Cherif Medawar — Deep Dive
Investor · Fund Manager · Author · Educator · 35+ years in CRE. Founder of CMREI. Largest individual owner of historic commercial property in Old San Juan, Puerto Rico. Co-author of Successonomics with Steve Forbes.
The FACTS System™
Medawar’s patented, step-by-step commercial real estate investing framework. First revealed in Blue Ocean Opportunities in Commercial Real Estate. Applicable to all 12 commercial property types regardless of investor background or capital.
F
Find the deal
Locate off-market and undervalued commercial properties — vacant, distressed, or overlooked. Medawar’s edge: he goes where others won’t.
A
Analyze & calculate
Run the numbers: NOI, cap rate, cash-on-cash return, debt service. Never speculate — every deal must pencil out before you move.
C
Control the deal
Secure the property under contract creatively — options, seller financing, joint ventures — before you have all the capital.
T
Time due diligence
Use the contract period strategically: inspect, arrange financing, verify zoning, confirm tenant viability. Timing is a competitive advantage.
S
Strategize
Manage to highest and best use. Reposition, improve tenant mix, add value. „The money is in the structure“ — asset management is wealth creation.
Core philosophy behind FACTS
Medawar designed FACTS to demystify CRE for investors at any level. The system is sequential but not linear — each stage informs and refines the others. The controlling insight: most investors fail not at finding deals but at structuring them. FACTS forces the structure question first, before capital is committed.
Key differentiator: „The money is in the structure“
Medawar’s most repeated principle. A mediocre property with a brilliant structure (creative financing, right entity, right tax position) outperforms a great property with a poor structure every time. This is why he teaches SEC fund formation, syndication, and JV partnerships alongside deal-finding — the wrapper matters as much as the asset.
Book · 2013
Blue Ocean Opportunities in Commercial Real Estate
Medawar’s landmark book argues that CRE is the investment vehicle of the wealthy — and that the ocean of commercial deals is blue (uncontested) compared to the red ocean of residential investors fighting over the same single-family homes.
12
Property types covered
$100M+
Medawar’s portfolio built
1989
First deal (duplex, CA)
The „Blue Ocean“ metaphor
Borrowed from Blue Ocean Strategy, Medawar applies it to investing: residential real estate is a red ocean — millions of investors fighting over the same houses with razor-thin margins. Commercial real estate is a blue ocean — fewer competitors, larger deals, income driven by business fundamentals rather than speculation, and long-term NNN leases that deliver passive income. One deal can generate more wealth than a dozen residential flips.
Why CRE vs residential — Medawar’s core argument
Commercial properties are valued by income (NOI ÷ cap rate) rather than comparables, giving investors direct control over value through management. Tenants sign longer leases and often cover operating expenses (triple net). Lenders evaluate the asset, not just the borrower. And the investor pool is far thinner — meaning better negotiations, better terms, better returns. Medawar’s thesis: you don’t need more deals, you need bigger deals.
Origin story — the billionaire mentor
Working at the Century Plaza Hotel in Los Angeles in the early 1980s, Medawar was approached by Edmond Baysari, an international billionaire, who noticed his work ethic. Baysari employed Medawar for roughly eight years, exposing him to multi-million-dollar real estate and securities transactions. That mentorship shaped everything — including Medawar’s own mentorship model of „pulling investors aside“ and sharing what he learned, just as Baysari did for him.
MIGSIF — the fund born in a recession
In August 2009, at the depth of the financial crisis, Medawar filed his first real estate fund (MIGSIF) with the SEC under Regulation 506(b). His point: the best opportunities emerge in downturns. Vacant standalone buildings — which others avoid — are where the most profitable deals live. A second fund followed in 2015 under 506(c). His students learn to replicate this fund-manager model under SEC compliance.
Successonomics · Chapter 2
12 Steps to Financial Freedom
Medawar’s contribution to Successonomics (co-authored with Steve Forbes and Celebrity Experts®, 2014). The chapter maps a three-stage evolution of wealth. Click each stage to expand.
Steps 1–5
Stage 1 — You work for the money
1
Education — academic, professional, and crucially financial. The knowledge effect: you cannot act on what you don’t understand.
2
Corporate employment — stable income, exposure to systems, structure, and process. Build skills, network, and understanding of how organizations create value.
3
Leadership — learn to manage yourself, then others, then projects. Leadership capacity determines how large a business you can eventually build.
4
Saving — put money aside consistently each month. Savings are the seed capital and buffer that make every subsequent step possible.
5
Build credit — personal and business. Credit is the mechanism by which other people’s money becomes your tool.
Steps 6–7
Stage 2 — You work the money
6
Invest — deploy capital into income-producing assets. Medawar’s preferred vehicle: commercial real estate. Actively manage investments, select deals, structure transactions.
7
Build a business — create systems that generate income independently of your daily labor. A business is a leveraged entity; it multiplies your time.
Steps 8–12
Stage 3 — The money works for you
8
Passive income streams — NNN leases, fund distributions, royalties, dividends. Income that arrives regardless of your daily activity.
9
Tax strategy & asset protection — LLCs, corporations, trusts, cost segregation, depreciation. Without this, you earn and immediately lose a large share to tax.
