Explore every episode of the podcast Founder2Founder with Aaron Spivak
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How Oleg Lee Built a $60M Manufacturing Business From a Family Garage
26 Nov 2025
00:53:31
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 Energy
Building a Company That Runs Without You: Kyle Matthews on Scaling Leadership at Matthews™
19 Nov 2025
01:10:31
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 Beast 05:24 – Lessons From Team Sports That Shaped Leadership 06:45 – The Regret That Still Fuels Kyle Today 08:32 – Building a Career With No Plan B 10:02 – How Waking Up at 4:45 Became a Competitive Advantage 12:41 – 14-Hour Workdays for 10 Years Straight 14:21 – 17 Months Without a Paycheck and Why He Didn't Quit 18:33 – When Hard Work Didn’t Translate to Results, Yet 20:15 – How Early Struggles Made His Boss's Job Harder 21:10 – The Real Impact of Marrying Young 24:48 – The Secret to Aligned Relationships While Scaling 27:01 – Would He Be as Successful Without His Wife? 31:41 – Designing His Life to Be Fully Present for His Kids 33:17 – How NFL Players Actually Spend Their Time 34:45 – His Dad's Role Model Blueprint for Fatherhood 36:59 – Coaching His Son’s Football Team While Running a Company 38:30 – Why Your 20s Shouldn’t Be Spent “Enjoying Life” 40:00 – The Myth of Work-Life Balance 42:02 – How Matthews™ Scaled From 15 People to 1,000+ 45:23 – Why Kyle Left a Public Company to Start His Own 46:45 – The Business Model That Made Matthews™ Explode 52:47 – Scaling as a CEO: From Founder to Strategic Leader 54:36 – The Intuition Trap: When Founders Need to Let Go 59:08 – What Kyle Would Tell His 33-Year-Old Self 1:03:29 – Buying Matthews.com From a Basement-Dwelling Domain Squatter 1:06:13 – Why You Must Choose Your Hard in Life
From 0 to 2,000+ Person Events: Lucy Nelles on Community, Profit, and Scale
10 Sep 2025
00:59:34
In this episode of Founder2Founder Aaron Spivak sits down with Lucy Nelles, leading community-building expert and co-founder of Coffee & Chill Miami, the wildly popular bi-weekly sober wellness party that now draws over 1,000 guests per event. With over 100 sold-out events and collaborations with top global brands, Lucy has cracked the code on making in-person gatherings profitable, scalable, and deeply impactful.
She shares how she went from feeling isolated in a new city to building a movement, and now teaches others to do the same through her program, Community Mastery. Listen in for insights on team structure, brand partnerships, pricing strategy, and how to build meaningful connections without alcohol.
Chapters: 02:14 – Introducing Lucy: From Isolation to Community 03:46 – The Move to Miami & Early Challenges 04:34 – The First Event That Sparked It All 05:10 – Ice Baths, Stock Tanks & the Rise of a Trend 06:59 – How Coffee & Chill Was Born 08:03 – Losing $10K on One Event (and What She Learned) 09:30 – The #1 Mistake Event Hosts Make 11:00 – The First Coffee & Chill: JBL Speakers & 250 Guests 12:38 – Gradually Raising Ticket Prices & Building Trust 13:57 – Driving Repeat Attendance Every Two Weeks 16:24 – Special Collaborations: Art Basel, F1, NFL 17:18 – How Lucy and Her Co-Founder Divide and Conquer 19:39 – Keeping a Healthy Co-Founder Relationship 21:06 – Investing in Learning for Herself and Her Team 24:28 – Launching Community Mastery to Serve Others 26:09 – Balancing Two Businesses Without Burnout 27:37 – Time-Blocking, Non-Negotiables, and Systems 30:26 – Expanding Coffee & Chill Into New Cities 31:45 – How to Stand Out in a “Saturated” Market 33:31 – Rethinking Nightlife: No Booze, All Wellness 38:54 – Why Lucy Quit Drinking and What Changed 43:07 – Overcoming Imposter Syndrome Through Results 45:45 – The Bigger Mission: Building In-Person Culture
From a $900 Bank Account to a $50M Brand: Chris Meade on Building CROSSNET
03 Sep 2025
01:11:16
In this episode of Founder2Founder, Aaron Spivak sits down with Chris Mead, co-founder of CROSSNET and Founders Club, for his most open and personal conversation to date. From a small Connecticut town, to building one of the fastest-growing backyard sports brands in America, Chris unpacks the highs, lows, and lessons of scaling a startup from scratch.
They dive into the origins of CROSSNET, the $1M mistake during an acquisition, the toll of leadership decisions, and how those experiences shaped the vision for Founders Club. If you’re navigating the founder journey, this episode is packed with the kind of honest insights you won’t get anywhere else.
Chapters: 02:49 – Growing Up in Small-Town Connecticut 04:40 – From Film School, to HBO, to Burnout 06:30 – Learning Amazon Dropshipping in College 08:26 – Fired, Broke, and Starting Over at Uber 12:49 – Inventing CROSSNET in a Backyard 15:06 – Quitting Jobs and Moving to Miami 17:49 – Going All-In with Marketing 19:21 – $87K to $9.8M: CROSSNET’s Hockey Stick Growth 21:30 – The Year Everything Went Wrong 25:19 – The Mistake of Not Cutting Fast Enough 28:10 – Trusting the Wrong CFO and Losing Sight 30:01 – The Acquisition That Fell Apart 33:50 – Picking the Wrong Buyer for the Wrong Reasons 35:10 – The Second Exit: Why Vivier Was the Right Fit 38:15 – What He’d Tell His Younger Self 42:04 – Why He Wouldn’t Change a Thing 42:46 – Building Founders Club from Scratch 46:41 – What Makes the Community Work 49:29 – There’s No Real Community for Founders… Until Now 51:07 – What a Great Member Looks Like 54:10 – Building a Life Beyond the Business 57:15 – Relationships Compound Like Capital 58:19 – Founders Forum and the Future of Events 1:00:51 – The Long-Term Vision for Founders Club 1:06:49 – Why This Will Never Be a Suit-and-Tie Club
The 3 Traits Every High-Growth Brand Shares, According to Shopify’s President Harley Finkelstein
27 Aug 2025
00:58:13
In this special episode of Founder2Founder, Aaron Spivak sits down with Harley Finkelstein, President of Shopify, for a no-fluff, behind-the-scenes conversation recorded live with over 100 Founders Club members. Harley unpacks the deep connection between personal identity and building lasting companies, while discussing how founders can grow smarter and why success demands unshakable character and long-term thinking.
This isn’t a surface-level chat, Harley dives into the psychological drivers behind great founders, how AI is changing hiring and operations, and why you should fire yourself before it’s too late. He shares tactical insights on platform strategy, what Shopify looks for in celebrity-led brands, and how to build a company that’s authentic, resilient, and scalable. From DJing at 13, to leading one of the most iconic tech companies globally, Harley’s founder journey is packed with clarity and conviction that every entrepreneur can learn from.
Chapters: 01:28 – Balancing Personal Brand vs. Business Brand 06:49 – Why Founders Must Go Direct (and Skip Legacy Media) 07:27 – 3 Traits of the Most Successful Brands 12:45 – How AI is Replacing Full-Time Roles at Shopify 14:20 – Growing Firebelly Tea with Fewer People and More Energy 15:47 – Hire Founders, Not Résumés 17:44 – Why Shopify is Run by Founders (and How That Works) 19:06 – Harley’s Grandfather & Building with Character 23:49 – Work-Life Integration & Founders in Relationships 28:11 – Daily Habits, Self-Awareness & Why Harley Meditates 31:29 – The Only Meetings Harley Never Misses 34:38 – When Shopify Builds In-House vs. Letting Apps Thrive 40:35 – What Business Are You Really In? Harley Coaches a Founder Live 46:12 – How to Stop Losing DTC Sales to Amazon 50:01 – Why It Doesn’t Matter Where the Sale Happens 50:44 – Shopify’s Celebrity Strategy (It’s Not About Fame) 55:50 – Harley’s Final Ask: Help a Founder IPO
From $2,500 in Debt, to the World's Finest Tea Brand: Steve Schwartz on Building Art of Tea
20 Aug 2025
01:19:30
In this episode of Founder2Founder, Aaron Spivak sits down with Steve Schwartz, Master Tea Blender, best-selling author, and founder of Art of Tea—an award-winning tea brand based in Los Angeles. After dropping out of college to care for his mother, Steve discovered Ayurvedic medicine and began a journey that would take him across the globe sourcing and blending the world’s finest teas.
Starting with $2,500 in credit card debt, Steve built a vertically integrated company that now supplies iconic restaurants and hotels. He shares how he turned tragedy into purpose, created the U.S.’s first tea sommelier role, and built a legacy-focused business with intention and heart.
Chapters: 02:32 – Losing His Mother and the Awakening of Purpose 04:11 – Discovering Ayurveda and the Art of Botanical Blending 06:23 – The Truth About Supermarket Tea 07:12 – The Power of Ritual: Why Tea Is Not Just a Beverage 08:52 – Choosing Steady Growth Over the Hockey Stick 11:03 – Building with a Multi-Generational Vision 12:35 – American Flips vs. Eastern Longevity Thinking 14:40 – Why Art of Tea Avoids Supermarkets 16:03 – Creating the First Tea Sommelier Position in the U.S. 17:22 – Expanding Art of Tea to the East Coast 19:13 – Controlling Quality Through Vertical Integration 21:16 – Coaching vs. Babysitting: Leadership Lessons 22:12 – The Daily Work of Unlearning Scarcity 25:37 – Childhood Scarcity and the Roots of Limiting Beliefs 28:08 – From Rabbi Aspirations to Global Tea Advocate 30:00 – Smiling as Strategy 33:14 – The Power of Giving Before You Receive 36:44 – Parenting, Abundance, and Entrepreneurial Mindsets 39:58 – Why Entrepreneurship Is the Best Way to Live 43:30 – Creating Safe Spaces for Founders to Be Real 45:29 – Betting on Himself With a Baby on the Way 47:09 – Filling an Org Chart by Removing Himself 50:11 – DJ Fails and the Power of Vulnerability 53:01 – The Real Reason People Join Founder’s Club 54:06 – Building Grit in the Next Generation 55:46 – One Day a Week Off: Shabbat as a Business Advantage 57:12 – What His Late Mother Would Say Now 59:14 – A Message to His 20-Year-Old Self 1:00:33 – The Power of Trust Over Fear 1:03:19 – What He Wants to Be Remembered For 1:05:53 – Getting Out of Your Own Way 1:07:20 – What’s Actually Going On With Matcha 1:11:39 – Matcha Sourcing Crisis and the Japan Trip That Changed It 1:13:55 – The Matcha Trend Explained 1:18:06 – Closing Reflections on Legacy and Leadership
From $10 in the Bank to a $9M Beverage Brand: Megan Klein’s Unconventional Path with Little Saints
13 Aug 2025
01:26:19
In this episode of Founder2Founder, Aaron Spivak sits down with Megan Klein, founder of Little Saints, the sugar-free, mushroom-powered non-alcoholic cocktails and spirits brand redefining the way we drink. A former environmental attorney turned two-time brand founder, Megan’s journey is one of radical pivots, personal reinvention, and unshakable self-belief. She shares how she went from shutting down her first startup to investing her last million, selling her own apartment to fund it, and scaling Little Saints to $9.6M in revenue without traditional VC backing.
Megan opens up about her lowest moments, from navigating loneliness during the pandemic, to hitting $10 in her personal bank account, and the turning point that came from trusting her own intuition over outside “expert” advice. She dives into how plant medicine shaped her leadership style, the hard lessons of Shark Tank, and why aligning brand growth with personal growth has been the foundation of her success. This is an unfiltered conversation on grit, discernment, and building a category-defining CPG brand on your own terms.
Chapters: 02:21 – From Lawyer to Rooftop Farming 04:51 – The Fog of Misalignment in Corporate Life 07:41 – Equity-Only Hustle at Farmed Here 08:22 – Building The Fresh Factory from a Failed Startup 11:42 – Fundraising Lessons from the First Business 12:35 – Investing Her Own $1M to Start Little Saints 14:37 – The Solo Founder Reality During the Pandemic 16:42 – Hemp Silk Cocktail Masks: The First Little Saints Product 18:05 – The Dry January Experiment That Sparked the Brand 21:00 – Discovering Ayahuasca and Plant Medicine’s Impact 28:55 – Quitting Alcohol for Good 32:39 – Going All-In with DTC 36:09 – Selling Assets to Save the Business 39:50 – Crisis Summer: Cancellation, Family Emergency, and Cash Shortage 41:06 – Unlearning the Need for Outside Approval 46:57 – Filming Shark Tank and Walking Away from the Deal 51:01 – Scaling from $100K to $9.6M in Three Years 53:17 – Laying the Foundation for $20M+ Growth 56:53 – Using Plant Medicine to Become a Better Leader 59:08 – Radical Feedback from the Team 1:03:26 – Little Saints Dirty Martini Demo 1:07:20 – Building in Miami and Creating the Little Saints House 1:11:32 – In-Person vs. Remote Team Dynamics 1:13:08 – What December 2020 Megan Would Be Most Proud Of 1:16:03 – Message to a 16-Year-Old Megan 1:18:39 – Blending Personal Development with Business Growth 1:21:31 – Choosing Alignment Over Short-Term Gains 1:22:23 – Where to Buy Little Saints
The Future Will Be Built by Founders Who Understand AI—Mark Cuban on How to Stay Ahead
06 Aug 2025
00:58:33
In this special episode of Founder2Founder, Aaron Spivak brings you an unfiltered masterclass with legendary entrepreneur and investor, Mark Cuban. Recorded live for members of The Founders Club, this exclusive session covers Cuban's raw insights on building billion-dollar companies, the unglamorous truths of scaling, and how AI is rewriting the rules for modern founders. From sleeping on floors to exiting for $5.7 billion, Cuban reflects on his journey and the mindsets that separate the winners from everyone else.
