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Oakdale Capital

Chicago, Illinois

Data-driven multifamily investment firm focused on middle-market Class B value-add opportunities, blending institutional discipline with entrepreneurial agility.

AUM

$100mm

Years of experience

18 yrs

Roundtrips

5 roundtrips

Live deals

2

About Oakdale Capital

Oakdale Capital is a data-driven multifamily investment platform focused on middle-market, Class B value-add opportunities across the Midwest and high-growth South/Southeast. The founding team brings nearly 30 years of combined experience with 8,400+ units acquired or developed and $1B+ in transaction volume. Led by Will Thompson (Founder & CEO) and Chris Apostal (Partner & CIO), Oakdale combines institutional underwriting and asset management with entrepreneurial execution. The firm’s integrated capabilities span sourcing, underwriting, construction management, and investor relations, anchored by a proprietary multi-factor “Heatmap + Pinpoint” scoring system that evaluates submarket, neighborhood, and block-group dynamics to identify mispriced assets and reduce uncertainty. Target deals are $10–50M total capitalization, typically 100+ unit communities (1975–2015, with emphasis on well-maintained 1980s vintage). Business plans prioritize light-to-moderate renovations and operational upgrades to drive durable NOI growth, aiming for 16–18%+ net LP IRR, 7%+ stabilized yield, 6%+ average cash-on-cash, and 2.0x+ net LP equity multiples. Current efforts include a live pursuit in Fayetteville, NC, alongside an active pipeline across IN, KY, TN, NC, SC, and TX. Selected track record highlights: Spring Creek Townhomes (136 units, Springfield, IL)—28-month hold, 50.3% gross IRR, 2.7x gross multiple, $3.5M distributions; Pinecrest Apartments (313 units, Bloomington-Normal, IL)—operational turnaround from 79% → 98% occupancy in six months, 27.5% cash-on-cash, 59.5% projected IRR.

Value‑add acquisitions of Class B multifamily (1975–2015 vintage, with 1980s being ideal) and selective ground‑up development where demand demonstrably exceeds supply; complementary focus on student housing and build‑to‑rent; deploys via JV/co‑GP structures with significant GP co‑investment and data‑driven market and asset selection.

Investment focus

Markets

Midwest2/12Southeast4/15Southwest1/4
7 markets

Indiana, Illinois and Texas and 4 Southeastern states.

Real estate types

Multifamily

Team

Will Thompson

Will Thompson

Founder & CEO

Will is the founder of Oakdale Capital and focuses on capital raising, acquisitions, development, asset management, and investor relations. Before founding Oakdale, Will was the Co-Founder and Managing Principal at Fairlawn Capital, where he focused on project underwriting, deal execution, capital sourcing, asset management, ground-up development, project management, construction, property operations, and investor relations. Will personally oversaw the acquisition and development of over $500 million of real estate assets and was a main driver of growing the company to over 5,000 units and 130 employees during his tenure. Will’s real estate background also includes practicing law with a focus on development, financing, and leasing. Will holds a Juris Doctorate from the University of Maryland Francis King Carey School of Law, where he also served Associate Editor of the Maryland Law Review. He also earned an MBA from the University of Illinois at Urbana-Champaign and a BS in Accounting and Finance from Villanova University School of Business. Will played football at Villanova and was a member of the 2009 Division I FCS National Championship team.

Chris Apostal

Chris Apostal

Partner & CIO

Chris Apostal leads Oakdale Capital’s investment strategies across acquisitions and capital markets. With 17 years of experience across institutional platforms and entrepreneurial private equity firms, Chris has developed extensive expertise in real estate investment. Over the past decade, he has focused on multifamily acquisitions, completing $567 million in transactions across eight states. Previously, Chris served as EVP of Acquisitions at Tricap Residential, where he directed investment strategy, built and led the acquisitions team, and closed over $200 million in transactions. Before that, he was a key member of the acquisitions team at The Laramar Group, helping deploy a $500 million fund strategy and completing approximately $237 million in transactions. Earlier in his career, Chris was part of the asset management team at PGIM, overseeing a 70+ asset portfolio spanning all major property types for PRISA, the first open-end core fund and one of the largest in the U.S. Chris holds a degree in Finance with a specialization in Real Estate and Urban Economics from the University of Illinois Urbana-Champaign.

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