Acquisition

Aligning Risk

Why Deal Structure Matters

Acquisition financing typically fails on deal structure, not business fundamentals. Frequently, it’s a misalignment between pricing, structure, and risk allocation that leads to failed financing requests.

We bridge this gap for our clients. Through strategic restructuring that reopens access to banks or by navigating alternative capital markets with flexible mandates, we chart the path to secure funding at optimal terms.

Our approach begins by mapping competing interests, then engineering structures that risk align all parties. We balance buyer equity, seller participation, and debt coverage to achieve solutions that work for all parties. Seventy percent of deals declined by banks become bankable with proper structure, closing with sustainable terms, and saving significant financing costs compared to acting alone.

Results

What Diamond Willow Delivers

Bankable structure, lowest cost of capital.
We realign risks and rewards between buyers, sellers, and lenders—making 70% of previously declined deals financeable by major banks at competitive rates.

Competitive process that puts you in control.
Your deal goes to market with lender-ready materials and refined structure, creating competitive tension where capital providers come to you with their best terms.

Flexibility built into your covenants.
We negotiate realistic covenants aligned to integration timelines and business cycles, not generic templates—preserving the operational flexibility you need post-close.

Capital certainty before expensive diligence.
Early structure review and market testing means you know your financing is available before spending hundreds of thousands on accountants, quality of earnings reports, and legal fees.

A partner through close and beyond.
We stay engaged through funding, then provide ongoing board guidance and lender reporting support—protecting the relationship and terms you worked hard to secure.

Explore the acquisitions we've supported:

Case Studies

Risk Assessment

Evaluating Your Options

Acquisition financing isn’t just about finding a willing lender—it’s about understanding where risk and opportunity truly lie in your structure, terms, and timeline. Before you commit to your next step, consider these critical questions to assess whether your approach will protect your interests and support long-term success.

Did the bank decline your acquisition on business fundamentals or deal structure?

Many transactions are declined not because of weak fundamentals, but due to misaligned structure or risk allocation. Clarifying the real reason can reveal viable options, including restructuring for bank approval or targeted outreach to the right credit providers.

Are financing delays and lender rejections putting your deal at risk?

Prolonged uncertainty can erode seller confidence, invite competing offers, or lead to shifting terms. Taking a proactive approach to structure and lender alignment reduces execution risk, keeping the transaction on track.

Does your current structure distribute risk proportionately?

A structure that shares risk fairly between buyer, seller, and lender improves your negotiating position and increases the likelihood of approval. Reviewing risk allocation early helps avoid last-minute surprises and supports long-term success.

Are you putting the business at risk with this much debt?

Excess leverage or poorly structured debt can strain cash flow, restrict operations, and limit flexibility after the transaction. Modelling repayment and stress scenarios in advance protects your business and sets the stage for sustainable growth.

Do your terms fairly address liability in the event of default?

Clear, balanced terms clarify each party’s responsibilities and reduce the risk of disputes if things don’t go as planned. Addressing liability upfront is crucial to building trust and protecting your interests throughout the loan's term.

Our Approach

Supporting Your Acquisition

01.

Assessment & Strategy

Assess the Situation

Establish a clear understanding of the business, the current offer, each party's priorities, and identify where the deal does not align with lender mandates, creating a foundation to secure financing.

Build a Strategy

Define the appropriate capital approach that addresses lender concerns, whether through adjustments to risk-sharing, improved materials, or targeted outreach to mandate-aligned providers, with realistic debt service coverage and a funding timeframe that satisfies all parties.

Align Stakeholders

Coordinate communications with the buyer's management team, exiting owners, and their advisors to confirm the financing approach, manage expectations, and maintain deal momentum.

02.

Structuring & Execution

Structure

Address the specific concerns that prevented financing, whether through adjusted risk-sharing mechanisms like vendor take-back, earn-out, equity rolls , or through improved presentation of the deal fundamentals.

Package

Prepare lender-focused materials that present a coherent financing case, supported by a comprehensive data room and a clear narrative that addresses the risk tolerances of targeted lenders.

Market

Run a targeted outreach program to mandate-aligned lenders, whether major banks or alternative lenders, depending on the deal's risk profile, to secure multiple competitive offers.

03.

Diligence & Financing

Compare Offers

Analyze the offers in terms of structure, pricing, covenants, controls, fees, and future flexibility to select the option that best supports integration and operational execution.

