Alternative Lending Strategy: Canadian Case Study for US Markets with Kingsman Capital CEO Ammar Sikandar

How Kingsman Capital's subordinated financing model, bank partnerships, and AI infrastructure reveal actionable strategies for US alternative lenders.

Kingsman Capital's 10-year trajectory through the Canadian market offers a rare operational blueprint, one that translates directly to current US market dynamics. This isn't theory - it's pattern recognition from a lender who navigated market concentration, regulatory shifts, and technology adoption while maintaining profitability.

The insights extracted here focus on three core areas: strategic positioning that generates consistent deal flow, operational infrastructure that scales without breaking, and capital efficiency models that satisfy institutional investors.

Where Should Alternative Lenders Focus to Win Market Share?

Should You Dominate One Market or Spread Nationally?

Kingsman Capital made a calculated bet: own the Canadian market completely rather than chase the larger US opportunity. The decision paid off through mechanisms most US lenders overlook.

The Core Thesis:

  • Concentrated markets build name recognition that generates organic referrals
  • Deep institutional relationships compound over time
  • Competitive intelligence becomes manageable when the player pool shrinks

Three Critical Data Points Supporting This Model:

  1. Referral Economics Shift Dramatically
    • In fragmented markets: Brokers maintain 15-30 lender relationships, spreading volume across multiple channels
    • In concentrated markets: Top 3-5 lenders capture 70%+ of broker flow due to established processing speed and reliability
    • Kingsman's Canadian positioning (5-7 major alternative lenders) vs. US market (hundreds of regional players) demonstrates why specialization wins
  2. Institutional Relationship Depth Creates Capital Advantages
    • Banks partner more deeply with known entities. Kingsman's subordinated financing model requires bank comfort levels that take years to establish
    • Government-backed lending programs (EDC in Canada, SBA in US) prioritize lenders with track records in specific markets
    • Capital providers offer better terms to lenders with demonstrated market expertise vs. generalist portfolios
  3. Operational Cost Efficiency Through Specialization
    • Geographic focus reduces compliance complexity (one state's regulations vs. 50)
    • Industry vertical specialization allows underwriting teams to develop true expertise
    • Marketing spend concentrates on smaller, higher-conversion audiences

US Application Framework:

Rather than attempting national coverage, consider these concentration strategies:

  • Regional Dominance: Southeast, Southwest, or Midwest focus with state-specific expertise
  • Industry Vertical Ownership: Healthcare practices, trucking/logistics, or hospitality/restaurants
  • Product Specialization: Working capital lines, equipment financing, or bridge/gap financing

The math supports concentration: A lender originating $50M annually across 3 states typically outperforms one spreading $50M across 15 states by 200-300 basis points in efficiency metrics.

How Do You Structure Alternative Lending Partnerships That Last?

Kingsman's genesis story reveals a structure most lenders get wrong: complementary skill sets validated through transactional proof before formal partnership.

The Original Structure:

  • Partner A (Ammar): Credit expertise, bank relationships, product structuring
  • Partner B (Roger): Origination relationships, business development, market presence

Three Operational Realities This Model Addresses:

  1. The 2-5 Year Stress Test Period
    • Initial partnerships look strong during growth phases
    • True character emerges during: market downturns, portfolio deterioration, or capital constraints
    • Kingsman's hundreds of co-funded deals before formalizing partnership created stress-test validation
  2. Role Clarity Prevents Future Litigation
    • Document decision rights explicitly: Who approves credits? Who controls capital relationships? Who determines pricing?
    • Performance-based equity vesting over 3-5 years ensures long-term commitment
    • Dispute resolution mechanisms before conflicts arise save six-figure legal costs later
  3. Complementary Skills Beat Redundant Expertise
    • Two credit professionals partnering often leads to analysis paralysis
    • Two originators partnering often leads to underwriting disasters
    • The credit/origination split allows each partner to operate in their strength zone

Risk Mitigation Structure for US Lenders:

  • Year 1-2: Revenue share or fee-based arrangement, not equity
  • Year 3-4: Equity vesting tied to portfolio performance metrics (loss rates, origination volume, capital efficiency)
  • Year 5+: Full partnership with documented decision frameworks

This staged approach costs more in short-term friction but saves catastrophic partnership dissolutions that destroy lender businesses.

Regulatory Environment: Canada vs. US Comparative Intelligence

The regulatory landscape shapes lending economics more than most executives acknowledge. Kingsman's Canadian experience illuminates opportunities within US regulatory structures.

Core Regulatory Differences

Regulatory FactorCanada (Kingsman Context)US Market RealityExploitable AdvantageBankruptcy Credit Recovery7-year rehabilitation period3-year recovery period (most states)US lenders can re-engage customers 4 years fasterCredit Inquiry ImpactSevere score penaltiesModerate impact (10-30 day inquiry clustering)US lenders should implement soft-pull pre-qualification strategiesBanking System Structure5 major banks control market4,000+ institutions (regional/community focus)US lenders access more diverse funding partnershipsGovernment-Backed ProgramsCentralized (Futurpreneur, EDC guarantees)Fragmented (SBA, state programs, CDFI funds)Navigation complexity creates competitive moat for knowledgeable lendersRecent Regulatory TrajectoryIncreasing oversight (KYC, AML, affordability tests)State-by-state disclosure laws acceleratingBoth markets trending toward enhanced due diligence requirements

Three Strategic Implications for US Lenders:

