Investor Office Hours w/ VSC Ventures & Fictive Ventures

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Darrel Frater ✝️
@DarrelFraterSep 8, 2025

The Spaces featured weekly investor office hours hosted by Daryl Freighter with two focused sessions. In hour one, Jay from VSC Ventures shared his thesis on automation/AI solving labor shortages in “dirty, dusty, dangerous” industries (incl. public safety), his evaluation pyramid (Team ~60%, Market ~30%, Product ~10%), and why storytelling that entertains, educates, and energizes is decisive in fundraising, hiring, and sales. He urged founders to start pitches with why they are uniquely qualified, do primary customer discovery (including with VCs), avoid jargon, and tailor to a fund’s model. Jay outlined VSC’s process (first call, deeper diligence, primary research, quick partner decision; typical $500k–$1M checks at seed). He then coached four one‑minute pitches (cloud certifications, space-management OS, embedded doc QA, internal mobility HR), emphasizing why‑now framing, human, off‑script delivery, and defensibility versus foundation models. Hour two featured Khadija Robinson and Brahm Rhodes of Fictive Ventures, a $5M first fund backing Black‑led tech at “idea‑plus” through early seed, often as first check, with value add via an LP network and hands‑on support. They stressed that not every startup should raise VC, revenue is the cheapest capital, AI claims must be real, and underrepresented founders must be deeply prepared and educated on alternative financing. They reviewed founder pitches in caregiving, edtech, live events fintech, medtech, B2B sales AI, and consumer credit, offering GTM, sales‑cycle, and business‑model guidance, and closed with resources, contact points, and an invite to Tulsa Tech Week.

Weekly Investor Office Hours — Summary and Notes

Key Participants and Roles

  • Daryl Freighter — Host; co-founder, Freighter Family Foundation (Tulsa, OK). Organizer of weekly investor office hours.
  • Jay — General Partner at VSC Ventures (seed-stage VC). Focus: “dirty, dusty, dangerous” industries; AI/automation; brand/storytelling value-add. Typical checks: $500K–$1M (primarily Seed, some Series A).
  • Tabeja Robinson — General Partner at Fictive Ventures (often addressed as “Khadija” in the session). Former lawyer and founder (exited The Nile List), EIR at Black Ambition; runs the LIFT incubator at the Center for Black Entrepreneurship (Atlanta). Raising a $5M fund investing in Black-led tech startups at “idea+” to early seed.
  • Brahm Rhodes — General Partner at Fictive Ventures; Director of Investments at Village Capital (builds funds incl. Malaysia Climate Fund). Long-time mentor/advisor across accelerators.
  • Founders who pitched:
    • Kevin — Canvas Cloud AI (hands-on certifications for cloud engineers)
    • Steven — Workspace (operating system for space management)
    • Vladimir — ElephantIQ (embedded doc QA; exploring e-commerce “Rufus”-like assistant)
    • Ayana — Metrics AI (internal mobility/skills visibility platform)
    • Francis — WithLove (caregiving coordination platform)
    • Cam — Dump Pal (tabletop TCG teaching kids to code)
    • Aaron — Pebble (B2B SaaS/fintech for live event vendor ops and revenue)
    • Ayesha — Casual Recovery (medtech: drain care + broader patient safety portfolio)
    • Raphael — Cassie AI (AI phone solution for B2B sales teams)
    • Antoine — Credit Genius (gamified AI credit mentor and monetization)

Session 1 — Jay (VSC Ventures): Philosophy, Thesis, Process, and Storytelling

Background and Fund Thesis

  • 11 years investing/working with startups; prior media/entertainment (NFL, Madison Square Garden). Brings high-level brand/media/storytelling expertise to early-stage companies as a long-term, aligned investor.
  • Core thesis (next 18–24 months): automation/AI addressing labor shortages in “dirty, dusty, dangerous” and generally unsexy industries.
    • Representative themes and investments: electrical contracting (AI for estimating/ops), automation in solar panel installation, industrial painting, recycling, public safety (law enforcement; sees “safer cities” demand accelerating).
    • Market insight: Public safety spend is commonly underestimated—departments have meaningful budgets but face undersupply because “everyone assumes they don’t buy,” so vendors don’t sell into them. Comparable public companies (Axon, Motorola, etc.) show market depth.

