Investor Office Hours w/ Calumet Investments & AHA Ventures

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Darrel Frater ✝️
@DarrelFraterNov 18, 2025

The Spaces brought founders into a live, simulcast office hours with host Daryl Freighter and two non-traditional investors: family office/angel investor Ben Wiggins and Mark from the American Heart Association’s venture arm. Ben outlined how family offices often operate sector-agnostic mandates with a strong founder-quality focus, his bias for post-revenue or prior-exit teams, and why advisory relationships often precede his checks. He emphasized continual selling, learning, and fundraising; how to build investor relationships by engaging their public content; and what to prioritize in a one-minute pitch (traction, team, market, unit economics). Founders pitched products ranging from AI-generated proposal documents and community insights to home healthcare marketplaces, sports video highlights, fintech for African remote workers, and a urine-based malaria test, receiving targeted feedback on GTM, valuation, distribution, licensing, and team composition. Mark detailed AHA’s impact-first corporate VC with funds spanning social determinants of health, med devices/therapeutics, women’s health, and a studio, and how AHA adds value via research validation and evidence generation. The session closed with practical guidance on focus (narrow product/market first), regulatory strategy, proving demand pre-license, and continuing relationship-driven follow-ups on LinkedIn.

Good News Office Hours: Family Office + Corporate VC Insights and Founder Pitches

Session Overview

  • Host: Daryl Freighter (VC, former founder; runs weekly investor office hours). Simulcast on X (Twitter Spaces) and Chatter Social (with video). Co-host support from Leah (Chatter team).
  • Format:
    • Investor intros and operating theses
    • Practical fundraising and relationship-building advice
    • One-minute founder pitches followed by a focused question to the guest investor
  • Guests:
    • Ben Wiggins (Chief Investment Officer at a family office; active angel; runs a 400-founder community and screening process dubbed “Founders Group”)
    • Mark [American Heart Association (AHA) Ventures] (impact-focused corporate VC; prior family office and development finance experience)

Key Themes and Takeaways (High-Level)

  • Always-on motion: Founders should be simultaneously improving product, selling, fundraising, and learning—continuously.
  • Traction is broader than revenue: Pre-revenue traction can include LOIs, pilots, waitlists, deposits, partnership MoUs, user growth/retention, and evidence of value.
  • Relationship-first fundraising: Warm intros and consistent engagement with investors’ content build familiarity and trust before the ask.
  • One-minute pitch priorities: Traction, team (exits or brand logos), market, unit economics. Get into (and out of) the problem statement quickly.
  • Valuation is more art than science: Revenue/growth/profitability and founder track record matter; momentum and comps influence what the market will pay.
  • Corporate VC (AHA) is impact- and strategy-led: Alignment with mission, ability to generate health outcomes (esp. cardiovascular and stroke-related), and the capacity to validate scientifically are crucial.

Guest 1: Ben Wiggins (Family Office CIO & Angel)

Background & Role

  • ~20 years in startups; 7x founder with a first exit in 2024. Hired by a family office ~10 years ago to build a quant model; now CIO. Active angel investor.
  • Community builder: runs a 400-founder Discord (Founders Group) and uses an internal AI-based readiness screener (“Ben AI”).

Family Office & Angel Thesis

  • Sector-agnostic on the private side; heavily founder-centric.
  • Preference: post-revenue. Pre-revenue investments are largely limited to founders with prior exits.
  • Founder traits: curious, coachable, committed. Avoids founders who “manufacture FOMO.”
  • Advisory-first: More likely to invest if first engaged as an advisor (investor relations, fundraising, strategy, culture, recruiting/retention, exit planning). Advisory helps him learn unfamiliar sectors.
  • Sector lanes avoided: fine arts (film/TV/theater/music) as an investor (loves them as a person), limited appetite for med devices and food & beverage. Games are an exception—can be commerce-first.

Operating Advice for Founders

  • Four parallel tracks at all times:
    1. Always be improving product and UX
    2. Always be selling and doing discovery
    3. Always be fundraising (line up meetings; momentum matters)
    4. Always be learning
  • Balance is difficult but critical. Quiet, relentless execution communicates inevitability more than hype.

