Investor Office Hours w/ Fireroad Ventures & WIV Ventures

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Darrel Frater ✝️
@DarrelFraterAug 25, 2025

The Spaces brought together host Daryl Freeter and two investors—Christy Johnson (Fire Road Ventures) and Trey Icard (Wiv Ventures)—for a practical, founder-focused session. Christy traced her journey from nonprofit operations to launching Fire Road (2023) with a thesis that in an AI-native world, human-centric, locally rooted businesses become more valuable. Fire Road invests at inception in applied tech for service sectors and small businesses, often pre-revenue, with a fast, transparent, unanimous IC process and strong preference for domain-expert founders. She emphasized direct customer feedback, problem-first framing, and founders proactively asking VCs about process. Multiple founders pitched; Christy coached on early customer acquisition, validation KPIs, business cases to buy, lean AI-enabled teams, and B2C CAC/retention realities. In session two, Trey outlined Wiv’s early-stage fintech focus (pre-crypto), the realities of stewarding LP capital, and how he diligences: start with financials, look for growth signals, and a crisp plan including exit vision (5–7 years). He stressed fit (thesis, check size, deployment), referrals, regulatory fluency in fintech, and partnership mindset. Trey fielded pitches, advising on distribution through partnerships, leveraging event wins for intros, formation basics, execution over pedigree, and starting with friends/family to prove traction.

Weekly Investor Office Hours: Two-Session Recap and Insights

Hosts and Guests

  • Host: Daryl Freighter — Co-founder, Freighter Family Foundation (Tulsa, OK); former VC; mission-driven community builder. Runs weekly office hours every Friday (12–2 pm CT) to connect founders and investors, now in partnership with Adam and the startup community on X.
  • Guest (Session 1): Christy Johnson — Partner, Fire Road Ventures (launched 2023). Background in nonprofit leadership, product/marketing, founder support (Ocean Programs). Invests at inception in applied tech for service sectors and small businesses.
  • Guest (Session 2): Trey Icard — Managing Partner, Wiv Ventures (Austin, TX). Multi-time founder; former asset management and enterprise operator. Fund focus: early-stage fintech (transaction-centric, pre- or just at go-to-market), limited exposure to crypto.

Daryl’s Opening Context and Mission

  • Program origin and purpose: Began as personal office hours during the birth of Daryl’s first child; demand led to scalable Twitter Spaces format for open, repeated access to investors and peer learning.
  • Observed impact: Founders gain visibility, investor meetings, and network expansion via pitches here.
  • Personal why: Service-first, impact-driven commitment to entrepreneurs. Actively exploring research to correlate spiritual/mental health with financial outcomes in entrepreneurship.
  • Foundation: Freighter Family Foundation focuses on economic mobility and wealth-building through entrepreneurship in Tulsa.

Christy Johnson (Fire Road Ventures)

Background and Path to Venture

  • Spent ~10 years operating across nonprofit functions (volunteer mgmt., onboarding/training, risk/finance, fundraising, facilities, IT, digital products, marketing). Rapid learning-by-doing in scaling contexts.
  • Led marketing and digital products at a nonprofit; adopted lean design sprints, commercialized internal IP; discovered affinity for startup-style problem-solving.
  • Joined Ocean Programs (Cincinnati), a nonprofit serving both Main Street and high-tech founders. Learned the pivotal role of founder resilience (spiritual, mental, social health) in longevity and outcomes.
  • Co-founded Fire Road Ventures in 2023 with partner Tim (former founder/board member at Ocean) to invest very early and support holistic founder health.

Firm Thesis and Focus

  • Core thesis: In an AI-native world, human-centric businesses increase in value (not decrease) because they:
    • Build empathy and trust with customers
    • Preserve craftsmanship and local knowledge
    • Anchor local ownership and jobs, diversify communities, and reduce dependence on distant shareholders
  • Market gap:
    • ~1 million service-oriented SMBs change ownership annually
    • Next-gen operators are more tech-forward than previous owners
    • Yet ~35x more VC capital goes to enterprise tech vs. small business tech, even though SMBs account for ~50% of annual tech spend
    • Fire Road aims to deploy VC-style capital and support to small service-sector operators, addressing this investment-spend mismatch

Strategy and Stage

  • “Inception VC”: Comfortable at the idea/pre-revenue stage (about half of 23 portfolio companies were pre-revenue at investment).
  • Founder profile: Domain experts (often non-technical) with deep workflow fluency and strong networks in the sector they serve (prior operators/sellers into the market). Fire Road prioritizes founder advantage (not just “fit”).
  • Check size: $100–200K initial investments.

Process and Diligence

  • Sourcing: Primarily referrals, inbound web form, and deal-sharing networks.
  • Speed to “no”: Transparent, respectful triage—quick “no” when off-thesis (e.g., stage misfit, valuation too high, too late maturity).
  • Initial call (20 minutes): Assess problem clarity, founder motivations, deal parameters (round size, stage), and basic thesis fit.
  • Consensus approach: 3-person unanimous IC; introduce a second partner early to align before deep dives.
  • Diligence (30–45 days): Market size, competition, product viability, founder-market advantage; emphasizes problem validation (via LPs/operators) rather than product validation at very early stage.
  • Final meeting: All-hands with partners and founding team; ~20% of opportunities reaching committee still end in “no.”

