The Hidden Entrepreneur Show with Josh Cary

Crypto Taxes, NFTs, and the IRS: What Every Investor Needs to Know

Cryptocurrency has opened the door to a new financial frontier. Bitcoin, Ethereum, NFTs, DeFi trades. For many investors it has created opportunity, excitement, and yes… confusion. Especially when tax season arrives.In this episode of The Hidden Entrepreneur Show, host Josh Cary sits down with Janna Scott, founder of DeFi Tax, to unpack one of the most misunderstood areas of modern finance: how cryptocurrency is actually taxed in the United States.If you have ever bought, sold, traded, or even experimented with crypto or NFTs, this conversation is essential listening. Janna explains why the IRS rules around crypto taxation are actually clearer than most people believe. The real problem lies in the data, the reporting tools, and the platforms investors rely on.Drawing from years of research, audits, and direct conversations with government agencies, Janna reveals surprising gaps in the current crypto tax ecosystem and why many investors may unknowingly be reporting inaccurate information. She also explains how her work aims to bring transparency and accuracy to a rapidly evolving space.This episode is a must listen for crypto investors, entrepreneurs, and anyone trying to stay compliant while navigating the fast moving world of digital assets.What You’ll Learn in This EpisodeHow the IRS Actually Treats Cryptocurrency Why the IRS views crypto the same way it views stocks, real estate, or other assets and why many investors misunderstand the tax implications of their trades.The Real Problem With Crypto Tax Reporting Why the biggest issue is not IRS regulations but the way exchanges, blockchains, and reporting platforms collect and interpret transaction data.Why Crypto Tax Platforms Often Produce Different Results Janna reveals her research analyzing multiple crypto tax software platforms and why the same data set can produce wildly different tax outcomes.The Truth About 1099-DA Reporting What the new reporting forms mean for taxpayers and why many investors could end up over-reporting gains if they rely on inaccurate calculations.How Investors Can Accidentally Commit Fraud A surprising look at how some crypto tax platforms allow users to manipulate transaction categories and data, sometimes without realizing the legal implications.The IRS Audit Reality for Crypto Investors What happens when the IRS flags discrepancies between reported gains and exchange data and how automated audits may impact crypto users in the coming years.The Entrepreneurial Journey Behind DeFi Tax How Janna Scott left government consulting, built a tax firm, and went down a deep research rabbit hole that eventually led her to create a new solution for crypto tax reporting.

All the Rage: Venessa Peruda on Female Anger, Comedy, and Creative Freedom

What if anger is not the problem? What if the real problem is being taught to suppress it?In this thought provoking episode, Josh Cary sits down with Venessa Peruda, creator, writer, and performer of the one woman show All the Rage, to explore the emotional, creative, and cultural power of anger, especially female anger. This is a rich conversation about performance, storytelling, comedy, healing, and what happens when people finally stop apologizing for what they feel.Venessa shares how comedy became her outlet, her coping mechanism, and ultimately her creative weapon. She opens up about the social conditioning that teaches women to silence their anger, why that suppression can be harmful, and how humor can transform pain into something powerful, connective, and even liberating.If you care about personal growth, emotional expression, live performance, comedy writing, women’s empowerment, or the deeper truth behind creative work, this episode delivers. It is part artistic exploration, part emotional wake up call, and part invitation to stop swallowing what needs to be said.What You’ll Learn in This EpisodeWhy female anger is often suppressed Venessa breaks down the social conditioning that teaches women to view anger as shameful, disruptive, or unacceptable and why that conditioning needs to be challenged.How comedy becomes a survival tool You’ll hear how humor can help process difficult experiences, navigate pain, and create connection in the middle of chaos.The real mission behind All the Rage This is not just a comedy show. Venessa reveals why she sees it as an educational, liberating, and emotionally charged experience that invites women to rethink their relationship with anger.How anger can become useful energy Instead of seeing anger as something dangerous or destructive, Venessa explains how it can become a catalyst for truth, action, creativity, and personal freedom.Why performance and comedy are such difficult art forms Josh and Venessa explore the challenge of writing, performing, and landing comedy in real time, where the feedback is instant and every word matters.How laughter creates power over pain One of the strongest ideas in this episode is that comedy is a kind of alchemy. It can take rage, hurt, and injustice and turn them into release, perspective, and strength.Why creative expression can be deeply healing From stand up to sketch work to one woman shows, this conversation highlights how storytelling and performance can become tools for emotional release and self reclamation.

Is the Healthcare System Actually Broken? A Liver Transplant Survivor Thinks So.