Mark doesn’t hold back; he dives into why founders should stop glamorizing fundraising, how sales always win over hype, and the one habit that will leave your competition behind. He shares honest perspectives on balancing relationships and business, the brutal reality of hiring the wrong CEO, and how to futureproof your company in the age of AI. Whether you’re bootstrapping or scaling fast, this episode is packed with tactical clarity and real founder-to-founder advice.
Chapters: 01:40 – Why Personal Brands Are Overrated 03:15 – The One Trait All Successful Founders Share 05:45 – Sales First, Always 07:40 – Raising Capital Is Not an Accomplishment 09:34 – Work-Life Balance? Wait Until You're Winning 12:20 – How AI Is Changing the Game (and Why You Can’t Delegate It) 15:00 – How Founders Should Be Learning AI Right Now 17:15 – When to Sell (Even If You're Loving the Business) 20:00 – Why College Accreditation Is Fundamentally Broken 22:00 – What’s Next for Higher Education in an AI World 24:00 – Why You Should Think Twice Before Publishing Anything 25:55 – Should You Hold Back Expansion When Prepping for Exit? 27:40 – Launching Into Sports Partnerships the Smart Way 29:45 – Niche Product? Why You Should Be More Expensive 32:10 – When It’s Time to Hire an External CEO 34:30 – How Mark Leverages ChatGPT in Real Business Decisions 36:20 – Fundraising in a Tough Market: Take the Money or Bridge? 39:00 – Handling Tariffs and Scaling Beyond Local Markets 41:00 – One Simple Daily Habit That Pays Big Mental Returns 44:55 – Should You Expand Your Product Line or Focus Deeper? 47:15 – Promoting Internally vs Hiring for Scale 49:45 – Equity Strategy: What’s Too Much, What’s Too Little 52:30 – The Belief Cuban Had to Unlearn About Leadership 54:50 – "Don’t Be a-”: A Founding Principle That Pays 55:45 – What Every Founder Needs to Learn About Healthcare Costs 57:15 – Mark’s Final Word: Keep Showing Up
Larysa Nakonecznyj: She Walked Away From Law School, Then Built a Top Global Agency
30 Jul 2025
01:07:44
In this episode of Founder2Founder, Aaron Spivak sits down with Larysa Nakonecznyj, CEO of Nako Creative, an award-winning digital marketing agency known for driving measurable results through innovation and tailored strategy. With a background in communications and advertising, Larysa has helped global brands grow fast and grow smart. She’s been recognized with the 2024 Global Recognition Award and was nominated for the Women Empowerment Foundation’s “Rising Star” award.
Larysa unpacks the exact moment her path shifted after a single shift waiting tables, and how she walked away from law school to build something of her own. She shares the story behind her first pitch, scaling too fast, bouncing back from burnout, and the mindset work that’s kept her going. This conversation is a powerful look at what it takes to build a solo agency to seven figures while staying grounded in vision and values.
Chapters: 01:40 – Realizing She Wasn’t Meant to Work for Anyone 03:23 – First Corporate Job & Red Flags 04:59 – The Shift at The Keg That Changed Everything 06:12 – Pitching an Agency She Hadn’t Built Yet 07:33 – The Woman Who Believed in Her First 08:33 – Faking a Florida Trip to Buy Time 09:38 – Where Her Standard for Excellence Comes From 11:29 – Walking Away From Law School 12:57 – Breaking the News to a Traditional Family 14:10 – Seeing Opportunity Everywhere 15:59 – Manifesting Confidence Before the Pod 17:44 – Prepping for the Next Hour, Always 19:15 – Discovering “The Secret” and Shifting Mindset 22:54 – When Scaling Too Fast Breaks the System 24:46 – Burnout and Questioning It All 26:14 – Almost Going Back to School 28:14 – Saying No Becomes the New Strategy 30:01 – Doing It Alone Without a Co-Founder 32:08 – From Doubting to Betting on Herself 33:47 – Building Confidence Through Results 35:29 – Curating a Circle That Believes In You 37:54 – Two Types of Friends (Choose Wisely) 39:17 – Life After Exit and the Power of Community 41:54 – The Mental Weight of Being a Young CEO 44:54 – “Move With Confidence”, The One Conversation That Shifted Everything 46:54 – Building Systems Through Mistakes 48:08 – Why Most Agencies Don’t Work Hard Enough 50:18 – The Ferrari x Art Basel Win 52:59 – The Internal Team Mentality Clients Love 55:20 – Advice to Her 20-Year-Old Self 56:13 – Designing a Business Around the Life She Wants 59:35 – Naivety Can Be a Superpower 1:01:09 – The Truth About Building a Business 1:04:31 – Retention as the Ultimate KPI 1:05:32 – Final Word: Show Up, Work Hard, Win!
Two Exits Before 20: What Austin Copeland Knows About Building, Leading & Letting Go
23 Jul 2025
01:08:18
In this episode of Founder2Founder, Aaron Spivak is joined by Austin Copeland—a 21-year-old founder who’s already built and sold two companies, including COMPREADY, acquired by CosmicWire. From founding a nonprofit at 13 that delivered over 13,000 shoes to kids in Africa, to managing a 25-person team at global esports giant TSM, Austin’s journey is driven by one mission: improving people’s lives.
He unpacks how he went from gaming enthusiast to building an analytics model that led to six-figure player buyouts, what it takes to stay true to yourself in high-pressure environments, and why being surrounded by the right people can accelerate everything. Now overseeing COMPREADY under CosmicWire, Austin is focused on optimizing computer performance at scale—all while continuing to grow into the entrepreneur he was built to be.
Chapters:
02:24 – A Childhood Immersed in Business 03:40 – First Taste of Entrepreneurship: Beachside Hustles 04:51 – Flipping Burgers at 13: Real-World Lessons 06:03 – Rejecting the “Right Path” and Going His Own Way 07:51 – Selling His First Business at 19 08:03 – Gaming as Passion and Profit 09:29 – Building a Data-Driven Talent Engine 11:30 – COVID’s Influence and Seizing Opportunity 13:28 – The First Exit: Acquired at 16 14:17 – Earning $80K and Managing 25 People 15:43 – The Spark Behind COMPREADY 17:19 – Leaving a Safe Role to Build Again 18:46 – Sacrifice and Identity in the Startup Grind 20:22 – Going All In at 18 22:35 – Choosing College Amid Success 24:37 – The Moment He Knew It Was Real 25:50 – Exit #2: COMPREADY Acquired by CosmicWire 27:03 – Leadership Mistakes and Learning the Hard Way 28:40 – Not Everyone Has Your Fire 30:13 – Making Decisions Through Noise 31:27 – Becoming Unapologetically Himself 33:46 – Vision for 30 and Long-Term Fulfillment 35:45 – The Mentors Who Changed the Game 38:41 – “It’s OK”: How Reassurance Moves Founders Forward 42:44 – Experience Over Theory, Every Time 45:50 – Giving First and Building Reputation 47:11 – Manifesting the Jet and What It Represents 50:59 – Freedom, Frustration, and Fuel 52:04 – You’re Only Out When You’re Dead 54:25 – Don’t Judge What You Haven’t Tried 56:39 – Volunteering to Learn and Grow 58:22 – Advice to His 15-Year-Old Self 1:03:29 – Life in Reverse: Start From the End 1:04:49 – Your Environment Won’t Always Grow With You 1:06:28 – The Power of Being Good Energy
Swan Sit on The Future of Belonging: Defining a New Era By Building Real Community in a Disconnected World
16 Jul 2025
01:30:06
In this episode of Founder2Founder, Aaron Spivak sits down with Swan Sit, a trailblazing operator and creator at the intersection of corporate leadership, digital transformation, and consumer connection. With an impressive background as the Global Head of Digital Marketing at Nike, Revlon, and Estée Lauder, Swan now advises startups, sits on public company boards, and brings value to millions as a creator and speaker.
Swan shares her journey from a disciplined immigrant upbringing to transforming some of the world’s most iconic brands. She opens up about navigating the dot-com crash, pivoting into the creator economy through Clubhouse, and ultimately discovering her purpose: democratizing access, information, and opportunity. This is a rich conversation on resilience, relevance, and redefining success on your own terms.
Chapters: 03:06 – Immigrant Upbringing and Early Discipline 05:35 – Childhood Dreams and Retail Tech Fascination 07:37 – Going Against the Grain: Startup Over Goldman 10:57 – Dot-Com Crash, Layoffs, and Lessons Learned 12:58 – Study Abroad and Breaking From Family Influence 15:24 – Finding Self Through Distance and Travel 17:27 – Product Marketing, Emotional Branding, and Grad School 21:18 – Joining Estee Lauder and Building Early E-Com 22:05 – Leading Digital at Revlon and Nike 23:57 – Navigating Change: Why Adaptability Wins 25:49 – Making AI Useful Without Getting Lost in It 28:43 – Personalized Content and the Future of Storytelling 31:58 – Using Social Graphs to Build Digital Communities 34:52 – NFTs, Ownership, and Reframing Value 37:29 – Clubhouse Origins: Mentorship and Scale 41:44 – Creator vs. Influencer: Making Real Impact 47:19 – Defining Purpose: Access, Information, and Equity 50:39 – Family, Scarcity, and Quiet Generosity 54:14 – Rest as a Strategy: Recharging for Performance 57:36 – Public Speaking: From Corporate to Global Stages 1:00:13 – Live Speaking Tips: Energy, Feedback, and Q&A 1:02:37 – From Corporate Leader to Founder Mindset 1:05:31 – Reading the Room: Intuition and Audience Engagement 1:10:21 – Where Empathy Comes From 1:13:45 – Identity, Belonging, and Owning Your Story 1:17:49 – Advice to Her Younger Self: “Go Be Your Freak Self” 1:21:22 – Detaching Worth From Titles and Roles 1:23:13 – Legacy, Impact, and Reversing Into Purpose
The Realest Founder Story Yet: No English, No Money, and 5 Kids- Here’s How Rachel Spivak Did It
09 Jul 2025
01:26:43
In this episode of Founder2Founder, Aaron Spivak sits down with his own mother, Rachel Spivak, for an intimate and powerful conversation that spans generations, continents, and entrepreneurial journeys. Born in the small Israeli town of Ofakim as one of 13 siblings, Rachel shares her story of resilience, ambition, and unwavering love for her family. From leaving her home at age 13 to go off to school, to raising five boys in Canada, her life is a testament to grit, sacrifice, and entrepreneurial instinct.
Rachel recounts building a new life in Canada with no job, no English, and three kids under three, eventually launching multiple businesses, including a successful care agency and retail ventures. She opens up about losing everything overnight, rebuilding from scratch, and instilling entrepreneurial values in her children, all of whom became business owners. Rachel offers timeless wisdom on parenting, perseverance, and how to build a meaningful life from the ground up.
Chapters: 01:20 – Growing Up in Ofakim With 13 Siblings 04:13 – Childhood Lessons in Strength 05:13 – “Don’t Be Afraid of Fear” – A Life Mantra 07:12 – Leaving Home at 13 for a Different Life 14:01 – Moving to Canada With Three Young Children 15:52 – Starting Over Without English or a Job 21:03 – Building Businesses From Scratch 24:15 – Cleaning Houses and Driving a School Bus to Survive 27:56 – From House Cleaner to Care Agency Owner 30:42 – Losing a Business Overnight, Starting Again With Jewelry Sales 33:02 – Teaching Her Kids To Build and Rebuild 36:30 – Leading By Example: The Power of Silent Sacrifice 39:27 – Parenting Wisdom for the Modern Generation 41:55 – Encouraging Entrepreneurship From a Young Age 44:34 – Working Through Setbacks and Always Showing Up 46:49 – Why She’s a Mom, Not a Friend 49:11 – Raising Five Boys and Navigating Marriage, Business, and Life 53:52 – How Many Kids Should People Have Today? 56:37 – Parenting Without Complaints, Even in the Digital Age 1:00:22 – Still Working: Showing Up at Early to Lead By Example 1:03:56 – Working With Family: The Greatest Challenge 1:05:44 – Family Unity Above All: Why Fighting Was Never an Option 1:11:06 – Dealing With Distance: Moving to Miami and Family Bonds 1:20:00 – What Rachel Would Tell Her 18-Year-Old Self 1:24:47 – Her New Mission: Creating Memories With Her Grandkids
Quitting a 17-Year Corporate Career to Launch a Brand: Natia Ramishvili on Rebuilding From Zero
12 Nov 2025
00:56:12
In this episode of Founder2Founder, Aaron Spivak sits down with Natia Ramishvili, entrepreneur, empowerment coach, and founder of NR Active. Born in the country of Georgia, Natia immigrated to the U.S. as a teenager and built a thriving 17-year career in finance, ultimately overseeing more than 1,000 employees. But after experiencing deep personal loss, a divorce, and a powerful shift in purpose, she left her executive role, moved to Miami, and launched a brand rooted in authenticity and empowerment.
Natia shares how the pain of losing her parents shaped her drive, what it really took to walk away from stability, and how she’s now helping women reconnect with their strength through fashion, mindset, and community. She opens up about creating NR Active, building a fearless brand from scratch, and why confidence is something you create, not something you wait to find. From single motherhood to brand building, Natia’s story is a testament to resilience, intentional living, and owning your worth.