Building Investor Relationships

  • Best: warm intro from another investor already committing or engaged.
  • Cold approach playbook:
    • Engage consistently with the investor’s content (like/comment/repost) to become a familiar name.
    • Smaller-audience, public-facing investors are more reachable via content engagement than celebrity VCs.
  • Network effects: When Ben believes in a founder, he proactively connects them across networks (example: shepherded a founder into Aggie Angel Network pitch the same day).

One-Minute Pitch: What to Prioritize

  • Traction first (if revenue: revenue/run-rate, growth, profitability; if pre-revenue: LOIs, deposits, pilots, waitlists, partnerships, customer research metrics, social proof—all quantified).
  • Team second (prior exits, major brand associations—Fortune 100/500 experiences or partnerships).
  • Market third (size and clarity of the opportunity).
  • Unit economics (as available) to show business model sanity.

Valuation Guidance (Pre-Seed/Seed)

  • Inputs: revenue, growth, profitability, prior exits; adjusted by market comps and investor gut.
  • Reality: If the company is exceptional, a “high” valuation may still clear; investors decide if they believe you’ll “get there.”
  • Practical tip: Cluster pitch meetings to create momentum; avoid relying on artificial FOMO.

Founder Pitches to Ben (Summarized)

Paul — “Hisbook” (Real-time History Curation)

  • Concept: AI + blockchain-based platform to curate and time-stamp events in real time, hashing sources for integrity. 1,000+ expressions of interest; UI/UX done; building product; exited prior startup.
  • Initial misstep: Opened with a direct investment/advisory ask.
  • Host coaching (Daryl): Don’t lead with an ask; first ask a problem-focused question to add value and build rapport.
  • Refined question: Legal issues accessing/scraping top media content.
  • Ben’s advice:
    • Lean into community building for data access—relationships with content owners often outperform scraping.
    • Clarify and simplify “why blockchain”: Investors need a crisp, non-technical justification for blockchain’s necessity vs. alternatives.
    • Follow up on LinkedIn for deeper guidance.

Lilia — AI for Infrastructure Tendering & Proposal Gen

  • Product: AI platform that surfaces/qualifies infrastructure opportunities across multiple tender sites and generates full, complex proposal documents (hundreds of pages) in one click.
  • Traction: 4 pilots, including a major construction firm with >$250M/year in projects. Team: ex-associate partner with extensive complex doc experience + ML engineer co-founder.
  • Question: Creative GTM in infra beyond LinkedIn/conferences.
  • Ben’s advice: Build content for both Tier-1 buyers and their customers (Tier-2). Authentic storytelling around customer outcomes attracts both. Consider specialist GTM partners (e.g., Sellerance).

Daniel — Swirl (Community Insights Platform)

  • Thesis: Replace scraping/surveys with conversation. Brand-specific conversational AI agents join meetups to build trust and generate decision-grade insight.
  • Traction: 15 brands (e.g., Chase, Omnicom, a major wireless carrier); $1.7M revenue in first year; doubled revenue for 3 consecutive months. Raising $1M seed.
  • Question: Setting valuation caps at early stage.
  • Ben’s view: It’s more art than science—revenue/growth/profitability/prior exits plus comps and investor gut. Momentum matters; line up meetings.
  • Host adds: Narrative and comps must align with the ask; price is what enough investors will pay.

Amit (“Manny”) — Ventable (Venture Operating System)

  • Product: Multi-user platform for founders/investors/accelerators/studios/family offices. “Fundability score” to educate founders and streamline diligence for VCs.
  • Traction: ~75 startups onboarded; 16 venture clients deploying capital on-platform; $1K MRR; integrations underway; onboarding 5 large accelerators.
  • Question: Using AI for diligence to reduce bias.
  • Ben: Uses proprietary “Ben AI” within Founders Group to assess readiness (problem/solution, market sizing, competition, traction, timing, team, ask/offer, use of funds, exit). Not public yet; training to improve scoring.
  • Ben’s caution: Investor adoption is fragile—first poor-fit deals can sour perception. Long-term aim is to monetize VCs (who have budget), but distribution and curation quality are critical.

