Fair market value leases
Lessees operate the equipment under multi-year leases and typically pay insurance and taxes.
Phil Advisors helps families and their advisors with tax-optimized investment strategies to bolster their legacy.
Our story
Wealth advisors incorporate tax strategies into their public investments. Meanwhile, more and more of their clients’ tax bills come from passive income those strategies can’t touch. Business owners and equipment lessors have deducted depreciation against their income for decades. Phil Advisors helps individual investors evaluate the same opportunity.
Direct indexing and long/short tax strategies have drawn large inflows and growing regulatory scrutiny.
Those strategies offset portfolio income, not passive income from private equity, rental property, and other pass-through holdings.
Businesses have deducted equipment depreciation for decades. Most private investors don’t realize they can do the same.
Opportunity
Phil advises clients on commercial equipment leased to creditworthy operators, in transactions sourced and structured by established origination partners. Qualifying equipment is eligible for 100% bonus depreciation, which can offset passive income from rental real estate, private equity interests, and other passive activities in year one.
Lessees operate the equipment under multi-year leases and typically pay insurance and taxes.
This isn’t a fund. You own the equipment directly, one transaction at a time.
Each transaction is sourced by an established equipment finance firm with strong historical credit and residual realization performance.
Phil Advisors is a registered investment adviser and acts as a fiduciary to its clients.
Partner platforms handle accounting and annual tax reporting for each LLC.
Robotics, rail, marine, construction, and trucking assets with consistent demand through economic cycles.
Phil is compensated through advisory fees that are disclosed in each transaction’s documents. Phil never holds title to or custody of the equipment.
Why equipment
Lessees pay monthly rent under a fixed lease. Phil looks closely at the lessee’s credit, the lease terms, and the lessor’s historical performance before recommending a transaction.
At lease end, the equipment may be re-leased, sold to the lessee, or remarketed to a new user. Residual value depends on asset condition, market demand, and economic conditions.
Equipment can be depreciated. How much of that deduction you can use depends on the asset, how the transaction is structured, your own tax position, and limits such as the at-risk and passive activity rules. Phil Advisors does not provide tax or legal advice. Please consult your own tax advisor about how these rules apply to any individual investment.
Equipment vs. real estate
Equipment can be deducted in full in year one. With real estate, only the cost-segregated share of the building can be deducted in the first year. Lease payments are also contractual, so returns depend less on leverage and market conditions.
| Feature | Equipment leasing | Real estate |
|---|---|---|
| First-year deduction | About 100% of cost (bonus-eligible) | About 20–50% of price (cost-segregated components) |
| Deduction basis | Full investment | Building components only |
| Return volatility | Fixed lease payments; residual value is the main variable | Rents, vacancy, cap rates, and exit |
| Leverage | Can deliver market-rate returns without leverage | Typically 60–75% loan-to-value, often with guarantees |
| Income stream | Contractual lease payments from a creditworthy lessee | Rents net of vacancy, operating costs, and capital spending |
| Renewing the deferral | Reinvest at lease end for a new deduction | 1031 exchange or new cost segregation |
| Operating burden | Lessee maintains and insures the equipment | Property management and upkeep |
Real estate ranges reflect typical cost segregation results and vary by property type. Both asset classes are subject to depreciation recapture on sale.
Example transaction economics
Move the slider to the amount you would invest. The example is a representative heavy-duty truck acquisition under a five-year fair market value lease, purchased without financing and eligible for 100% federal bonus depreciation, for an investor who lives in California. Returns are shown after all lessor and advisory fees.
| Equipment cost | $980,392 |
|---|---|
| Placement fees at funding (2%, paid by the LLC) | $19,608 |
| Servicing fees over the lease (1.5% a year) | $42,698 |
| Lease term | 5 years |
| Imputed interest rate | 9.5% |
| Monthly lease payment | $18,666 |
| Booked residual value | $147,059 |
| Projected sale proceeds at lease end | $220,588 |
| Projected net cash return after all fees | $278,929 |
When the lease ends and the equipment is sold, the proceeds can be reinvested in new leased equipment, which may generate a new year-one tax deduction under the same bonus depreciation rules. Sale proceeds are taxable when received, including depreciation recapture, so the benefit of reinvesting depends on the timing and size of the new purchase and your tax situation at that point.