Chapters 02:17 – Losing Both Parents and Finding New Purpose 04:22 – Dreaming Bigger at Macy’s and Building a Career in Finance 05:48 – The Role of Authenticity in Rebuilding a Life 06:36 – Defining Fearlessness Through Action 07:40 – The Catalyst: Losing Her Mother to Cancer 09:55 – Leaving Marriage and Career to Start Fresh 10:55 – Embracing the Unknown and Trusting Intuition 12:09 – From People Pleasing to Self-Prioritization 13:33 – Funding NR Active with Her Life Savings 14:32 – “Burn the Boats” and Commit All In 16:25 – Building a Brand With Vision and Discipline 18:57 – Why Chemical-Free Activewear Matters 20:42 – The Message Behind the Apparel: Wear Your Strength 22:45 – The Birth of Born For More Coaching 25:49 – The Reality of Doing It All as a Single Mom 27:44 – Staying Grounded With Routine and Self-Work 28:21 – Book Recommendations That Changed Her Thinking 29:45 – A Lesson From Her Parents: You Can Do Anything 31:18 – Overcoming Doubt With Relentless Action 33:13 – Being Called “Crazy” for Choosing Reinvention 36:32 – The Truth About Rejection and Redirection 38:53 – The Power of a Supportive Partner| 39:58 – The Long-Term Vision for NR Active 42:19 – Money Buys Freedom, Not Fulfillment 47:05 – Advice for Single Mothers Building a Business 49:18 – What She’d Tell Her 5-Year-Old Self
How Integrity, Grit, and Real Estate Deals Built Mark Shapiro's Legacy
02 Jul 2025
01:30:06
In this episode of Founder2Founder, Aaron Spivak speaks with Mark Shapiro, founder of Shapiro Capital, a seasoned real estate investor with over four decades of experience. Mark shares his journey from selling gum in elementary school to building a multimillion-dollar real estate empire. He offers valuable insights into the mindset, drive, and strategies that led him to success, as well as the lessons learned from both his victories and setbacks.
Mark delves into his early real estate experiences, creative financing tactics, and the importance of simplicity and discipline in both business and life. His approach to mentoring others, navigating personal struggles, and focusing on authentic relationships is a powerful example of how real success is built over time.
Chapters: 00:00 – Mark’s Entrepreneurial Spark In Elementary School 04:00 – Early Lessons From The Family Business 07:40 – Snowblowing Driveways And Learning Value 10:47 – The Influence Of Mark’s Father 13:28 – First Business Deal With His Dad At 23 18:06 – Overcoming Personal Loss And Finding Purpose 22:51 – Discovering Real Estate Through Family And Books 25:42 – Scaling Early: From College Deals To 58 Units 38:22 – Addiction To The Chase: Why Mark Loves The Game 43:20 – Taking Big Risks At 26 And The $3M Payday 49:16 – How Success Complicated Personal Life 54:20 – The Wisdom Of Grinding It Out 58:33 – Life Lessons On Margin, Simplicity, And Consistency 1:04:06 – Teaching Real Estate: Building A High-Touch Mentorship Model 1:06:42 – Lydia’s Journey: 0 To 24 Units In A Year 1:08:57 – From Scratch: Helping Beginners Get Their First Deal 1:13:48 – For Founders With Capital: How To Start In Real Estate 1:16:39 – The Power Of Community And High-Touch Guidance 1:22:00 – Reflecting On Regrets And Legacy 1:28:12 – Living With Integrity And Spiritual Anchors
Shelby Sapp Didn’t Just Break Into Sales, She Rebuilt It For Women Everywhere
25 Jun 2025
01:15:20
In this episode of Founder2Founder, Aaron Spivak sits down with Shelby Sapp, the founder of She Sells Academy, the world’s largest all-women remote sales academy. After beginning her career in door-to-door pest control sales, Shelby realized traditional sales models weren’t built for women or the lifestyle they wanted. With She Sells, she’s built a community of over 3,000 women mastering high-ticket remote sales, unlocking financial independence and freedom along the way.
Shelby discusses her journey from figure skater to powerhouse sales trainer, the critical role of mindset and visualization in success, and how her mother and grandfather influenced her fiercely independent drive. She shares candid reflections on building her business, dealing with imposter syndrome and online hate, and the nuances of masculine and feminine dynamics in both sales and relationships. Shelby’s story is a powerful example of how vision, grit, and being a “calculated psychopath” can not only change your own life, but the ripple effect of others.
Chapters 00:00 – Shelby’s Sales Origin Story 02:55 – Discovering Remote Sales As A “Cheat Code” 03:26 – Mindset, Manifestation, And The Impact Of Figure Skating 06:13 – Growing Up With A Hardworking Single Mom 07:35 – Living The Life She Once Dreamed 08:53 – Proving Herself In Male-Dominated Sales Teams 10:53 – Who Joins She Sells And Why 13:09 – Selling What You Believe In 15:56 – Helping Women Find Financial Independence 17:26 – Who Supports The Leader 20:53 – Navigating Friendships During Rapid Growth 25:03 – The Early Vision That Sparked She Sells 30:14 – Balancing Masculine Energy In Business And Relationships 34:18 – Should Salespeople Seek Equity? 36:22 – Dealing With Online Hate 41:56 – Do Women Perform Better In Sales? 44:14 – The Nuances Of Women Selling To Women 45:43 – Staying Authentic As A Founder 48:34 – What Shelby Wants To Be Remembered For 51:15 – The Legacy Of Her Grandfather 56:23 – Loving Pressure And Building Through It 57:44 – Embracing Being “Delulu” As an Entrepreneur 1:01:19 – Clarity In Vision And Decision-Making 1:06:22 – Adjusting To Success And A New Lifestyle 1:09:24 – How Shelby Manages Her Money 1:11:45 – Final Message: Be A Calculated Psychopath 1:13:13 – The Power Of Belief And Presence
From Selling Shaved Ice to Scaling a National Food Empire with Gaston Becherano
18 Jun 2025
01:04:30
In this episode of Founder2Founder, Aaron Spivak sits down with Gaston Becherano Cohen, CEO of Smorgasburg—the largest weekly open-air food market in the U.S. Gaston shares how a solo trip to Japan reignited his entrepreneurial drive and ultimately led him from shaved ice vendor to acquiring the entire Smorgasburg brand. His journey includes launching, and losing, a café during COVID, starting over in Miami, and building markets that now draw millions of visitors.
He speaks candidly about scaling with lean teams, trusting his instincts, and launching his Japanese tea brand, Motorcycle Matcha. This conversation dives deep into the mindset, resilience, and strategic pivots behind building a cultural institution rooted in food, community, and creativity. Subscribe, share with a fellow founder, and leave a review if this episode resonated with you!
Chapters: 02:56 – Leaving IBM: Realizing He Wasn’t Built for Corporate Life| 03:54 – A Solo Trip to Japan That Changed His Trajectory 04:26 – Discovering Hospitality as His Lane 08:58 – Getting Accepted as a Shaved Ice Vendor in Brooklyn 09:49 – Launching Bonsai Café and Learning the Business 11:24 – COVID Hits: Closing the Café and Moving Back to Miami 14:00 – Starting Over with a Farmers Market in Aventura 18:48 – Seeing the Vision for Smorgasburg Miami 20:05 – Convincing the Landlords and Licensing the Brand 22:25 – The Grueling Process of Getting Permits Approved 24:56 – Opening Day in Wynwood: 15,000 Attendees and Flying Tents 27:38 – Sustaining Demand Week After Week 28:20 – Acquiring the Entire Smorgasburg Brand 30:51 – Reframing Entrepreneurship as a “Grand Adventure” 32:01 – Building Motorcycle Matcha in the Japanese Countryside 34:00 – Sourcing, Storytelling, and Building a Passion-Driven Brand 36:17 – Growing Up in a Tight-Knit, Entrepreneurial Community 38:40 – “Entrepreneurship Is Like Riding a Motorcycle” 41:15 – Gaston’s Vision for Smorgasburg as a National Incubator 43:58 – The Emotional Cost of Growth and Staying Positive 45:57 – Detaching From the Rollercoaster of Business 48:30 – Running Lean: 16 Full-Time Staff, Millions of Visitors 49:51 – Leadership Through Empowerment and Humility 51:50 – Advice to Younger Gaston: Enjoy the Ride 58:45 – The Magic of Type 2 Fun in Entrepreneurship 1:00:09 – Final Words: Start Young, Start Naive, Start Now
Rejection, Sexism, and 100 Investor No’s: How Rajia Abdelaziz Still Raised $500K and Changed an Industry
11 Jun 2025
01:12:43
In this episode of Founder2Founder, Aaron Spivak sits down with Rajia Abdelaziz, Founder & CEO of invisaWear—a groundbreaking company creating discreet safety tech inside stylish jewelry. A Forbes 30 Under 30 cover honoree and a standout in the personal safety space, Rajia has built an eight-figure brand, raised over $3 million, and secured major partnerships with ADT and TELUS.
Rajia shares how she turned down a job at Google to pursue a college project that would go on to save lives. She opens up about facing rejection, fundraising setbacks, and personal sacrifice, all while building a mission-driven brand from the ground up. From a 3D-printed prototype built by her 14-year-old brother to a product that’s now sold nationwide, this episode is a powerful look at purpose, perseverance, and building with impact. Subscribe, share with a fellow founder, and leave a review if this episode resonated with you!
Chapters: 02:11 – Rajia’s first taste of entrepreneurship at 8 years old. 04:26 – Childhood hustle and early business ideas. 06:18 – Dreaming of an ice cream empire at 16. 07:57 – Growing up in a one-bedroom apartment and chasing the American Dream. 09:58 – The pressure to be perfect and the cost of high expectations. 11:32 – Choosing engineering and learning to build apps. 13:25 – The incident that sparked the idea for invisaWear. 16:02 – Launching invisaWear as a college project. 19:29 – Turning down Google and betting on a mission. 22:12 – Convincing her family to support her startup journey. 25:05 – Building with her co-founder Ray. 27:14 – A woman at demo day validates the mission. 28:56 – Handwritten thank-you notes from survivors. 30:42 – Sacrificing her 20s to build a mission-driven brand. 34:08 – Facing sexism and ageism in early fundraising. 35:30 – 14-year-old brother’s 3D print closes their first round. 39:45 – National news story puts invisaWear on the map. 43:00 – A health scare forces a mindset reset. 48:10 – 10 years of co-founder chemistry with Ray. 59:41 – What Rajia wants to be remembered for. 1:02:37 – Advice to her 21-year-old self. 1:04:52 – Rajia’s 5-year and 10-year vision.
Making 250k in 10 Days With No Product: How Jason Wong Figured "It" Out
28 May 2025
01:00:54
In this episode of Founder2Founder, Aaron Spivak sits down with Jason Wong, founder of Paking Duck, a packaging company trusted by leading DTC brands like Arrae, Quest Nutrition, and Madhappy. Jason shares his journey from a teenager running affiliate blogs and viral meme businesses, to building a powerhouse in the packaging space, blending creativity with operational excellence.
Jason dives into how packaging became his passion, why it’s one of the highest-leverage parts of the customer journey, and how investing in people has helped him scale multiple businesses. He also opens up about building confidence through action, earning trust through execution, and how one key mentor changed his entire trajectory. Tune in to hear Jason’s powerful insights on brand-building, mentorship, and executing with speed. Subscribe, share with a fellow founder, and leave a review if this episode resonated with you.
Chapters: 01:36 – Meet Jason Wong 02:53 – How Jason fell in love with packaging 03:57 – What top CPG brands get right 05:01 – Growing up: immigrant hustle and early ambition 06:19 – Starting a blog and making $30K/month in high school 08:04 – The viral launch of the Holy Meme Bible 09:25 – Transitioning to a product business 11:47 – Launching Doe Lashes with $500 13:11 – Building with friends and early team culture 14:17 – Growing up without parents and living in a garage 15:35 – Why Jason never gave up 16:36 – Raising your ceiling through community 18:18 – Sacrifices and discipline in the early years 20:16 – Entrepreneurship and relationships 22:08 – Becoming secure in your identity 24:49 – Creating your own luck through exposure 26:36 – Meeting Michelle Phan and her mentorship 29:42 – The power of sharing stories and giving back 31:07 – Jason’s philosophy on packaging and unboxing 34:09 – Most impressive packaging Jason has seen 37:44 – 3 ways packaging makes money 41:08 – Why packaging is part of the product 42:14 – Defining success and freedom 46:16 – Achieving milestones through material rewards 47:21 – Building multiple businesses through people 50:53 – Jason’s story of finding a superstar on Upwork 53:48 – A masterclass in relationship-driven leadership 56:46 – Advice to his 23-year-old self 58:00 – Just go do it — the power of action
Kevin O’Leary’s Advice on Mastering Focus and Scaling Faster
21 May 2025
00:20:22
In this episode of Founder2Founder, Chris Meade sits down with Kevin O'Leary, a successful entrepreneur and investor also known as "Mr. Wonderful”, appearing on shows such as Dragons' Den and Shark Tank. Kevin dives into the current landscape of advertising, explaining why he's pivoting his portfolio companies towards television through his new platform, WonderAds. He breaks down how TV has become a powerful yet under-utilized channel for brands looking to scale cost-effectively, offering a competitive edge over rising social media costs.
Kevin also discusses the critical components of successful brand scaling, the importance of mastering Customer Acquisition Cost (CAC), and why multi-channel strategies are essential for long-term growth. He closes with valuable insights on entrepreneurship, including how to prioritize signal over noise, the art of listening, and the necessity of knowing when to pivot. Join Chris and Kevin as they uncover the strategies behind building resilient brands, leveraging television for growth, and the key principles every entrepreneur should know. Don’t forget to subscribe, share with a fellow founder, and leave a review if you enjoyed this episode.
Chapters: 01:40 – Why TV Advertising is Making a Comeback 02:48 – Introducing WonderAds: TV for Emerging Brands 03:34 – Measuring Success on TV: CAC and ROAS 04:02 – Why Brands Give Up on TV Too Early 04:27 – Television’s Cost Efficiency vs. Social Media 04:52 – Mastering Customer Acquisition Costs 05:58 – The Importance of Personal Branding for Founders 07:08 – Building for Both Retail and Direct-to-Consumer 08:19 – Retail Rollouts: How to Secure and Succeed 10:35 – Signal vs. Noise: How to Focus Your Time 13:33 – The Art of Pivoting When Things Go Wrong 14:06 – Planning Liquidity Events and Exits 15:06 – Industries Ripe for Disruption: Healthy Snacks and Beverages 15:52 – Kevin’s Background in Photography and Film 16:52 – Embracing Discomfort: Why Founders Should Take Risks 17:39 – Lessons from Kevin's Mother: Integrity and Trust
The Relentless Drive to Win: How IQBAR Was Built One Chapter at a Time with Will Nitze
14 May 2025
01:43:00
In this episode of Founder2Founder, Aaron Spivak sits down with Will Nitze, Founder & CEO of IQBAR, the leading brain-and-body nutrition startup in America. Will shares how his competitive spirit and obsession with winning drove him to build a thriving brand dedicated to brain food and cognitive nutrition. He reflects on his journey from playing competitive sports to attending Harvard, where he first realized that building something impactful was more important than just making money.
