CONFIDENTIAL · OBB INTERNAL

Brandon Schwab — Investor Due-Diligence Dossier

Boutique Senior Living Fund / Shepherd Premier Senior Living / Shepherd Capital LLC

Prepared: 2026-05-25 For: OBB partner (Kevin) — investment go/no-go decision Research budget: ~45 min, web sources only

Top-Line Verdict Material Red Flags

Identity: confirmed. Brandon Schwab (Crystal Lake, IL) is the founder/CEO of Shepherd Premier Senior Living (the operating company) and General Partner of the Boutique Senior Living Fund (real-estate-debt fund). He is NOT the founder of RAL Academy — that is a separate organization (Gene Guarino & family). He is a frequent guest on real estate investor podcasts.

What the research surfaced: at least five known federal lawsuits against Schwab/Shepherd entities (2023–2025), two default judgments already entered against his entities, a pending federal securities-fraud complaint alleging unregistered securities, falsified financials, falsified occupancy, operating without licenses, and concealment of prior lawsuits. A 2010 personal Chapter 7 bankruptcy. Wage/payroll problems at IL facilities in May 2025 with employees filing with the Illinois DOL. BBB C+ rating with unanswered complaint. No Form D on file with SEC for “Boutique Senior Living Fund” despite it being publicly marketed as a Reg D 506(c) offering — this alone is a serious securities-law concern.

Honest read for OBB partner: the documented record describes a small-operator senior-living entrepreneur in the middle of multiple investor-fraud allegations and chronic litigation/operational distress. None of these are convictions or final adjudications — but the pattern (recidivism of similar complaints across multiple investors, default judgments where defendants did not even appear, no SEC filings where required) is the textbook profile diligence is supposed to catch. Do not invest without (a) personally reading every federal complaint listed below, (b) demanding written, lawyer-reviewed answers to the question list in §10, and (c) requiring fully audited fund financials.

How to read this document

DOCdocumented in a primary or reputable secondary source INFreasonable inference from documented facts ANECanecdotal / forum / user-generated GAPnot found in research scope

1. Identity Verification & Background

Name	Brandon Schwab (with spouse Kelli Schwab named as co-defendant in multiple filings)
Base	Crystal Lake, IL (McHenry County); business address historically 7716 Crystal Springs Rd, Crystal Lake, IL 60012 and 1307 N Green St, McHenry, IL 60050.
Primary entity	Shepherd Premier Senior Living (operating brand, founded May 28, 2014) DOC
Holding/legal entities	Shepherd Capital LLC; Shepherd Capital LLC Huntley; Shepherd Capital LLC Huntley 2; Shepherd Capital LLC Crystal Lake; Shepherd Capital LLC Ringwood; Shepherd Capital LLC Harvard; Shepherd Capital Bull Valley; Shepherd Capital WI LLC; Boutique Senior Living Academy LLC; Boutique Senior Living Fund. DOC (per federal court captions & SEC EDGAR)
Public LinkedIn	linkedin.com/in/brandonschwab (title: Shepherd Premier Senior Living)
Origin story (per public PR & podcast appearances)	Says he became disillusioned after his grandfather’s experience in a large 100+ bed facility, discovered a 5-resident model in Florida in 2014, founded Shepherd Premier the same year. DOC (consistent across multiple podcast and trade-press appearances).
Other Brandon Schwabs in real estate?	One unrelated “Brandon Joseph Schwab” appears in the SEC IAPD adviser database (CRD #5026576). Different person; not connected to Shepherd Premier. DOC
Pre-2014 professional history	GAP — no public CV / no employer history surfaced. Schwab does not publicize a pre-Shepherd career.

2. The Business Model (Residential Assisted Living, generally)

“Boutique senior living” / RAL = converting single-family homes (typically 5,000–10,000 sq ft) into licensed assisted-living or memory-care facilities with 6–16 residents, marketed as a higher-touch alternative to 100+ bed institutional facilities. Operationally:

Licensing: state-by-state assisted living license required (Illinois Dept. of Public Health, Wisconsin DHS, etc.). License attaches to the operator AND the physical address.
Staffing: 24/7 CNA coverage; state-mandated staff-to-resident ratios; medication management protocols.
Revenue/resident: $4,000–$8,000/month private-pay per resident (memory care typically higher).
Operating costs: ~$15K–$25K/month per home is typical industry consensus (per Assisted Living Investing trade source).
Net cash flow (industry consensus): $5K–$15K/month per stabilized home.
Exit: refinance to long-term debt, sale to a regional senior-living operator, or roll-up into a fund.

