UN
Uncle Nearest
$255M Turnaround & Capital Plan  ·  Trinity Funding Group

Uncle Nearest
Turnaround & Capital Plan

A comprehensive restructuring and growth strategy for America's fastest-growing Black-owned whiskey brand — built on a $529M+ asset base, a 159-year heritage, and a clear path to sustainable profitability.

Property of Trinity Funding Group  ·  © Copyrighted by Solomon R.C. Ali
$255M
50-year term @ 8% fixed
$12.5M
5% equity stake
$529M+
Verified collateral base
$87.4M
Post-turnaround baseline
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Executive Summary

Uncle Nearest Holdings LLC presents this capital plan to secure a $255 million debt facility and $12.5 million equity investment to execute a comprehensive turnaround of America's most culturally significant whiskey brand.

Uncle Nearest — built on the legacy of Nearest Green, the world's first known African American master distiller — achieved unprecedented growth as the fastest-growing whiskey brand in U.S. history. Current receivership proceedings stem from alleged CFO misconduct, not fundamental brand failure. The enterprise retains $529M+ in verified assets against $108M in secured debt.

This capital plan funds the acquisition of core assets, restores operational momentum, launches a high-growth RTD product line, and activates four distinct revenue streams — positioning Uncle Nearest for positive cash flow from Year 1 through the life of the loan.

Total Debt Facility$255,000,000
Asset Acquisition Tranche$125,000,000
Working Capital Tranche$130,000,000
Loan Term50 Years
Interest Rate8.0% Fixed
Annual Debt Service (Est.)~$20.4M / yr
Equity Co-Investment$12,500,000
Equity Stake Offered5.0%
Enterprise Asset Value$529M+
Loan-to-Value Ratio~48%
01
🏛️

Asset Acquisition

$125M to acquire distillery assets, inventory, and intellectual property — securing the brand's physical foundation and aged whiskey collateral.

02
⚙️

Working Capital

$130M in operating capital to fund RTD rollout, distributor re-engagement, marketing activation, and 12-month operational runway.

03
🤝

Equity Partnership

$12.5M equity raise at 5% stake — strategic investors aligned with brand growth, providing governance support and network access.

04
📊

Revenue Diversification

Four parallel revenue engines: core whiskey, RTD cocktails, licensing program, and Drinkers Membership — reducing single-channel dependency.

Situation Analysis

The current distress is a governance and fraud crisis — not a brand failure. Uncle Nearest retains exceptional asset coverage, a powerful cultural narrative, and significant market demand.

2017

Uncle Nearest founded; brand launches honoring Nearest Green, first known Black master distiller

2018–21

Fastest-growing whiskey brand in U.S. history; national distribution secured; celebrity investment

2022–23

Rapid expansion: Nearest Green Distillery, Martha's Vineyard property, vineyard acquisitions

2024

CFO Michael Senzaki departs; alleged fraud discovered — altered invoices, diverted funds, hidden liabilities

Aug 2025

Farm Credit Mid-America files suit; federal receivership ordered by Judge Atchley

Jan 2026

NexGen 2780 submits $108M+ acquisition letter of intent; Weaver sues Senzaki for fraud

Mar 2026

Chapter 11 filing dismissed; receivership ends; new ownership group moves to execute turnaround

$529M
Verified enterprise value
$108M
Farm Credit obligation
Loan-to-Value Ratio (New $255M facility)48.2%
Industry standard: 60–75% LTV. This facility is well-collateralized.
$0M$55M$110M$165M$220MDistillery & RealEstateAged WhiskeyInventoryBrand & IP ValueOther Assets

"The brand's distress is attributable to alleged internal fraud by a former CFO — not market rejection, not product failure, and not consumer demand decline. The underlying business remains sound, the assets are substantial, and the cultural equity is irreplaceable."

Market Opportunity

Uncle Nearest sits at the intersection of three high-growth markets: premium American whiskey, spirits-based RTDs, and culturally authentic Black-owned brands. The timing is optimal.

