DE MUNIZ, J.
Plaintiff's — Synectic Ventures I, LLC, Synectic Ventures II, LLC, and Synectic Ventures III, LLC — entered into a loan agreement regarding money that they had loaned to defendant EVI Corporation. The loan agreement provided that the loan, which was secured by a security interest in essentially all of defendant's property, would be converted to equity ownership in defendant, if defendant obtained additional financing by a certain date. Shortly before that deadline, the managing member of plaintiffs — who was also chairman of the board and treasurer of defendant and financially interested in defendant — entered into an agreement purporting to extend the loan period by an additional year. During the extension period, defendant obtained the additional financing and converted the debt to equity. Plaintiffs filed an action against defendant, asserting (among other things) that they were not bound by the extension because the managing member had had a conflict of interest and defendant knew of the conflict. The trial court rejected that argument and granted summary judgment for defendant. The Court of Appeals affirmed. Synectic Ventures I, LLC v. EVI Corp., 241 Or.App. 550, 251 P.3d 216 (2011). On review, we conclude that the trial court erred in granting defendant summary judgment. We therefore reverse the decision of the Court of Appeals and the judgment of the trial court.
As noted, this case is before us on review from a trial court's grant of summary judgment for defendant. Accordingly, we consider the facts, as well as all reasonable inferences from those facts, in the light most favorable to the nonmoving party — in this case, plaintiffs. Loosli v. City of Salem, 345 Or. 303, 306 n. 1, 193 P.3d 623 (2008); see ORCP 47 C (on summary judgment, trial court must determine whether there is no genuine issue of material fact "based upon the record before the court viewed in a manner most favorable to the adverse party").
Plaintiffs are manager-managed limited liability companies (LLCs).
Plaintiffs' operating agreements contained a number of provisions relevant to the scope of Berkman's authority to act on plaintiffs' behalf. Because the scope of that authority is integral to the proper resolution of this case on review, we discuss those provisions in some detail.
First, the operating agreements gave Berkman, as managing member, exclusive control over plaintiffs. Specifically, each operating agreement provided:
Second, the operating agreements indicated that third parties could rely on the representations of the managing member without needing to make further inquiry. Each operating agreement stated:
Finally, the operating agreements allowed each of plaintiff's members to invest in or manage companies in which the plaintiffs themselves invested. Specifically, each operating agreement provided in part:
One of the businesses in which plaintiffs invested was defendant, a company that develops medical devices. At all relevant times, Berkman — the managing member of plaintiffs — was also chairman of the board and treasurer of defendant. In 2004, Berkman also owned a significant number of shares in defendant, which he had pledged as security for personal debts of between $500,000 and $700,000. Berkman also periodically received interest-free loans from defendant.
Before March 2003, plaintiffs had loaned over $3 million to defendant.
Later in 2003, a number of the members of plaintiffs, having become disgruntled with Berkman's management, hired a law firm to represent them. On July 28, 2003, the law firm sent Berkman a letter that (among other things) requested Berkman's voluntary resignation as managing member of plaintiffs. In September 2003 and again in June 2004, Berkman signed letter agreements with those members agreeing not to enter into new obligations on behalf of plaintiffs without getting advance approval by those members. On September 2, 2004, the law firm wrote to Berkman and notified him that he would be removed as managing member as soon as the other members could elect a new managing member.
Beginning September 10, 2004 — less than four months before plaintiffs' loan to defendant matured, and just over one week after learning that he soon would be removed as managing member — Berkman prepared an amendment to the March 2003 loan agreement. The amendment falsely stated that it had been made on August 15, 2004. The amendment primarily extended the maturity date on the loan agreement for an extra year, from December 31, 2004, to December 31, 2005. Berkman participated on both sides of the transaction: On behalf of defendant he signed a consent resolution of defendant's board of directors authorizing the transaction, while on behalf of plaintiffs he signed the amendment itself. If Berkman had not amended the loan agreement to extend the maturity date, then plaintiffs would have been entitled to foreclose on all of defendant's assets after December 31, 2004. Foreclosure would have made defendant's stock worthless, and would have given plaintiffs control of its intellectual property.
Berkman was removed as the managing member in December 2004. By January 2005, the new managing member had been informed about the amendment to the loan agreement that purported to extend the date for defendant to obtain the additional financing. A law firm acting on behalf of the new managing member notified defendant in late August 2005 that the loan amendment was unauthorized and objected to any attempt to convert the loan amount into shares. Notwithstanding that notification, on December 29, 2005 — just before the amended maturity date for the loan expired — defendant received $1 million in additional investment. In accordance with the provision of the loan agreement allowing the loan to be converted to equity, defendant converted the amount of the loan into equity shares. Because the conversion eliminated defendant's security interest in favor of plaintiffs, plaintiffs lost their opportunity to foreclose on defendant's property and were left as minority shareholders in defendant, holding less than five percent of the outstanding stock.