Sources: Assisted Living Investing, RAL Academy public materials, Senior Housing News. Note these are the operator-side advertised numbers; actual results vary widely with occupancy, labor cost, and Medicaid mix.

3. Schwab’s Specific Operating Footprint

Reported portfolio (per Shepherd Premier website, May 2026)	Active locations in Crystal Lake IL, Harvard IL, Oregon IL, Dixon IL, Sterling IL, Monticello IL, Charleston IL; and Elkhorn WI, Cottage Grove WI, Plymouth WI. Self-described as “8 locations and growing” on LinkedIn. DOC
Per fund marketing (Yahoo Finance / BSLF site)	~$30M portfolio; $20M raised; targeting 300 homes in 5 years and 3,000 in 10 years (latter is aspirational marketing). DOC
Crystal Lake home	Opened 2020, ~4,850 sq ft, 12 residents; private & semi-private rooms. DOC
Parent structure	Each home is typically held in its own LLC (e.g., “Shepherd Capital LLC Huntley”). Boutique Senior Living Fund is structured as a Reg D 506(c) real-estate debt fund that lends to the operating LLCs. DOC
Active IL state license example	Shepherd Premier Senior Living — Crystal Lake is listed in the Illinois Dept. of Public Health licensee database. DOC (Note: web fetch certificate error blocked direct scrape of survey deficiency record; Kevin or counsel should pull this directly before investing.)

4. Coaching / Education Business

Two related-but-separate things must not be confused:

RAL Academy / Residential Assisted Living Academy: founded by the Guarino family (Gene Guarino), NOT Schwab. ~$1,497 online course / ~$2,997 live event. Mixed Trustpilot/BBB record; BBB shows the operator processed at least one refund after complaint. DOC
Boutique Senior Living Academy LLC: this IS a Schwab entity — named as a defendant in Bilello v. Schwab (1:23-cv-02139). No public reviews or pricing materials surfaced in this research scope. GAP — need to ask Schwab directly: does he sell a coaching product? At what price? How many students?

5. Investment Vehicles Offered

Boutique Senior Living Fund (BSLF)	Marketed as Reg D 506(c) real-estate debt fund lending to senior-living homes in the Midwest. Marketing materials advertise 15.2% target IRR (older), 18–22% IRR / ~2x equity multiple / 6–10 yr hold (newer), 8–10% cash-on-cash. $25M raise (Fund I), with plans for 3x $25M funds = $75M. DOC
SEC EDGAR Form D status	NO Form D was found on SEC EDGAR for “Boutique Senior Living Fund” or any “Boutique Senior Living” entity, and none for “Brandon Schwab” personally. The only Schwab-related Form D on EDGAR is Shepherd Capital Huntley 2 LLC (CIK 0001774683) filed 2019-04-23: $2.5M raised, $50K minimum, 3 investors (1 non-accredited — meaning not filed under 506(c); claimed under Rule 506(b) per item code 06b), industry “Other Health Care.” DOC — verified directly against the EDGAR XML. This is a tier-1 concern: a Reg D 506(c) offering legally requires a Form D filing within 15 days of first sale. The marketing claims 506(c) but the SEC has no record.
Direct promissory notes	Open Range complaint alleges Schwab offered $400K + $300K promissory notes at 10% with personal guarantees, structured outside any registered offering. DOC (allegation, complaint filed Nov 2025)
JV equity	Open Range complaint also alleges Schwab offered “10% equity in both projects” alongside the notes. DOC (allegation)
Public PPM / subscription docs	Per Open Range complaint, Schwab provided no PPM, subscription agreement, risk disclosure, or financial disclosures to the investor — another allegation, but consistent with the no-Form-D EDGAR record. DOC (allegation)
Sponsor co-invest / fee waterfall	GAP — not disclosed publicly. Must be obtained from the actual PPM.

