Document:

Exhibit 10.4

 

GUARANTY

 

This GUARANTY, dated
as of June __, 2020 (this “Guaranty”), is made by each of the undersigned (each a “Guarantor”,
and collectively, the “Guarantors”), in favor
of HT Investments MA LLC, in its capacity as collateral agent (in such capacity, the “Collateral Agent” as hereinafter
further defined) for the “Buyers” party to the Securities Purchase Agreement (each as defined below).

 

W
I T N E S S E T H :

 

WHEREAS, Akerna Corp.,
a Delaware corporation with offices located at 1630 Welton St., 4th Floor, Denver, CO 80202 (the “Company”),
and each party listed as a “Buyer” on the Schedule
of Buyers attached thereto (collectively, the “Buyers”)
are parties to the Securities Purchase Agreement, dated as of June 8, 2020 (as amended, restated, extended, replaced or otherwise
modified from time to time, the “Securities Purchase Agreement”),
pursuant to which the Company shall be required to sell, and the Buyers shall purchase or have the right to purchase, the “Notes”
issued pursuant thereto (as such Notes may be amended, restated, extended, replaced or otherwise modified from time to time in
accordance with the terms thereof, collectively, the “Notes”);

 

WHEREAS, the Securities
Purchase Agreement requires that the Guarantors execute and deliver to the Collateral Agent, (i) a guaranty guaranteeing all of
the obligations of the Company under the Securities Purchase Agreement, the Notes and the other Transaction Documents (as defined
below); and (ii) a Security and Pledge Agreement, dated as of the date hereof, granting the Collateral Agent a lien on and security
interest in all of their assets and properties (the “Security
Agreement”); and

 

WHEREAS, each Guarantor
has determined that the execution, delivery and performance of this Guaranty directly benefits, and is in the best interest of,
such Guarantor.

 

NOW, THEREFORE, in consideration
of the premises and the agreements herein and in order to induce the Buyers to perform under the Securities Purchase Agreement,
each Guarantor hereby agrees with each Buyer as follows:

 

Section
1.  Definitions.
Reference is hereby made to the Securities Purchase Agreement and the Notes for a statement of the terms thereof. All terms used
in this Guaranty and the recitals hereto which are defined in the Securities Purchase Agreement or the Notes, and which are not
otherwise defined herein shall have the same meanings herein as set forth therein. In addition, the following terms when used in
the Guaranty shall have the meanings set forth below:

 

“Bankruptcy
Code” means Chapter 11 of Title 11 of the United States Code, 11 U.S.C §§ 101 et seq. (or other applicable
bankruptcy, insolvency or similar laws).

 

“Business
Day” means any day other than Saturday, Sunday or other day on which commercial banks in New York City are authorized
or required by law to remain closed.

 

“Buyer”
or “Buyers” shall have the meaning set forth in the recitals hereto.

 

     

     

    

 

“Capital Stock”
means (i) with respect to any Person that is a corporation, any and all shares, interests, participations or other equivalents
(however designated and whether or not voting) of corporate stock (including, without limitation, any warrants, options, rights
or other securities exercisable or convertible into equity interests or securities of such Person), and (ii) with respect to any
Person that is not a corporation, any and all partnership, membership or other equity interests of such Person.

 

“Collateral”
means all assets and properties of the Company and each Guarantor, wherever located and whether now or hereafter existing and
whether now owned or hereafter acquired, of every kind and description, tangible or intangible, including, without limitation,
the collateral described in Section 2 of the Security Agreement.

 

“Collateral
Agent” shall have the meaning set forth in the recitals hereto.

 

“Company”
shall have the meaning set forth in the recitals hereto.

 

“Governmental
Authority” means any nation or government, any Federal, state, city, town, municipality, county, local, foreign or other
political subdivision thereof or thereto and any department, commission, board, bureau, instrumentality, agency or other entity
exercising executive, legislative, judicial, taxing, regulatory or administrative powers or functions of or pertaining to government.

 

“Guaranteed
Obligations” shall have the meaning set forth in Section 2 of this Guaranty.

 

“Guarantor”
or “Guarantors” shall have the meaning set forth in the recitals hereto.

 

“Indemnified
Party” shall have the meaning set forth in Section 13(a) of this Guaranty

 

“Insolvency
Proceeding” means any proceeding commenced by or against any Person under any provision of the Bankruptcy Code or under
any other bankruptcy or insolvency law, assignments for the benefit of creditors, formal or informal moratoria, compositions, or
extensions generally with creditors, or proceedings seeking reorganization, arrangement, or other similar relief.

 

“Notes”
shall have the meaning set forth in the recitals hereto.

 

“Obligations”
shall have the meaning set forth in Section 3 of the Security Agreement.

 

“Other Taxes”
shall have the meaning set forth in Section 12(a)(iv) of this Guaranty.

 

“Paid in Full”
or “Payment in Full” means the indefeasible payment in full in cash of all of the Guaranteed Obligations.

 

“Person”
means an individual, corporation, limited liability company, partnership, association, joint-stock company, trust, unincorporated
organization, joint venture or other enterprise or entity or Governmental Authority.

 

“Securities
Purchase Agreement” shall have the meaning set forth in the recitals hereto.

 

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“Security
Agreement” shall have the meaning set forth in the recitals hereto.

 

“Subsidiary”
and “Subsidiaries” shall have the respective meanings given to such terms in the Securities Purchase Agreement.

 

“Taxes”
shall have the meaning set forth in Section 12(a) of this Guaranty.

 

“Transaction
Party” means the Company and each Guarantor, collectively, “Transaction Parties”.

 

Section
2.  Guaranty.