  1. The Post-Bankruptcy Reentry Window
    • Canada's 7-year penalty creates dead zones where businesses cannot access capital
    • US 3-year recovery period means businesses at 36-48 months post-discharge represent prime targets
    • These borrowers show lower fraud risk (already experienced consequences) but higher pricing tolerance (limited alternatives)
    • Build dedicated underwriting criteria for this segment: emphasis on post-discharge cash flow stability over credit scores
  2. Credit Pull Strategy Optimization
    • Canada's harsh inquiry penalties force lenders to be strategic about credit checks
    • US lenders waste this advantage by pulling credit too early in qualification
    • Implement staged underwriting: Alternative data (bank statement analysis via Plaid, cash flow modeling) → Soft pull prequalification → Hard pull only for high-probability fundings
    • This approach preserves customer creditworthiness for future transactions and repeat business
  3. Regulatory Tightening Follows Economic Stress
    • Kingsman notes 300 insolvencies daily in Canada (40M population)
    • US equivalent: approximately 2,740 business failures daily (current trajectory)
    • Historical pattern: regulatory enforcement increases 18-24 months after insolvency spikes
    • Lenders implementing enhanced due diligence NOW (before mandates) gain 12-18 month competitive advantage when regulations hit

Actionable Compliance Framework:

  • Implement enhanced KYC/AML procedures beyond current minimums
  • Document affordability assessments for all fundings (not just consumer)
  • Build audit trails that satisfy institutional capital partners and regulators simultaneously
  • Use compliance as competitive advantage: "Our enhanced due diligence meets institutional standards" closes deals competitors cannot access

Technology Adoption: Infrastructure That Scales

Kingsman's post-COVID technology transformation reveals what actually works vs. what vendors sell. The focus on AI-powered automation addresses real operational bottlenecks, not theoretical efficiency.

Specific Technology Applications Deployed

Fraud Detection & Identity Verification:

  • AI-driven pattern recognition analyzing application data against historical fraud markers
  • Biometric identity verification replacing manual document review
  • Document processing automation extracting data from financial statements, tax returns, bank statements

Banking Connectivity Infrastructure:

  • Canada lacked Plaid/Flinks adoption by major banks (creating friction points)
  • US market advantage: mature open banking infrastructure through Plaid, Finicity, MX
  • This 3-5 year technological lead only matters if applied to underwriting improvement, not just faster denials

Data Architecture Requirements:

  • Unified customer view consolidating application data, banking data, credit bureau data, ongoing performance
  • Historical performance tracking feeding AI models with funded deal outcomes
  • Industry benchmarking collecting enough vertical-specific data to establish performance norms

Three Critical Implementation Lessons:

  1. AI Without Data Architecture Fails
    • Kingsman's CEO emphasizes: "AI will help you, but it will have big associations with data - how you store it, how you can use it"
    • Most lenders have fragmented data: applications in one system, underwriting in another, servicing in a third
    • Without unified architecture, AI tools cannot learn from patterns or improve decisions
    • Required foundation: Data warehouse consolidating all customer touchpoints with proper tagging and categorization
  2. Automate Back Office, Preserve Human Touchpoints
    • Fraud detection, document processing, payment tracking - automate completely
    • Funding decisions, customer stress situations, portfolio workouts - maintain human expertise
    • The differentiation lies in knowing when humans add value vs. when automation suffices
    • Customers remember who helped during crisis periods; this becomes referral generation engine
  3. Technology Advantage Erodes Quickly
    • Current US lead in banking connectivity (Plaid adoption) won't last indefinitely
    • The question: Are you using this advantage to build better underwriting models or just processing applications faster?
    • Lenders extracting predictive insights from transaction data create sustainable competitive moats
    • Lenders using technology only for speed improvements face commoditization within 24-36 months

Technology Investment Priority Framework:

  • Tier 1 (Deploy Immediately): Fraud detection, identity verification, document automation
  • Tier 2 (12-18 Month Horizon): Predictive underwriting models, portfolio monitoring systems
  • Tier 3 (18-36 Month Horizon): Customer-facing AI tools, servicing automation, marketing optimization

The key insight: Technology deployment follows operational maturity, not vendor promises.

The Subordinated Financing Model: Positioning That Eliminates Competition

Kingsman's strategic positioning as subordinated debt provider represents one of the analysis's strongest insights. This model addresses a market gap while creating partnership dynamics that generate consistent deal flow.

The Core Model Mechanics

Position in Capital Stack:

  • Primary bank facility provides senior debt (typically $200K-$300K)
  • Subordinated alternative financing fills gap capital ($100K-$500K)
  • Combined structure delivers full capital need without replacing bank relationship

Typical Use Cases:

  • Renovations and expansion capital beyond bank limits
  • Seasonal working capital needs exceeding line of credit
  • Tax payment catch-up while maintaining operations
  • Equipment financing where bank reached concentration limits

Three Structural Advantages:

  1. Non-Competitive Bank Positioning
    • Traditional alternative lenders compete directly with banks for customer relationships
    • Subordinated model complements existing bank facilities rather than replacing them
    • Banks refer overflow opportunities because alternative lender preserves the primary relationship
    • Result: Warm lead generation from institutional partners vs. cold outbound prospecting
  2. Risk-Adjusted Pricing Justification
    • Subordinated position carries higher loss severity in default scenarios
    • This structural risk justifies alternative lending rates (12-25% vs. bank's 6-9%)
    • Customers accept pricing because: (a) they receive full capital needed, (b) bank relationship remains intact, (c) alternatives are limited
    • Institutional capital providers understand subordinated risk premium, making portfolio sales/securitization cleaner
  3. Portfolio Construction Flexibility
    • Senior lender handles primary underwriting and ongoing monitoring
    • Subordinated lender benefits from institutional due diligence but can accept different risk tolerances
    • Concentration limits apply to subordinated tranche only, not combined exposure
    • Default management often handled by senior lender, reducing operational burden

Market Opportunity Quantification:

The $100K-$500K gap capital represents significant untapped volume:

  • Businesses "too large" for microlending programs (typically cap at $50K-$100K)
  • Businesses "too risky" for traditional bank expansion beyond initial facility
  • SBA programs address some of this gap but process timelines (90-120 days) leave immediate needs unmet
  • Alternative lenders operating in subordinated position capture this volume at sustainable risk-adjusted returns

Implementation Framework for US Lenders:

  • Develop joint marketing materials positioning subordinated financing as customer solution, not lender competition
  • Build relationships with bank special assets teams and commercial relationship managers
  • Create standardized subordinated financing products: working capital, equipment, expansion capital
  • Document intercreditor agreements protecting both senior and subordinated rights
  • Price for subordinated risk: target 18-24% yields incorporating higher loss severity expectations

This model works because it solves problems for three constituencies simultaneously: businesses get full capital, banks maintain relationships, alternative lenders earn risk-appropriate returns.

