Founder2Founder with Aaron Spivak

In this episode of Founder2Founder, Aaron Spivak sits down with Addison LaBonte, founder of Sweet Addison’s, a fast-growing better-for-you bakery shipping gluten-free, dairy-free desserts nationwide. A former Division 1 athlete, Addison has channeled her discipline and resilience into building a brand rooted in authenticity and quality.After a life-changing health diagnosis, Addison turned to gluten-free living, what started as a personal journey quickly evolved into a thriving business and loyal online community. Her story highlights the power of betting on yourself, building with intention, and creating products that truly serve people.Chapters01:16 – Addison’s Background and Unexpected Path to Entrepreneurship03:42 – How Division 1 Athletics Shaped Her Discipline and Mindset05:41 – The Power of Delayed Gratification in Business07:44 – Health Diagnosis That Changed Everything08:35 – Discovering Gluten-Free Living and a New Passion09:49 – Starting an Instagram Account That Led to a Business11:03 – Early Doubts and Getting Laid Off Before Launch12:33 – Building Sweet Addison’s From a Small Apartment13:25 – 26 Recipe Iterations to Perfect the Product14:10 – Transitioning From Home Baking to a Commercial Kitchen15:13 – Listening to Customers and Building for Demand17:53 – Launch Strategy: Influencers and Word-of-Mouth Growth18:44 – Understanding the Gluten-Free Consumer Market20:08 – Product Innovation: High-Protein, Better-For-You Desserts21:31 – Challenges of Selling Perishable Products Online23:13 – Vision for Scaling Into National Retail25:34 – Why Personal Branding Was a Game-Changer27:37 – Discipline, Consistency, and Social Media Growth29:59 – Evolving Her Personal Brand Over Time31:26 – Viral Content and Learning From Audience Feedback36:32 – Pushing Limits: From Marathons to Ultra Running38:17 – The “Deathbed Mentality” and Living Without Regret40:43 – Training the Mind Through Physical Challenges42:55 – Childhood Lessons That Built Independence and Resilience47:16 – Taking a Leap of Faith and Moving to Dallas50:45 – Advice to Her Younger SelfGuest Links:Website: www.sweetaddisons.comInstagram: @sweet.addisons@organicallyaddisonThe Founders Club: The premier community for founders pursuing excellence in the mind, body, and business.Stay Connected!Aaron Spivak:IG: @‌SpivakLinkedinThe Founders ClubIG: @‌TheFoundersClubWebsite www.foundersclubofficial.com Founder2Founder:TikTok @‌Founder2FounderPodcastYoutube @‌Founder2Founder.Podcast

In this episode of Founder2Founder, Aaron Spivak sits down with Jamie Maltabes, Founder and CEO of Infinite Medical Group, a rapidly growing wellness and regenerative medicine company. Jamie’s journey to entrepreneurship was shaped by years of personal struggle, addiction, recovery, and a relentless commitment to rebuilding her life and helping others do the same.Jamie shares how hitting rock bottom in her twenties forced her to completely transform her life, ultimately leading her to build a business rooted in real impact. From navigating addiction and high-stakes poker to launching a wellness company from a basement side hustle, her story is a powerful reminder that some of the strongest founders are forged through adversity and reinvention.Chapters 01:20 – Jamie’s Earliest Memory of Leadership and Truth-Telling 04:00 – Struggling With Food, Body Image, and Early Eating Disorders 06:38 – Addiction to Alcohol, Drugs, and the Cycle of Self-Destruction 09:48 – The Moment That Led Jamie to Alcoholics Anonymous 10:21 – Rebuilding Life Through Recovery and Personal Discipline 12:13 – Channeling Addiction Into AA and New Obsessions 13:12 – Discovering Poker and Entering the High-Stakes Card World 16:07 – Running Private Poker Games During COVID 17:09 – The Realization That Forced Jamie to Walk Away From Poker 18:42 – The Power of Environment and Finding the Right Circles 20:25 – Divorce, Leaving Poker, and Career Transition 21:10 – Building Leadership Experience at HairClub 22:27 – Losing Money in a Business Dispute and the Push to Start Over 23:00 – The Birth of Infinite Medical Group 26:37 – Discovering Ozempic and Its Impact on Weight Management 28:37 – Launching a Wellness Side Hustle From Her Basement 29:05 – Turning a Side Hustle Into a Scalable Medical Business 30:12 – The Unexpected Challenges of Launching a Medical Clinic 31:16 – Why Speed and Execution Drive Infinite’s Growth 32:57 – Expansion Plans and Balancing Business With Family 34:46 – Psychedelic Therapy, Healing, and Personal Growth 41:14 – Entrepreneurship as a Personal Development Journey 43:04 – Leading With Purpose and Building a Positive Team Culture 44:10 – Advice Jamie Would Give Her 24-Year-Old Self 46:54 – The Power of Pivots and Never Quitting the GameGuest Links:|Website: https://infinitemedicalgroup.comInstagram: @infinitemedicalgroup @jamiemaltabesThe Founders Club: The premier community for founders pursuing excellence in the mind, body, and business.Stay Connected!Aaron Spivak:IG: @‌SpivakLinkedinThe Founders ClubIG: @‌TheFoundersClubWebsite www.foundersclubofficial.com Founder2Founder:TikTok @‌Founder2FounderPodcastYoutube @‌Founder2Founder.Podcast

In this episode of Founder2Founder, Aaron Spivak sits down with 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 SuccessGuest Links:Instagram: https://www.instagram.com/gauravhundalll/The Founders Club: The premier community for founders pursuing excellence in the mind, body, and business.Stay Connected!Aaron Spivak:IG: @‌SpivakLinkedinThe Founders ClubIG: @‌TheFoundersClubWebsite www.foundersclubofficial.com Founder2Founder:TikTok @‌Founder2FounderPodcastYoutube @‌Founder2Founder.Podcast

