Document:

Exhibit 4.1

 

SECOND AMENDMENT

TO AMENDED AND RESTATED MEMBER CONTROL
AGREEMENT

OF TWIN CITIES POWER HOLDINGS, L.L.C.

 

This Second Amendment to Amended and Restated
Member Control Agreement (“Second Amendment”) dated August 28th, 2013 is to be effective as of the 28th
day of June, 2013 by and among Timothy S. Krieger (“Krieger”) and Summer Enterprises, L.L.C., a Minnesota Limited Liability
Company (“Summer”) who are all of the members of Twin Cities Power Holdings, L.L.C., a Minnesota Limited Liability
Company (the “Company”). Krieger, Summer and the Company are jointly referred to as Parties (“Parties”).

 

R E C I T A L S

 

		A.	The Company entered into an Amended and Restated Member Control Agreement dated as of July 18th, 2012 (the “Agreement”)
and a First Amendment to Amended and Restated Member Control Agreement dated July 30th, 2013 (“First Amendment”).

 

		B.	The Parties now desire to amend the Agreement and the First Amendment to delete all references to the Hanson Preferred Units
and substitute in its place a Certificate of Designation of Series A Preferred Units of the Company.

 

THE PARTIES HEREBY AGREE AS FOLLOWS:

 

		1.	The terms and conditions of that certain Certificate of Designation of Series A Preferred Units of Twin Cities Power Holdings,
L.L.C., are hereby incorporated into the Agreement and First Amendment and the Agreement and First Amendment shall be deemed to
have been modified to incorporate the rights and preferences of the Certificate of Designation of Series A Preferred Units by this
Second Amendment. A copy of the Certificate of Designation of Series A Preferred Units of Twin Cities Power Holdings, LLC is marked
as Exhibit “A”, attached hereto and incorporated herein by reference.

 

		2.	Summer Enterprises, L.L.C. does herein agree to be bound by the terms of the Amended and Restated Member Control Agreement
dated July 18, 2012 as amended by the First and Second Amendments.

 

		3.	All other terms and conditions of the Amended and Restated Member Control Agreement of Twin Cities Power Holdings, L.L.C. as
amended by the First and Second Amendments shall remain in full force and effect except as herein before amended.

 

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IN WITNESS WHEREOF, the undersigned
have executed this Second Amendment as of the date first written above.

 

	MEMBERS:	
        COMPANY:

         

	
         

        /s/ Timothy S. Krieger

        Timothy S. Krieger
	
        TWIN CITIES POWER HOLDINGS, L.L.C.

        /s/ Timothy S. Krieger

        By: Timothy S. Krieger

        Its: President/CEO

	
        SUMMER ENTERPRISES, L.L.C.

        /s/ Timothy S. Krieger

        By: Timothy S. Krieger

        Its: President/CEO
	 

 

 

 

 

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EXHIBIT A

 

CERTIFICATE OF DESIGNATION

OF

SERIES A PREFERRED UNITS

OF

TWIN CITIES POWER HOLDINGS, LLC

 

WHEREAS, TWIN CITIES POWER HOLDINGS, LLC
is a Minnesota limited liability company organized under Chapter 322B, Minnesota Statutes (the “Company”);

 

WHEREAS, pursuant to Article II, paragraph
2.02 of its Articles of Organization dated December 30, 2009 (the “Articles”) and its Amended and Restated Member Control
Agreement dated July 18, 2012, as amended by that certain First Amendment dated July 30th, 2013, the Company is authorized
to establish by resolution different classes and/or series of membership interests and may fix the rights and preferences of said
membership interests in any class or series.

 

WHEREAS, the Board of Governors has resolved
that the Company issue “Common Units” and one or more classes of Preferred Units to be designated, respectively, as
“Common Units” and “Preferred Units”;

 

NOW, THEREFORE, the Board of Governors
hereby establishes the rights, preferences, and restrictions of the Company’s Series A Preferred Units as follows:

 

1. Designation; Authorization; Liquidation
Preference; Parity.

 

(a) Designation. A series of the
Company’s Preferred Units shall be designated as its Series A Preferred Units (the “Preferred Units” or the “Units”).

 

(b) Authorization. The number of
authorized units constituting the Preferred Units is 496.

 

(c) Liquidation Preference. The
Preferred Units shall have a preference upon distribution in liquidation of $5,535.00 per Unit plus distributions accrued and interest
thereon at the rate of 20% per annum from the date accrued (the “Liquidation Preference”).