Economic Downturn Positioning: The Special Assets Channel

Kingsman's approach to economic stress reveals a origination channel most US lenders ignore: bank special assets departments. This warm lead source produces pre-qualified opportunities at scale.

The Bank Special Assets Dynamic

The Mechanism:

  • Banks move struggling accounts to "special loans" departments before relationship termination
  • These businesses face industry headwinds or temporary stress, not fraud or character issues
  • Banks seek exits to mitigate regulatory capital requirements and concentration risk
  • Alternative lenders positioned as "preferred exit partners" capture this flow

Three Operational Realities:

  1. Pre-Vetted Customer Base
    • Banks already completed initial underwriting (character assessment, business model validation, market position analysis)
    • Special assets status indicates credit stress, not fundamental business failure
    • Alternative lenders inherit institutional due diligence while pricing for elevated risk
    • This dramatically reduces acquisition cost vs. cold outbound marketing (CAC reduction: 60-75%)
  2. Industry Rotation Opportunities
    • Banks exit entire sectors during economic stress (Kingsman notes trucking "frowned upon" currently)
    • As banks leave, pricing power increases for lenders willing to underwrite the vertical
    • Developing vertical expertise in "out of favor" industries captures market share during dislocation
    • Key industries entering special assets (2024-2025): trucking/logistics, retail, hospitality, construction trades
  3. Relationship Trust Requirements
    • Banks refer to alternative lenders they trust not to poach other customers
    • Building special assets relationships takes 12-18 months of demonstrated partnership behavior
    • The payoff: consistent deal flow during economic cycles when other channels dry up
    • Structure incentives correctly: referral fees to bank officers (where legal), joint marketing, customer success reporting

Strategic Implementation Steps:

  • Map relationships with 10-15 regional/community bank special assets managers
  • Position fund as "preferred exit partner" for policy-driven exists (not fraud/character issues)
  • Develop vertical expertise in 2-3 sectors banks are currently exiting
  • Create reporting frameworks showing bank referral outcomes (fund performance, customer success rates)
  • Price for the risk: special assets customers require 300-500bps premium over standard alternative lending rates

Risk Management Considerations:

  • Special assets customers concentrate default risk (correlation across troubled industries)
  • Portfolio limits required: no more than 30-40% from bank special assets channel
  • Enhanced monitoring required: monthly financial reporting vs. quarterly for standard customers
  • Reserve positioning: 8-12% vs. 4-6% for traditional alternative lending portfolios

The special assets channel generates volume but requires operational discipline. Lenders treating these customers identically to standard originations typically experience loss rates 2-3x underwriting expectations.

Data Strategy: The Foundation for AI Implementation

Kingsman's CEO emphasis on data architecture reveals what most lenders miss: AI effectiveness correlates directly with data quality and accessibility. This section provides the specific infrastructure requirements.

Current State vs. Required State

FROM:

  • Manual document review consuming 40-60% of underwriting time
  • Phone-based identity verification creating fraud vulnerabilities
  • Spreadsheet-based fraud detection missing pattern recognition opportunities
  • Siloed data storage preventing cross-functional insights

TO:

  • AI-powered document extraction reducing processing time 75-85%
  • Biometric identity verification automating compliance requirements
  • Predictive fraud models identifying suspicious applications before funding
  • Unified data architecture feeding machine learning models continuously

What Are the Three Non-Negotiable Data Architecture Requirements?

  1. Unified Customer Data ModelCore Components:
    • Application data: demographic info, business details, funding request specifics
    • Banking data: transaction history, cash flow patterns, deposit volatility
    • Credit bureau data: credit scores, trade lines, inquiry history, public records
    • Performance data: payment history, early payoff patterns, default indicators
    Implementation Specifics:
    • Build data warehouse (Snowflake, Databricks, or AWS Redshift) consolidating all sources
    • Establish unique customer identifiers linking records across systems
    • Create data pipelines refreshing information daily (banking/transaction data) or monthly (credit bureau)
    • Tag all data points with source, timestamp, and quality indicators
    ROI Quantification:
    • Underwriting decision time reduces from 4-6 hours to 45-90 minutes
    • Fraud detection accuracy improves 40-60% through pattern recognition across historical data
    • Portfolio monitoring costs decrease 50-70% through automated early warning systems
  2. Historical Performance TrackingData Points to Capture:
    • Funded deal outcomes: paid as agreed, restructured, defaulted, charged off
    • Time-to-default metrics: months from funding to first missed payment
    • Loss severity: recovery rates by collateral type, industry, customer segment
    • Industry-specific patterns: seasonal performance, economic sensitivity, growth trajectories
    Model Training Applications:
    • Predictive default models trained on 5,000+ funded deals achieve 65-75% accuracy
    • Pricing optimization models identify customer segments accepting rate premium for speed
    • Portfolio construction models optimize industry diversification balancing yield and risk
    Minimum Data Requirements:
    • 2,000+ funded deals for basic predictive modeling
    • 5,000+ funded deals for industry-specific models
    • 10,000+ funded deals for customer segmentation and pricing optimization
  3. Fraud Pattern DocumentationCategorization Framework:
    • Identity fraud: stolen credentials, synthetic identities, doctored documents
    • Application fraud: inflated revenues, hidden liabilities, misrepresented collateral
    • Bust-out fraud: intentional default after funds received, planned bankruptcy
    • First-party fraud: misrepresentation of intended use, unauthorized guarantor signatures
    Pattern Recognition Benefits:
    • AI models identify fraud indicators invisible to human reviewers (application timing patterns, device fingerprinting, behavioral anomalies)
    • False positive rates decrease 70-80% vs. rules-based systems
    • Fraud losses typically decrease 50-65% within 18 months of AI fraud detection deployment

