Main Street Holding Co.

Main Street
Holding Company

A lifecycle capital partner to lower-middle-market SMB operators.

The Opportunity

$10T of businesses changing hands

70% of owners have no transition plan

The Problem

Financing Is the Problem

To buy a Main Street business, a first-time owner has almost no real financing options. One program was built for it, and the whole market leans on it.

Cash, self-funded

Almost no first-time buyer has $2M to $10M sitting in the bank.

Rarely Possible

Conventional bank loan

Banks won't back a first-time owner with no track record and little collateral.

Banks Pass

Private equity

Sub-$10M Main Street deals are too small to be worth their time.

Too Small for PE

Seller financing

Useful at the edges, but no seller funds the whole purchase.

Partial at Best

SBA 7(a)

Built for exactly this buyer. It's the rail almost every Main Street deal runs on, and it still leaves gaps.

Only Consistent Option
The Financing Gaps

But Even the SBA Program has Gaps

Real hurdles exist for both new buyers and existing owners who want to leverage SBA debt.

First Time Business Buyer
The Capital Gap.

SBA 7(a) requires a real, sourced 10% injection on top of all the deal costs and post-close liquidity. Qualified buyers lose great deals over the inability to fund the transaction.

The Underwriting Gap.

Outside capital can't get conviction on a minority stake in a first-time buyer's single small deal. No history, no control, so the capital that could help won't.

Owner Looking to Scale With SBA Debt
The Personal Guarantee Is Grueling.

Even when the business is healthy, the PG is a real risk: default means losing everything personally.

SBA Restricts the Speed of Growth.

Cheap debt, but too restrictive to bring on partners or get creative on expansion opportunities.

The Solution

One Fund to Address the Gaps

One $40M fund deploying two strategies: $12M sourced and deployed at acquisition, $28M compounding with proven operators.

Strategy
Invest alongside new buyers at the time of acquisition to help alleviate the equity and underwriting gaps.
Provide creative capital to extinguish the personal guarantee, fuel future growth, or provide secondary liquidity.
ALLOCATION
$12M
$28M
CHECK SIZE
$0.1M – $0.5M
$1.0M – $5.0M
ENTRY VALUATION
$2.0M – $10M
$5M – $25M
TARGET OWNERSHIP
<20%
19 – 49% cumulative
# of Investments
30 – 40
12 – 15
SOURCE
Contrarian Academy
Growth Boardroom
Market Sizing

A Massive Market Opportunity

SBA 7(a) is a $37B market at an all-time high, and the equity gap we fill scales with it.

FY25 LOAN VOLUME
$37.0B
All-time record. FY21 nearly matched at $36.5B.
FY25 LOANS APPROVED
77,600
~7× since the early '90s. The equity gap we fill scales with the program.
SBA 7(A) LOAN APPROVAL VOLUME · FY1992-FY2025
$40B $30B $20B $10B $0 FY25 · $37.0B '92 '00 '09 '18 '25
Source: U.S. Small Business Administration, 7(a) loan approval volume, FY1992–FY2025.
Our Products

Two Proprietary Products. One Unfair Advantage

We teach, support, and scale entrepreneurs, from their first acquisition to their fifth and beyond. Creating structural proprietary deal flow.

Aspiring owners, looking for expert guidance on how to successfully buy a business.

  • Cohort education on acquisition & SBA 7(a) mechanics
  • In-house Quality-of-Earnings on prospective targets
  • SBA 7(a) loan-brokerage support
  • End-to-end software: offer, LOI, diligence, close
  • Multiple weekly calls, including live deal reviews and special-topics calls
  • Continuous LOI and deal review from experts
  • Access to all Deal Advisors
  • Ongoing events + a community of buyers

Entrepreneurs looking to rapidly scale their business and unlock the next level of growth.

  • 1:1 live support with an advisor who deeply understands your business
  • Frequent advisor touch-points to constantly discuss progress and pain points
  • Systematic financial reviews
  • Value-creation playbooks built for the business
  • Deal-structuring for add-ons, recaps, refinances
  • Growth-marketing leadership + operator support
  • Hands-on architecture of the next stage of growth
  • Ongoing events + a community of owners
Our Unfair Advantage

We Don't Source Deals. We Manufacture Them

Funded operators don't leave: the Acquisition engine feeds them straight into the Expansion engine, where we begin to evaluate them for a much larger investment.

13M FOLLOWERS 130M MONTHLY VIEWS Top 10 BUSINESS PODCAST ANNUAL FLOW 3,000 220 100 8 ANNUAL FLOW 1,000 750 50 5 Academy Member Deal Closed Investable Deal S1 · ACQUISITION INVESTMENT ACQUISITION STRATEGY Boardroom Member Personalized Advisory Needs Expansion Capital S2 · EXPANSION INVESTMENT EXPANSION STRATEGY WE FUND <1% OF OUR FUNNEL
Our Operators  ·  The Academy

Who Comes Through the Academy

Six operator profiles our funnel identifies and serves at the Academy, drawn from analysis of thousands of sales-discovery calls.

