Complex situations.
Structured paths.

The Situation

A software founder had sold a company two years prior and was running a second venture still in early growth mode. His personal tax returns showed nominal income — most distributions were retained in entities, and a portion of the prior-year gain had been sheltered through a qualified opportunity zone investment. On paper, he looked like he could not afford a mortgage. In reality, his business had gross receipts averaging $300K per month — making him extremely well qualified through an alternative investor's lens.

The Challenge

Three conventional lenders and his primary bank had declined or stalled — all focused on the two-year average of Schedule C income, which produced a qualifying income figure far below what the loan required. The purchase was time-sensitive: the seller had accepted a backup offer contingent on a 28-day close.

The Structure

We bypassed tax returns entirely and qualified using 12 months of personal and business bank statements, which clearly reflected the borrower's actual cash flow. A portfolio lender with appetite for high-asset, low-documented borrowers was identified within 48 hours. The loan was structured at 65% LTV — a deliberate choice that reduced the lender's risk profile and accelerated underwriting approval. We closed in 21 days.

"Every lender focused on what I could not show them on paper. Gabe focused on what I could — and we closed on a property I had wanted for two years."

Randy H. — Software Founder, Coastal California

The Situation

A retired CFO and his wife had purchased their primary residence outright a decade earlier. With a significant renovation underway, their wealth advisor recommended accessing equity through a cash-out refinance rather than liquidating from a concentrated equity portfolio at an inopportune time. The advisor referred them directly with a clear mandate: do not disrupt the investment posture.

The Challenge

The couple had no earned income — Social Security, a modest pension, and portfolio distributions covered living expenses well, but produced a qualifying income figure that fell short of conventional jumbo guidelines by a wide margin. A standard bank had offered a product, but required they move $4M of assets under management to qualify, which the advisor found unacceptable.

The Structure

We used an asset depletion methodology: eligible liquid assets — retirement accounts, brokerage holdings, and cash reserves — were amortized over a defined period to produce a qualifying monthly income figure. No assets were liquidated, no portfolio was moved. The loan was structured as a 10-year interest-only ARM aligned with their estate and distribution timeline. The wealth advisor remained the primary relationship throughout; we coordinated every step around their planning framework.

"Gabe understood exactly what we were trying to protect. He coordinated with our advisor and kept the process entirely off our plate."

Jim R. — Retired Executive, Montecito, CA

The Situation

An active real estate investor with a portfolio of six properties came to us with a seven-day window. A distressed multi-unit property in a desirable coastal market had surfaced through a private network — priced meaningfully below replacement cost — with the seller requiring proof of funds and a fast close. Her capital was deployed: equity in existing properties, a business account with restricted funds, and a 1031 exchange in progress.

The Challenge

No conventional lender could move in seven days. Her existing bank had a 45-day minimum for investment property origination. The 1031 funds could not be accessed without triggering a tax event. She needed a short-term bridge against the acquisition property that could be refinanced cleanly once the asset was stabilized — without tying up personal income documentation in the process.

The Structure

We arranged a $3.5M short-term bridge loan through a private capital source, secured against the acquisition property, with the exit strategy mapped from day one: a DSCR refinance once the property was leased and cash-flowing. Because the loan qualified on the property's projected debt-service coverage ratio rather than the borrower's personal income, underwriting moved quickly and cleanly. The loan was originated in the name of her LLC, preserving entity structure throughout. Funds were available in 11 days. The DSCR refinance closed seven months later as planned.

"The deal would have been gone without a lender who understood how to move quickly and structure around the entity. This is exactly the kind of problem Gabe solves."

Jesse D. — Real Estate Investor, Santa Barbara County

The Situation

A woman in her early 70s was ready to downsize following the death of her husband — moving closer to her children and longtime friends. Her estate attorney referred her to us with a clear set of priorities: purchase the new home without liquidating assets, avoid triggering capital gains on her concentrated investment portfolio, keep everything inside her existing revocable trust for continued tax protection, and preserve capital for the obligations ahead — covering future capital gains liability, ongoing charitable gifting, and providing a partial early inheritance to her three adult children. The proceeds from the sale of her departure residence would replenish her liquidity once it closed, but she needed to move first.

The Challenge

The financial picture was strong but entirely illiquid in the short term. Her portfolio could not be touched without triggering capital gains she had carefully deferred. The departure residence was not yet listed. Conventional lenders had no mechanism for bridging this gap cleanly, and most required personal title at close — a non-starter given the estate structure. The trust had to remain on title throughout, with no post-close assignment, to preserve the layered tax protections her attorney had built over decades.

The Structure

We coordinated a two-part structure. First, a portfolio line of credit secured against her investment accounts provided the funds to close — preserving every position in the portfolio and triggering no capital gains event. That line would be repaid in full upon the sale of her departure residence. For the takeout financing, we structured a permanent loan using asset depletion methodology, qualifying her on the depth of her balance sheet rather than earned income — leaving her capital fully intact to address the capital gains exposure, charitable commitments, and early inheritance transfers her attorney had planned. Throughout, title remained in the name of her trust. We identified a portfolio lender experienced with complex trust documents, engaged their legal team at the outset, and closed in 28 days with the trust on title from day one — no disruption to the estate plan at any step.

"This was one of the most thoughtfully coordinated mortgage transactions I have been a part of. Gabe understood every layer of the estate plan and structured the financing to protect all of it — the trust, the portfolio, the tax position, and our client's peace of mind during an incredibly difficult time."

Brendan D., J.D. — Santa Ynez, CA

The Situation

A man in his late 60s came to us following the death of his 90-year-old father. He had lived with and cared for his father in the family condo until the end, and his father had died leaving an estate held in a now-irrevocable trust — comprising a $5M investment portfolio, the condo they had shared, and a four-unit rental property. His two sisters were named co-beneficiaries and wanted to be liquidated out of all holdings. The son wanted to retain the condo as his primary residence — critically, inheriting his late father's 30-year-old property tax base under Proposition 19 — and to buy out his sisters' shares of the rental building and continue operating it as an income-producing asset. He was retired, with roughly $2M in personal assets prior to inheritance.

The Challenge

The estate was now irrevocable — which meant the assets were locked inside the trust and could not simply be redistributed without a financing mechanism to make the sisters whole. The son could not sell the condo to satisfy them without losing both his home and the tax base he stood to inherit — a generational financial advantage that, once surrendered, could not be recovered. Any lender willing to finance against the condo would need to lend directly to the irrevocable trust with a personal guaranty from the son, the precise structure required to preserve the Prop 19 step-up. Most lenders will not touch an irrevocable trust. On the rental side, the son had no earned income — ruling out conventional qualification — but the property had strong in-place cash flow.

The Structure

We executed two loans simultaneously. For the condo, we identified a portfolio lender willing to lend against the irrevocable trust with the son's personal guaranty — the only structure that preserved the Prop 19 tax base and kept title exactly where it needed to be. For the four-unit rental, we placed a DSCR loan qualifying solely on the property's rental income, with no reliance on the son's personal income or assets. Together, the two loans generated sufficient proceeds to make both sisters whole on their respective inheritances and bring the estate settlement to a clean close. A delicate situation, handled with ease.

"I had no idea a lender would even consider this structure. Gabe understood what was at stake — the tax base, the trust, the family dynamic — and found a way to make everyone whole without my father's legacy being dismantled piece by piece."

Alan D. — Estate Beneficiary, Westlake Village, CA