Investor Office Hours w/ Expert Dojo & Propellant Ventures

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Darrel Frater ✝️
@DarrelFraterSep 23, 2025

The Spaces brought together two investor segments to help founders navigate fundraising and sharpen their pitches. Host Daryl Freighter opened with his family office mission and the plan to launch a differentiated fund-of-funds. Ash (CEO/GP at Expert Dojo) shared his journey into VC and a founder-first thesis: small initial checks (50–100k), follow-ons up to $1M, sector/geo agnostic, and a strong emphasis on trust, relationships, and customer love—advocating for a “Maximum Lovable Product” over MVP. He outlined Expert Dojo’s one‑month decision process and Fund 3’s decentralization (celebrity-led Miami fund; India-focused fund). Founders pitched across biotech, veterans’ benefits, African fintech, credit mentoring, and an AI media venture studio; Ash offered practical guidance (angels as validation, university partnerships, on‑chain options, testimonials, community design). In Session 2, Jason (Propellant Ventures) detailed an early seed, Midwest‑focused B2B thesis, the current capital-rich yet relationship-driven landscape, and a fast but rigorous diligence/IC process (often 2–3 weeks). He advised raising earlier and for longer runway, building strong teams and focused go‑to‑market, and using service providers, events, and platforms like Lunchclub to expand networks. Additional founder pitches covered freight negotiation AI, fintech/edtech for National Guard, social impact remote work, deep‑tech troubleshooting, and voice outbound sales; Jason responded with targeted advice on employment conflicts, investor selection, readiness, and habits to reach $1M in ARR.

Good News Office Hours — Investor AMA and Founder Pitches

Session Overview

A two-part Twitter Spaces office hours led by Daryl Freighter (Founder, Freighter Family Foundation; former Visible Hands and Surack Ventures) featuring:

  • Ash (CEO & General Partner, Expert Dojo) — early-stage investor/operator perspectives, fund thesis, and tactical fundraising advice.
  • Jason (Managing Partner, Propellant Ventures) — Midwest-focused B2B investor perspectives, process transparency, and go-to-market guidance for fundraising readiness.

Format: Investor introductions and theses, deep-dive on fundraising psychology and process, followed by multiple 1-minute founder pitches with investor feedback.

Participants and Roles

  • Daryl Freighter — Host; founder of Freighter Family Foundation; building a family office in Tulsa focused on economic mobility via tech; announced intent to launch a differentiated fund-of-funds plus direct investment vehicle. Creator of the “Good News” Office Hours (mixing faith and founder support); former founder turned investor (Visible Hands, pre-seed; Surack Ventures, seed).
  • Ash (Expert Dojo) — CEO & General Partner; former operator and founder; joined Expert Dojo after fellowships and community building; oversees a global early-stage portfolio.
  • Jason (Propellant Ventures) — Managing Partner; 20+ years in entrepreneurship/investing; runs the Founder Institute Chicago chapter (170+ grads) and invests in early-seed B2B tech, primarily Midwest.
  • Kabe (“Coffee”) — Co-host assisting with speaker logistics.
  • Additional references: Brian (Founder, Expert Dojo); multiple founders who pitched.

Expert Dojo (Ash) — Thesis, Process, and Advice

Who Expert Dojo Backs and How They Operate

  • Stage/Check sizes: First checks of $50k–$100k; follow-ons up to $1M within ~3 years if growth milestones are met.
  • Scope: Sector-agnostic, geo-agnostic; founder-first orientation. Avoids capital-intensive categories for now (e.g., hardware, space; healthcare with heavy regulatory friction). Software and scalable GTM are the sweet spot.
  • Portfolio scale: 300+ investments globally to date (approx. 40 in Africa, 30+ in India, ~150–160 in the US) with intention to scale to 1,000+ portfolio companies.
  • Structure: Runs as an accelerator plus VC hybrid. “Dojo” reflects an academy of continuous learning: capital plus hands-on GTM, network access, mindset/peak-performance coaching.
  • Fund architecture (Fund 3 and beyond):
    • Celebrity-led fund (Miami) — targets consumer/creator/brand leverage where celebrities can influence distribution/awareness.
    • India-dedicated fund — first office outside the US; builds the Indo–US bridge for capital, market entry, and scale.
    • “Decentralizing” the fund: localized vehicles in multiple geographies over time.
  • LP model: Historically anchored by a single family office (billion+ AUM; never needed broad LP outreach early). Progression: Fund I ~$5M → Fund II ~$30M → Fund III ~$100M; now expanding LP base as portfolio traction compounds.

