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Podcast Booking, Board Seats, and Speaking Platforms Guide

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Podcast Booking, Board Seats, and Speaking Platforms Guide

Source: Sean Fleener call 2026-03-24

Part 1: Podcast Booking

StagePlatformCostWhy
Start nowPodMatch Standard$32/moVolume, low cost, dating-app matching model
Add secondPodzay Pro$19/moAI matching, cheap, different network
Targeted outreachPodseeker$49/moDatabase + CRM for cold-pitching top shows
Done-for-youPodcast Bookers$700/moAgency handles everything, SEO value

One-Sheet Checklist (Create in Canva)

  • Professional headshot
  • Bio (3rd person, 3-4 sentences — host reads as your intro)
  • 5 topic options with hooks:
    1. “Why Your Small Business Is a Bigger Cybersecurity Target Than You Think”
    2. “The Fractional CIO Model: Enterprise Expertise at SMB Prices”
    3. “Responsible AI for the Rest of Us: What SMBs Need to Know”
    4. “Disaster Recovery Reality Check: Why 60% of SMBs Can’t Actually Recover”
    5. “Conscious Business Meets Technology: Building Resilient Organizations”
  • 5-7 suggested interview questions
  • Social proof (credentials, past appearances)
  • Contact info + Calendly link
  • 60-second video pitch for PodMatch profile

10 Best Podcast Categories for Dmitri

  1. SMB/Small Business Strategy
  2. Cybersecurity for Business (non-technical audience)
  3. AI and Business Transformation
  4. IT Leadership / CIO-CTO Conversations
  5. Nonprofit Management/Operations
  6. Conscious Business / Purpose-Driven Leadership
  7. Disaster Recovery / Business Continuity
  8. Entrepreneurship / Solopreneurship
  9. Colorado Business / Local Spotlights
  10. Managed Services / IT Channel (referral partner audiences)

Cold-Pitching Tips

  • Keep under 150 words
  • Reference a specific recent episode you listened to
  • 15-20% success rate for personalized pitches
  • Follow up at 3, 7, and 14 days (20% of bookings come from follow-ups)

Part 2: Board Seats

Nonprofit Boards (Start Here)

PlatformCostNotes
Spark the Change ColoradoFreeBoard Leadership Connection program, Denver-area. Contact: (303) 551-0624
BoardSourceFree to searchNational, well-governed nonprofits
VolunteerMatchFreeFilter by “board member” + cause area
BoardStrongTBDFocus on diverse candidates
IdealistFreeWide variety of positions

Corporate/Advisory Boards (Later)

  • BoardAssist — 25+ year track record, primarily NYC but serves nationally
  • Boardsi — PROCEED WITH CAUTION, significant negative reviews, pay-to-play model
  • LinkedIn — Add “Open to Board Membership Opportunities” to headline (65% of connections happen here)
    • Currently 90+ board positions listed in Denver, 245+ in Colorado

Progression Strategy

Year 1: Join 1-2 Colorado nonprofit boards (technology/cybersecurity gap fill) Year 2-3: Committee leadership → advisory board position with local startup Year 3-5: Corporate advisory boards, NACD membership for credibility

Positioning Fractional CIO for Boards

  • From: “I provide fractional CIO services to SMBs”
  • To: “I provide technology governance and cybersecurity oversight to organizations lacking senior tech leadership”
  • Lead with: risk oversight, regulatory fluency, business translation, breadth across industries

Part 3: Public Speaking

Toastmasters (Denver/Boulder)

  • Boulder Speakeasy — Fridays noon, St. John’s Episcopal, 1419 Pine St
  • Downtowners TM — Wells Fargo Center, 1700 Lincoln St, Denver
  • Simply Speaking TM — President’s Distinguished since 2008
  • Cost: ~$80-100/6 months
  • Visit 2-3 clubs before joining

Better Alternative: NSA Colorado

  • National Speakers Association Colorado — Monthly meetings Sep-May
  • Speakers Academy for professional development
  • Guest pass: nsacolorado.org/be-our-guest-25-26
  • More aligned with Dmitri’s goals than Toastmasters

Denver/Boulder Speaking Opportunities

  • Boulder Startup Week (May 4-8, 2026) — FREE, 200+ events, accepts speaker proposals
  • Colorado Startup Week (Sep 16-18, 2026) — Submit proposals
  • New Tech Colorado (bdNewTech) — Monthly, 12K+ members, multiple cities
  • Boulder AI Builders — Every 6 weeks, 200-250+ attendees
  • Startup Grind Denver — Regular fireside chats
  • Denver AI meetups — DenAI Summit, Women in AI Colorado

Virtual Speaking

  • LinkedIn Live / Audio Events (free, build audience)
  • Industry webinars: ISACA, CompTIA, local chambers
  • ILA AI & Leadership Virtual Summit (May 6-7, 2026)

The Credibility Flywheel

Podcast appearances → build content library → speaking invitations Board service → governance credibility → more compelling podcast guest Speaking engagements → visibility → board recruitment

Start with podcasts — lowest barrier, fastest feedback loop.

Action Items (Next 30 Days)

  • Create podcast one-sheet in Canva
  • Sign up PodMatch ($32/mo) + Podzay (free)
  • Update LinkedIn with board-focused language
  • Contact Spark the Change Colorado
  • Visit NSA Colorado as guest
  • Submit speaker proposal for Boulder Startup Week (May 4-8)

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