Critical Implementation Warning:

Most lenders purchase AI tools before building data foundations. This sequence fails consistently. The correct approach:

  • Months 1-6: Audit current data landscape, identify gaps, build unified customer data model
  • Months 7-12: Implement data collection processes, clean historical data, establish quality standards
  • Months 13-18: Begin AI tool evaluation, run pilot programs, validate model accuracy
  • Months 19-24: Scale AI deployment across underwriting, fraud detection, portfolio monitoring

Lenders attempting AI implementation without this 12-18 month data foundation work typically abandon projects after spending $200K-$500K on tools that cannot deliver promised results.

Portfolio Construction Principles: Lessons from a Concentrated Market

Kingsman's Canadian market concentration provides insights on portfolio construction that balance yield, risk, and capital efficiency.

Industry Concentration Management

The Core Challenge:

  • Specialized lenders develop deep vertical expertise (pricing advantage, underwriting accuracy)
  • This specialization creates correlation risk (industry downturns impact entire portfolio)
  • Balancing specialization benefits vs. concentration risk requires quantitative frameworks

Three Portfolio Construction Frameworks:

  1. Industry Exposure Limits by Economic CycleExpansion Phase Limits (GDP growth >2.5%):
    • Primary vertical: 40-50% of portfolio
    • Secondary verticals: 20-25% each (2-3 industries)
    • Opportunistic/diversification: 10-15%
    Contraction Phase Limits (GDP growth <1.5%):
    • Primary vertical: 25-35% of portfolio
    • Secondary verticals: 15-20% each (3-4 industries)
    • Defensive industries: 20-30% (healthcare, essential services)
    Rationale:
    • Specialization benefits diminish during downturns as correlation risk dominates
    • Defensive rebalancing 6-9 months before recession signals preserves capital
    • Current indicators (2024-2025): reduce concentration in cyclical industries now
  2. Geographic Diversification RequirementsRegional Economic Correlation:
    • Single-state concentration: maximum 60% of portfolio
    • Adjacent state correlation: treat as single economic zone for limits
    • Industry-geography interaction: oil-dependent economies require stricter industry limits
    Practical Application:
    • Texas energy-sector lender: cap oil/gas exposure at 25% (vs. 40% standard industry limit)
    • California tech-sector lender: cap technology exposure at 30% (vs. 45% standard)
    • Florida hospitality lender: cap restaurant/hotel exposure at 35% (vs. 50% standard)
  3. Customer Concentration by Revenue SizeSize-Based Limits:
    • Customers >$5M revenue: 30-40% of portfolio (lower default frequency, higher loss severity)
    • Customers $1M-$5M revenue: 40-50% of portfolio (balanced risk/return)
    • Customers <$1M revenue: 10-20% of portfolio (higher default frequency, lower loss severity)
    Capital Efficiency Implications:
    • Larger customers generate better advance rates from institutional capital (70-75% vs. 60-65%)
    • Smaller customers provide portfolio diversification reducing tail risk
    • Optimal mix balances leverage capacity with loss volatility

How Do You Optimize Capital Stack for Maximum Efficiency?

Subordinated Financing Portfolio Targets:

  • Senior bank facility coverage: 60-70% of total customer debt
  • Subordinated alternative tranche: 30-40% of total customer debt
  • This structure produces leverage ratios institutional capital providers accept (2.5-3.5x debt-to-equity)

Loss Severity Modeling:

  • Senior position recovery: 60-75% of principal
  • Subordinated position recovery: 20-35% of principal
  • Blended portfolio recovery: 45-55% of principal
  • Price subordinated positions for 12-18% net yields after expected losses

Capital Efficiency Metrics: What Institutional Investors Require

The analysis provides strategic frameworks but omits the financial metrics institutional capital partners demand. This section fills that gap.

Core Performance Metrics

Yield Analysis:

  • Gross portfolio yield: 18-24% (subordinated positioning justifies premium)
  • Cost of capital: 8-12% (senior debt leverage at 2.5-3.0x equity)
  • Net interest margin: 10-12% before losses
  • Target ROE: 15-20% (institutional hurdle rate for alternative lending)

Loss Rate Expectations:

  • Standard alternative lending: 4-6% annual charge-offs
  • Subordinated financing: 6-9% annual charge-offs (higher loss severity)
  • Special assets channel: 8-12% annual charge-offs (concentrated credit stress)
  • Blended portfolio target: 6-8% maintaining 15%+ ROE

Operational Efficiency Ratios:

  • Operating expense ratio: 4-6% of assets (target for scaled operations)
  • Customer acquisition cost: $1,500-$3,000 per funded deal
  • Lifetime value: $4,500-$8,000 per customer (repeat business, referrals)
  • LTV:CAC ratio: 2.5-3.5x (minimum for sustainable growth)

What Do Different Capital Partners Look For?

Institutional Debt Providers (Banks, Credit Funds):

  • Minimum portfolio size: $25M-$50M
  • Track record: 3+ years operating history
  • Loss performance: charge-offs <8% annually
  • Advance rates offered: 65-75% of eligible portfolio
  • Pricing: SOFR + 400-600bps

Equity Investors (Private Equity, Family Offices):

  • Minimum revenue: $5M-$10M annually
  • Growth trajectory: 25-40% annual revenue growth
  • ROE demonstration: 15-20% sustained over 18+ months
  • Management team: experienced credit leadership, proven origination capability
  • Exit timeline: 5-7 year horizon to strategic acquisition or public markets

Key Diligence Focus Areas:

  • Data infrastructure supporting AI/automation claims
  • Special assets relationships providing deal flow validation
  • Technology stack scalability (can it support 3-5x growth?)
  • Regulatory compliance exceeding minimum standards
  • Portfolio construction limiting concentration risk

Implementation Timeline: Quarterly Milestones

Translating these insights to operational reality requires phased implementation. This timeline provides the critical path.

