The most common mistake in a first Bitcoin allocation is not the price paid. It is assuming the execution will take care of itself.

Teams make the buy decision, line up the approval, and then route a seven-figure order through the same retail venue they would use to buy a few hundred dollars of Bitcoin. The order fills, but not at the price they saw. The gap between the quoted price and what they actually paid can be significant, and on a large order it is real money.

Buying Bitcoin is operationally straightforward. Buying it well, at size, is not.

Michael Geraci, derivatives trader at Secure Digital Markets, covers the exchange, execution, and OTC relationships institutional Bitcoin holders need to understand before the first dollar moves. Will Reeves, CEO of Fold, joins with the operator’s view from running a public company that holds Bitcoin on its own balance sheet.

“At a million dollars and up is really where the OTC markets offer depth and liquidity.” — Michael Geraci, Secure Digital Markets

What this session covers

When a retail exchange stops being enough

Past a certain size, execution cost becomes real. Slippage becomes material around $250K in notional and is unambiguous past $1M, where retail order books cannot absorb the trade cleanly.
A $1M Bitcoin buy typically runs 5 to 60 bps in execution cost. On a single trade that looks small; across a recurring accumulation program it is the difference that decides your cost basis.
OTC desks exist to solve this, offering real depth, bilateral pricing, and a counterparty accountable on the other end of the phone.

How a large order actually gets worked

Size is worked, not clicked. A meaningful order is sliced across venues and over time rather than dropped into a single book that it would move against itself.
Execution is benchmarked. Working an order against TWAP or VWAP lets it track the market instead of running ahead of it, which is the difference between a fill a treasurer can defend to a board and one they cannot.
Discretion matters. Bilateral pricing keeps a large order off the public tape, so the trade does not signal its own size to the rest of the market.

The operational groundwork that makes execution clean

Tier-1 banking relationships matter. Fiat needs to move cleanly, and wires to crypto venues are routinely flagged or blocked at banks that are not set up for them. Established banking rails remove that friction.
Work with a firm that picks up the phone. Setting up to trade at size involves real onboarding, banking, and compliance questions, and the answers are specific to each entity. A client-centric desk walks you through them with a named person on the other end of the line, rather than leaving you to a support inbox or a contact form.
Settlement speed is an edge. Pre-funded trades that settle T+0 to T+1 reduce the window in which anything can go wrong, rather than leaving funds in transit for days.
Flexibility is the point of a desk. Bespoke, bilateral structuring gives a treasury options a public order book cannot, from how an order is filled to how a position is later hedged or financed.

Get these pieces right and the first allocation stops being a leap of faith. The price you pay is defensible, the execution is clean, and you have a counterparty who answers when you call. From there, the same desk can help the position do more than sit, structuring yield, downside protection, and financing against Bitcoin you already hold, which is exactly the role a desk like SDM is built to play.

About Secure Digital Markets

SDM is a crypto-native institutional brokerage offering spot execution, derivatives, and structured lending. It specializes in bilateral transactions that give treasuries the depth, flexibility, and privacy a retail exchange cannot match, while clients retain custody of their own assets. You can learn more at SDM.co.