The Twenty Minute VCMac the VC on the Journey from Homeless To Becoming A VC | Full Interview with Harry Stebbings
CHAPTERS
- 0:00 – 1:27
Breaking into venture the unconventional way (no degree, no finance background)
Mac explains his path from software engineer and two-time founder to landing a role with the Investment Arm for the State of Maryland. He emphasizes how unlikely the transition looked on paper—and how he leaned on startup/community knowledge instead.
- •Background as a government contractor software engineer and founder
- •Second startup failed, leading to a transitional job at a marketing firm
- •Quit without a plan, then applied to Maryland’s investment arm
- •Got hired after a multi-month process despite nontraditional credentials
- 1:27 – 3:46
Burnout, public failure, and the emotional aftermath of shutting down a startup
Mac describes how he handled startup failure: returning remaining capital, withdrawing socially, and experiencing depression. He shares how friends and family helped him realize his worth wasn’t tied to a single venture outcome.
- •Burnout and shutting the company down in a very public way
- •Six months of isolation and depression to avoid questions and judgment
- •Realizing unconditional support from loved ones
- •Separating personal identity from professional outcomes
- 3:46 – 5:40
Why founders open up: trust, vulnerability, and “we’re people” investing
Mac explains why founders feel they can be more honest with him than with other investors. His founder experience and willingness to discuss hard personal topics builds deeper relationships and reduces the loneliness of being a CEO.
- •Founder empathy: remembering how lonely and difficult leadership can be
- •Creating a “call me for anything” relationship
- •Being comfortable discussing personal and professional struggles
- •Recognizing vulnerability when navigating unfamiliar ecosystems
- 5:40 – 9:20
The catalyst for RareBreed: ethics, Philando Castile, George Floyd, and a first SPV
Mac ties key career inflection points to major events affecting Black Americans, starting with Philando Castile and later George Floyd. He recounts building an SPV to back an overlooked founder, which became the spark that turned into fund formation.
- •Quit marketing job after ethical conflict linked to NRA outreach
- •Philando Castile’s killing as a personal turning point in 2016
- •George Floyd’s killing coinciding with increased Twitter presence
- •SPV formed to back a Texas-based Latin founder others overlooked
- 9:20 – 10:24
Raising a fund through Twitter: DMs, GP-to-GP backing, and 1,100 meetings
Mac explains how Twitter became a fundraising engine: DM’ing VCs who followed him, learning the mechanics, and discovering that many GPs would invest in other GPs. The pace was extreme—over a thousand meetings in a few months—leading to early soft circles and the confidence to go full time.
- •DM strategy: turning new followers into meetings to learn fundraising
- •High response rate because VCs are always seeking deal flow
- •Early believers and helpers (e.g., other GPs who reviewed deck/strategy)
- •1,100+ meetings (June–Sept 2020) to soft-circle initial capital
- 10:24 – 13:06
“Fuck the rules”: redesigning fund norms (closes, capital calls, GP commit, legal costs)
Mac argues venture has too many outdated conventions and describes how he broke them—small first close, rolling closes, flexible capital contribution options, and even starting without a GP commit. He also shares the unusual story of a lawyer who found him on Twitter and worked without billing.
- •Rejecting standard advice on first-close size and number of closes
- •Rolling closes every few weeks to deploy and build momentum
- •LP contribution options (upfront vs. multi-year) to reduce friction
- •No GP commit at the start due to lack of personal capital
- •Legal support came via Twitter; counsel effectively deferred fees
- 13:06 – 15:09
What’s broken in venture: hot deals, signaling, and why LP logic can be misguided
Mac critiques the obsession with brand-name cap tables and “hot deals,” arguing they are often confused with good, capital-returning deals. He challenges advice that emerging managers must rely on top-tier firms for access, and questions why LPs overweight signaling.
- •Distinguishing “hot” from “good” deals based on returns
- •Criticism of the idea that only top-tier funds see quality
- •Concerns about LPs using brand association as a shortcut
- •Focus on pre-seed skill: first-check investing requires strong judgment
- 15:09 – 18:07
Diversity talk vs. power: institutional LP silence and structural barriers for emerging managers
Mac shifts the diversity conversation upstream, arguing institutional LPs largely avoided public commitments and are central to real change. He explains why many institutions can’t write small enough checks for micro-funds and calls for more allocator creativity and dedicated emerging-manager programs.
