Link Live with Lorenzo Costa

This week, we are back in the studio for Episode 20. Host Lorenzo, CEO of Link Creative, is joined by Allan Perales, the Founder and CEO of Kain Real Estate.Allan is a veteran of the hospitality and real estate landscape who has spent over two decades bridging the gap between service and sales. From his early career at Kimpton Hotels & Restaurants to his eight-year tenure as Director of Leasing at McCaffery Inc., Allan has built a reputation as a "hospitality-first" broker. After helping launch over 100 independent restaurants and national brands as a Partner at Goldstreet Partners, Allan recently launched Kain Real Estate, a firm designed to run a brokerage with the precision and soul of a luxury hotelier. Allan joins the pod to discuss the "Kimpton Moments" that define elite customer service, the calculated risk of going solo after 20+ years in the industry, and why the Filipino word for "to eat" (Kain) is the perfect nod to his mission.Inside the EpisodeIn this conversation, Lorenzo and Allan break down the journey from classical music performance to private equity, detailing how hospitality principles can revolutionize the transactional world of real estate:The Hotel Blueprint: Allan reflects on his seven years with Kimpton Hotels and how learning to deliver "Kimpton Moments" random acts of kindness that cost the company nothing, became his primary business lever.The Craigslist Pivot: A masterclass in resourcefulness, Allan shares how he once posted a fake job listing just to study the resumes of top property managers and successfully pivot his own career path during a hiring freeze.Pro-Bono Growth Strategy: How Allan and his former team used the pandemic to build a "moat" by helping independent chefs restructure their leases for free, eventually becoming the most trusted restaurant brokers in Chicago.The Michelin Standard: A deep dive into the technical side of restaurant real estate, from helping the team at Galit navigate complex hood codes to finding "destination" locations for icons like Kasama.Building the Platform: Why Allan is now focused on mentoring the next generation, specifically hiring from the bartending world where grit, personality, and the "gift of gab" are forged.“Get rid of the arrogance and focus on your mindset. You can train the voice in your head to stop being the naysayer and start being your number one cheerleader.” — Allan PeralesALLAN PERALES:Instagram: @allan__perales Website: kainrealestate.com LINK CREATIVE:Website: linkcreativeco.com YT: @linkcreativeco INSTAGRAM: @linkcreativeco TIKTOK: @linkcreativecoTimestamps00:00 Welcome Allan Perales to the Studio 01:33 From Grocery Stores to "Ground Pat'i" in Louisiana 02:36 The Kimpton Training: Learning the Art of Caring 03:52 Transitioning to Chicago & The Hotel Burnham 05:26 The Craigslist Job Post: Hacking the Property Management Algorithm 06:44 Hotel Standards in Property Management: Increasing Renewal Rates 10:46 The Package Room Revolution: From $700 to $10,000 in Tips 13:10 Moving into Commercial Leasing at McCaffery Inc. 14:27 Joining Goldstreet Partners: The "Eat What You Kill" Mindset

Welcome back to the Link Live Podcast, presented by Link Creative.For Episode 19, host Lorenzo Costa, CEO of Link Creative, is joined by a powerhouse in the Chicago hospitality and real estate scene: Sebastian, the Founder and CEO of The Dream Rental Chicago and the operator of the Plymouth Hotel Chicago.Sebastian is a master of the "Hospitality Pivot," transitioning from a career selling and managing at Cutco into building a massive short-term rental empire. From a "trial by fire" start right before the global pandemic to managing a portfolio of over 100 units, Sebastian joins the pod to discuss the shift from simple "Airbnbs" to high-level boutique hospitality and the grit required to scale in one of the most regulated cities in the country.Inside the EpisodeIn this conversation, Lorenzo and Sebastian break down the evolution from a side-hustle mindset to a high-stakes hospitality CEO:The Arbitrage Advantage: Why renting properties to re-rent them (Arbitrage) allowed Sebastian to scale faster with less capital than traditional real estate investing.Surviving the "Wild West": Navigating the early days of COVID-19, dealing with "disaster scenarios," and the reality of high-stakes parties and property damage.The Shift to Hospitality: Why "staged" properties are failing and why Sebastian is positioning his brand as the "Host of Chicago" to survive the algorithm.The Plymouth Project: A behind-the-scenes look at winning a bankruptcy auction for a hotel and the massive operational leap from single units to full-building management.