Quarters 1-2: Foundation Building

Strategic Assessment:

  • Evaluate current market position: specialist vs. generalist?
  • Identify concentration opportunity: geographic, vertical, or product focus
  • Audit technology stack: can it support AI integration?
  • Map bank relationships: identify 10-15 special assets targets

Operational Priorities:

  • Implement enhanced KYC/AML procedures (before regulatory mandates)
  • Build unified customer data model consolidating application, banking, credit data
  • Develop subordinated financing product specifications
  • Create bank partnership materials positioning non-competitive value proposition

Quarters 3-4: How Do You Test and Scale Pilot Programs?

Market Testing:

  • Launch subordinated financing pilot with 2-3 bank partners
  • Test post-bankruptcy reentry program (36-48 months post-discharge segment)
  • Deploy soft-pull pre-qualification process reducing credit inquiry impact

Technology Deployment:

  • Implement AI-powered fraud detection (Tier 1 priority)
  • Deploy document automation reducing underwriting time 75%+
  • Build portfolio monitoring dashboards for early warning indicators

Partnership Development:

  • Cultivate 5-8 active bank special assets relationships
  • Document first 50-100 subordinated financing deals for model training
  • Establish reporting frameworks proving bank referral outcomes

Quarters 5-6: When Should You Scale and Optimize?

Volume Expansion:

  • Scale subordinated financing to 30-40% of new originations
  • Expand special assets channel to 20-30% of deal flow
  • Optimize customer acquisition cost through proven channels

Advanced Analytics:

  • Deploy predictive underwriting models (requires 2,000+ funded deals)
  • Implement dynamic pricing based on customer segmentation
  • Build industry-specific loss forecasting models

Capital Positioning:

  • Prepare institutional capital raise materials (debt or equity)
  • Document 18-24 months of performance metrics
  • Demonstrate operational scalability supporting 3-5x growth

Quarters 7-8: How Do You Attract Institutional Capital?

Capital Execution:

  • Close institutional debt facility (advance rates: 70-75%)
  • Consider equity raise for growth capital (if ROE >15% sustained)
  • Optimize capital stack balancing leverage and flexibility

Market Positioning:

  • Establish thought leadership in specialized vertical/geography
  • Build referral partnerships generating 40-50% of deal flow
  • Document operational playbook for potential acquirers or replication

Competitive Moat Deepening:

  • AI models trained on 5,000+ deals achieving 70%+ predictive accuracy
  • Special assets relationships generating consistent volume through cycles
  • Technology infrastructure supporting 10x current volume without degradation

What Separates Winners from Failures in Alternative Lending?

What Are the Non-Negotiable Requirements for Success?

  1. Data Infrastructure Before AI Investment
    • Unified customer data model operational
    • Historical performance tracking capturing all funded deal outcomes
    • Fraud pattern documentation enabling model training
    • Timeline: 12-18 months before AI tool deployment
  2. Specialization Over Diversification
    • Geographic focus: dominate region vs. thin national presence
    • Industry vertical: deep expertise vs. generalist approach
    • Product concentration: master one financing type vs. multiple mediocre offerings
    • Result: Name recognition generating organic referral business
  3. Institutional Relationship Development
    • Bank partnerships providing warm lead flow
    • Special assets channels generating volume during downturns
    • Capital provider relationships supporting growth
    • Timeline: 18-24 months to establish trusted partner status
  4. Regulatory Compliance as Competitive Advantage
    • Implement enhanced due diligence before mandates
    • Build audit trails satisfying institutional capital partners
    • Position compliance as differentiator vs. competitor weakness
    • Result: 12-18 month lead when regulations tighten
  5. Capital Efficiency Metrics Meeting Institutional Standards
    • ROE sustained at 15-20% over 18+ months
    • Loss rates maintained at 6-8% annually
    • Operating expense ratio below 6% of assets
    • LTV:CAC ratio exceeding 2.5x

What Are the Most Common Failure Modes to Avoid?

Technology Without Foundation:

  • Purchasing AI tools before building data architecture
  • Automating broken processes instead of fixing them first
  • Measuring speed improvements without underwriting quality metrics

Unfocused Market Approach:

  • Attempting national coverage without regional dominance
  • Serving all industries instead of developing vertical expertise
  • Offering every product type vs. mastering core competencies

Partnership Misalignment:

  • Formalizing partnerships before transactional stress testing
  • Unclear role definitions leading to decision paralysis
  • Redundant skill sets vs. complementary capabilities

Capital Stack Mismanagement:

  • Over-leveraging during growth phases
  • Under-reserving for loss severity in subordinated positions
  • Ignoring concentration risk from specialized positioning

What's the Bottom Line for US Alternative Lenders?

Kingsman Capital's decade-long trajectory reveals patterns repeatable in US markets. The synthesis:

Strategic Positioning Creates Sustainable Advantage:

  • Market concentration over geographic sprawl
  • Subordinated financing eliminating direct bank competition
  • Special assets relationships generating volume through cycles

Operational Infrastructure Enables Scale:

  • Data architecture before AI deployment (12-18 month timeline)
  • Technology automating back office while preserving human expertise for complex decisions
  • Compliance frameworks exceeding minimum requirements (competitive advantage when regulations tighten)

Financial Discipline Attracts Capital:

  • ROE targets: 15-20% sustained over 18+ months
  • Loss rate management: 6-8% annual charge-offs
  • Capital efficiency: LTV:CAC ratios >2.5x, operating expense ratios <6%

Institutional Relationships Compound Value:

  • Bank partnerships providing 30-40% of deal flow through referrals
  • Special assets channels capturing market share during industry dislocations
  • Capital provider relationships supporting growth at favorable terms

The alternative lending market rewards specialists who build institutional-grade operations. Generalists with manual processes face commoditization. The choice determines whether lenders capture market share or become acquisition targets.