Plaintiffs filed an action against defendant, seeking to recover on the loan agreement and foreclose on the security interest. The complaint was based on defendant not having paid the loan as of the original maturity date, December 31, 2004. In its answer, defendant relied on the loan amendment having extended the maturity date. Defendant asserted that, in accordance with the terms of the amended loan agreement, the loan had been converted into equity.
Subsequently, the parties filed cross-motions for summary judgment. Plaintiffs argued (among other things) that the amendment to the loan agreement was invalid because Berkman had a conflict of interest, the conflict deprived Berkman of authority to execute the loan agreement amendment on behalf of plaintiffs, and defendant knew that Berkman lacked that authority. See ORS 63.140(2)(a) (manager can bind LLC to transactions "unless the manager
The trial court denied plaintiffs' motion for summary judgment and granted defendant's motion. In a letter opinion, the trial court stated that the operating agreements expressly permitted Berkman to enter into transactions on behalf of plaintiffs with a corporation, in which he had invested in or that he was managing. Furthermore, the court held, the operating agreement relieved defendant of any obligation to inquire into Berkman's authority. Finally, the court stated, even if defendant had inquired into Berkman's authority, defendant would have concluded that Berkman had authority to approve the amendment.
Plaintiffs appealed, raising essentially the same arguments that they had in the trial court. The Court of Appeals rejected those arguments and affirmed the trial court ruling. The court noted that, under ORS 63.140(2)(a), an LLC manager can bind the LLC "`unless the manager had no authority to act for the limited liability company in the particular matter and the person with whom the manager was dealing knew or had notice that the manager lacked authority.'" Synectic Ventures, 241 Or.App. at 564, 251 P.3d 216 (quoting ORS 63.140(2)(a)). The Court of Appeals noted that the operating agreements granted Berkman extensive authority as managing member to control plaintiffs, id. at 557-59, 251 P.3d 216, and even if Berkman had breached duties owed to plaintiffs, that did not limit his authority to act on plaintiffs' behalf. According to the Court of Appeals: "[T]here was no operation of law that stripped [Berkman] of his authority to bind plaintiffs in the ordinary course of business." Id. at 565, 251 P.3d 216. Furthermore, the Court of Appeals concluded that section 3.2 of the operating agreements permitted Berkman to engage in transactions in which he had a conflict of interest. Id. at 565-66, 251 P.3d 216. Finally, the court stated that it did not matter whether defendant knew about Berkman's conflict of interest, because (1) the operating agreements allowed third parties to rely on Berkman's authority without making any inquiry, and (2) any inquiry would have led defendant to conclude that Berkman had authority to enter into the amendment. Id. at 565, 251 P.3d 216.
On review, plaintiffs renew their earlier arguments. They contend that the trial court erred in granting summary judgment for defendant because Berkman had a conflict of interest with plaintiffs in dealing with defendant, that that conflict deprived him of authority to amend the loan agreement on behalf of plaintiffs, that defendant knew about the conflict because Berkman was its agent, and therefore plaintiffs are not bound by the amendment. Accordingly, plaintiffs maintain that they are entitled to foreclose on the security interest. For its part, defendant asserts that Berkman had authority to bind plaintiffs to the amendment, that plaintiffs' operating agreements allowed Berkman to do so despite any conflict of interest, and that defendant had a right to rely on Berkman's apparent authority to enter into the amendment. Defendant also maintains that plaintiffs ratified the amendment by their delay in objecting to it, even after Berkman had been removed as managing member.
Because this matter is before us on a grant of summary judgment, we must determine whether, as the trial court concluded, there were no genuine issues of material fact and defendant was entitled to judgment as a matter of law. See ORCP 47 C (stating summary judgment standard). We begin by considering the circumstances under which LLCs such as plaintiffs are bound by the acts of a manager.
By statute, a manager's actions generally bind a manager-managed LLC, unless the manager lacked actual or apparent authority to enter into the transaction and the other party knew or should have known that the manager lacked authority. ORS 63.140 provides (in part) as follows:
ORS 63.140(2)(a) (emphasis added). Plaintiffs assert that both criteria have been met here: that Berkman lacked authority to enter into the amendment to the loan agreement, and that defendant knew or should have known that he lacked authority.
