THE FLIP SIDE with Andy Mai
TFS#105 - Josh Wilson, $330M Deals, Building & Selling Podcasts, Kingdom Syndicate Founder

Josh Wilson is a serial entrepreneur, the founder of Kingdom Syndicate, The Deal Scout Podcast, and many other ventures.
But that's not all! Josh has also wrestled alligators professionally, fought fires, delivered babies, saved lives, built and sold companies (FAILED and PIVOTED more than most), worked with sharks (I mean Venture Capitalists), was one of the first to build an online group fitness company, built and scaled a network of co-working studios in partnerships with local municipalities, built and sold podcasts and media brands, interviewed over 750 Entrepreneurs and CEO’s across 8 Podcast Shows reaching the top of iTunes Charts and the list goes on.
In this episode, Josh shares with us all the highs and lows that brought him to where he is today.
Connect with Josh now at https://www.linkedin.com/in/joshuabrucewilson/
CHAPTERS:
00:00 Intro
00:25 Meet Josh Wilson
02:10 Monetization & Mission
03:20 Building An Audience
05:15 Audience Acquisition
06:30 Audience Growth
07:40 Five-Star Review
08:40 Audience Guiding Principles
10:20 Podcast Monetization
11:50 Striking A Deal
14:00 The Ideal Listeners
17:10 Determining Target Audience
20:05 Pitbull’s Success Story
20:50 Structuring Deals
23:25 The Deal Ecosystem
25:30 The Value Ladders
26:20 Podcast Lost Opportunities
27:30 The Cost Of Guest Acquisition
28:30 Building Relationships
30:10 Option Fatigue Syndrome
31:10 Value Proposition Alignment
33:20 Community Value Accumulation
35:10 Investing On The Business Model
36:45 Invaluable KPIs
37:50 The Long Term Plan
39:05 Managing Podcasts & Business
40:30 Restructuring Offers
42:25 Finding Your Right Fit
44:20 Outro
- Broadcast on:
- 08 Nov 2022
Josh Wilson is a serial entrepreneur, the founder of Kingdom Syndicate, The Deal Scout Podcast, and many other ventures.
But that's not all! Josh has also wrestled alligators professionally, fought fires, delivered babies, saved lives, built and sold companies (FAILED and PIVOTED more than most), worked with sharks (I mean Venture Capitalists), was one of the first to build an online group fitness company, built and scaled a network of co-working studios in partnerships with local municipalities, built and sold podcasts and media brands, interviewed over 750 Entrepreneurs and CEO’s across 8 Podcast Shows reaching the top of iTunes Charts and the list goes on.
In this episode, Josh shares with us all the highs and lows that brought him to where he is today.
Connect with Josh now at https://www.linkedin.com/in/joshuabrucewilson/
CHAPTERS:
00:00 Intro
00:25 Meet Josh Wilson
02:10 Monetization & Mission
03:20 Building An Audience
05:15 Audience Acquisition
06:30 Audience Growth
07:40 Five-Star Review
08:40 Audience Guiding Principles
10:20 Podcast Monetization
11:50 Striking A Deal
14:00 The Ideal Listeners
17:10 Determining Target Audience
20:05 Pitbull’s Success Story
20:50 Structuring Deals
23:25 The Deal Ecosystem
25:30 The Value Ladders
26:20 Podcast Lost Opportunities
27:30 The Cost Of Guest Acquisition
28:30 Building Relationships
30:10 Option Fatigue Syndrome
31:10 Value Proposition Alignment
33:20 Community Value Accumulation
35:10 Investing On The Business Model
36:45 Invaluable KPIs
37:50 The Long Term Plan
39:05 Managing Podcasts & Business
40:30 Restructuring Offers
42:25 Finding Your Right Fit
44:20 Outro