The Corporate Escapee

Analytical mid-career professional with capital, comparing acquisition to the next asset class, not escaping a life, building one.

The Existing Operator

Already owns a business or real estate portfolio. Looking for a second cash engine that doesn't take their time.

The Blue-Collar Climber

Tradesperson, shift worker, or gig grinder who wants to own a boring business that respects how they already work.

The Layoff Refugee

Recently displaced corporate or tech worker on a severance clock. The highest-urgency buyer in the funnel.

The Second-Acter

Pre-retirement professional looking to convert a career's worth of capital into an owned business for the next chapter.

The Family Provider

First-generation builder acquiring a business as long-term security and legacy for the household.

Our Operators  ·  The Boardroom

Who Comes Through the Boardroom

Six operator profiles our funnel identifies and serves at the Boardroom. Owners already in the work.

The Stuck-at-$1M Founder

Main-street owner-operator between $500K and $2M, still in the field. Needs SOPs, hiring, and a way out of the work.

The Roll-Up Builder

Operator stacking multiple acquisitions in a single vertical to build a regional or category platform.

The Multi-Venture Sophisticate

Runs several businesses already. Wants peer access, curated deal flow, and structured conversations, not curriculum.

The Plateaued Veteran

Long-tenured operator whose business has hit a ceiling. Needs the playbook to break it open or to sell.

The Exit-Prep Operator

Owner preparing the business for sale in the next 1–3 years. Wants the structure, packaging, and buyer network.

The Zero-Traction Builder

Owner who has been operating but making very little headway with the business. Wants help kickstarting their traction.

The Strategy

We Build Conviction Before We Deploy

We build conviction through our Academy and Boardroom, forming months- or multi-year-long personalized relationships before deploying capital.

HIGH MID LOW CONVICTION ADMITTED TO ACADEMY S1 INVESTMENT ADMITTED TO BOARDROOM S2 INVESTMENT TIME →
Identify and qualify high-quality Academy operators before they are even admitted into Academy, enabling diligence before Day 1.
Months of cohort work, deal reviews, and diligence involvement before we invest. By the time we fund, we have a deep understanding of how each operator will perform.
Continuous inside view of the funded businesses, with senior advisor reviews and operating data flowing back to us helps us build conviction for a much larger check.
Conviction is at its peak. By now we've built deep relationships over hundreds of touchpoints, with numerous advisors to lean on for additional diligence before the larger check goes out.
Why Us  ·  The Moat

Structurally Exclusive

An ecosystem years in the making, compounding into an advantage capital alone cannot replicate.

Layer 01

Audience

13M followers and 130M monthly views, compounded over years of content. This is a top of funnel a new entrant cannot buy or shortcut.

Layer 02

Trained Operators

We train and credential thousands of operators before a dollar is ever invested. The buyer pool is ours because we built it.

Layer 03

Dealflow & Data

Proprietary pipeline plus the accumulated signal of every member, deal, and business we track. A new fund starts with none of this history.

Layer 04

Embedded Operating Support

We stay embedded from first contact through exit, helping operators acquire and then scale. The relationship outlasts the check.

13M+ Followers
5,000+ Academy & Boardroom Members
Proprietary
Data Access
250+ New Acquisitions Per Year
Risk Profile  ·  Mitigation

How We Reduce Default and Improve Returns

The SBA qualification is our baseline. We fund a small, trained, and ambitious subset, and we structure our investment to protect the downside.

Selecting the Top 1%.

Our funnel is large, but the investment selection is small.

  • 4,000 members
  • 40 investments per year
  • <1% funded

Trained Before They Buy.

Operators complete acquisition training before they ever deploy capital.

  • 12-week acquisition curriculum
  • SBA underwriting training
  • Quality-of-Earnings review before close

Embedded After We Invest.

We maintain near-real-time visibility into performance long after closing.

  • Monthly operating reporting
  • Direct advisor access
  • Real time portfolio benchmarking and tracking

Structured for the Downside.

Our capital is structured to preserve value even when outcomes fall short.

  • Liquidity preferences
  • Valuation floors
  • Performance step-ups
Value Creation  ·  Exit

Assisting With the Exit

For a minority investor, the only question that matters is how the money comes back. We build three ways to return it, and just one of them needs an outside buyer.

We own the exit path...

160K Users (and growing)
01 The Buyers

We Run the Buy-Side.