Views on Main Street vs. High-Growth Tech

  • Universal founder challenge: Tension between assumptions and customer reality; many start with passion and “if we build it, they’ll come.”
  • Feedback loops differ:
    • Main Street: Short, conversational, face-to-face customer feedback—highly actionable.
    • High-growth/digital: Longer loops; instrumented testing; can feel abstracted from human context.
  • Advice: Talk directly to customers—high-growth teams often miss the power of direct, qualitative feedback.

Practical Advice for Founders

  • One-minute pitch content: State the problem and who it’s for—clearly and succinctly.
  • Ask about process: It’s appropriate to ask a VC about timeline, current check-writing status, required materials, and decision-making approach (consensus vs. single GP). Prioritize transparency and responsiveness.
  • Common mistakes:
    • Building the obvious without drilling down into a specific user/problem
    • Weak understanding of the buyer’s business case (e.g., reduced OSHA fines, less downtime, lower claims)—tie your value to tangible outcomes and integrate that language in sales/marketing
  • Team building in the AI era: Depends on product/market. Strong technical leadership (early CTO comfortable with AI/agents) can materially compress team size and boost revenue-per-employee (examples north of $1M/employee are emerging), but sales motion varies by vertical (e.g., adtech more field-heavy vs. HR tech).

Founder Pitches: Highlights and Feedback (Session 1)

  • Tasha (Socrates Advice): Team health-check platform delivers diagnostics and actionable recommendations; daily nudges for behavior change; seeking early customers and awareness pre-pre-seed.
    • Feedback: Prioritize face-to-face onboarding to 10–20 teams; identify buyer persona (team lead, exec, HR), then target their niche events/associations. Maintain light social “air cover” with scheduled content.
  • Andrew (Firefly): iOS app gives real-time, verbal form feedback via phone camera; 10K+ downloads; next focus is marketing and iteration.
    • Feedback: Free-user validation counts if you can tie it to product KPIs that indicate value (e.g., sessions/week, recorded lifts). Revenue helps but is context-sensitive; small MRR can be judged differently based on capital raised and capital efficiency.
  • Ali (Bodcare): AI-backed mental/physical health coaching for employees to lower healthcare costs and improve performance; moving B2C → B2B.
    • Feedback: Avoid “obvious” AI builds; sharpen the specific user/problem. Sell the business case (e.g., reduced claims/costs) and embed this ROI narrative in all collateral.
  • Edgy Sync AI (Founder name not captured): AI teaching system for AI fluency in schools; asks about lean team vs. traditional scaling.
    • Feedback: Product- and market-dependent; with the right CTO using AI/agents, lean teams can scale impressively; align sales org to market realities (e.g., adtech’s long cycles and face-to-face nature).
  • Addie (ShopQuick, UK): AI shopping assistant for real-time price comparison, universal scan-and-pay, AI shopping lists; freemium + B2B model; early waitlist and FMCG LOI.
    • Feedback: Consumer acquisition/retention is the make-or-break in a crowded AI shopping space; build trust and differentiation quickly.
  • Anton (Fast Query): AI chat + tasking tied to store inventory; 70 stores, ~$100K ARR, ~95% margin; solo founder.
    • Feedback: Current revenue is adequate to begin a raise.
  • Rose (Healthcare AI): Root-cause algorithm for personalized care, 100 case studies, reduces visits and costs; exploring B2B employer model.
    • Feedback: Positioning over pricing model: sell savings (e.g., -30% healthcare spend/claims). Typical construct is platform fee (low five figures) + per-employee fee; show clear ROI math.

How to Reach Christy

  • Best follow-up via LinkedIn and the firm’s website intake form (she personally receives form submissions). Expect a quick, respectful “no” when off-thesis—time is precious for founders.

Trey Icard (Wiv Ventures)

Background and Fund Focus

  • Multi-exit entrepreneur; founded first network-enabled app in 2000 (institutional data streaming to mobile for banks). Deep operator experience across startups and enterprise.
  • Motivation for Wiv: Fintech innovation outside the coasts (e.g., Texas, central U.S.) has been underserved by capital historically; sees strong regional opportunities now.
  • Investment stage: Early (pre-/at go-to-market), transaction-centric fintech; less crypto focus currently. Invests in both B2B and B2C fintech.

Life as a Fund Manager: Pros and Cons

  • Responsibility to LPs: Diligence and returns drive decision-making; portfolio selection is under scrutiny; pressure is real.
  • No crystal ball: Aim to hedge risk; even strong funds miss obvious winners in hindsight (e.g., local anecdote of a VC preferring limousines.com over Uber).