 

(a)
The Guarantors, jointly and severally, hereby unconditionally and irrevocably, guaranty to the Collateral Agent, for the
benefit of the Collateral Agent and the Buyers, the punctual payment, as and when due and payable, by stated maturity or otherwise,
of all Obligations, including, without limitation, all interest, make-whole and other amounts that accrue after the commencement
of any Insolvency Proceeding of the Company or any Guarantor, whether or not the payment of such interest, make-whole and/or other
amounts are enforceable or are allowable in such Insolvency Proceeding, and all fees, interest, premiums, penalties, causes of
actions, costs, commissions, expense reimbursements, indemnifications and all other amounts due or to become due under any of the
Transaction Documents (all of the foregoing collectively being the “Guaranteed
Obligations”), and agrees to pay any and all costs and expenses (including counsel fees and expenses) incurred
by the Collateral Agent in enforcing any rights under this Guaranty or any other Transaction Document. Without limiting the generality
of the foregoing, each Guarantor’s liability hereunder shall extend to all amounts that constitute part of the Guaranteed
Obligations and would be owed by the Company to the Collateral Agent or any Buyer under the Securities Purchase Agreement and the
Notes but for the fact that they are unenforceable or not allowable due to the existence of an Insolvency Proceeding involving
any Transaction Party.

 

(b)
Each Guarantor, and by its acceptance of this Guaranty, the Collateral Agent and each Buyer, hereby confirms that it is
the intention of all such Persons that this Guaranty and the Guaranteed Obligations of each Guarantor hereunder not constitute
a fraudulent transfer or conveyance for purposes of the Bankruptcy Code, the Uniform Fraudulent Conveyance Act, the Uniform Fraudulent
Transfer Act or any similar foreign, federal, provincial, state, or other applicable law to the extent applicable to this Guaranty
and the Guaranteed Obligations of each Guarantor hereunder. To effectuate the foregoing intention, the Collateral Agent, the Buyers
and the Guarantors hereby irrevocably agree that the Guaranteed Obligations of each Guarantor under this Guaranty at any time shall
be limited to the maximum amount as will result in the Guaranteed Obligations of such Guarantor under this Guaranty not constituting
a fraudulent transfer or conveyance.

 

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Section
3.  Guaranty
Absolute; Continuing Guaranty; Assignments.

 

(a)
The Guarantors, jointly and severally, guaranty that the Guaranteed Obligations will be paid strictly in accordance with
the terms of the Transaction Documents, regardless of any law, regulation or order now or hereafter in effect in any jurisdiction
affecting any of such terms or the rights of the Collateral Agent or any Buyer with respect thereto. The obligations of each Guarantor
under this Guaranty are independent of the Guaranteed Obligations, and a separate action or actions may be brought and prosecuted
against any Guarantor to enforce such obligations, irrespective of whether any action is brought against any Transaction Party
or whether any Transaction Party is joined in any such action or actions. The liability of any Guarantor under this Guaranty shall
be as a primary obligor (and not merely as a surety) and shall be irrevocable, absolute and unconditional irrespective of, and
each Guarantor hereby irrevocably waives, to the extent permitted by law, any defenses it may now or hereafter have in any way
relating to, any or all of the following:

 

(i)
any lack of validity or enforceability of any Transaction Document;

 

(ii)
any change in the time, manner or place of payment of, or in any other term of, all or any of the Guaranteed Obligations,
or any other amendment or waiver of or any consent to departure from any Transaction Document, including, without limitation, any
increase in the Guaranteed Obligations resulting from the extension of additional credit to any Transaction Party or extension
of the maturity of any Guaranteed Obligations or otherwise;

 

(iii)
any taking, exchange, release or non-perfection of any Collateral;

 

(iv) any taking,
release or amendment or waiver of or consent to departure from any other guaranty, for all or any of the Guaranteed
Obligations;

 

(v)
any change, restructuring or termination of the corporate, limited liability company or partnership structure or existence
of any Transaction Party;

 

(vi)
any manner of application of Collateral or any other collateral, or proceeds thereof, to all or any of the Guaranteed Obligations,
or any manner of sale or other disposition of any Collateral or any other collateral for all or any of the Guaranteed Obligations
or any other Obligations of any Transaction Party under the Transaction Documents or any other assets of any Transaction Party
or any of its Subsidiaries;

 

(vii)
any failure of the Collateral Agent or any Buyer to disclose to any Transaction Party any information relating to the business,
condition (financial or otherwise), operations, performance, properties or prospects of any other Transaction Party now or hereafter
known to the Collateral Agent or any Buyer (each Guarantor waiving any duty on the part of the Collateral Agent or any Buyer to
disclose such information);

 

(viii)
taking any action in furtherance of the release of any Guarantor or any other Person that is liable for the Obligations
from all or any part of any liability arising under or in connection with any Transaction Document without the prior written consent
of the Collateral Agent; or

 

(ix)
any other circumstance (including, without limitation, any statute of limitations) or any existence of or reliance on any
representation by the Collateral Agent or any Buyer that might otherwise constitute a defense available to, or a discharge of,
any Transaction Party or any other guarantor or surety.

 

(b)
This Guaranty shall continue to be effective or be reinstated, as the case may be, if at any time any payment of any of
the Guaranteed Obligations is rescinded or must otherwise be returned by the Collateral Agent, any Buyer, or any other Person upon
the insolvency, bankruptcy or reorganization of any Transaction Party or otherwise, all as though such payment had not been made.

 

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(c)
This Guaranty is a continuing guaranty and shall (i) remain in full force and effect until Payment in Full of the Guaranteed
Obligations (other than inchoate indemnity obligations) and shall not terminate for any reason prior to the respective Maturity
Date of each Note (other than Payment in Full of the Guaranteed Obligations) and (ii) be binding upon each Guarantor and its respective
successors and assigns. This Guaranty shall inure to the benefit of and be enforceable by the Collateral Agent, the Buyers, and
their respective successors, and permitted pledgees, transferees and assigns. Without limiting the generality of the foregoing
sentence, the Collateral Agent or any Buyer may pledge, assign or otherwise transfer all or any portion of its rights and obligations
under and subject to the terms of any Transaction Document to any other Person, and such other Person shall thereupon become vested
with all the benefits in respect thereof granted to the Collateral Agent or such Buyer (as applicable) herein or otherwise, in
each case as provided in the Securities Purchase Agreement or such Transaction Document.

