We measure certain financial assets and liabilities at fair value on a recurring basis, including financial instruments owned, available-for-sale securities, investments, financial instruments sold, but not yet purchased, and derivatives.

We generally utilize third-party pricing services to value Level 1 and Level 2 available-for-sale investment securities, as well as certain derivatives designated as cash flow hedges. We review the methodologies and assumptions used by the third-party pricing services and evaluate the values provided, principally by comparison with other available market quotes for similar instruments and/or analysis based on internal models using available third-party market data. We may occasionally adjust certain values provided by the third-party pricing service when we believe, as the result of our review, that the adjusted price most appropriately reflects the fair value of the particular security.

Following are descriptions of the valuation methodologies and key inputs used to measure financial assets and liabilities recorded at fair value. The descriptions include an indication of the level of the fair value hierarchy in which the assets or liabilities are classified.

When available, the fair value of financial instruments is based on quoted prices in active markets and reported in Level 1. Level 1 financial instruments include highly liquid instruments with quoted prices, such as equity securities listed in active markets, corporate fixed income securities, and U.S. government securities.

If quoted prices are not available for identical instruments, fair values are obtained from pricing services, broker quotes, or other model-based valuation techniques with observable inputs, such as the present value of estimated cash flows, and reported as Level 2.

The nature of these financial instruments include instruments for which quoted prices are available but traded less frequently, instruments whose fair value has been derived using a model where inputs to the model are directly observable in the market, or can be derived principally from or corroborated by observable market data, and instruments that are fair valued using other financial instruments, the parameters of which can be directly observed. Level 2 financial instruments include U.S. government agency securities, mortgage-backed securities, fixed income and equity securities infrequently traded, state and municipal securities, sovereign debt, and asset-backed securities, which primarily include collateralized loan obligations.

We have identified Level 3 financial instruments to include loans and certain asset-backed securities with unobservable pricing inputs. Level 3 financial instruments have little to no pricing observability as of the report date. These financial instruments do not have active two-way markets and are measured using management’s best estimate of fair value, where the inputs into the determination of fair value require significant management judgment or estimation.

Investments carried at fair value primarily include corporate equity securities, auction-rate securities (“ARS”), and private company investments.

Corporate equity securities are primarily valued based on quoted prices in active markets and reported in Level 1.

ARS are primarily valued based upon our expectations of issuer redemptions and using internal discounted cash flow models that utilize unobservable inputs. ARS are primarily reported as Level 3 assets. Private company investments are primarily valued based upon internally developed models. These valuations require significant management judgment due to the absence of quoted market prices, the inherent lack of liquidity, and their long-term nature. Typically, the initial costs of these investments are considered to represent fair market value, as such amounts are negotiated between willing market participants. Private company investments are primarily reported as Level 3 assets.

Investments at fair value include investments in funds, including certain money market funds that are measured at net asset value (“NAV”). The Company uses NAV to measure the fair value of its fund investments when (i) the fund investment does not have a readily determinable fair value and (ii) the NAV of the investment fund is calculated in a manner consistent with the measurement principles of investment company accounting, including measurement of the underlying investments at fair value.

The Company’s investments in funds measured at NAV include partnership interests, mutual funds, private equity funds, and money market funds. Private equity funds primarily invest in a broad range of industries worldwide in a variety of situations, including leveraged buyouts, recapitalizations, growth investments and distressed investments. The private equity funds are primarily closed-end funds in which the Company’s investments are generally not eligible for redemption. Distributions will be received from these funds as the underlying assets are liquidated or distributed.

The general and limited partnership interests in investment partnerships were primarily valued based upon NAVs received from third-party fund managers. The various partnerships are investment companies, which record their underlying investments at fair value based on fair value policies established by management of the underlying fund. Fair value policies at the underlying fund generally require the funds to utilize pricing/valuation information, including independent appraisals, from third-party sources. However, in some instances, current valuation information for illiquid securities or securities in markets that are not active may not be available from any third-party source or fund management may conclude that the valuations that are available from third-party sources are not reliable. In these instances, fund management may perform model-based analytical valuations that may be used as an input to value these investments.

The table below presents the fair value of our investments in, and unfunded commitments to, funds that are measured at NAV as of June 30, 2021 and December 31, 2020 (in thousands):

Financial instruments sold, but not purchased, recorded at fair value based on quoted prices in active markets and other observable market data include highly liquid instruments with quoted prices, such as U.S. government securities, equity and fixed income securities listed in active markets, which are reported as Level 1.

