor, or combination of factors, may cause actual results to differ materially from those contained in any forward-looking statements we may make. Given these risks and uncertainties, readers are the most criticalcautioned not to an understanding of our consolidated financialplace undue reliance on such forward-looking statements. All forward-looking statements and our business.

If securities industry analystsare qualified in their entirety by this cautionary statement. Our forward-looking statements do not publish research reports on us,reflect the potential impact of any future acquisitions, mergers, dispositions, joint ventures or publish unfavorable reports on us, then the market price and market trading volume of our Common Stock could be negatively affected.

Any trading market for our Common Stock will be influenced in part by any research reports that securities industry analysts publish about us. We do not currently have and may never obtain research coverage by securities industry analysts. If no securities industry analysts commence coverage of us, the market price and market trading volume of our Common Stock could be negatively affected. In the event we are covered by analysts, and one or more of such analysts downgrade our securities, or otherwise reports on us unfavorably, or discontinues coverage or us, the market price and market trading volume of our Common Stock could be negatively affected.

Future issuances of our Common Stock or securities convertible into our Common Stock or the trading of outstanding stock, could cause the market price of our Common Stock to decline and would result in the dilution of your shareholding.

Future issuances of our Common Stock or securities convertible into our Common Stock or the trading of outstanding stock, could cause the market price of our Common Stock to decline. We cannot predict the effect, if any, of future issuances of our Common Stock or securities convertible into our Common Stock, on the price of our Common Stock. In all events, future issuances of our Common Stock would result in the dilution of your shareholding. In addition, the perception that new issuances of our Common Stock or other securities convertible into our Common Stock, could occur, could adversely affect the market price of our Common Stock.

32

Table of Contents

Future issuances of debt securities, which would rank senior to our Common Stock upon our bankruptcy or liquidation, and future issuances of preferred stock, which would rank senior to our Common Stock for the purposes of dividends and liquidating distributions, may adversely affect the level of return you may be able to achieve from an investment in our Common Stock.

In the future,investments we may attempt to increase our capital resources by offering debt securities. Upon bankruptcy or liquidation, holders of our debt securities, and lenders with respect to other borrowings we may make, would receive distributions of our available assets prior to any distributions being made to holders of our Common Stock. Moreover, if we issue additional preferred stock, the holders of such preferred stock could be entitled to preferences over holders of Common Stock in respect of the payment of dividends and the payment of liquidating distributions. Because our decision to issue debt or preferred securities in any future offering, or borrow money from lenders, will depend in part on market conditions and other factors beyond our control, we cannot predict or estimate the amount, timing or nature of any such future offerings or borrowings. Holders of our Common Stock must bear the risk that any future offerings we conduct or borrowings we make may adversely affect the level of return they may be able to achieve from an investment in our Common Stock.

INCORPORATION BY REFERENCE

The SEC allows us to “incorporate by reference” intomake. You should read this prospectus and the information in other documents that we file with it. This means that we can disclose important informationhave filed as exhibits to you by referring you to those documents. The informationthis prospectus and incorporated by reference is considered to be a part of this prospectus,herein completely and information in documents that we file later with the SEC will automatically updateunderstanding that our actual future results may be materially different from the plans, intentions and supersede information containedexpectations disclosed in documents filed earlier with the SECforward-looking statements we make. Although we believe that the expectations reflected in the forward-looking statements are reasonable, we cannot guarantee future results, levels of activity or performance. The forward-looking statements contained in this prospectus. We incorporate by reference in this prospectus the documents listed below and any future filings that we may make with the SEC under Sections 13(a), 13(c), 14, or 15(d)are made as of the Exchange Act prior to the termination of the offering under this prospectus; provided, however, that we are not incorporating, in each case, any documents or information deemed to have been furnished and not filed in accordance with SEC rules:

33

Table of Contents

Additionally, all documents filed by us with the SEC under Sections 13(a), 13(c), 14 or 15(d) of the Exchange Act after (i) the date of this Registration Statement and prior to effectiveness of this Registration Statement, and (ii) the date of this prospectus and before the termination or completion of any offering hereunder, shall be deemed to be incorporated by reference into this prospectus from the respective dates of filing of such documents, except that we do not incorporateassume any documentobligation to update any forward-looking statements, whether as a result of new information, future events or portion of a document that is “furnished” to the SEC, but not deemed “filed.”otherwise, except as required by applicable law.

We will provide, without charge, to each person to whom a copy ofYou should also consider carefully the statements set forth in the sections titled “Risk Factors” or elsewhere in this prospectus is delivered, including any beneficial owner, upon the written or oral request of such person, a copy of any or all ofand in the documents incorporated or deemed incorporated herein or therein by reference, herein, including exhibits. Requests should be directed to: ShiftPixy, Inc., Attention: Corporate Secretary, 1 Venture, Suite 150, Irvine, CA 92618. Tel (888) 798-9100.which address various factors that could cause results or events to differ from those described in the forward-looking statements.  All subsequent written and oral forward-looking statements attributable to us or to persons acting on our behalf are expressly qualified in their entirety by the applicable cautionary statements.  We have no plans to update these forward-looking statements.

USE OF PROCEEDS

All shares of our Common Stock offered by this prospectus are being registered for the account of the selling shareholders identified herein. We will not receive any of the proceeds from the sale of such shares.Common Stock by the selling shareholders named in this prospectus, and the selling shareholders will receive all of the proceeds from this offering.

However, weWe may receive up to approximately $12.66 million in aggregate gross proceeds from any cash exerciseexercises of the March Warrants, which, if exercised in cash with respect to 2,926,137 shares of Common Stock which may be acquired under 2,926,137based on the per share exercise price of the March Warrants and offered hereby, would result in gross proceeds to us of approximately $,4,971,000; however,Warrants. Although we cannot predict when and in what amounts or if the March Warrants will be exercised, and it is possible that the March Warrants may expire and never be exercised, in which case we would not receive any cash proceeds.

 We intendare permitted to use any proceeds received by uswe receive from the cash exercise of the Warrants for working capital and general corporate purposes. Aspurposes, we anticipate that the bulk of the proceeds from Warrant exercises, depending upon their timing, will be applied to funding our expenses in connection with our activities related to our sponsorship of the SPACs, as described above. The holders of the Warrants are not obligated to exercise their Warrants, and we cannot predict whether holders of the Warrants will choose to exercise all or any of their Warrants.

UNAUDITED PRO FORMA FINANCIAL INFORMATION

On October 22, 2021, IHC consummated the IHC IPO which raised $115 million of gross proceeds for IHC. In connection with the IHC IPO, we purchased, through Investments, 4,639,102 private placement warrants at a price of $1.00 per warrant, for an aggregate purchase price of $4,639,102. The unaudited pro forma balance sheet as of August 31, 2021 gives effect to the consummation of the IHC IPO as if the IHC IPO was consummated on August 31, 2021, the first day of Fiscal 2021. The unaudited pro forma income statement for the year ended August 31, 2021 gives effect to the consummation of the IHC IPO as if the IHC IPO was consummated on August 31, 2021, the first day of Fiscal 2021.

The unaudited pro forma balance sheet and the unaudited pro forma income statement should be read in conjunction with our historical consolidated financial statements and the related notes included in the Annual Report which are incorporated by reference herein. See “Information Incorporated By Reference.” The unaudited pro forma balance sheet and the unaudited pro forma income statement may not be useful in predicting the future financial condition and results of operations of our company. The actual financial condition and results of operations of our company may differ significantly from the pro forma amounts reflected herein due to a variety of factors.

Unaudited Pro Forma Balance Sheet