 

Section
4.  Waivers.
To the extent permitted by applicable law, each Guarantor hereby waives promptness, diligence, protest, notice of acceptance and
any other notice or formality of any kind with respect to any of the Guaranteed Obligations and this Guaranty and any requirement
that the Collateral Agent exhaust any right or take any action against any Transaction Party or any other Person or any Collateral.
Each Guarantor acknowledges that it will receive direct and indirect benefits from the financing arrangements contemplated herein
and that the waiver set forth in this Section 4 is
knowingly made in contemplation of such benefits. The Guarantors hereby waive any right to revoke this Guaranty, and acknowledge
that this Guaranty is continuing in nature and applies to all Guaranteed Obligations, whether existing now or in the future. Without
limiting the foregoing, to the extent permitted by applicable law, each Guarantor hereby unconditionally and irrevocably waives
(a) any defense arising by reason of any claim or defense based upon an election of remedies by the Collateral Agent or any
Buyer that in any manner impairs, reduces, releases or otherwise adversely affects the subrogation, reimbursement, exoneration,
contribution or indemnification rights of such Guarantor or other rights of such Guarantor to proceed against any of the other
Transaction Parties, any other guarantor or any other Person or any Collateral, and (b) any defense based on any right of
set-off or counterclaim against or in respect of the Guaranteed Obligations of such Guarantor hereunder. Each Guarantor hereby
unconditionally and irrevocably waives any duty on the part of the Collateral Agent or any Buyer to disclose to such Guarantor
any matter, fact or thing relating to the business, condition (financial or otherwise), operations, performance, properties or
prospects of any other Transaction Party or any of its Subsidiaries now or hereafter known by the Collateral Agent or a Buyer.

 

Section
5.  Subrogation.
No Guarantor may exercise any rights that it may now or hereafter acquire against any Transaction Party or any other guarantor
that arise from the existence, payment, performance or enforcement of any Guarantor’s obligations under this Guaranty, including,
without limitation, any right of subrogation, reimbursement, exoneration, contribution or indemnification and any right to participate
in any claim or remedy of the Collateral Agent or any Buyer against any Transaction Party or any other guarantor or any Collateral,
whether or not such claim, remedy or right arises in equity or under contract, statute or common law, including, without limitation,
the right to take or receive from any Transaction Party or any other guarantor, directly or indirectly, in cash or other property
or by set-off or in any other manner, payment or security solely on account of such claim, remedy or right, unless and until there
has been Payment in Full of the Guaranteed Obligations. If any amount shall be paid to a Guarantor in violation of the immediately
preceding sentence at any time prior to Payment in Full of the Guaranteed Obligations and all other amounts payable under this
Guaranty, such amount shall be held in trust for the benefit of the Collateral Agent and shall forthwith be paid to the Collateral
Agent to be credited and applied to the Guaranteed Obligations and all other amounts payable under this Guaranty, whether matured
or unmatured, in accordance with the terms of the Transaction Document, or to be held as Collateral for any Guaranteed Obligations
or other amounts payable under this Guaranty thereafter arising. If (a) any Guarantor shall make payment to the Collateral
Agent of all or any part of the Guaranteed Obligations, and (b) there has been Payment in Full of the Guaranteed Obligations, the
Collateral Agent will, at such Guarantor’s request and expense, execute and deliver to such Guarantor appropriate documents,
without recourse and without representation or warranty, necessary to evidence the transfer by subrogation to such Guarantor of
an interest in the Guaranteed Obligations resulting from such payment by such Guarantor.

 

    	 	5	 

     

    

 

Section
6.  Representations,
Warranties and Covenants.

 

(a)
Each Guarantor, jointly and severally with each other Grantor, hereby represents and warrants with respect to itself and
each other Grantor as of the date first written above as follows:

 

(i)
such Guarantor (A) is a corporation, limited liability company or limited partnership duly organized, validly existing and
in good standing under the laws of the jurisdiction of its organization as set forth on the signature pages hereto, (B) has all
requisite corporate, limited liability company or limited partnership power and authority to conduct its business as now conducted
and as presently contemplated and to execute, deliver and perform its obligations under this Guaranty and each other Transaction
Document to which such Guarantor is a party, and to consummate the transactions contemplated hereby and thereby and (C) is duly
qualified to do business and is in good standing in each jurisdiction in which the character of the properties owned or leased
by it or in which the transaction of its business makes such qualification necessary except where the failure to be so qualified
(individually or in the aggregate) would not result in a Material Adverse Effect.

(ii)
The execution, delivery and performance by such Guarantor of this Guaranty and each other Transaction Document to which
such Guarantor is a party (A) have been duly authorized by all necessary corporate, limited liability company or limited partnership
action, (B) do not and will not contravene its charter, articles, certificate of formation or by-laws, its limited liability company
or operating agreement or its certificate of partnership or partnership agreement, as applicable, or any applicable law or any
contractual restriction binding on such Guarantor or its properties do not and will not result in or require the creation of any
lien, security interest or encumbrance (other than pursuant to any Transaction Document) upon or with respect to any of its properties,
and (C) do not and will not result in any default, noncompliance, suspension, revocation, impairment, forfeiture or nonrenewal
of any material permit, license, authorization or approval applicable to it or its operations or any of its properties.

 

(iii)
No authorization or approval or other action by, and no notice to or filing with, any Governmental Authority or other Person
is required in connection with the due execution, delivery and performance by such Guarantor of this Guaranty or any of the other
Transaction Documents to which such Guarantor is a party (other than expressly provided for in any of the Transaction Documents).