This example assumes the equipment is purchased without financing. Some clients may elect to use financing for part of the purchase price. Because the year-one deduction is generally based on the full cost of the equipment, financing can increase both the projected return and the year-one deduction relative to the cash you invest. Financing also increases risk: loan payments are owed whether or not the lessee pays rent, and losses can exceed your cash invested if you guarantee the loan. Phil can assist clients in reviewing financing terms.
This illustration is provided for informational and educational purposes only. It shows a representative equipment lease transaction based on the assumptions below. It does not represent an actual transaction and is not a guarantee of future results. Actual income, tax deductions, and returns will vary with transaction terms, equipment performance, resale values, individual tax circumstances, applicable law, and other factors.
* This example assumes the investor is a California resident. Tax-equivalent yield is the pre-tax yield a standard, fully taxable financial asset would need to match an illustrative 7% after-tax return on a five-year lease, at a 54.1% combined tax rate: 40.8% federal (the 37% top income tax rate plus the 3.8% net investment income tax) and California’s 13.3% top rate, assuming California tax isn’t deductible on the federal return. For federal tax, the full amount invested is deducted in year one under 100% bonus depreciation (IRC § 168(k)): the equipment cost plus the placement fees, which the LLC pays and capitalizes into the equipment’s cost basis. California doesn’t allow bonus depreciation, so for California tax the equipment is depreciated over its regular recovery period instead. It assumes the investor has enough passive income to use the deductions as they arise. Tax benefits are based on current law, are not guaranteed, and may be limited by the at-risk and passive activity rules. Individual results will vary. Consult your tax advisor.
Projected returns assume a 9.5% implied lease rate, a booked residual value of 15% of equipment cost, and a sale one month after lease end for 150% of booked residual value. They are shown net of lessor fees (a 1.5% placement fee, a 1.0% annual servicing fee on the outstanding receivable, and a 30% share of returns above an 8.25% preferred return) and Phil advisory fees (a 0.5% placement fee, a 0.5% annual servicing fee, and a 10% share of returns above the same preferred return), calculated on monthly cash flows. Dollar figures scale in proportion to the amount invested; the rates of return and the multiple are the same at every amount.
For more on the hypothetical nature of content on this site, see Important disclosures.
Equipment
Buy equipment with bonus depreciation attributes, leased to operators in robotics, rail, shipping, construction, and industry.
Select a category to see example equipment.
Hard assets / 01
Equipment availability and lease terms vary by transaction.
Discuss robotics & automation with PhilHard assets / 02
Equipment availability and lease terms vary by transaction.
Discuss rail with PhilHard assets / 03
Equipment availability and lease terms vary by transaction.
Discuss marine with PhilHard assets / 04
Equipment availability and lease terms vary by transaction.
Discuss construction & mining with PhilHard assets / 05
Equipment availability and lease terms vary by transaction.
Discuss trucking & logistics with PhilHow it works
An origination partner brings a transaction with a lessee lined up. Phil reviews it and sends you a transaction summary.
The origination partner structures the transaction and forms an LLC to buy the equipment. You invest by signing its operating agreement.
The LLC acquires the equipment and then enters into the lease agreement with the lessee. You get a closing statement.
The lessee pays rent, and you get tax reporting each year.
Phil generally favors holding for the long term. When a lease ends or the numbers change, Phil advises whether to keep, re-lease, or sell.
For advisors
Investors with passive income from rental real estate, private equity, and other pass-through holdings can use year-one depreciation to offset that income. For advisors and family offices, Phil reviews each transaction and advises your clients alongside you.