 

(d) Parity. The Preferred Units
shall be senior to the Company’s Common Units and rank on parity with all other classes and series of preferred equity of
the Company now or hereafter authorized, issued, or outstanding, other than any classes or series ranking senior to the Preferred
Units as to distribution rights and rights upon liquidation, winding up, or dissolution of the Company, provided that the holders
of the Preferred Units so permit. The Preferred Units shall be junior to all outstanding debt of the Company, whether senior or
subordinated. 

 

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2. Distributions.

 

(a) Payment. The holders of record
of Preferred Units shall be entitled to receive, when, as, and if declared by the Board of Governors, out of funds legally available
therefor, non-cumulative cash distributions at the rate of $92.25 per unit per month (the “Distribution Rate”). The
distributions shall be payable monthly in arrears on the first day of each month, beginning August 1, 2013 or, if any such day
is a non-business day, on the next business day (each of such dates, a “Distribution Payment Date” and each preceding
monthly period being a “Distribution Period”). Each declared distribution shall be payable to holders of record as
they appear on the Unit Register of the Company at the close of business on the Record Dates. The Record Dates shall be set as
of the first day of each Distribution Period.

 

(b) Participation. The Preferred
Units shall not participate in distributions with the Common Units.

 

(c) Noncumulative. Distributions
on the Preferred Units shall be noncumulative. If the Board of Governors fails to declare a distribution payable on a Distribution
Payment Date in respect of the Preferred Units due to a lack of legally available funds or the need to meet debt obligations, then
the right of holders of Preferred Units to receive a distribution in respect of the Distribution Period ending on such Distribution
Payment Date will be lost and the Company will have no obligation to pay the distribution accrued for such Distribution Period
or to pay any interest thereon, whether or not distributions on the Preferred Units are declared for any future Distribution Period,
provided that the provisions of this paragraph shall not affect the determination of the amount of the Liquidation Preference or
the priority of the payment of distributions, or the amount thereof, as provided in Section 3(e).

 

(d) Computation. The amount of distributions
payable on Preferred Units for each full Distribution Period shall be computed by multiplying the number of Preferred Units outstanding
by the Distribution Rate. The amount of any distribution payable per Unit for any period shorter than a full Distribution Period
shall be computed by multiplying the Distribution Rate by 12, dividing by a 360-day year, and multiplying by the actual number
of days elapsed in such period.

 

(e) Priority.

 

(i) Except for distributions to holders
of the Common Units in lieu of income taxes as described in the Company’s Member Control Agreement, as amended from time
to time (“Tax Distributions”), no distributions shall be declared, paid, or set apart for payment on Preferred Units
of any series ranking as to distributions on a parity with or junior to the Preferred Units for any period unless the full distribution
accrued on the Preferred Units has been, or contemporaneously is, declared and paid for all prior Distribution Periods from the
date of the issuance of the Preferred Units and a sum sufficient for the payment thereof set apart for such payment.

 

When distributions are not paid in full
(or declared and a sum sufficient for such full payment is not so set apart) upon the Preferred Units and any other Preferred Units
ranking on a parity as to distributions with the Preferred Units, all distributions declared upon the Preferred Units and any other
series of Preferred Units ranking on a parity as to distributions shall be declared pro rata, so that the amount of distributions
declared per Unit on Preferred Units and such other series of Preferred Units shall in all cases bear to each other the same ratio
that accrued distributions for the then-current Distribution Period on the Preferred Units and accrued distributions, including
required or permitted accumulations, if any, of such other series of Preferred Unit, bear to each other.

 

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(ii) So long as any Preferred Units are
outstanding and full distributions on the Preferred Units for all past distribution periods have not been paid, no distribution,
other than: (A) Tax Distributions in cash as described in Section 2.(d)(i); (B) distributions paid in additional Preferred Units;
(C) distributions of options, warrants, or rights to subscribe for or purchase Common Units or any other Preferred Units ranking
junior to the Preferred Units as to distributions or upon liquidation, shall be declared or paid or set aside for payment or other
distribution declared or made upon the Common Units or upon any other Units of the Company ranking junior to the Preferred Units
as to distributions or upon liquidation, nor shall any Common Units or any other Units of the Company ranking junior to or on a
parity with the Preferred Units as to distributions or upon liquidation be redeemed, purchased, or otherwise acquired for any consideration
(or any moneys be paid to or made available for a sinking fund for the redemption of any such Units) by the Company otherwise than
pursuant to a pro rata offer to purchase or a concurrent redemption of all, or a pro rata portion, of the outstanding
Preferred Units and any other Units on a parity with Preferred Units (except by conversion into or exchange for Units of the Company
ranking junior to the Preferred Units as to distributions and upon liquidation) unless and until the Company shall have paid full
distributions on the Preferred Units for all prior Distribution Periods from the date of the issuance of the Preferred Units.