 

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(iv)
This Guaranty has been duly executed and delivered by each Guarantor and is, and each of the other Transaction Documents
to which such Guarantor is or will be a party, when executed and delivered, will be, a legal, valid and binding obligation of such
Guarantor, enforceable against such Guarantor in accordance with its terms, except as may be limited by the Bankruptcy Code or
other applicable bankruptcy, insolvency, reorganization, moratorium, fraudulent conveyance, suretyship or similar laws and equitable
principles (regardless of whether enforcement is sought in equity or at law).

 

(v)
There is no pending or, to the best knowledge of such Guarantor, threatened action, suit or proceeding against such Guarantor
or to which any of the properties of such Guarantor is subject, before any court or other Governmental Authority or any arbitrator
that (A) if adversely determined, could reasonably be expected to have a Material Adverse Effect or (B) relates to this
Guaranty or any of the other Transaction Documents to which such Guarantor is a party or any transaction contemplated hereby or
thereby.

 

(vi)
Such Guarantor (A) has read and understands the terms and conditions of the Securities Purchase Agreement and the other
Transaction Documents, and (B) now has and will continue to have independent means of obtaining information concerning the
affairs, financial condition and business of the Company and the other Transaction Parties, and has no need of, or right to obtain
from the Collateral Agent or any Buyer, any credit or other information concerning the affairs, financial condition or business
of the Company or the other Transaction Parties.

 

(vii)
There are no conditions precedent to the effectiveness of this Guaranty that have not been satisfied or waived.

 

(b)
Each Guarantor covenants and agrees that until Payment in Full of the Guaranteed Obligations, it will comply with each of
the covenants (except to the extent applicable only to a public company) which are set forth in Section 4 of the Securities
Purchase Agreement as if such Guarantor were a party thereto.

 

Section
7.  Right
of Set-off. Upon the occurrence and during the continuance of any Event of Default, the Collateral Agent and any Buyer
may, and is hereby authorized to, at any time and from time to time, without notice to the Guarantors (any such notice being expressly
waived by each Guarantor) and to the fullest extent permitted by law, set-off and apply any and all deposits (general or special,
time or demand, provisional or final) at any time held and other indebtedness at any time owing by the Collateral Agent or any
Buyer to or for the credit or the account of any Guarantor against any and all obligations of the Guarantors now or hereafter existing
under this Guaranty or any other Transaction Document, irrespective of whether or not the Collateral Agent or any Buyer shall have
made any demand under this Guaranty or any other Transaction Document and although such obligations may be contingent or unmatured.
The Collateral Agent and each Buyer agrees to notify the relevant Guarantor promptly after any such set-off and application made
by the Collateral Agent or such Buyer, provided that the failure to give such notice shall not affect the validity of such set-off
and application. The rights of the Collateral Agent or any Buyer under this Section 7
are in addition to other rights and remedies (including, without limitation, other rights of set-off) which the Collateral Agent
or such Buyer may have under this Guaranty or any other Transaction Document in law or otherwise.

 

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Section
8.  Limitation
on Guaranteed Obligations.

 

(a)
Notwithstanding any provision herein contained to the contrary, each Guarantor’s liability hereunder shall be limited
to an amount not to exceed as of any date of determination the greater of:

 

(i)
the amount of all Guaranteed Obligations, plus interest thereon at the applicable Interest Rate as specified in the Note;
and

 

(ii)
the amount which could be claimed by the Collateral Agent from any Guarantor under this Guaranty without rendering such
claim voidable or avoidable under the Bankruptcy Code or under any applicable state Uniform Fraudulent Transfer Act, Uniform Fraudulent
Conveyance Act or similar statute or common law after taking into account, among other things, Guarantor’s right of contribution
and indemnification.

 

(b)
Each Guarantor agrees that the Guaranteed Obligations may at any time and from time to time exceed the amount of the liability
of such Guarantor hereunder without impairing the guaranty hereunder or affecting the rights and remedies of the Collateral Agent
or any Buyer hereunder or under applicable law.

 

(c)
No payment made by the Company, any Guarantor, any other guarantor or any other Person or received or collected by the Collateral
Agent or any other Buyer from the Company, any of the Guarantors, any other guarantor or any other Person by virtue of any action
or proceeding or any set-off or appropriation or application at any time or from time to time in reduction of or in payment of
the Guaranteed Obligations shall be deemed to modify, reduce, release or otherwise affect the liability of any Guarantor hereunder
which shall, notwithstanding any such payment (other than any payment made by such Guarantor in respect of the Guaranteed Obligations
or any payment received or collected from such Guarantor in respect of the Guaranteed Obligations), remain liable for the Guaranteed
Obligations up to the maximum liability of such Guarantor hereunder until after all of the Guaranteed Obligations and all other
amounts payable under this Guaranty shall have been Paid in Full.

 

Section
9.  Notices,
Etc. Any notices, consents, waivers or other communications required or permitted to be given under the terms of this Guaranty
must be in writing and will be deemed to have been delivered: (i) upon receipt, when delivered personally; (ii) upon receipt, when
sent by facsimile (provided confirmation of transmission is mechanically or electronically generated and kept on file by the sending
party); or (iii) one (1) Business Day after deposit with an nationally recognized overnight courier service with next day delivery
specified, in each case, properly addressed to the party to receive the same. All notices and other communications provided for
hereunder shall be sent, if to any Guarantor, to the Company’s address and/or facsimile number, or if to the Collateral Agent
or any Buyer, to it at its respective address and/or facsimile number, each as set forth in Section 9(f) of the Securities Purchase
Agreement

 