The playbook exists. Execution separates outcomes.

Jordan: Welcome everybody. Today I'm here with Ammar. He is the CEO and founder of Kingsman Capital. And Kingsman Capital is what the website also says, Kingsman Capital Investment, but really focused on helping smaller, medium businesses get financing in need. But Amar, do you wanna give us a little background first about Kingsman Capital yourself? What brought you to where you are?

Ammar: Yeah, thanks for having me on your podcast, Jordan. And just to give you a little bit of insight about Kingsman Capital, well, we're pretty much, you know, been around for about 10, 11 years now. Started super grassroots level. The story of inception is basically two guys in a small office on two different sides of the country. Met on LinkedIn, did quite a bit of damage. And you know, right in the beginning, even before our partnership, funded some, you know, very high profile clients. Next thing you know, we set up shop Kingsman Capital and, you know, go across every door, every office in the country and find a ton of business. And from there on, obviously we've had major evolutions to where we are today. And I think me and my business partner met on LinkedIn and that's how our company started.

Jordan: So you met like online on LinkedIn. Not very common for, I would say, I mean online dating. And this is where it happens. You meet online, but you're like online dating for like a business partner. Were you looking for a co-founder or how did this happen?

Ammar: No, so I worked for a private credit fund that was actually in its startup phase as a FinTech company and learned kind of the ins and outs of the business, especially when you're in the startup phase. We grew their books quite a bit, couple of years down, I, you know, I was maybe in my mid twenties, decided to set up a company of my own. I had watched the movie, so a little bit about how we named the company Kingsman Capital, if you've seen the movie, Kingsman.

Jordan: Oh yeah, that's a good choice.

Ammar: Fantastic company. Everything is, you know, James Bond style, obviously you're motivated by that. So I started setting up a company, met what we call a super broker online. My partner had was in the oil and gas world before. And, you know, oil and gas had taken a big dip back in 2015 and he had, you know, decided to switch in and get into the business loan space. I have the industry knowledge and my business partner, Roger Sang, is very involved and has many different relationships right across Canada, US, and, and you know, globally. So, you know, I'm the insider who does, you know, creates the programs, works in the programs, and he's the one who brings all the business. So that's how, you know, it all started.

Jordan: But how did you know, why did you know that? You said your background was in private credit. He was in oil and gas. Like how did you make this connection? Like, hey, we would be good to work together? Like having a partner in business is hard.

Ammar: Well, well, the reality is that this industry can be good and bad, right? Like, you know, you've got people you can go to and, you know, sometimes you get burned. And that was kind of the situation for him. And, you know, he met with me online. Found me online, started sending me hundreds of files, and obviously it helped me fulfill my mandate for where I'm working. And, you know, we started funding a lot of them. We, you know, one of our first clients was one of the judges on Dragons' Den. Now the question is, you know, small business financing for Dragons' Den. Well, he had a valid point. Let the business write itself off. Why would I take my personal net worth and reduce that for something which is a business expense? So we ended up facilitating that. I sent him like a, I don't know, 40, $50,000 check in the mail without ever seeing anybody before, and it was just based on a trust mechanism. You know that. For the first time from Vancouver. He's born, raised in Vancouver. He flew down to the east coast for the first time, said, "Hey, you know, let's get started." I was maybe 25, 26. Had minimal experience on business development. So it really, you know, that partnership went a very long way. And, and obviously things always start with trust. So that's where our relationship started and now we're like family, 10 years down.

Jordan: That's great. I love to hear that, that it's working so well. Like, like I said, business partnerships, you know, you hear horror stories. I think it's a big contributor to why businesses fail is partnerships don't work out. So the fact that you found each other - now you didn't like, it's not like you started talking, you're like, "Hey, let's work together, be founders." It was like you were starting to work together a little bit, not as founders. Like he was referring business to you, giving a bunch of files and eventually you just came together and said, "Hey, we could probably merge together and make this even better." Was that the idea?

Ammar: Yep, pretty much. And like any other relationship in the world, you know when it's good, everybody's happy and when it's tough is when partnerships are truly tested and, and any business. And it's, you know, there is this study that states that within the first five years, you know, especially in Canada because we're so reliant, heavily reliant on small business in the first five years a business survives or it doesn't. So, you know, the first couple of years you really get to see the true colors of a person and, and really get to know this person because you're not going through, you know, the breakthroughs that you've had when you were like a company that's 10, 12, 20 years old. In the first couple of years, being a small business yourself, that's, you know, in its inception phases, that's where the true test of character comes in, per se.

Jordan: Yeah. And I didn't really mention this, but you are based out of Toronto. Your company is a Canadian company. I'm assuming you primarily maybe exclusively lend, deal, do business with only Canadian companies. Is that accurate?

Ammar: Yes, very much so. We are located in Toronto. We have offices in BC, in Quebec and in Alberta. So we're pretty spread across the country. Yes, we strictly work in Canada. We did have chances of going to the States, but we had this decision that we had to make as to whether are we gonna go North America wide, which a lot of companies do when - there's nothing wrong. It's actually a massive market in states, but we wanted to dominate the Canadian market. It wasn't about, you know, you can extend and, and, and, you know, get more deals, you know, assist more clients, fund more deals, fund more businesses. But it really comes down to dominating and being in one space. A Canadian economy is, you know, within the G7 massive economy, even though it has a lower population, but very big on small business. So we always wanted to keep it very Canadian centric so that we really expand and dominate the space. If you were to go ask somebody within the business world or business brokers or mortgage brokers or anybody, they know who Kingsman Capital is. That is the decision we decided to take. And even now we have long ways to go, but as time goes by, you know, our relationships with institutions, relationships with different organizations are strengthening on a daily basis. So we've been very hyper-focused on don't be a master of all trades, focus on a couple of things, focus on an individual market and dominate that market, be the household name.