Sourcing and Evaluation Framework

  • RTOP: Team (≈60%), Opportunity/Market (≈30%), Product (≈10%). Rationale: at Seed, product will change frequently; prioritizes founder-market fit and market expansion potential.
  • Key criteria:
    • “Are you the best person to solve this?” Earned insight through lived experience, customer intimacy, domain history.
    • Markets are often underestimated. Best companies create/expand markets (credit to Hunter Walk). Convince how a $2B market becomes $20B if you succeed.
    • Product sense over product completeness: show customer discovery, interviews, records. Jay conducts primary research with prospective users and customers.
  • Small fund strategy: “Moneyball” — look where others aren’t; do your own work; don’t overpay for hot trends. “My job isn’t to catch the hot trend, it’s to make the hot trend.”

Storytelling as an Operating Advantage

  • People remember feelings, not facts (paraphrasing Maya Angelou). Founders must make messages memorable.
  • Three E’s framework: great stories should entertain, educate, and energize. Done well, storytelling powers both core startup jobs: build and sell.
    • Recruiting requires storytelling (great talent is irrational to join early; you must sell mission and impact).
  • Common mistakes:
    • Not tailoring to the audience (e.g., not understanding a fund’s check size, ownership targets, and return profile). Treat the VC like a customer; start with discovery questions.
    • Overusing jargon/buzzwords. Be simple and direct: “Here’s the problem; here’s how we solve it faster/better; here’s what we need to scale.”

1-Minute Pitch Guidance

  • Lead with: “Why are you the best person in the world to build this?” Then: why dedicate the next decade of your life to it?
  • Great answers combine passion with earned insight and action. Example: law enforcement founder who did ~60 ride-alongs to translate passion → insight → product.

Investment Process at VSC Ventures

  • Two partners collaborate Mondays/Fridays for pipeline review.
  • Typical process: Intro call → deeper follow-up within days → validation via customer calls and primary research → partner deep-dive (can we deliver on brand/storytelling?) → decision. 26 investments to date; ~7 more planned in current fund; raising Fund II next year.

Founder Pitches — Session 1 (with Jay)

Kevin — Canvas Cloud AI (Hands-on Cloud Certifications)

  • Problem: Traditional cloud certifications (AWS, OCI, GCP, Azure) lack hands-on validation → employers can’t trust resumes; talent mismatch persists amid cloud labor shortages.
  • Solution: Platform for hands-on certification and a public portfolio of cloud work (analogous to GitHub for code) to certify practical competence.
  • Market context: Cloud powers AI; multi-cloud adoption is high (93% on cloud; ~70% multi-cloud); supports AWS/Oracle/Google/Microsoft.
  • Feedback (Jay):
    • Strength: Earned experience (21 years at Oracle). Clear gap: certifications vs real skills.
    • Improve “Why now” and lead with market scale: juxtapose AI investment vs larger cloud footprint driving demand; quantify cost of mis-hiring and efficiency losses.
    • Paint the future: become the trusted talent pipeline and source of truth. Quantify lost dollars if possible.
    • Fit: Dev tools/sell-to-developer is not VSC’s strength; target investors who excel in dev tooling and developer GTM.

Steven — Workspace (Modern OS for Space Management)

  • Problem: Booking/operating workspaces is fragmented and outdated (1995-era processes; brokers’ slow response cycles kill deals).
  • Solution: Unified “OS” to search/book space, confirm availability, integrate vendors; integrations with Plaid (payments), Zapier (automation). Aspires to be Zapier + Plaid “for buildings” across coworking, events, commercial ops with zero-touch workflows and a single source of truth (pricing/availability).
  • Traction: University of Maryland and Howard University; reduced deal cycles 3–6 months → 15 days; saved customers >$100K in fees; ~$40K ARR; $4.4M qualified pipeline.
  • Feedback (Jay):
    • Strength: Deep, multi-role industry experience (Apple; WeWork; operations across many buildings). Clear articulation of who wins (end users) vs who loses (brokers bottlenecking deals).
    • Delivery: Answers were natural and compelling; the prepared pitch sounded scripted. Humanize the story (e.g., “we cut a 3.5-week tour wait to immediate booking”). Lead with your credibility and lived pain.