Investment Process (Ash)

  • Sourcing: 1,000+ co-investor relationships; 200+ global scouts (aspiring VCs building pipelines); inbound plus proactive analyst outreach.
  • Current deployment (timing caveat): A temporary 2–3 month pause due to internal restructuring; typical close cycles under 4 weeks when active.
  • Diligence cadence: 15-min intro → 30-min deep-dive → partner review → internal IC.
  • Post-investment enablement: Expert Dojo audits outbound/GTM, founder mindset/peak performance, “investment proficiency,” and benchmarks vs. company CAGR; builds a customized portfolio support plan; re-ups with follow-on capital based on growth.

Portfolio Highlight

  • “Credit” (spelled with a K) — portfolio company recently closed a $22M Series A; covered on NASDAQ media channels.

Fundraising and Product Advice (Ash)

  • Core principle: At early stage, “trust and relationships” drive capital. Don’t be discouraged by no’s; be optimistic and aggressive in outreach. Follow up with concise progress updates (monthly/quarterly) to build conviction over time.
  • Relationship-first fundraising: Optimize for long-term trust, not transactional speed. You can’t control timing; you can control process and persistence.
  • Customer-first building: Be problem-centric. Let customers validate the pain and love the product before courting investors. “Customers should be your first investors.”
  • MVP vs. MLP: Replace “Minimum Viable Product” with “Maximum Lovable Product.” Build with love and delight to convert early users into champions, revenue, and even investors.
  • Capital discipline: Only raise what you need; too much capital too early can hurt. Act like a unicorn founder (professionalism, consistent investor reporting, habit formation) before you are one.
  • Deck hygiene: Put critical metrics on the first slide (traction, revenue, raise, use of funds). Skip overly ornate decks; clarity > aesthetics.
  • Targeting angels vs. VCs: Angels provide easy validation and intros to VCs. In crypto/fintech, consider on-chain raises to reduce equity dilution (where appropriate). Time VC outreach right; an early misfire can poison a future yes.

1-Minute Pitch Guidance (Ash)

  • Lead with the problem and clear customer validation. Then state solution succinctly.

Founder Pitches — Session 1 (to Ash)

1) AI-driven Media/Tech Venture Studio for Personal Brands (Kabe/“Coffee”)

  • What: Full-stack media-tech venture studio for creators (coaches, authors, speakers), spanning motivational music catalog (570+ songs), course offerings, agency services (press/TV), tech arm, and a venture studio. Demonstrated small-offer funnel performance (e.g., $49 → $17k).
  • Ask: Strategic financing design — raise a large runway (e.g., $2M) vs. a focused tranche (e.g., $85k for acquisition channel)? How to approach LPs/family offices as an emerging manager vs. portfolio SPVs?
  • Feedback (Ash + Daryl):
    • Match raise size to needs and access: If $85k truly unlocks MRR, don’t over-raise. Consider a buffer (e.g., $50k more) for contingencies.
    • LP strategy: A single, aligned family office can accelerate fund formation. Expert Dojo grew with one FO LP before expanding.
    • Overarching: Access to capital often dictates viable paths; be pragmatic about what’s in reach now versus later.