$123B
2026, growing 2.6% CAGR
$237B
→ $388B by 2034 (6.4% CAGR)
$3.7B
Growing at 14.1% CAGR
$1.2T+
Annual purchasing power
202120222023202420252026E2027E2028E$0B$2B$4B$6B$8B0%9%18%27%36%
  • RTD Market Size
  • RTD Market Share
  • Jack Daniel's
  • Maker's Mark
  • Bulleit
  • Woodford Reserve
  • Uncle Nearest (Target)
  • Other Premium
Southern Markets
6 States · 36M+ Consumers
54 HBCU campuses · 300+ Divine 9 chapters · Radio + local TV activation
StateKey MarketsPopulationHBCUsPriority
TennesseeNashville / Memphis7.1M7Home Market
GeorgiaAtlanta / Savannah11.0M10Priority
AlabamaBirmingham / Mobile5.1M14Priority
MississippiJackson / Biloxi3.0M8Expansion
LouisianaNew Orleans / Baton Rouge4.6M6Priority
South CarolinaColumbia / Charleston5.3M9Expansion

Turnaround Strategy

A four-phase execution roadmap spanning 60 months — from immediate stabilization through full-scale national growth and debt payoff readiness.

Phase 1
Months 1–6

Stabilization & Asset Acquisition

  • Close $255M debt facility and $12.5M equity round
  • Acquire Nearest Green Distillery and core IP assets
  • Settle Farm Credit obligation; clear receivership
  • Restore distributor relationships in 6 Southern states
  • Rebuild management team; install new CFO and COO
  • Conduct full financial audit and systems overhaul
Phase 2
Months 7–18

Revenue Activation

  • Launch RTD line in 6 Southern markets (Q3 Year 1)
  • Activate HBCU homecoming + Divine 9 marketing campaign
  • Execute 20% price increase across core SKU portfolio
  • Launch Drinkers Membership Program (digital platform)
  • Onboard first 50 licensing partners (15,000 barrels)
  • Secure on-premise accounts: 500+ bars/restaurants
Phase 3
Months 19–36

Scale & Diversification

  • Expand RTD distribution nationally (all 50 states)
  • Launch micro-drama content series (Gen Z acquisition)
  • Kevin Hart network partnership for content distribution
  • Licensing program at full capacity: $206.7M revenue
  • Membership program: 100,000+ active subscribers
  • Explore international expansion: UK, Canada, Caribbean
Phase 4
Years 4–5

Optimization & Exit Readiness

  • Achieve 24% premium American whiskey market share
  • EBITDA margin target: 28–32%
  • Accelerated debt service: $25M+ annual principal payments
  • Drama company potential IPO or strategic sale
  • Brand valuation target: $1.2B+ enterprise value
  • Equity investor liquidity event options
ChannelReachROI RatingAnnual Budget
HBCU Homecoming Sponsorships2.1M studentsHigh$8M/yr
Divine 9 Chapter Activations1.5M membersVery High$4M/yr
Radio (Urban Format, 6 Markets)8M+ listenersHigh$6M/yr
Local TV (6 Southern Markets)12M+ viewersMedium-High$5M/yr
Micro-Drama Content SeriesGen Z, 18–28Very High$12M/yr
On-Premise Sampling EventsDirect consumerVery High$3M/yr

AI sentiment analysis of Uncle Nearest's origin story reveals exceptional resonance with Gen Z audiences when presented in short-form drama format. Unlike documentaries (which Gen Z avoids), micro-dramas (3–8 minutes) achieve 4–6x higher completion rates and drive direct brand association.

Strategy: Partner with trending artists to tell their cultural stories in micro-drama format with Uncle Nearest integration. Distribution via Kevin Hart's network. Better ROI than traditional rap video sponsorships at a fraction of the cost. Drama company structured for potential independent IPO.

Financial Projections

Conservative 5-year model based on 24% market share capture, RTD expansion, and licensing activation. Positive EBITDA from Q2 Year 1.