We agree with defendant that Berkman had authority to enter into contracts of this kind, including determining whether to extend the maturity date of loans. ORS 63.140(2)(a) supports that conclusion, and the operating agreements confirm it.
Plaintiffs assert, however, that Berkman did not have authority to enter into this particular transaction (the amendment to the loan agreement) because he had a conflict of interest. We now consider that question.
In the agency context, the term "conflict of interest"
Lindland v. United Business Investments, 298 Or. 318, 322 n. 2, 693 P.2d 20 (1984). If an agent acts for a principal when the agent has a conflict of interest, the agent has breached the duty of loyalty to the principal. Id. at 324, 693 P.2d 20 ("[C]onflict of interest or self-dealing is the breach of duty [of loyalty]." (Emphasis in original.)); see Restatement (Third) of Agency § 8.03 (2006) (duty of loyalty includes duty not to deal with principal either as adverse party or on behalf of adverse party).
An agent ordinarily lacks authority to act on behalf of a principal in a transaction in which the agent has a conflict of interest. As this court explained in Fine v. Harney Co. National Bank, 181 Or. 411, 447-48, 182 P.2d 379 (1947):
(Additional citations omitted.) See State v. Miller, 47 Or. 562, 566, 85 P. 81 (1906) ("It is elementary * * * that an agent cannot bind his principal, even in matters touching his agency, where he is known to be acting for himself, or to have an adverse interest." (Internal quotation marks and citation omitted.))
By statute, however, a manager's duty of loyalty to the LLC does not prohibit self-interested transactions, as long as they are fair to the LLC. See ORS 63.155(9)(b) (making duties of ORS 63.155(2)-(8) applicable to manager of manager-managed LLC); ORS 63.155(6)(a) (member of member-managed LLC may transact business with LLC, provided that the transaction "must be" "[f]air to the limited liability company").
Further elaboration is unnecessary. Berkman's personal interests, and his interests as chairman of the board and treasurer of defendant, conflicted with plaintiffs' interests as to whether the loan agreement should be amended, and there was a question for the factfinder as to whether the amendment was fair to plaintiffs. Accordingly, there was a genuine issue of material fact regarding whether Berkman had a conflict of interest that breached his duty of loyalty in a manner that deprived him of authority to enter into the amendment.
Defendant argues that, regardless, a provision of plaintiffs' operating agreements permitted Berkman to act on behalf of plaintiffs, notwithstanding any conflict of interest. We now turn to that question.
Although an agent ordinarily lacks authority to enter into a transaction in which the agent has a conflict of interest, the principal may authorize the transaction despite the conflict. In the case of LLCs, ORS 63.130 provides, in part:
ORS 63.130(4)(h). See also ORS 63.155(6)(b), (c) (permitting self-interested transactions
Defendant does not assert that a majority of plaintiffs' members formally approved Berkman's conflict of interest in making the amendment, as required by that statute.
Defendant contends that, because Berkman was labeled as "[m]anaging [m]ember" in the operating agreements, Berkman was permitted to act despite the conflict by section 3.2, which applies to "[a]ny [m]ember."
We agree that, at common law, a principal could authorize an agent to engage in a transaction in which the agent has a conflict of interest with the principal. In doing so, however, the authorization must be specific:
Fine, 181 Or. at 448, 182 P.2d 379 (internal quotation marks and citation omitted). In the LLC context, the legislature has imposed a similar requirement. ORS 63.155 provides in part:
(Emphasis added.)
As we will explain, we conclude that section 3.2 of the operating agreements did not specifically allow Berkman to engage in transactions where he had a conflict of interest that breached his duty of loyalty. Section 3.2 allows only ordinary members, who are essentially passive investors in the LLC, to invest in or manage other corporations. It does not specifically allow the managing member, who essentially controls all aspects of LLC operations, to engage in transactions in which the manager has a conflict of interest.
In manager-managed LLCs, substantial differences exist between the powers and duties of a manager and the powers and duties of a member. By statute, the manager essentially has exclusive authority to run the LLC. ORS 63.130 provides in part:
ORS 63.130(2)(b).
The same statutes, by contrast, make the members of a manager-managed LLC (with few exceptions) little more than passive investors in the LLC. Ordinary members have essentially no control over the business. See ORS 63.130(2)(b) (generally, "any matter relating to the business of the limited liability company may be exclusively decided by the manager"); ORS 63.140(2)(a) (in manager-managed LLCs, "[a] member is not an agent of the limited liability company for the purpose of its business solely by reason of being a member"). In this case, plaintiffs' operating agreements track the general statutory principles that grant the manager authority to run the business, while withholding that authority from ordinary members.
