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

Round Size

Round size is the total capital raised in a financing, with right-sizing involving balancing runway needs, valuation impact, dilution, and milestone achievement.

Roadshow

A roadshow is the intensive 1 to 2 week period during which executives pitch institutional investors sequentially, used most formally in IPO processes.

Roadmap Planning

Roadmap planning is the process of prioritizing and sequencing initiatives across product, engineering, GTM, and other functions over a defined time horizon.

Right of First Refusal

A right of first refusal (ROFR) is a contractual right held by the company or investors to match any offer to purchase shares before they can be sold to a third party.

RICE Framework

RICE is a prioritization scoring model developed at Intercom that ranks product opportunities using Reach × Impact × Confidence ÷ Effort, producing a numeric score across a backlog.

Reward-Based Crowdfunding

Reward-based crowdfunding is the model where backers receive a product, perk, or experience in exchange for their pledge rather than equity (Wefunder/Republic) or nothing (donation), exemplified by Kickstarter and Indiegogo.

Reverse Vesting

Reverse vesting is the mechanism where founder stock that's already been issued becomes subject to a vesting schedule, with unvested shares subject to company repurchase if the founder leaves.

Reverse Stock Split

A reverse stock split is a corporate action that reduces share count by a defined ratio while proportionally increasing per-share value.

Reverse Merger

A reverse merger is a transaction in which a private company acquires a public shell company to go public without a traditional IPO process, increasingly rare in 2026.

Revenue Recognition

Revenue recognition is the accounting principle that determines when revenue is counted on the income statement, governed by ASC 606 in the US.

Revenue Forecast

A revenue forecast is a projection of future revenue over a defined period, ideally built bottoms-up from specific drivers (customer counts, ARPC, churn) rather than tops-down market-share assumptions.

Return On Ad Spend

Return on ad spend (ROAS) is revenue generated divided by advertising spend, used to evaluate the efficiency of paid campaigns.

Retrieval-Augmented Generation (RAG)

RAG (Retrieval-Augmented Generation) is the technique of retrieving relevant context from a knowledge base and including it in LLM prompts, the dominant pattern for knowledge-grounded AI applications.

Retention

Retention is the percentage of users or customers who continue to use a product or remain subscribed over a defined time window.

Restrictive Covenants

Restrictive covenants is the umbrella term for post-employment restrictions including non-compete, non-solicitation, confidentiality, IP assignment, and other provisions limiting former employee behavior.

Restricted Stock

Restricted stock is an outright grant of common stock subject to vesting and company repurchase rights, used primarily for founders and very early employees.

Restricted Stock Units

RSUs are a promise by the company to deliver shares (or cash equivalent) to the employee on vesting or a future liquidity event.

Repurchase Rights

Repurchase rights are contractual rights of the company to buy back shares from holders under defined conditions, most commonly unvested shares from departing employees.

Republic

Republic is an equity crowdfunding platform founded 2016 that operates under Reg CF, Reg A+, and Reg D, distinguished by its diversified portfolio across crypto, gaming, real estate, and startups.

Representations and Warranties

Representations and warranties (R&W) are contractual statements by seller (and sometimes buyer) in an acquisition about the state of the business, breach of which triggers indemnification.

Reporting Cadence

Reporting cadence is the regular schedule for reviewing metrics and business performance, with daily, weekly, monthly, and quarterly cadences each suited to different decision types.

Renewal Rate

Renewal rate is the percentage of customers or contract value that renew their contract at renewal time.

Remote Team

A remote team is one where employees work from locations outside a central office, often distributed across cities, time zones, or countries.

Regulation S

Regulation S is the SEC exemption for securities offerings made to non-US investors outside the US, allowing US companies to raise from international investors without SEC registration.

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