In this episode, I sit down with Annie Dickerson, co-founder and Chief Brand Officer of Good Egg Investments, to talk about her journey from fourth-grade teacher to leading one of the most dynamic real estate syndication firms in North America. Annie shares how she discovered real estate investing through house hacking and eventually transitioned to building a portfolio that has helped thousands of investors place over $1.4 billion into commercial real estate.
We dive deep into how Annie and her business partner educate new investors, build trust through approachable branding, and scale a mission-driven company. Annie also unpacks how her background in psychology and education helps her demystify complex topics—and why she’s passionate about bringing consciousness and personal growth into investing. Whether you’re actively raising capital or passively investing, this episode is a goldmine of strategy, mindset, and vision.
Episode Timeline
[0:00] - Introduction
[3:03] - Meet Annie Dickerson: Teacher turned real estate syndicator and co-founder of Good Egg Investments
[5:06] - Real estate without the landlord headaches: How syndications work for passive investors
[6:38] - The evolution from house hacking to helping thousands invest passively
[8:19] - Annie’s early career in education, game design, and how it led her to real estate
[11:06] - Learning the language of investing and the power of “cash flow positive”
[14:06] - Raising capital through trust, transparency, and education
[17:45] - The difference between trying to “look smart” and making your investor feel smart
[20:31] - Why creating an investor avatar (“Jen”) changed the way Annie’s team produces content
[24:18] - Do investor avatars exclude people? Annie explains why they do the opposite
[27:58] - Choosing multifamily as the perfect onramp for new investors
[30:54] - Helping investors visualize risk through relatable, everyday examples
[33:10] - Customizing investor experiences based on their level of understanding
[35:56] - The importance of meeting investors where they are—emotionally and strategically
[37:05] - Knowing when to say no: Why Annie sometimes turns away eager investors
[40:07] - Money as energy: A new lens for understanding your wealth and your goals
[44:40] - The multifamily market outlook and why Annie is bullish on 2025
[47:28] - Merging real estate with personal growth, psychology, and human design
[50:00] - The future of Good Egg: Creating holistic investing experiences for a new generation
Five Key Takeaways
1. Start with Education – Annie’s background as a teacher deeply influences how she communicates with investors, using simple, relatable language to empower instead of overwhelm.
2. Define Your Ideal Investor – Crafting a fictional avatar like “Jen” helps Good Egg tailor their messaging and offerings with clarity and focus.
3. Make Investors Feel Smart – Rather than showcasing expertise, Annie emphasizes making investors feel understood and informed, which builds lasting trust.
4. Mindset Matters – Investing isn’t just about numbers—your mindset, beliefs about money, and ability to reflect on setbacks shape your long-term success.
5. Conscious Capital – Annie sees the future of investing as a blend of financial growth and personal development, connecting wealth to purpose and alignment.
Links & Resources
• Visit Good Egg Investments: https://goodegginvestments.com/
• Listen to Annie’s podcast: https://podcast.goodegginvestments.com/
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