The Raising Capital Show

Hosted by Nate Dodson & Jillian Sidoti

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149

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Aug 2026

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Hosted by Nate Dodson & Jillian Sidoti, The Raising Capital Show features real conversations with movers and shakers from the world of alternative investing. Get ready to discover the mindsets and strategies of top capital raisers that you can use to raise a lot more capital and build your empire!

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August 7, 2026Episode 14959 min

How a $100M+ Hotel Syndicator Communicates With Investors | The Raising Capital Show

Are you looking to improve your investor closing success? In many cases, the assumption is that the issue comes down to the pitch itself. The deck needs improvement, the webinar needs to be sharper, or the presentation needs to sound more polished. But what's missing is the actual investor conversations; the issue is usually happening much earlier in the process. Jenniffer Maldonado is an incredibly successful hotel syndicator, closing and running a portfolio of hotels of more than $100 million in hospitality. She also runs a separate women-focused investor capitalization program called the Rapid Raise Method. ===================================== ✅ Subscribe To Our YouTube Channel: @entrepreknew Stay plugged into weekly insights, founder interviews, and practical strategies to build momentum as a modern entrepreneur. Leave a comment to let us know what you'd like to see next! 🎙 Hosted by Nate Dodson of Investor Attraction Academy. ✅ Connect With Us On Social Media - Official Links Facebook Group – Join 4,000+ capital-raising pros inside: Capital Raising Talk With Capital Raising Pros Nate Dodson Facebook Instagram LinkedIn 🎓 Explore the Academy Learn how to consistently attract aligned investors through our training and tools. #CapitalRaising #PodcastMarketing #InvestorAttraction #Syndication #RaisingCapital

September 19, 2025Episode 14824 min

Episode 148 – Podcasting for Capital | The Raising Capital Show with Nate Dodson & Dave Dubeau

In episode 148 of The Raising Capital Show , Nate Dodson sits down with Dave Dubeau to discuss how syndicators and fund managers use podcasting as a direct path to raising more capital. Instead of chasing downloads or trying to book celebrity guests, there is a smarter approach: design your show around your investor avatar, highlight them as guests, and use each episode as a stepping stone toward accredited investor meetings. Then repurpose the show's content for marketing outreach as an end-to-end marketing system. This is how to structure interviews to open up investment conversations, build your authority in the investment world, and repurpose podcast content into a full marketing system. Here are some real-world examples of syndicators who used this approach to secure investments and even connect with billion-dollar fund managers. Highlights: "Forget downloads. The real value is in interviewing your ideal investors directly." "Podcasting becomes your relationship-building machine, not just another piece of media." "With the right system, every episode creates trust, authority, and new opportunities for discovery calls." Timestamps: (02:08) Why most podcasts fail to attract investors (05:27) Designing your show around the investor avatar (08:10) Structuring interviews that build trust and authority (11:05) Transitioning from interviews to discovery calls (13:50) Repurposing episodes into marketing content (17:20) Success stories from syndicators using this strategy (20:30) How podcasting becomes a top-to-bottom investor funnel 💼 For capital-raising systems that bring in investors every month: 👉 https://findmoreinvestors.com/ 🎧 Also available on Spotify, Apple Podcasts, and all major streaming platforms. ===================================== ✅ Subscribe To Our YouTube Channel: @entrepreknew Stay plugged into weekly insights, founder interviews, and practical strategies to build momentum as a modern entrepreneur. Leave a comment to let us know what you'd like to see next! 🎙 Hosted by Nate Dodson of Investor Attraction Academy. ✅ Connect With Us On Social Media - Official Links Facebook Group – Join 4,000+ capital-raising pros inside: Capital Raising Talk With Capital Raising Pros Nate Dodson Facebook Instagram LinkedIn 🎓 Explore the Academy Learn how to consistently attract aligned investors through our training and tools. #CapitalRaising #PodcastMarketing #InvestorAttraction #Syndication #RaisingCapital