Pavel — Nolan Rights Entertainment (Political Strategy Games)

  • Thesis: Channel global political frustrations into mass-market games with validated genres. Current: mobile strategy title enabling collective control of regimes.
  • Round: Oversubscribed from $1M to $1.5M; 4 US VCs; $110K co-invested by players; alpha retention improved ~3% → ~11%.
  • Question: Why are games treated differently? Within thesis?
  • Ben: Games can be “commerce-first” unlike other arts. Within his personal thesis (potentially), unlikely for the family office. Follow up off-call.

Guest 2: Mark (American Heart Association Ventures)

Background & Lens

  • Prior roles in asset management (ADM, Deutsche Bank), transitioned to impact-driven family office and development finance (notably East Africa, LatAm, SE Asia). Angel investor as well.
  • At AHA Ventures: deploys balance-sheet capital strategically to advance AHA’s mission (impact-first orientation).

AHA Ventures Thesis & Structure

  • Mission: Longer, healthier lives by reducing cardiovascular and stroke risk; AHA is the largest funder of research in this space.
  • Gap AHA Ventures addresses: Translating research and mission-aligned innovation into scaled, real-world solutions.
  • Vehicles:
    • Social Determinants of Health (SDOH) fund (upstream factors: diet, income, education, housing, neighborhood, etc.)
    • Medical Devices & Therapeutics fund
    • Women’s Health fund
    • Venture Studio (incubates teams to commercialize research)
  • Stage: Early (approx. Seed to Series B). Impact-first with a spectrum of returns expectations across funds.
  • Strategic-first lens: Does the deal advance AHA mission and reach target populations? Then, do the unit economics and market path make sense?

Value-Add & Sourcing

  • Value-add levers:
    • Scientific validation: internal science, data science, and research teams; ability to design/run RCTs/effectiveness studies; strengthen evidence for outcomes and payer/provider adoption.
    • Brand reach and national footprint: AHA offices across US; broad professional networks.
  • Sourcing: Relationship-heavy; inbound welcomed via LinkedIn; regional AHA presence aids deal flow.

What to Emphasize in a One-Minute Pitch to AHA

  • Team and founder story (why you, why this problem). Passion matters, especially in tough markets (e.g., Medicaid).
  • Problem → solution clarity; earliest traction (even pre-revenue usage, reach, retention).
  • Evidence or plausibility that use leads to target health outcomes (direct or indirect).

Founder Pitches to Mark (Summarized)

Daniel — “MC” (Programmable Live Event Engine for Creators)

  • Problem: Creators hack together multiple tools for “shows” (battles, trivia, talk shows) without unified infrastructure.
  • Product: Event engine to design segments/timers/logic, integrate social platforms, and reduce audience-splitting.
  • Question: What does “traction” mean to you, especially pre-revenue?
  • Mark: Usage breadth/depth (active users, retention, distribution), and—critically for AHA—evidence that usage drives relevant health or social outcomes. Revenue is not the only traction signal.

Dallas — Doctrinu (Home Healthcare Marketplace)

  • Problem: Agencies take 40–60% commission from nurses; compliance and verification are repeatable and automatable.
  • Product: HIPAA-compliant marketplace; pre-auth, primary source verification; reduce take-rate to ~5%; compliant in all 50 states (marketplace model, not an agency).
  • Question: Market appetite; biggest roadblocks?
  • Mark: Crowded space; the hardest problem is distribution. How will you systematically acquire both sides (patients/providers) and defend against incumbent replication?

Frank — Ballers (Amateur Basketball Highlights via AI)

  • Product: AI transforms pickup game footage into highlights; community building across cities. First league onboarded; ~400-person communities; strong technical team (ex-Microsoft, HuddI).
  • Question: AHA levers to accelerate portfolio companies.
  • Mark: Scientific validation and outcomes studies via AHA’s research capabilities (e.g., demonstrating increased physical activity and health outcomes). Strong brand and network can amplify.

Jeremiah (Jerry) — MUKE (AI Yield Protocol on Bitcoin L1)

  • Product: Non-custodial, AI-optimized liquidity pooling on Bitcoin L1 (BRC 2.0), assessing depth/slippage/risk; institutional tokenization partnerships.
  • Question: How investors view non-technical founders building technical products.
  • Mark: Many investors view lack of a technical cofounder as a red flag; it’s not always disqualifying, but you must clearly demonstrate how you’ll fill the technical leadership gap and avoid burning capital on third parties.