 

3. Voting. So long as any Preferred
Units are outstanding, in addition to any other vote or consent of members of the Company required by law or by the Articles, the
consent of the holders of at least a majority of the Preferred Units, acting as a single class, given in person or by proxy, either
in writing without a meeting or by vote at any meeting called for the purpose, shall be necessary for effecting:

 

(a) Any amendment, alteration, or
repeal of any of the provisions of the Articles that affects adversely the voting powers, rights, or preferences of the holders
of the Preferred Units, provided that the amendment of the provisions of the Articles so as to authorize or create, or to increase
the authorized amount of, any Units of any class ranking junior to or on a parity with the Preferred Units shall not be deemed
to affect adversely the voting powers, rights, or preferences of the holders of the Preferred Units;

 

(b) The authorization or creation
of, or the increase in the authorized amount of, any Units of any class or any security convertible into Units of a class ranking
prior to the Preferred Units in the distribution of assets on any liquidation, dissolution, conservatorship, receivership, or winding
up of the Company, or in the payment of distributions; or

 

(c) The merger or consolidation
of the Company with or into any other entity, unless the Preferred Units or an equivalent class of securities remain outstanding
after the merger or consolidation and the resulting entity will thereafter have no class of Units and no other securities either
authorized or outstanding ranking prior to the Preferred Units in the distribution of its assets on liquidation, dissolution or
winding up or in the payment of distributions, provided that no such consent of the holders of Preferred Units shall be required
if, at or prior to the time when such amendment, alteration or repeal is to take effect or when the issuance of any such prior
Units or convertible security is to be made, or when such consolidation or merger, purchase or redemption is to take effect, as
the case may be, provision is made for the redemption of all Preferred Units at the time outstanding.

 

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4. Redemption. The Preferred Units
shall not be redeemable, except as set forth in Section 3(c).

 

5. Liquidation Rights.

 

(a) Upon the dissolution, liquidation
or winding up of the Company, the holders of the Preferred Units shall be entitled to receive and to be paid out of the assets
of the Company available for distribution to its members, before any payment or distribution shall be made on the Common Units
or on any other class of Units ranking junior to the Preferred Units upon liquidation, the amount of the Liquidation Preference.

 

(b) The sale of all or substantially
all the property or business of the Company, or the merger or consolidation of the Company into or with any other corporation or
the merger or consolidation of any other corporation into or with the Company shall be deemed to be a dissolution, liquidation,
or winding up, voluntary or involuntary, for the purposes of this Section 5.

 

(c) After the payment to the holders
of the Preferred Units of the full preferential amounts provided for in this Section 5, the holders of Preferred Units as such
shall have no right or claim to any of the remaining assets of the Company.

 

(d) In the event the assets of the
Company available for distribution to the holders of Preferred Units upon any dissolution, liquidation, or winding up of the Company,
whether voluntary or involuntary, shall be insufficient to pay in full all amounts to which such holders are entitled pursuant
hereto, no such distribution shall be made on account of any other class or series of Preferred Units ranking on a parity with
the Preferred Units upon such dissolution, liquidation, or winding up unless proportionate distributive amounts shall be paid on
account of the Preferred Units, ratably, in proportion to the full distributable amounts for which holders of all such parity Units
are respectively entitled upon such dissolution, liquidation, or winding up.

 

(e) Subject to the rights of the
holders of Units of any series or class or classes of Units ranking on a parity with the Preferred Units upon liquidation, dissolution,
or winding up of the Company, after payment shall have been made in full to the holders of the Preferred Units as provided herein,
but not prior thereto, any other series or class or classes of Units ranking junior to the Preferred Units upon liquidation, subject
to the respective terms and provisions applying thereto, shall be entitled to receive any and all assets remaining to be paid or
distributed, and the holders of the Preferred Units shall not be entitled to share therein.