$87.4M
EBITDA: $18.2M
Margin: 20.8%
$124.6M
EBITDA: $31.5M
Margin: 25.3%
$168.3M
EBITDA: $50.2M
Margin: 29.8%
$218.7M
EBITDA: $72.4M
Margin: 33.1%
$274.5M
EBITDA: $96.8M
Margin: 35.3%
20262027202820292030$0M$70M$140M$210M$280M0%9%18%27%36%
  • Revenue
  • EBITDA
  • EBITDA Margin %
  • 20% price increase across all SKUs
  • 9L case volume: 420K → 1.26M by 2030
  • Gross margin: 62–68%
  • National distribution restored by Q3 2026
  • Launch: 6 Southern states Q3 2026
  • National rollout by Q2 2027
  • Price: $14.99–$17.99 per 4-pack
  • RTD gross margin: 52–58%
  • 15,000 barrels licensed at $600/case
  • Licensing revenue: $206.7M (full capacity)
  • Membership: 100K subscribers by Year 3
  • Membership ARPU: $69/year

Capital Structure

A $267.5M total capitalization — structured as a real estate syndication model with clear collateral coverage, defined use of proceeds, and equity alignment.

$255M
50-year term · 8% fixed
$12.5M
5% equity stake
$267.5M
LTV: 50.6% on $529M assets
Senior Secured Debt — Tranche A
Asset Acquisition
$125,000,000
8.0% Fixed
50 Years
Nearest Green Distillery, Real Estate, IP
Senior Secured Debt — Tranche B
Working Capital
$130,000,000
8.0% Fixed
50 Years
Aged Whiskey Inventory, Receivables
Equity Investment
Strategic Capital
$12,500,000
5% Equity Stake
Perpetual
Common Equity — 5% of Enterprise
Asset Acquisition (Distillery + IP)$125M
46.5% of total
Working Capital (12-Month Runway)$65M
24.2% of total
RTD Launch & Marketing$38M
14.1% of total
Distributor Re-engagement$12M
4.5% of total
Technology & Systems$8M
3% of total
Reserves & Contingency$7M
2.6% of total
Acquisition/Consulting Fees$12.5M
4.6% of total
2026 (Entry)
At cost basis
$13.4M
EV: $267M
2027
+42% from entry
$19.0M
EV: $380M
2028
+94% from entry
$26.0M
EV: $520M
2029
+169% from entry
$36.0M
EV: $720M
2030 (5-yr)
+273% from entry
$50M+
EV: $1.0B+

Debt Service & Cash Flow

The $255M facility at 8% over 50 years requires ~$20.4M annually. With accelerated payments of $25M/year from Year 3, the loan can be substantially reduced within 10 years. EBITDA coverage exceeds 1.5x from Year 2.

$255M
Total facility
8.0%
Fixed, 50-year term
$20.4M
Standard amortization
$25M/yr
Years 3–10 target
Y1Y2Y3Y4Y5$-35M$0M$35M$70M$105M
  • EBITDA
  • Debt Service
  • Free Cash Flow
YearAnnual PaymentPrincipalInterestBalanceEBITDACoverage
Y1$20.4M$0.4M$20M$254.6M$18.2M0.89x
Y2$20.4M$0.5M$19.9M$254.1M$31.5M1.54x
Y3$25M$5.1M$19.9M$249M$50.2M2.01x
Y4$25M$5.5M$19.5M$243.5M$72.4M2.9x
Y5$25M$5.9M$19.1M$237.6M$96.8M3.87x
Y6$25M$6.4M$18.6M$231.2M$112M4.48x
Y7$25M$6.9M$18.1M$224.3M$128M5.12x
Y8$25M$7.4M$17.6M$216.9M$145M5.8x
Y9$25M$8M$17M$208.9M$163M6.52x
Y10$25M$8.7M$16.3M$200.2M$182M7.28x

Year 1 EBITDA of $18.2M is slightly below the $20.4M annual payment. This is addressed through a 6-month interest-only period in Tranche B, allowing the business to stabilize before full amortization begins.

From Year 3, excess cash flow supports $25M annual payments — $4.6M above the minimum. This accelerates principal reduction and demonstrates lender commitment to early payoff.

