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Build Your Plan. Build Your Team. Build Your Legacy.

Investor Retreat 2025 Chicago (Oct 16-18)

A working retreat where you’ll start, scale, and protect your real estate investing business.

3 days. One city.

The blueprint to grow your portfolio, fund your future, and build wealth with purpose.

Why this retreat

Most events inspire. This one installs a plan. Over three focused days, you’ll leave with a 12-month business plan, the how-to for your first or next acquisitions, and a complete team blueprint—so you can execute without repeating avoidable mistakes.

Built for:

  • Aspiring investors ready for Door #1 (without guesswork)

  • Experienced investors who want to scale with systems

  • Realtors who want to invest or lead investor clients

Prices increase to $397 after September 1st at 11:59 PM CST

What you’ll walk away with

  • A clear, immediate 12-month business plan

  • Practical how-to for first and next acquisitions

  • A defined team blueprint (who to plug in, when, and what to ask)

  • Confidence to execute like a seasoned operator—minus the rookie mistakes

How the three days flow

Oct 16 — Arrivals & Warm-Intro Networking

Check in, get grounded, then join a casual happy hour with guests, speakers, sponsors, and resource partners. Expect warm introductions to the people investors actually need in their rolodex—experts and MVPs it would take years for an experienced investor to build out.

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Oct 17 — Foundations & First-Deal Mastery (Day 1)

Set it up right so you operate like a pro:
   •    Goal setting & business planning
   •    Entity formation and business structure
   •    Deal identification (criteria; what makes a good deal)
   •    Team for this stage—who you need now and why
   •    Capital partners & financing options (real paths to fund the first/next deal)

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​Outcome: Leave Day 1 feeling like you’ve “been investing for years,” leveraging hard-won lessons to avoid common mistakes.

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Oct 18 — Protection, Strategy Mix & Scaling (Day 2)

Keep, grow, and scale wealth with smart structures and systems:

  • Asset protection and tax strategies

  • Wealth planning & building generational wealth

  • From first door to the next: leverage options & financing strategy

  • Property management options (you don’t have to do it alone)

  • Choosing STR vs. MTR vs. LTR (Airbnb and beyond) and when each fits

  • Scaling strategy: long-term planning and systems to expand sustainably

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Outcome: Clarity on how to build, grow, and keep wealth—plus the next steps and support to do it.

© 2025 We Wealthy University

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