What does capital really look for when evaluating a deal?

In this episode of the M&A Source Podcast, host David Dejewski sits down with Ryan Ochs, Founder and Managing Partner of RDP Advisory, to discuss how lenders and investors evaluate middle-market transactions. Drawing on nearly two decades of experience in investment banking, private credit, underwriting, and investment committee leadership, Ryan shares practical insights into capital raising, deal preparation, and the realities of modern M&A markets.

From investment committee dynamics to family office capital, this conversation gives M&A advisors and founders a clearer understanding of what separates strong deal opportunities from those that fail to gain traction.

Ryan Ochs built his career evaluating risk and structuring capital across some of the most active credit and investment platforms in the middle market. After starting at RBC Capital Markets, he moved through roles at American Capital, Brightwood Capital, Star Mountain Advisors, and Lafayette Square, where he led underwriting and origination and served on the investment committee.

Today, through RDP Advisory, Ryan helps companies raise capital and structure transactions across the capital stack.

In this episode, Ryan explains why many businesses struggle to attract capital, how investment committees actually review opportunities, and why preparation and clarity matter more than ever in today’s disciplined market environment.

He also discusses the growing role of family offices in private markets, how advisors can better position deals for investors, and why understanding the fundamentals of how a company makes money is still the most important part of the story.

Along the way, Ryan shares real-world transaction stories—including deals that nearly collapsed at closing—and explains what strong advisors do differently to keep deals on track.

Investment committees look for clarity, not complexity

Deals must clearly explain the fundamentals: how the business makes money, what it costs to generate revenue, and how the financial story ties together.

Preparation matters before going to market

Strong transactions begin months before outreach, often with sell-side quality of earnings work, clean financial reporting, and a well-prepared narrative.

Confusion creates doubt in investors’ minds

If financials don’t reconcile or the story isn’t clear, investors begin questioning everything else in the deal.

Family offices are becoming a major capital source

Many family offices now invest directly in deals, offering flexibility and patient capital compared to traditional private equity funds.

The capital stack offers many financing options

From bank debt to private credit, mezzanine financing, structured equity, and common equity, each layer has different costs, risks, and investor expectations.

Experience still matters in dealmaking

Ryan describes M&A as an apprenticeship business where repetition, mentorship, and pattern recognition are critical to developing strong advisors.

Ryan Ochs is the Founder and Managing Partner of RDP Advisory, an independent investment and merchant bank focused on middle-market debt advisory, capital raising, and mergers and acquisitions.

Before launching RDP Advisory, Ryan served as Managing Director at Lafayette Square, where he led underwriting and origination and served on the firm’s investment committee. He previously held senior roles at Brightwood Capital, Star Mountain Advisors, American Capital, and RBC Capital Markets.

Across his career, Ryan has participated in transactions involving more than 100 companies and over $5 billion in capital raised or invested.

Website: https://rdpadvisory.com

LinkedIn: Ryan Ochs https://www.linkedin.com/in/ryancochs/

Interact with the show: https://snip.ly/mas_interact25

In this episode of the M&A Source podcast, Dave Dejewski continues a series on essential tax code provisions for mergers and acquisitions, discussing five additional provisions that can significantly impact tax outcomes for buyers, sellers, and their advisors.

The exchange is a podcast discussing 10 tax code provisions that are relevant for mergers and acquisitions (M&A) transactions. It is divided into two parts, with Part 1 covering the first 5 provisions and Part 2 covering the remaining 5 provisions.

Part 2 covers the following tax code provisions:

1. Section 368 - Tax-Free Reorganizations

This provision allows for tax-deferred treatment of certain corporate reorganizations, such as mergers and acquisitions, to encourage business continuity, growth, and realignment without triggering immediate tax liabilities. It requires continuity of interest and continuity of business enterprise.

2. Section 409A - Deferred Compensation

This provision establishes strict rules for when income can be deferred and when it must be paid, preventing abuse and ensuring fairness in the tax system. It imposes penalties for non-compliance and encourages proper planning and transparency in deferred compensation plans.

3. Section 1031 - Like-Kind Exchanges

This provision allows for the deferral of capital gains taxes when exchanging real properties for similar properties, stimulating growth in real estate-heavy businesses.

4. Section 721 - Contributions to Partnerships

This provision promotes the creation and growth of partnerships by allowing individuals or entities to contribute property to a partnership without triggering immediate tax consequences, facilitating partnership formation and encouraging joint ventures and investments.