Will also discusses launching IQBAR through a successful Kickstarter campaign, scaling with major retailers, and maintaining a lean, efficient team. He opens up about running the business alongside his wife, the importance of horizontal mentorship, and how he plans to build for acquisition and legacy.
Chapters: 00:44 – The Opportunist Mindset: Learning from Sam Zell 03:06 – Building the Competitive Spirit Through Sports 08:26 – Harvard Experience and Finding Direction 12:25 – First Steps into Entrepreneurship 14:02 – Negotiating Half-Time Work for Full-Time Hustle 15:21 – Starting IQBAR: Building Brain Food from Scratch 19:31 – Kickstarter Strategies: Guerrilla Tactics and Validation 22:01 – Manufacturing at Scale and Finding Co-Packers 24:38 – The Importance of Horizontal Mentorship 27:46 – Scaling the Business with a Lean Team 30:25 – Expanding into Major Retailers and Hitting Volume 33:43 – Navigating Trends and Pivoting the Brand 36:40 – Maintaining Control While Scaling Fast 38:29 – Hiring the Right People and the Hub-and-Spoke Model 41:06 – Working In the Business, Not Just On It 46:40 – Running a Business with His Wife 49:05 – Moving to Miami and the Evolution of IQBAR 52:13 – Building for Acquisition and Legacy 1:06:01 – Overcoming Challenges: Tariffs, COVID, and Market Shifts 1:07:50 - Building a Personal Brand 1:11:04 - The ROI of Personal Branding 1:25:10 - The Emotional Impact of Exiting a Business 1:31:11 - The Role of Partnerships in Business Success 1:34:46 - Advice for Younger Entrepreneurs
Tune in to hear Will’s raw insights on scaling a consumer brand from the ground up, the sacrifices required, and the mindset needed to build something that lasts. Don't forget to subscribe, share with a fellow founder, and leave a review if you enjoyed this episode.
Built in Her Memory: How Losing His Sister Redefined Josh Goldstein's Life, Business, and Legacy
07 May 2025
01:23:55
In this episode of Founder2Founder, host Aaron Spivak sits down with Josh Goldstein. Josh was a high-level college baseball player and MBA student when a once-in-a-lifetime opportunity to appear on reality TV changed everything. After the tragic and very public loss of his sister on national television, Josh turned unimaginable grief into powerful growth. Now, just a few years later, he’s built a seven-figure online fitness business empowering thousands of women, launched a supplement brand rooted in positivity, and created a personal brand focused on mindset, transformation, and authenticity.
This episode dives deep into what it means to find clarity through pain, the strategy behind monetizing real impact, and how trusting your gut can outwork any perfect plan. Josh opens up about going all-in on business, his unique approach to brand building, and the deeper mission driving every decision. Whether you're dealing with pressure, looking to turn a setback into a launchpad, or want to build with real intention, this conversation delivers. Don’t forget to subscribe, share with a fellow founder, and leave a review if you enjoyed this episode.
Chapters 02:07 – Growing Up Around Sports and Early Lessons in Discipline 09:08 – Self-Confidence Through Sports, COVID’s Impact, and Falling in Love with Sales 12:30 – Saying Yes to Love Island 17:07 – Tragedy: Losing His Sister During Filming 20:22 – Returning Home and Navigating Grief 25:10 – Starting a Business With Meaning and Honouring Her Legacy 27:17 – Serving Women in Fitness and Emotional Connection to the Mission 30:45 – The “Other 23 Hours” Philosophy in Fitness 33:28 – Josh’s Fitness Program Structure and Growth 35:46 – Personal Transformation and What He’s Still Working On 41:26 – Public Figure Pressures and Dating After Reality TV 48:05 – Business Future: Exit, Scale, or Legacy 49:20 – Starting the Supplement Company Reevyv 51:25 – Impact on Family Dynamics and Healing Through Growth 56:22 – Motivation to Repay His Parents’ Sacrifices 58:12 – Journaling, Morning Routine, and Structure 1:04:21 – Mindset as the Foundation of Transformation 1:06:13 – Avoiding Hard Conversations and Their Cost 1:11:15 – The ROI of Investing in Yourself 1:14:32 – Advice to Younger Josh: Don’t Let Others Define You 1:16:27 – Environment, Loneliness, and Finding Your Circle 1:22:38 – Final Message: Don’t Take Life Too Seriously
The Unfair Founder Advantage: How Dominic Purpura Used Crypto Profits and 1 Job to Build an Empire
30 Apr 2025
01:30:56
In this episode of Founder2Founder, host Aaron Spivak sits down with Dominic Purpura. Dominic Purpura is the founder and owner of MELA, a rapidly growing watermelon water company. After acquiring the business in 2021 following a successful cryptocurrency investment, he completely rebranded it, transforming a $25,000 monthly operation into one approaching $1 million monthly with national 7-Eleven distribution on the horizon. Influenced by his entrepreneurial father and uncle, Purpura implements a structured goal-setting system across five categories: health, wealth, wisdom, happiness, and travel. He's known for his equity-sharing leadership approach, treating employees as partners. His mission is to establish watermelon water as a major beverage category, with plans to scale MELA until, in his words "it stops being fun."
Dominic shares his journey from a young entrepreneur to achieving a major exit, breaking down the real process behind rebranding and scaling MELA. He talks about discovering MELA while building experience in the CPG industry, using cryptocurrency profits to acquire the brand, and scaling the company to an eight-figure exit. From growing up questioning traditional paths, to implementing equity-sharing leadership, to navigating life after a major acquisition, Dominic brings tactical lessons around resilience, strategic thinking, building a brand true to your values and learning to trust your gut.
Chapters: 00:43 – Introduction, Early Exposure to Entrepreneurship and Family Influence 02:05 – Growing Up Questioning Normality 03:56 – Are Entrepreneurs Born or Made? 04:33 – Learning From Father Figures and Environment 06:16 – Early Businesses, Crypto, and Falling in Love With the CPG Business Model 10:03 – Building a Beef Jerky Brand and Learning Systems 12:47 – Finding MELA and the Initial Spark 18:52 – Building Wealth Through Cardano and Crypto Strategy 22:22 – Timing the Crypto Exit and Creating Opportunity 24:08 – Acquiring MELA ,Rebranding, Restructuring, and Relaunching 29:23 – Early Wins and Rapid Product-Market Fit 30:45 – Brick-by-Brick Growth: Selling Store by Store 32:13 – Yearly Growth and the Journey From 300K to Millions 35:32 – Why MELA Worked for the Mass Market 38:15 – Building a Brand for the 99%, Not the 1% 43:29 – Losing His Father and Going All-In on Entrepreneurship 46:25 – Turning Pain Into Focus, Drive, and Daily Discipline 48:27 – Staying Focused Through Grief and Hardship 50:00 – Selling MELA and Sharing the Exit With the Team 52:31 – Navigating Identity Shifts Post-Exit 53:12 – Why Slowing Down After Success Matters 58:24 – Honouring the Journey: Reflection and Growth 1:06:12 – Building a Community: The Vision Behind Founders Club 1:14:29 – Giving First, Protecting Energy, and Scaling Smart 1:18:45 – Advice to 23-Year-Old Dominic: Trust the Journey 1:26:10 – Finding Meaning in Pain and Why It Matters
Rebuilding Purpose After a Major Exit and How The Work Doesn’t End When You Succeed with David Segal
23 Apr 2025
01:14:43
In this episode of Founder2Founder, host Aaron Spivak sits down with serial entrepreneur David Segal, best known for building DAVIDsTEA into a $200M brand and now serving as President of Highbeam. David shares the full arc of his entrepreneurial journey, starting with the humble beginnings of DAVIDsTEA, through the grind of expansion and the thrill of going public, to the surprising emotional lows that followed a major exit. With refreshing honesty, he opens up about his feelings after selling the company, how he found renewed purpose, and the process of reshaping his identity beyond his business.
David and Aaron explore the hidden cost of scaling quickly, the emotional whiplash of sudden wealth, and the importance of defining success beyond financial freedom. The conversation is packed with invaluable takeaways for founders at every stage, from negotiating working capital terms that change your bottom line, to the mindset shifts required when stepping into a new venture. Whether you’re in the trenches or on the other side of a win, David’s story is a powerful reminder that the work never really ends, it just evolves. Don’t forget to subscribe, share with a fellow founder, and leave a review if you enjoyed this episode.
Chapters: 01:10 – Starting DAVIDsTEA: The Idea Nobody Was Doing 04:32 – Early Failures and Lessons in Persistence 07:27 – From 4 Stores to 30: What Changed? 08:45 – Building for Scale: The Highs and Pitfalls 11:55 – Expansion Mistakes in the U.S. Market 14:33 – Handing Over the CEO Role: Ego and Learning 16:02 – The Power of Process (Without Bureaucracy) 20:23 – Leaving DAVIDsTEA and Losing Identity 22:15 – From Rock Bottom to Highbeam: A New Beginning 25:50 – Life-Changing Money Doesn’t Mean Life-Changing Fulfillment 28:15 – What Founders Need to Know About Life After the Exit 31:00 – Starting Mad Radish and Firebelly: Lessons in Patience 34:50 – David Now vs. Then: Maturity in Decision Making 38:52 – Sleep On It: Slowing Down to Make Better Decisions 40:09 – Working Capital Masterclass: The Deal That Can Save Millions 44:03 – Lifestyle Business or Unicorn? How to Decide 46:41 – Operating for Cash Flow vs. Chasing the Exit 48:57 – The Power of Compounding and Long-Term Operating 50:33 – Managing Post-Exit Wealth: Keep It Simple 54:56 – David on Legacy and Still Being “Just Getting Started” 58:20 – The Power of Environment and a Supportive Partner 1:01:25 – Entrepreneurship is a Personal Journey 1:03:39 – Advice to 19-Year-Old David: Put in the Work, Keep Showing Up 1:06:19 – Meditation, a “Digital Sabbath”, and Mental Resilience as a Founder 1:11:07 – Final Reflections: Inputs Over Outcomes
Investing in Your Body for Business Longevity: Hector Maradiaga on Why Vitality is an Asset
05 Nov 2025
01:07:21
In this episode of Founder2Founder, Aaron Spivak sits down with Hector Maradiaga, founder and CEO of Infinity Delta. Hector has spent over a decade optimizing human performance for NFL athletes, Fortune 500 executives, and high-performing founders through data, science, and AI. Now, he's on a mission to make vitality the world’s most valuable asset.
Hector shares how his journey started by helping his immigrant father build a business from scratch, why he walked away from taking it over, and how that decision led to years of internal conflict. He opens up about the real cost of trying to prove people wrong, losing millions, and ultimately finding clarity through faith and a renewed sense of purpose. For founders pushing to scale while trying to stay grounded, this conversation gets into what actually sustains long-term performance.
Chapters 00:02 – Intro to Hector and Infinity Delta 02:08 – Born in Honduras, Raised in Hustle 04:03 – Running Excel Estimates at Age 8 05:39 – Launching a Candy Business in Grade School 06:50 – Building a Team and Learning Profit Split 08:17 – Keeping Business Quiet at Home 10:16 – The Candy Empire Collapses 12:34 – Working With His Dad Every Weekend 14:03 – Struggling With Financial Discipline Early On 15:50 – Spending Tomorrow’s Money 17:24 – Business Was Sport, Until It Wasn’t 18:52 – Stepping Away From the Family Business 19:52 – The Unspoken Guilt of Changing Paths 22:31 – The Day He Dropped Out 24:49 – Going From Comfortable to Survival 26:38 – Feeding His Younger Brother During the Crash 28:26 – Hearing “I’m Proud of You” For the First Time 30:02 – Rebuilding Connection With His Father 33:26 – Planning the Costa Rica Surprise 35:23 – Shifting From Proving People Wrong to Living With Purpose 38:37 – Focused Scaling and Clear Vision 40:08 – Killing Ego to Build Longevity 42:33 – The Final Boss: Inner Conflict 44:58 – You Can’t Fix Home With Money 46:56 – Choosing the Vehicle to Your Vision 48:34 – Entrepreneurs Are Modern Day Athletes 51:28 – Why Founders Don’t Prioritize Their Health 53:18 – Know Thyself: Performance Starts With Data 56:11 – It's About Better Years, Not Longer Life 58:34 – What Founders Miss by Waiting to Focus on Health 1:01:47 – Health as an Asset, Not an Expense 1:02:59 – The Last Decade to Invest in Your Future 1:03:31 – Your Life Is Worth More Than a Billion 1:04:00 – What He’d Tell His Younger Self
A Framework for Founders On How To Check In Before You Check Out with Adam Klasner
16 Apr 2025
01:32:32
In this episode of Founder2Founder, host Aaron Spivak sits down with Adam Klasner. Adam Mordechai Klasner is a widely respected personal growth facilitator, committed to empowering individuals and nurturing meaningful relationships. He masterfully integrates diverse modalities and techniques, including Breathwork, NLP (Neuro-Linguistic Programming), Family Constellations, and Imago facilitation, to guide his clients on transformative journeys. Adam's approach centers on a holistic comprehension of his clients' inner worlds and their connections with others. By harmoniously merging these aspects, he skillfully helps clients achieve profound self-awareness, heal past wounds, enhance communication, and foster profound harmony in their relationships.
In addition to his professional endeavours, Adam leads a fulfilling personal life. Happily married and the proud parent of ten children, he appreciates the significance of balancing personal and professional pursuits, while infusing joy into both.