Investment Process and Guidance for Founders

  • Qualify the investor early:
    • Sector focus (e.g., fintech vs. biotech)
    • Check size fit
    • Are they actively deploying?
    • Best way to share materials
  • Referrals win: Warm intros via LPs or other VCs carry weight; the ecosystem is highly networked and collaborative.
  • Evaluation approach:
    • Start with financials: Look for coherence with the deck and basic financial stewardship
    • Growth indicators: Any measurable, repeatable growth signal (revenue, usage, conversion) that shows you can deploy capital to scale
    • Plan and execution: Clear, crisp roadmap showing stepwise progress (“we did X, then Y happened; next we’ll do Z”)
  • Regulatory diligence (fintech): Founders must be the domain experts; Wiv will dig into regulatory pathways, but expects founders to understand constraints and who the payer is.
  • Market trends: Compliance tooling; AI agents/expertise-as-a-service in finance; U.S. banking rails are antiquated (making modernization harder), with faster innovation often outside the U.S.
  • Exit expectations: Funds typically 10-year vehicles; target liquidity in 5–7 years. Founders taking VC should articulate a high-level exit path (strategic acquirers, IPO potential) even at early stages. If you don’t need VC, don’t take it—but if you do, align on exit.
  • Pitching content (1-minute): What you do, who it’s for, size of opportunity—leave the investor wanting more.

Founder Pitches: Highlights and Feedback (Session 2)

  • Monish & Parth (Social Stock Exchange): Trade “influence” (celebs, politicians, creators) like an exchange; asked about B2C distribution/liquidity.
    • Feedback: Scalability/liquidity is the core risk; partnerships with large orgs/brands to acquire users at scale may be essential; organic user-by-user growth is costly and slow.
  • Adrian Humphrey (Taylor Labs AI): End-to-end AI video editor (from raw footage to finished TikTok/YouTube content); first place in world’s largest hackathon; raising $1.5M pre-seed.
    • Feedback: Leverage event network for investor intros; ask VCs for sector-fit referrals; pitch VCs as potential customers (if they adopt, they may invest).
  • Dimitri (Couples’ co-pilot for money/life): 15K users; team from Google/Citadel; asked what VCs want now.
    • Feedback: Above all: a clear, convincing plan and the founder’s ability to answer beyond the deck; long-term vision matters (Amazon example—start with books, expand to “sell everything”). Note: Trey’s fund is fintech-focused.
  • Abhishek (Vigilant Tax): Agentic AI for blockchain smart-contract security; MVP complete, building Phase 1; asks about incorporation and angels demanding cash/equity/fees.
    • Feedback: Form a proper C-corp (Delaware standard; Texas acceptable) with a startup attorney before fundraising. Prioritize finding real users (even free) to validate necessity; if no one will use it for free, that’s a signal.
  • Dylan Boon: Transitioning from construction services to healthcare SaaS (UT Austin’s Texas FIED); concerns about founder-market fit.
    • Feedback: Early-stage is about execution and learning velocity. Demonstrate wall-breaking and delivery; deep institutional expertise can be layered as you scale into later stages.
  • Elena (18, West Africa): Building “Seamless,” an industrial tools/machinery sourcing marketplace; non-technical; asked timing for VC outreach.
    • Feedback: Start with family/friends and small checks; practice pitching; show tangible progress and revenue signals before approaching institutional VC.

Cross-Session Practical Takeaways

  • For 1-minute pitches:
    • Christy: State the problem and who it’s for—clearly.
    • Trey: Say what it is, who it serves, and the opportunity—leave room for curiosity.
  • Customer validation: Don’t hide behind dashboards; speak with customers. Use short, human feedback loops where possible.
  • Business case clarity: Tie your product to measurable outcomes (cost reductions, revenue lifts, risk mitigation) and sell to that.
  • Process transparency: It is appropriate to ask a VC about their process, timelines, decision-making, and deployment status.
  • Very early-stage investing is real but rare: Fire Road is a true inception investor; many “pre-seed” funds still seek post-revenue.
  • Team scaling in AI: With the right technical leadership and agentic automation, small teams can achieve outsized output; ensure your sales motion matches your market.
  • Fundraising and formation: Use a startup-savvy attorney; standardize cap table/governance early; be cautious with advisors who demand cash + equity before traction.
  • Exit mindset: If you opt into VC, you opt into an exit horizon—be prepared to discuss potential paths.

How to Follow Up

  • Fire Road Ventures (Christy Johnson): Connect on LinkedIn; submit via the firm’s website intake form (she reviews submissions) and expect a quick “no” when off-thesis.
  • Wiv Ventures (Trey Icard): Connect via LinkedIn; submit decks through wiv.vc (Submit a Company form).
  • Daryl’s Office Hours: Every Friday, 12–2 pm CT on X; transitioning some post-session founder programming to Chatter Social (founded by Nelson).

Closing Notes and Upcoming

  • Daryl acknowledged platform glitches during live sessions; appreciates community resilience and co-host support.
  • Upcoming guests teased: AP1 VC and Mission One Capital.
  • Cultural note: The community celebrates wins (e.g., Rose’s birthday) and fosters mutual support—a consistent theme of service and partnership over transactional interactions.