Founder2Founder with Aaron Spivak

In this episode of Founder2Founder, Aaron Spivak sits down with Richart Ruddie, serial entrepreneur, art collector, and founder of CaptainCompliance.com. Richart has built and exited multiple ventures across marketing, tech, and real estate, including one of the largest ORM agencies in the U.S.From hustling calling cards as a teen, to selling a business at 24, Richart breaks down how he built a career by spotting overlooked opportunities and outworking everyone in the room. He shares the hard lessons behind scaling, selling, hiring, and why ignoring compliance could cost your company everything.Chapters:02:26 – Growing Up in Baltimore & Entrepreneurial Roots 03:35 – First Job Punching Calling Cards at Age 12 05:39 – Why “$10M” Isn’t the End Goal 07:19 – How College Shaped His Hustle 09:41 – Graduating Debt-Free Through Work Ethic 11:01 – Grit vs. Moats: Why Outworking Wins 12:06 – Giving First: A Foundational Principle 14:16 – Books That Changed His Life 19:44 – The First Business Exit: Dumpster Rentals at 24 21:13 – Breaking Into SEO & Internet Arbitrage 23:32 – How He Scaled a Boring Business Fast 25:39 – Selling Leads in a Non-Tech Industry 26:46 – Exit Strategy: When to Sell and Why 28:06 – Building Profile Defenders From a Craigslist Ad 29:25 – Scaling to $90K/Month in Under a Year 31:00 – Private Equity Exit in 2023: How It Went Down 32:11 – Systems vs. Team: What Buyers Really Look For 33:49 – Why He Left 7x Revenue Growth on the Table 37:48 – The Compliance Opportunity Most Founders Miss 40:07 – From Removal Services to Privacy Software 41:54 – Understanding Regulatory Risk in Scaling 44:31 – Real Lawsuits: The Wake-Up Call for Founders 46:55 – How $500/Month Could Have Saved a $5M Lawsuit 49:08 – Hiring Strategy: Culture, Grit & Technical Testing 50:46 – The One Interview Question That Says It All 53:44 – Building & Exiting in a Hyper-Competitive Market 55:19 – Advice to His 15-Year-Old Self 58:08 – Why Going Deep, Not Wide, Builds Real AdvantageGuest Links: Website: https://captaincompliance.com/LinkedIn: https://www.linkedin.com/in/richartruddie/The Founders Club: The premier community for founders pursuing excellence in the mind, body, and business.Stay Connected!Aaron Spivak:IG: @‌SpivakLinkedinThe Founders ClubIG: @‌TheFoundersClubWebsite www.foundersclubofficial.com Founder2Founder:TikTok @‌Founder2FounderPodcastYoutube @‌Founder2Founder.Podcast

In this episode of Founder2Founder, Aaron Spivak sits down with media entrepreneur, author, and political commentator Armstrong Williams. From growing up on a tobacco farm in South Carolina as one of 10 siblings, to becoming one of the most influential minority-owned media executives in the country, Armstrong shares how discipline, faith, and preparation shaped every stage of his journey. He is the founder of Howard Stirk Holdings, co-owner of The Baltimore Sun, and host of multiple nationally syndicated TV and radio shows.Armstrong breaks down how early lessons in personal finance, responsibility, and character led him to build long-term wealth and credibility. He reflects on the people and decisions that shaped his career, including his relationship with Senator Strom Thurmond, investing in real estate before 30, and why he refuses to compromise on principle, even when it costs him. His approach to relationships, leadership, and legacy is a blueprint for staying grounded while building big.Chapters02:42 – Growing Up on a Farm & Learning Discipline from His Parents05:56 – Meeting Senator Strom Thurmond: A Life-Altering Moment06:32 – Interning in DC & Discovering His Calling08:43 – Naivety, Risk & Being Ready When Opportunity Arrives11:42 – The Story of His Father Buying Their Family Farm14:56 – Early Lessons on Judging Character as Individuals, Not Groups17:29 – How His Upbringing Influenced the Naming of His Company19:12 – Getting Cut Off Financially & Learning He Was an Entrepreneur21:46 – His Father's Rule: Always Squirrel Away 20%23:09 – The $200 Check That Turned Into $42K: His First Business Win26:31 – Convincing Richard Pryor to Speak for Black History Month28:16 – Meeting His First Business Mentor Through This Event29:36 – Investing $25K That Turned Into $7M by Age 2730:35 – The Power of Long-Term Wealth & Strategic Investing34:53 – The Importance of Giving Back & Empowering Others36:25 – Why Most Young Entrepreneurs Don’t Understand Morality39:05 – Managing Hundreds of Relationships with Intention44:13 – Creating & Scaling Howard Stirk Holdings49:56 – Buying His First Network TV Stations51:12 – The Power of Local Media and Deciding Elections54:03 – Why He’ll Never Be Compromised by Advertisers57:20 – Why Revenge Is a Dangerous Game in Business & Politics59:33 – On Mistakes, Regret, and Taking Full Responsibility1:03:39 – Why He Personally Signs Every Check in His Business1:05:45 – The Power of Hard Conversations and Emotional Maturity1:10:35 – Intuition, Spiritual Currency & Reading Energy1:15:56 – Why Soul > Strategy for Long-Term Success1:23:28 – The One Thing Young Founders Need to Start Doing1:35:26 – Advice to His 17-Year-Old SelfGuest Links:Website: armstrongwilliams.comInstagram: @realarmstrongwilliamsX: @arightside The Founders Club: The premier community for founders pursuing excellence in the mind, body, and business.Stay Connected!Aaron Spivak:IG: @‌SpivakLinkedinThe Founders ClubIG: @‌TheFoundersClubWebsite www.foundersclubofficial.com Founder2Founder:TikTok @‌Founder2FounderPodcastYoutube @‌Founder2Founder.Podcast

