The Capital Flow Podcast

From $100K to $100M: Capital Raising Lessons from Gary Lipsky

Dallon Episode 17

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0:00 | 37:43

The hardest part about raising capital isn’t finding money, it’s earning enough trust that investors offer it.

Learn what’s working right now to attract investors, accelerate trust, and raise capital on autopilot.

Join our FREE Weekly Capital Flow Workshop → https://capitallystpro.io/workshop


The Capital Flow Podcast helps capital raisers and fund managers create flow in their capital, business, and life by learning from those who’ve built systems that attract resources instead of chasing them. Each week, host Dallon Schultz interviews real capital raisers and industry experts who share the strategies, systems, and stories behind raising millions with trust-based relationships.

In this episode, Dallon sits down with Gary Lipsky, Founder of Break of Day Capital, who has raised over $100M in the last six years. Gary shares how he went from struggling to raise his first $100K to consistently closing multi-million dollar deals by becoming a disciplined operator and building systems around education and investor trust. They dive into the mindset shifts required for early capital raisers, the power of running webinars, and how strong asset management directly impacts your ability to raise capital. Whether you're new to syndications or scaling your investor base, this episode gives a real world look at the backend of successful capital raising. Visit breakofdaycapital.com or email info@breakofdaycapital.com to claim Gary’s free book for the first 10 listeners: “Invest Smart: Spotting Red Flags in Real Estate Syndications.”

Sponsor Spotlight
This episode is brought to you by Brad Blazar and Capital School, the Elite Program for Capital Raisers that are looking to scale their business or real estate. 👉 Learn more or access the special offer here: https://go.bradblazar.com/apply-page

Key Takeaways

  • Raising capital is about building long term trust, most investors don’t buy in on the first deal.
  • Educational webinars and monthly content are powerful tools to stay top of mind and nurture potential investors.
  • Strong operations and asset management are what truly create investor confidence and repeat referrals.
  • Vetting operators is more important than vetting the deal, great operators make good deals great and prevent bad ones from sinking.

Resources Mentioned

  • “Invest Smart: Spotting Red Flags in Real Estate Syndications” – book offered by Gary Lipski
  • Concept: Pref vs. Cash on Cash returns
  • Key Quote: “The money is made in the operations.”

Capitallyst Pro Resources:
Weekly Capital Flow Workshops → https://capitallystpro.io/workshop
Email Deliverability Checklist → https://capitallystpro.io/email
ChatGPT Copywriter SOP → https://capitallystpro.io/copy

Legal Disclaimer:
This podcast is intended for informational and educational purposes only. It does not constitute legal, financial, or investment advice, nor is it a solicitation or offer to buy or sell any securities. The hosts and guests share personal experiences and general insights about raising capital compliantly; however, every situation is unique, and compliance with securities laws depends on specific facts and circumstances. Listeners and viewers should seek their own qualified legal, tax, and financial counsel before taking any action. The hosts and production team disclaim any liability for decisions made based on the content of this program.