By statute, the heightened powers of the manager also carry with them specific duties toward the LLC. See ORS 63.155(9)(b) (making duties of ORS 63.155(2)-(8) applicable to manager); ORS 63.155(2)-ORS 63.155(8) (listing duties). In particular, those duties include the obligation generally "to refrain from dealing with the limited liability company in a manner adverse to the limited liability company and to refrain from representing a person with an interest adverse to the limited liability company, in the conduct * * * of the limited liability company's business." ORS 63.155(2)(b) (subject to certain exceptions).
In contrast, the members of a manager-managed LLC owe no duty to the LLC or the other members. ORS 63.155(9)(a) provides:
With that background, we return to the question whether section 3.2 complies with ORS 63.155(10)(a)(A) by specifically identifying types or categories of activities that do not violate the duty of loyalty. We first observe that section 3.2 speaks only generically of "members," and it relieves members of any obligation either to "account to [plaintiffs]," or to be liable to plaintiffs or the other members, for investing in or managing other businesses. Section 3.2 permits ordinary members to invest their own money in other businesses and/or to manage other businesses that are doing business with plaintiffs. But investment or management by an ordinary member does not involve any conflict of interest between agent and principal, because ordinary members of a manager-managed LLC are not agents of the LLC, ORS 63.140(2)(a), and so they have no duty of loyalty to put the LLC's interest first. An ordinary member of plaintiffs does not have the authority to cause plaintiffs to take detrimental actions that might benefit that member's
What is not in section 3.2, however, is any suggestion — much less a specific statement as required by ORS 63.155(10)(a)(A) — that the managing member may bind the plaintiffs to transactions when the managing member has a conflict of interest. Unlike ordinary members, the managing member does control LLC operations. Unless checked, that authority would give the managing member vast opportunities to personally benefit at the LLC's expense. For that reason, the manager of an LLC is subject to a statutory duty to refrain from dealing with the limited liability company in a manner adverse to the limited liability company and to refrain from representing a person with an interest adverse to the limited liability company." ORS 63.155(2)(b). Nothing in section 3.2 suggests any intent to permit the managing member to act against plaintiffs' interests or to act in the interest of a party adverse to plaintiffs, such as defendant. Section 3.2 does not purport to waive the duty of loyalty or to permit conflicts of interest — duties that do not apply to ordinary members, but which were imposed by statute on Berkman as managing member. Section 3.2 also does not purport to change the default rule that transactions involving a conflict of interest by the manager must be approved by a majority of members. See ORS 63.130(4)(h). Even considered as a question of contractual interpretation, we are not persuaded that section 3.2's generic release of any obligation by "[m]embers" to "account" for other investments was intended to waive the managing member's duty to avoid conflicts of interest. We do not agree that section 3.2 qualifies as the sort of specific approval of a managing member's duty to avoid conflicts of interest as required by ORS 63.155(10)(a)(A).
Because section 3.2 does not specifically identify or authorize the managing member to engage in transactions in which the managing member has a conflict of interest, ORS 63.155(10)(a)(A), we conclude that the operating agreements did not specifically permit Berkman to approve the amendment if he had a conflict of interest.
Even if Berkman lacked authority to amend the loan agreement, however, plaintiffs would still be bound by the amendment unless defendant knew or should have known that Berkman lacked authority. See ORS 63.140(2)(a) (so stating). We turn to that question.
As noted, each operating agreement contained the following provision:
Defendant asserts that, under the operating agreements, it was entitled to rely on Berkman's authority to approve the amendment on behalf of plaintiffs without making any further inquiry. Defendant's argument misses the point. As chairman of the board and treasurer for defendant, Berkman was an agent for defendant. Essentially everything
Moreover, defendant would have actually known the facts that would show that Berkman's conflict of interest deprived him of authority. Defendant does not and cannot dispute that it knew that Berkman was managing member for plaintiffs or that he executed the amendment to the loan agreement on behalf of plaintiffs. Defendant also cannot deny having known that Berkman was its own chairman of the board and treasurer, that Berkman had a significant financial stake in it through his stock ownership, or that defendant periodically was giving Berkman interest-free loans. And of course defendant knew all the details of the allegedly unfair amendment to the loan agreement itself. In short, defendant already knew essentially everything about Berkman's conflict of interest.