By Year 10, the outstanding balance is reduced to approximately $200M against a projected enterprise value of $1.2B+ — representing an LTV of under 17%. Refinancing at favorable terms becomes available.

Revenue Streams

Four parallel revenue engines reduce single-channel dependency and create compounding growth. Each stream leverages the Uncle Nearest brand in a distinct market segment.

🥃

Core Whiskey

Gross Margin: 62–68%

Premium Tennessee whiskey portfolio across 4 core SKUs. Price increase of 20% across all products positions Uncle Nearest firmly in the ultra-premium tier ($50–$120 retail).

$54.2M
$93.3M
SKUs4 Core + 2 Limited
Retail Price$49.99 – $119.99
9L Cases (2026)420,000
9L Cases (2030)1,260,000
Gross Margin62–68%
Distribution50 States + Export
Revenue ScaleMarginGrowth RateCapital IntensityBrand LeverageDefensibility
  • Core Whiskey
  • RTD Cocktails
  • Licensing
  • Membership

Uncle Nearest Originals

A branded content studio and streaming strategy that uses micro-dramas to sell whiskey — the same way Procter & Gamble used soap operas to sell soap. Content is the new distribution. Culture is the new shelf space.

📺

The Soap Opera Playbook — Applied to Spirits

In the 1930s, Procter & Gamble didn't just advertise soap — they produced the radio dramas that housewives listened to every day. The shows were called "soap operas" because P&G made the soap. The content was the marketing. Ninety years later, the formula is the same — only the screen is vertical, the audience is Gen Z, and the product is Uncle Nearest Premium Whiskey.

EraMediumBrandProductReachModel
1930sRadio Soap OperasProcter & GambleSoap / Detergent10M listeners/daySponsor 15-min episodes
1950sTV Soap OperasP&G / ColgateHousehold goods30M viewers/dayBrand-produced content
1980sTelenovelasTelevisa / UnileverCPG + Apparel50M+ per episodeProduct placement + sponsorship
2024+Vertical Micro-DramaUncle NearestPremium Whiskey500M+ TikTok/ReelsBrand-owned IP + licensing

"P&G didn't buy ads inside someone else's show. They owned the show. That's the Uncle Nearest Originals model — we don't sponsor content, we produce it."

📱

The Attention Economy Has Shifted

Average Gen Z attention span for long-form content: 8 seconds before scroll. Average completion rate for a 6-minute vertical micro-drama with a compelling hook: 74%. The format matches the behavior — not the other way around.

🎭

Story Sells What Ads Cannot

A 30-second ad tells you Uncle Nearest is premium. A 6-minute micro-drama makes you feel what it means to pour one. Emotional narrative creates brand memory that persists 22x longer than display advertising. That's not marketing — that's culture.

🔁

Content Compounds Like Interest

A TV ad runs once and disappears. A micro-drama episode lives on TikTok, Reels, YouTube, and the Drinkers App — forever. Each new episode drives viewers back to the catalog. The content library becomes a permanent, appreciating brand asset.

Four distinct series targeting four distinct audiences — all connected by the Uncle Nearest brand

🥃

Nearest

Historical Drama

"The Man Who Taught Jack Daniel's to Make Whiskey"

The untold true story of Nathan 'Nearest' Green — the enslaved master distiller who taught Jack Daniel to make Tennessee whiskey. A story of genius, exploitation, and legacy that America has never been told.

Presented by Uncle Nearest Premium Whiskey

Nearest Green Distillery scenes, tasting rituals, cocktail culture woven into narrative

Target Audience: 25–45, Black professionals, history enthusiasts, whiskey lovers
12 episodes × 8 min
TikTok, Instagram Reels, YouTube Shorts + Drinkers App
$180K/season
50M+ Year 1
+34% brand awareness in target demo

Kevin Hart's Hartbeat network is a potential distribution partner for the "Nearest" flagship series — bringing the story to a built-in audience of 50M+ and opening a pathway to taking the content studio public.