In this episode of Founder2Founder, Aaron Spivak sits down with 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 ResponsibilityGuest Links: Website: https://wire.health/LinkedIn: David Balinski Wire HealthThe Founders Club: The premier community for founders pursuing excellence in the mind, body, and business.Stay Connected!Aaron Spivak:IG: @‌SpivakLinkedinThe Founders ClubIG: @‌TheFoundersClubWebsite www.foundersclubofficial.com Founder2Founder:TikTok @‌Founder2FounderPodcastYoutube @‌Founder2Founder.Podcast

In this episode of Founder2Founder, Aaron Spivak sits down with 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 EnergyGuest Links: Website: https://www.saas-talent.com/LinkedIn: Michael C. BertoniThe Founders Club: The premier community for founders pursuing excellence in the mind, body, and business.Stay Connected!Aaron Spivak:IG: @‌SpivakLinkedinThe Founders ClubIG: @‌TheFoundersClubWebsite www.foundersclubofficial.com Founder2Founder:TikTok @‌Founder2FounderPodcastYoutube @‌Founder2Founder.Podcast

In this episode of Founder2Founder, Aaron Spivak sits down with 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 SelfGuest Links:Website: www.myrenewme.com https://www.therenewcenter.comInstagram: @drlisapalmer @myrenewme The Founders Club: The premier community for founders pursuing excellence in the mind, body, and business.Stay Connected!Aaron Spivak:IG: @‌SpivakLinkedinThe Founders ClubIG: @‌TheFoundersClubWebsite www.foundersclubofficial.com Founder2Founder:TikTok @‌Founder2FounderPodcastYoutube @‌Founder2Founder.Podcast

In this episode of Founder2Founder, 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 CredentialsGuest Links:Website: https://www.ldxdigital.comLinkedIn: Adrian AididThe Founders Club: The premier community for founders pursuing excellence in the mind, body, and business.Stay Connected!Aaron Spivak:IG: @‌SpivakLinkedinThe Founders ClubIG: @‌TheFoundersClubWebsite www.foundersclubofficial.com Founder2Founder:TikTok @‌Founder2FounderPodcastYoutube @‌Founder2Founder.Podcast

In this episode of Founder2Founder, 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 TogetherGuest Links:Instagram: KarenhquintosLinkedIn: Karen QuintosTwitter: KarenhquintosThe Founders Club: The premier community for founders pursuing excellence in the mind, body, and business.Stay Connected!Aaron Spivak:IG: @‌SpivakLinkedinThe Founders ClubIG: @‌TheFoundersClubWebsite www.foundersclubofficial.com Founder2Founder:TikTok @‌Founder2FounderPodcastYoutube @‌Founder2Founder.Podcast

In this episode of Founder2Founder, Aaron Spivak 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 purposeChapters:01:03 – The Truth About Founders Who Break Through02:08 – Why Clarity and Focus Beat Chaos03:47 – Avoiding Shiny Object Syndrome in 202605:25 – The Anxiety That Comes from Lack of Vision06:44 – 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 Multichannel11:00 – Are You Testing a Channel or Building It?12:51 – The Difference Between Committing vs. Experimenting14:06 – The Real Reason Founders Don’t Go All In17:01 – Creating Feedback Loops to Build Momentum19:05 – Why Small Wins Shouldn’t Be Overlooked20:01 – Founder Bottlenecks and How to Eliminate Them22:04 – Panic Execution Is a Sign of Broken Systems23:42 – Giving Teams Ownership of Their "Piano"25:12 – The Power of Real-World, In-Person Connection26:10 – Your Network is Who Picks Up the Phone When It Gets Hard28:08 – Give First: The Foundation of True Founder Relationships30:02 – What Real Founder Support Looks Like33:58 – Why Your Circle Defines Your Trajectory35:35 – AI is Leverage, Not Leadership42:03 – AI for Speed and Margin, Not for Connection44:58 – Clear Strategy, Committed Team, One Goal48:35 – Inside the Vision for Founders Club 202651:17 – Why Integrity is Everything as You Scale53:24 – Designing Events That Actually Serve Founders56:09 – The Power of Physical Spaces in a Digital World58:10 – Are We Building Community the Right Way?1:06:30 – Why Gender-Specific Events Are Unlocking Deeper Growth1:08:00 – Founders Forum LA: Our Biggest Event Ever1:11:45 – Redefining Sponsorships to Actually Add Value1:14:06 – The New Perks Members Actually Use1:16:22 – 2025 Was Chaos, 2026 is ClarityGuest Links: Instagram @chrismeade & @crossnetgameWebsite: https://vivereltd.com/pages/crossnetThe Founders Club: The premier community for founders pursuing excellence in the mind, body, and business.Stay Connected!Aaron Spivak:IG: @‌SpivakLinkedinThe Founders ClubIG: @‌TheFoundersClubWebsite www.foundersclubofficial.com Founder2Founder:TikTok @‌Founder2FounderPodcastYoutube @‌Founder2Founder.Podcast

In this episode of Founder2Founder, Aaron Spivak sits down with 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 YouGuest Links:Website: https://www.prizepicks.com/ https://thehiddenjams.org/Instagram: @thewordpainterLinkedIn: Adam WexlerThe Founders Club: The premier community for founders pursuing excellence in the mind, body, and business.Stay Connected!Aaron Spivak:IG: @‌SpivakLinkedinThe Founders ClubIG: @‌TheFoundersClubWebsite www.foundersclubofficial.com Founder2Founder:TikTok @‌Founder2FounderPodcastYoutube @‌Founder2Founder.Podcast