Financial Strategy & Capital Advisory

Senior counsel for complex capital decisions.

Woolery Advisory provides institutional-grade financial modeling, valuation, and strategic guidance to private equity sponsors, family offices, and operating companies navigating high-stakes transactions.

$900M+
Mortgage Debt Underwritten
$400M+
Portfolio Under Management
$54M+
Tax-Exempt Bonds Closed
20+
Years of Advisory Experience
Start a Conversation View Services
About

Experience that spans the full capital stack.

Russ Woolery is the Managing Director of Woolery Advisory LLC, a Brentwood, Tennessee-based financial advisory practice serving corporate and family office clients across real estate, private equity, manufacturing, alternative energy, and healthcare.

With more than two decades of experience across investment banking, commercial real estate finance, private equity, and structured finance, Russ brings institutional depth to situations that demand it — whether that means building a three-statement model from scratch, stepping in as interim CFO, closing a tax-exempt bond financing, or guiding a management team through an M&A process.

Prior to founding Woolery Advisory, Russ held senior roles at Berkadia Commercial Mortgage (underwriting $900M+ in GSE debt), Addicus Private Equity (portfolio management for a $400M diversified portfolio), RiskSpan (structured finance advisory across $30B in transactions), and in public finance at Oppenheimer, Northland Securities, and Dougherty & Company.

Education
MBA — Finance & Accounting
Kelley School of Business, Indiana University
Undergraduate
B.S. — Finance, Marketing & International Business
Indiana University, Bloomington
Asset Classes
Real estate · Private equity · Municipal finance · Structured finance · Manufacturing · Alternative energy · Healthcare · Higher education
Instruments
Senior mortgage debt · GSE executions (Fannie Mae, Freddie Mac, HUD) · Tax-exempt bonds · Mezzanine debt · Private placements · Interest rate swaps · PE fund reporting
Location
Brentwood, Tennessee · Available remotely nationwide
Services

What we do.

Engagements are structured around your specific situation — from one-time transaction support to ongoing retained advisory arrangements.

01
Financial Modeling & Valuation
Dynamic three-statement models, DCF and yield analysis, sensitivity toggles, stress-case scenarios, and covenant analytics built to institutional standards and reviewed for decision-making use.
02
Private Equity Advisory
Portfolio KPI monitoring, budget variance review, liquidity tracking, and investor reporting. Transaction-level due diligence, proforma evaluation, and underwriting support for new investments.
03
Real Estate Finance
Sizing, structuring, and underwriting of senior mortgage debt across Fannie Mae, Freddie Mac, HUD, and private placements — including bridge, forward, mezzanine, and re-syndication executions.
04
Capital Markets & Debt Placement
Tax-exempt and taxable bond placement for investment-grade and non-rated borrowers, including municipal, healthcare, senior housing, education, alternative energy, and tribal clients.
05
Interim CFO Services
Fractional and interim CFO engagements covering budgeting, operating cost management, capital raising, environmental liability oversight, and pricing strategy for operating companies.
06
M&A Due Diligence & Integration
Operational assessments, synergy analysis, and integration planning for domestic and international transactions. Senior-level counterparty management through closing and post-close stabilization.
Experience

A career built at the intersection of markets and operations.

2011 – Present Brentwood, TN
Managing Director
Woolery Advisory LLC
Financial modeling, valuation, and strategic advisory across real estate, manufacturing, alternative energy, and healthcare. Served as interim CFO for a 600-ton/day landfill facility. Closed $54M+ in tax-exempt bonds and $100M+ in first mortgage loans. Led due diligence on four international M&A transactions ($7M–$175M).
AdvisoryModelingCapital MarketsCFOM&A
2023 – 2026 Oxford, MS (Remote)
Private Equity Associate
Addicus Private Equity
Portfolio management for a $400M diversified real estate and operating company portfolio. Served as primary management team contact, providing strategic guidance and value-creation recommendations. Closed three single-asset PE transactions totaling $37M. Developed standardized underwriting frameworks adopted firm-wide.
Private EquityPortfolio MgmtUnderwriting
2016 – 2023 Brentwood, TN
Senior Real Estate Analyst
Berkadia Commercial Mortgage
Underwrote and structured $900M+ in senior mortgage debt across Fannie Mae, Freddie Mac, HUD, and private placements — including bridge, forward, mezzanine, and re-syndication executions. Built dynamic credit models with sensitivity and stress-case analytics adopted company-wide.
GSECMBSHUDBridge Debt
2013 – 2016 Vienna, VA (Remote)
Senior Consultant
RiskSpan, Inc.
Cash-flow modeling, legal documentation review, and controls testing for ~2,100 structured finance transactions ($30B par). Validated credit risk and stress-testing models for a global rating agency.
Structured FinanceRating AgencyABS
2005 – 2011 Minneapolis, MN
Vice President – Public Finance
Dougherty & Company · Northland Securities · Oppenheimer & Co.
Led underwriting and financial advisory for 20+ financings across healthcare, senior housing, education, energy, and municipal clients. Structured $86M in energy savings revenue bonds for the Commonwealth of Pennsylvania and $180M in total financings at Dougherty.
Muni BondsTax-ExemptHealthcareEnergy
Track Record

Selected metrics across a 20-year career.

$900M+
Senior mortgage debt underwritten across Fannie Mae, Freddie Mac, HUD, and private placements
$400M
Real estate & operating company portfolio managed at Addicus Private Equity
$30B
Structured finance transactions reviewed and modeled at RiskSpan across ~2,100 deals
$54M+
Non-rated tax-exempt bond issuances closed through Woolery Advisory
$175M
Largest single M&A transaction led — four international deals ranging $7M to $175M
$37M
Single-asset private equity transactions closed at Addicus across three deals
$86M
Energy savings revenue bonds structured for the Commonwealth of Pennsylvania
600T/day
Landfill facility capacity managed as interim CFO over a three-year engagement
Contact

Let's discuss your situation.

Engagements typically begin with a brief introductory call. Whether you need transaction support, an ongoing modeling partnership, or a senior advisor to sit alongside your team, Woolery Advisory structures around what you actually need.

Location Brentwood, Tennessee
Available remotely nationwide