5. Section 453 and 453A - Installment Sales

Section 453 allows sellers to report capital gains income over time through the installment sale method, aligning tax payments with the receipt of sale proceeds and providing tax deferral. Section 453A imposes an interest charge on large installment sales over $5 million to limit the tax benefits of deferring large amounts of tax.

Key Takeaways

These final five of ten tax provisions cover a wide range of areas, including tax-free reorganizations, deferred compensation, like-kind exchanges, partnership contributions, and installment sales.

The episode highlights the importance of understanding these provisions and leveraging them to minimize tax liabilities, encourage business continuity, and facilitate growth and realignment. It also emphasizes the need for proper planning, transparency, and compliance to avoid penalties and ensure that the intended tax benefits are realized.

Overall, this episode provides valuable insights into the tax considerations and strategies that should be taken into account when structuring M&A deals, making it a valuable resource for advisors, business owners, and investors involved in such transactions.

LEGAL DISCLAIMER: This resource is intended for educational purposes only and does not constitute legal, financial, or tax advice. The information provided herein should not be relied upon for any specific business or financial decision without first consulting appropriate professional counsel. Readers are encouraged to seek advice from qualified attorneys, accountants, or other professionals to address their unique circumstances. Neither the authors nor the publisher assumes any responsibility for actions taken based on the information provided in this resource.

Interact with the show: https://snip.ly/mas_interact24

The episode discusses 10 key tax code provisions relevant to mergers and acquisitions (M&A) transactions. It is divided into multiple parts, with Part 1 covering the following provisions:

1. Section 338 - Election for Treating Stock Purchases as Asset Purchases

This provision allows buyers to treat a stock purchase as if they are purchasing the underlying assets of the business, enabling them to step up the basis of the acquired assets to their fair market value for tax purposes.

2. Section 1202 - Qualified Small Business Stock Exclusions

This provision allows investors to exclude capital gains taxes on the sale of stock in qualified small businesses, subject to certain eligibility criteria.

3. Section 197 - Amortization of Goodwill and Intangibles

This provision provides uniform rules for the amortization of intangible assets, such as goodwill, franchise rights, patents, and trademarks, over a 15-year period.

4. Section 280G - Golden Parachute Payments

This provision addresses excessive compensation packages (golden parachutes) paid to executives and key employees during a change of control event, such as a merger or acquisition.

5. Section 382 - Limitation on Net Operating Losses

This provision limits the amount of net operating losses that a company can use after an ownership change to prevent companies from acquiring loss corporations solely for tax benefits.

1. "Section 338 allows buyers to treat a stock purchase as if they're purchasing the underlying assets of the business. And that means for tax purposes, the buyer can step up the basis of the acquired assets to their fair market value as opposed to the book value, which can result in greater depreciation, amortization deductions over time."

2. "Section 1202 is a powerful tool for investors and business owners who want to maximize their returns by excluding capital gains taxes on the sale of stock in small businesses."

3. "Section 197 was introduced to basically provide some uniform rules around amortization of intangible assets intangible assets, what are they it's goodwill, it's franchise rights, it's patents, it's trademarks."

4. "Section 280G of the US tax code was created to address this golden parachute concept. Golden parachute are these large compensation packages there's severance payments that are paid to executives and they're paid out to key employees when there's a change of control event so a merger or an acquisition is considered a change of control event."

5. "Section 382, it curbs this practice by limiting the amount of net operating losses that a company can use after the acquisition and that's based on the company's value at the time of the ownership change and this prevents companies from using net operating losses as a tax sheltering tool."

This episode provides a high level overview of several key tax code provisions that can significantly impact the structuring and tax implications of M&A transactions. It highlights the importance of understanding these provisions and working closely with legal and financial advisors to ensure that deals are structured efficiently and in compliance with tax regulations. The detailed explanations, examples, and practical considerations offered in the show are valuable for M&A advisors, business owners, and investors involved in buying or selling businesses.

LEGAL DISCLAIMER: This resource is intended for educational purposes only and does not constitute legal, financial, or tax advice. The information provided herein should not be relied upon for any specific business or financial decision without first consulting appropriate professional counsel. Readers are encouraged to seek advice from qualified attorneys, accountants, or other professionals to address their unique circumstances. Neither the authors nor the publisher assumes any responsibility for actions taken based on the information provided in this resource.