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Section
10. Governing Law; Jurisdiction. All questions concerning the construction, validity, enforcement and
interpretation of this Guaranty shall be governed by the internal laws of the State of New York, without giving effect to any
choice of law or conflict of law provision or rule (whether of the State of New York or any other jurisdictions) that would
cause the application of the laws of any jurisdiction other than the State of New York. Each Guarantor hereby irrevocably
submits to the exclusive jurisdiction of the state and federal courts sitting in The City of New York, Borough of Manhattan,
for the adjudication of any dispute hereunder or in connection herewith or under any of the other Transaction Documents or
with any transaction contemplated hereby or thereby, and hereby irrevocably waives, and agrees not to assert in any suit,
action or proceeding, any claim, obligation or defense that it is not personally subject to the jurisdiction of any such
court, that such suit, action or proceeding is brought in an inconvenient forum or that the venue of such suit, action or
proceeding is improper. Each party hereby irrevocably waives personal service of process and consents to process being served
in any such suit, action or proceeding by mailing a copy thereof to such party at the address for such notices to it under
Section 9(f) of the Securities Purchase Agreement and agrees that such service shall constitute good and sufficient service
of process and notice thereof. Nothing contained herein shall be deemed to limit in any way any right to serve process in any
manner permitted by law. Nothing contained herein shall be deemed or operate to preclude the Collateral Agent or the Buyers
from bringing suit or taking other legal action against any Guarantor in any other jurisdiction to collect on a
Guarantor’s obligations or to enforce a judgment or other court ruling in favor of the Collateral Agent or a Buyer.

 

Section
11.  WAIVER OF JURY TRIAL, ETC.
EACH GUARANTOR HEREBY IRREVOCABLY WAIVES ANY RIGHT IT MAY HAVE TO, AND AGREES NOT TO REQUEST, A JURY TRIAL FOR THE ADJUDICATION
OF ANY DISPUTE HEREUNDER OR UNDER ANY OTHER TRANSACTION DOCUMENT OR IN CONNECTION WITH OR ARISING OUT OF THIS GUARANTY, ANY OTHER
TRANSACTION DOCUMENT OR ANY TRANSACTION CONTEMPLATED HEREBY OR THEREBY.

 

Section
12.  Taxes.

 

(a)
All payments made by any Guarantor hereunder or under any other Transaction Document shall be made in accordance with the
terms of the respective Transaction Document and shall be made without set-off, counterclaim, withholding, deduction or other defense.
Without limiting the foregoing, all such payments shall be made free and clear of and without deduction or withholding for any
present or future taxes, levies, imposts, deductions, charges or withholdings, and all liabilities with respect thereto, excluding
taxes imposed on the net income of the Collateral Agent or any Buyer by the jurisdiction in which the Collateral Agent or such
Buyer is organized or where it has its principal lending office (all such nonexcluded taxes, levies, imposts, deductions, charges,
withholdings and liabilities, collectively or individually, “Taxes”).
If any Guarantor shall be required to deduct or to withhold any Taxes from or in respect of any amount payable hereunder or under
any other Transaction Document:

 

(i)
the amount so payable shall be increased to the extent necessary so that after making all required deductions and withholdings
(including Taxes on amounts payable to the Collateral Agent or any Buyer pursuant to this sentence) the Collateral Agent or each
Buyer receives an amount equal to the sum it would have received had no such deduction or withholding been made,

 

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(ii)
such Guarantor shall make such deduction or withholding,

 

(iii)
such Guarantor shall pay the full amount deducted or withheld to the relevant Governmental Authority in accordance with
applicable law, and

 

(iv)
as promptly as possible thereafter, such Guarantor shall send the Collateral Agent or each Buyer an official receipt (or,
if an official receipt is not available, such other documentation as shall be satisfactory to the Collateral Agent, as the case
may be) showing payment.  In addition, each Guarantor agrees to pay any present or future stamp or documentary taxes or any
other excise or property taxes, charges or similar levies that arise from any payment made hereunder or from the execution, delivery,
registration or enforcement of, or otherwise with respect to, this Guaranty or any other Transaction Document (collectively, “Other
Taxes”).

 

(b)
Each Guarantor hereby indemnifies and agrees to hold each Indemnified Party harmless from and against Taxes or Other Taxes
(including, without limitation, any Taxes or Other Taxes imposed by any jurisdiction on amounts payable under this Section 12)
paid by any Indemnified Party  as a result of any payment made hereunder or from the execution, delivery, registration or
enforcement of, or otherwise with respect to, this Guaranty or any other Transaction Document, and any liability (including penalties,
interest and expenses for nonpayment, late payment or otherwise) arising therefrom or with respect thereto, whether or not such
Taxes or Other Taxes were correctly or legally asserted.  This indemnification shall be paid within thirty (30) days from
the date on which the Collateral Agent or such Buyer makes written demand therefor, which demand shall identify the nature and
amount of such Taxes or Other Taxes.

 

(c)
If any Guarantor fails to perform any of its obligations under this Section 12,
such Guarantor shall indemnify the Collateral Agent and each Buyer for any taxes, interest or penalties that may become payable
as a result of any such failure. The obligations of the Guarantors under this Section 12
shall survive the termination of this Guaranty and the payment of the Obligations and all other amounts payable hereunder.

 

Section
13.  Indemnification.

 

(a)
Without limitation of any other obligations of any Guarantor or remedies of the Collateral Agent or the Buyers under this
Guaranty or applicable law, except to the extent resulting from such Indemnified Party’s gross negligence, fraud or willful
misconduct, as determined by a final judgment of a court of competent jurisdiction no longer subject to appeal, each Guarantor
shall, to the fullest extent permitted by law, indemnify, defend and save and hold harmless the Collateral Agent and each Buyer
and each of their affiliates and their respective officers, directors, employees, agents and advisors (each, an “Indemnified
Party”) from and against, and shall pay on demand, any and all claims, damages, losses, liabilities and expenses (including,
without limitation, reasonable fees and expenses of counsel) that may be incurred by or asserted or awarded against any Indemnified
Party in connection with or as a result of any failure of any Guaranteed Obligations to be the legal, valid and binding obligations
of any Transaction Party enforceable against such Transaction Party in accordance with their terms.