10
Fund / syndication management — raise capital from investors under SEC compliance to do larger deals than personal capital allows. You become the sponsor.
11
Legacy and generational wealth — family trusts, estate planning, transferring assets to the next generation in tax-efficient structures.
12
Philanthropy and contribution — giving back as both a moral commitment and a strategic act. The completion of the wealth cycle.
Successonomics — the broader compilation
The book, published by Celebrity Press and co-headlined by Steve Forbes, assembles 37 chapters from leading entrepreneurs and advisors. Its thesis: success combined with economic competence (Successonomics) is the formidable combination most people miss. Kevin Harrington (original Shark Tank investor) called it a „blueprint people can use to achieve their financial goals.“ The Celebrity Experts® framework highlights six shared success traits: perseverance, passion, planning, risk-taking, decision-making, and — above all — action.
Cherifisms — core principles
The term coined by Medawar’s students for his philosophical sayings, strategic guidelines, and mindset axioms. These form the connective tissue of all his teaching.
„Just one deal can change your life.“
„The money is in the structure.“
„You can have all the money in the world, but without a clear strategy, you’ll lose it. Build your blueprint first.“
„Fundraising is about relationships. Understand your investor’s goals, fears, and motivations.“
„Earn while you learn.“ — The philosophy behind all CMREI educational programs; Medawar’s students invest alongside him in real transactions.
„Ongoing asset management and market analysis are just as critical as the initial underwriting.“
„Communicate openly and frequently with investors, especially when things don’t go as planned.“
„Most people get stuck at one level and become unaware or unable to grow further.“
„Life is a game to be played — grab the opportunities and overcome challenges that would otherwise stop you.“
Mindset pillars behind the Cherifisms
Three interlocking beliefs run through every Cherifism: (1) Action beats analysis paralysis — the investors who succeed are the ones who move, even imperfectly. (2) Structure precedes capital — figure out how the deal is wrapped before you worry about whether you have the money. (3) Relationships are the real asset — deals, financing, and investors all flow from trust built over time.
The 12 Commercial Property Types
Medawar’s Commercial Real Estate Roundtable (CRERT) covers all 12 types of CRE — a scope no other educator has assembled in a single training. Each type has distinct underwriting, financing, and management logic.
Apartment buildings
Multifamily; value driven by rents and occupancy. Entry point for many CRE investors upgrading from residential.
Single-tenant retail
NNN leases with national tenants. Highly passive; lease length creates bond-like income stream.
Mixed-use
Retail/office below, residential above. Multiple income streams reduce vacancy risk. Medawar’s Puerto Rico portfolio is predominantly this type.
Hotels / hospitality
Medawar holds a patent-pending hospitality investing system. High upside but operationally intensive.
Office buildings
Tenant creditworthiness and lease length are key metrics. Post-2020 repositioning opportunity as remote work shifts demand.
Retail centers / strip malls
Anchor-tenant strategy drives foot traffic for smaller tenants. Location and co-tenancy clauses are critical.
Gas stations
Niche but high-margin if environmental liabilities are managed. Medawar teaches full environmental diligence protocols.
Mobile home parks
Affordable housing demand + land ownership model = recession-resilient. One of the highest cap-rate CRE categories.
Assisted living facilities
Demographic tailwind from aging populations. Licensing and regulatory complexity are the main barriers to entry.
Industrial / warehouse
E-commerce boom increased demand. Long leases, low management intensity, strong tenant covenants.
Land development
Highest risk, highest upside. Entitlement strategy and municipal relationships determine value creation.
Self-storage
Recession-resistant, highly scalable, low staffing requirements. One of the most consistent income-generating CRE categories.
Practical application — what to do with this
Medawar’s entire framework is designed to be actionable, not theoretical. Here is how the pieces connect into a practical wealth-building sequence.
Step 1 — Locate where you are in the 12 steps
Medawar’s primary diagnostic: most people stall because they try to skip stages. Identify your current stage honestly. The sequence is not arbitrary — each step creates the conditions for the next.
Step 2 — Apply FACTS to your first target property type
Select one of the 12 property types that fits your market and capital position. Run FACTS: where are the deals in your city? Do the numbers work? Can you control one before you have all the capital? What is your due diligence timeline? How will you manage it to highest and best use?
Step 3 — Structure before capital
Before approaching any lender or investor, determine the right entity (LLC, LP, corporation), the right financing mix (bank debt + seller carry + equity partners), and the right exit or hold strategy. Investors who present structure first raise capital more easily.
Step 4 — Build the capital stack creatively
For larger CRE deals, Medawar’s stack often includes: senior bank debt (50–65%), a subordinated layer (seller carry, mezzanine, or a silent partner), possible guarantee instruments, and equity from a fund or syndication under Regulation D (506b or 506c).
Step 5 — Manage relationships as systematically as assets
Medawar’s investors stay loyal across multiple deals because of communication discipline: regular updates, proactive disclosure when plans shift, and consistent delivery on stated returns. Build an investor CRM. Document every commitment. Report on schedule.
The „Earn While You Learn“ model
Medawar’s distinguishing pedagogical offer: students invest alongside him in real transactions through his JV Partner Program and fund vehicles. This creates a direct economic incentive to apply what is learned, and generates a feedback loop of practical experience that purely academic programs cannot replicate.