August 28, 2025Episode 14744 min

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 asset class. From breaking down the franchise model to weighing the benefits of buying versus building, she offers a behind-the-scenes look at how successful operators think. The conversation also dives into Tracy's initiative, She Has a Deal , which is opening doors for women to gain education, mentorship, and capital access in commercial real estate. She explains why partnerships are essential in ground-up development, how emerging manager programs are shifting the landscape, and why integrity is the foundation of any capital raise. If you've ever wondered how to approach hotel investments or what it takes to bring more diversity into real estate, this episode delivers insights you won't want to miss. 💼 For capital-raising systems that bring in investors every month: 👉 https://findmoreinvestors.com/ 🎧 Also available on Spotify, Apple Podcasts, and all major streaming platforms. ===================================== ✅ Subscribe To Our YouTube Channel: @entrepreknew Stay plugged into weekly insights, founder interviews, and practical strategies to build momentum as a modern entrepreneur. Leave a comment to let us know what you'd like to see next! 🎙 Hosted by Nate Dodson & Jillian Sidoti, Partners of Investor Attraction Academy. ✅ Connect With Us On Social Media - Official Links Facebook Group – Join 4,000+ capital-raising pros inside: Capital Raising Talk With Capital Raising Pros Nate Dodson Facebook Instagram LinkedIn Jillian Sidoti Facebook Instagram LinkedIn 🎓 Explore the Academy Learn how to consistently attract aligned investors through our training and tools. COPYRIGHT NOTICE: This video and our YouTube channel contain original content owned by EntrepreKNEW LLC. You're welcome to share the link or embed the video, provided you credit the original channel: EntrepreKNEW on YouTube © EntrepreKNEW LLC 🏷️ RELATED HASHTAGS #EntrepreKNEW #CapitalRaising #InvestorAttraction #FoundersMindset #StartupsThatScale #PurposeDrivenBusiness #RaiseCapitalLegally #InvestmentReady #ModernEntrepreneurship #EntrepreneurLife #MissionDrivenFounder #FinancialFreedom #GenerationalWealth #BusinessClarity #StartAndScale

August 20, 2025Episode 14626 min

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 bookkeeper vs. CPA vs. auditor The essentials of staying compliant (without the headache) Marketing moves that actually bring in investors How to use funding portals to make your life easier Whether it's your first deal or your tenth, this episode will help you build a syndication team that's compliant, profitable, and fun to work with. ===================================== 💼 For capital-raising systems that bring in investors every month: 👉 https://findmoreinvestors.com/ 🎧 Also available on Spotify, Apple Podcasts, and all major streaming platforms. ===================================== ✅ Subscribe To Our YouTube Channel: @entrepreknew Stay plugged into weekly insights, founder interviews, and practical strategies to build momentum as a modern entrepreneur. Leave a comment to let us know what you'd like to see next! 🎙 Hosted by Nate Dodson & Jillian Sidoti, Partners of Investor Attraction Academy. ✅ Connect With Us On Social Media - Official Links Facebook Group – Join 4,000+ capital-raising pros inside: Capital Raising Talk With Capital Raising Pros Nate Dodson Facebook Instagram LinkedIn Jillian Sidoti Facebook Instagram LinkedIn 🎓 Explore the Academy Learn how to consistently attract aligned investors through our training and tools. COPYRIGHT NOTICE: This video and our YouTube channel contain original content owned by EntrepreKNEW LLC. You're welcome to share the link or embed the video, provided you credit the original channel: EntrepreKNEW on YouTube © EntrepreKNEW LLC 🏷️ RELATED HASHTAGS #EntrepreKNEW #CapitalRaising #InvestorAttraction #FoundersMindset #StartupsThatScale #PurposeDrivenBusiness #RaiseCapitalLegally #InvestmentReady #ModernEntrepreneurship #EntrepreneurLife #MissionDrivenFounder #FinancialFreedom #GenerationalWealth #BusinessClarity #StartAndScale

