Ryan Rutan

CMO

Startups.com

About

Founding Partner @ Startups.com platform | Clarity.fm, Launchrock, Fundable, Zirtual, and Co-Host of The Startup Therapy Podcast. Ryan has 15 years of experience as a Founder, Advisor, Mentor, and Investor — the quintessential startup guerrilla. He works with 100's of the best startups every year on everything from ideation, idea validation, early marketing traction, customer acquisition to fundraising, scaling, and operations.

Expertise

Equity & OwnershipFoundationsProductCofounders & TeamBusiness PlanningFunding StagesExits & M&AAI StrategyLegal StructurePitchingAdvisorBootstrappingCapital GainsCustomer ContractDebt FinancingESOPGrowth MarketingNetwork EffectsVendor ContractAi StartupGenerative AiFoundation ModelLarge Language ModelMachine LearningTransformer ArchitectureTraining DataFine TuningPrompt EngineeringContext WindowRetrieval Augmented GenerationAi AgentMultimodal AiInference CostGpu CostToken EconomicsAi MoatData FlywheelAi WrapperAi SafetyAi AlignmentVibe CodingBusiness PlanBusiness StrategyBusiness Model CanvasLean CanvasSwot AnalysisBlue OceanGrowth StrategyGo To Market StrategyGtm MotionStrategic PlanningAnnual PlanningQuarterly PlanningScenario PlanningMilestone PlanningRoadmap PlanningOkrsKpisNorth Star FrameworkDashboardFinancial ModelFinancial ProjectionsRevenue ModelRevenue ForecastBottoms Up ForecastSensitivity AnalysisExpense BudgetPricing ModelPricing StrategyP And L StatementBalance SheetCash FlowArrMrrAcvTcvBookings Vs RevenueRevenue RecognitionDeferred RevenueExpansion RevenueContraction RevenueLogo RetentionUnit EconomicsCacLtvLtv Cac RatioCac PaybackMagic NumberRule Of 40Sales EfficiencyContribution MarginGross MarginEbitdaMarket ResearchMarket SizeMarket SegmentationTam Sam SomAddressable MarketIndustry AnalysisVertical Analysis

Articles

Equity Grant Policy

An equity grant policy is the documented framework for granting equity to employees, covering grant size by role/level, refresh policies, acceleration provisions, and consistent application across hires.

Equity Crowdfunding

Equity crowdfunding is raising small equity investments from many non-accredited investors via SEC-regulated platforms (Wefunder, Republic, StartEngine), enabled by the 2012 JOBS Act and Reg CF rules effective 2016.

Equity Compensation Tax Planning

Equity compensation tax planning is the practice of managing the timing and structure of equity-related tax events (option exercises, RSU vesting, sales) to minimize total taxes paid.

Equity Administration

Equity administration is the operational work of maintaining the cap table, processing equity transactions, managing option grants, handling 409A valuations, and ensuring securities compliance.

Enterprise Value vs Equity Value

Enterprise value is the total value of a business including debt and excluding cash; equity value is the shareholders' stake after debt is paid off and cash is netted out.

Employment Agreement

An employment agreement is a comprehensive contract governing employment relationships, used primarily for executives and international employees, more detailed than the simpler offer letter used for most US employees.

Employer of Record

An Employer of Record (EOR) is a third-party company that legally employs workers on a client's behalf in jurisdictions where the client has no entity, handling payroll, benefits, and compliance.

Employee Zero

Employee zero is the first non-founder hire who operates effectively as a founder-equivalent, working at founder-level intensity and ownership.

Employee vs Contractor

Employees and independent contractors are distinct legal categories with different tax treatment, benefits, and labor protections, and misclassification (treating employees as contractors) carries significant tax and legal penalties.

Employee Stock Purchase Plan

An Employee Stock Purchase Plan (ESPP) is a broad-based benefit allowing employees to purchase company stock at a discount (up to 15%) via payroll deductions.

Employee Handbook

An employee handbook is the document that codifies a company's policies, expectations, and procedures, serving both as employee orientation and legal protection.

Employee Equity

Employee equity is the ownership stake granted to non-founder employees in a startup, typically via stock options or RSUs, used as a recruiting and retention tool.

Email Marketing

Email marketing is the practice of sending targeted commercial messages to a permission-based list to drive activation, retention, repeat purchase, or referral.

Elevator Pitch

An elevator pitch is the 30 to 60 second verbal summary of a startup's business, used as the cold opening of investor or sales conversations.

EIN

An Employer Identification Number (EIN) is the 9-digit federal tax ID assigned by the IRS to a business entity, required for bank accounts, hiring, and tax filings.

EBITDA

EBITDA (Earnings Before Interest, Taxes, Depreciation, Amortization) is a measure of operating profitability used in valuation, debt analysis, and cross-company benchmarking.

Earnout

An earnout is a contingent acquisition payment tied to the acquired company hitting post-close milestones (revenue, EBITDA, product, retention) over a defined performance period.

Early Stage

Early stage refers to the phase of startup development from formation through Series A and early Series B, when product-market fit is the central goal.

Early Exercise

Early exercise is the action of exercising unvested stock options to acquire restricted stock subject to company repurchase if the holder departs.

Early Exercise Tax

Early exercise tax is the tax treatment of exercising stock options before vesting, with bargain element taxed at vesting unless 83(b) is filed.

Due Diligence

Due diligence is the investigation an investor conducts on a startup before investing, covering business, financial, legal, and technical risk.

Dry Powder

Dry powder is committed but undeployed capital sitting in venture funds, a metric watched as an indicator of future startup investment activity and overall venture-market capacity.

Drip Campaign

A drip campaign is a sequence of pre-written emails or messages delivered to a recipient on a defined schedule or in response to specific behaviors.

Drag-Along Rights

Drag-along rights are a contractual provision that lets majority shareholders force minority shareholders to join a sale on the same terms, enabling a clean 100 percent transfer.

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