Interview Questions156

    Overnight Bought Deals: Risk Capital and Speed

    In a bought deal, the bank takes firm commitment on the full offering at 4-8% discount, redistributing overnight before the next morning's open.

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    10 min read
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    3 interview questions
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    Introduction

    An overnight bought deal is the most aggressive of the standard follow-on products: the underwriting bank purchases the entire offering at a fixed price after market close, then has overnight to redistribute the shares to institutional investors through an accelerated bookbuild before the next morning's open. The structure transfers all execution risk from the issuer to the bank in exchange for a wider discount, which is why it is the preferred product when speed and price certainty matter more than minimizing dilution. The format is dominant in Canada (where bought deals account for the bulk of follow-on volume) and is widely used in the US and Europe for time-sensitive primary issuance. Understanding the mechanics, the bank's risk-pricing process, the bake-off dynamics, and when the structure beats a marketed follow-on is core ECM knowledge.

    The Bought-Deal Sequence

    The overnight bought deal compresses the entire follow-on workflow into roughly fifteen hours.

    1

    Pre-Launch Bank Pitch

    The bank approaches the issuer (or vice versa) with a bought-deal proposal: size, indicated price, and underwriting terms. Discussion can run hours to days before commitment.

    2

    Issuer Commitment (4:00pm)

    Issuer accepts the bought-deal price and signs the underwriting agreement after market close. Bank now owns the offering at the agreed price.

    3

    Accelerated Bookbuild Launch (4:00-5:00pm)

    Bank's syndicate desk announces the deal and begins calling institutional accounts on a wall-crossed basis to gather firm orders.

    4

    Order Book Builds (5:00pm-Midnight)

    Sales coverage at the bank works through the institutional account list rapidly, taking firm commitments at the offering price. Book building is materially faster than a marketed follow-on.

    5

    Final Demand Confirmation (Midnight-1:00am)

    Syndicate desk confirms the book is covered. If oversubscribed, the bank may upsize the deal. If undersubscribed at the agreed price, the bank holds the gap on its balance sheet.

    6

    Allocations Notified (Pre-Open)

    Investors receive allocation confirmations before the next morning's market open.

    7

    New Shares Trade (Next Morning)

    New shares trade alongside existing common stock when the market opens. Bank monitors trading and unwinds any residual position.

    Accelerated Bookbuild (ABB)

    A method of placing equity in which the bookbuilding process is compressed into 1 to 2 days (sometimes a single overnight session) with minimal marketing. Investors are approached by the syndicate desk on a wall-crossed basis and legally binding commitments are received over the phone or chat. ABBs are the marketing mechanism inside an overnight bought deal: the bank uses the ABB to redistribute shares it has purchased from the issuer at the bought-deal price.

    The Bank's Capital Commitment

    The principal feature distinguishing a bought deal from a marketed follow-on is the bank's capital commitment.

    The Firm Commitment

    In a firm commitment, the bank purchases the entire offering from the issuer at the agreed price regardless of subsequent demand. If the bank cannot place the shares to investors at the offering price overnight, it holds the residual position on its balance sheet at the bank's expense. The structure transfers all execution risk from the issuer to the bank, which is why bought deals price at wider discounts than marketed follow-ons: the wider discount compensates the bank for the principal risk it is accepting.

    Firm Commitment Underwriting

    A securities-offering structure where the underwriting bank purchases the entire offering from the issuer at a negotiated fixed price and assumes all distribution risk. If the bank cannot place all the shares at the offering price, it holds the residual on its balance sheet. Firm commitment is the default structure for bought deals and the principal differentiator from "best efforts" structures where the bank simply markets without committing capital.

    The Internal Committee Approval Process

    Before committing capital, the senior banker on the bought-deal team must obtain approval from the bank's commitment committee, which typically includes the global head of ECM, the head of equity trading, the bank's risk officer, and (for larger commitments) the firm's chief risk officer. The committee evaluates the issuer's stock-price stability, the institutional investor base's depth, the prevailing market environment, the offering size relative to typical daily trading volume, and any specific catalysts (pending earnings, regulatory events) that could disrupt overnight execution. Approval frequently requires the desk to articulate a specific hedging plan and a residual-position cap (the maximum size the bank will hold on the balance sheet if the book does not clear).