2) Biotech/Medical Research Lab (Nora)

  • What: Build labs to produce high-quality oligonucleotides for research (no FDA pathway needed for raw materials). Seed raise to stand up first lab (San Diego), plus significant capex (e.g., mass spectrometer). Expansion plan to Boston and Austin. Early interest (e.g., UCSF physician discussions).
  • Ask: Would Expert Dojo skip small checks and invest at seed scale?
  • Feedback (Ash):
    • Current thesis avoids capital-intensive plays. May be a fit for future growth vehicles, not current funds.
    • Strategic path: Partner with university ecosystems (accelerators, translational funds, institutes like Broad/MIT/Harvard; Boston is prime). Leverage institutional credibility, access to scientists/researchers, and campus-linked funding.

3) Veterans’ Benefits Hub (Kerwin, Vadi.com)

  • What: Centralized discovery for veterans’ benefits, discounts, housing, education, across federal/state/city/private. Chat assistant plus matching algorithm across 68k+ opportunities (16k indexed so far). Bootstrapped; 23 early users; constrained by scraping/time/token limits.
  • Ask: How to raise properly and find aligned investors?
  • Feedback (Ash):
    • Double down on early customers: Deliver outcomes, collect testimonials, elevate them as advisors, clarify revenue model.
    • Community layer: Beyond utility, create shared-interest groups (e.g., swimming, venture) to drive engagement and organic growth.
    • Warm intros: Connect with The Veteran Fund (Mike) as a targeted capital source for veteran-aligned ventures.
    • Daryl: Shared a concise 90-page fundraising book (available to other founders via DM).

4) AI Financial Assistant in WhatsApp (Africa) (Founder: “Familiaria,” product: Floss)

  • What: AI-powered personal finance and payments in WhatsApp (stablecoins and local currency), voice commands in multiple languages/dialects, targeting financial inclusion and usability at low literacy levels. 500+ waitlist signups in ~2 weeks. Raising ~$250k angel.
  • Ask: Is now a good time to raise angel capital; how to structure it?
  • Feedback (Ash):
    • Africa + fintech remain promising; angels are strong first validation.
    • Consider on-chain fundraising to preserve equity.
    • Sequence: Start with angels, build traction, then time VC outreach carefully to avoid premature no’s.

5) Credit Mentoring Platform (Antwan, Credit Genius)

  • What: Gamified, AI-powered credit mentoring that explains score changes, guides users to 800+, upsells tradelines/funding; media features; pilot traction.
  • Ask: Levers to become category leader with 100M+ US consumers struggling with credit?
  • Feedback (Ash):
    • Distribution via credit unions, especially university-affiliated unions; seed financial literacy and behavior change pre-graduation.
    • Long-term habit formation is key; partner where behavior is shaped (schools/unions) to lock in early cohorts and validation (logos, potential capital).

6) Trading Bot for HNWIs (Alan, “Magic Money”)

  • What: Claims of superior returns and user capital control via brokerage-embedded bot; seeking UHNW client growth (not venture raise). Limited Q&A due to time; session transition.

Propellant Ventures (Jason) — Thesis, Process, and Advice

Firm Focus and Thesis

  • Geography: Primarily Midwest (good founders everywhere, but firm differentiation is early institutional capital in undercapitalized region/stages).
  • Stage: Early seed / pre-seed; often one of the first professional checks; no minimum revenue requirement (recent pre-revenue investment closed).
  • Sectors (B2B tech): Fintech, Adtech/Martech, Proptech, Logistics & Supply Chain, Future of Work, Healthtech.
  • Bandwidth & Support: Often supports companies in closing rounds and planning the next raise; provides customer/partner introductions when helpful.

Market Context and Fundraising Strategy (Jason)

  • Capital availability: More capital exists now than ever; but raise cycles are slower and diligence deeper.
  • Planning: Expect 2× the time to raise and 2–3× more capital than you initially project; target 12–18 months runway (24 if possible and capital-efficient).
  • Relationship-led access: Warm intros stand out; most Propellant deals come via trusted relationships or Jason’s network.
  • Resilience: Larger funds may be focused on supporting existing portfolios, leaving less for new deals; persistence and capital efficiency matter.
  • Angels vs. VCs: Media over-indexes VC; many succeed via angels/family offices. VCs typically want some traction, but pre-revenue is possible if team/market fit is strong.
  • Start early: Build relationships months before you need capital; send periodic progress updates to warm the funnel.

