Raw and Relentless w/ Bo DePaoli

Fast-growing startups often hit an invisible wall—and more often than not, the root cause is people. In this episode of Raw and Relentless, Bo sits down with Nahed Khairallah, founder of Organized Chaos, to talk about how scaling companies from seven to nine figures requires more than product-market fit and financing—it demands building the right team, culture, and infrastructure.

Nahed also shares wild consulting stories—from uncovering massive payroll fraud in a 40,000-person telecom to helping founders step away and actually enjoy their businesses.

📚Learn more atorganizedchaos.fyi
 🎙️ Listen to his podcast: Organized Chaos
 📲 Connect with Nahed onLinkedIn or email: [email protected]

What do you get when you mix six-time CEO experience, a love for high-performance teams, and a seat at the McLaren Racing table? You get Brendan Keegan. In this powerhouse episode of Raw and Relentless, Bo sits down with Brendan to unpackhis journey from coding in New Hampshire to running billion-dollar companies—and what it really takes to transform underperforming teams into market leaders. Brendan shares how he scaled a tech company with backing fromCisco and Dell, navigated a brutal dot-com bust, and built a fleet services business from $500M to $2.5B in revenue.

Check out his book: Dare to Disrupt

More from Brendan: brendanpkeegan.com

IG: @bpkfearless

LinkedIn: BrendanP. Keegan

In this episode of Raw and Relentless, Bo sits down with Alex Levin, CEO and co-founder of Regal.ai, a platform building AI agents that are transforming how enterprise brands communicate with customers. Alex dives deep into thecurrent capabilities (and limitations) of AI agents—what they’re really good at (think tier-one support, appointment scheduling, and lead qualification), and what still requires a human touch. He breaks down how Regal integrates with CRMs like HubSpot and Salesforce, why voice is quickly becoming the most cost-effective communication channel, and how AI agents are already outperforming humans in speed, accuracy, and personalization. If you’re a business owner looking to automate and elevate your customer experience—or just want a front-row seat to where AI is heading—this episode isa must-listen.

🔗 Learn more: regal.ai
 📧 Contact: [email protected]
Try their AI dog demo at regal.ai/dog

How do you go from a Marine standing at attention outside the Oval Office to running a multi-million dollar parking business? Jonathan Velarde did just that. In this episode, he shares his journey from presidential security at Camp David and the White House to becoming an entrepreneur in the valet andparking lot industry, scaling his business to over $3 million in revenue across two states.g out, this conversation is a must-listen for anyone serious about building wealth through real estate.

Connect with Jonathan Velarde:

📲 Instagram: @parkingmogul

📲 Business: @valetparkingpros

In this episode of Raw and Relentless, Bo sits down with real estate investor and podcast host Kassidy Warren, who shares how he went from renting out a spare bedroom for $35 a night to acquiring boutique hotels. Kassidy dives into his journey of scaling in the short-term rental space, discussing the challenges, lessons, and strategies that helped him build a real estate portfolio. He also reveals why 2025 is his "Year of Reach and Reputation," emphasizing the power of content creation, networking, and leveraging appreciation over cash flow to maximize long-term wealth.If you’re looking to scale your business, create influence, or master real estate investing, this episode is packed with actionable insights. Kassidy breaks down the key to surviving in the evolving Airbnb market, why securing high-value properties beats managing dozens of smaller ones, and how he’s using podcasting as a tool for networking and deal-making. Whether you're a seasoned investor or just starting out, this conversation is a must-listen for anyone serious about building wealth through real estate.

Connect with Kassidy Warren:

● Instagram: @kassidy.warren

In this episode of Raw and Relentless, host Bo DePaoli sits down with online health coach Jack Sorenson, who went from being an engineer to transforming the lives of busy entrepreneurs through sustainable health and fitness strategies. Jack shares his personal weight loss journey, the challenges of starting an online coaching business, and why so many people struggle with fitness due to information overload. He breaks down the misconceptions around dieting, why walking is underrated, and how business owners can prioritize their health without sacrificing productivity. Tune in for actionable fitness advice, debunked diet myths, and an inspiring conversation about building a thriving coaching business.

Connect with Jack Sorenson:

● Instagram: @sorensonfit

What happens when two best friends turn their passion for financial freedom into a thriving real estate empire? In this episode of Raw and Relentless, Bo sits down with Cory Jacobson and Ryan Bevilacqua to discuss their journey from house hacking a single property to managing a portfolio of over 80 rental units. They reveal how networking, strategic partnerships, and mindset shifts accelerated theirgrowth—plus why investing in yourself is the ultimate key to success. Whether you're looking to buy your first rental or scale up, this episode is packed with actionable insights you won’t want to miss!

Connect with Cory Jacobson & RyanBevilacqua:

• Instagram: @wealthjuiceofficial

They also share content on YouTube and host TheWealth Juice Podcast

In this episode of Raw and Relentless, we sit down with entrepreneur and investor Sam Khairi to talk abouthis transition from corporate engineering to real estate investing and business acquisitions. Sam shares how he went from working in high-stakes construction and utility jobs to building wealth through real estate syndications and, mostrecently, acquiring and scaling home service businesses. We discuss the power of mindset, why stacking businesses can lead to massive scale, and how leadership plays a crucial role in success. If you're looking to level up your entrepreneurial game, this episode is packed with insight!

Connect with Sam Khairi:

●     Instagram: @officialsamkhairi

●     Website: https://www.aftocapital.com/

In this episode of Raw and Relentless, Bo sits down with Ben Erwin, CEO of Charitybuzz, to explore the innovative ways his platform is revolutionizing charitable giving. Charitybuzzis the premier marketplace that offers once-in-a-lifetime experiences—such as playing golf with Larry David, meeting Hollywood A-listers, or attending exclusive film premieres—all while supporting critical nonprofit initiatives. Ben provides an in-depth look at the stagnation of charitable contributionsover the last 50 years and how his organization is leveraging the multi-billion-dollar non-essential activities market to create new fundraising channels. He discusses the transformative power of public-private partnerships,the need for nonprofit organizations to embrace for-profit business models, and how the creation of charity endowment funds could drive long-term impact. Whether you're passionate about giving back, intrigued by high-profile experiences, or looking for fresh ways to make a difference, this episode ispacked with game-changing perspectives you won’t want to miss!

Learn more about Charitybuzz:

●     Website: https://www.charitybuzz.com/

In this episode of Raw and Relentless, Bo sits down with securities lawyer and entrepreneur Bethany LaFlamto break down the complexities of raising capital safely. Bethany shares insights on leveraging OPM (Other People’s Money) through SEC-compliant strategies, explains the differences between 506(b) and 506(c) exemptions, and discusses how real estate investors can scale without burnout. She also dives into her journey from big law to launching her own fund, offering valuable lessons on mindset, strategy, and business growth.
If you’ve ever wanted to learn how the big players raise money and build lasting wealth, this episode is a must-listen!

Connect with Bethany LaFlam :

●     Instagram:@bethany_laflam