    Hedging and When the Bank Loses

    Banks executing bought deals typically hedge the principal risk through their own trading book, pre-positioning hedges in correlated names or structuring offsetting trades to manage the overnight exposure. The bank's overnight P&L on the principal position can be summarized as:

    Bank P&L=(PreofferPbought)×SharesHedging Cost\text{Bank P\&L} = (P_{\text{reoffer}} - P_{\text{bought}}) \times \text{Shares} - \text{Hedging Cost}

    The hedging capability is one reason bulge brackets dominate the bought-deal market: smaller banks lack the trading infrastructure to manage the risk efficiently. When a bought deal fails to clear, the bank holds the residual position, sells into the open market at a lower price, or accepts the loss against the bought price. Risk officers track win-loss ratios, average residual sizes, and time-to-clear statistics; desks that consistently miss see capital allocation tightened until pricing discipline improves.

    The Bake-Off Versus Sole-Source Decision

    Issuers approach the bought-deal market in one of two ways, and the choice meaningfully affects pricing.

    The Confidential Bake-Off

    Most large bought deals are run as confidential bake-offs among two or three bulge brackets. The issuer (or the issuer's financial advisor) sends a confidential request-for-proposal to the selected banks specifying size, indicated discount range, and bid deadline. Banks return their best price within a tight window (typically 1 to 3 hours) and the issuer selects the winner. The bake-off extracts the tightest pricing the market will support but creates execution risk because the losing banks know the deal is happening and could leak information.

    The Sole-Source Mandate

    In a sole-source mandate, the issuer awards the bought deal to a specific bank (typically the IPO lead-left or the bank with the strongest current relationship) without competitive bidding. Sole-source deals price at modestly wider discounts than competitive bake-offs because the bank does not have the pricing pressure of competition, but the format reduces leak risk and rewards relationship investment. Sole-source mandates are common for sponsor-backed issuers where the IPO lead has built the institutional base and is the natural execution partner.

    When Issuers Pick Each Approach

    Bake-offs are common when the issuer wants to test pricing tightness with multiple competing banks. Sole-source mandates are common when the issuer values relationship continuity and wants to avoid leak risk. Sophisticated CFOs alternate between the two approaches across successive transactions to maintain competitive tension across the bank panel.

    Variable Price Reoffer Structures

    Some bought deals use a variable price reoffer (VPR) format rather than a flat firm bid.

    A flat firm bid is a single price at which the bank commits to purchase the offering. A VPR sets a floor (the bank's worst-case purchase price) and a reoffer mechanism whereby the final price is set after the overnight bookbuild based on actual demand. If demand exceeds expectations, the issuer captures some upside through a higher transfer price; if demand falls short, the bank takes the offering at the floor. VPR shares upside between issuer and bank and produces tighter floor pricing than a flat firm bid, with the trade-off that the issuer accepts variable proceeds. VPR structures are increasingly common on larger or more volatile bought deals where banks are unwilling to commit to a flat firm bid but issuers still want some price-certainty protection.

    When the Bought Deal Wins Versus the Marketed Follow-On

    The choice between bought deal and marketed follow-on turns on several specific issuer-side trade-offs.

    Speed and Certainty

    Bought deals execute in 15-18 hours; marketed follow-ons execute in 2-4 days. Issuers facing time-sensitive situations (binary catalyst, competitive M&A bid, regulatory deadline) almost always favor bought deals despite the wider discount because the alternative is uncertainty about whether the marketed deal will clear in time.

    Discount Differential

    Bought deals typically price 1 to 3 percent wider than an equivalent marketed follow-on. The wider spread compensates the bank for principal risk and the compressed window. Issuers comfortable with marketing-window execution risk usually prefer the marketed format to capture the tighter pricing.

