Make AI Your Deal Analysis Expert - Turn Fear Into Your Fundraising Superpower
Is AI coming for your job… or just your boring tasks? In this episode, Jillian and Nate get real about the fears AND massive potential of using AI in the capital raising world. From comparing AI to the advent of cars (yes, really) to breaking down how tools like ChatGPT can save you hours in underw…
Stop Pitching, Start Connecting | The Real Secret to Selling Investors | Ep 144
In this episode, Nate and Jillian show us what it really takes to sell investment opportunities the right way. Spoiler: it's not about being pushy—it's about building real relationships.
Nate shares why raising capital is different from selling anything else and why trust, connection, and good ol…
From 0 to 45 Rentals: How Jake Ostrich Built His Real Estate Empire Without a PM | Ep 145
🔥 In this episode of the Capital Raising Show by Investor Attraction Academy, we sit down with Jake Ostrich, the founder of Lighthouse Capital, who's raised over $1M and built a 45-property rental portfolio—all while staying hands-on and self-managing flips. He reveals how he transitioned from gene…
Build Your Dream Syndication Team | Legal, Accounting & Marketing Made Simple | Ep 146
Dream teams aren't just for sports—they're the secret to syndication success. In this episode, Nate Dodson lays out exactly who you need in your corner, from sharp legal counsel to savvy accountants, creative marketers, and tech-powered funding portals.
You'll discover:
When to hire a bookkee…
Inside Tracy Prigmore's $3.2M Debut in Hotel Investing | Ep 147
In this episode of The Capital Raising Show, host Nate Dodson sits down with Tracy Prigmore — hotel owner, operator, and developer — to uncover the unique opportunities and challenges in hospitality investments.
Tracy shares her path into the hotel industry and what makes hotels such a compelling …
The Right Way to Use AI for Investor Outreach with Jillian Sidoti
Most investor outreach fails because it sounds fake.
In this episode, Jillian Sidoti shares how to use AI and automation to raise capital while still sounding human. She explains how to connect with the right people, start real conversations, and build trust before ever making a pitch.
How to Raise Capital: Sell the Underwriting, Not the Real Estate Deal
In this episode, Jillian Sidoti shares her insights on real estate investing, capital raising, and leveraging AI to automate and scale her business. She discusses her focus on luxury travel, experiential stays, and the importance of building strong investor relationships.
Professional Real Esta…
Investment Offering Documents Explained: Operating Agreements, PPMs, Subscription Agreements and More
Before investing in a syndication, fund, or private placement,
you may be handed more than 100 pages of legal documents.
But what are those documents actually telling you,
and what should you be looking for before you sign?
In this session of the Alternative Investing Mastery Series, Patrick…
How to Travel Cheap in Retirement and Still Hit Bucket List Trips w/ Jillian Sidoti
[Ep 198]
Worried that travel in retirement will either drain your savings or shrink your adventure list to the same beach every year? You can see the world on a budget that fits a real retirement plan, and this episode shows Gen X women and couples exactly how it works.
Jillian Sidoti, a former att…
How Real Estate Money Actually Gets Raised — Jillian Sidoti ($4B+) | Equity or Bust Ep. 3
Capital is everywhere. Trust is the deal.
In Episode 3 of Equity or Bust, Young and Leo sit down with Jillian Sidoti — a securities attorney who has helped entrepreneurs raise more than $4 billion. Jillian breaks down how real estate money actually gets raised: how to find your true investor, how t…
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