Real-world asset tokenization promises something the traditional financial system has always struggled to deliver: fractional, liquid access to private market investments that were previously reserved for institutions and accredited investors with deep pockets and the right connections. A tokenized commercial real estate deal on StartEngine or Securitize is, at its best, a genuine democratization — smaller check sizes, on-chain transparency, and the possibility (if not the guarantee) of a secondary market. At its worst, it’s a paper token backed by nothing more specific than “a portfolio of assets” described in a PDF with no independent verification.
The Teshy community has reviewed hundreds of RWA raises across StartEngine, tZERO, Wefunder, Republic, Realio, NetCapital, and Securitize. Most are fine. Some are excellent. A small number have structural problems that should disqualify them regardless of how compelling the narrative sounds. This is our working framework for telling them apart.
Asset types — what we actually back
Teshy invests across four broad categories of RWA raise. Each has a distinct risk profile and a distinct set of diligence questions:
- Real estate: Commercial or residential properties tokenized via an SPV. The clearest structure, with well-established legal precedent. Key questions: who owns the SPV, what are the management fees, what is the dividend or distribution policy, and is there a defined exit mechanism (sale, refinance, or perpetual hold)?
- Private credit: Debt instruments — bridge loans, revenue-based financing, factoring — tokenized and offered to retail investors as yield-bearing tokens. Higher yields, but the underlying credit quality matters enormously and is often opaque.
- Revenue-share: A business shares a percentage of future revenue in exchange for capital raised today. Common on Republic and Wefunder. The diligence question is whether the revenue projections are grounded in actual operating history or pure forecast.
- Early-stage equity: Startup equity tokenized via a SAFE or direct equity offering. Highest risk, longest time horizon. Treat as venture-style allocation: expect most to return zero, a few to return 10x+.
The SPV structure — what you actually own
In nearly every RWA tokenization, the investor does not own the underlying asset directly. Instead, the asset is placed into a Special Purpose Vehicle — typically an LLC or limited partnership — and the investor owns a membership interest in that SPV, represented by a security token. This structure is standard and legally sensible; it isolates the asset from the issuer’s balance sheet and provides a clean ownership chain. The questions to ask are: Who are the managers of the SPV? What voting or governance rights do token holders have? What happens to the SPV if the issuing company ceases operations?
A well-structured SPV will have clearly named managers, a defined operating agreement, and a mechanism for token holders to vote on major decisions — at minimum, a sale of the underlying asset. Be cautious about SPVs where the token holder’s rights are described only in vague language like “economic participation” without specifying how distributions are calculated, when they occur, or how disputes are resolved.
Custody — who holds the underlying
The most important question in any RWA raise is also the simplest: if the issuer disappears tomorrow, what happens to my investment? The answer depends entirely on custody. For real estate, the SPV’s title to the property should be recorded with the relevant county or land registry, independent of the issuer’s operations. For financial assets — loans, credit facilities, receivables — the custodian of the underlying paper matters enormously.
The custody question to always ask
Ask the issuer directly: “If your company shut down today, what is the mechanism by which token holders access or liquidate their pro-rata share of the underlying asset?” A credible answer describes a specific legal process. A non-answer — or a pivot to discussing the company’s growth projections — is a red flag.
Transfer agents — the underappreciated piece
A transfer agent is a regulated entity responsible for maintaining the official cap table: who owns what, in what quantities, with what restrictions. In traditional securities, the transfer agent is the authoritative record. For tokenized securities, the transfer agent bridges the on-chain token ledger with the legal record. Issuers using established transfer agents — North Capital, Securitize, Vertalo, Broadridge — are operating within a regulated compliance framework. This matters for two reasons: it ensures that your ownership is legally recognized, and it creates the regulatory infrastructure necessary for secondary trading on alternative trading systems (ATS).
Raises with no named transfer agent, or with the issuer acting as their own transfer agent, are taking on additional legal and operational risk that ultimately falls on token holders if something goes wrong.
Secondary market access
One of the most overpromised aspects of RWA tokenization is liquidity. Tokens are tradeable in theory; in practice, most RWA tokens have thin or nonexistent secondary markets. The platforms that provide genuine secondary trading infrastructure for compliant security tokens — tZERO ATS, Republic, & Securitize Markets — require issuers to go through an onboarding process and maintain ongoing compliance. If a raise is listed on one of these platforms, or has a credible plan to list, that is a meaningful positive signal. If the pitch deck mentions “future secondary market liquidity” without naming a specific platform and a specific timeline, treat it as aspirational at best.
Financial transparency
Ongoing reporting quality is the best predictor of how an issuer will behave when something goes wrong. Look for quarterly investor reports that include asset-level data — occupancy rates for real estate, loan performance for credit — not just top-line summaries. Look for audited financials on any offering above a certain size. Look for a named investor relations contact who responds to questions. The absence of any of these, particularly in a raise that has been operating for more than a year, is a meaningful red flag.
Red flags that should stop the diligence process
Any one of these should give you serious pause; multiple together should end the conversation.
- ✗Asset description is vague — “a diversified portfolio of real estate assets” with no property addresses, no appraisals, no loan-to-value data
- ✗No named custodian for the underlying asset; issuer says they “hold it internally”
- ✗No transfer agent identified; issuer maintains their own cap table
- ✗Return projections that significantly exceed comparable market rates with no stated basis
- ✗No mechanism described for what happens to token holders if the issuer becomes insolvent
- ✗Investor questions in public forums go unanswered for weeks
- ✗Suspicious company expenses — founder car allowances, high travel or entertainment spend, personal expenses mixed with business operations, or unexplained overhead with little revenue to justify operating costs
- ✗Founder equity structure with sweat-equity-only co-founders retaining large stakes, or option grant pools so large they would materially dilute token holder equity on conversion or exit
How Teshy approaches diligence
Our diligence process is community-driven and on-chain where possible. For any raise we’re actively considering, we start in the Telegram group: has anyone here already researched this? What have they found? The collective memory of the community catches things that individual analysis misses. We then go to the offering documents — the Form C or Regulation A offering circular, where applicable — and read the risk factors section carefully. That section is where issuers are legally required to disclose the actual risks, and it is often more revealing than the pitch deck.
Where on-chain data is available — Realio Network transaction history, Securitize token distribution records, tZERO trading volume — we look at it. On-chain data does not lie about holder concentration, trading activity, or token velocity. A token that has been issued but shows zero secondary trading activity for twelve months tells you something that the issuer’s marketing materials will not.
Disclosure: This article describes Teshy’s internal research process and does not constitute investment advice, financial advice, or a recommendation to purchase any specific security or token. All investments carry risk, including the risk of total loss of principal. Teshy community members share information and analysis for educational purposes. Always conduct your own diligence and consult a qualified financial advisor before investing. Past performance of any asset discussed here is not indicative of future results.