August 13, 2025Episode 14521 min

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 general contracting to full-time investing, why he walked away from 45 properties in Philly, and what he looks for when flipping a house in today's saturated market. Whether you're a new investor or raising capital for your own deals, Jake drops real-world wisdom on contractor management, calculating risk vs. reward, and how to avoid getting burned by shady bids. This is an unfiltered look at what it really takes to grow in real estate—minus the fluff. 💼 For capital-raising systems that bring in investors every month: 👉 https://findmoreinvestors.com/ 🎧 Also available on Spotify, Apple Podcasts, and all major streaming platforms. ===================================== ✅ Subscribe To Our YouTube Channel: @entrepreknew Stay plugged into weekly insights, founder interviews, and practical strategies to build momentum as a modern entrepreneur. Leave a comment to let us know what you'd like to see next! 🎙 Hosted by Nate Dodson & Jillian Sidoti, Partners of Investor Attraction Academy. ✅ Connect With Us On Social Media - Official Links Facebook Group – Join 4,000+ capital-raising pros inside: Capital Raising Talk With Capital Raising Pros Nate Dodson Facebook Instagram LinkedIn Jillian Sidoti Facebook Instagram LinkedIn 🎓 Explore the Academy Learn how to consistently attract aligned investors through our training and tools. COPYRIGHT NOTICE: This video and our YouTube channel contain original content owned by EntrepreKNEW LLC. You're welcome to share the link or embed the video, provided you credit the original channel: EntrepreKNEW on YouTube © EntrepreKNEW LLC 🏷️ RELATED HASHTAGS #EntrepreKNEW #CapitalRaising #InvestorAttraction #FoundersMindset #StartupsThatScale #PurposeDrivenBusiness #RaiseCapitalLegally #InvestmentReady #ModernEntrepreneurship #EntrepreneurLife #MissionDrivenFounder #FinancialFreedom #GenerationalWealth #BusinessClarity #StartAndScale

July 1, 2025Episode 14423 min

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 old-fashioned conversation matter more than slick pitches. From avoiding the hard close to leveraging credibility and using tech wisely, this episode is full of real-world tips on how to connect with investors and grow your network the human way. Tune in to find out why your sales calls aren't closing and what to do instead. Quick Takeaways: People invest in people—become a friend before you pitch Asking for $100K is emotional, not just logical Forget one-call closes—it takes time and follow-up Share stories, ask questions, listen more than you talk Borrow authority if you're new—credibility matters 🎙 Hosted by Nate Dodson & Jillian Sidoti, Partners of Investor Attraction Academy. 🔔 Subscribe To Our Channel Stay plugged into weekly insights, founder interviews, and practical strategies to build momentum as a modern entrepreneur. Leave a comment to let us know what you'd like to see next! ✅ Connect With Us On Social Media - Official Links Facebook Group – Join 4,000+ capital-raising pros inside: Capital Raising Talk With Capital Raising Pros Nate Dodson Facebook Instagram LinkedIn Jillian Sidoti Facebook Instagram LinkedIn 🎓 Explore the Academy Learn how to consistently attract aligned investors through our training and tools. COPYRIGHT NOTICE: This video and our YouTube channel contain original content owned by EntrepreKNEW LLC. You're welcome to share the link or embed the video, provided you credit the original channel: EntrepreKNEW on YouTube © EntrepreKNEW LLC 🏷️ RELATED HASHTAGS #EntrepreKNEW #CapitalRaising #InvestorAttraction #FoundersMindset #StartupsThatScale #PurposeDrivenBusiness #RaiseCapitalLegally #InvestmentReady #ModernEntrepreneurship #EntrepreneurLife #MissionDrivenFounder #FinancialFreedom #GenerationalWealth #BusinessClarity #StartAndScale

June 24, 2025Episode 14340 min

Dean Marchi Details the Value-Add & Customer-First Strategies of his 100-Year Capital Raising Success | Ep 143