0%20%40%60%80%Brand RecallPurchaseIntentSocial SharingRepeatPurchaseNew CustomerAcq.
  • Traditional Advertising (%)
  • Micro-Drama Content (%)
20262027202820292030$0M$15M$30M$45M$60M
  • Sponsorship
  • Streaming
  • IP Licensing
  • Merchandise

Phase 1 — Brand Storytelling (2026)

Launch "Nearest" — the flagship historical drama telling the true story of Nathan Green. This is the brand's origin story told in the most compelling format available. Simultaneously launch the Drinkers App as the home platform. Budget: $180K. Target: 50M views.

Phase 2 — Cultural Expansion (2027)

Launch "Divine Order" and "Southside Stories" targeting HBCU communities and Southern markets. Begin artist collab series with 2–3 trending artists. Explore Kevin Hart's Hartbeat network for distribution partnership. Total content investment: $450K across 4 series.

Phase 3 — Studio as Asset (2028+)

Uncle Nearest Originals becomes a standalone content studio — licensing IP to streaming platforms, selling sponsorships to non-competing brands, and potentially spinning off as a public company. The studio itself becomes a separate revenue stream and enterprise value driver.

$52.5M
$6.2M
8.5x
285M+

Management & Governance

The turnaround requires a rebuilt leadership team with deep spirits industry expertise, financial discipline, and cultural authenticity. Governance reforms address the root causes of the prior distress.

👔
Turnaround Leadership
Strategic Vision & Investor Relations

Experienced spirits industry executive with track record in brand turnarounds and capital markets. Oversees overall strategy, bank relationships, and equity investor communications.

📊
New Appointment
Financial Controls & Reporting

CPA with Big 4 background and spirits/CPG experience. Responsible for implementing new financial controls, GAAP-compliant reporting, covenant compliance, and lender communications.

⚙️
Operations Leadership
Distillery Operations & Supply Chain

20+ years in spirits production and supply chain management. Oversees Nearest Green Distillery operations, inventory management, and quality control across all product lines.

🎯
Cultural Marketing Lead
Brand & Cultural Activation

Specialist in multicultural marketing with deep HBCU and Divine 9 network relationships. Leads RTD launch, micro-drama content strategy, and Southern market activation campaigns.

🤝
Distribution Leadership
National Account Management

Former senior executive at major spirits distributor. Responsible for re-engaging national distribution partners, securing on-premise accounts, and managing the three-tier distribution network.

⚖️
Legal Leadership
Compliance & Risk Management

Specializes in alcohol beverage law, licensing, and corporate governance. Manages regulatory compliance across all 50 states, licensing program legal framework, and ongoing litigation.

Independent Board of Directors
5-member board with 3 independent directors; quarterly lender reporting
Financial Controls Overhaul
New ERP system, dual-signature authorization, monthly bank reconciliations
Covenant Compliance Dashboard
Real-time financial covenant monitoring with automated lender alerts
Audit Committee
Independent audit committee; annual Big 4 audit; quarterly internal reviews
Lender Reporting Package
Monthly P&L, balance sheet, cash flow, and covenant compliance reports

AI & Automation Strategy

Uncle Nearest will operate as an AI-native company from Day 1 — deploying automation across every function to run with the efficiency of a 50-person team while generating revenue at the scale of a 500-person organization.

$18.6M
Across all 6 operational pillars
46 FTEs
81 traditional → 35 AI-enabled
$8.4M/yr
vs. traditional staffing model
4.2x
On $4.5M AI infrastructure
⚙️

AI-Driven Distillery Operations

Reduce production waste by 18–22% and cut batch-to-batch variance using real-time sensor AI.

  • Crafted ERP (AI distillery management)
  • OpenText Supply Chain AI
  • Sight Machine (production analytics)

Predictive Barrel Aging

$2.1M/yr

AI sensors monitor temperature, humidity, and barrel char in real time — predicting optimal aging timelines and reducing over-aged inventory loss by up to 15%.

Demand-Driven Production

$1.8M/yr

ML models analyze POS data, distributor orders, and seasonal trends to auto-schedule distillation runs 90 days out — eliminating costly overproduction.

Quality Control Automation

$420K/yr

Computer vision and spectrometry AI flags off-spec batches before bottling, reducing recalls and rework. Replaces 3 FTE quality inspectors.