Adam shares how facing himself 12 years ago began a life-altering shift, leading him to help men reconnect with their authentic selves. The conversation dives into the concept of “checking in”, a practice of emotional awareness, and how that self-awareness can transform how we lead, live, and relate to others. With a blend of vulnerability, spiritual insight, and grounded leadership, Adam offers tools for founders to identify emotional triggers, address inner wounds, and lead from a place of truth rather than fear.
If you enjoyed the episode please subscribe and share this podcast with someone you think could benefit from it!
Chapters: 01:30 Who Is Adam Klasner? 02:40 The Internal Crisis That Changed Everything 05:03 The Workshop That Triggered a Life Transformation 06:35 Why Most Men Say “I’m Good” And What They're Missing 08:32 Aaron’s First Workshop Experience in Montreal 11:06 How a Check-In Transformed a Meeting 13:19 What Is a Check-In? A Tool for Real Vulnerability 17:00 Why We Hide Behind Masks in Business and Life 20:13 How Childhood Stories Shape Leadership Patterns 23:08 Authenticity vs. Connection: The Tension We All Face 25:33 Why Every Founder Must Balance Both to Lead 26:50 Practical Daily Tools to Access Your Inner World 30:06 Triggers Are Clues: How to Work with Emotional Discomfort 32:43 Journaling, Breathwork, and Self-Inquiry: Building a Practice 36:41 Aaron’s Real-Time Trigger: A Business Partner Conflict 49:27 Discovering the Root Need Beneath the Reaction 53:04 Why Real Growth Requires Revisiting the Past 58:40 Aaron’s “I’m Not That Good” Belief and Where It Began 01:04:01 The Power of Acknowledging What Is 01:05:59 Where to Start: Journaling and Awareness 01:10:25 Gratitude for the Past: Why Everything Happens for a Reason 01:14:12 What Spiritual Practice Taught Adam About Leadership 01:19:56 The Moment Adam’s Father Told Him “You Can Do Anything” 01:30:08 Message To Younger Self
The Secret to Scale? It Wasn’t Capital — It Was Community, with Gary Lipovertsky
09 Apr 2025
01:42:25
In this episode of Founder2Founder, host Aaron Spivak sits down with Gary Lipovetsky. Gary Lipovetsky is a digital entrepreneur, strategist, and creator with a track record of building and scaling online businesses. As the co-architect of Valeria Inc., he helped transform Valeria’s audience into a thriving global media company. Before that, he founded a top 100 global website with 200 million monthly sessions at its peak, built multiple successful social platforms, and raised $32 million in venture capital for an eCommerce startup within its first year. Now, Gary also mentors hundreds of creators through Creator Method, an academy helping them master monetization, community growth and even personal development through content creation. As the host of RISE podcast, he uncovers the strategies of top entrepreneurs and industry leaders. With 30 years in digital media, he continues to guide brands and creators in building lasting, impactful communities, resulting in the achievement of their business goals.
He talks about the early days of hustle, knocking on doors, cold calling local businesses, and hand-delivering coupon deals before DealFind ever became a household name. Gary opens up about the scaling phase and what he learned from building a company at lightning speed. He shares why launching a personal YouTube channel was never part of the original plan, how he built it to over a million subscribers, and what the platform taught him about branding and storytelling. Now in his next chapter with Free, he reflects on how his priorities have evolved, what he’s building towards, and why success today looks very different than it used to. This episode is a candid look at growth, reinvention, and staying grounded through it all.
Be sure to rate the podcast and subscribe or follow on your favorite platform so you never miss a new episode, every Wednesday!
Chapters: 01:35 Motivations Behind Success 02:12 Early Life and Challenges 04:30 Taking Control of One's Future 06:01 First Steps into Entrepreneurship 14:06 Defining Entrepreneurial Identity 16:01 Partnerships and New Ventures 22:36 The Impact of Content Creation 30:52 The Dynamics of Relationships and Support 33:22 The Power of Quick Implementation 37:49 The School of Execution: Learning by Doing 40:04 Community vs. Audience: The Shift in Content Creation 46:03 The Importance of Focus in Content Creation 57:54 The Birth of Creator Method: Community and Purpose 01:08:55 Empowering Others: The Mission Behind Creator Method 01:10:28 The Power of Collaboration Among Creators 01:12:30 Shifting Perspectives: From Competition to Community 01:13:00 Debunking the Algorithm Myth 01:20:00 Redefining Masculinity: Supporting Your Partner's Growth 01:30:32 Embracing Mortality: Living with Intention 01:39:10 Choosing Gratitude: A Perspective Shift
From 3D Printer to Multimillion-Dollar Brand: Jay Conohan's Playbook for Turning Simple Ideas Into Real Revenue – Without Chasing the Spotlight
02 Apr 2025
01:31:51
In this episode of Founder2Founder, host Aaron Spivak sits down with Jay Conohan. Jay Conohan is the founder of The Loud Cup Company, a serial entrepreneur, inventor, and proud father of three. With a relentless drive to figure things out, he’s built his career on resilience, hard lessons, and a willingness to bet on himself. From launching the Bath n Play, to juggling multiple ventures while holding a day job, Jay has faced failures head-on and turned them into stepping stones. He believes in fairness, brutal honesty, and proving people wrong when they count him out. With no degree but an unstoppable mindset, he’s built a life around innovation, family, and pushing limits—both in business and beyond.
Jay dives into the critical moments that shaped his path, from making tough financial decisions to refining operations and leadership. He breaks down the mindset shifts that helped him scale and the lessons he learned along the way. This conversation is packed with real insights on what it takes to grow a business against the odds. Don’t miss this deep dive into the mindset and strategies behind real entrepreneurial success.
Be sure to rate the podcast and subscribe or follow on your favorite platform so you never miss a new episode, every Wednesday!
Chapters: 03:07 Early Entrepreneurial Experiences and Lessons Learned 05:51 The Impact of COVID on Business Ventures 08:59 The Birth of the Bath and Play Product 11:53 Networking and the Founders Club Experience 15:02 The Role of Support Systems in Entrepreneurship 17:59 Navigating Success and Self-Discovery 21:01 Finding Purpose Beyond Business 23:49 The Importance of Relationships in Business 27:09 Facing Fears and Embracing Growth 29:33 The Innovative Cup: A Unique 3D Printing Experience 31:10 Building Connections: The Power of Networking 32:43 Kickstarter Journey: From Concept to Launch 34:10 Trusting the Process: Lessons in Entrepreneurship 38:40 Scaling Up: The Transition from Kickstarter to E-commerce 41:13 Achieving Rapid Growth: From Zero to Seven Figures 44:43 Navigating Success: Balancing Business and Personal Life 54:42 Reflections on Opportunity Cost 57:53 Strategic Partnerships and Growth Potential 01:01:35 The Power of Networking and Self-Awareness 01:03:40 Lessons from Business Setbacks 01:10:41 Turning Challenges into Opportunities 01:19:11 Finding Purpose After Success 01:26:28 Messages to My Younger Self
How to Go From Nothing to a Multimillion-Dollar Brand Without Outside Funding with Lior Ohayon
26 Mar 2025
01:11:35
In this episode of Founder2Founder, host Aaron Spivak sits down with Lior Ohayon. Lior is a serial entrepreneur from Toronto, now based in Miami with his family. Finding early success in the internet marketing world, he eventually transitioned into tech and landed on e-commerce. His most recent co-founded business Hush, sold to a publicly traded company for a landmark $48M deal. Now he spends his time helping other startups find their voice and refine their story for a major exit.
Lior Ohayon shares how he went from dropping out of school to building Hush into one of North America's top weighted blanket brands. He breaks down the key decisions that shaped his path, from leveraging SEO to fund his early ventures, taking calculated risks, and scaling a product-based business from the ground up.
He reflects on the turning points that defined his journey, from struggling with seasonality, to launching a record-breaking Kickstarter and ultimately exiting the company. This conversation gets into the mindset and strategies behind real business growth. Be sure to rate the podcast and follow on your favourite platform, so you never miss a new episode every Wednesday!
Chapters: 03:07 The Decision to Drop Out of School 06:02 First Steps into Entrepreneurship 08:55 Transitioning to Software and SEO 11:54 The Birth of Hush and Partnership Dynamics 14:54 Navigating Challenges and Scaling the Business 17:54 The Kickstarter Success Story 21:07 Building Trust and Collaboration 23:56 Celebrating Small Wins and Validation 26:50 Overcoming Seasonal Challenges 30:06 The Power of Belief and Support 32:59 Lessons Learned from Partnership 38:12 The Power of Problem Solving 39:46 Goal Setting: A Catalyst for Success 42:52 The Importance of Hard Work and Team Dynamics 45:15 Learning Through Experience: The Journey of Entrepreneurship 48:46 The Role of Preparation in Business Success 51:48 Navigating Growth and Change During COVID-19 54:34 The Importance of Values in Business 01:01:16 Reflections on Personal Growth and Future Aspirations
Using a Relentless Mindset to Build and Sell a Nine-Figure Empire with Anne Mahlum
19 Mar 2025
01:38:48
In this episode of Founder2Founder, host Aaron Spivak sits down with Anne Mahlum. Anne is a serial entrepreneur, investor, and speaker known for building impactful businesses. She founded Back on My Feet, a nonprofit helping individuals experiencing homelessness, and [solidcore], one of the nation’s fastest-growing fitness brands. Under her leadership, [solidcore] expanded to 120+ locations and raised $210M. After successfully exiting in 2023, Anne now invests, advises, and speaks on leadership, risk-taking, and living boldly.
In this conversation, Anne shares how she bet on herself, overcame self-doubt, and made bold decisions to scale her business rapidly. She breaks down key lessons in leadership, risk-taking, and negotiating high-stakes deals while navigating challenges like lawsuits and the pandemic. Her story is a masterclass in resilience and strategic thinking, making this episode a must-listen for anyone looking to build and exit a successful company.
Continue to subscribe and share this podcast with someone you might think could benefit from it! We appreciate your support!
Chapters: 02:10 - Anne’s Early Entrepreneurial Journey and Founding Back on My Feet 06:30 - Transitioning from Nonprofit to Launching [solidcore] with $175K 10:45 - Scaling [solidcore] Rapidly and the Subway Expansion Strategy 15:20 - The Art of Negotiation: How Anne Secured Favourable Lease Terms 20:50 - Breaking Away from Supplier Dependencies and Legal Battles 25:26 - Leading Through Crisis: How Anne Navigated [solidcore] Through The Pandemic 30:43 - Transitioning Out of the CEO Role and Preparing for Exit 35:16 - Selling [solidcore] for Nine Figures and Lessons in Wealth Management 41:32 - Strategic Decisions That Scaled [solidcore] to Over 120 Locations 46:27 - Why Entrepreneurs Need to Deeply Understand Their Numbers 51:47 - The Importance of Surrounding Yourself with the Right People 56:55 - Life After Exit: Navigating Identity and Purpose Beyond Business 1:03:46 - Shutting Down Ambition and Embracing a New Chapter 1:08:06 - Balancing Masculine and Feminine Energy as a Female Founder 1:15:26 - The Truth About Relationships, Success, and Finding the Right Partner 1:28:08 - The Power of Momentum and How to Create It in Business and Life 1:35:17 - Anne’s Advice to Her Younger Self: Stay Curious and Keep Doing
How to Run Your Business with True Authenticity, Momentum and The Superpower of Being Unapologetically Yourself with Jake Karls
12 Mar 2025
01:11:50
In the first official episode of Founder2Founder, host Aaron Spivak along with Cohost Chris Meade, welcome Jake Karls. Jake is Co-founder and Chief Rainmaker of Mid-Day Squares, the better for you chocolate brand that went from a kitchen table idea to a North American sensation. Known for his unapologetic authenticity and refreshingly relatable approach, Jake has been recognized as a rising star in the business world. He made Forbes’ 30 Under 30 list for Food and Beverage, and is currently a finalist for EY’s Entrepreneur of the Year awards.
Jake shares his journey of embracing his superpower, being himself, to build momentum and scale a brand that is as real as it gets. He opens up about overcoming insecurities, the power of showing up in person, and why building friends, not just customers, has been the cornerstone of Mid-Day Squares' success. From dealing with investor pushback to navigating the pressures of being the face of a rapidly growing company, Jake’s insights are a masterclass in leadership and authenticity.
This episode is packed with actionable advice and real talk. Jake Karls is redefining entrepreneurship with authenticity and showing why embracing who you are might just be the ultimate business strategy. Be sure to rate the podcast and subscribe or follow on your favourite platform so you never miss a new episode, every Wednesday!
Chapters 00:02 - Introduction to the Founder to Founder Podcast 02:12 - How Jake Carl’s Energy and Confidence Started from Insecurity 03:23 - Overcoming Fear and Learning to Lean Into Strengths 05:56 - Finding the Right Role in Business and Letting Go of Ego 08:15 - The Power of Communication in Entrepreneurship and Partnerships 10:41 - How Conflict Can Destroy or Strengthen a Business Relationship 12:39 - The Challenges of Being a Public Figure and Representing a Brand 15:13 - Staying Authentic While Scaling a Business and Facing Public Scrutiny 17:25 - The Realities of Traveling Constantly and Maintaining Relationships 19:53 - The Sacrifices Entrepreneurship Demands and Finding Balance 24:06 - Why Communication and Therapy Are Key to Business Longevity 29:26 - Fear of Growing Up, Taking on Responsibility, and Losing Freedom 33:53 - How Proving People Wrong Became a Driving Force for Success 38:20 - Building a Personal Brand to Elevate Your Business and Career 42:03 - The Power of Showing Up and How It Opens Unexpected Doors 48:13 - How to Separate Your Identity From Your Business for Long-Term Growth 53:44 - The Role of Momentum in Success and How to Maintain It 1:01:18 - Identifying Energy Drainers and Protecting Your Time 1:07:06 - What Jake Would Tell His Younger Self About Life and Success 1:10:19 - Final Thoughts on Canadian Entrepreneurship and Community
In the short teaser trailer of Founder2Founder, host Aaron Spivak sets the stage for what listeners can expect from this raw and unfiltered podcast. Fuelled by his passion for entrepreneurship, Aaron will be sharing the real stories behind building a business, from the late nights and brutal setbacks, to the game-changing moments that make it all worthwhile. His goal is simple: to bring candid conversations with fellow founders to a bigger stage, diving deep into the grit, growth, and the mindset needed to keep pushing forward when most would quit.