If the factfinder concludes that Berkman's conflict of interest with plaintiffs deprived him of authority to approve the amendment to the loan agreement, then defendant knew about that conflict of interest, both in fact and as imputed by the knowledge of its agent. Because defendant would have known that Berkman had a conflict, defendant would have known that Berkman lacked authority to enter into the amendment on behalf of plaintiffs. The provision of the operating agreements suggesting that third parties need make no further inquiry into Berkman's authority would be irrelevant under those circumstances. Unlike third parties dealing with plaintiffs at arm's length, defendant would not have needed to make any further inquiry; defendant already would have known the answer. See Portland v. American Surety Co., 79 Or. 38, 43, 153 P. 786 (1915), on motion to further modify decree, 79 Or. 38, 154 P. 121 (1916) (principal will not be bound by acts of agent, even though acts were within agent's apparent authority, "in the presence of the actual knowledge of the third party as to the real scope of the agent's authority").
To summarize: Under ORS 63.140(2)(a), an LLC is not bound by a transaction if the manager lacked authority to enter into the transaction and the other party knew or should have known of that lack of authority. We conclude that there was a genuine issue of material fact whether Berkman's conflict of interest in agreeing to the amendment on behalf of plaintiffs deprived him of authority to act on behalf of plaintiffs in that transaction. Defendant would have had both actual and imputed knowledge of the conflict of interest and the lack of authority. Accordingly, unless plaintiffs later ratified the amendment (an issue that we will consider next), plaintiffs would not be bound by the amendment to the loan agreement.
Finally, defendant argues that there is an alternative ground that supports the trial court's summary judgment ruling. According to defendant, even if Berkman lacked authority to enter into the amendment, plaintiffs' seven-month delay in making any objection amounted to ratification by silence of the unauthorized act. See Michel v. ICN Pharmaceuticals, 274 Or. 795, 805, 549 P.2d 519 (1976) (if purported principal is told of actions of purported agent "under circumstances which reasonably justify an inference of consent unless the principal discloses his dissent, the failure of the principal to dissent
Neither the trial court nor the Court of Appeals reached defendant's ratification argument. Nevertheless, we have considered that argument and, at this stage of the proceedings, reject it. Although a principal may ratify the unauthorized acts of an agent by silence, we do not agree that the facts of this case justify summary judgment in defendant's favor. "It is a question of fact in the particular circumstances whether the lapse in time [in objecting] is sufficient to constitute ratification." Restatement (Third) of Agency § 4.01 comment f; see Michel, 274 Or. at 804-05, 549 P.2d 519 (noting that "the question of ratification is ordinarily a question of fact"); Phillips, 195 Or. at 296, 243 P.2d 276 ("[r]atification is a question of fact" (internal quotation marks and citation omitted)). Specifically, ratification by silence requires the factfinder to draw an inference about the principal's state of mind. See Michel, 274 Or. at 805 n. 2, 549 P.2d 519 ("Ratification is based upon waiver — the intentional relinquishment of a known right — rather than upon estoppel."). On this record we cannot conclude that there is no issue of fact as to whether the length of time that plaintiffs delayed in making their objection served to ratify the amendment.
Plaintiffs have also asserted on review that the trial court should have granted summary judgment in their favor. We disagree. For the reasons we have already noted, there are triable questions of fact in this case: whether the transaction was fair to plaintiffs, and whether plaintiffs ratified the amendment by inaction. Accordingly, we affirm the trial court insofar as it denied plaintiffs' motion for summary judgment.
After entry of the general judgment, the trial court entered a supplemental money judgment for attorney fees and costs against plaintiffs, and plaintiffs separately appealed that supplemental judgment. Our conclusion that the trial court erred in granting summary judgment necessarily reverses that attorney fee award. See ORS 20.220(3)(a) ("If the appellate court reverses the judgment [as to which an award of attorney fees or costs relates], the award of attorney fees or costs and disbursements shall be deemed reversed[.]"). Without deciding whether a separate notice of appeal was necessary in light of the statutory text, we also reverse the trial court's supplemental judgment.
Under ORS 63.140(2)(a), an LLC is not bound by the act of its manager if the manager
The decision of the Court of Appeals is reversed. The judgments of the circuit court are reversed, and the case is remanded to the circuit court for further proceedings.
We agree with defendant that plaintiffs are manager-managed LLCs because all their operating agreements specifically designate a manager. See ORS 63.001(20) (defining "manager-managed limited liability company" to include an LLC "whose articles of organization otherwise expressly provide that the limited liability company will be managed by a manager or managers"); compare ORS 63.001(22) (defining "member-managed limited liability company" as all other types of LLCs). Although each operating agreement designated the manager as the "Managing Member," that would not transform plaintiffs into member-managed LLCs. See ORS 63.001(19) (by implication: "`Manager' or `managers' means a person or persons, who need not be members, designated by the members of a manager-managed limited liability company to manage the limited liability company's business and affairs." (Emphasis added.)).