 

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(b)
Each Guarantor hereby also agrees that none of the Indemnified Parties shall have any liability (whether direct or indirect,
in contract, tort or otherwise) or any fiduciary duty or obligation to any of the Guarantors or any of their respective affiliates
or any of their respective officers, directors, employees, agents and advisors, and each Guarantor hereby agrees not to assert
any claim against any Indemnified Party on any theory of liability, for special, indirect, consequential, incidental or punitive
damages arising out of or otherwise relating to the facilities, the actual or proposed use of the proceeds of the advances, the
Transaction Documents or any of the transactions contemplated by the Transaction Documents.

 

Section
14.  Miscellaneous.

 

(a)
Each Guarantor will make each payment hereunder in lawful money of the United States of America and in immediately available
funds to the Collateral Agent or each Buyer, at such address specified by the Collateral Agent or such Buyer from time to time
by notice to the Guarantors.

 

(b)
No amendment or waiver of any provision of this Guaranty and no consent to any departure by any Guarantor therefrom shall
in any event be effective unless the same shall be in writing and signed by each Guarantor, the Collateral Agent and each Buyer,
and then such waiver or consent shall be effective only in the specific instance and for the specific purpose for which given.

 

(c)
No failure on the part of the Collateral Agent or any Buyer to exercise, and no delay in exercising, any right or remedy
hereunder or under any other Transaction Document shall operate as a waiver thereof, nor shall any single or partial exercise of
any right hereunder or under any Transaction Document preclude any other or further exercise thereof or the exercise of any other
right or remedy. The rights and remedies of the Collateral Agent and the Buyers provided herein and in the other Transaction Documents
are cumulative and are in addition to, and not exclusive of, any rights or remedies provided by law. The rights and remedies of
the Collateral Agent and the Buyers under any Transaction Document against any party thereto are not conditional or contingent
on any attempt by the Collateral Agent or any Buyer to exercise any of their respective rights or remedies under any other Transaction
Document against such party or against any other Person.

 

(d)
Any provision of this Guaranty that is prohibited or unenforceable in any jurisdiction shall, as to such jurisdiction, be
ineffective to the extent of such prohibition or unenforceability without invalidating the remaining portions hereof or affecting
the validity or enforceability of such provision in any other jurisdiction.

 

(e)
This Guaranty is a continuing guaranty and shall (i) remain in full force and effect until Payment in Full of the Guaranteed
Obligations (other than inchoate indemnity obligations) and shall not terminate for any reason prior to the respective Maturity
Date of each Note (other than Payment in Full of the Guaranteed Obligations) and (ii) be binding upon each Guarantor and its respective
successors and assigns. This Guaranty shall inure, together with all rights and remedies of the Collateral Agent hereunder, to
the benefit of and be enforceable by the Collateral Agent, the Buyers, and their respective successors, and permitted pledgees,
transferees and assigns. Without limiting the generality of the foregoing sentence, the Collateral Agent or any Buyer may pledge,
assign or otherwise transfer all or any portion of its rights and obligations under and subject to the terms of the Securities
Purchase Agreement or any other Transaction Document to any other Person in accordance with the terms thereof, and such other Person
shall thereupon become vested with all the benefits in respect thereof granted to the Collateral Agent or such Buyer (as applicable)
herein or otherwise, in each case as provided in the Securities Purchase Agreement or such Transaction Document. None of the rights
or obligations of any Guarantor hereunder may be assigned or otherwise transferred without the prior written consent of each Buyer.

 

    	 	11	 

     

    

 

(f)
This Guaranty and the other Transaction Documents reflect the entire understanding of the transaction contemplated hereby
and shall not be contradicted or qualified by any other agreement, oral or written, entered into before the date hereof.

 

(g)
Section headings herein are included for convenience of reference only and shall not constitute a part of this Guaranty
for any other purpose.

 

Section
15.  Currency Indemnity.

 

If, for the purpose of
obtaining or enforcing judgment against Guarantor in any court in any jurisdiction, it becomes necessary to convert into any other
currency (such other currency being hereinafter in this Section 15 referred to as the “Judgment Currency”)
an amount due under this Guaranty in any currency (the “Obligation Currency”) other than the Judgment Currency,
the conversion shall be made at the rate of exchange prevailing on the Business Day immediately preceding (a) the date of actual
payment of the amount due, in the case of any proceeding in the courts of courts of the jurisdiction that will give effect to such
conversion being made on such date, or (b) the date on which the judgment is given, in the case of any proceeding in the courts
of any other jurisdiction (the applicable date as of which such conversion is made pursuant to this Section 15 being hereinafter
in this Section 15 referred to as the “Judgment Conversion Date”).

 

If, in the case of any
proceeding in the court of any jurisdiction referred to in the preceding paragraph, there is a change in the rate of exchange prevailing
between the Judgment Conversion Date and the date of actual receipt of the amount due in immediately available funds, the Guarantors
shall pay such additional amount (if any, but in any event not a lesser amount) as may be necessary to ensure that the amount actually
received in the Judgment Currency, when converted at the rate of exchange prevailing on the date of payment, will produce the amount
of the Obligation Currency which could have been purchased with the amount of’ the Judgment Currency stipulated in the judgment
or judicial order at the rate of exchange prevailing on the Judgment Conversion Date. Any amount due from the Guarantors under
this Section 15 shall be due as a separate debt and shall not be affected by judgment being obtained for any other amounts
due under or in respect of this Guaranty.

 

[REMAINDER
OF THIS PAGE INTENTIONALLY LEFT BLANK]

 

    	 	12	 

     

    

 

IN WITNESS WHEREOF, each
Guarantor has caused this Guaranty to be executed by its respective duly authorized officer, as of the date first above written.

