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

AdvisorBootstrappingCapital GainsCustomer ContractDebt FinancingESOPVendor ContractGenerative AiLarge Language ModelMachine LearningTransformer ArchitecturePrompt EngineeringContext WindowRetrieval Augmented GenerationAi AgentMultimodal AiInference CostGpu CostToken EconomicsAi WrapperAi SafetyAi AlignmentVibe CodingBusiness Model CanvasBlue OceanGo To Market StrategyMilestone PlanningRoadmap PlanningDashboardRevenue ModelAcvTcvBookings Vs RevenueRevenue RecognitionDeferred RevenueExpansion RevenueContraction RevenueLogo RetentionIndustry AnalysisVertical AnalysisSales PipelinePipeline CoverageSales Cycle LengthQuota AttainmentSales Led GrowthWorking CapitalAccounts ReceivableAccounts PayableDays Sales OutstandingSaas Quick RatioCash Conversion CycleProduct Market FitJobs FrameworkBoard DeckReporting CadenceWeekly Business ReviewMonthly Business ReviewStakeholder Vs ShareholderSolo FounderTechnical CofounderBusiness CofounderCfoCooVp EngineeringVp SalesVp MarketingChief Of StaffFractional ExecutiveInterim ExecutiveCofounder SearchCofounder DatingSuccession PlanningAccount ExecutiveSales Development RepresentativeBusiness Development RepresentativeCustomer Success ManagerHow To Build A Sales TeamEmployee Vs ContractorOne On One MeetingsOrg ChartSpan Of ControlRemote TeamDistributed TeamAsync WorkPhantom EquityProfits InterestsFounder SharesStartup EquityPost Termination Exercise WindowOption ModificationEmployee Stock Purchase PlanTransfer RestrictionsConsent RightsFounder ClawbackSupermajority VoteVoting RightsPreemptive RightsRegistration RightsDemand RegistrationPiggyback Registration

Articles

Preferred Stock

Preferred stock is the share class issued to venture investors in priced rounds, carrying economic protections (liquidation preference, anti-dilution) and control rights (protective provisions, board seats) that common stock lacks.

Preemptive Rights

Preemptive rights are contractual rights allowing existing stockholders to purchase their proportional share of any new equity issuance, preserving their ownership percentage; often overlapping with pro-rata rights in venture-backed companies.

Pre-seed Funding

Pre-seed is the earliest outside capital a startup raises ($250K-$1.5M typical), almost always on a post-money SAFE, sized to prove one specific milestone that unlocks the seed round.

Pre-money vs Post-money Valuation

Pre-money is what a company is worth before a new investment; post-money is pre-money plus the new money raised.

Post-Termination Exercise Window

The post-termination exercise window (PTEW) is the period after an employee leaves during which they can exercise vested stock options before forfeiture.

Pivot

A pivot is a structured course correction in product or business strategy in response to learning from the market, popularized by Eric Ries in The Lean Startup.

Pitch Q and A

Pitch Q&A is the question-and-answer section following a pitch, often more important than the pitch itself because it reveals how founders think under pressure.

Pitch Practice

Pitch practice is the systematic rehearsal of investor pitches with feedback, used to refine the pitch, build founder confidence, and surface questions before real investor meetings.

Pitch Iteration

Pitch iteration is the systematic refinement of the pitch deck and narrative based on investor feedback patterns, used to sharpen the pitch while avoiding Frankenstein decks.

Pitch Deck

A pitch deck is a 10 to 15 slide presentation used to communicate a startup's market, product, traction, team, and capital ask to potential investors.

Pitch Deck Financial Projections

The financial projections slide in a startup pitch deck shows the company's revenue, expense, and cash projections over a multi-year horizon, typically 3 to 5 years.

Pitch Coaching

Pitch coaching is the practice of working with an experienced advisor to refine a pitch deck, narrative, and delivery before high-stakes investor meetings.

Pipeline Coverage

Pipeline coverage is the ratio of qualified pipeline value to quota, used to evaluate whether reps have enough opportunities to hit their number. 3-4x is healthy.

PIPE Deal

A PIPE (Private Investment in Public Equity) is the purchase of stock in a publicly-traded company at a discount to market price by institutional investors needing fast capital.

Piggyback Registration

Piggyback registration is the right that lets preferred stockholders include shares in registration statements the company files, subject to underwriter cutbacks.

Phantom Equity

Phantom equity is a contractual right to receive cash payments tied to the value of company stock without granting actual ownership.

Performance Review

A performance review is a periodic structured assessment of an employee's performance, used for compensation decisions, promotion discussions, and developmental feedback.

Performance Improvement Plan (PIP)

A PIP is a formal document outlining specific performance expectations and improvement goals for a struggling employee over a defined period, typically 30-90 days, with consequences if not met.

Pay-to-Play

Pay-to-play is a provision requiring existing investors to participate pro-rata in future rounds or face dilution penalties such as conversion of preferred to common, common in down rounds.

Patent

A patent is a government-granted intellectual property right giving the inventor exclusive rights to make, use, and sell an invention for a limited period (typically 20 years from filing).

Party Round

A party round is a financing round with many small investors (10+ checks under $250K) and no single lead, common at seed and pre-seed stages.

Partnership

A partnership is a US business entity owned by two or more people, with variants (GP, LP, LLP) distinguished by liability structure and management authority.

Partner Meeting

A partner meeting is the meeting at a venture firm where the full partnership reviews a startup and votes on issuing a term sheet.

Partner Introduction

A partner introduction is connecting with a senior decision-maker at an investment firm rather than associates, dramatically increasing the chances of meaningful investment consideration.

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