In this episode of Founder2Founder, Aaron Spivak sits down with Brandon Pourmorady, founder of Adhesive Media, a powerhouse influencer marketing agency that’s brokered over $20M in YouTube sponsorships to date. Based in Miami and representing over 200 creators monthly, Brandon is at the forefront of the creator economy, matching performance-driven YouTube channels with leading consumer brands. But his journey didn’t start in luxury, it began with bar mitzvah money, garage storage startups, and cold emails sent from a college dorm.Brandon opens up about the formative failures that built his grit, how selling loans at 19 gave him confidence to sell anything, and why taking an underpaid internship taught him more than college ever could. This is a masterclass in resilience, reinvention, and showing up every day even when the outcome isn’t guaranteed.Chapters: 01:17 – Brandon’s Early Drive and Childhood Goals 02:16 – Discovering “Think and Grow Rich” at 15 04:42 – Visualizing Success Before School Every Day 05:47 – Brandon’s First Business Attempt: Amazon FBA 07:31 – Launching Airbnb for Storage and Failing Fast 08:42 – Building a Party App in College That Didn’t Scale 09:20 – Why College Slowed Him Down 12:49 – Advice for Teens: Don’t Trade Learning for “Cool” 14:00 – Taking a Sales Internship at 19 17:22 – Cold Email That Got Him the Job 18:20 – Running 40% of a Pipeline at 19 19:36 – Losing Momentum After Failing at Mask Sales 21:45 – Cold Emailing a Founder and Working for Free 22:50 – Selling Sponsorships for Magic Mind’s Podcast 23:37 – First Six-Figure Deal With Miller Lite 25:00 – Quitting His Job to Go All-In on Adhesive 26:51 – How to Learn While Getting Paid 28:16 – The Real Timeline to $1M in Deals 30:31 – The Power of Apprenticeship Over Courses 31:30 – Why His Age Was an Advantage 32:24 – Using Honest Cold Emails to Land Clients 36:51 – Training Like an Athlete to Compete in Music 38:52 – Being Driven by Integrity Over Approval 40:10 – The Version of Himself He’s Avoiding 43:55 – Rejecting Who He Was at 18 45:50 – Why Reaching Your Potential Matters 47:26 – What He Wants to Be Remembered For 50:02 – Finding Deep Community at Founders Club 52:30 – The ROI of Showing Up 54:35 – Accountability and Environment Fueling Growth 56:02 – Advice to His 16-Year-Old Self 1:00:15 – What Founders Miss Most After the ExitGuest Links:https://www.adhesivemedia.comhttps://www.linkedin.com/in/brandonpourmoradyhttps://www.instagram.com/brandonpomoThe Founders Club: The premier community for founders pursuing excellence in the mind, body, and business.The Founders Club: The premier community for founders pursuing excellence in the mind, body, and business.Stay Connected!Aaron Spivak:IG: @‌SpivakLinkedinThe Founders ClubIG: @‌TheFoundersClubWebsite www.foundersclubofficial.com Founder2Founder:TikTok @‌Founder2FounderPodcastYoutube @‌Founder2Founder.Podcast

