Investor Office Hours w/ Stage 2 Capital & Evolution VC Partners

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Darrel Frater ✝️
@DarrelFraterAug 9, 2025

The Spaces featured two investor office hours sessions. In Session 1, host Daryl Freighter welcomed partner/investor Sakib Dadi (Stage 2 Capital). Sakib detailed Stage 2’s distinctive LP base—nearly 1,000 senior GTM leaders from top SaaS companies—who actively support portfolio companies on sales hiring, GTM design, and customer intros. He outlined typical seed expectations (product in market, design partners, early revenue often < $500k–$1M ARR) and a relationship-first approach (meeting founders up to a year before investing). Sourcing is roughly 50/50 inbound/outbound; tailored cold emails still work when relevant. He emphasized founder grit and mission as critical differentiators and advised concise elevator pitches on product, market, ICP, and “why you.” Founders pitched across marketplaces, mental health diagnostics, AI video editing, smart contract security, AI DD tools, and digital pathology; feedback focused on differentiation, investor targeting, and process. Session 2 featured Robert (Evolution VC Partners), sharing a thesis favoring “crazy” moonshots (quality of life, longevity, divinity), with examples like OpenAI, Figure AI, and Colossal. He urged founders to match with the right investor type (angels, family offices, strategics vs. traditional VC) and to make short pitches about traction, team, and product. He also introduced WeRaise, a platform that matches founders to relevant investors and scales outreach.

Investor Office Hours on X: Full Recap and Structured Notes

Participants and Roles

  • Daryl Freighter (Host): Co-founder, Freighter Family Foundation; runs weekly investor office hours and partners with Adam’s Startup Community on X.
  • Sakib Dadi (Guest Investor, Session 1): Partner, Stage 2 Capital (enterprise software seed/Series A investor).
  • Robert (Guest Investor, Session 2): Evolution VC Partners (300+ investments; “culture tech” focus); angel in moonshots (e.g., OpenAI, Figure AI, Colossal); founder of WeRaise.
  • Founders who pitched or engaged: Ben (HigherDevs), Tom (mental health diagnostics), Adrian (autonomous AI video editor), Yaz (AI-native security for authentic IDs), Phil (AI digital pathology), Abishek (smart contract security AI), Rohit (CypForensic technical due diligence), Daniel (trust-building “world peace” media/game), Cove (Wave Ventures Inc., personal brand studio).

High-Level Highlights

  • Stage 2 Capital’s true differentiation: 972 operator-LPs (CROs/VPs of Sales/GTM leaders from Datadog, Atlassian, MongoDB, ServiceTitan, Toast, Procore, HubSpot, Workday, etc.) who actively support portfolio companies in go-to-market (GTM) scaling. They are engaged pre- and post-investment for diligence, mentorship, and key hires.
  • Stage 2 invests primarily at Seed and Series A in enterprise software (app horizontal, vertical, and infrastructure). Typical checks: $2–4M. Geography: US-wide and international (international often with a local co-investing partner).
  • Fundraising access: tailored cold emails still work; “bad cold email is dead.” Warm intros help, but high-quality cold outreach can outperform.
  • Relationship-building: Stage 2 prefers to meet founders ~1 year before they’re investment-ready to build alignment for a 10–15 year journey.
  • Stage expectations (enterprise SaaS): Pre-seed = founder/team and narrative; Seed = early traction/design partners, often sub-$500k–$1M ARR; Series A = product-market fit rigor (customer references, data); Series B = GTM repeatability/efficiency.
  • What stands out in founders: Grit above all; mission-driven persistence and industry-changing intent.
  • Robert’s thesis lens: Bias to “crazy” moonshots aligned with three human arc goals (quality of life, longevity, divinity/creating new life) per Homo Deus. Emphasizes matching founders to the right investor archetype in a massively diversified capital market (VCs, family offices, angels, corporates).
  • WeRaise (Robert): Investor-matching and automated outreach platform (275k+ investors tracked). Reported outcomes: 2k+ interested-investor connections/month; ~$45M commitments in last 90 days for users.

Session 1: Stage 2 Capital with Sakib Dadi

What Stage 2 Capital Does Differently

  • LP base includes 972 individual operator-LPs (CROs/VPs of Sales and GTM leaders from top-tier enterprise software companies) in addition to institutional LPs (endowments, foundations, family offices).
  • These GTM operators actively support portfolio companies in:
    • Transition from founder-led sales to the first GTM hires (sales, marketing, CS, RevOps).
    • Diligence (market/ICP fit, sales motion viability) alongside Stage 2 pre-investment.
    • Mentorship and targeted advisory (e.g., reviewing JDs, interviewing GTM leaders, recommending independent board members).
    • Sourcing (LPs flag tools they use/love, leading to net-new opportunities).

