In their Q4 2025 investor letter, Greystone Capital introduces a new position in Shift4 Payments ($FOUR), highlighting it as a compelling opportunity in the integrated payments sector. Greystone Capital, known for their concentrated, differentiated investment strategy, presents Shift4 as a prime example of a misunderstood business trading at a significant valuation discount to its intrinsic value. The letter emphasizes the importance of distinguishing between tractable and intractable problems in business building, noting that Shift4’s 26-year evolution has created institutional knowledge and competitive advantages that cannot be easily replicated. Greystone’s decision to invest comes despite sector-wide weakness that has driven shares down over 40% in the past year, reflecting their commitment to identifying quality businesses at attractive entry points.
Investment Highlight: Shift4 Payments ($FOUR)
Business Overview
- Integrated end-to-end payments company founded in 1999 by Jared Isaacman (age 16 at founding)
- Leading provider of software and payment processing solutions across multiple verticals
- Founder-led with Jared Isaacman retaining ~30% economic interest and serving as Executive Chairman
- Powers billions of transactions for diverse small business and enterprise customers
Market Position
- #1 position in hospitality, sports and entertainment, and global luxury retail
- #2 position in restaurants
- Owns payment gateway layer, allowing structural positioning between merchant and acquirer
- 550+ software integrations across complex card-present and card-not-present environments
Performance Analysis
- Unique Business Model:
- End-to-end integrated payments platform combining gateway, processor, and POS software
- Absorbs complexity of disparate systems to deliver simplified solutions for merchants
- Retains larger share of transaction economics versus competitors who outsource processing
- Low merchant churn: 1.0% among top 50 customers, <3.0% total annual churn
- Unit Economics and Conversion Strategy:
- Gateway-only transactions generate lower gross profit per dollar of volume
- End-to-end processing generates meaningfully higher gross profit on identical volume
- Core growth lever: converting gateway-only customers to full end-to-end processing
- Superior unit economics drive accelerated financial performance relative to volume growth
- Financial Performance:
- Payment volume grown 4x since 2021
- Net revenue CAGR of ~41% annually since 2021
- Gross profit growth exceeded 60% since 2021, driven by end-to-end conversion
- Current valuation: mid-single-digit EBITDA multiple, ~10x 2026 earnings estimate
Growth Runway
- Organic growth potential in mid-to-high teens even without new M&A
- Large installed gateway base available for conversion to higher-margin end-to-end processing
- Continued vertical expansion through disciplined acquisitions
- Management target: $1.0 billion free cash flow run rate within next two fiscal years
Market Dynamics and Opportunities
- Market treating Shift4 as legacy, leveraged processor rather than high-retention platform
- Valuation gap versus peers (Toast at ~24x EBITDA vs. Shift4 at ~7x EBITDA)
- Path-dependent competitive advantages from 26 years of institutional learning
- Embedded workflows and meaningful switching costs protect market position
Valuation and Capital Allocation
- Current price: $63/share versus conservative 2028 target of $112-155/share
- Earnings power estimated at $8-11/share by 2028 under various scenarios
- Active $1.0B share repurchase program covering ~20% of shares outstanding
- Strong capital deployment track record: ~19% unlevered ROIC on $2.7B deployed since 2019
- Potential 21%+ three-year IRR under conservative assumptions
M&A Strategy
- Disciplined approach: build, partner, or acquire decision framework
- Focus on acquiring mission-critical software with embedded customer base
- Under-monetized payment flows converted to high-margin annuities
- Recent example: VenueNext acquisition for stadium vertical entry
- 2025 completion of largest acquisition to date: Global Blue
Risks
- Revenue more cyclical than pure software businesses due to transaction volume sensitivity
- Execution risk on Global Blue integration and merchant conversion
- Dependence on continued M&A success for upside scenarios
- End market exposure to hospitality, restaurants, and entertainment sectors
- Historical governance concerns (though recently addressed through elimination of multiple share classes)
Other Key Points
- Founder Jared Isaacman recently named NASA’s 15th Administrator
- Company has received acquisition offers in the past at prices below management’s threshold
- Multiple open-market share purchases by management during 2024-2025, including $16M in August 2024
- Since 2020 IPO, compounded shareholder capital at 20.5% annually, outpacing S&P 500 by 4% per year
- Track record of under-promising and over-delivering since IPO
- Hardware deployment and acquisitions used as primary customer acquisition tools versus traditional sales and marketing spend
Greystone Capital views Shift4 as a high-quality, misunderstood payments platform trading at a compelling valuation due to market misperception about cyclicality and business durability. They believe the company’s ownership of the full payments stack, accumulated institutional knowledge, strong unit economics, and founder-led management create an attractive long-term risk-adjusted return profile with potential for significant multiple expansion as execution continues.
