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Playbooks

Reference

The sessions behind the site

On this page
LAST REVIEWED 2026-10TRANSCRIPT BATCHES: DEC 2025 – OCT 2026

Every playbook synthesizes one or more live sessions. This index shows where each page’s material came from — speakers identified by role, per our sourcing policy.

Expert sessions

Section titled “Expert sessions”
DateExpertSession focusFeeds
Dec 2025Fractional PR agency founderDIY PR and founder narrativeDIY PR
Dec 2025Fractional CFO, ex-head of a ~50-person CFO practiceData rooms and financial controlsData rooms
Dec 2025Startup immigration attorneyFounder visas under policy changeFounder immigration
Jan 2026Startup securities attorney (15 yrs)Equity comp: RSAs vs. optionsFounder stock, Options & pools
Jan 2026Startup securities attorney (15 yrs)Equity comp deep dive, 409A, advisorsOptions & pools
Feb 2026Serial founder, multiple exits, P&Ls to ~$300MBuilding executive teamsExecutive team
Feb 2026Partner, national venture law firm (~19 yrs)SAFEs vs. notes vs. priced roundsSAFEs vs. notes
Mar 2026Startup securities attorneySAFE conversion mechanics and dilutionSAFEs vs. notes, Exits
Mar 2026AI marketing agency co-founder + head of growthAI-powered marketing for lean teamsAI-era marketing stack
Apr 2026Multi-exit SaaS founder ($75M+ ARR companies)The SaaS repricing and AI-era GTMSaaS repricing, Pricing
Apr 2026GP, pre-seed micro-fundHow micro-VCs decide; running a raiseHow seed VCs decide, Running the raise
Apr 2026Founder & revenue-podcast host (0→$1M ARR in months)Customer development as a sales funnelCustomer development
Apr 2026Managing partner, deep tech seed fund (~$300M AUM)Evaluating AI startups; moatsHow seed VCs decide, Data moats
May 2026Partner, mission-driven seed fundSeed traction bars; data-as-moat thesisHow seed VCs decide
May 2026Startup marketing agency founder (clients raised $250M+)Live landing-page teardownsLanding pages
May 2026Startup securities attorneyTerm sheets, red flags, cap-table mathTerm sheets
May 2026Exited founder; fundraising office hoursPre-seed tactics; first contractsRunning the raise, First customer contracts
May 2026Exited consumer-marketplace founderFounder storytelling; selling the companyRunning the raise, Exits
May 2026Two patent attorneys, IP boutiquePatent eligibility for AIPatents & IP
May 2026Startup immigration attorney & authorF-1/OPT/H-1B/O-1 pathwaysFounder immigration
May 202620-year enterprise CIOSelling to CIOs and CISOsSelling to the enterprise
May 2026Startup securities attorney83(b), vesting, pools, SAFE mathFounder stock, Term sheets
May 2026Member roundtable (anonymized)Data flywheels; early-customer proof pointsData moats, First customer contracts
Jun 2026Head of a bank venture-lending practice (~21 yrs)Venture Debt 101Venture debt
Mid-2026Serial founder, category-defining e-signature companyPricing and packaging deep divePricing and packaging
Mid-2026AI marketing agency co-founders + head of growthGTM for AI products; disrupting gatekept industriesMarketing an AI product, Pricing and packaging
Aug 2026Serial founder, category-defining e-signature company“Before you build it”: validation methodologyValidate demand before you build
Aug 2026Sales leader who built a public ed tech company’s mid-market teamTurning early traction into a repeatable sales motionRepeatable sales motion
Aug 2026Co-founder, deep tech seed fund (3 exits, engineer)Finding your first angel checkFirst angel check
Aug 2026Founding partner, Seattle pre-seed fundLive pitch-deck teardownsThe pitch deck, torn down
Sep 2026Three-exit founder, exit-readiness advisorHow and when to exitRunning the exit process, Exits
Sep 2026Venture partner and former enterprise seller (Workday, Microsoft, SAP)Converting a paid customer pilot to a purchase orderPilots that convert, Selling to the enterprise, Pilot vs. paid contract, Buying committee
Sep 2026Serial founder, category-defining e-signature companyWhen the search runs out of runwayWhen runway runs out, Default alive, Acqui-hire, Administrative dissolution, LTV:CAC
Sep 2026GTM strategist ($80M quarters and $500/month budgets); LinkedIn instructorGTM as a system, not a stack of tacticsGTM as a system, Blue ocean, Scatter-plot funnel, GTM hypothesis, Vitamin vs. painkiller
Sep 2026Cloud-deploy co-founders (prior startup acquired by Workday; Microsoft and AWS backgrounds)Why AI isn’t making the engineering process 10x fasterWhy AI isn’t making engineering 10x faster, Amdahl’s law, Meat proxy, AI-native, Engineering sovereignty
Oct 2026Venture investor and former founderLive pitch-deck reviews: opening insight, differentiation, growth strategy, marketplace durability, and asset ownershipThe pitch deck, torn down, How seed VCs decide, Data moats
Oct 2026B2B software operator and angel investorFundable milestones, use of proceeds, investor sequencing, protecting execution, and diligence readinessRunning the raise, First angel check, How seed VCs decide, Data rooms
Oct 2026Repeat founder and AI go-to-market operatorWorkflow mapping, scoped AI roles, shared context, approval boundaries, costs, editorial ownership, and sales preparationAI-era marketing stack, Marketing an AI product, Repeatable sales motion
Oct 2, 2026Venture investor and repeat founderPitch-deck review: teaser versus live dialogue, slide takeaways, revenue-based market sizing, audience context, founder commitment, and capital fitPitch deck review, How seed investors evaluate startups, Running the raise

Newly incorporated sessions

Section titled “Newly incorporated sessions”

These additions are incorporated in this October 15 editorial update. Dates for the conference, M&A, and pitch-review sessions are matched to the published session records; the coffee date is supplied with its transcript.

DateExpertSession focusFeeds
Oct 13, 2026B2B sales practitionerConference preparation, relevant conversations, agreed next steps, and follow-upConferences to customers, Enterprise selling, Repeatable sales, GTM
Oct 13, 2026Startup/venture and M&A attorneysTransaction counsel, funding and exit choices, IP, disclosure, and scoped cost estimatesStrategic partnerships and IP, Exit process, Exits and leverage, Data rooms, IP assignment, Buyer types, Customer concentration, Benchmarks
Oct 14, 2026Member roundtable, anonymizedDesign-partner commitment, budget owners, segment choice, partner incentives, work coordination, and agent-work ownershipFirst contracts, Enterprise selling, Buying committee, Repeatable sales, Executive team, AI engineering
Oct 15, 2026Pre-seed B2B software investor and former founderPitch clarity, evidence for customer outcomes, contracts behind traction, investor lenses, and forecast assumptionsPitch deck, Seed investor evaluation, Data rooms, Running the raise

What’s coming

Section titled “What’s coming”

The sessions continue weekly. Topics recorded or scheduled that will deepen this site next: contract negotiation and objection handling, and pricing strategy. If there’s a topic you want covered, VEN runs the room where it gets answered.