6. Track Record & References

Documented exits: none surfaced in research scope. GAP
Published returns: only forward-looking marketing copy; no audited historical fund performance found. GAP
Trade-press features: McKnight’s Senior Living, Senior Housing News, Yahoo Finance press release. These are operator-supplied PR placements, not independent audits. DOC
Podcast appearances (verified): Best Ever CRE (JF3726), Straight Up Chicago Investor (Ep 142), HERO Capital Raising Show (Ep 398), Modern Investing Podcast, Life Bridge Capital (WS1348), Action and Ambition (Entrepreneur.com), REI Diamonds, Remote Real Estate Investor. DOC
BBB profile (Shepherd Premier, Crystal Lake IL): Rating C+, not BBB-accredited; 1 complaint filed which the business failed to respond to (the failure itself is cited as the reason for the C+); customer review on profile alleges owner “owes thousands of dollars, is in foreclosure and can’t answer a phone call.” BBB file opened 2023-03-17. DOC
BiggerPockets forum thread: Schwab posted an intro 2025-09-25; 4 replies but the body was not visible to anonymous fetch. ANEC

7. Red Flags / Yellow Flags / Negative Signals

REDPending federal securities-fraud lawsuit (Nov 2025)

Open Range Capital Fund 1 LLC v. Brandon Schwab, Shepherd Capital LLC, Shepherd Capital WI LLC — N.D. Ill., Case No. 1:25-cv-13898, filed 2025-11-12. 17 counts including securities fraud, breach of contract, consumer fraud, negligent misrepresentation, and breach of personal guarantees. $700K total ($400K Cottage Grove, $300K Elkhorn). Specific allegations:

Misrepresented that properties were owned (had only purchase options).
Misrepresented occupancy: claimed 13.5 residents at Cottage Grove vs. actual 6; claimed 18 at Elkhorn vs. actual 5.
Operated without valid licenses at both Wisconsin properties.
Never registered as broker-dealers; securities never registered with SEC or Illinois.
Did not provide a PPM or subscription docs.
Stopped making quarterly interest payments in Q4 2024 and Q2 2025.
Concealed numerous prior lawsuits — Schwab told this investor in an April 9, 2025 email that the action would be his “first-ever” lawsuit, even though four prior federal cases and 27+ McHenry County cases existed.

Sources: McKnight’s Senior Living & InvestmentNews coverage of the Nov 2025 complaint. Independent docket confirmation via CourtListener.

REDTwo prior default judgments already entered against Schwab/Shepherd entities

Case	Court	Outcome
Bilello v. Schwab (`1:23-cv-02139`)	N.D. Ill.	Securities/commodities case. Default judgment entered 2024-05-22 against Brandon Schwab, Kelli Schwab, and Shepherd Capital LLC. Defendants include Boutique Senior Living Academy LLC, Steve & Theresa Maskrey, Shepherd Capital Bull Valley, Shepherd Capital LLC Huntley, Shepherd Capital LLC Huntley 2. (Theresa Maskrey is also the “Partner / primary contact” listed on the Shepherd Premier BBB profile — same person.) DOC
Martin v. Shepherd Capital LLC (`3:24-cv-50302`)	N.D. Ill.	Default judgment entered 2025-08-29 against Shepherd Capital LLC d/b/a Shepherd Premier Senior Living, Shepherd Capital LLC Harvard, and Shepherd Capital LLC Bull Valley, in the total amount of $156,582.97. Civil case terminated. DOC

REDOther pending federal cases

Igney v. Schwab (1:23-cv-16642, N.D. Ill., filed 2023-12-11) — securities/commodities; plaintiffs Sandra & Bradley Igney; defendants include Brandon & Kelli Schwab and four Shepherd Capital LLCs. DOC
Momapes LLC v. Shepherd Capital LLC Harvard (1:24-cv-07951, N.D. Ill., filed 2024-08-30) — default judgment also entered (Document #5). DOC
AdCap Growth Partners Fund LP v. Schwab (1:25-cv-04072, S.D.N.Y., filed 2025-05-14) — complaint filed by an institutional fund against Brandon Schwab. Nature of suit not yet visible in research scope (court behind Cloudflare); summons issued. DOC (existence), GAP (specifics)

REDPersonal Chapter 7 bankruptcy (2010)

Brandon Schwab and Kelli Schwab filed a joint Chapter 7 voluntary petition 2010-09-10. Filed by attorney David L. Stretch. DOC (CourtListener docket #15601763). Per Open Range complaint, this was filed 2010-09-20 (small date discrepancy — the CourtListener filing date is authoritative).

REDPayroll problems / Illinois DOL complaint (May 2025)

Per WCIA (Champaign-Urbana, IL) reporting in May 2025: employees at Shepherd Premier facilities in Monticello and Charleston, IL reported their checks failed to arrive (direct deposit broke; paper checks bounced for insufficient funds). One employee unpaid 20+ days; account in the negative; filed complaint with the Illinois Department of Labor. Schwab told reporters the issue was resolved. DOC

AMBERBBB rating C+, unresponded complaint

See §6 above. The unresponded complaint and customer foreclosure allegation are independent corroboration of distress.

