who we are

If we can’t make it better, we don’t get involved.

Oakdale Capital is an entrepreneurial real estate investment firm that leverages institutional expertise and data analytics for the acquisition and improvement of rental housing.

Oakdale Capital

Our leadership

Will Thompson, JD / MBA

Founder & CEO

Will sets the strategic direction for Oakdale Capital and oversees the firm's investment activities, capital raising, investor relations, and external communications. His background as a real estate attorney and private equity founder informs Oakdale's disciplined, performance-focused approach.

Chris Apostal

Partner & CIO

With expertise in acquisitions and asset management at institutional platforms (e.g. PGM and the Laramar Group) as well as entrepreneurial private equity firms, Chris leads Oakdale Capital's investment strategies across acquisitions and capital markets.

Our Team

Aron Whitaker

SVP Construction

20+ years of experience in multifamily construction, renovations, and development.

Prior to joining Oakdale, Aron held similar roles at Tricap Residential and Buckingham Co. Aron attended IU Indianapolis and is married with five children. Outside of work, he enjoys spending time outdoors with his family

Vincent Menechino

VP Acquisitions

12+ years of institutional RE experience in acquisitions and asset management.

Prior to joining Oakdale, Vinny held similar roles at Sentinel Real Estate, Tricap Residential, AFI, and Cardinal Group Finance degree (Bentley University) and Masters of Real Estate (Fordham)

What to Know About Us

Resourceful

in approach.

Rigorous

in process.

Resourceful

in approach.

Rigorous

in process.

Patient

in strategy.

Relentless

in execution.

Patient

in strategy.

Relentless

in execution.

Disciplined

in analysis.

Bold

in conviction.

Disciplined

in analysis.

Bold

in conviction.

Ambitious

in outcomes.

Genuine

in relationships.

Our Core Strengths

Property Selection & Underwriting

A data centered selection process grounded in top-down market analysis and granular evaluation of micro-location/property characteristics. Each acquisition is underwritten with a focus on downside protection, realistic capital planning, and disciplined entry pricing.

Deal Sourcing

Longstanding and deep relationships with brokers, owners, and lenders across our target markets provide consistent access to differentiated and often off-market opportunities.

Deal Sourcing

Longstanding and deep relationships with brokers, owners, and lenders across our target markets provide consistent access to differentiated and often off-market opportunities.

Capital Structuring & Alignment

Prudent leverage, thoughtful structuring, and transparent reporting aligned with long term stewardship of investor capital.

Capital Structuring & Alignment

Prudent leverage, thoughtful structuring, and transparent reporting aligned with long term stewardship of investor capital.

Active Asset Management & Execution

Hands on oversight of asset operations and capital execution spanning light and heavy value add, repositioning, adaptive reuse, and selective ground up development, demonstrating experience across diverse business plans.

Construction & Project Management

Integrated oversight ensuring quality, budget discipline, and timely delivery of business plans.

Construction & Project Management

Integrated oversight ensuring quality, budget discipline, and timely delivery of business plans.

Join Our Team

Oakdale Capital is growing, and we’re looking for highly motivated and talented team members. With competitive salaries, a family-oriented environment, great benefits with opportunities for advancement, we could be the right fit for you.

Keep up with Oakdale

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Oakdale Capital

1222 W Oakdale Avenue

Chicago, Illinois 60657

Oakdale @ 2025. All rights reserved.

Past performance is not indicative of future results. Any reference to performance reflects historical data as of the stated date and may include both realized and unrealized investments.

Certain statements herein may constitute forward-looking statements and involve known and unknown risks, uncertainties, and other factors that may cause actual results to differ materially.

Keep up with Oakdale

Subscribe to our newsletter for the latest updates

Oakdale Capital

1222 W Oakdale Avenue

Chicago, Illinois 60657

Oakdale @ 2025. All rights reserved.

Past performance is not indicative of future results. Any reference to performance reflects historical data as of the stated date and may include both realized and unrealized investments.

Certain statements herein may constitute forward-looking statements and involve known and unknown risks, uncertainties, and other factors that may cause actual results to differ materially.

Keep up with Oakdale

Subscribe to our newsletter for the latest updates

Oakdale Capital

1222 W Oakdale Avenue

Chicago, Illinois 60657

Oakdale @ 2025. All rights reserved.

Past performance is not indicative of future results. Any reference to performance reflects historical data as of the stated date and may include both realized and unrealized investments.

Certain statements herein may constitute forward-looking statements and involve known and unknown risks, uncertainties, and other factors that may cause actual results to differ materially.

Keep up with Oakdale

Subscribe to our newsletter for the latest updates

Oakdale Capital

1222 W Oakdale Avenue

Chicago, Illinois 60657

Oakdale @ 2025. All rights reserved.

Past performance is not indicative of future results. Any reference to performance reflects historical data as of the stated date and may include both realized and unrealized investments.

Certain statements herein may constitute forward-looking statements and involve known and unknown risks, uncertainties, and other factors that may cause actual results to differ materially.

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