    Issuer Profile

    Bought deals work best for issuers with stable trading patterns, strong existing institutional bases, and offering sizes within 5 to 10 percent of trailing 30-day ADV. Issuers with stressed multiples, recent volatility, or larger sizes typically push the bank toward wider discounts that may make the marketed format more attractive despite the longer timeline.

    DimensionBought DealMarketed Follow-On
    Execution time15-18 hours2-4 days
    Bank capital commitmentFull (principal risk)None (best efforts)
    Typical discount to last sale4-8%2-7%
    Issuer execution riskZero (bank takes the risk)Real (deal could revise or pull)
    Marketing intensitySingle-night accelerated bookbuildCompressed roadshow with management
    Best fitTime-sensitive, smaller relative to ADVLarger, stable issuer, broader marketing

    A bought-deal book that clears at the offering price closes the loop on the bank's overnight risk; the issuer captures speed and certainty in exchange for the wider discount the bank charged for taking on the principal exposure. The same firm-commitment muscle that powers a bought deal also serves a different purpose entirely on the secondary side, where the supply originates from a sponsor or insider rather than from the issuer. Block trades are next.

    Interview Questions

    3
    Interview Question #1Medium

    What is an overnight bought deal?

    A bought deal is a follow-on where the underwriter purchases the entire offering from the issuer at a fixed price after market close, then sells the shares overnight to institutional investors before market open the next day.

    Mechanics: typically initiated as a competitive process where the issuer (or its lead bank) approaches multiple banks for bids on a wall-crossed basis. The winning bidder commits principal capital to buy all shares at a fixed price (typically a 3 to 7% discount to last trade). The underwriter then has the overnight window to "sell down" to institutional buyers and reduce its position before markets open.

    Used for fast execution, small-to-mid size deals (typically under $1B, sometimes larger), and when the issuer wants pricing certainty without market-timing risk. Common for sponsor sell-downs and quick capital raises.

    Interview Question #2Medium

    What risk does the underwriter take in a bought deal that it doesn't take in a marketed follow-on?

    Principal price risk. In a bought deal, the underwriter buys the shares at a fixed price and then has to resell. If overnight demand comes in below the bought price, the underwriter eats the difference. If markets gap down before the resale completes, the loss compounds.

    In a marketed follow-on, the underwriter is on a "best efforts" or agency basis: the bank takes orders, books demand, and prices at the level the book clears. If demand is weak, the deal prices lower or gets pulled, but the underwriter doesn't carry shares on its balance sheet at risk.

    This is why bought deals trade at wider discounts than marketed follow-ons: the underwriter prices in compensation for principal risk.

    Interview Question #3Hard

    A sponsor sells 20M shares in a bought deal at a 5% discount to the $50 closing price. The bank commits the principal and resells overnight. By morning, the bank has placed 90% of the shares with institutions at the bought price, and 10% remains in inventory. The stock opens at $46.50. What is the bank's P&L?

    Bought price: $50 × (1 − 0.05) = $47.50 per share.

    Total bought: 20M × $47.50 = $950M committed principal.

    Resold overnight: 90% × 20M = 18M shares at $47.50 = $855M proceeds.

    Inventory remaining: 2M shares carried into market open at $46.50 market price.

    Mark on inventory: 2M × ($46.50 − $47.50) = −$2M unrealized loss before realization.

    Plus underwriting fee (typically 1 to 2% of deal size on a bought deal; assume 1.5%): 20M × $47.50 × 1.5% = $14.25M fee revenue.

    Net P&L if inventory is sold at $46.50: $14.25M fee − $2M inventory loss = +$12.25M net.

    If the stock keeps falling and the inventory is closed at $44, the inventory loss grows to $7M and net P&L drops to $7.25M. Real bought deals can produce both windfall gains (stock rallies, inventory closes at a profit) and losses (stock drops, inventory loss exceeds fees). Banks size principal commitments based on risk-budget capacity.

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