In this episode of Founder2Founder, Aaron Spivak sits down with Oleg Lee, a serial entrepreneur, Guinness World Record holder, father of three, and founder of All About Vibe, a custom pillow company that scaled from a garage operation to generating over $60 million in revenue. Known for turning people’s favorite moments into pillows, Oleg has created products for celebrities like Snoop Dogg, Gary Vee, and Paris Hilton, and partnered with brands like Netflix and Paramount.Oleg breaks down the raw, behind-the-scenes reality of building a physical product business from scratch, how a Groupon deal triggered massive demand, working with family, and why he eventually stepped back from daily operations. He shares his goal of a $100 million exit, how he handles adversity and why focusing on health, values, and energy has been his ultimate growth strategy. This conversation is a must-listen for any founder scaling a team or navigating the chaos of entrepreneurship.Chapters: 01:17 – The Dog Pillow That Sparked the Business 02:22 – From Israel to the U.S.: Oleg’s Early Work Ethic 04:05 – The First Custom Pillow: A Tribute to His Dog 05:13 – Building the Business in His Dad’s Garage 07:41 – The Groupon Deal That Created Instant Chaos 08:51 – Fulfilling 20,000 Orders With Family Support 09:59 – From Pre-Made to Fully Custom Designs 11:59 – Transitioning From Wholesale to DTC 12:49 – Working With His Dad: The Challenges and Lessons 14:07 – How Bringing His Wife Into the Business Saved Their Marriage 16:26 – Navigating Family Boundaries in Business 17:13 – Oleg’s Vision for a $100M Exit 19:02 – What He Would Do Differently: No Manufacturing 20:01 – The Problem With Business Advice From Non-Operators 21:30 – Pillows at VCon and Understanding Brand Psychology 23:36 – Creating a Safe and Empowering Culture for Employees 25:15 – Hiring a CEO and Fully Stepping Back 26:28 – Why He Hates Numbers but Still Leads 27:20 – Growing Up in Survival Mode in Beersheba 29:04 – Fixing Machines Himself and Leading by Example 30:22 – What It Took to Build a Self-Sustaining Business 31:37 – The Cost of Listening to the Wrong People 33:13 – Setting a Clear Target for the Exit 36:07 – Aaron’s Story of Selling Hush and Knowing When to Sell 40:34 – Why Oleg Doesn’t Share Product Ideas, He Just Builds 41:31 – Managing Remote Leadership and Scaling From Boca 43:37 – Projected Revenue and the Roadmap to $50M 44:15 – When Summer Outsold Christmas and Production Broke 46:31 – Advice to His 30-Year-Old Self: Prioritize Physical and Mental Health 49:56 – Why Health, Wealth, and Family Are Tattooed Into His Values 51:00 – Surrounding Yourself With the Right EnergyGuest Links:Website: www.allaboutvibe.comInstagram: @thatpillowguyThe Founders Club: The premier community for founders pursuing excellence in the mind, body, and business.Stay Connected!Aaron Spivak:IG: @‌SpivakLinkedinThe Founders ClubIG: @‌TheFoundersClubWebsite www.foundersclubofficial.com Founder2Founder:TikTok @‌Founder2FounderPodcastYoutube @‌Founder2Founder.Podcast

In this episode of Founder2Founder, Aaron Spivak sits down with Kyle Matthews, the Founder and CEO of Matthews™, one of the fastest-growing and now largest privately held commercial real estate brokerages in the U.S. Since launching the firm in 2015, Kyle has scaled the company to nearly 30 offices and over 1,000 employees, closing more than $66 billion in transaction volume. Before his rise in business, Kyle played college football at USC under Pete Carroll, learning firsthand what it meant to be part of a high-performance team, lessons that deeply shaped his leadership style and company culture.Kyle opens up about the long, uncertain road of early entrepreneurship, including the 17 months he went without earning a single dollar in commission. He shares how the pain of regret from his football days shaped a new personal standard of work ethic and intensity in business. Kyle gets honest about what it really takes to succeed as a founder, the role of a supportive partner, why he front-loaded his life for freedom later, and how he's intentionally designed both business and family life to thrive. This conversation is packed with insights on scaling, sacrifice, and staying grounded.Chapters:03:51 – From Football Benchwarmer to Business Beast05:24 – Lessons From Team Sports That Shaped Leadership06:45 – The Regret That Still Fuels Kyle Today08:32 – Building a Career With No Plan B10:02 – How Waking Up at 4:45 Became a Competitive Advantage12:41 – 14-Hour Workdays for 10 Years Straight14:21 – 17 Months Without a Paycheck and Why He Didn't Quit18:33 – When Hard Work Didn’t Translate to Results, Yet20:15 – How Early Struggles Made His Boss's Job Harder21:10 – The Real Impact of Marrying Young24:48 – The Secret to Aligned Relationships While Scaling27:01 – Would He Be as Successful Without His Wife?31:41 – Designing His Life to Be Fully Present for His Kids33:17 – How NFL Players Actually Spend Their Time34:45 – His Dad's Role Model Blueprint for Fatherhood36:59 – Coaching His Son’s Football Team While Running a Company38:30 – Why Your 20s Shouldn’t Be Spent “Enjoying Life”40:00 – The Myth of Work-Life Balance42:02 – How Matthews™ Scaled From 15 People to 1,000+45:23 – Why Kyle Left a Public Company to Start His Own46:45 – The Business Model That Made Matthews™ Explode52:47 – Scaling as a CEO: From Founder to Strategic Leader54:36 – The Intuition Trap: When Founders Need to Let Go59:08 – What Kyle Would Tell His 33-Year-Old Self1:03:29 – Buying Matthews.com From a Basement-Dwelling Domain Squatter1:06:13 – Why You Must Choose Your Hard in LifeLinks:https://www.matthews.comIG: @kylematthewsceoLinkedIn: Kyle MatthewsYouTube: Kyle MatthewsPodcast: The Matthews Mentality PodcThe Founders Club: The premier community for founders pursuing excellence in the mind, body, and business.Stay Connected!Aaron Spivak:IG: @‌SpivakLinkedinThe Founders ClubIG: @‌TheFoundersClubWebsite www.foundersclubofficial.com Founder2Founder:TikTok @‌Founder2FounderPodcastYoutube @‌Founder2Founder.Podcast