- •Institutional LPs largely absent from post-2020 public commitments
- •Power dynamics: diversity change must start at the top of the stack
- •Check-size mismatch prevents many institutions from backing micro-funds
- •Need for fund-of-funds or smaller-check programs for emerging managers
- •Examples of initiatives that made a difference (e.g., smaller-check efforts)
- 18:07 – 19:39
Avoiding “diversity for diversity’s sake”: token roles and undervalued diverse associates
Mac cautions against superficial diversity efforts that add diverse junior hires without empowering them. He shares examples where diverse associates sourced strong deals but weren’t credited or supported internally, raising questions about value and fairness.
- •Tokenism risk: diversity optics without real authority or respect
- •Diverse associates facing higher standards and extra hoops
- •Disconnect between sourced deal quality and internal recognition
- •Using performance and outcomes to evaluate contribution fairly
- 19:39 – 22:38
RareBreed Fund I strategy: pre-seed check sizes, portfolio construction, and overlooked geographies
Mac outlines RareBreed’s investment approach: larger pre-seed checks with a portfolio sized for meaningful outcomes, plus selective follow-ons and limited off-thesis opportunities. He emphasizes that the fund’s edge is backing strong companies outside the usual hubs—without limiting to any single “type” of founder.
- •Typical check sizes and emphasis on larger early checks for higher multiples
- •Targeting ~40–45 companies with selective follow-on participation
- •Small allocation for opportunistic/off-thesis investments
- •Geographic focus beyond Silicon Valley/NY/MA (including broader regions)
- •Positioning: “invest in everybody” while still hunting unicorn outcomes
- 22:38 – 26:18
Biggest challenges and confidence-building: inadequacy, LP access, and VC Unlocked validation
Mac details the hardest parts of becoming a fund manager: internal doubts, lack of an LP network, and practical constraints like travel money. He describes how VC Unlocked and respected mentors provided the validation that he had the knowledge and could compete at the highest level.
- •Imposter feelings tied to nontraditional background (no degree/finance)
- •Finding LPs without an existing fundraising network
- •COVID/Zoom reduced travel costs and enabled high-volume meetings
- •VC Unlocked experience confirmed he already knew much of the material
- •Mentor/professor validation as a turning point
- 26:18 – 29:45
Staying grounded through hype: early zeros, Twitter fame, and return-focused perspective
Mac explains how he avoids complacency: remembering past failures and focusing on realized returns over paper markups. He also reflects on the surreal nature of sudden Twitter-driven visibility and how it opened unexpected doors like podcasts and TV outreach.
- •Paper gains don’t matter until returns materialize
- •Early investing humility: first three investments at Maryland went to zero
- •Twitter growth from 2,500 to 50,000+ followers as a major surprise
- •Visibility effects: industry buzz, emotional fan reactions, new opportunities
- 29:45 – 32:58
Rolling funds and modern fund ops: keeping a traditional fund while borrowing the best tech
Mac views rolling funds as a symptom of venture’s slow innovation but credits them for pushing new fundraising options. He explains why he avoided the rolling fund model (fairness across LP quarters) and instead built a traditional fund with rolling-close mechanics and streamlined digital onboarding.
- •Rolling funds framed as productization of existing legal/structural tools
- •Core objection: quarter-by-quarter participation can disadvantage small LPs
- •Preference for LP equity across the full life of a fund
- •Using 506(c) solicitation while maintaining a traditional fund structure
- •Operational tooling: web-based subscription flow and frequent closes
- 32:58 – 42:35
Advice, long-term ambition, and quick-fire: building a top-tier Baltimore firm + Unspun investment
Mac shares lessons for new managers—fundraising is harder than expected and rules can be reimagined—then paints his long-term vision: building a top-tier, multi-stage Baltimore-based firm. In the quick-fire, he covers his favorite book, handling stress, the family tradeoffs of venture, what he’d change about the industry, and why he invested in Unspun.
- •Fundraising reality check and encouragement to innovate on structure
- •10-year vision: building a top-tier multi-stage firm rooted in Baltimore
- •Follow-on investors will fund strong metrics regardless of geography
- •Hardest job element: being present for family amid a 20-year commitment
- •Favorite book: Reginald F. Lewis biography and its personal significance
- •Recent investment: Unspun’s zero-waste, 3D-printed apparel manufacturing vision