If you have ever hesitated to call a doctor because you were worried about the bill… this episode will hit home.Jeff Dewey, Founder and CEO of Hope Delivered Health Provided, collapsed in his front yard in 2023. He needed a liver transplant. And in that terrifying moment, he was more worried about the cost than saving his own life.That fear changed everything.In this powerful conversation, we explore what is actually broken in the American healthcare system, why high deductible plans are overwhelming more than 150 million Americans, and how Jeff’s company is working to reduce employer costs while eliminating fear for employees.But this is more than a healthcare episode.It is a story about ego, awareness, responsibility, and what happens when a 13 year old who wanted to be a Zen monk grows up to challenge billion dollar systems.If you are a business owner navigating rising healthcare costs, an employee confused by your benefits, or simply someone who has felt frustrated by the system, this conversation offers both clarity and hope.What You’ll Learn in This EpisodeWhy Healthcare Costs Keep Rising Jeff breaks down why healthcare continues to climb as a percentage of GDP and why small tweaks to the system are not solving the real problem.How High Deductible Plans Impact 153 Million Americans What these plans mean for employees and employers, and why so many people delay care because of cost uncertainty.The Fear Factor in Healthcare Why Jeff hesitated to call 911 during a life threatening moment and how eliminating financial confusion can eliminate emotional panic.How Hope Delivered Health Provided Works How the company helps employers reduce healthcare expenses by 15 to 40 percent while giving employees better access, better education, and greater financial clarity.The Entrepreneurial Leap After a Health Crisis Jeff’s path from international basketball agent to financial professional to healthcare founder and how each chapter shaped his mission.Zen, Ego, and Leadership How a teenage desire to become a Zen monk shaped Jeff’s approach to competition, empathy, negotiation, and business leadership.Accumulation vs Debt in Life A powerful metaphor comparing emotional reactions and personal responsibility to financial accumulation and debt.The Hidden Entrepreneur Connection A raw discussion about regulating emotional reactions, taking responsibility, and how personal transformation fuels professional impact.

Why Big Media Can Hurt Your Business If You’re Not Ready with Kristan Vermeulen

What happens when a publicist loses her entire business overnight and decides to build something bigger instead?In this episode, Josh sits down with Kristan Vermeulen, creator of Makers of the USA, a show and media platform that highlights entrepreneurs and creatives who build with their hands and lead with heart. What started as a simple podcast during COVID quickly evolved into a visually rich, travel-style show that has caught the attention of major media outlets and streaming platforms.This conversation goes far beyond podcasting. It is about reinvention, vulnerability, storytelling, and what it really takes to be ready for visibility. Whether you are an entrepreneur, executive, creative, or leader trying to tell your story in a crowded world, this episode will challenge how you think about personal brand, PR, and being seen.What You’ll Learn in This EpisodeWhy Makers of the USA Is Not Just a Podcast Kristan explains how the show became a full storytelling platform designed for television, streaming, and long-form visual media, and why that distinction matters if you want real reach and longevity.How Losing Everything Can Spark the Right Idea After COVID shut down her PR business, Kristan used the moment to create something aligned with her values. This episode shows how disruption can become direction if you listen closely.The Power of Long Form Storytelling Why podcasts and unscripted conversations reveal what short articles and headlines never can and how depth builds trust with an audience.What Most Entrepreneurs Get Wrong About PR and Media Getting featured is not enough. Kristan breaks down why being visible without being prepared can actually hurt your business and what must be in place before big opportunities arrive.How to Find the Story People Actually Care About The hidden nuggets, personal moments, and life experiences that make someone memorable, and why your resume alone is never the story.Personal Brand for Leaders and Executives Why storytelling is not optional for leadership anymore and how being human makes people care about what you do.From Miss Maine to National Media Kristan shares the unexpected story of competing in pageants to showcase American made products and how unconventional choices can create powerful press angles.Confidence, Vulnerability, and Being Ready to Be Seen The internal work that must happen before the external opportunities can work in your favor.What It Really Takes to Be Ready for National Exposure Inventory, messaging, clarity, and systems. Why media attention should be earned intentionally, not chased impulsively.

Watching Everyone Else Win While You Start Over with John Bunzel

Reinvention sounds sexy on Instagram.In real life, it usually starts with loss, shame, fear, and the quiet realization that the dream you chased for decades is no longer working.In this episode of The Hidden Entrepreneur Show, Josh Cary sits down with John Bunzel for a raw and deeply human conversation about identity, ambition, and what it actually takes to rebuild your life when the original plan collapses.John’s story is not a highlight reel.Juilliard-trained actor.Successful playwright and screenwriter.Studio deals. Writers strikes. Hollywood politics.Then a complete pivot into movie finance, executive leadership, and eventually wealth management.This is not a story about quitting.It’s a story about choosing a future over an ego.If you are at a crossroads in your career, quietly questioning your path, or carrying shame about a dream that did not pan out, this conversation will hit home.What You’ll Learn in This EpisodeWhy Reinvention Often Requires Something to DieJohn explains why true reinvention is not about adding skills. It is about letting go of a former identity and being willing to grieve it.When the World Is Telling You It’s Time to PivotFrom studio heads getting fired to writers strikes shutting everything down, John shares how repeated external roadblocks can be signals rather than failures.The Dark Side of Chasing DreamsShame. Jealousy. Financial stress. Watching peers succeed while you feel stuck. John speaks honestly about the emotional toll of staying too long in the wrong chapter.Confidence, Creativity, and Why Pressure Kills BothWhy writers, creators, and leaders lose their edge when fear and survival replace belief, and how that loss shows up in performance.Identity Shifts Are the Hardest PartGoing from artist to executive. From creative to CFP. John breaks down why changing who you are in the world is far harder than learning a new skill.Why Letting Go Is Not Failure“It’s okay to let go of your dreams, as long as you dream new ones.” This episode reframes quitting as courage when done intentionally.What “Failure Is Not an Option” Actually MeansWhen responsibility, family, and reality collide, John explains how necessity forged a level of courage he never had before.Why Wealth Managers Are Not BoringA Juilliard-trained actor turned financial planner proves that lived experience, storytelling, and humanity matter more than job titles.