 

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6. Ranking. A Unit of any class
of the Company shall be deemed to rank:

 

(a) Prior to the Preferred Units,
if the holders of such class or classes shall be entitled to the receipt of distributions or of amounts distributable upon dissolution,
liquidation or winding up of the Company, as the case may be, in preference or priority to the holders of Preferred Units;

 

(b) On a parity with the Preferred
Units, if the holders of such Units shall be entitled to the receipt of distributions or of amounts distributable upon dissolution,
liquidation or winding up of the Company, in proportion to their respective distribution rates or liquidation prices, without preference
or priority, one over the other, as between the holders of such Units and the holders of the Preferred Units; and

 

(c) Junior to the Preferred Units,
if such class shall be Common Units or if the holders of the Preferred Units shall be entitled to receipt of distributions or of
amounts distributable upon dissolution, liquidation, or winding up of the Company, as the case may be, in preference or priority
to the holders of Units of such class or classes.

 

7. Conversion and Cancellation.
The Company’s existing class of preferred units is hereby converted, on a one-for-one basis, into Preferred Units and the
existing class of preferred units is, upon such conversion, cancelled.

 

The Preferred Units are not convertible
into Common Units.

 

    	7Exhibit 10.1

 

GUARANTEE

 

GUARANTEE, dated as
of August 12, 2013, by TWIN CITIES POWER HOLDINGS, LLC, a Minnesota limited liability company, ("Guarantor"), in favor
of NOBLE AMERICAS ENERGY SOLUTIONS LLC (the "Counterparty").

 

1. Guarantee. To
induce the Counterparty to enter into transactions (the "Transactions") with TOWN SQUARE ENERGY, LLC (“Affiliate”),
Guarantor guarantees to the Counterparty and its successors, endorsees and assigns the prompt payment when due, subject to any
applicable grace period, of all present and future payment obligations of Affiliate to the Counterparty arising out of Transactions
(the "Obligations"). The maximum aggregate liability of Guarantor under the Guarantee is limited to the amount of ONE
MILLION U.S. DOLLARS (U.S. $1,000,000.00) plus costs and expenses, including reasonable attorney’s fees, incurred in enforcing
this Guarantee against the Guarantor.

 

2. Nature of
Guarantee. Guarantor’s obligations hereunder shall not be affected by the existence, validity, enforceability,
perfection, or extent of any collateral therefor or by any other circumstance relating to the Obligations that might
otherwise constitute a legal or equitable discharge of or defense to Guarantor not available to Affiliate. This is a
guarantee of payment and not collection. Guarantor agrees that the Counterparty may resort to Guarantor for payment of any of
the Obligations whether or not the Counterparty shall have resorted to any collateral therefor or shall have proceeded
against Affiliate or any other obligor principally or secondarily obligated with respect to any of the Obligations. The
Counterparty shall not be obligated to file any claim relating to the Obligations in the event that Affiliate becomes subject
to a bankruptcy, reorganization or similar proceeding, and the failure of the Counterparty to so file shall not affect the
Guarantor’s obligations hereunder. If any payment to the Counterparty in respect of any Obligations is rescinded or
must otherwise be returned for any reason whatsoever, Guarantor shall remain liable hereunder with respect to such
Obligations as if such payment had not been made. Guarantor reserves the right to (a) set-off against any payment owing
hereunder any amounts owing by the Counterparty to Affiliate and (b) assert defenses which Affiliate may have to payment of
any Obligations other than defenses arising from the bankruptcy or insolvency of Affiliate and other defenses expressly
waived hereby.

 

3. Changes in
Obligations, Collateral therefor and Agreements Relating thereto; Waiver of Certain Notices. Guarantor agrees that the
Counterparty may at any time and from time to time, either before or after the maturity thereof, without notice to or further
consent of such Guarantor, extend the time of payment of, exchange or surrender any collateral for, or renew any of the
Obligations, and may also make any agreement with Affiliate or with any other party to or person liable on any of the
Obligations or interested therein, for the extension, renewal, payment, compromise, discharge or release thereof, in whole or
in part, or for any modification of the terms thereof or of any agreement between the Counterparty and Affiliate or any such
other party or person, without in any way impairing or affecting this Guarantee. Guarantor waives notice of the acceptance of
this Guarantee and of the Obligations, presentment, demand for payment, notice of dishonor and protest. Without limiting the
foregoing, in accordance with Section 2856 of the California Civil Code, Guarantor waives any and all other rights and
defenses available to Guarantor by reason of Sections 2787 to 2855, inclusive, 2899 and 3433 of the California Civil Code,
including without limitation any and all rights or defenses Guarantor may have by reason of protection afforded to Affiliate
with respect to any of the Obligations, or to any other guarantor of any of the Obligations with respect to any of such
guarantor’s obligations under its guaranty, in each case pursuant to the laws of the state of California limiting or
discharging the Affiliate’s or such guarantor’s obligations.