AMBER27+ McHenry County (IL) state-court suits

Per Open Range federal complaint, McHenry County records show at least 27 lawsuits against Schwab/defendants predating April 9, 2025. DOC (per allegation; not independently verified in this research scope). State-court system would require manual search to enumerate.

REDSEC EDGAR: no Form D for the actively-marketed 506(c) fund

This is its own item even though it’s also in §5. A Reg D 506(c) offering legally must file Form D with the SEC within 15 days of first sale, and most states require a notice filing as well. Schwab’s marketing site advertises BSLF as 506(c). EDGAR’s full-text search returns ZERO hits for “Brandon Schwab,” “Boutique Senior Living,” or “Shepherd Premier.” The only filing under any related name is the 2019 Shepherd Capital Huntley 2 Form D, which was 506(b), $2.5M, 3 investors. DOC — verified via direct EDGAR API query.

UNKNOWNState survey deficiencies

The Illinois Dept. of Public Health licensee record for Crystal Lake exists but direct fetch failed in this research scope (TLS cert error on the IDPH dph.illinois.gov subdomain). Wisconsin DHS records were not enumerable in this scope. Kevin / counsel should request the most recent survey reports for all 10 reported homes directly from IDPH and WDHS before investing.

8. Sector Context — Macro Read

Honest framing of the tide Schwab is operating in:

Tailwind: demographic — the 75+ population in the U.S. is the fastest-growing age cohort through 2035.
Headwind — bankruptcies climbing: Senior living bankruptcies rose from 11 in 2024 to a projected 15–16 in 2025 (McKnight’s, Senior Housing News, July–Aug 2025). Major 2025 collapses include Genesis Healthcare (175 facilities, 20,000 beds, Chapter 11 July 2025), Pacifica Senior Living (93 homes, Chapter 7 liquidation March 2025), and SpiriTrust Lutheran (80-year-old chain, Chapter 11).
Headwind — reimbursement: the “One Big Beautiful Bill Act” trims ~$1T from Medicaid, which is the primary payer for nursing-level care. Private-pay RAL is somewhat insulated but not immune.
Headwind — labor: caregiver wages are still climbing post-2022; turnover is industry-wide ~50%+ annually. This squeezes the 10–20% operating margin RAL models assume.
Headwind — insurance: liability premiums for senior care up materially in 2024–2025.

Net: the RAL model is a defensible niche but the sector is in active distress. Operating discipline matters more in 2025–2026 than it did in 2019–2021.

9. Question List for Schwab (30 seconds — Tier 1)

Where is the Form D for Boutique Senior Living Fund? If the offering is 506(c) as marketed, the filing is mandatory — show us the EDGAR accession number, or explain why no filing exists.
Walk us through every federal lawsuit filed against you or your entities in the last 4 years. Provide the docket numbers in writing. Why was a default judgment for $156,582.97 entered against Shepherd Capital, Shepherd Capital Harvard, and Shepherd Capital Bull Valley on August 29, 2025?
Why did Open Range Capital Fund 1 allege you misrepresented occupancy by 2x at two Wisconsin facilities? What is your written response?
The Open Range complaint alleges you operated Cottage Grove and Elkhorn without valid licenses. Were those licenses in place on the dates the fund advanced money? Documentary proof.
Why did you tell the Open Range investor in writing on April 9, 2025 that that case would be your “first-ever lawsuit” when at least four prior federal cases existed?
Provide the most recent state survey deficiency reports for every operating home (IDPH for Illinois, WDHS for Wisconsin).
Provide audited financial statements for the Boutique Senior Living Fund for FY 2023 and FY 2024.
What is the personal sponsor co-invest as a % of fund LP capital?
Provide the complete fee schedule: acquisition fee, asset-management fee, refinance fee, disposition fee, promote/carry waterfall, any related-party transaction fees.
Provide a list of every distribution actually paid to LPs in the past 24 months (date, amount, % of capital).
What happens if Brandon Schwab becomes incapacitated or leaves? Key-person clause? Successor manager?
Names & contacts of two current LPs we can call (your reference, plus one we pick from the cap table at random).
Personal credit report + statement of net worth (the personal guarantee is only as good as the guarantor).
Were any IL or WI employees in fact unpaid in May 2025 (the WCIA report)? How many? Were all back wages paid? Provide settlement letters with the IL DOL.
What is the loan-to-value on the underlying senior debt of each home in the fund, and what is the senior lender’s position relative to BSLF’s claim?