This episode dives into how Dean Marchi and his family started from the bottom and listened to the market to deliver what tenants really want. This is how he differentiated his apartments from other multifamily real estate performing incredibly even against the top developers. Dean shares actionable lessons and specific strategies from decades of hands-on experience, showing how a disciplined, value-add approach and relentless attention to detail lead to outsized returns and long-term success in raising capital. Key Takeaways: Start with the end user—know what renters or buyers want Value-add works: target underperforming assets and improve them Differentiate by delivering features others overlook Consistent small improvements compound over time Hands-on involvement builds deep understanding and trust Adopt a resilient, "immigrant mentality" for every deal Apply lessons from other industries to stand out in real estate 🎙 Hosted by Nate Dodson, Partner of Investor Attraction Academy. 👇 Connect With Dean Marchi LinkedIn Website 🔔 Subscribe To Our Channel Stay plugged into weekly insights, founder interviews, and practical strategies to build momentum as a modern entrepreneur. Leave a comment to let us know what you'd like to see next! ✅ Connect With Us On Social Media - Official Links Facebook Group – Join 4,000+ capital-raising pros inside: Capital Raising Talk With Capital Raising Pros Nate Dodson Facebook Instagram LinkedIn Jillian Sidoti Facebook Instagram LinkedIn 🎓 Explore the Academy Learn how to consistently attract aligned investors through our training and tools. COPYRIGHT NOTICE: This video and our YouTube channel contain original content owned by EntrepreKNEW LLC. You're welcome to share the link or embed the video, provided you credit the original channel: EntrepreKNEW on YouTube © EntrepreKNEW LLC 🏷️ RELATED HASHTAGS #EntrepreKNEW #CapitalRaising #InvestorAttraction #FoundersMindset #StartupsThatScale #PurposeDrivenBusiness #RaiseCapitalLegally #InvestmentReady #ModernEntrepreneurship #EntrepreneurLife #MissionDrivenFounder #FinancialFreedom #GenerationalWealth #BusinessClarity #StartAndScale

June 17, 2025Episode 14229 min

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 underwriting and investor outreach, this is your down-to-earth guide to bringing AI into your workflow—without needing to become a tech wizard. They'll walk you through practical, copy-paste prompts, the actual role of APIs (no jargon, promise), and how to use AI like the best employee you've ever trained. Plus, get the scoop on their free AI Deal Desk Starter Kit that's already helping other investors speed up results and save serious brainpower. What You'll Learn Why AI isn't scary—it's just undertrained (and you're the trainer) How to shave hours off deal analysis with the right prompts What ChatGPT and Claude are really good at (and what they're not) How APIs and tools like Zapier help you connect the dots Why vague prompts = vague results (and how to get specific like a pro) How to write better investor emails with AI (and avoid sounding like a robot) 🎙 Hosted by Nate Dodson & Jillian Sidoti, Partners of Investor Attraction Academy. 🔔 Subscribe To Our Channel Stay plugged into weekly insights, founder interviews, and practical strategies to build momentum as a modern entrepreneur. Leave a comment to let us know what you'd like to see next! ✅ Connect With Us On Social Media - Official Links Facebook Group – Join 4,000+ capital-raising pros inside: Capital Raising Talk With Capital Raising Pros Nate Dodson Facebook Instagram LinkedIn Jillian Sidoti Facebook Instagram LinkedIn 🎓 Explore the Academy Learn how to consistently attract aligned investors through our training and tools. COPYRIGHT NOTICE: This video and our YouTube channel contain original content owned by EntrepreKNEW LLC. You're welcome to share the link or embed the video, provided you credit the original channel: EntrepreKNEW on YouTube © EntrepreKNEW LLC 🏷️ RELATED HASHTAGS #EntrepreKNEW #CapitalRaising #InvestorAttraction #FoundersMindset #StartupsThatScale #PurposeDrivenBusiness #RaiseCapitalLegally #InvestmentReady #ModernEntrepreneurship #EntrepreneurLife #MissionDrivenFounder #FinancialFreedom #GenerationalWealth #BusinessClarity #StartAndScale