Coordinate Diligence

Orchestrate diligence and documentation with legal counsel, accountants, target management, buyer teams, and lenders to keep timelines on track and address issues as they surface.

Secure Financing

Complete conditions precedent, execute final agreements, and oversee closing and funding to transfer ownership and establish the new capital structure.

About Us

Meet the People Behind Diamond Willow.

Our team combines institutional investment banking, Private Equity, and CFO experience with deep relationships across Canadian lending markets.

We understand how capital providers evaluate risk and structure our engagements to deliver what they need to underwrite your acquisition.

Meet The Team

Grant & Haley

Partners at Diamond Willow

Investment

Timelines & Fee Structure

Timelines

Most acquisition financing engagements are completed within 8 to 16 weeks from mandate to funding. Compressed timelines are possible when historical data is current, diligence is progressing, and leadership can commit to decision timelines and coordination requirements.

Fees

Our fees typically include a success fee of 1.5% to 2.5% of the debt raised, which is paid from the loan proceeds at closing. Engagements may involve monthly retainers during execution to coordinate the financing process and break fees if the transaction is abandoned before closing.

Relative Value

Better pricing and covenant terms typically exceed advisory fees by significant multiples. More importantly, a well-structured approach reduces costly mistakes, such as unfavorable control provisions, prevents wasted diligence spend on unfinanceable offers, and allows management to focus on integration planning rather than navigating capital markets during the most critical acquisition period.

Advisory Services

Beyond Acquisition

Pre-acquisition consulting.

Before committing to a full financing engagement, we offer consulting services on an hourly basis for capital planning and acquisition structuring. These services help you assess target businesses, understand appropriate capital structures, and determine if an offer is financeable before significant advisor spend.

Ongoing support through integration

Closing the financing is one milestone, but integration requires ongoing financial discipline. When alternative lenders finance the acquisition, most businesses need 24 to 36 months of execution before conventional banks will refinance at lower rates. We provide advisory support to guide that journey.

Learn More

Getting Back to Conventional Banking

Quarterly reporting packages that maintain lender confidence.

Strategic guidance on covenant management and performance metrics.

Financial reviews to proactively identify when banking financing is a reality.

Access To Our Network

Your acquisition may require specialized expertise beyond financing. We provide access to a vetted network of M&A advisors, legal counsel, quality of earnings specialists, and valuation professionals who can support specific aspects of your deal.

Request a Referral

Resources

Frequently Asked Questions

What factors cause banks to decline acquisition financing?

Banks typically don’t decline financing on a business's fundamentals; more frequently, it’s because of the deal structure, risk allocation, or supporting diligence not fitting their lending mandate. A structure-first approach clarifies whether approval is possible and can often reopen doors, even after an initial refusal.

If my bank won't finance my acquisition, should I approach other banks?

Other major banks typically use similar credit criteria and risk models, so outcomes are often unchanged unless the structure undergoes significant evolution. A targeted structure review is the fastest way to determine whether a revised approach can restore bankability or if alternative lenders are required.

How do I know if I need private credit or if restructuring will get the deal financed by banks?

If your deal was declined, it’s crucial to determine whether the fundamentals or structure were the barrier. In many cases, restructuring the offer around lender priorities unlocks conventional financing; when it cannot, a disciplined process with private credit providers ensures you receive competitive terms.

How do rates and terms with alternative lenders compare with banks?

Private credit usually commands higher rates but may include greater covenant flexibility. In the short term. While these lenders fill important gaps, a structure that aligns with bank mandates typically secures lower-cost capital and greater operational flexibility.

What does Diamond Willow provide that I can't already do with my existing advisors?

Your legal and accounting advisors are crucial to the process; however, structuring, packaging, and marketing acquisition debt require expertise in capital markets, access to lenders, and disciplined negotiation. We coordinate with your team but bring the specialized skillset and relationships required to secure the best terms.

What are Diamond Willow’s fees, and how are they paid?

Our fees are transparent and success-based, typically ranging from 1.5% to 2.5% of the debt raised, paid from the proceeds at funding. In some cases, a modest monthly retainer or break fee may apply. We work exclusively for you, never for lenders, aligning our interests with yours.

Acquisition Financing

When your acquisition is in sight, but financing isn’t — we help lenders see things differently.

Overview

Aligning Risk to Unlock Options