 

	 	GUARANTORS:
	 	 	 
	 	AKERNA SERVICES LLC
	 	 	 
	 	By:	 
	 	 	Name: Jessica Billingsley
	 	 	Title: Chief Executive Officer
	 	 	 
	 	MJ FREEWAY LLC
	 	 	 
	 	By:	 
	 	 	Name: Jessica Billingsley
	 	 	Title: Chief Executive Officer

 

[Signatures continue on following
page]

 

     

     

    

 

	ACCEPTED BY:	 
	 	 	 
	HT INVESTMENTS MA LLC,
 as Collateral Agent	 
	 	 	 
	By:	 	 
	 	Name:	 
	 	Title:Exhibit 10.5

 

VOTING AGREEMENT

 

VOTING AGREEMENT, dated
as of June __, 2020 (this “Agreement”), by and between Akerna Corp., a Delaware corporation with offices located
at 1630 Welton Street, Denver, Colorado 80202 (the “Company”) and [     ] (the “Stockholder”).

 

WHEREAS, the Company
and certain investors (each, an “Investor”, and collectively, the “Investors”) have entered
into a Securities Purchase Agreement, dated as of June __, 2020 (the “Securities Purchase Agreement”), pursuant
to which, among other things, the Company has agreed to issue and sell to the Investors and the Investors have, severally but not
jointly, agreed to purchase certain senior secured convertible notes of the Company (the “Notes”), which will
be convertible into shares of the Company’s common stock, $0.0001 par value per share (the “Common Stock”, as
converted, the “Conversion Shares”), in accordance with the terms of the Notes;

 

WHEREAS, as of the date
hereof, the Stockholder owns shares of Common Stock (the “Stockholder Shares”), which represent (i) approximately
[%] of the total issued and outstanding Common Stock of the Company, and (ii) approximately [%] of the total voting power of
the Company; and

 

WHEREAS, as a condition
to the willingness of each Investor to enter into the Securities Purchase Agreement and to consummate the transactions contemplated
thereby (collectively, the “Transaction”), the Investors have required that the Stockholder agree, and in order
to induce each Investor to enter into the Securities Purchase Agreement, the Stockholder has agreed, to enter into this Agreement
with respect to all the Stockholder Shares now owned and which may hereafter be acquired by the Stockholder and any other securities
of the Company (the “Other Securities”, and together with the Stockholder Shares, the “Stockholder
Securities”), if any, which Stockholder is currently entitled to vote, or after the date hereof becomes entitled to vote,
at any meeting of the stockholders of the Company.

 

NOW, THEREFORE, in consideration
of the foregoing and the mutual covenants and agreements contained herein, and intending to be legally bound hereby, the parties
hereto hereby agree as follows:

 

ARTICLE I

VOTING AGREEMENT OF THE STOCKHOLDER

 

SECTION 1.01. Voting
Agreement. Subject to the last sentence of this Section 1.01, the Stockholder hereby agrees that at any meeting of the
stockholders of the Company, however called, and in any action by written consent of the Company’s stockholders, the Stockholder
shall vote the Stockholder Securities, which Stockholder is currently entitled to vote, or after the date hereof becomes entitled
to vote, at any meeting of the stockholders of the Company: (a) in favor of the Stockholder Approval (as defined in the Securities
Purchase Agreement) and the Stockholder Resolutions (as defined in the Securities Purchase Agreement), in each case, as described
in Section 4(cc) of the Securities Purchase Agreement; and (b) against any proposal or any other corporate action or agreement
that would result in a breach of any covenant, representation or warranty or any other obligation or agreement of the Company under
the Transaction Documents (as defined in the Securities Purchase Agreement) or which could result in any of the conditions to the
Company’s obligations under the Transaction Documents not being fulfilled. The Stockholder acknowledges receipt and review of a
copy of the Securities Purchase Agreement and the other Transaction Documents. The obligations of the Stockholder under this Section
1.01 shall terminate immediately following the occurrence of the Stockholder Approval.

 

     

     

    

 

ARTICLE II

REPRESENTATIONS AND WARRANTIES OF THE STOCKHOLDER

 

The Stockholder hereby
represents and warrants to the Company and each of the Investors as follows:

 

SECTION 2.01. Authority
Relative to this Agreement. The Stockholder has all requisite power and authority to execute and deliver this Agreement, to
perform its obligations hereunder and to consummate the transactions contemplated hereby. This Agreement has been duly executed
and delivered by the Stockholder and constitutes a legal, valid and binding obligation of the Stockholder, enforceable against
the Stockholder in accordance with its terms, except (a) as such enforceability may be limited by applicable bankruptcy, insolvency,
reorganization, fraudulent conveyance, moratorium or similar laws now or hereafter in effect relating to, or affecting generally,
the enforcement of creditors’ and other obligees’ rights and (b) where the remedy of specific performance or other
forms of equitable relief may be subject to certain equitable defenses and principles and to the discretion of the court before
which the proceeding may be brought.

 

SECTION 2.02. No Conflict.
(a) The execution and delivery of this Agreement by the Stockholder does not, and the performance of this Agreement by the Stockholder
shall not, (i) conflict with or violate any federal, state or local law, statute, ordinance, rule, regulation, order, judgment
or decree applicable to the Stockholder or by which the Stockholder Securities owned by the Stockholder are bound or affected or
(ii) result in any breach of or constitute a default (or an event that with notice or lapse of time or both would become a default)
under, or give to others any rights of termination, amendment, acceleration or cancellation of, or result in the creation of a
lien or encumbrance on any of the Stockholder Securities owned by the Stockholder pursuant to, any note, bond, mortgage, indenture,
contract, agreement, lease, license, permit, franchise or other instrument or obligation to which the Stockholder is a party or
by which the Stockholder or the Stockholder Securities owned by the Stockholder is bound.

 

(b) The
execution and delivery of this Agreement by the Stockholder does not, and the performance of this Agreement by the Stockholder
shall not, require any consent, approval, authorization or permit of, or filing with or notification to, any governmental entity
by the Stockholder.