Risks
Investing involves risk, including possible loss of principal. Each transaction should be reviewed separately with your tax and legal advisors.
There’s no public market for these interests. Selling before a lease ends can take time and may require accepting a discount.
If a lessee defaults, the LLC loses its rent and may still have other costs to cover.
Resale and re-lease values depend on demand, the equipment’s age and condition, and changes in technology. They can come in below projections.
Each LLC usually holds one transaction, so a problem with that equipment or lessee affects the whole investment.
Tax benefits depend on current law, which can change, and on your own situation. Under the passive activity rules, deductions you can’t use this year may carry forward instead of reducing this year’s tax.
Clients
Phil advises high-net-worth families, founders, and executives in the innovator economy.
Team
Jeff is an experienced technology entrepreneur, specialty finance investor and wealth advisor. He previously served as CEO of donor advised fund platform NPact and scaled specialty finance and financial technology platforms as an investor at Pine Brook Partners and Tarsadia Investments after beginning his career in the Financial Institutions Group of Goldman Sachs’ Investment Banking Division. He is a graduate, lead case writer and former lecturer at Stanford University’s Graduate School of Business.
Get in touch
Schedule a 30-minute call with Phil Advisors to get started.
Or email admin@philadvisors.com
Our story
Wealth advisors incorporate tax strategies into their public investments. For many of their clients, there is a similar opportunity in passive income that businesses have relied on for decades.
01
Jeff Conn is an experienced private equity investor and operator with a background in specialty finance and wealth technology. He realized he could use his knowledge of equipment leasing platforms and other specialty finance vehicles to offer sophisticated investors with meaningful passive income streams a way to enhance the tax efficiency of their existing portfolio. That idea became Phil Advisors.
02
Over the past decade, wealth advisors and family offices have focused more and more on tax alpha to show value beyond the traditional sources: pre-tax returns, diversification, asset allocation, and manager selection. Large amounts of capital have flowed into tax-aware strategies for the public markets. Direct indexing tracks an index while harvesting losses on individual stocks.
Beta-neutral long/short strategies hold hedged portfolios that earn little market return and exist mainly to defer taxes through ongoing loss harvesting. These strategies have become a crowded trade. Some platforms now limit them to their largest clients, and regulators are scrutinizing the more highly levered versions and those dedicated to shielding active income.
03
Family offices and high-net-worth investors have moved well beyond stock and bond portfolios into private equity, real estate, and other pass-through investments. Their tax liabilities look very different from those of tax-exempt institutions. The IRS treats passive income from these holdings differently from portfolio income, the dividends and capital gains that public-market tax strategies are built to offset.
Passive income sources can include:
Up until this point, there has been no widely utilized investment strategy to defer taxes on passive income with manageable investment risk. Some investors buy asset-heavy businesses, such as laundromats or multifamily buildings, to deduct the equipment inside them. Those deductions aren’t dollar-for-dollar, and they come with leverage, operating, and business-specific risk.
04
The One Big Beautiful Bill Act permanently restored 100% bonus depreciation for qualified property acquired on or after January 19, 2025. It applies by default unless the taxpayer elects out.
For an investor who can use the full deduction against passive income in the year of purchase, the after-tax return on an equipment lease is the same as its pre-tax return, because the tax rate scales every year of cash flow equally. At a 40.8% federal rate, a five-year lease with a 7% after-tax return is equivalent to a fully taxable investment yielding about 11.8%. That is typically the yield on unsecured subordinated debt, which carries far more risk than a lease to a creditworthy lessee underwritten at a conservative residual value.
Illustrative only. Assumes a 40.8% effective federal tax rate and that the investor has enough passive income to use the full deduction in year one. Not a projection of any actual transaction. This information is for general educational purposes only and does not constitute tax, legal, or investment advice. Tax outcomes depend on your individual circumstances, so consult your own tax professional before making any decision based on it.
