McKeever "Mac" Conwell, Founder and Managing Partner of Rare Breed Ventures, joins Planet Wealth CXO Mary Katherine Johnson to break down how he went from a government contractor in Maryland to launching a venture capital fund built for overlooked founders. Mac shares the unconventional path that shaped his investing lens: dropping out of school for a Northrop Grumman opportunity, building and exiting a startup through pivots and accelerators, and then entering state-backed investing where he helped design a first-of-its-kind pre-seed program for women and minorities.
This episode is a masterclass in capital raising, investor marketing, and community-powered fundraising. Mac explains why most founders struggle to raise money: not because their ideas are worse, but because they lack access to early friends-and-family capital, warm investor networks, and the confidence to talk about money. He walks through how he used Twitter (now X) to build trust at scale, create consistent value, and convert conversations into investor relationships without leading with an ask. The result was a fundraising engine driven by credibility, storytelling, and relentless reps.
Mac also gets tactical about fundraising compliance, outlining why 506C matters for public solicitation under the JOBS Act, and how a founder's content and consistency can become a real distribution advantage. Then he goes deeper: the "North Star" behind his fund, how values shape who you should take money from, and why execution and self-care must coexist if you want to survive entrepreneurship long-term.
If you want a practical, no-fluff conversation about raising capital outside the major tech hubs, building investor trust, and staying human in the process, this is the one. Watch the full episode of Fortunes of the Brave for the complete framework.
Key Takeaways:
• Build trust before you ask by sharing useful insights consistently
• Use storytelling to make fundraising about mission, not transactions
• Leverage 506C to publicly discuss fundraising while staying compliant
• Create momentum with reps: conversations, feedback loops, and iteration
• Protect your health and identity so the business does not consume you
Chapters:
• 00:00 – Meet Mac Conwell and Rare Breed Ventures
• 01:10 – From government contractor to founder and exit
• 02:32 – The state-backed pre-seed fund and "ask forgiveness" leadership
• 06:38 – The real fear for founders: marketing and finding investors
• 07:17 – How Twitter became the distribution channel
• 11:13 – DM strategy, learning-first meetings, and early LP wins
• 14:19 – Email storytelling to drive closes
• 18:04 – Getting comfortable talking about money and yourself
• 20:35 – Fundraising without a pitch deck: the 3-part story
• 22:51 – The North Star story that defined the fund
• 32:26 – 506C vs 506B: how public solicitation worked
• 39:07 – Community flywheel: give first, ask later
• 41:48 – Failure, burnout, and the self-care non-negotiable
• 49:44 – Final advice: "You are enough."
Resources Mentioned:
• Rare Breed Ventures
• Twitter/X as a fundraising channel
• JOBS Act fundraising rules (506B and 506C)
• Regulation Crowdfunding (Reg CF)
• Harbor Bank of Maryland (public-private partnership example)
• Hustle Fund (Elizabeth Yin)
• Accenture partnership example
• Kauffman Fellows program
• American Express (IP acquisition reference)
• Bill Me Later (sold to PayPal)
Connect with Mac:
• Website
• LinkedIn
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