“Revenue is vanity, profit is sanity. As you grow a business, it’s less about the numbers and more about who you are becoming to actually handle that stress.” — SebastianSEBASTIAN & THE DREAM RENTALSInstagram: @sebas___tianBusiness Instagram: @thedreamrentalsWebsite: thedreamrentals.comLINK CREATIVE:Website: linkcreativeco.comYT: @linkcreativecoInstagram: @linkcreativecoTikTok: @linkcreativecoLinkedIn: Link Creative00:00:00 Intro & Hook00:00:32 Guest Introduction00:01:37 Upbringing & Early Career00:02:27 First Airbnb & Surviving Covid00:05:33 Airbnb Arbitrage vs. Traditional Rentals00:08:01 Navigating Chicago Regulations00:10:08 Crazy Airbnb Horror Stories00:11:35 How to Get Started in Arbitrage00:15:29 Building a Hospitality Brand00:17:46 Quitting the 9-to-5 Job00:19:20 Transferable Skills from Sales00:21:39 Building Systems & Hiring a Team00:23:25 Best Software Tools for Airbnb00:26:26 The Value of a Business Partner00:28:24 Best Locations to Invest00:30:46 Expanding Out of State & Internationally00:33:08 Future Portfolio Goals00:34:27 Realistic Profit Margins00:36:00 Leveraging Debt to Scale00:37:51 The Plymouth Hotel Acquisition00:43:50 Hotel Operations vs. Airbnbs00:46:31 Driving Additional Revenue Streams00:48:22 Social Media & Networking00:50:52 Managing Stress & Preventing Burnout

Welcome back to the Link Live Podcast, presented by Link Creative. For Episode 18, host Lorenzo Costa, CEO of Link Creative, is joined by entrepreneur, former professional basketball player, and financial industry leader Chris Gandy, Founder and CEO of Legacy Wealth Group and President of NAIFA (National Association of Insurance and Financial Advisors).Chris’s journey is one of transformation, discipline, and long-term vision. From growing up in Starkville, Mississippi and later Kankakee, Illinois, to becoming a top national basketball recruit, playing for the University of Illinois, and eventually earning a roster spot with the Chicago Bulls, Chris experienced firsthand the preparation and mindset required to perform at the highest level. After witnessing how many athletes struggled with financial decisions despite earning significant income, he pivoted into financial services, turning a personal curiosity about managing money into a mission to help individuals and families build sustainable wealth and avoid the financial pitfalls he saw throughout professional sports.Today, Chris leads Legacy Wealth Group, advises clients nationwide, and advocates for financial literacy and industry policy through his leadership role at NAIFA.Inside the EpisodeIn this conversation, Lorenzo and Chris break down the transition from athlete to financial leader:- From Small Town to the Big Stage: Chris reflects on growing up in Mississippi and Illinois, discovering basketball, and ultimately becoming a top national recruit before playing at the University of Illinois and later with the Chicago Bulls organization.- Lessons from the Bulls Dynasty Era: Chris shares what it was like practicing alongside elite players and witnessing the discipline, preparation, and relentless work ethic that separated great players from everyone else.- Athletes & Financial Mistakes: After seeing how many athletes mishandled sudden wealth, Chris became determined to build a career helping people make smarter financial decisions and avoid becoming statistics.- The Identity Shift: Chris opens up about transitioning from being known as “Chris the basketball player” to becoming a financial advisor and entrepreneur, learning that what you do and who you are are two very different things.