Whether it’s solo episodes exploring Aaron’s own entrepreneurial journey or interviews with visionaries who have carved out their own paths, Founder2Founder promises to deliver the truth about what it takes to build something that truly matters. New episodes drop every Wednesday on all major platforms, so tune in, subscribe and rate this podcast to stay up to date on all the amazing conversations to come!
Loaning $1M to His Campaign, Then Putting It All in Bitcoin with Michael Carbonara
29 Oct 2025
01:01:22
In this episode of Founder2Founder, Aaron Spivak sits down with entrepreneur and now congressional candidate Michael Carbonara, committed to serving the people of Florida’s 25th District. Known for building fintech and blockchain companies that processed over $20 billion a year, Michael made headlines when he left it all behind, loaned his campaign a million dollars, and put it entirely into Bitcoin.
Michael shares how growing up in a single-parent household shaped his hunger for success, what it took to become a pioneer in crypto banking, and why he believes the American dream is fading unless people like him step up. From building global infrastructure in blockchain to running for office against a 20-year incumbent, this episode covers business, politics, family, and legacy in a way few founders ever do.
Chapters: 01:46 – Where His Entrepreneurial Spirit Started 03:19 – Dropping Out Before It Was Cool 04:47 – The Turning Point From School to Self-Education 06:14 – How Rich Dad, Poor Dad Changed His Worldview 08:16 – Starting a Payment Gateway While Holding a Day Job 09:43 – Why Working With Older Partners Changed Everything 11:13 – Becoming a Blockchain Pioneer Before the Hype 13:05 – Why He Still Believes 50% of the World Will Use Blockchain 14:38 – Web3 Is Coming Whether You Understand It or Not 16:31 – The Reality of Building in an Unproven Industry 17:42 – Pivoting Without Quitting: His Approach to "Failure" 18:41 – The Mentors Who Shaped His Entrepreneurial Mindset 20:14 – Why We All Thrive in Different Systems 22:28 – Childhood Lessons That Still Shape His Drive 24:19 – Why He Decided to Run for Office 26:09 – How a Documentary Sparked His Political Awakening 28:28 – Going Up Against a 20-Year Incumbent 30:35 – Restoring Safety, Slashing Waste, and Defunding 32:17 – What He’d Ask Under Oath 34:05 – Family, Risk, and Running With No Fear 35:16 – Why He Invested Campaign Funds Into Bitcoin 37:06 – Making Bitcoin Accessible for Real Wealth Creation 38:35 – Solving the Security and Simplicity Gap in Crypto 40:56 – Taking a Pay Cut to Serve the Country 42:44 – What Happens Without Police and Structure 44:25 – School Choice, Indoctrination, and Fixing Education 47:03 – His Vision for the Next 24 Months 48:30 – Why He Had to Become a Reluctant Social Media Influencer 50:04 – How 7 Million Views Landed Him in the White House 52:57 – How the Dream Is Still Possible, but Not Guaranteed 54:33 – Advice to His 12-Year-Old Self 56:56 – How His Wife Became His Most Trusted Advisor 59:25 – Why He Believes the Time to Act Is Now
Inside The Founders Club: Vision, Vulnerability, and What’s Next with Chris Meade
22 Oct 2025
00:34:55
In this episode of Founder2Founder, Aaron Spivak sits down once again with Chris Meade to talk about the evolution of Founders Club and where it's headed next. With nearly 700 members and over 120 events planned for the coming year, they share how they’re scaling intentionally while keeping the community tight and valuable.
They break down lessons from the Puerto Rico offsite, the LA chapter relaunch, and why success today means supporting founders beyond business, into relationships, parenting and personal growth. It’s a real look at what it takes to build something that lasts.
Chapters:
01:24 – Kicking off our LA Chapter 02:22 – Puerto Rico offsite and club planning 03:19 – Improving Member Quality and Filters 04:38 – Redefining Success Beyond Business 05:56 – How Money Doesn’t Solve the Hard Stuff 06:48 – The Missing Support For Personal Relationships 07:56 – A New Lens On What Makes A Founder Successful 08:58 – Member Anthony’s Shift From Brand Growth To Marriage 10:03 – Learning From Founders Ahead Of You 11:19 – What Really Got Discussed At Female Founder Day 12:15 – What Motivates Founders After Kids 12:57 – Why Peer Networks Matter More Than Ever 13:27 – 2026 Events And Picking The Right Venues 14:53 – Founders Club Is Not An Events Company 15:56 – Forums As The Foundation Of Deeper Value 16:48 – Members As Speakers, Not Hired Talent 17:28 – Booking Dream Speakers For The Community 18:28 – Keeping It Fun Or Shutting It Down 19:33 – Why This Is A 30-Year Vision 21:00 – A Goal To Be Part Of Global GDP 21:34 – The Club As The First Call When You Need Help 23:11 – Removing The Wrong Energy 24:40 – Events That Spark Action 25:25 – When The Club Drives Real Business 26:46 – Unlocking Perks And Member-Only Access 27:57 – Why Founders Need Better Tools And Support 28:50 – What FD Chat And The App Will Offer 30:18 – Creating Better Matches Through Data 30:52 – How Many Real Connections You Can Have 31:24 – Focus On 5 People A Year 32:46 – One Billionaire’s Honesty Changed The Room
Breaking Into Steel: Kinga Strogoff on Owning Her Place in a Man’s World
15 Oct 2025
00:58:08
Kinga Strogoff is the President & CEO of Second Street Iron & Metal, Chairman & Creative Director of Balmoral Defender, and a Board Member at Basalt International. She runs a third-generation scrap metal business, reshapes luxury automotive design, and drives innovation in sustainable materials, all while raising her son as a single mother.
In this episode, Kinga shares how she moved to the U.S. from Poland as an au pair, eventually took over her husband’s steel business, and led it through collapse and revival. She talks openly about loss, building resilience, and why she believes obsession, not balance, is key to building anything meaningful. Her story spans legacy, grief, and the discipline it takes to keep moving forward.
Chapters: 02:23 – From Polish Village to the American Dream 04:32 – The Power of Dreaming Beyond Logic 06:00 – When Manifestation Goes Wrong 07:44 – Leaving Home Against All Odds 08:40 – Becoming an Au Pair to Escape Limitations 09:47 – The Family That Waited a Year for Her 10:26 – Feeling Called to America at Age 6 12:28 – Entering the Workforce and Loving Money 13:24 – Childhood Hustle: Scrap Metal and Sneakers 15:31 – Her Grandfather’s Influence and Deep Bond 17:04 – The Story Behind the Name “Kinga” 19:51 – Building Kinga Steel from the Ground Up 21:42 – Visualizing Life as a Painting 22:37 – No Plan B: Betting on Herself 23:13 – Meeting Her Husband and Building a Life 25:53 – Taking Over the Business During Crisis 27:25 – 24 Months of Full Obsession 28:38 – Earning Respect in a Male-Dominated Industry 32:39 – Advice to Women in Male-Dominated Fields 34:34 – When She Knew the Business Would Thrive 35:59 – Leading Through Legacy and Empowering Her Team 36:56 – The Loss of Her Husband and the Aftermath 39:12 – Rebuilding While Raising Her Son Alone 41:44 – Jump Rope Therapy: Turning Pain Into Purpose 42:51 – Fitness, Discipline, and Mental Strength 46:06 – Obsession Over Balance: Her Success Philosophy 47:51 – What’s Next? Learning to Sit in the Unknown 49:12 – What She’d Tell Her 6-Year-Old Self 52:32 – Creating Heaven on Earth, Every Day 54:40 – The Role of Social Media and Building Brand Authentically 56:03 – Protecting Her Son and Living in Silence 56:45 – Sharing Her Story to Help Others Heal
How Keida Dervishi Built Soulmate Customs Into A 7-Figure Brand at 19 With No Ads, and 40 Posts a Day
01 Oct 2025
01:06:42
In this episode of Founder2Founder, Aaron Spivak sits down with Keida Dervishi, the 23-year-old founder of Soulmate Customs, a custom embroidery brand that hit $1 million in revenue in under 11 months without spending a dollar on ads. What started as a hoodie gift for her mom’s birthday quickly turned into a viral business powered by emotional storytelling and relentless content creation.
Keida shares how growing up in an immigrant household shaped her drive, how she transitioned from child star in Albania to business builder, and what it’s like leading a fast-scaling brand at such a young age. From hiring mistakes, to burnout, staying grounded, to posting 40+ times a day, this conversation is a real look at what it takes to scale with zero shortcuts.
Chapters: 02:08 – Growing Up in an Entrepreneurial Household 03:47 – From Child Star to Burnout on Stage 05:43 – Accidentally Entering Entrepreneurship 07:00 – The Hoodie Gift That Started Soulmate Custom 09:58 – Viral Launch and Selling Out Within Days 11:32 – No Strategy, Just Action: Early Days of Posting 12:37 – Moving Out of Her Bedroom to Scale Fulfillment 13:02 – First TikTok Lives and Learning to Sell 14:22 – Hiring Challenges and Missteps 15:45 – The Family Business Breakdown: Who Does What 16:37 – Discovering Her Why: The Fear That Fuels Her 18:01 – A Breakthrough Moment at Founders Club 19:04 – The Realities of Building While Your Parents Age 21:10 – Navigating Burnout, Routines, and Sleep Struggles 23:10 – Posting 40+ Times a Day: Pressure and Purpose 25:12 – Why Consistency Is Her Superpower 27:21 – Leading a Team as the Youngest in the Room 30:44 – Building Confidence and Letting Go of Limiting Beliefs 34:11 – Embracing Embarrassment to Achieve Greatness 35:27 – What Keeps Her Going: Live Calls with Customers 38:47 – Giving Credit Where It’s Due and Admiring the Work 41:38 – What’s Next for Soulmate Customs 44:45 – Learning to Let Go as the Business Grows 49:28 – Curating Her Circle and Protecting Her Environment 54:25 – Working With Her Brother and Navigating Family Tension 57:22 – What She’d Tell Her 9-Year-Old Self
From Nightlife to Nine Figures: Heath Wolfson on Trendspotting and Building with Purpose
24 Sep 2025
00:59:12
In this episode of Founder2Founder, Aaron Spivak sits down with Heath Wolfson, serial entrepreneur and founder of FrontCare, a creator-powered telehealth platform. With a 20-year track record of building businesses across safety, media, and health, Heath shares how he’s repeatedly turned market inefficiencies into high-growth ventures.
He opens up about navigating failure, executing without outside capital, and spotting cultural trends before they explode. From launching Tattoo Nation in shopping malls to scaling one of Facebook’s biggest publishing engines, Heath now turns his focus to reshaping healthcare access through affiliate-driven telehealth.
Chapters: 02:49 – Early Life, College, and First Entrepreneurial Sparks 03:57 – A Practical Approach to Entrepreneurship 04:58 – The First Business: Event Marketing in NYC 06:35 – Lessons from a Short-Lived Nightlife Venture 07:51 – A Quick Detour at Morgan Stanley 08:52 – Bringing Tattoo Parlors to Shopping Malls 10:35 – Navigating Regulations in Traditional Retail 12:45 – The 2008 Crash and a Failed Expansion 13:56 – Forgetting a $100M Success: Glow-in-the-Dark Safety 15:56 – Getting a Law Passed and Building a Manufacturing Deal 17:19 – How a Nightlife Job Led to a Fortune 19:22 – Partnership, Production, and Exit to a National Brand 21:49 – Real-Time Pattern Recognition and Risk 22:32 – Understanding Market Timing and Survival 24:11 – Acquiring Inked Magazine and Going Omnichannel 25:36 – The Birth of Facebook E-Commerce 27:00 – Owning and Monetizing Massive Facebook Pages 28:38 – Cambridge Analytica Fallout and Platform Risk 30:51 – Why Timing is Everything in Business 32:22 – The Dangers of Scaling Too Fast 33:42 – Zooming Out: Lessons Over Two Decades 34:46 – Transitioning from Media to Health 35:38 – Accidentally Overdosing on Ozempic 37:48 – Experiencing the Power of GLP-1s Firsthand 39:21 – Bootstrapping a Brick-and-Mortar Weight Loss Clinic 40:51 – Selling Telehealth Models to Founders and Creators 43:11 – Breaking Down the Legal Fight Between Compounders and Big Pharma 44:36 – Making Health an Empowered Conversation for Creators 45:52 – Building a Trust-Based Health Affiliate Ecosystem 47:31 – Quality Control and Compliance in Telehealth 48:45 – Inside the FrontCare “Clinic as a Service” Model 49:46 – Helping Gyms, Salons & Clinics Monetize Wellness 50:38 – Legacy Thinking and the Next Chapter 52:26 – Advice to His 17-Year-Old Self: Buy Real Estate 53:56 – Why Money is a Tool, Not a Destination 55:07 – Empowering Through Access and Ownership
Uncomfortable Either Way: Why Growth Requires Choosing the Hard Path with Brett Eaton
17 Sep 2025
01:09:24
In this episode of Founder2Founder, Aaron Spivak sits down with Brett Eaton, keynote speaker, high performance coach, and author of Uncomfortable Either Way. After a life-changing back injury and the loss of his father at 16, Brett discovered a powerful truth: life is going to be uncomfortable no matter what, so choose the version that leads to growth.
He shares the frameworks behind his success, including the game-changing “Sunday Setup,” how to spot self-sabotage in real time, and why founders must upgrade their relationship with discomfort and money. This conversation is packed with raw honesty and practical takeaways for anyone serious about building a life that lasts.