June 10, 2025Episode 14121 min

Inside the Demand for Assisted Living Facilities with Marv McGuire | Ep 141

On this episode, Nate Dodson interviews Marv McGuire about his move from multifamily real estate into assisted living and memory care deals in Florida. Marv explains how he structures deals allowing for both risk management and asset protection. He not only shares the macro factors that make memory care facilities more attractive than multifamily but also how he navigates the far more stringent compliance associated with this type of investment. Marv's current focus is on acquiring assisted living portfolios and converting them to memory care facilities, to meet the overwhelming and growing market demand. 🎙 Hosted by Nate Dodson, Partner of Investor Attraction Academy. 👇 Connect With Marv McGuire LinkedIn Facebook 🔔 Subscribe To Our Channel Stay plugged into weekly insights, founder interviews, and practical strategies to build momentum as a modern entrepreneur. Leave a comment to let us know what you'd like to see next! ✅ Connect With Us On Social Media - Official Links Facebook Group – Join 4,000+ capital-raising pros inside: Capital Raising Talk With Capital Raising Pros Nate Dodson Facebook Instagram LinkedIn Jillian Sidoti Facebook Instagram LinkedIn 🎓 Explore the Academy Learn how to consistently attract aligned investors through our training and tools. COPYRIGHT NOTICE: This video and our YouTube channel contain original content owned by EntrepreKNEW LLC. You're welcome to share the link or embed the video, provided you credit the original channel: EntrepreKNEW on YouTube © EntrepreKNEW LLC 🏷️ RELATED HASHTAGS #EntrepreKNEW #CapitalRaising #InvestorAttraction #FoundersMindset #StartupsThatScale #PurposeDrivenBusiness #RaiseCapitalLegally #InvestmentReady #ModernEntrepreneurship #EntrepreneurLife #MissionDrivenFounder #FinancialFreedom #GenerationalWealth #BusinessClarity #StartAndScale

May 19, 2025Episode 14029 min

Don't Pitch Until You're Positioned: How to Build Investor Confidence and Authority First | Ep 140

With rising interest rates, increased investor skepticism, and deals that haven't gone as planned over the past few years, Nate and Yakov share gems on how to lead with transparency, authority, and empathy. This isn't about promising sky-high returns anymore. It's about communicating proactively, addressing fear before it becomes a deal-killer, and presenting yourself with a sense of credibility. Key Takeaways: How to position yourself to deal with investor fears before objections arise How to build trust & authority even without a long track record How "burnt-out" investors are thinking differently (and what they still want) Tips for engaging long-term investors (self-directed IRAs and 401(k)s) Real-world strategies to drive engagement and referrals A/B testing to improve your one-to-many outreach and one-to-one relationship building Effective (and not so effective) steps to scaling and implementing a system Useful links and resources: https://findmoreinvestors.com/apply Yakov Smart's new book 'Attracting Investors' on Amazon Join our capital raising community group here: https://www.facebook.com/groups/capitalraisingtalkwithcapitalraisingprosgroup Free Trainings on "How To Raise More Capital & Find High Net-Worth Investors on Auto-Pilot": http://findmoreinvestors.com/capital Enter our monthly raffle by leaving a 5-star review and emailing a screenshot to: reviews@findmoreinvestors.com Connect with Yakov: https://www.linkedin.com/in/yakovsavitskiy/ https://www.facebook.com/yakov.smart3 The following music was used for this media project: Music: Positive Fat Bass Intro Loop by WinnieTheMoog Free download: https://filmmusic.io/song/6093-positive-fat-bass-intro-loop License (CC BY 4.0): https://filmmusic.io/standard-license Artist website: https://linktr.ee/taigasoundprod The following music was used for this media project: Music: Just Keep Going (Loopable) by chilledmusic Free download: https://filmmusic.io/song/7245-just-keep-going-loopable License (CC BY 4.0): https://filmmusic.io/standard-license The following music was used for this media project: Music: Business Of Dreams by MusicLFiles Free download: https://filmmusic.io/song/9392-business-of-dreams License (CC BY 4.0): https://filmmusic.io/standard-license Artist website: https://cemmusicproject.wixsite.com/musiclibraryfiles