The Twenty Minute VC

Mac the VC on the Journey from Homeless To Becoming A VC | Full Interview with Harry Stebbings

McKeever “Mac the VC” Conwell II is the founder and managing partner of RareBreed Ventures, a pre-seed fund that invests outside of large tech ecosystems, with a concentrated portfolio approach being the first check with in with up to $250K. Mac’s journey into venture is nothing short of inspirational, Mac went from being homeless to being an engineer to founding his own companies to today, raising Rarebreed largely on Twitter. For more 20VC, check out the podcast: https://podcasts.apple.com/us/podcast/the-twenty-minute-vc-venture-capital-startup-funding/id958230465 In Today’s Episode withMac the VC You Will Learn: 1.) How Mac went from being homeless to becoming an engineer and starting his own companies? How did his time operating lead to his becoming a VC and building his Twitter brand? 2.) What are the biggest ways that venture is messed up today? Why does Mac believe it does not matter about getting into hot deals? Why does Mac believe that the brand of the VC that does your round does not matter? Does Mac see the leading venture brands investing outside SF and NYC? What elements of an investment compel them more than others? 3.) In the wake of the George Floyd event, who does Mac note did not say anything? How does Mac want to see diversity introduced at the institutional LP level? What does Mac believe institutional LPs care about? What can institutional LPs do structurally to allow themselves to invest in the next generation of emerging managers? 4.) Why does Mac not like AngelList Rolling Funds? How did he structure his fund in a creative way? In what way does Mac feel the requirements for GP commits needs to change? How did Mac use Twitter very specifically to raise his fund? Which people went out of their way to help him? What were some of the biggest takeaways from those discussions? #MactheVC #20VC #VentureCapital #HarryStebbings

Harry StebbingshostMac the VC (McKeever Conwell II)guest

Feb 4, 202242mWatch on YouTube ↗

WHAT IT’S REALLY ABOUT

From Homeless Founder To VC: Mac Challenges Venture’s Broken Rules

Mac (Mac the VC), a former software engineer and twice founder, shares his unconventional path into venture capital, culminating in launching RareBreed Ventures without a degree, finance background, or savings. He explains how personal failure, depression, and support from family and friends reshaped his identity beyond startup success. The conversation dives into how he raised a $10M pre-seed fund largely via Twitter DMs and 506(c), while deliberately ignoring many traditional fund rules. Mac also critiques structural problems in venture—especially around hot deals, LP behavior, and performative diversity—while outlining his long-term ambition to build a top-tier, Baltimore-based multi-stage firm.

IDEAS WORTH REMEMBERING

5 ideas

Your worth is not defined by startup success or failure.

After his second company failed, Mac hid at home, depressed, until he realized friends and family loved and respected him regardless of the outcome—freeing him to move forward without tying identity solely to entrepreneurial success.

You can enter venture without a traditional pedigree by leveraging real startup experience and networks.

Despite lacking a degree or finance background, Mac broke into the State of Maryland’s investment arm by emphasizing his founder experience and local startup network, proving non-traditional paths are possible.

Fund structures are far more flexible than most emerging managers are told.

Mac ignored norms on GP commits, first-close percentages, and capital calls, opting for rolling closes, flexible payment schedules for LPs, and zero GP commit, showing emerging managers can design structures that fit their realities.

Social platforms can be powerful fundraising and learning tools if used deliberately.

He used Twitter to identify and DM VCs, took over 1,100 meetings in a few months, and raised his first $2M soft circle, illustrating how consistent content and targeted outreach can substitute for an existing LP network.

Chasing hot deals is a poor proxy for generating real returns.

Mac criticizes the industry’s obsession with “hot” Sequoia-style rounds and LPs using them as validation, arguing that only capital-returning outcomes matter and that pre-seed investors must learn to pick before something is obvious.

WORDS WORTH SAVING

5 quotes

Hot deals do not mean good deals. The deals that matter are deals that return capital.

— Mac

I don't care about any of these rules. These are all just legal structures—they can be changed.

— Mac

When I started raising the fund, I was broke. I wasn’t even an accredited investor.

— Mac

If you're growing 40% month over month with strong margins, you’ll get a check from somebody somewhere.

— Mac

I’m going to build the next NEA, the next Greenspring Associates, the next top-tier firm—based out of Baltimore.

— Mac

Mac’s unconventional journey from failed founder and government contractor to VCEmotional fallout from startup failure and redefining self-worthBuilding RareBreed Ventures: fund strategy, structure, and Twitter-led fundraisingBreaking traditional venture norms on fund closes, GP commit, and legal structuresSystemic issues in venture: hot deals, LP incentives, and shallow diversity effortsSupporting overlooked founders outside major tech hubs with large pre-seed checksLong-term vision to build a top-tier, Baltimore-based, multi-stage venture platform

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