Planning season is here, and this year, the community gets a behind-the-scenes look at how JWB shapes its strategy long before the predictions go public. In this episode, host Pablo Gonzalez sits down with JWB Co-Founder Gregg Cohen and President Alex Sifakis to walk through how JWB plans for the future — live from the new JWB building in Downtown Jacksonville!This episode explores the internal process: how the leadership team interprets early signals, how conversations evolve, where debates sharpen the vision, and how t...
Planning season is here, and this year, the community gets a behind-the-scenes look at how JWB shapes its strategy long before the predictions go public. In this episode, host Pablo Gonzalez sits down with JWB Co-Founder Gregg Cohen and President Alex Sifakis to walk through how JWB plans for the future — live from the new JWB building in Downtown Jacksonville!
This episode explores the internal process: how the leadership team interprets early signals, how conversations evolve, where debates sharpen the vision, and how today’s approach differs from the early “good old days.” With Gregg and Alex together, expect insight, candor, and the dynamic that longtime community members love.
They’ll unpack:
- How JWB filters market data into an actionable strategy for 2026.
- The leadership conversations that shape priorities long before they’re published.
- The evolution of JWB’s planning process, from early days to today’s structured approach.
If you want to understand the thinking behind JWB’s biggest calls, and learn how to apply that decision-making style to your own investing, this episode gives you the blueprint.
Listen NOW!
Chapters:
00:00 Introduction and Holiday Greetings
01:54 Summit Tickets and Event Details
03:12 Sneak Peek into JWB Headquarters
04:06 The Importance of Planning
06:02 Deep Dive into JWB's Planning Process
11:54 Team-Centric Decision Making
17:47 Business Planning Output and Structure
20:43 Company Ownership and Financial Complexity
21:23 Understanding Market Trends and Strategy
22:07 Executive Summaries and Team Involvement
22:57 Director Roles and Business Planning Process
23:39 Employee Contribution to Business Planning
27:07 Intense Final Week of Business Planning
29:47 Consensus-Based Decision Making
33:28 Evolution of Business Planning
36:01 Family and Business Planning Parallels
39:18 Summit and Final Thoughts
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