Ryan Cockerill

Private Real Estate Investor

Founder of 101

Contact

I am founder and managing director of 101 and serve as an independent director to relationship family offices and private firms. I love net-lease real estate. Over 17 years, $4B+ acquired, 2,000+ properties, and roughly 36,000 hours in the asset class gave me the opportunity to build something unique.

I built 101co.com to invest in the highest quality net leases available in the market and plan on doing it until I die.

“Ryan lives, eats, dreams, and breathes net lease real estate. He has almost seen as many deals as I have.”

Chris

National broker, closed $42B+ of net lease transactions

“Ryan is one of the hardest workers I know and is obsessed with where he focuses his attention – both in work and his family.”

Adam

Best man at our wedding

principles

Core Investment Principles I Live By

Capital preservation first

Return of capital comes before return on capital. If a decision forces me to choose between protecting downside or reaching for yield, I choose downside protection. We all take small speculative shots, but the material portion of my net worth is invested in durable, cash‑flowing assets.

Buy with a margin of safety

I want to own assets below realistic replacement cost, with durable tenancy and conservative capital structures. Price is what you pay; risk is what you keep.

"Margin of safety (in real estate) = below‑market rent or a cost basis at a structural discount to intrinsic value."

Boring works

I don’t change strategy to chase what’s fashionable. I stay within the circle of things I can underwrite with hard market data and intrinsic fundamentals.

Alignment and skin in the game

I invest my own capital alongside partners. I don’t ask anyone to take risks I wouldn’t willingly take myself.

Simple beats complex

I prefer net leases, straightforward structures, and businesses I can explain in a sentence. Minimal operational risk, minimal capital expenditure risk, and sleep‑well‑at‑night monthly cash flow. If it doesn’t make sense, I don’t invest.

Long‑term perspective

I care more about the compounding of quality cash flows over decades than the next quarter’s quick buck.

story

My Story & Scars

I have been in net lease real estate for over 17 years. I passed 10,000 hours in 2015 and am now round 36,000 hours. Early on, I chased deals that looked good on paper and learned the hard way that tenant quality, market, lease structure, and basis matter far more than flashy pro forma IRRs.

Some of the lessons:

Chasing yield

On paper, an extra 200 bps of yield over a long horizon looks attractive. In reality, higher yield in net lease usually means more risk: questionable credit, inferior real estate, or eroding demographics. Those factors do not deliver yield when your lease expires or your tenant cannot pay the rent.

Swimming against the current

It is easier to “find opportunities” in secondary or tertiary markets, or with weaker operators, because there is less competition. A few people make that work. Most end up with vacant boxes, no backfill, and suspended distributions.

Knowing what you can control

Tenants have their own goals. Competition comes to town. Relationship managers leave. There are limitless variables you cannot control. Cost basis is one of the few you can. It must solve the unsolvable.

Those lessons pushed me toward a narrower, more disciplined approach: net lease assets with strong fundamentals, conservative leverage, and a bias toward boring, predictable cash flow.

strategy

How I Think About Risk

Every investment has risk. The job is to eliminate as much as possible, understand what remains, price it appropriately, and have a basis that keeps you safe if things do not go as planned.

Tenant risk

Who is on the other side of the lease, and how durable is their business model through cycles? If the tenant moves or fails, what is the ideal backfill or use? I focus on proven operators and real estate that will always have demand.

Lease risk

In net lease, you are buying a contractual cash flow. Rent, term, and guaranty matter, but so do assignment clauses, landlord and tenant responsibilities, and termination rights that change true economics. I prefer enforceable clauses, clear tenant responsibilities with minimal to no landlord obligations, and no unpriced tenant outs.

Location and residual risk

Over a long enough horizon, all businesses change or die, and tenants will come and go. The question is: what is this building worth then, who else can use it, and at what rent? I underwrite default and re-tenant scenarios on every opportunity.

Capital structure risk

Good real estate with bad debt is bad real estate. I favor fixed terms you can underwrite, with clean maturity optionality under conservative assumptions.

Operational and alignment risk

Controls, reporting, best‑in‑class service providers, and incentive structures matter as much as the assets. I invest and implement clear governance, clean books, and fair economics that align partnerships.

If I can’t explain the key risks and how I plan to mitigate them in plain language, I don’t do the deal.

materials

Content & Research

I share occasional long‑form pieces for current and prospective partners. Selected topics include:

  • The Depreciation Advantage 101

  • Real Estate Fundamentals 101

  • Compounding in a Quarterly Reporting World

All materials are educational in nature and are not an offer to sell or a solicitation to buy any security.

partners

Who I Work With

• Relationship family offices, RIAs, and wealth managers with typically $300M+ AUM
• Partners allocating $1M per position who value downside protection and predictable cash flow over trend‑chasing