#314: The 5-Point Framework For Evaluating Passive Investments, Building Investor Relationships, and 2026 Opportunities with Spencer Hilligoss

In this episode of the Multifamily Wealth Podcast, we sit down with Spencer Hilligoss of Madison Investing, for a tactical and transparent conversation on how passive investors should evaluate deals, vet sponsors, and position their portfolios for 2026.

Spencer brings a rare dual perspective, having personally invested across dozens of passive deals and raised capital from multiple LPs. Together, Axel and Spencer break down what has changed in the last few years, where many investors went wrong, and what actually matters when building long-term wealth through multifamily and alternative assets.

The conversation focuses on frameworks, capital stack awareness, downside protection, and relationship-driven capital formation—all especially critical in today’s post-2022 market environment.

If you’re a passive investor trying to invest smarter or a sponsor looking to raise capital the right way, this episode offers practical, hard-earned insight from both sides of the table.

Join us as we dive into:

• Spencer’s journey from tech leadership into passive real estate investing
• Why owning rentals with property management is still not truly passive
• The 5-point framework Spencer uses to evaluate sponsors and deals
• Why strong track records from 2020–2022 can be misleading
• The importance of understanding debt, capital stacks, and preferred equity
• Why many investors misunderstand whether they’re investing for cash flow or growth
• How Spencer organically built an LP base through trust and relationships
• What types of deals and structures are most attractive heading into 2026
• Why conservative projections often outperform aggressive underwriting

Are you looking to invest in real estate, but don't want to deal with the hassle of finding great deals, signing on debt, and managing tenants? Aligned Real Estate Partners provides investment opportunities to passive investors looking for the returns, stability, and tax benefits multifamily real estate offers, but without the work - join our investor club to be notified of future investment opportunities.

NH Multifamily Fund III Details:

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Learn more about Aligned Real Estate Partners

Connect with Spencer:

Follow him on Instagram
Connect with him on Linkedin
Learn more about Madison Investing