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 & icebreaker04:25 – Sean’s road from Pinterest to Web308:50 – Accidental entry into fractional life via DAO13:15 – Landing multiple clients & income stacking17:40 – Trail running, wellbeing and work stamina22:05 – Finding (and needing) community as a fractional26:30 – “Frac’d-up moment”: divorce & career reset30:55 – Quickfire: tools, dream/nightmare clients, myths35:20 – Where fractional leadership is headed next39:45 – 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/ Keywordsfractional 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