If quoted prices are not available, fair values are obtained from pricing services, broker quotes, or other model-based valuation techniques with observable inputs, such as the present value of estimated cash flows, and reported as Level 2. The nature of these financial instruments include instruments for which quoted prices are available but traded less frequently, instruments whose fair value has been derived using a model where inputs to the model are directly observable in the market, or can be derived principally from or corroborated by observable market data, and instruments that are fair valued using other financial instruments, the parameters of which can be directly observed. Level 2 financial instruments include agency mortgage-backed securities not actively traded, fixed income and equity securities, sovereign debt securities, and state and municipal securities.

Assets and liabilities measured at fair value on a recurring basis as of June 30, 2021, are presented below (in thousands):

	June 30, 2021
	Total		Level 1		Level 2		Level 3
Financial instruments owned:
U.S. government securities	$	19,998	$	19,998	$	—	$	—
U.S. government agency securities		171,470		—		171,470		—
Agency mortgage-backed securities		389,828		—		389,828		—
Asset-backed securities		25,780		—		23,965		1,815
Corporate securities:
Fixed income securities		377,349		700		376,649		—
Equity securities		102,567		100,865		1,702		—
Sovereign debt		26,375		—		26,375		—
State and municipal securities		106,967		—		106,967		—
Loans		22,839		—		—		22,839
Other		1,840		—		1,840		—
Total financial instruments owned		1,245,013		121,563		1,098,796		24,654
Available-for-sale securities:
U.S. government agency securities		3,180		—		3,180		—
State and municipal securities		2,430		—		2,430		—
Mortgage-backed securities:
Agency		1,011,876		—		1,011,876		—
Commercial		80,561		—		80,561		—
Non-agency		1,752		—		1,752		—
Corporate fixed income securities		809,569		—		809,569		—
Asset-backed securities		370,789		—		370,789		—
Total available-for-sale securities		2,280,157		—		2,280,157		—
Investments:
Corporate equity securities		26,137		17,382		1		8,754
Auction rate securities		12,959		—		—		12,959
Other		51,340		10,568		6,106		34,666
Investments in funds and partnerships measured at NAV		19,729
Total investments		110,165		27,950		6,107		56,379
Cash equivalents measured at NAV		8,493
	$	3,643,828	$	149,513	$	3,385,060	$	81,033

	June 30, 2021
	Total		Level 1		Level 2		Level 3
Liabilities:
Financial instruments sold, but not yet purchased:
U.S. government securities	$	370,149	$	370,149	$	—	$	—
U.S. government agency securities		60,502		—		60,502		—
Agency mortgage-backed securities		188,946		—		188,946		—
Corporate securities:
Fixed income securities		175,477		137		175,340		—
Equity securities		40,931		39,972		959		—
Other ⁽¹⁾		12,905		—		12,905		—
Total financial instruments sold, but not yet purchased	$	848,910	$	410,258	$	438,652	$	—

Assets and liabilities measured at fair value on a recurring basis as of December 31, 2020, are presented below (in thousands):

	December 31, 2020
	Total		Level 1		Level 2		Level 3
Financial instruments owned:
U.S. government securities	$	46,900	$	46,900	$	—	$	—
U.S. government agency securities		56,450		—		56,450		—
Agency mortgage-backed securities		216,434		—		216,434		—
Corporate securities:
Fixed income securities		194,575		4,474		190,101		—
Equity securities		67,593		62,979		4,614		—
State and municipal securities		96,150		—		96,150		—
Other ⁽¹⁾		15,926		—		4,642		11,284
Total financial instruments owned		694,028		114,353		568,391		11,284
Available-for-sale securities:
U.S. government agency securities		4,361		—		4,361		—
State and municipal securities		2,453		—		2,453		—
Mortgage-backed securities:
Agency		793,410		—		793,410		—
Commercial		95,613		—		95,613		—
Non-agency		4,569		—		4,569		—
Corporate fixed income securities		631,758		—		631,758		—
Asset-backed securities		698,133		—		698,133		—
Total available-for-sale securities		2,230,297		—		2,230,297		—
Investments:
Corporate equity securities		29,496		29,496		—		—
Auction rate securities		12,933		—		—		12,933
Other		59,048		10,342		6,593		42,113
Investments in funds and partnerships measured at NAV		12,385
Total investments		113,862		39,838		6,593		55,046
Cash equivalents measured at NAV		34,192
	$	3,072,379	$	154,191	$	2,805,281	$	66,330