05
In the leasing industry, fair market value leases, also called tax leases, have long been a secondary product to finance leases. Under a tax lease, the lessor keeps title to the equipment and takes the depreciation deduction. The lessee gets to use the equipment and leaves the resale risk with the lessor. Banks, captive finance companies, and independent lessors have deducted equipment depreciation against their other income for decades. Most private investors haven’t realized they can do the same.
Equipment finance is a $1.3 trillion industry, and most industrial and construction equipment is acquired through financing, with leasing the most common method. Some large family offices have built their own leasing platforms. Most high-net-worth investors have no direct access to the asset class.
06
Phil Advisors advises qualified investors on equipment lease transactions originated by established lessors. It works with advisors serving individuals in the innovator economy, whose tax needs are individual and more complex.
Your clients trust you to spot the opportunities and risks they’re too close to see. A large tax bill on passive income, accepted as the cost of success, is one of them.
How we work with you
Most of your clients’ vendors work in their own lane. CPAs handle filing and compliance, you handle the portfolio, and attorneys handle legal structures. Equipment leasing touches all three, and no one on the team has been asked to evaluate these structures.
The lessor sources and structures each transaction. Phil reviews it and advises your clients alongside you, so you can offer the strategy without becoming an equipment leasing specialist yourself. When you bring it to a client, you’re offering something concrete: a deduction against passive income in year one and contractual lease income for years after.
Partner with Phil
Phil serves as a sub-advisor on each transaction.
Give clients access to equipment leasing alongside their existing portfolio, with an independent review of every transaction.
Every transaction comes with its own offering documents, fee disclosure, and annual tax reporting.
Phil Advisors is a registered investment adviser and acts as a fiduciary to the clients it advises.
Who we work with
The advisors who bring clients new ideas and welcome a second set of eyes are the ones acting in their clients’ interest. Phil is built for those relationships.
Add a tax-aware alternative for clients with passive income from private equity, real estate, and other pass-through holdings.
Help clients with meaningful passive income plan around it, with a deduction based on the full cost of the equipment.
Gain direct exposure to an asset class that other large family offices have built multi-billion-dollar leasing platforms to access.
After a sale, clients often reinvest in private funds and real estate that generate passive income. Leasing provides a potentially safer and more efficient way to offset passive income generated from a business sale.
The investment
Your clients can own commercial equipment leased to creditworthy operators, with a year-one deduction and contractual income for the life of the lease. Phil advises them on each transaction.
Get started
Contact Phil to talk through how equipment leasing fits your clients’ plans and how we can work together.
Phil Advisors advises qualified investors on whether to invest in your tax leases. You keep the origination, servicing, and customer relationship, and earn fees without putting your own capital behind the equipment.
Why partner with Phil
Private investors with passive income are a source of capital that doesn’t depend on bank facilities or warehouse lines.
Earn placement fees, servicing income, and a promote above a preferred return, instead of relying on re-lease and disposition for most of your return.
Acquirers and capital providers generally value recurring fee and servicing income more highly than gain on sale.
The investor vehicle funds the equipment, so your equity and borrowing capacity stay free for the rest of your book.
How a partnership works
Underwrites the credit, documents and closes the transaction, services the lease, and manages the equipment at end of term, including remarketing. It earns a placement fee, servicing income, and a promote above a preferred return.
Becomes the lessor of record. It holds title, funds the purchase without leverage, receives the lease payments and residual proceeds, and passes the depreciation through to its investors.
Advises each investor as a fiduciary on whether a transaction suits them, and keeps the relationship with its clients.
What we look for
Defined lessee credit standards and loss history on comparable transactions.
Equipment with deep secondary markets and long useful lives.
A clear role and incentive to re-lease or sell the equipment at end of term.
Fee terms that reward performance, and a co-investment position where it fits.
Get started
Contact Phil to talk about whether its clients could be a fit for your transactions.