Chapters: 02:14 – Brett’s Origin Story: Injury, Loss, and a New Lens 03:46 – Sports, Hustle, and Learning to Love the Grind 05:10 – When Patience Becomes an Excuse 06:34 – Living in 90-Day Sprints 08:01 – Gamifying Progress to Stay Consistent 09:38 – Who Actually Needs a Coach? 11:06 – Bad Coaching Investments & What to Watch For 12:56 – Transitioning Out of Fitness-Only Coaching 14:27 – Starting with Strengths, Not Weaknesses 15:36 – Taking a Life Inventory 17:00 – Learning While You’re Winning 19:08 – The Full Sunday Setup Breakdown 21:50 – Identifying Weekly Landmines 24:59 – If It’s Not on the Calendar, It’s Not Real 27:06 – Why Founders Must Prioritize Energy 29:27 – The “F*ck It” Button: Spotting Self-Sabotage 33:43 – The Comfort Trap 34:40 – The Cost of Coasting: Blockbuster Syndrome 37:48 – Embracing the Good Old Days While You’re In Them 39:32 – Being Young vs. Being Present 40:45 – “I’m in My Prime”: A New Morning Mantra 41:49 – What Comfort Really Signals 45:14 – Why Brett Finally Wrote the Book 47:27 – Money Mindset & Unlearning Limiting Beliefs 50:38 – Facing the Numbers & Taking Control 54:25 – Surrounding Yourself with People Who Talk About Money 1:01:31 – One Honest Question That Changed the Game 1:05:12 – Advice to His 16-Year-Old Self
How Brandon Pourmorady Built a $20M Creator Economy Business by Age 25
03 Dec 2025
01:02:18
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 Exit
Why Most Founders Are Unprepared for Privacy Laws & How to Build a Business That Survives Them with Richart Ruddie
17 Dec 2025
01:01:22
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 Advantage
How Armstrong Williams Became One of America’s Most Powerful Minority Media Owners
10 Dec 2025
01:39:38
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.
Chapters 02:42 – Growing Up on a Farm & Learning Discipline from His Parents 05:56 – Meeting Senator Strom Thurmond: A Life-Altering Moment 06:32 – Interning in DC & Discovering His Calling 08:43 – Naivety, Risk & Being Ready When Opportunity Arrives 11:42 – The Story of His Father Buying Their Family Farm 14:56 – Early Lessons on Judging Character as Individuals, Not Groups 17:29 – How His Upbringing Influenced the Naming of His Company 19:12 – Getting Cut Off Financially & Learning He Was an Entrepreneur 21:46 – His Father's Rule: Always Squirrel Away 20% 23:09 – The $200 Check That Turned Into $42K: His First Business Win 26:31 – Convincing Richard Pryor to Speak for Black History Month 28:16 – Meeting His First Business Mentor Through This Event 29:36 – Investing $25K That Turned Into $7M by Age 27 30:35 – The Power of Long-Term Wealth & Strategic Investing 34:53 – The Importance of Giving Back & Empowering Others 36:25 – Why Most Young Entrepreneurs Don’t Understand Morality 39:05 – Managing Hundreds of Relationships with Intention 44:13 – Creating & Scaling Howard Stirk Holdings 49:56 – Buying His First Network TV Stations 51:12 – The Power of Local Media and Deciding Elections 54:03 – Why He’ll Never Be Compromised by Advertisers 57:20 – Why Revenge Is a Dangerous Game in Business & Politics 59:33 – On Mistakes, Regret, and Taking Full Responsibility 1:03:39 – Why He Personally Signs Every Check in His Business 1:05:45 – The Power of Hard Conversations and Emotional Maturity 1:10:35 – Intuition, Spiritual Currency & Reading Energy 1:15:56 – Why Soul > Strategy for Long-Term Success 1:23:28 – The One Thing Young Founders Need to Start Doing 1:35:26 – Advice to His 17-Year-Old Self
In this episode of Founder2Founder, Aaron Spivak returns with Chris Meade for a founder-to-founder deep dive on the biggest insights shaping business growth in 2026. After surveying over 1,000 members from inside The Founders Club, they uncovered five powerful patterns that separate the founders who are doubling their growth from those who stay stuck. The truth? It’s not about doing more, it’s about going deeper on what’s already working.
Together, they unpack the mindset shifts, tactical strategies, and daily disciplines top founders are leaning into this year. From clarity of vision to committing to one channel, empowering teams, building real founder connections, and using AI as leverage (not leadership), this episode is packed with hard-earned insights and actionable takeaways. Whether you’re scaling past $10M or just trying to get momentum back, this is the playbook for founders ready to build with purpose
Chapters:
01:03 – The Truth About Founders Who Break Through
02:08 – Why Clarity and Focus Beat Chaos
03:47 – Avoiding Shiny Object Syndrome in 2026
05:25 – The Anxiety That Comes from Lack of Vision
06:44 – Ask Yourself: Is Your Business Even Scalable?
08:30 – One Channel. One Plan. No Distractions.
09:49 – The Founders Who Are Crushing It Aren’t Multichannel
11:00 – Are You Testing a Channel or Building It?
12:51 – The Difference Between Committing vs. Experimenting
14:06 – The Real Reason Founders Don’t Go All In
17:01 – Creating Feedback Loops to Build Momentum
19:05 – Why Small Wins Shouldn’t Be Overlooked
20:01 – Founder Bottlenecks and How to Eliminate Them
22:04 – Panic Execution Is a Sign of Broken Systems
23:42 – Giving Teams Ownership of Their "Piano"
25:12 – The Power of Real-World, In-Person Connection
26:10 – Your Network is Who Picks Up the Phone When It Gets Hard
28:08 – Give First: The Foundation of True Founder Relationships
30:02 – What Real Founder Support Looks Like
33:58 – Why Your Circle Defines Your Trajectory
35:35 – AI is Leverage, Not Leadership
42:03 – AI for Speed and Margin, Not for Connection
44:58 – Clear Strategy, Committed Team, One Goal
48:35 – Inside the Vision for Founders Club 2026
51:17 – Why Integrity is Everything as You Scale
53:24 – Designing Events That Actually Serve Founders
56:09 – The Power of Physical Spaces in a Digital World
58:10 – Are We Building Community the Right Way?
1:06:30 – Why Gender-Specific Events Are Unlocking Deeper Growth
1:08:00 – Founders Forum LA: Our Biggest Event Ever
1:11:45 – Redefining Sponsorships to Actually Add Value
How Adam Wexler Bootstrapped His Way to a Multi-Billion Dollar Exit
21 Jan 2026
01:47:31
In this episode of Founder2Founder, Aaron Spivak sits down with Adam Wexler, Founder and Executive Chairman of PrizePicks, the largest paid fantasy sports platform in North America. With a career spanning from music tech startups to influencer marketing software and now dominating the fantasy sports industry, Adam is a prime example of what it means to build with vision, grit, and resilience. Beyond PrizePicks, Adam has launched multiple ventures, served as a pioneer in fantasy sports innovation, and continues to shape the industry through his not-for-profit initiatives and leadership as an active board member.
Adam opens up about his early years experimenting with product-market fit, including his first startup GoRankem, the transition into B2B SaaS with Insightpool, and the eventual creation of PrizePicks after enduring setbacks that would have stopped most founders in their tracks. He shares battle-tested lessons on resourcefulness, hiring with culture in mind, building when no one is watching, and maintaining momentum through uncertainty. This is a masterclass in entrepreneurial durability, from scrappy beginnings to strategic exits, told with honesty, clarity, and tactical wisdom.
Chapters: 02:20 – Discovering the Startup Bug During Birthright Trip 06:23 – Finding His First Technical Co-Founder 08:13 – Building GoRankem and the Power of Crowdsourced Music Discovery 11:57 – The Harsh Reality of Monetizing B2C 14:39 – Using Kickstarter Before Crowdfunding Was a Word 18:58 – Becoming the First Tech Startup to Raise on Kickstarter 22:04 – Resourcefulness and the Art of Bootstrapping 25:00 – Lessons From Chapter One: Necessity Breeds Hustle 28:27 – The Canoe Test and Hiring With Intention 31:41 – Culture as a Defensible Advantage 34:33 – The Birth of Insightpool and Enterprise B2B SaaS 39:45 – Spinning Up Multiple Ventures at Once 44:09 – Identifying Influencers and Building the Next Chapter 47:36 – Scaling Insightpool Through Enterprise Clients 51:10 – Transitioning From CEO to Chief Strategy Officer 55:12 – How Letting Go of Ego Opens Bigger Doors 59:24 – The Origin of PrizePicks and Pursuing B2C Upside 1:03:42 – The Collapse of Fantasy Sports in 2015 1:16:25 – Founding PrizePicks Amid Regulatory Turmoil 1:20:45 – Navigating COVID and Keeping the Business Alive 1:29:41 – The Barbados Offsite and the ClearCo Connection 1:36:04 – Reflecting on Legacy and Impact Post-Exit 1:39:43 – What’s Next: Not-for-Profit, Special Projects, and Brand Stewardship 1:43:34 – Advice to His Younger Self: Let Adversity Mold You
How Jamie Crozier is Modernizing a 90-Year-Old Industry With Risk, R&D and Vision
14 Jan 2026
00:59:16
In this episode of Founder2Founder, Aaron Spivak sits down with Jamie Crozier, owner of Thunder Bay Hydraulics and founder of Atlas Elite Autolifts. Jamie leads multiple industrial businesses based in Northern Ontario, including Custom Hydraulics, and has built a reputation for blending hands-on manufacturing with modern innovation. From hydraulic cylinder repair, to designing luxury car lift systems for high-end residential homes across North America, Jamie is reshaping what legacy manufacturing can look like today.
Jamie shares how he entered entrepreneurship later in life, stepping into a blue-collar industry with no formal business background and learning everything from the ground up. He breaks down how customer feedback led to the creation of Atlas Elite, why he’s taking bold R&D risks in a 90-year-old industry, and how family, partnership, and long-term thinking continue to shape the way he builds companies that last.
Chapters: 02:26 – Jamie’s Unexpected Path Into Entrepreneurship 03:36 – From Political Science to Sales and Industrial Supply 05:32 – The First Signals of Business Ownership 06:51 – The Role of His Wife and Business Partner 08:40 – Founding Atlas Elite Autolifts 10:07 – Identifying a Gap in the Luxury Car Lift Market 12:31 – Using Customer Feedback to Drive Design 13:24 – Early Mistakes With Construction Integration 15:36 – The Most Unique Projects They’ve Built 16:26 – Bringing a Car Lift Into a Living Room 18:24 – Engineering for High-Value Vehicles 19:17 – Growing Up in a Blue-Collar Household 21:06 – Why His Father Pushed Him Toward University 23:21 – Family, Motivation, and Staying Grounded 26:21 – Building a Business His Kids Can See 29:32 – Why Physical Businesses Still Matter 30:49 – Risk Tolerance as a Competitive Advantage 32:08 – Innovating Inside a 90-Year-Old Industry 34:10 – Designing for the Harshest Environments 37:02 – Where Hydraulics Is Headed Next 41:02 – Finding Purpose Later in the Journey 42:52 – The Power of an Outside Perspective 45:38 – Partnership, Belief, and Thinking Bigger 48:07 – Breaking Generational Limiting Beliefs 50:42 – Giving Back to the Northern Ontario Business Community 54:09 – Values, Integrity, and Choosing the Right People 56:17 – Commit Fully and Build With Intention
From Homeless and Burnout to a 7-Figure Ops Business Owner: Rebecca Kallaus on Starting Over
07 Jan 2026
00:55:32
In this episode of Founder2Founder, Aaron Spivak sits down with Rebecca Sunnen Kallaus, founder of Business Done Better and creator of the 5-Engine Operating System. With over a decade in business operations, Rebecca has helped companies from solo ventures to $20M+ scale with structure, clarity, and sustainability. She’s also played a direct role in shaping tools at HighLevel to better support founder-led businesses.
Rebecca shares the full story behind how she built her career, from working unpaid at a failing health clinic, to surviving financial collapse, homelessness, and personal trauma, all while launching her first business. She breaks down how she leaned into systems thinking, intuition, and self-trust to build a company that now supports some of the fastest-growing businesses in the space.
Chapters: 02:26 – Early Signs Of Entrepreneurship 03:36 – How Her Upbringing Shaped Her Drive 05:32 – Wanting Structure But Needing To Build It Herself 06:51 – Why She Wasn't Allowed To Work In School 08:40 – Choosing Psychology With No Real Plan 10:07 – Studying Holistic Health And Systems 12:31 – Saving Lives At A Wellness Clinic, But Not Getting Paid 13:24 – The First Major Financial Loss 15:36 – Moving To Hawaii And Taking Another Hit 16:26 – The Relationship That Taught Her Everything 18:24 – Losing $25k+ In One Year 19:17 – Starting Her First Business While Homeless 21:06 – Meeting A Mentor Who Saved Her Life 23:21 – The Moment Everything Began To Change 26:21 – The Power Of Reframing Good Vs Bad 29:32 – Losing Hope, And What Got Her Through 30:49 – Why A Clear “Why” Matters 32:08 – Her Deeper Purpose Behind Helping Founders 34:10 – Building Trust In Yourself 37:02 – Why Intuition Never Lies 41:02 – Breaking Down Her 5-Engine Operating System 42:52 – Why Most Founders Start Backwards 45:38 – Beating Out Major Players For Big Clients 48:07 – What She'd Tell Her Younger Self 50:42 – Finding Clarity In Silence 54:09 – Final Thoughts On Intuition, Momentum, And Rebuilding
Customer-Centric Leadership Lessons for Founders with Karen Quintos, Former Dell CMO
04 Feb 2026
01:07:18
In this episode of Founder2Founder, host Aaron Spivak sits down with Karen Quintos, former Chief Customer Officer and Chief Marketing Officer at Dell Technologies. Karen’s career spans multiple industries and decades of leadership at the highest levels, including Merck, Citibank, and Dell, where she led through some of the company’s most pivotal transformations. Known for her rare blend of operational rigor and soulful leadership, Karen opens up about navigating billion-dollar decisions while staying anchored in values, faith, and purpose.