Vladimir — ElephantIQ (Embedded Doc QA; Exploring E-commerce Assistant)

  • Problem: Organizations and communities (e.g., HOAs) are buried under hard-to-search documents; static FAQs are out of date.
  • Solution: Create an “IQ,” upload documents (handles large files ~100MB), embed a site widget to enable semantic QA (live, public-facing FAQ). Considering a “Rufus”-like shopping assistant for product Q&A (inspired by Amazon’s Rufus).
  • Feedback (Jay):
    • Strength: Clear “why now” (AI-enabled semantic search); relatable examples (HOA rules about boating). Use both a big-enterprise example (e.g., Target) and a local HOA to show horizontal applicability.
    • Competitive angle: Prepare a strong moat vs ChatGPT/Claude native features. “When base models improve, how do you stay ahead?” Bigger docs and embedding are not enough—explain defensibility (data pipelines, integrations, governance, domain adapters, deployment control, analytics, etc.).
    • Investability: Horizontal document analysis is compelling; early customers may pull you into a vertical—be open but keep initial scope broad.

Ayana — Metrics AI (Internal Mobility & Skills Visibility)

  • Problem: Employees lack visibility into next roles; managers lack clear view of workforce KSAs; companies default to layoffs vs reskilling amid AI/automation.
  • Solution: “GPS for your career.” Employees upload resume → see internal openings + match level, skill gaps, development plan, coaching nudges; org-wide visibility into skills to redeploy/reskill.
  • Key insight: Breakdown in visibility accelerates around ~300 employees; multi-team visibility is critical beyond manager-level.
  • Feedback (Jay):
    • Strength: 25+ years HR experience; specific earned insight (the 300-employee threshold). Define ICP (e.g., 300–1,000 employees) and quantify TAM for that slice.
    • Strengthen “why now”: emphasize the cost/urgency of getting this wrong (layoff costs, morale/culture attrition, knowledge loss) and how AI/automation increases the need.
    • Fit: VSC hasn’t directly invested in HR tech, but sees value in a single source of truth for training/personnel management vs fragmented recruiting tech.

Session 2 — Fictive Ventures: Strategy, Criteria, Value-Add, and Landscape

Fund Overview and Mission

  • Team: Tabeja Robinson (GP; ex-founder, ex-lawyer, EIR Black Ambition; runs LIFT incubator in Atlanta) and Brahm Rhodes (GP; Village Capital; extensive mentoring).
  • Fund: Raising $5M. Invests in Black-led tech startups across the US at “idea+” through early Seed that create new markets or expand existing ones. Often first check.
  • Ecosystem model: Bench of all-Black investors; 250 LPs target; leverage LP expertise and networks (e.g., legal specialties, big tech credits) to open doors for founders.

“Idea+” — What It Means

  • Will invest pre-product and pre-revenue, but expects real validation: deep customer discovery, market understanding, and strong founder–market fit.
  • Signs of readiness: engaged conversations with potential customers, collected data/insights, clear articulation of problem/solution fit, awareness of distribution and sales cycle dynamics.

Value-Add and Support

  • Heavy involvement in 0→1: mentorship, troubleshooting, ideation, investor readiness, access to LP networks.
  • Goal: Prepare companies for scale and for later-stage investors who don’t do idea-stage.

Guidance on Fundraising and the Current Market

  • Not every company should raise venture capital. Many should pursue alternatives: profit-sharing, revenue-based financing, redeemable equity, etc.
  • “Seed-strapping”: raise only what’s needed, reach profitability early, avoid constant fundraising.
  • Focus obsessively on customers and revenue; let investors chase you once the value is clear.
  • On AI: don’t add “AI” unless it truly creates differentiated user value. Do leverage AI to create operational efficiencies and reduce capital needs.
  • Underrepresented founders must be extra prepared in a tight market: know when to raise, who to raise from, and ensure your case is bulletproof (validation, traction, clarity).