	December 31, 2020
	Total		Level 1		Level 2		Level 3
Liabilities:
Financial instruments sold, but not yet purchased:
U.S. government securities	$	91,974	$	91,974	$	—	$	—
Agency mortgage-backed securities		141,227		—		141,227		—
Corporate securities:
Fixed income securities		162,626		4,094		158,532		—
Equity securities		30,848		30,848		—		—
Other ⁽²⁾		11,303		—		11,303		—
Total financial instruments sold, but not yet purchased	$	437,978	$	126,916	$	311,062	$	—

The following table summarizes the changes in fair value associated with Level 3 financial instruments during the three months ended June 30, 2021 (in thousands):

				Three Months Ended June 30, 2021
	Financial instruments owned						Investments
	Asset-backed Securities			Loans			Corporate Equity Securities		Auction Rate Securities		Other
Balance at March 31, 2021	$	9		$	14,268		$	2,000	$	12,959	$	41,828
Unrealized losses		(3,000	)		(27	)		—		—		(232	)
Realized gains		7,361			—			—		—		—
Purchases		76			8,598			1,000		—		—
Redemptions		(9,561	)		—			—		—		—
Transfers into Level 3		—			—			5,754		—		—
Category transfers		6,930			—			—		—		(6,930	)
Net change		1,806			8,571			6,754		—		(7,162	)
Balance at June 30, 2021	$	1,815		$	22,839		$	8,754	$	12,959	$	34,666

The following table summarizes the change in fair value associated with Level 3 financial instruments during the six months ended June 30, 2021 (in thousands):

	Six Months Ended June 30, 2021
	Financial instruments owned						Investments
	Asset-backed Securities			Loans			Corporate Equity Securities		Auction Rate Securities		Other
Balance at December 31, 2020	$	9		$	11,275		$	—	$	12,933	$	42,113
Unrealized gains/(losses)		(3,000	)		(48	)		—		26		(517	)
Realized gains		7,361			—			—		—		—
Purchases		76			11,612			3,000		—		—
Redemptions		(9,561	)		—			—		—		—
Transfers into Level 3		—			—			5,754		—		—
Category transfers		6,930			—			—		—		(6,930	)
Net change		1,806			11,564			8,754		26		(7,447	)
Balance at June 30, 2021	$	1,815		$	22,839		$	8,754	$	12,959	$	34,666

The results included in the tables above are only a component of the overall investment strategies of our company. The tables above do not present Level 1 or Level 2 valued assets or liabilities. The changes in unrealized gains/(losses) recorded in earnings for the three and six months ended June 30, 2021, relating to Level 3 assets still held at June 30, 2021, were immaterial.

The fair value of certain Level 3 assets was determined using various methodologies, as appropriate, including third-party pricing vendors and broker quotes. These inputs are evaluated for reasonableness through various procedures, including due diligence reviews of third-party pricing vendors, variance analyses, consideration of current market environment, and other analytical procedures.

The fair value for our auction rate securities was determined using an income approach based on an internally developed discounted cash flow model. The discounted cash flow model utilizes two significant unobservable inputs: discount rate and workout period. Significant increases in any of these inputs in isolation would result in a significantly lower fair value. On an ongoing basis, management verifies the fair value by reviewing the appropriateness of the discounted cash flow model and its significant inputs.

The following reflects the fair value of financial instruments as of June 30, 2021 and December 31, 2020, whether or not recognized in the consolidated statements of financial condition at fair value (in thousands).

	June 30, 2021				December 31, 2020
	Carrying Value		Estimated Fair Value		Carrying Value		Estimated Fair Value
Financial assets:
Cash and cash equivalents	$	1,361,521	$	1,361,521	$	2,279,274	$	2,279,274
Cash segregated for regulatory purposes		144,587		144,587		172,932		172,932
Securities purchased under agreements to resell		622,930		622,930		217,930		217,930
Financial instruments owned		1,245,013		1,245,013		694,028		694,028
Available-for-sale securities		2,280,157		2,280,157		2,230,297		2,230,297
Held-to-maturity securities		4,987,612		4,992,139		4,117,384		4,107,960
Bank loans		12,770,941		12,808,962		11,006,760		11,088,058
Loans held for sale		394,017		394,017		551,248		551,248
Investments		110,165		110,165		113,862		113,862
Financial liabilities:
Securities sold under agreements to repurchase	$	407,246	$	407,246	$	190,955	$	190,955
Bank deposits		19,608,800		19,420,005		17,396,497		17,192,722
Financial instruments sold, but not yet purchased		848,910		848,910		437,978		437,978
Senior notes		1,112,941		1,243,851		1,112,409		1,265,669
Debentures to Stifel Financial Capital Trusts		60,000		45,174		60,000		41,071