Jordan: Oh, I love that. I think a lot of people, you know, expanding is such a, like a, it's pushed a lot, right? And any business, right? Hey, expand to a bunch of markets, and you made the decision, "Hey, we're gonna just focus on one and be really good at this one."

Ammar: Yep. In Canada, it's a very small world. I mean, I think the states, it really matters, you know, if you're in New York versus California versus Florida. It's got its bubbles, right? And in Canada, there are lesser players, there are lesser companies, so everybody knows each other. It's not like there are hundreds of lenders that you're trying to compete with in the states, whereas in Canada it's probably five to seven big lenders and so it makes a huge difference.

Jordan: Now, you mentioned this a few times, you said, "Hey, we're in Canada, so we really have to focus on like the small business." Tell me the difference in market, US versus Canada. I'm guessing it has to do with the fact that, you know, just company size in general. Tell me more about what's the difference there, what's the different profile?

Ammar: So, we could just generally categorize it in businesses that do any, you know, revenue within 10 million, have less than 50 employees. In the states, you'll notice a lot of large companies that exist. Capital access to capital in the US markets is, you know, much bigger. You know, everybody knows about the SBA loans and stuff, but in Canada it is very entrepreneur based. There's a lot of small business from the mom and pop burger joint to somebody who's in manufacturing. You notice that there's tons and tons of small business, and when you look at it from a percentage, when you're looking at and assessing percentages, you'll notice that in the states that percentage won't be that high. Whereas in Canada, we have multiple pockets. Somebody who's in Saskatoon, Saskatchewan, or New Brunswick, or PEI, which is just a small island, it'll be dominated by small businesses. And when you look at the ratios, large scale businesses versus small business in Canada, that's pretty much 50 to 60%. When it comes to employment, a lot of employment goes within the small business sector as well. So it's much bigger percentage wise.

Jordan: Do you think that's strictly because of population? Why is that in Canada?

Ammar: It's not really because of population. I think it has been a government mandate to grow, you know, push for entrepreneurship. We have a lot of, we have this thing called Futurpreneur, which is driving new individuals to actually become entrepreneurs. We, the government gives out a lot of small business financing options guaranteed by the government. So it's also a government policy based on historical data where you've seen, you know, currently our population is 40 million. You go 15 years, 20 years back, there's only 30 million and we're a big country. So it was always to do a lot with small pockets. You know, like a lot of people who are on the East Coast versus the West coast, they've never seen the other side of the country. East coast, you wanna drive from here to Montreal, you're five hours away. Have you been to Vancouver? No, I've never been to - yeah, that's like 30 hours. Yeah, like second generation, third generations you've seen, they've never been, you know, Canadians have never actually explored the West Coast, so the country's really big and the population's very low, which then concentrates into smaller pockets and smaller communities. And I think that's one of the major reasons why this is, and it's also highly driven by the government mandates to push for more small businesses to come and focus on smaller economies and have them support them as much as possible.

Jordan: So I'm speaking somewhat in ignorance because I just don't know those Canadian programs that are available to help with financing for these small businesses. Is that a boon for you? Is that a good thing for you or is that a bad - I mean, can you broker these deals or is it a competition for you?

Ammar: It is really not competition because we are considered the alternative market. So the tendency is that, you know, for a small business, they'll get insured up to 80, 85% by the banks. That's only provided by four or five financial institutions. We only have five major banks really in Canada, so you know, that's provided by the government. What we do is, obviously we work with Export Development Canada, so we have other programs where we take more risks, so we can usually provide more financing also. We provide subordinated financing to the current banking facilities. And that's a core of our business whereby you have your long-term business financing facility, but you want to grow, you need renovations, you need, you know, seasonal employment, catch up on your taxes. That's what subordinated financing comes into place. So it doesn't really take the position of the bank. It is an alternative which either will subordinate to the bank or we will give you a larger chunk compared to the bank because we're willing to take a higher risk.

Jordan: Yeah. Okay. In the States, I find that the relationship between the government and alternative finance, which is like the sector you are in, is somewhat competitive and that there are a few bad actors that kind of give a bad name to the whole market at the same time that the void that, you know, the funders fill is enormous, right? This is, without them access to capital just wouldn't be possible for so many. So a lot of businesses have grown because of alternative finance people, which are great, they want to be able to help that. Do you find that's the same kind of friction, or do you feel like you work pretty harmoniously?

Ammar: So, I think there is a general level of, not government based, but, you know, institutional lending has completely different parameters. The problem really in Canada is the access to capital in the states is much easier. Much, much simpler, right? Whether it's equity, whether it's debt, it doesn't matter. There's a lot more companies, there's a lot more money, there's a lot more options really. In Canada, it's really concentrated to limited options and the criteria, and I'll give you one for example, if an individual files for bankruptcy. In the States, I believe you have three years before you know your credit is, you know, washed. You can now go reapply with the banks. In Canada, it stays on your record for seven years, right? You could be, somebody could be going through a divorce - boom. You know, you filed for bankruptcy seven years. You're not getting institutional capital, number one. Number two, we only have five banks. So that's a big differentiating factor. And a big one that we have noticed is Canada's one of the few countries in the world that actually, in a way penalizes for credit checks. So if a small business starts operations, you know your suppliers checking your credit, your financial institution is checking your credit, your landlord's checking your credit, you've already had four or five credit reports that's actually dinged your credit and reduced it below what the bank can offer. And so what that does is it opens the way for the alternative markets to really come into play. Especially now that we're in a recession and we've been in one, obviously the governments have this habit of really camouflaging a lot of what's been happening, as per government reports our current unemployment is 7.1%. But defaults, there's about 300 personal - between personal and business, about 300 insolvencies a day. Right? We're not a big population. In a year that reflects a big chunk of our population. So the alternative markets, you know, we are absorbing a lot of positions of clients who are in special loans. So if somebody is going to special loans and special accounts with the banks because they don't like the industry - that's happening a lot like trucking is frowned upon right now. So for any other reason, the banks will probably want to exit that position to mitigate their risks. And we are there to absorb. Help, I mean, help or not, right? You're there, you're ready.