Sourcing and Thesis Development

  • Sourcing split roughly 50/50 across inbound and outbound:
    • Inbound: LP referrals; other investors (angels/pre-seed, Series A/B) passing earlier-stage opportunities.
    • Outbound: Thematic mapping and proactive founder outreach. Example: “Next-gen ERP,” with a view that vertical winners will emerge; Stage 2 hunts down founders in target verticals for tailored engagement.

Geography

  • Invests across the US; also invests internationally. For non-US deals, Stage 2 prefers a local partner (ecosystem/context matters).

Round Size and Milestones (Typical in Today’s Market)

  • Seed rounds often total $3–5M; companies typically have product in market, early revenue/design partners; ARR usually below $500k–$1M.
  • Stage 2 invests Seed and Series A with $2–4M checks.

Process, Timing, and Relationship-Building

  • Prefers to meet founders 6–12 months before an investment so both sides can validate working relationship/values alignment for a decade-plus partnership.
  • Skeptical of ultra-compressed two-week processes for 15-year partnerships; favors prior context and mutual diligence.

What to Include in a 60-Second Pitch

  • What the product does.
  • Market opportunity (who most values it; initial ICP).
  • Why you (founder-market fit, unique insight).

What Stage 2 Looks For in Founders

  • Grit and mission orientation—clear “why” that sustains through adversity.
  • Illustrative example: Procore’s long, non-linear journey before its mid-2010s inflection (mission-led perseverance eventually matched market timing).

Cold vs. Warm Outreach

  • Warm intros tend to have higher response rates but are not required.
  • Cold outreach works when it’s specific, non-generic, and tailored to the investor’s thesis and past deals.

Founder Pitches and Feedback

  • Ben (HigherDevs; AI-driven developer-client matching; co-founder with 20-year ex-AWS leader, blockchain/tokenomics co-founder; Denver):

    • Feedback: Clearly articulate differentiation vs. incumbents (staffing/Upwork-type marketplaces). What unique market insight do you have? Why now (tech or market shift)? Spell out “why HigherDevs” vs. alternatives.

  • Tom (“23andMe for mental health”; pre-seed, small revenues; clinician tools already in market):

    • Question: Balance time across pre-seed vs. seed investors?
    • Advice (Sakib): If you’re entering a pre-seed process, focus on pre-seed investors and closing; fundraising is time-consuming. After closing, allocate time to build relationships with downstream investors.
    • Add (Daryl): Keep later-stage investors warm with low-touch updates (e.g., monthly emails) if you meet them casually; preserves time while building long-term familiarity.

  • Adrian (autonomous AI video editor; multi-agent AI; hackathon winner; early customers):

    • Question: What traction matters at pre-seed?
    • Advice (Sakib): You’re ahead of typical pre-seed with any traction; emphasize differentiation vs. AI video editors, not just raw traction. Stage view: Pre-seed = team+vision; Seed = some early traction; Series A = PMF diligence; Series B = GTM repeatability. (Daryl) Craft a compelling narrative tying today’s traction to tomorrow’s scale.

  • Yaz (AI-native security for authentic IDs; raising $3M pre-seed; 16, relocating from Turkey to US):

    • Clarification: Stage 2 typically does not invest at pre-seed; core focus is Seed/Series A; $2–4M checks; enterprise software only.

  • Phil (AI digital pathology expansion from semiconductor tech; raising $500k–$1M; market to $1.8B by 2030):

    • Guidance (format): Aim to ask a targeted question that helps you work through a tangible problem (vs. “Are we a fit?”). Connection issues prevented deeper feedback.

  • Abishek (AI co-pilot for smart contract security; detects/simulates exploits; “beyond static tools/LLMs”):

    • Advice (Sakib): Sharpen differentiation: why your approach beats static tools and why LLMs aren’t sufficient on these attack vectors. Given deep infra/security focus, target specialized crypto/security investors; infra pitches are harder for generalists.

  • Rohit (CypForensic; AI-driven technical due diligence for investors; 30s URL-based scans; 1 active customer):

    • Robert (as potential customer): Open to reviewing—DM and share access; technical diligence is a real investor pain point.

Practical Fundraising Tips Echoed in Session 1

  • Cold outbound is a skill that translates to sales and fundraising—worth mastering.
  • Think partnership and alignment; budget time for relationship-building alongside building the company.

Session 2: Evolution VC Partners with Robert

Robert’s Background and Focus

  • Evolution VC Partners: ~300 investments from pre-seed to late stage (Series E), oriented to “culture tech” (everyday consumer-interacting technology); ~41 unicorns to date (exits still pending for some).
  • Angel investments in moonshots (e.g., OpenAI; Figure AI—humanoids with uploadable skills; Colossal—de-extinction; others).
  • Founder of WeRaise (weraiseco.io): Automatically identifies right-fit investors and automates outreach; ~275k investors tracked. Reported: ~27+ interested investor connects/day, ~2,000/month; ~$45M commitments in last 90 days for users.