 

SECTION 2.03. Title
to the Stock. As of the date hereof, the Stockholder is the owner of [     ] shares of Common Stock, entitled to vote, without
restriction, on all matters brought before holders of capital stock of the Company, which shares of Common Stock represent on the
date hereof approximately [     ]% of the outstanding stock and approximately [     ]% of the voting power of the Company. Such shares
of Common Stock are all the securities of the Company owned, either of record or beneficially, by the Stockholder. Such Common
Stock is owned free and clear of all Encumbrances (as defined below). The Stockholder has not appointed or granted any proxy, which
appointment or grant is still effective, with respect to the Common Stock or Other Securities owned by the Stockholder.

 

    -2-

     

    

 

ARTICLE III

COVENANTS

 

SECTION 3.01. Encumbrance
of Stock. The Stockholder hereby covenants and agrees that the Stockholder shall not grant a proxy or power of attorney with
respect to, or create or permit to exist any security interest, lien, claim, pledge, option, right of first refusal, agreement,
or limitation on the Stockholder’s voting rights, charge or other encumbrance of any nature whatsoever (“Encumbrance”)
with respect to the Stockholder Securities, directly or indirectly, or initiate, solicit or encourage any person to take actions
which could reasonably be expected to lead to the occurrence of any of the foregoing.

 

SECTION 3.02. Company
Cooperation. The Company hereby covenants and agrees that it will not, and the Stockholder irrevocably and unconditionally
acknowledges and agrees that the Company will not (and waives any rights against the Company in relation thereto), recognize any
Encumbrance or agreement (other than this Agreement) on any of the Stockholder Securities subject to this Agreement.

 

ARTICLE IV

MISCELLANEOUS

 

SECTION 4.01. Further
Assurances. The Stockholder shall execute and deliver such further documents and instruments and take all further action as
may be reasonably necessary in order to consummate the transactions contemplated hereby.

 

SECTION 4.02. Specific
Performance. The parties hereto agree that irreparable damage would occur in the event any provision of this Agreement was
not performed in accordance with the terms hereof and that any Investor (without being joined by any other Investor) shall be entitled
to specific performance of the terms hereof, in addition to any other remedy at law or in equity. Any Investor shall be entitled
to its reasonable attorneys’ fees in any action brought to enforce this Agreement in which it is the prevailing party.

 

SECTION 4.03. Entire
Agreement. This Agreement constitutes the entire agreement between the Company and the Stockholder (other than the Securities
Purchase Agreement and the other Transaction Documents) with respect to the subject matter hereof and supersedes all prior agreements
and understandings, both written and oral, among the Company and the Stockholder with respect to the subject matter hereof.

 

SECTION 4.04. Amendment.
This Agreement may not be amended except by an instrument in writing signed by the parties hereto.

 

SECTION 4.05. Severability.
If any term or other provision of this Agreement is invalid, illegal or incapable of being enforced by any rule of law, or public
policy, all other conditions and provisions of this Agreement shall nevertheless remain in full force and effect so long as the
economic or legal substance of this Agreement is not affected in any manner materially adverse to any party. Upon such determination
that any term or other provision is invalid, illegal or incapable of being enforced, the parties hereto shall negotiate in good
faith to modify this Agreement so as to effect the original intent of the parties as closely as possible in a mutually acceptable
manner in order that the terms of this Agreement remain as originally contemplated to the fullest extent possible.

 

    -3-

     

    

 

SECTION 4.06. Governing
Law. All questions concerning the construction, validity, enforcement and interpretation of this Agreement shall be governed
by the internal laws of the State of Delaware, without giving effect to any choice of law or conflict of law provision or rule
(whether of the State of Delaware or any other jurisdictions) that would cause the application of the laws of any jurisdictions
other than the State of Delaware. The Company hereby irrevocably submits to the exclusive jurisdiction of the state and federal
courts sitting in the Borough of Manhattan in the City of New York, New York, for the adjudication of any dispute hereunder or
in connection herewith or under any of the other Transaction Documents or with any transaction contemplated hereby or thereby,
and hereby irrevocably waives, and agrees not to assert in any suit, action or proceeding, any claim that it is not personally
subject to the jurisdiction of any such court, that such suit, action or proceeding is brought in an inconvenient forum or that
the venue of such suit, action or proceeding is improper. The parties consent to the jurisdiction and venue of the foregoing courts
and consent that any process or notice of motion or other application to any of said courts or a judge thereof may be served inside
or outside the State of New York or the Southern District of New York by registered mail, return receipt requested, directed to
the party being served at its address set forth on the signature ages to this Agreement (and service so made shall be deemed complete
three (3) days after the same has been posted as aforesaid) or by personal service or in such other manner as may be permissible
under the rules of said courts. Each of the Company and the Stockholder irrevocably waives, to the fullest extent permitted by
law, any objection which it may now or hereafter have to the laying of the venue of any such suit, action, or proceeding brought
in such a court and any claim that suit, action, or proceeding has been brought in an inconvenient forum. EACH PARTY HEREBY
IRREVOCABLY WAIVES ANY RIGHT IT MAY HAVE, AND AGREES NOT TO REQUEST, A JURY TRIAL FOR THE ADJUDICATION OF ANY DISPUTE HEREUNDER
OR IN CONNECTION WITH OR ARISING OUT OF THIS AGREEMENT OR ANY TRANSACTION CONTEMPLATED HEREBY.

 

SECTION 4.07. Termination.
This Agreement shall automatically terminate immediately following the occurrence of the Shareholder Approval.

 

[The remainder of the page is intentionally
left blank]

 

    -4-

     

    

 

IN WITNESS WHEREOF, the
Stockholder and the Company have duly executed this Voting Agreement as of the date first written above.

 

	 	THE COMPANY:
	 	 
	 	AKERNA CORP.
	 	 	 	 
	 	By:	                         
	 	 	Name:	     
	 	 	Title:	
	 	 	 	 
	 	Address:		1630 Welton Street,
	 	 	 	Denver, Colorado 8020
	 	 	 	 
	 	STOCKHOLDER:
	 	 	 	
	 	 
	 			
	 	By:	       
	 	 	Name:	
	 	 	Title:	
	 	 	 	 
	 	Address:

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