Oh Frac! | Ep 01: Sean MacMannis — From Pinterest to Fractional Freedom

Sean MacMannis traded scaling Pinterest’s ads to $1B for scaling his own freedom. In this episode of Oh Frac!, host Adir Ron unpacks Sean’s journey from big-tech marketer to Web3 DAO builder, trail-running dad, and fractional marketing coach. You’ll hear how one “soft-landing” freelance gig snowballed into multiple clients, why diversified income beats one oversized paycheck, and the surprising link between ultra-running and executive resilience. Whether you’re a founder hunting for fractional firepower or an exec flirting with freelancing, Sean’s candid wins (and frac’d-up missteps) will have you re-thinking the rules of work—and maybe lacing up for your own next big leap.

Key Takeaways

• Freedom beats titles: Sean left marquee roles to design work around family and personal values—proving founders don’t hire résumés, they hire impact.

• Web3 as a fractional sandbox: DAOs normalized contractor relationships early, making crypto a launchpad for on-demand leaders.

• Diversify or die: Multiple clients + side coaching = income stability and stronger negotiation power—vital insight for aspiring fractionals.

• Product-market you: Treat your expertise like a product; niche messaging and personal storytelling convert faster than generic positioning.

• Community is the new cafeteria: Fractionals must replace office camaraderie with curated networks (Fractionals United, District, Next Play) for support and deal flow.

• Trail-running mindset: Endurance sports cultivate the patience, pacing, and grit that consulting life demands.

• Ideal vs. nightmare clients: Great founders know “good marketing” but stay outcome-focused; micromanagers suffocate creativity and results.

• Myth-busting: Fractional ≠ “just part-time”—it’s strategic impact without full-time overhead.

• Choose your change: Make big transitions sequentially (industry or work model first) to avoid overwhelm.

• Future forecast: Fractional roles won’t replace FTEs, but will become a mainstream growth lever every savvy startup understands.

Chapters

00:00 – Welcome, show intro & icebreaker 04:25 – Sean’s road from Pinterest to Web3 08:50 – Accidental entry into fractional life via DAO 13:15 – Landing multiple clients & income stacking 17:40 – Trail running, wellbeing and work stamina 22:05 – Finding (and needing) community as a fractional 26:30 – “Frac’d-up moment”: divorce & career reset 30:55 – Quickfire: tools, dream/nightmare clients, myths 35:20 – Where fractional leadership is headed next 39:45 – Sean’s one-sentence advice & episode wrap

Sean’s LinkedIn: https://www.linkedin.com/in/seanmacmannis/ Sean’s Trail & Error: https://trail-and-error.beehiiv.com/ Adir’s LinkedIn: https://www.linkedin.com/in/adir-ron/

Keywords fractional leadership, fractional CMO, Web3 marketing, DAO contracting, diversified income, trail running mindset, startup growth, executive coaching, Pinterest ads, Clubhouse, future of work, SaaS scaling, fractional toolkit, community for consultants