- Building Legacy Wealth Group: After years in the financial industry and leadership roles within major firms, Chris stepped away to build his own company focused on leadership, impact, and generational wealth.- Success vs. Significance: Chris shares how his definition of success evolved from chasing numbers and achievements to focusing on significance, impact, and helping people improve their lives through financial education.CHRIS GANDY:Website: https://tlwgllc.comINSTAGRAM | @coach_cgandyLINKEDIN | Chris GandyLINK CREATIVE:Website: https://linkcreativeco.comYT | https://www.youtube.com/@linkcreativecoINSTAGRAM | https://www.instagram.com/linkcreativeco/ TIKTOK | https://www.tiktok.com/@linkcreativeco

Welcome back to the Link Live Podcast, presented by Link Creative. For Episode 17, host Lorenzo Costa, CEO of Link Creative, is joined by one of the most innovative entrepreneurs in the city: Kyle Casaccio, the CEO and Founder of Sunday Morning Club, Thank You for Dancing, and Old Pro Agency.Kyle is a master of the "Identity Shift," having transitioned from a high-energy hospitality career into building a multi-layered business empire. After years of navigating the nightlife scene, Kyle took a "trial by fire" leap into entrepreneurship, replacing safety nets with a high-stakes obsession with growth. From reclaiming Sundays for thousands with Sunday Morning Club to managing millions in event production costs, Kyle joins the pod to pull back the curtain on the "unsexy" grind: the 18-hour Saturdays, the mental toll of public perception, and the relentless discipline required to scale a brand in the digital age.Inside the EpisodeIn this conversation, Lorenzo and Kyle break down the transition from clinical employee to a high-stakes disruptor:Trial by Fire: Why Kyle believes putting yourself in a position where success is the only option is the ultimate fuel for growth.The Identity Shift: A transparent look at the struggle of moving beyond how people "used to know you" and embracing the evolution into a CEO.Reclaiming the Sunday: The mission behind Sunday Morning Club and how solving a personal problem—wasted Sundays—created a nationwide wellness movement.The "Unsexy" Side of Content: Why Kyle’s strategy of 5 reels a week and raw, authentic storytelling trumps high-production value every time.“If you think you shouldn't do something because you're afraid to do it, then that's a good indicator that you should. Show me someone’s pain tolerance, and I’ll show you how far they’ll go.” — Kyle CasaccioKYLE CASACCIO Instagram: @kylecasaccio Founder: @thankyoufordancing | @sundaymorningclubchicago | @clubcapriparty | @oldproagency | @powderaprespartyLINK CREATIVE: Website: https://linkcreativeco.com YT: @linkcreativeco INSTAGRAM: @linkcreativeco TIKTOK: @linkcreativeco LINKEDIN: Link Creative

This week, we continue our Miami Series with Episode 16, broadcasting live as we dive into the world of high-ticket digital advertising. Host Lorenzo, CEO of Link Creative, is joined by Stevie Johnston, the Founder and CEO of Digital Ox.Stevie is a powerhouse in the agency space, having built an eight-figure marketing empire from the ground up. From a 2.0 GPA student in San Diego who called himself “unemployable” to a dominant force in dental and medical marketing, Stevie built his success on an early fascination with Facebook ads and a No Plan B mentality. Today, Digital Ox manages over 100 clinics across the U.S., combining elite media buying with a proprietary in-house call center to solve the biggest pain point in local business: lead conversion. Stevie joins the pod to discuss the "Pain Tolerance" required to scale past $5M, the $700k tech stack investment that is redefining his 2026 strategy, and why the "freedom" of entrepreneurship often starts with 13-hour days in a restaurant kitchen.Inside the EpisodeIn this conversation, Lorenzo and Stevie break down the journey from skating the streets of Chula Vista to driving a Lamborghini through the streets of Miami:The Unemployable Catalyst: Stevie discusses growing up in an entrepreneurial