Founder Pitches — Session 2 (with Fictive Ventures)

Francis — WithLove (Caregiving Coordination)

  • Problem: During medical crises (e.g., stroke), families are overwhelmed. Communication, tasks, and medical notes scattered across texts/calendars → missteps, stress.
  • Solution: Single shared source of truth for caregiving: tasks, medical notes, updates, alignment.
  • Validation: Accepted into Bubble’s Immersive for Good program; demographic tailwind (17.5% of US population over 65 in 2025; rising family caregiver load).
  • Question: Partnering with Epic/MyChart.
  • Feedback (Tabeja): Healthcare enterprise integrations/partnerships have long cycles; plan for parallel GTM strategies to build traction while working the slow enterprise channel.

Cam — Dump Pal (Tabletop TCG to Teach Coding)

  • Problem: Underserved schools lack engaging, practical coding education; students perceive coding as “hard.”
  • Solution: Gamified, physical TCG (inspired by Roblox/Pokémon culture) to teach coding concepts and methods; prizes/tournaments to drive engagement.
  • Question: Sell to schools vs sell to parents?
  • Feedback:
    • (Tabeja) EdTech is tough: misalignment between users (students) and payers (schools/parents). Identify a segment with ability to pay and at scale; prove willingness to pay.
    • (Brahm) Kids must truly want it (consumer pull). Four testers aren’t enough—run systematic tests with dozens+ of students to validate engagement and outcomes.

Aaron — Pebble (B2B SaaS/Fintech for Event Vendor Ops & Revenue)

  • Problem: Organizers run complex vendor marketplaces on tools not designed for it (Eventbrite for tickets; Square for restaurants). Lacks vendor revenue capture, marketplace data, and unified experience.
  • Solution: Automates vendor registration, payments, revenue sharing, real-time insights, plus an AI engagement assistant (“Hey Pebble”). Business model: SaaS + take-rate on registration fees and transactions.
  • Traction: Piloted with 100+ vendors (Louvre Juneteenth Festival); 30+ events and 300 vendors waitlisted (incl. a very large US festival). Raised $120K (Next Cubed). Opening $1M pre-seed; targets $5M ARR in 18 months.
  • Question: Which slides excite investors?
  • Feedback:
    • (Tabeja) Decks don’t excite; clarity and evidence do. Show why customers will switch now, and how this scales quickly.
    • (Brahm) Every slide must support your core hypothesis (problem, solution, value capture, growth). Remove anything that doesn’t.

Ayesha — Casual Recovery (Medtech: Patient Safety & Recovery)

  • Problem: Post-op drains pinned to clothing and unmanaged; safety and dignity compromised; complications and slower healing.
  • Solution: Drain Care — utility-patented, FDA-registered, insurance-reimbursable replacement for pins, improving safety/comfort/dignity. UCSF study (n=30) showed faster healing, fewer complications, higher comfort vs old standard.
  • Portfolio: 7 issued patents, 12 pending across wound care and “rest of organization,” including a smart sleeve and Everyday Hero app that links inhalers/EpiPens directly to 911 (with GPS). Multiple awards (US and international). Won Black Girl Ventures pitch ($50K; program record). Speaking at USPTO’s Invention-Con 2025 on patient-inventor journey.
  • Question: Fit for Fictive; pitch feedback.
  • Feedback (Brahm): Strong problem and founder-market fit. Clarify business model focus: (1) scale one product as an operating company (venture path) vs (2) a licensing portfolio strategy (different investor profile and growth dynamics). Be explicit about which business you’re building.