Relationship Building — Practical Tactics

  • Leverage service providers (lawyers, accountants, bankers) for intros.
  • Tap other founders (esp. those who’ve raised) for investor referrals.
  • Offline and online: Attend curated events, be selective, prioritize those with investor presence; host your own events/thought-leadership to pull capital to you.
  • Tools: Lunchclub (Jason shared an invite link; still functions despite minimal ops); LinkedIn for outreach (avoid generic spam; tailor to investor thesis).

Pitch Structure (Founder Institute Template Jason Shared)

“My company is developing a [defined offering] to help [target audience] solve [core problem] by [secret sauce/why now].”

  • Add why you/your team are uniquely suited; optional: why the timing is right.
  • Don’t lead with “AI” — it’s a means, not the value proposition. Use it later to support differentiation.

Propellant Ventures’ Investment Process (Transparency)

  • Entry: Warm intro preferred; Jason is approachable, but generic, AI-generated/spammy emails get ignored.
  • Materials: Initial deck; upon interest, provide a data room (deck, team bios, financial forecast, term sheet, research, etc. appropriate to stage).
  • Diligence: Jason compiles a question list; conducts a deep-dive call; references (lead or prior investor), and customer calls (if revenue).
  • Speed: Has closed in as little as 2–3 weeks (first call to wire), but still produces a 10–15 page diligence memo.
  • IC: Investors on an Investment Committee review materials; final Q&A with CEO; 24-hour decision typical after IC; capital wired quickly (no capital-call delays).

“Investor-Ready” Criteria (Pre-Market vs. Go-to-Market)

  • Fit to thesis (stage/geo/sector). Team is paramount: domain expertise, relevant experience, and advisor bench strength where gaps exist.
  • Traction signals: Revenue preferred but not mandatory; users/pilots/LOIs; clear KPIs; early partnerships.
  • Focus: Avoid product/revenue sprawl. Start narrow, dominate a beachhead, then expand. Lack of focus is a red flag.
  • Timing: Don’t start raising with 1–3 months of runway; begin 6–12 months ahead and articulate milestone-based use of funds.

Founder Pitches — Session 2 (to Jason)

1) Free Tackle (Sina) — Freight/Logistics Negotiation Automation

  • What: Algorithmic negotiation for freight procurement; adaptive AI + game theory; operator-built by a 10-year procurement lead + CS PhD cofounder (Gemini project contributor). Reported 7% YoY savings in live bids; “≥4% savings or no pay” guarantee. MVP built; targeting >$5M freight spend companies.
  • Ask: GTM ethics/conflicts — pitching to peers while still employed; tested internally already.
  • Feedback (Jason):
    • Avoid conflicts: Review employment contract (IP, non-compete, side work). Clarify separation from current employer.
    • Early buyer discovery: Start with prospects you don’t work with; seek confidential feedback and pilots outside current employer.
    • Potential path: If employer is supportive, they could become a design partner or investor; otherwise, spin-out later is viable (example: founder who spun out a company-owned product with transferred IP).

2) Prometheus Flex (Kat) — Fintech/Edtech for Financial Acumen (Wedge: Military)

  • What: A web-based, creator marketplace platform for financial acumen with a consumer experience described as “MySpace × SimCity × OnlyFans (model for creator monetization).” Beachhead: Army/Air National Guard in MA; broader Midwest expansion (e.g., MI, IN); TAM includes military families and young parents.
  • Ask: Cap table strategy when undecided on private vs. public path; how selective to be with early investors.
  • Feedback (Jason):
    • IPO is an outcome, not a plan; build for strong fundamentals. Most startups don’t go public.
    • Be discerning, but fundraising is hard — don’t be unrealistically picky. Investors are typically not involved in day-to-day; optimize for alignment but keep momentum.

