Clear Investment Group

Clear Investment Group

Workforce housing-focused real estate investor

Overview

Clear Investment Group is a Chicago-based real estate investment firm that focuses on acquiring undervalued Class C workforce housing in secondary and tertiary U.S. markets. It revitalizes distressed, mid-size apartment communities through strategic renovations and in-house property management, then stabilizes and sells them to yield-focused investors or holds them long-term. The company differentiates itself through vertical integration (self-managing property, leasing, and construction) and by co-investing its own capital (about 10%) alongside limited partners, coupled with a woman-owned leadership and a history of managing over $600 million in transactions across 150+ properties. Its goal is to provide steady, attractive returns for institutional and private investors by building stabilized, cash-flowing portfolios via opportunistic, value-add investments in workforce housing, funded in part by its funds, including Clear Opportunities Fund I and the planned Fund II.

About Clear Investment Group

Simplify's Rating
Why Clear Investment Group is rated
C
Rated B on Competitive Edge
Rated C on Growth Potential
Rated D+ on Differentiation

Industries

Financial Services

Real Estate

Company Size

11-50

Company Stage

N/A

Total Funding

N/A

Headquarters

Chicago, Illinois

Founded

2021

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Simplify's Take

What believers are saying

  • Clear launched Fund II in March 2025 and raised $30 million by December 2025.
  • The firm closed Fund I at $84 million after $600 million historical transactions.
  • 2026 messaging emphasizes below-threshold rents and workforce-housing demand in Midwest markets.

What critics are saying

  • Syracuse sued Clear in April 2025 over Skyline Apartments; repairs end April 30, 2026.
  • Clear faces recurring code-violation and receivership pressure at 352-unit Skyline Apartments.
  • A failed Skyline remediation could trigger a receiver, crushing lender and LP confidence.

What makes Clear Investment Group unique

  • Amy Rubenstein founded the firm in 2003 and still leads Clear in 2026.
  • Clear targets distressed workforce housing below replacement cost, not luxury repositioning.
  • Vertically integrated leasing, construction, and management keep execution control in-house.

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Benefits

Health Insurance

Dental Insurance

Vision Insurance

Paid Vacation

Paid Holidays

401(k) Retirement Plan

Performance Bonus

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