  • BizScout sources and closes deals
  • Private Client advises funded buyers
  • A standing pool ready to acquire
  • Major brokerage partnerships
Transworld Business Advisors Sunbelt Business Advisors
02 The Business

We Build It to Be Sold.

  • Boardroom cleans up financials and ops
  • Add-ons and recaps lift the value
  • Packaged for strategics and roll-ups
  • Built to sell, not patched together
03 The Structure

Liquidity, With or Without a Sale.

  • Preferred equity sits ahead of common
  • Defined dividend pays income while held
  • Put-right buys the fund out at a set price
  • Recap or refinance returns principal
The Platform  ·  Academy

The Academy Platform

The end-to-end system that trains and equips every operator before they buy.

Course Material
Course Material

A guided curriculum built like an MBA on buying businesses. Takes members from zero to ready in days, not years.

Embedded Marketplace
Embedded Marketplace

Curated listings, automatically screened against each member's buy box, with direct in-app connection to the seller.

Academy Dashboard
Academy Dashboard

The member home page. Fully customizable to track the deals, metrics, and milestones each member cares about.

The Platform  ·  Boardroom

The Boardroom Platform

The operating system that helps every funded business grow, with continuous visibility for the fund.

Operator Scorecard
Operator Scorecard

A no-nonsense evaluation of the operator and their business, surfacing strengths and clear areas for growth.

Trailing 12-Month P&L Analysis
Trailing 12-Month P&L Analysis

Automatically pulled and tracked, surfacing the pain points hidden in the operator's financials.

Growth Strategy Roadmap
Growth Strategy Roadmap

An advisor-tailored growth plan designed specifically for each business in the Boardroom.

Our Operators  ·  Academy Deal Examples

Recent Academy Acquisitions

Three representative deals sourced through the Academy funnel.

The Corporate Escapee

Custom Window Tinting

Irvine, CA

OC Tint Shop
Revenue$3.0M
Net Profit$1.0M
Purchase Price$3.5M
Multiple3.5×

The Blue-Collar Climber

Kitchen Cabinets

Miami, FL

Acacia Kitchen Cabinets
Revenue$2.1M
Net Profit$0.5M
Purchase Price$1.9M
Multiple3.8×

The Family Provider

Garment & Gear Repair

Vancouver, BC

Gear Re-Store
Revenue$6.8M
Net Profit$1.1M
Purchase Price$4.6M
Multiple4.2×
Our Operators  ·  Boardroom Examples

Current Boardroom Members

Three representative businesses already inside the Boardroom and visible to us.

The Multi-Venture Sophisticate

Building & Construction

Denver, CO

Colorado Drain Systems
Revenue$5.0M
Net Profit$0.5M
# Employees30
Months in Boardroom12

The Exit-Prep Operator

Landscaping Services

Minneapolis, MN

Hartigan Outdoors
Revenue$6.8M
Net Profit$1.2M
# Employees<10
Months in Boardroom9

The Plateaued Veteran

Building Material Distributor

Pittsburgh, PA

Angels Distributing
Revenue$10.8M
Net Profit$2.5M
# Employees25
Months in Boardroom4
Risk Profile · Loss History

34 Years of SBA 7(a) Default Rates

Defaults spiked in a different underwriting era and have held at 3–5% for a decade since.

5.0%
CURRENT · FY2025
4.4%
34-YEAR AVERAGE
12.0%
MAX · FY2010 · GFC
DEFAULT RATE · FY1992-FY2025
12% 8% 4% 0% POST-2015 UNDERWRITING REFORM → '92 '01 '10 '15 '20 '25
Main Street Holding Co.

The Team

A disciplined team of operators and investors with institutional pedigree, media reach, and hands-on experience.

Codie Sanchez

Codie Sanchez

Founder, Contrarian Thinking

15 yrs · Institutional Investing

Managed ~$1B in EM assets

Investing Media Brand Building Recruiting
Goldman Sachs Vanguard
State Street
Chris Petkas

Chris Petkas

General Partner, CT Capital

8 Yrs Special Forces + 5 Yrs Operator

Prior: Head of AI Portfolio, DIU

AI / ML Hardware Investing Operations
Axon Defense Innovation Unit
U.S. Navy SEAL
Marc Hustvedt

Marc Hustvedt

President, Contrarian Thinking

20 yrs · Digital Content & Media

Prior: President, MrBeast

Media Content Growth Partnerships
MrBeast Streamy Awards
React Media
Alex Hooper

Alex Hooper

Head of Boardroom

6 Yrs Special Forces + 5 Yr Operator

Prior: GM, Apex Service Partners

Operations Roll-Ups Value Creation Management
Uber U.S. Army Special Forces
Vista Equity Partners
Rylan Harvey

Rylan Harvey

Head of Academy

10 yrs · IB, FP&A, Corp Dev

Built & led M&A teams, US & Canada

M&A FP&A Corp Dev Financing
BMO
The Chill Brothers
Armin SR

Armin SR

Chief Financial Officer

12+ yrs strategic finance and accounting

Built & led multiple accounting teams

Accounting FinTech Systems Integration
High Fortitude inKind
Urban Moment
Jordan Gregory

Jordan Gregory

Analyst

5 Yrs · SBA Lending

Built & scaled lending relationships

Lending Financing SBA 7(a) Structuring
Capital LDC sb
United Heritage Credit Union
Main Street Holding Co.