3) Remotely Good (Teresa) — Remote, Social Impact Career Platform

  • What: AI-powered job discovery/coaching for 70M US job seekers who seek mission-driven roles; job board + AI resume/cover letter/interview tools; planned auto-apply; B2B (employer tools/listings) + B2C (job seeker tools). Metrics: ~2,000 MAU, ~150 paying users (lifetime), 15 employer LOIs.
  • Ask: Propellant’s fit with “future of work” and support offered to first-time founders.
  • Feedback (Jason): Propellant invests in future-of-work; they assess team, traction, competitive positioning; can help with capital formation and intros; encouraged direct follow-up.

4) Agentic Troubleshooting for Mechatronic Systems (Fragwell)

  • What: B2B SaaS for troubleshooting across robotics/mechatronics (mechanical/electrical/software integration), enabling cross-functional collaboration and minimizing downtime; early traction with universities/companies; founder based in UK (visa constraints, not full-time yet).
  • Ask: Fit for Propellant.
  • Feedback (Jason): Potential fit for future deep-tech focus (Fund 2), not current Fund 1 mandate.

5) Cassie.ai (Raphael) — Intelligent Outbound Voice for B2B Sales

  • What: AI-driven outbound voice to automate prospecting and pipeline creation; founder has top-performer sales track record; 100+ customer interviews; raising $500k pre-seed.
  • Ask: Top three success habits to scale from $0 to $1M ARR.
  • Feedback (Jason):
    • Nail product–market fit via systematic customer development and iteration.
    • Build a capable team (including sales beyond the founder) to scale repeatably.
    • Be resilient/adaptable; most companies pivot target segments/models on the path to fit.

Cross-Session Takeaways and Actionable Guidance

Fundraising Mindset

  • Relationships and trust are the core currency. Warm intros outperform cold outreach.
  • Be optimistic and persistent; “no” often means “not yet.” Use updates to nurture pipeline.
  • Don’t raise more than necessary; raise early enough to avoid desperation and preserve leverage.

Go-to-Market Discipline

  • Lead with a crisp problem statement and customer validation; product love drives investor love.
  • Start narrow (beachhead), achieve dominance, then expand to adjacent segments.
  • Replace MVP with MLP (Maximum Lovable Product) to anchor on customer delight and advocacy.

Materials and Process Hygiene

  • Deck: Put key numbers (traction, revenue, raise, use of funds) on slide 1.
  • Data room: Right-size to stage — deck, bios, forecast, term sheet, KPIs, research, references.
  • Reporting: Post-raise, send consistent quarterly updates; professionalism compounds trust and access.

Distribution and Partnerships

  • For fintech/credit: Credit unions (esp. university-affiliated) as channels and validators.
  • For biotech: University ecosystems (accelerators/institutes) for pilots, capital, credibility.
  • For veterans: Layer community features atop utility to drive retention and viral spread; pursue veteran-focused funds.

Capital Stack Options

  • Angels for early validation and VC intros; consider on-chain raises for web3/fintech contexts.
  • Family offices can anchor emerging funds or studios; a single aligned FO can be catalytic.

Resources and Follow-ups

  • Ash (Expert Dojo): LinkedIn link was pinned during the session; also running a 21-day growth hacking challenge on LinkedIn.
  • Jason (Propellant Ventures): Shared a Lunchclub invite link; prefers tailored LinkedIn outreach referencing this session.
  • Daryl: Offering a concise PDF fundraising book by DM for attendees.

Program Notes and Announcements

  • Daryl’s announcement: Preparing to launch a unique fund (fund-of-funds + direct investments); updates forthcoming as progress is made.
  • Good News Office Hours origin: Launched ~2.5 years ago when Daryl’s daughter Gianna was born; designed as low-pressure investor–founder dialogues.
  • Scheduling: No Office Hours next week due to Tulsa Tech Week (Daryl hosting “Feature Day” on Tuesday). Sessions resume in two weeks.