10. What He Probably Will NOT Volunteer

The 2010 personal Chapter 7 bankruptcy.
The full list of LLC-level defendants — the “Shepherd Capital” entity tree is large and atomized, which can obscure cross-default exposure.
Whether his spouse Kelli Schwab is jointly liable on any of the personal guarantees (she has been named as a co-defendant in Bilello and Igney).
Whether the “Theresa Maskrey” listed as Partner on the Shepherd Premier BBB profile is the same Theresa Maskrey named as a defendant in Bilello v. Schwab (almost certainly yes).
The cadence and result of fund audits, if any independent audit has been performed.
The actual occupancy at every operating home, building by building, as of last month.
The terms of any forbearance, restructuring, or workout in place with senior lenders.
Whether his entities have been the subject of any state attorney general or state securities-division inquiry (IL, WI, or otherwise).
Distribution reductions or pauses to existing LPs in 2024 or 2025.
His own salary/management fee draws as a % of fund expenses.

11. P0 Items for the OBB Partner

Do not wire any capital until Schwab produces (a) the Form D filing for BSLF or a written legal explanation of why one is not required, and (b) full counsel-reviewed answers to question list §9.
Retain securities counsel to read the Open Range complaint (1:25-cv-13898) and the Bilello, Igney, Martin, Momapes, and AdCap dockets before any capital commitment.
Order the Illinois DPH survey reports for all IL homes and Wisconsin DHS reports for all WI homes — this is free / nominal cost and is the single best independent signal on operational quality.
Run a personal credit / background check on Brandon Schwab AND Kelli Schwab (joint exposure on Bilello/Igney).
If the partner is still interested after items 1–4, demand a structured sit-down with Schwab + his attorney + Schwab’s most recent fund auditor (if any).

Source Notes

SEC EDGAR full-text query for “Brandon Schwab” / forms=D → 0 hits. Query for “Boutique Senior Living” / forms=D → 0 hits. Query for “Shepherd Capital” / forms=D → 2 hits, only one (Shepherd Capital Huntley 2 LLC, CIK 0001774683) is Schwab-related; the other (Shepherd’s Model Hedge Fund LP, NV) is unrelated. Direct verification 2026-05-25.
Shepherd Capital Huntley 2 Form D XML: sec.gov/Archives/edgar/data/1774683/000177468319000001/primary_doc.xml
McKnight’s Senior Living, “Investment fund alleges fraud in $739,000 senior living securities scheme” (Nov 2025): link
InvestmentNews, “Investment fund alleges $700K fraud in unregistered senior living securities”: link
WCIA, “Employees of Central IL memory care facility say company is missing payments; founder responds”: link
Better Business Bureau profile, Shepherd Premier Senior Living (Crystal Lake IL): link (C+ rating, opened 2023-03-17, 1 unresponded complaint).
CourtListener docket search, “Brandon Schwab” OR “Shepherd Capital” (22 docketed cases, 116 entries; key dockets: Bilello 1:23-cv-02139, Igney 1:23-cv-16642, Martin 3:24-cv-50302, Momapes 1:24-cv-07951, Open Range 1:25-cv-13898, AdCap 1:25-cv-04072 (S.D.N.Y.), 2010 Ch.7 bankruptcy docket 15601763).
Boutique Senior Living Fund marketing site: link (returns & structure; site was 503 on direct fetch at research time; structure data came from Yahoo Finance press release and McKnight’s).
Shepherd Premier Senior Living, locations page: link
The Org / Crunchbase / RocketReach profiles cross-confirmed identity.
Senior Housing News, “Inside the Financial, Human Impact of Senior Living’s Bankruptcy Trend” (Jul 17 2025): link
McKnight’s, “Senior living and care bankruptcies climb”: link
RAL Academy & sector return data: residentialassistedlivingacademy.com; assistedlivinginvesting.net.

This dossier was assembled from publicly accessible web sources in ~45 minutes of research. It is not a legal opinion, not investment advice, and not a substitute for engaging securities counsel, an independent auditor, and state-licensing-bureau record requests before any capital commitment. Several primary sources (Justia, PACER, IDPH, BSLF, AdCap docket) were inaccessible to anonymous web fetch in this research scope and should be re-pulled directly by counsel. Allegations in active litigation are not findings of fact.