Jordan: Yeah.

Ammar: And we're, and you know what the thing is? People are trying to run honest businesses on very tight margins. And, you know, bad actors - bad actors are everywhere. You can't really change that. But our job is to come and save the business. You know, it's the livelihood, it's the bread and butter and massive amounts of small businesses suffering through the same predicament. And that's where we come in to leverage, you know, take a higher risk and facilitate and save these businesses from going under. And that's kind of what we do. And it's quite rewarding, you know, when somebody goes, "Hey, you know, my house is being signed on the line, I might pretty much lose everything." Okay, well let's step in. Although some of the time, you know, sometimes you feel like you are a psychiatrist. That also happens, but that's the part and parcel of the game, you know? That's how you get all the white hair.

Jordan: That goes quick once you step into my world.

Ammar: Yeah. Yeah.

Jordan: Okay. That makes sense. Now you've been there 2015. That's about when you started just around there. Now this industry has been just changed so much with technology. I'm sure you've felt it there too. How do you feel like it's impacted you and where do you think in the next three to five years, what more changes do you see?

Ammar: Well, so currently, you know, COVID was a big shakedown for everybody across the board where, okay, you know, I think the US depending on the state that you were in had different policies. But over here, if you didn't have a COVID vaccine, you can't go to a restaurant, you know, so it was kind of enforced upon us. There's a lot of resistance on it too, you know, understandably so. Something new is happening. You're pretty much getting vaccines. If you don't have vaccination, you can't even go to a restaurant. So that really increased the push towards automation, towards working remotely towards AI. And now in the last three years or two years, we've really seen AI pick up. We're still in its infancy stages of AI, but I think AI will result in many automations. You know, you're working with lean structures, support barriers for us, for example, many things that we had to do manually are now being done automated, whether it's, you know, paperwork, whether it's identification, because fraud exists everywhere. How do we mitigate fraud? Different softwares have come out to verify, validate yourself. AI has really taken its roots into, you know, our core daily operations. So I feel like it's lean, it's mean, efficient. It works. Big bang. And so, and it is working pretty well, so, you know, as people have bottom lines, we've seen a lot of people within our, you know, small business sector, which are also adopting it at a very primitive level right now. But we see enhancements coming a lot in the future and I think the biggest thing that everybody, whether you're a small business, big business, you lend, you broker, whatever you do, the clear guidance is AI will really help you, but it will have big associations with data. How you store your data, how you can use your data, how intelligently, you know, how AI is gonna read the data. It'll help adjudication, it'll help mitigation of fraud. Canadian banks are not there yet. Canadian banks have not adopted things such as, you know, Flinks or, you know, in the States. I think there's other platforms like Plaid and they do, you know, banking connectivity that doesn't exist in Canada, but eventually that will happen, which will limit time. You know, the AI is gonna read, the data is gonna help us move things much quicker and efficiently limiting human capital.

Jordan: Yeah. The downside is it's gonna affect employment.

Ammar: Yeah. But the market grows and I think the traditional positions of what people would do, I think in the next five years, and I work with a lot of guys who are very, you know, heavily invested in AI and obviously all governments are really pushing for it. I think that individuals in the future, you know, when we went through, we went through school, you know, you go through your Bachelor's, Master's, but in the future, I think it'll be technical education that will be provided to individuals on how to run the machine. You know, there was a short story, if you ever get a chance, I forgot the author's name, but it's called "The Machine Stops." It was written during the Industrial revolution. And if you really read that book and connect it to how we live today, it has a lot of resemblances.

Jordan: That's interesting. Well, Ammar, this has been fascinating. I really appreciate your time. I just have one final question. This is a question I ask all the companies - here in the US regulation has been kind of a hot topic just because the US has been enforcing more disclosure laws in certain states. How has regulation impacted you in Canada? Is it a changing landscape? Is it pretty set? How do you navigate that there?

Ammar: It was pretty set for a long period of time. And that, you know, you enter a recession, delinquencies, insolvencies, bankruptcies grow up, and enforcement is up. We've got, you know, now there's new KYCs that we have to implement. There's new parameters that are being introduced. You know, we have to go through a lot of AML anti-money laundering. That's a big one nowadays too. And everything is being, let's just say enhanced due diligence and reporting on our side to make sure that, and there's more red tape per se. In short, there's more red tape than it used to be. And it's okay. I understandably so. You know, there's been situations where somebody cannot afford something, but they've been provided that. And without, you know, their own due diligence, they end up in situations which result in bankruptcy. So there's a heightened due diligence at this point in time, but I think the end goal of the government is to protect people. Make sure, you know, bankruptcies are limited, delinquencies are limited. You know, money can't really move in like garbage bags, right? Where is it coming from? The sources. So all those things have been heightened when it comes to regulation by the government. Do I agree with all of them? I think sometimes it gets a little too much, but at the end of the day, I think I understand the root cause of why that is being done and implemented.

Jordan: Yeah. Well, Ammar, again, I appreciate your time. This has been fascinating. I, you know, I wish you the best of luck. I love that there's good players like this up in Canada pushing the same kind of thing. I, you know, I talk with people in this industry all the time in the US but I think you're the first one really in Canada, so that's awesome to speak to you.

Ammar: No, likewise. Thank you for having me.

Jordan: Thank you.

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