Investment Lens: Bias Toward “Crazy” Moonshots

  • Frames against Homo Deus themes:
    1. Quality of life
    2. Longevity (near-immortality)
    3. Divinity (creating life)
  • Observation: “Boring/safe” early-stage bets often limit upside. Moonshots are just as likely to fail but can keep attracting funding through downturns due to societal pull for them to exist.
  • Venture market has exploded (thousands of funds, hundreds of thousands of private investors, plus corporates/FOs/angels). Success depends on matching with the right investor—not one-size-fits-all pitch.

Fund Mechanics and “18” Numerology

  • Checks often expressed as multiples of 18 (from Jewish numerology, “chai” = life); can buy share counts in multiples of 18 if precise check size is incompatible with round math.

60-Second Pitch Goal and Structure

  • Goal is a meeting, not a check.
  • Three validators to emphasize: traction, team, product (1–3 of these, depending on stage and strength).

Founder Pitches and Feedback (Session 2)

  • Daniel (trust-building conversation “game” and media aimed at world peace; 6,000 hours research across 30 countries; seeking four $1M future commitments):

    • Robert: Positive on mission/ambition; asked why the $1M block size and limit of four investors (connection dropped before response).

  • Dr. Ari (Celestial Intellect Cybernetics; neurosymbolic AGI; goal: automate data science; few-shot generalization; universal induction; aims for energy-efficient, scalable AGI; long-term AGI chip; raise $12M):

    • Question: Future of superintelligence products in market?
    • Feedback: Avoid framing as “OpenAI competitor;” market now expects verticalized value propositions atop horizontal AI. Clarify the specific customer service and outcomes (e.g., “intellectual labor automation” for data science). If truly foundational AGI, communicate customer value while explaining how your approach (neurosymbolic, heterogeneous compute path) overcomes LLM limitations.

  • Cove (Wave Ventures Inc.; personal brand studio/portfolio: motivational music as top-of-funnel, courses, DFY agency, media/PR/speaking placement, D2C content OS and education platform; team assembled; needs ~$175k for acquisition/CMO ramp; longer-term “personal brand portfolio” asset class thesis):

    • Question: Pitch the full studio vs. one component first?
    • Feedback: Likely a better fit for angels/family offices/corporate media strategics than traditional VC; align investors with cashflow orientation and flexible structures. Pitch the broader vision, but lead with a clear beachhead (first wedge to scale) and show how components reinforce each other over time.

Practical Guidance from Robert

  • Don’t force-fit into a “traditional VC” mold. Map your investor targets by fit (angels, family offices, corporates/strategics, specialized funds) and pitch structure accordingly.
  • For highly technical/AI-first companies: articulate the customer value proposition without relying on the word “AI;” it should stand as a compelling business even if the AI layer is implied.

Operational Notes and Community Items

  • Ongoing partnership with Adam’s Startup Community (148k+ entrepreneurs) for distribution; sponsorship opportunities available (including creative formats, e.g., birthday shoutouts for founders).
  • Twitter Spaces had request/speaker bugs; co-hosting used to mitigate.
  • Next week’s office hours: Phil (Sovereign’s Capital) and Andrew (launching a new fund).

Actionable Takeaways for Founders

  • Differentiate clearly: Why you, why now, why this approach vs. incumbents and horizontal platforms? Highlight unique insight and durable advantage.
  • Tailored cold outreach works: Reference investor-relevant theses and portfolio; avoid generic, AI-written tone.
  • Build early relationships: Start ~6–12 months before you plan to raise from a given firm. Treat investors as long-term partners.
  • Target by stage and investor type: When in-market for pre-seed, prioritize pre-seed investors; keep later-stage warm with low-touch updates. For non-VC-fit models (media/cashflow-heavy), lean into angels/family offices/corporates.
  • Stage-appropriate storytelling: Pre-seed = team/insight; Seed = early traction and customer proof; Series A = rigorous PMF evidence; Series B = GTM efficiency and repeatability.
  • Grit and mission matter: Investors consistently value demonstrated perseverance tied to a clear “why.”
  • For infrastructure/security/web3: Expect to target specialist investors; generalists often need more tangible customer value signals.
  • 60-second pitch structure: Product, market/ICP, why you. Remember the goal is to secure a meeting.

Quick Reference: Investor Preferences

  • Stage 2 Capital (Sakib Dadi):

    • Focus: Enterprise software (horizontal apps, vertical SaaS, infra).
    • Stage: Seed and Series A.
    • Checks: $2–4M.
    • Edge: 972 operator-LPs (GTM leaders) engaged pre/post investment.
    • Geography: US and select international (with local partners).
    • Sourcing: ~50/50 inbound/outbound; thematic (e.g., next-gen ERP).

  • Evolution VC Partners / Robert:

    • Orientation: “Crazy” moonshots; culture tech; matches founders to best-fit capital archetypes.
    • Also founder of WeRaise (investor-matching and outreach automation).
    • Pitch guidance: lead with traction/team/product; tailor investor targeting; state the beachhead within the larger vision.