Aaron — BRB (Neobank for African Remote Workers)

  • Positioning: Compliance-first niche bank for remote workers from Africa operating in US/Canada; license requirements block MVP launch; partner hurdles.
  • Question: How to proceed when investors want an MVP but licenses are required first.
  • Mark: Two paths—(1) angels/friends & family to fund licensing, or (2) build the absolute leanest MVP to unlock licensure. Daryl adds: Derisk for investors by quantifying demand (waitlists, letters, pilot commitments) and showing everything else is ready pending license.

Eddie — Rapid Malaria Urine Test

  • Product: Simple urine-based malaria test (non-blood), registered in multiple African markets; >600,000 units deployed. Working on cost structure and mass-market pricing; exploring traveler market (US/EU) as a premium channel.
  • Question: US/EU go-to-market via travelers.
  • Mark: If regulatory pathway clears, US traveler DTC could provide attractive margins; worth pursuing.

Emanuel — African Vendor-to-Diaspora Export Marketplace

  • Product: Marketplace to connect African vendors (foodstuffs/consumer goods) with global buyers—reduce compliance/payment/logistics friction; ~10,000 vendors signed up; early sales via personal networks.
  • Question: What do investors expect in “goods and communication” at early stage?
  • Mark: Investors must understand fundamentals clearly—are you a software marketplace, a logistics operator, or both? Expect a methodical diligence process; clarify operating model and unit economics. Follow up with details via LinkedIn.

Olu — Multi-Product Financial Marketplace (Insurance, Stocks, Loans)

  • Thesis: Competitive to large neobanks but differentiated by multi-product breadth and focus on multi-ethnic/global diaspora segments.
  • Question: At pre-seed, launch multiple products across markets or focus?
  • Mark: Start lean—focus on one product and a specific market segment to establish distribution and quality. Acknowledge incumbents explicitly, then sharpen differentiation. Scale breadth later.

Logistics, Tools, and Community Notes

  • Simulcast on Chatter Social (video) + X. Co-host Leah pinned links; some technical hiccups (audio and app crashes) but sessions proceeded smoothly.
  • Ben departed a few minutes early to support a founder pitching Aggie Angel Network.
  • Daryl is building MeetAnyone.co to democratize access to investors and professionals with aligned incentives.

Actionable Playbook (Consolidated)

  • Relationship building:
    • Seek warm intros; if cold, consistently engage investor content to build familiarity.
    • Treat investors as long-term partners, not short-term transactions; value-first outreach.
  • Pitch construction (60 seconds):
    • Traction (revenue or pre-revenue equivalents with numbers); Team (exits, brand logos); Market; Unit economics. Move past problem statement quickly.
  • Traction without revenue:
    • LOIs, paid pilots, pre-orders/deposits, partnerships, user metrics (DAU/WAU/retention), community growth, customer discovery stats.
  • Fundraising cadence:
    • Keep a rolling process; cluster meetings; build authentic momentum; avoid artificial FOMO.
  • Corporate VC alignment (AHA-specific):
    • Make a clear line from your product to cardiovascular/stroke outcome improvements (direct or via SDOH). Be open to validation (RCTs, evidence generation).
  • Team composition:
    • For technical products, recruit technical leadership early; if not in place, show a credible plan to fill the gap.
  • Focus vs. breadth:
    • At pre-seed, narrow scope (one product, one market) to achieve real distribution and quality; expand later.

Contact & Follow-Up

  • Ben Wiggins: LinkedIn (search “Benjamin Wiggins” or “Ben Wiggins Investor”); open to connections; invites founders to Founders Group screening; often begins as advisor.
  • Mark (AHA Ventures): LinkedIn preferred; open to connections and DMs; uses LinkedIn to manage inbound and start conversations. AHA Ventures operates multiple mission-aligned funds and a venture studio.
  • Host: Daryl Freighter (continues weekly office hours; encourages founders to join via Chatter Social for video pitches; building MeetAnyone.co to streamline warm access to investors and ecosystem professionals).