Raw and Relentless w/ Bo DePaoli

Episode 51: Join Bo DePaoli as he uncovers the gripping life of Lyubim Kogan , from his harrowing escape during 9/11 , Olympic dreams, Wall Street success, and his groundbreaking mission, Wings for Heroes , supporting wounded veterans. Lyubim’s journey takes us from Soviet-era Ukraine to becoming an elite trader, surviving the financial crisis without losses, authoring a national bestseller, and f...

Episode 50: In this episode of Raw and Relentless , Bo sits down with Gino Ferrand , founder of Tekla, to unpack how startups and mid-market companies are scaling by tapping into LatAm developer talent—without sacrificing quality, time zones, or culture fit . Gino shares how Tekla helps tech companies build high-performing engineering teams in Latin America, the realities of global hiring, and why...

Episode 49 How Jay Conner Raises Millions Without Banks or Hard Money Banks shut him out during the 2009 crash. Instead of quitting, Jay Conner discovered private money—and never looked back. In this Raw and Relentless episode, Bo sits down with Jay Conner to unpack how he’s raised over $8.5 million in private lending , flipping 500+ homes without relying on traditional banks or hard money. Jay br...

Episode 48: Why can’t some 20-somethings handle a late fee or call in sick on their own? In this Raw and Relentless episode, Jess Hein and Bo DePaoli explore how over-involved parenting keeps young adults from building real-life skills, from making appointments to handling responsibilities. We also unpack how labels and diagnoses can shape identity—and why focusing on them too much can hold kids b...

Move over Expedia—air freight just got its own AI concierge. In this episode of Raw and Relentless , Bo sits down with Chris Connelly, co-founder of Aircon AI and the mind behind Captain Cargo , an AI-agent ecosystem that quotes, books, and reroutes international shipments in under two minutes. They break down: Why speed—not cheapest price—wins40-50 % of air-freight bids How Captain Cargo pushed r...

In this week's episode of Raw and Relentless, host Bo DePaoli welcomes his friend Kate Hastings, a seasoned jiu-jitsu practitioner and entrepreneur. They discuss Kate's transformative journey through personal struggles, her move from Miami to St. Petersburg, and the launch of her business, Phoenix Fit, which emphasizes mental and emotional well-being. The conversation touches on the life-c...

In this podcast episode, Michel Langlois shares insights from his extensive career in Silicon Valley, covering companies like Cisco, Juniper, and Calix. He discusses the transformation and scaling of businesses, as well as the economic and societal impacts of broadband and digital innovation. Michel also explains his motivation behind writing his book 'Beyond the Code,' which aims to inspi...

In this episode of Raw and Relentless , Bo sits down with Anthony Calvanese—former mechanical/professional engineer turned Italian citizen, entrepreneur, and cultural bridge. After quitting his job, selling his house, and moving across the world, Anthony shares how he reclaimed his heritage, built two thriving businesses in Italy, and learned to thrive in a slower, more intentional lifestyle. They...

In this powerful episode of Raw and Relentless, we sit down with Carl Dumesle, a remarkable immigrant from Haiti who shares his incredible journey of resilience and determination. After experiencing the devastating earthquake in 2010, Carl and his brothers were forced to leave their home and navigate life in the Dominican Republic before ultimately moving to San Diego. He reflects on the challenge...

The Custom Code Advantage:Why Ben Johnson Says ERP Isn’t Always the Answer When off-the-shelf software can’t keep upwith your business—do you keep duct-taping it together, or build your own? In this episode of Raw and Relentless , Bo sits down with Ben Johnson, founder and CEO of Particle41, a firm that builds high-performance custom software, data systems, and AI-powered tools for fast-growing co...

What if the safest bet in real estate… wasn’t the property itself—but the mortgage behind it? In this episode of Raw and Relentless , Bo sits down with Nic DeAngelo, founder of Saint Investment Group, to unpackhow his fixed-income fund is delivering double-digit IRRs through discounted, non-performing mortgage notes—while helping homeowners stay in their homes Plus, they dive into U.S. manufacturi...

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 share...

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. Bren...

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 requ...

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,...

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...

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 informatio...

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 the...

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. W...

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 ini...

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 als...

In this episode of Raw and Relentless, host Bo DePaoli welcomes Matt McLean, founder and CEO of Uncle Matt’s Organic, America’s leading organic orange juice brand. From humble beginnings on a three-acre backyard grove to distribution in over 20,000 stores, Matt shares the highs and lows of building a thriving organic business.  Matt reveals how a conversation with a German buyer in the '90s sparke...

In this episode of Raw and Relentless, Bo DePaoli sits down with Andrew Einhorn, founder of LevelFields.ai, a game-changing platform for event-driven investing. Andrew’s journey from public health researcher to tech entrepreneur is packed with fascinating twists—like uncovering mercury pollution in the Gulf of Mexico and building AI systems for the Pentagon. Andrew shares how his passion for data...

In this episode of Raw and Relentless, Bo DePaoli sits down with Tom Kubiniec, founder and CEO of SecureIt Tactical, Inc. Tom shares his remarkable journey from aspiring heavy metal guitarist to leading a successful company that specializes in innovative weapons storage solutions for both military and civilian markets.  Tom discusses the challenges he faced, including the impact of sequestration o...

In this episode of Raw and Relentless, host Bo DePaoli welcomes Brian Beckcom, a multifaceted attorney, podcaster, and Brazilian jiu-jitsu enthusiast. Brian shares his inspiring journey from a childhood marked by personal tragedy to becoming a relentless advocate for his clients in the courtroom. He discusses the importance of persistence, the complexities of the U.S. healthcare system, and the ch...