Raphael — Cassie AI (AI Phone Solution for B2B Sales Teams)

  • Problem: Reps spend ~25% of time actually talking to customers; 75% on inefficiencies (bad mobile data, manual dialing, account research, CRM admin) → pipeline/revenue drag.
  • Solution: Validates mobile data, alternate dialing, and performs account research to connect reps with the right prospects at the right time; launch v1 on Oct 1.
  • Progress: 100+ customer interviews; raising $500K pre-seed (infra + 2 engineers + 1 designer) to accelerate product toward launch.
  • Question: Top founder habits from 0 → $1M ARR?
  • Feedback (Tabeja):
    • Relentlessness (the work is gritty; persistence is essential)
    • Ability to pivot (be focused but flexible; adjust means to achieve vision)
    • Coachability (listen to experienced operators; avoid hard-headed traps)
    • (Brahm add) Hold strong opinions loosely; pair conviction with adaptability. Demonstrate deep domain knowledge of customers and industry dynamics.

Antoine — Credit Genius (Gamified AI Credit Mentor)

  • Problem: Consumers see unexplained score changes in monitoring apps and seek guidance; monitoring ≠ mentoring.
  • Solution: Gamified, AI-powered mentor that explains events and actively guides users toward an 800 score. Monetization via upsells (trade-lines, boosts, funding offers). Both interactive and passive flows. Early traction: pilot since March, influencers, media features. Raising pre-seed.
  • Question to Brahm: Motivation behind Fictive’s model.
  • Response (Brahm): Build capital pathways and a community of Black investors with skills and insight to back high-potential founders. Not asking for a seat at the table—building a new table and inviting others to join.

Practical Takeaways and Action Items for Founders

  • 1-minute pitch essentials:
    • Lead with why you’re uniquely the best person to build this (earned insight + action taken).
    • State the urgent “why now” with stakes/costs if unsolved.
    • Describe the customer pain, your differentiated solution, and what you need (capital, intros, pilots).
  • In any investor meeting, start with discovery:
    • Ask about check size cadence, ownership targets, fund size/return profile, involvement style. Show you understand their “business model.”
  • Storytelling that works:
    • Use the Three E’s: entertain, educate, energize.
    • Humanize with vivid examples users can feel (e.g., 3.5-week wait for a tour vs instant booking).
    • Avoid jargon overload; be simple and direct.
  • Market and moat:
    • Don’t over-index on current TAM; show how you expand it if successful.
    • If built atop fast-evolving AI, articulate durable defensibility (data, workflows, distribution, integrations, compliance, UX lock-in).
  • Validation and traction:
    • Be systematic in customer discovery; keep records. Replace “four testers” with dozens+ and measurable outcomes.
    • For slow verticals (healthcare/edtech), pursue parallel GTMs to build momentum while long cycles unfold.
  • Fundraising strategy:
    • Honestly assess venture fit. If not, consider profit-sharing, revenue-based financing, or “seed-strapping” to profitability.
    • Underrepresented founders: be extra prepared. Know who to target and when; make your case bulletproof.

Resources, Contacts, and Upcoming

  • VSC Ventures (Jay): Active on Twitter and LinkedIn; publishes videos on storytelling, narrative, pitch improvement, brand/marketing. Open to feedback and content requests.
  • Fictive Ventures:
    • Website: fictiveventures.com (distinct applications for “idea+” vs pre-seed/seed). Email: [email protected]
    • LinkedIn: Connect with Tabeja Robinson and Brahm Rhodes.
    • LP/community model designed to open networks for portfolio founders.
  • Community and Events:
    • No office hours next week (host at leadership retreat). Returns on the 19th.
    • Tulsa Tech Week (week of the 22nd). Feature Day on the 23rd in Tulsa: founders meet investors, founders, and community leaders; exposure to the ecosystem.

Highlights

  • Jay’s evaluation weighting (Team 60% / Market 30% / Product 10%) and “make the hot trend” approach.
  • Storytelling framework: entertain, educate, energize; start investor meetings with customer discovery.
  • Concrete founder coaching moments that transformed pitches (e.g., Steven: be unscripted, human, and leverage deep ops experience).
  • Fictive Ventures’ “idea+” strategy: be first check for validated ideas; heavy networked value-add via a broad LP base; candid guidance that many startups shouldn’t raise traditional VC.
  • Consistent throughline: focus on customers and revenue; pair passion with proof; deliver crisp “why now,” and be coachable.