 

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4. Expenses. Guarantor
agrees to pay on demand all fees and out of pocket expenses (including, without limitation, the reasonably allocated fees of
in-house counsel and other reasonable fees of the Counterparty's counsel, and reasonable expenses of each of the foregoing)
in any way relating to the enforcement or protection of the rights of the Counterparty hereunder; provided, that Guarantor
shall not be liable for any expenses of the Counterparty if no payment under this Guarantee is due.

 

5. Subrogation. Upon
payment of any of the Obligations, Guarantor shall be subrogated to the rights of the Counterparty against Affiliate with
respect to such Obligations, and the Counterparty agrees to take at the Guarantor’s expense such steps as Guarantor may
reasonably request to implement such subrogation.

 

6. No Waiver;
Cumulative Rights. No failure on the part of the Counterparty to exercise, and no delay in exercising, any right, remedy
or power hereunder shall operate as a waiver thereof, nor shall any single or partial exercise by the Counterparty of any
right, remedy or power hereunder preclude any other or future exercise of any right, remedy or power. Each and every right,
remedy and power hereby granted to the Counterparty or allowed it by law or other agreement shall be cumulative and not
exclusive of any other, and may be exercised by the Counterparty at any time or from time to time.

 

7. Assignment.
This Guarantee may be freely assigned by Counterparty without the Guarantor’s consent. Neither this Guarantee nor any
rights, interests or obligations hereunder may be assigned by the Guarantor to any other person (except by operation of law)
without the prior written consent of the Counterparty.

 

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8. Notices. All
notices or demands on Guarantor shall be deemed effective when received, shall be in writing and shall be delivered by hand
or by registered mail, or by facsimile transmission promptly confirmed by registered mail, addressed to Guarantor at:

 

Twin Cities Power Holdings,
LLC

16233 Kenyon Avenue, Suite
210

Lakeville, MN 55044

Keith W. Sperbeck

(952) 241-3103

952-898-3571

ksperbeck@twincitiespower.com

 

or to such other address or fax number as Guarantor
shall have notified the Counterparty in a written notice delivered to the Counterparty.

 

9. Continuing
Guarantee. Subject to the provisions of Section 1 and 10 hereof, this Guarantee shall become and remain in full force and
effect and shall be binding on Guarantor, its successors and assigns until all of the Obligations have been satisfied in
full.

 

10. Termination.
Upon not less than thirty (30) days prior written notice thereof to the Counterparty, Guarantor may terminate this Guarantee insofar
as it would otherwise relate (but for such termination) to Transactions entered into after the effectiveness of such termination.
Such termination shall not affect the obligations hereunder of Guarantor in respect to the Transactions entered into before such
effectiveness as to which this Guarantee shall, in all respects, remain in full force and effect.

 

11. Governing Law.
This Guarantee shall in all respects be governed by and construed in accordance with the laws of the State of California
without regard to principles of conflicts of laws.

 

12. Execution in
Counterparts. This Guarantee may be executed in counterparts, each of which when so executed shall be deemed to be an
original and all of which taken together shall constitute one and the same agreement.

 

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13. Entire
Agreement. This Guarantee constitutes the entire agreement and supersedes all prior agreements and understandings, both
written and oral, between Guarantor and Counterparty with respect to the subject matter hereof. Neither this Guarantee nor
any of the terms hereof may be terminated, amended, supplemented, waived or modified orally, except by an instrument in
writing signed by the party against which the enforcement of this termination, amendment or supplement, waiver or
modification shall be sought.

 

 

 

IN WITNESS WHEREOF, this Guarantee
has been duly executed and delivered by Guarantor to the Counterparty as of the date first above written.

 

 

 

GUARANTOR

 

TWIN CITIES POWER HOLDINGS, LLC

 

 

 

 

By: /s/ Timothy Krieger

 

Printed Name:  Timothy Krieger

 

Title: CEO/President

 

 

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