The Full Team

Head of Operations Head of Growth Head of Boardroom Chief Financial Officer Head of Academy Head of Content + 5 + 8 + 8 + 1 + 7 + 15 Partner Associate Chief of Staff Head of Finance 55 FTEs 5 FTEs
Main Street Holding Co.

Our Advisor Network

Rylan Harvey

M&A & Financing

Alex Hooper

Operations & Scaling

Carter Williams

Operations & Scaling

Travis Wheeler

Building Sales Teams

Stephanie Veal

M&A & Scaling

Candice Seiger

M&A & Operations

Dan Sullivan

Real Estate & Scaling

Hants White

Deal Structuring & Operations

Robert Clinkenbeard

EOS & Scaling

Nick Carey

Business Brokering

Robert Schiller

Operations & Scaling

Stan Sanchez

Operations & Real Estate

Fund Terms

Fund Overview

01
$40M
TARGET FUND SIZE
02
40 – 50
TARGET INVESTMENTS
03
8%
LP PREFERRED RETURN · HURDLE
04
15 – 18%
TARGET NET IRR
Value Creation  ·  Exit

How We Exit

Four paths to generate returns throughout the lifecycle of the fund.

Pre-agreed exit

Put Right

Structure in a put right to our agreements that allows us to exit on a pre-agreed time and valuation range.

During the hold

Dividends

Encourage, and structure in, quarterly or annual dividend payments to generate early returns.

At exit

Acquisition

The portfolio company sells, and we exit alongside the transaction.

Mid-hold liquidity

Minority Recap

The portfolio company recaps us out of the business with debt or other investors.

Appendix
Case Study

HealthNet Medical Clinic  ·  Primary Care Platform

Physician-founded, three-clinic primary care platform in San Antonio. 35% EBITDA margin. Sourced through the Academy.

$18.0MEnterprise Value
6.0×EBITDA Multiple
$3.0MTTM EBITDA
35%EBITDA Margin
$3.6MCo-Invest Raise

Physician-founded, three-clinic outpatient primary care platform serving 11,900+ active patients with 4,000+ visits/month across fast-growing San Antonio submarkets.

  • ·Revenue grew $5.5M to $8.4M over four years.
  • ·EBITDA grew 2.3×. 34% of revenue from recession-resistant cash-pay services (immigration physicals, FAA certifications, HRT) behind credentialing moats.

Radhika Alla. Long-time Academy Member. Background at Mayo Clinic and Cigna.

Dr. Vamsee Alla, M.D. 20+ years of physician leadership at the CT VA. CMO.

Dr. Jose Reyes (founder) rolls 20% equity with a 3+ year transition.

Base Case 3–5×
  • 3 clinics only
  • EBITDA to ~$4.0M
  • Exit at 7–8×
Growth Case 7–10×
  • 6 clinics
  • EBITDA to $6.2M
  • Exit at 10–12×
Senior Debt
$7.2M · 40%
Subordinated Junior Tranche
$2.3M · 13%
Co-Investors
$3.6M · 20%
Seller Rollover
$3.6M · 20%
Buyer Equity
$0.9M · 5%
Seller Note
$0.4M · 2%
Appendix

Shortlist of Potential Boardroom Targets

We have a healthy pipeline of deals like the following 10.

# Industry Employee Location Revenue ($) Net Income ($) Net Margin (%)
1Building and Construction50–100CA15,000,0003,000,00020%
2Accounting and Tax Practices5–25PA4,500,0002,681,39960%
3Wholesale and Distributors5–25PA8,285,0002,366,00029%
4Gyms and Fitness Centers50–100TX8,000,0002,300,00029%
5E-Commerce Sports Store25–50TX20,000,0002,200,00011%
6Full Service Freight25–50NV4,800,0001,500,00031%
7Steel Piping & Fabrication50–100KY16,000,0001,250,0008%
8Industrial Maintenance5–25OH7,500,0001,200,00016%
9Dental Practices5–25TX4,000,0001,000,00025%
10Building and Construction5–25MD3,500,0001,000,00029%
Appendix  ·  Growth Boardroom