household and why a 2.0 GPA at Arizona State led him to realize that if he didn't build his own dream, he'd be stuck serving smoothies forever.The "Seven Months to $1" Grind: The brutal reality of the early agency days, the influence of Tai Lopez's early ads, and why most entrepreneurs quit right before the "light at the end of the tunnel" appears.Building the Moat: How Digital Ox transitioned from a simple lead-gen agency to a "Performance Marketing & Call Center" hybrid, solving the "churn" problem by taking over the entire sales cycle for their clients.Scaling to Eight Figures: A transparent look at the "Million Dollar Month" target, the necessity of hiring $200k+ leadership talent, and why Stevie was willing to risk $1M in liquid cash to upgrade his company's "race car" tech stack.Optimizing for Energy: The daily habits of a high-performer, including personal trainers, mobile concierges, and the constant battle against the "Miami temptations" to stay sharp for the next level of growth.“Show me someone’s pain tolerance, and I will show you how far they’re going to go. Pain tolerance is everything.” — Stevie JohnstonSTEVIE JOHNSON:Instagram: @steviejohnston_YouTube: @steviejohnstonCompany: Digital OxLINK CREATIVE:Website: linkcreativeco.comYT: @linkcreativecoINSTAGRAM: @linkcreativecoTIKTOK: @linkcreativeco

This week, we continue our Miami Series with Episode 15, broadcasting from an offsite studio in the heart of Florida’s financial hub. Host Lorenzo, CEO of Link Creative, is joined by Diego Curbelo, the Founder and CEO of Blue Summit Capital.Diego is a rising force in the commercial real estate and asset management sector. Born in Venezuela and raised in Miami, Diego bypassed the traditional "nine-to-five" corporate ladder to build a firm focused on high-stakes acquisitions and property management. By leveraging a deep understanding of the "Sun Belt" market and a disciplined approach to investor relations, he has carved out a niche in one of the most competitive real estate environments in the world. Diego joins the pod to discuss the transition from "internet guru" inspiration to boots-on-the-ground reality, the mechanics of raising capital as a young entrepreneur, and why "sitting on the sidelines" is sometimes the most profitable move a leader can make.Inside the EpisodeIn this conversation, Lorenzo and Diego break down the journey from watching "War Dogs" style hustle in a one-bedroom apartment to managing multi-million dollar real estate pipelines:The Immigrant Hustle: Diego shares the formative experience of watching his father build a spirits brand (Diplomático Rum) from the ground up and how a signed copy of Rich Dad Poor Dad changed his trajectory in the third grade.The Credibility Gap: Strategies for young entrepreneurs to build institutional trust with high-net-worth investors and why property management is the "unsexy" but essential foundation for real estate success.Market Diligence in the Sun Belt: A deep dive into why Blue Summit Capital is cautious in the 2026 market, focusing on oversupply in Class A rentals and the "effective rent" trap.The Investor Lifecycle: Breaking down the legal and financial requirements for accredited investors, and why a 15-18% IRR is the gold standard for their acquisitions.The "No-BS" Miami Network: How to navigate the "fluff" of social media real estate gurus and build a reputation based on longevity and repeated value.“What are you afraid of? You don’t have to have it all figured out. Most people, even the people that you look up to, are still figuring it out.” — Diego CurbeloDIEGO CURBELO:Instagram: @bluesummitcapWebsite: bluesummitcre.comLinkedIn: Diego Andres CurbeloLORENZO COSTA | LINK CREATIVEWebsite: https://linkcreativeco.comYT: @linkcreativecoInstagram: linkcreativecoTikTok: linkcreativecoLinkedIn: linkcreativeco

