Shouting into the void on socials? Heidi Medina shows how conversation-first beats algorithms and drives real career change and success.
In this week’s episode, I sit down with Heidi Medina, a 35+ year, 5X entrepreneur and social selling strategist who’s helped 350+ service providers and coaches spark intentional online conversations that connect and sell, without the awkward pitch.
Now based in Portugal, Heidi frees clients from algorithm-chasing by turning comments and connections into paying work and collaborations through conversation-first marketing. You’ll hear how that approach grew from her own five-business journey, landscaping, cleaning, enterprise social, and more.
You’ll learn a practical framework for writing meaningful comments, why “great post” stalls relationships, and how to redefine conversions (follows, DMs, invites) so your pipeline reflects real human momentum.
We also cover resilient career change: patient timelines, learning from failure, and why proactive follow-up ends more sales droughts than any content hack.
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Chapters:
00:00 Welcome & “Take Two” intro
00:51 First business at 13: $300 → $1,100 flowers
04:23 From layoff to cleaning biz, then enterprise social & coaching
06:43 Uni vs real-world skills; $60k lessons
10:32 AI, digital safety & what schools miss
13:42 Gen X as the bridge generation
15:23 Craigslist lessons & early online marketing
18:20 Conversation-first marketing vs content-first
20:16 Build trust by talking (not broadcasting)
21:40 Autism, entrepreneurship & why corporate didn’t fit 25:19 People work differently; manage to strengths
28:38 Youth entrepreneurship & changing workplaces
33:50 Human detail vs generic AI content
35:19 A comment framework that actually connects
37:40 Why “Great post” isn’t a strategy
44:35 Better to say nothing than “well done”?
48:14 Stop chasing impressions; chase conversations
50:49 Redefining conversions: follows, DMs, invites
53:35 Ending threads & doing the follow-up
56:31 Top 3 tips for human online conversations
58:47 Career change advice: patience, help, fail forward 1:00:50 Wrap-up & thanks