Karen reflects on the defining moments that shaped her career, from managing 1,000+ manufacturing employees at age 30, to working directly with Michael Dell. She unpacks what it means to lead with authenticity, how she infused soul into a Fortune 500 brand, and why servant leadership, humility, and staying people-centered are her greatest assets. This episode is a powerful reminder that success doesn’t have to cost you your integrity and that leadership grounded in purpose can drive both performance and legacy.
Chapters: 02:42 – Growing Up on a Farm: Faith, Family and Hard Work 04:15 – Meeting Her Husband at Merck and Building a 40 Year Marriage 05:29 – Knowing She Wasn’t Meant to Be a Stay-at-Home Mom 07:21 – From Staff Role to Plant Manager: Learning Servant Leadership 09:48 – Early Mistakes, Union Threats and Listening to the Frontline 12:50 – Leaving Merck, Regretting Citibank and the Pivot to Dell 16:20 – How Karen Was Offered the CMO Role at Dell 18:11 – Why Michael Dell Chose Her: Customer-Centric Leadership 22:16 – Rebranding with Purpose: Tech for Good and Employee Alignment 23:15 – Internal vs. External Marketing: Why It Starts Within 27:07 – People First: Why Technology is a People Business 28:06 – Where Karen’s Soul-Driven Leadership Comes From 30:37 – Head vs. Heart: Operating with Conviction and Integrity 32:06 – Writing Her Book: You Can Be Successful Without Losing Your Soul 35:34 – Redefining Success at Every Stage of Life 37:49 – Playing the Long Game: Why Patience is Power 40:59 – The Knot in Your Stomach: Staying Curious and Grounded 42:28 – Learning from Leaders Around the Boardroom Table 45:52 – The Most Underrated Leadership Trait 47:55 – An Example of CEO Vulnerability and Transparency 51:04 – How Karen Supported Women Through Dell’s Entrepreneur Network 52:48 – Communities That Create Life-Changing Moments 55:14 – Why We Avoid the Environments That Will Help us Grow 57:52 – When the Same Knot Lingers: Making the Leap 58:44 – Advice to Her 13-Year-Old Self: Courage, Confidence Compassion 1:02:46 – Female Founders on Love, Marriage and Building Together
Gaurav Hundal on How Young Entrepreneurs Can Start Successful Businesses Before Age 20
11 Mar 2026
00:54:22
In this episode of Founder2Founder, Aaron Spivak sits down with Gaurav “Gord” Hundal, a 19-year-old real estate developer who has already flipped multiple homes and recently completed a luxury property listed for over $5 million in Fort Lauderdale. After experimenting with businesses like event promotion and clothing at a young age, Gaurav eventually found his passion in real estate development and house flipping.
Gaurav shares how discipline, strong family values, and relentless curiosity helped him transition from small renovation projects into the luxury real estate market. From navigating contractor mistakes to building trust in an industry dominated by older professionals, this conversation explores the mindset required to build credibility, take calculated risks, and stay committed to long-term growth.
Chapters: 02:10 – Growing Up Around Entrepreneurship and His First Business 03:10 – Throwing Underage Events and Early Hustle 04:25 – Launching a Clothing Brand as a Teenager 05:17 – Searching for Purpose Through Entrepreneurship 07:24 – Why Gaurav Still Attends College While Building Businesses 09:42 – The Social Value of School for Young Entrepreneurs 11:32 – Discovering Real Estate and His First House Flip 12:42 – How House Flipping Actually Works 14:38 – The Profit Potential of Real Estate Development 15:29 – Why Gaurav Transitioned Into Luxury Homes 17:29 – The $3.6M Luxury Property Investment 18:51 – Closing the Deal and Navigating Market Changes 19:49 – The Hard Lesson: Never Blindly Trust Contractors 21:06 – Systems Gaurav Uses to Avoid Getting Burned 22:28 – Why Honouring Deals Builds Long-Term Success 24:37 – The Role of Integrity and Karma in Business 26:33 – Overcoming Age Bias as a Young Entrepreneur 28:23 – Managing Real Estate Projects for Other Investors 29:46 – Why Reputation Is Everything in Real Estate 32:22 – Lessons Learned From Growing Up With Four Older Brothers 36:18 – The Discipline That Drives His Work Ethic 38:13 – Gaurav’s Daily Routine and Work Schedule 41:50 – The Importance of Obsession in Early Entrepreneurship 44:56 – Advice Gaurav Would Give His 14-Year-Old Self 47:38 – Handling Criticism, Doubt, and External Judgment 50:14 – Final Thoughts on Environment, Family, and Success
How CEOs Can Navigate Mental Health, Incentives, and Investor Alignment with David Balinski
04 Mar 2026
01:11:50
In this episode of Founder2Founder, Aaron Spivak sits down with David Balinski, Founder & CEO of Wire Health. With a background spanning risk management, pharmaceutical lobbying, national benefits consulting, and health plan M&A, David has built nine companies and dedicated his career to fixing one of the biggest failures in American healthcare: mental health access.
David shares the hard lessons he learned about partnerships, equity, incentives and culture, alongside a deep dive into the realities of mental health in entrepreneurship. From bipolar disorder among founders, to the limitations of SSRIs, emerging therapies like ketamine, and alternative healthcare strategies that have saved his family over $150,000. This conversation challenges how leaders think about responsibility, performance, and the systems supporting their teams.
Chapters: 01:08 – Why David Focused on Fixing Healthcare 02:42 – The Mental Health Gap in American Insurance 03:38 – Early Entrepreneurial Instincts and Lemonade Stands 05:20 – From Screenwriting Dreams to Health Insurance Underwriting 06:04 – The Hardest Lessons From Building Nine Companies 08:20 – The Cost of Trusting the Wrong People 09:11 – Why Giving Equity Too Early Is a Founder Mistake 12:43 – What to Do When a Key Employee Asks for Equity 14:30 – Building Advisory Boards That Protect You From Yourself 16:50 – Profit Share vs. Equity: A Smarter Alternative 18:47 – Incentives, Commission Structures, and Performance Culture 22:16 – Why Culture Is a Founder’s Real Job 25:26 – Blameless Problem Solving and Avoiding Toxic Behavior 28:02 – The Mental Health Reality Founders Don’t Talk About 30:01 – Bipolar Disorder in Entrepreneurs (4x the General Population) 32:02 – MDMA, PTSD, and Emerging Treatment Conversations 40:43 – Why Wire Health Sends Patients to Ketamine Treatment 45:37 – The 30% Problem With SSRIs 49:10 – Why David and His Family Don’t Use Traditional Health Insurance 55:21 – How Medical Sharing and Direct Primary Care Work 59:45 – Wire Health’s Employer-Focused Mental Health Model 1:01:30 – Choosing Investors Who Align With Your Mission 1:04:03 – The Recovery Friendly Workplace Movement 1:06:48 – Creating Psychological Safety at Work 1:10:16 – Final Reflections on Purpose, Impact, and Responsibility
How Founders Can Stop Losing A-Players and Start Building Ownership Culture with Michael C. Bertoni
25 Feb 2026
01:08:14
In this episode of Founder2Founder, Aaron Spivak sits down with Michael C. Bertoni, Founder and CEO of SaaS Talent, the global talent and growth engine behind hundreds of high-performing SaaS and tech companies. With over 25 years of experience helping founders scale revenue, build elite go-to-market teams, and turn hiring into a competitive advantage, Michael operates at the intersection of SaaS growth, recruiting, AI, and leadership.
Michael shares his journey from being a high-performing sales leader working for others to taking the leap into entrepreneurship at 39. He opens up about early mistakes, the mindset shifts that shaped his evolution, and why he believes every business challenge traces back to one core issue: talent. This conversation is a practical and honest look at what it really takes to scale a company through people, systems, and energy.
Chapters: 01:35 - The Origin of “The Rainmaker” 03:37 - Taking the Leap Into Entrepreneurship at 39 05:54 - Starting as a Solopreneur Without a Playbook 07:36 - Early Mistakes and Getting Kicked Out of Co-Working Spaces 10:25 - Self-Awareness and Evolving as a Founder 13:27 - Building a Personal Board of Advisors 18:01 - Inside SaaS Talent: Talent Acquisition and GTM Growth Coaching 19:48 - “Every Problem Is a Talent Problem” Explained 22:22 - How to Know If You Have the Right Person in the Right Seat 24:00 - Locking In A-Players Through Growth and Ownership 26:40 - The Founder’s Role: Bringing the Energy and Vision 30:09 - What Young Founders Should Look for in Talent 34:27 - Creating “Wow” Moments and Hiring Through Community 41:11 - Lessons from 20+ Years in SaaS and Tech 46:07 - Why You Need an Operating System to Scale 49:26 - Advice to His 13-Year-Old Self 52:07 - The Morning Routine That Changed His Leadership 55:13 - Gratitude, Manifestation, and Long-Term Growth 1:00:21 - Using LinkedIn as a Growth Engine 1:04:00 - Final Reflections and Building With Energy
How High-Performing Founders Can Rewire Trauma and Unlock Growth with Dr. Lisa Palmer
18 Feb 2026
00:55:54
In this episode of Founder2Founder, Aaron Spivak sits down with Dr. Lisa C. Palmer, PhD, LMFT, CHT, Program and Clinical Director of The Renew Center of Florida in Boca Raton, ranked #1 in the U.S. for PTSD treatment in 2017 by Newsmax. A nationally recognized psychotherapist featured on major networks including ABC, FOX, CNN, NBC, and CBS, Dr. Palmer works with celebrities, high-profile athletes, entrepreneurs, and public figures navigating trauma and high performance.
Dr. Palmer shares her journey from a traditional upbringing in Rhode Island to becoming one of Hollywood’s most trusted therapists. She opens up about early identity struggles, walking away from a promising television career, and the discipline that shaped her path. Together, Aaron and Dr. Palmer unpack how childhood experiences shape founders, how trauma impacts performance, and how re-scripting memories can unlock meaningful change.
Chapters: 01:27 - Dr. Lisa’s Early Life in Rhode Island 02:35 - Feeling Different and Early Identity Struggles 04:49 - Turning “Not Enough” Into Discipline and Drive 08:05 - The Influence of Rocky and Resilience 11:42 - Discovering Her Purpose to Make a Difference 12:40 - Working With High-Profile Clients and Trauma 14:37 - From Pre-Med to Miss USA Competitor 15:35 - Losing 60 Pounds and Winning by One Point 16:18 - Walking Away From a Promising TV Career 19:26 - Going Back to School and Pursuing Her Doctorate 22:22 - Realizing She Was Exactly Where She Belonged 23:27 - Re-Scripting Memories Explained 26:47 - How Trauma Gets Imprinted in the Brain 28:52 - Transforming Limiting Beliefs at the Root 31:39 - Why You Can’t Do This Work Alone 33:44 - Where Entrepreneurs Should Start With Inner Work 37:11 - Embracing Stillness and Self-Observation 41:07 - Handling the Emotional Weight of Clients 43:30 - Personal Reset Practices and Balance 47:26 - On Love, Growth, and What’s Still Unwritten 49:17 - What She Would Tell Her 5-Year-Old Self
Adrian Aidid on Building a $100M Acquisition Machine and a Life You’re Proud Of
11 Feb 2026
01:00:45
In this episode of Founder2Founder, host Aaron Spivak sits down with Adrian Aidid, Founder and CEO of LDX Digital, a top Google and YouTube Ads agency that manages over $11 million in monthly ad spend. Adrian is no stranger to scaling brands, he’s helped grow eight companies to over $100K/day in spend and engineered acquisition systems responsible for hundreds of millions in revenue. But before becoming one of the most respected operators in the performance marketing space, Adrian’s journey began in government housing in Bristol, England.
Adrian opens up about how growing up with a single refugee mother shaped his relentless drive, how a failed job transfer became the catalyst for his entrepreneurial breakthrough, and the exact steps he took to go from running Facebook ads for local shops to building one of the most trusted agencies for global e-commerce brands. He also shares the importance of giving without expectations and the unique infrastructure LDX builds to turn traffic into scalable, profitable growth. This is an unfiltered look at grit, clarity, and scaling with precision.
Chapters: 02:10 - Growing Up in Government Housing in Bristol 03:46 - Lessons from Watching His Mother Work 3 Jobs 05:10 - The “Death Ground” Mindset that Fueled Adrian’s Drive 06:32 - Getting Into Party Promotions and Sales in London 08:04 - The First Exposure to Marketing and Ad Agencies 09:25 - How The Alchemist Inspired a Move to NYC 11:14 - Entering Wall Street with No Network and High Stakes 15:15 - Environment Over Willpower: Why New York Changed Everything 16:54 - The “Come to Jesus” Moment After Getting Sent Back to the UK 20:58 - Starting From Scratch: Door-to-Door Sales for Local Businesses 23:26 - Getting His First Client and Making the Move to London 24:50 - Transitioning from Local to Ecomm and Making Real Money 26:18 - Pivoting Early to Google Ads Before iOS Updates Hit 28:45 - Scaling a Brand from Zero to $38M in 2 Years 30:22 - How LDX Builds Funnels, Pages, and Upsell Structures for Scale 32:07 - Google Compliance, Cold Traffic Mastery, and Platform Relationships 34:40 - Balancing Data and Intuition in Big Growth Decisions 38:36 - Giving Without Expectation and Why It Works 41:59 - Building Relationships Without ROI Expectations 44:16 - Miami, Culture, and Creating the Right Environment to Thrive 46:59 - How Community Shapes Outcomes and Reduces Isolation 48:40 - The Power of Proximity and Being Around the Right People 50:13 - What Adrian Would Tell His 19-Year-Old Self 52:44 - Why Founders Need to Prioritize Character, Not Just Skills 55:08 - The Ultimate Test: Would You Grab a Beer With Them? 56:27 - Why Vibes and Energy Matter More Than Credentials