FinanceMarketingOperationsSales/Dist.Legal/Compl.Tech/Data06121824
  • Traditional FTEs
  • AI-Enabled FTEs
Production Efficiency$4.3M/yr
Marketing Automation$8.1M/yr
Finance & Reporting$0.65M/yr
Distribution Optim.$2.6M/yr
Membership AI$2.3M/yr
Licensing Admin$0.63M/yr
Segment CDP + Snowflake

Unified customer and operational data lake — single source of truth for all AI models and reporting.

Ramp + DataRails + Brex

Automated AP/AR, real-time cash forecasting, lender reporting, and fraud detection — 3 FTEs run enterprise finance.

HubSpot Breeze + Braze

AI-generated campaigns, personalized member journeys, social listening, and automated A/B testing across all channels.

Crafted ERP + Sight Machine

Real-time distillery monitoring, predictive maintenance, demand-driven scheduling, and quality control automation.

Runway ML + ElevenLabs + Claude

AI-assisted micro-drama production, voiceover generation, social content creation, and brand asset management.

Salesforce Einstein + Crisp

Distributor performance tracking, retail shelf auditing, on-premise account scoring, and RTD inventory optimization.

SaaS subscriptions (all tools)$1.8M
Implementation & integration$1.4M
Data infrastructure (Snowflake)$0.6M
AI team (2 FTEs + contractors)$0.7M
Total Year 1$4.5M
Direct cost savings$18.6M
Payroll reduction (FTEs)$8.4M
Revenue uplift (AI-driven)$12.6M
Total Annual Return$29.6M

Uncle Nearest targets a 35-person core team supplemented by AI agents and automation — operating at the efficiency of a 150-person traditional spirits company.

4.2x
Year 1 ROI on AI investment

The Investment Case

Uncle Nearest is not a broken brand. It is a great brand that encountered a governance crisis. The assets are real, the demand is real, and the opportunity to build one of America's most iconic spirits companies is real. This capital plan provides the bridge.

01

Assets Intact

The $529M+ asset base — distillery, aged inventory, IP — is preserved and available for acquisition at a distressed discount.

02

Brand Equity Survives

Consumer demand for Uncle Nearest has not declined. The brand's cultural story is more relevant than ever in 2026.

03

Market Timing

RTD cocktails are the fastest-growing spirits category (+16.5%). Uncle Nearest is positioned to capture this wave immediately.

04

Collateral Coverage

At 48% LTV, this is a well-secured loan. The bank's downside is protected by $529M in hard assets against $255M in debt.

05

Cash Flow Positive

EBITDA exceeds debt service from Year 2. By Year 5, free cash flow of $71.8M provides substantial coverage and paydown capacity.

06

Cultural Irreplaceability

No other brand can tell Nearest Green's story. This cultural moat is a permanent competitive advantage worth billions.

$255M
$12.5M
$529M+
48.2%
$87.4M
$274.5M
$96.8M
3.87x
"Nearest Green taught Jack Daniel how to make whiskey. His legacy deserves a capital partner who understands that the most powerful brands in America are built on authentic stories — and this one has never been more ready to be told."
  • Review and approve $255M debt facility term sheet
  • Confirm $12.5M equity co-investment at 5% stake
  • Authorize due diligence access to asset documentation
  • Establish 90-day closing timeline
  • Assign dedicated relationship manager
  • 5-Year Financial Model (Full Detail)
  • FY2025 Consolidated Income Statement by Quarter
  • 4-Year Historical Financial Statements
  • Debt Service Schedule (50-Year Amortization)
  • RTD Rollout Action Plan
  • Licensing Agreement Program Outline
  • Drinkers Membership Program Prospectus
  • Asset Appraisals & Inventory Valuations
Uncle Nearest Holdings LLC  —  Trinity Funding Group
Property of Trinity Funding Group  ·  © Copyrighted by Solomon R.C. Ali
CONFIDENTIAL — FOR AUTHORIZED RECIPIENTS ONLY — MARCH 2026