The following tables present the estimated fair values of financial instruments not measured at fair value on a recurring basis as of June 30, 2021 and December 31, 2020 (in thousands):

	June 30, 2021
	Total		Level 1		Level 2		Level 3
Financial assets:
Cash	$	1,353,028	$	1,353,028	$	—	$	—
Cash segregated for regulatory purposes		144,587		144,587		—		—
Securities purchased under agreements to resell		622,930		379,935		242,995		—
Held-to-maturity securities		4,992,139		—		4,825,661		166,478
Bank loans		12,808,962		—		12,808,962		—
Loans held for sale		394,017		—		394,017		—
Financial liabilities:
Securities sold under agreements to repurchase	$	407,246	$	—	$	407,246	$	—
Bank deposits		19,420,005		—		19,420,005		—
Senior notes		1,243,851		1,243,851		—		—
Debentures to Stifel Financial Capital Trusts		45,174		—		—		45,174

	December 31, 2020
	Total		Level 1		Level 2		Level 3
Financial assets:
Cash	$	2,245,082	$	2,245,082	$	—	$	—
Cash segregated for regulatory purposes		172,932		172,932		—		—
Securities purchased under agreements to resell		217,930		164,094		53,836		—
Held-to-maturity securities		4,107,960		—		3,943,944		164,016
Bank loans		11,088,058		—		11,088,058		—
Loans held for sale		551,248		—		551,248		—
Financial liabilities:
Securities sold under agreements to repurchase	$	190,955	$	—	$	190,955	$	—
Bank deposits		17,192,722		—		17,192,722		—
Senior notes		1,265,669		1,265,669		—		—
Debentures to Stifel Financial Capital Trusts		41,071		—		—		41,071

The following, as supplemented by the discussion above, describes the valuation techniques used in estimating the fair value of our financial instruments as of June 30, 2021 and December 31, 2020.

Securities purchased under agreements to resell are collateralized financing transactions that are recorded at their contractual amounts plus accrued interest. The carrying values at June 30, 2021 and December 31, 2020 approximate fair value due to their short-term nature.

Securities held to maturity are recorded at amortized cost based on our company’s positive intent and ability to hold these securities to maturity. Securities held to maturity include agency mortgage-backed securities, asset-backed securities, consisting of collateralized loan obligation securities and corporate fixed income securities. The estimated fair value, included in the above table, is determined using several factors; however, primary weight is given to discounted cash flow modeling techniques that incorporated an estimated discount rate based upon recent observable debt security issuances with similar characteristics.

The fair values of mortgage loans and commercial loans were estimated using a discounted cash flow method, a form of the income approach. Discount rates were determined considering rates at which similar portfolios of loans, with similar remaining maturities, would be made and considering liquidity spreads applicable to each loan portfolio based on the secondary market.

Loans held for sale consist of fixed-rate and adjustable-rate residential real estate mortgage loans intended for sale. Loans held for sale are stated at lower of cost or market value. Market value is determined based on prevailing market prices for loans with similar characteristics or on sale contract prices.

Securities sold under agreements to repurchase are collateralized financing transactions that are recorded at their contractual amounts plus accrued interest. The carrying values at June 30, 2021 and December 31, 2020 approximate fair value due to the short-term nature.

The fair value of interest-bearing deposits, including certificates of deposits, demand deposits, savings, and checking accounts, was calculated by discounting the future cash flows using discount rates based on the replacement cost of funding of similar structures and terms.

The fair value of our senior notes is estimated based upon quoted market prices.

The fair value of our trust preferred securities is based on the discounted value of contractual cash flows. We have assumed a discount rate based on similar type debt instruments.

These fair value disclosures represent our best estimates based on relevant market information and information about the financial instruments. Fair value estimates are based on judgments regarding future expected losses, current economic conditions, risk characteristics of the various instruments, and other factors. These estimates are subjective in nature and involve uncertainties and matters of significant judgment and, therefore, cannot be determined with precision. Changes in the above methodologies and assumptions could significantly affect the estimates.