Welcome back to the Link Live Podcast, presented by Link Creative. This week, we are broadcasting from Miami for Episode 14, officially kicking off our Miami Series. Host Lorenzo, CEO of Link Creative, is joined by Dr. Sterling, Miami’s number one concierge chiropractor and a leading voice in the modern health and wellness space.Dr. Sterling is a powerhouse in the performance healthcare industry, having transitioned from his family’s multi-generational practice in California to founding an elite, "office-less" concierge brand in South Florida. In just over two years, he has amassed tens of thousands of followers and built a high-net-worth client base by replacing the clinical "waiting room" experience with high-end, mobile care. Dr. Sterling joins the pod to discuss the "No Plan B" mindset, the mechanics of modern concierge medicine, and how he’s helping the next generation of practitioners scale their own wellness empires.Inside the EpisodeIn this conversation, Lorenzo and Dr. Sterling break down the journey from a disciplined, all-natural upbringing to scaling a modern health brand in one of the world's most competitive cities:The Concierge Blueprint: Dr. Sterling explains why "time" is the ultimate currency for high-performers and how he delivers elite care on boats, in offices, and at private residences.The "No Plan B" Jump: The mindset required to move across the country and start from scratch, leveraging social media as a digital resume to build instant credibility in a new market.Professionalized Hospitality: Moving beyond the "amateur" health stigma to offer comprehensive outcomes, from dry needling and cupping to specialized mobility work.The Wellness Entrepreneur: A look into Dr. Sterling’s mentorship program, designed to help health practitioners escape the traditional clinic grind and build their own mobile brands.The Blueprint for 2026: Expanding from a solo operator to a full-scale wellness team, integrating IV therapy, peptides, and the future of regenerative medicine.“If you really think you can do this, then you have to go prove it. You just have to shut up or you gotta do it. You have to find out what you can possibly create.” — Dr. SterlingDR. STERLING Instagram: @doctorsterling TikTok: @doctorsterling YouTube: @doctorsterlingLORENZO COSTA | LINK CREATIVEWebsite: https://linkcreativeco.comYT: @linkcreativecoInstagram: linkcreativecoTikTok: linkcreativecoLinkedIn: linkcreativeco00:00 - Teaser & Intro 00:54 - Who is Dr. Sterling? 02:22 - From the Bay Area to Miami 03:08 - Growing Up in a Holistic Family 05:06 - Choosing Chiropractic Over Pro Soccer 07:54 - The Reality of Chiropractic School 09:35 - Moving to Miami with No Plan B 10:48 - Networking in a New City 13:31 - Early Hustle: Pop-ups & Collabs 17:03 - What is Concierge Chiropractic? 19:35 - The Most Overlooked Treatment: Mobility 21:13 - Selling Outcomes vs. Individual Visits 22:42 - The Post-COVID Health Boom 24:26 - Social Media as a Business Necessity 26:42 - Entrepreneurial Advice: "Shut Up or Do It" 28:55 - The Wellness Entrepreneur Program 32:15 - Bad Habits to Break: Inactivity & Vaping 35:05 - The Padel Obsession & Community <

Welcome back to the Link Live Podcast, presented by Link Creative. This week, we are broadcasting from our headquarters at Link Label Studios for Episode 13. Host Lorenzo Costa, CEO of Link Creative, is joined by Sharif Maadi, better known as “Chicago’s Lawyer,” and the President/CEO of Maadi Law.Sharif is a powerhouse in the personal injury space, having transitioned from a dedicated law clerk to the founder of a seven-figure firm in just under two years. Fresh off a massive 2025 - where he secured over $4 million in settlements across 200+ won cases - Sharif joins the pod to pull back the curtain on the reality of the legal profession, the grit required to build a brand from scratch, and the mindset of a high-stakes litigator.Inside the Episode:In this conversation, Lorenzo and Sharif break down the journey from a disciplined upbringing to scaling a modern law firm:The “Lawyer” Stigma: Sharif addresses mainstream misconceptions about the legal profession and explains the grueling “grunt work” and problem-solving required to succeed.The Entrepreneurial Jump: How Sharif leveraged 43 pending cases and a “laser focus” on experience to launch Maadi Law without a safety net.High-Stakes Risk: A look into the personal injury model, where the firm fronts all costs and only gets paid if they win - including the story of a recent $750,000 settlement for a motorcycle accident victim.Scaling Through Digital: The strategy behind the “Chicago’s Lawyer” persona and how radical transparency and education on social media drive business growth.The Blueprint for 2026: Sharif shares his methods for goal setting (and manifesting), from hiring a dream team to transitioning from renting to owning his office space.“Something could be simple but still hard and not easy. Working out is simple: eat healthy, go to the gym. But it’s very hard to do. Business is the same way.” - Sharif MaadiSHARIF MAADI | MAADI LAWInstagram: @chicagoslawyerFacebook: @chicagoslawyerTikTok: @chicagoslawyerLORENZO COSTA | LINK CREATIVEWebsite: https://linkcreativeco.comYT: @linkcreativecoInstagram: linkcreativecoTikTok: linkcreativecoLinkedIn: linkcreativeco

Welcome back to the Link Live Podcast, presented by Link Creative. This week, we are back with another installment from our brand-new headquarters at Link Label Studios. For Episode 12, host Lorenzo Costa, CEO of Link Creative, is joined by Kyle Barrera, Founder and CEO of Axel Luxury.Kyle spent nearly a decade navigating the corporate tech sales landscape before making the ultimate "entrepreneurial jump," famously wiping out his 401k to acquire his first Lamborghini Urus and launch Chicago’s leading exotic car rental agency. In this episode, Lorenzo and Kyle explore the mechanics of high-stakes risk-taking, the mindset required to move from employee to founder, and the unique challenges of pioneering the luxury vehicle market in the Midwest.They dive deep into the importance of disciplined operations, the strategy of managing investor-owned vehicles, and how Kyle uses radical transparency through documentation to build a brand that resonates with professional athletes and entrepreneurs alike. Whether you are an aspiring founder or a business leader looking to understand how to leverage personal branding to scale, this episode offers a masterclass in building a business through risk, grit, and consistency.Subscribe to the Link Live Podcast for more conversations with industry leaders at the intersection of business, creativity, and innovation.KYLE BARRERA | AXEL LUXURY Website: axelluxury.com Instagram: @axelluxury TikTok: @axelluxury Personal IG: @bigkb23LORENZO COSTA | LINK CREATIVE Website: https://linkcreativeco.com YT | / @linkcreativecoINSTAGRAM | / linkcreativecoTIKTOK | / linkcreativeco

Welcome back to the Link Live Podcast, presented by Link Creative. After a short hiatus, we are officially back and broadcasting from our brand-new headquarters at Link Label Studios. To kick off this new season, host Lorenzo Costa, CEO of Link Creative, sits down with Ren Thompson, Founder of Ren Private Jewelers.Ren has spent a decade navigating the jewelry industry, moving from the floor of big-box retailers to building a thriving, seven-figure private jewelry business in the heart of downtown Chicago. In this episode, Lorenzo and Ren explore the grit required to make the "entrepreneurial jump," the transition from employee to founder, and the unique challenges of serving high-profile clients including athletes, celebrities, and entertainers.They dive deep into the importance of discipline, the strategy of data-driven networking, and how Ren intertwines fashion, art, and hospitality to create a luxury client experience that digital-first startups simply can't replicate. Whether you’re an aspiring founder or a business leader looking to refine your client experience, this episode offers a masterclass in building a brand through trust, taste, and consistency.Subscribe to the Link Live Podcast for more conversations with industry leaders at the intersection of business, creativity, and innovation.REN THOMPSON | REN PRIVATE JEWELERSREN PRIVATE JEWELERS:Website: renprivatejewelers.comInstagram: @renprivatejewelersREN THOMPSON:Instagram: @rncckLORENZO COSTA | LINK CREATIVEWebsite: https://linkcreativeco.comYT: @linkcreativecoInstagram: linkcreativecoTikTok: linkcreativecoLinkedIn: linkcreativeco