In this insightful conversation, the host sits down with Scott Sheridan, CEO of TastyTrade and co-founder of the revolutionary trading platform Thinkorswim, who shares his decades of experience navigating volatile markets and building successful financial technology companies.

Scott discusses his contrarian approach to current market trends, explaining why he remains skeptical of popular investments like cryptocurrency and gold while emphasizing the importance of options trading during periods of high volatility like we're experiencing now.

The interview explores Scott's entrepreneurial journey from floor trader at the Chicago Board Options Exchange to creating two major brokerage firms, focusing on how he built strong company cultures and the critical importance of timing, team building, and maintaining vision while staying flexible enough to pivot when necessary.

Scott and the host delve into practical investment strategies for uncertain times, with Scott advocating for consistent market participation through dollar-cost averaging and his current preference for selling puts in quality stocks during high-volatility periods.

Key Takeaways:
* Trade small and trade often - consistent market participation with manageable risk beats trying to hit home runs, especially for those just starting their investment journey
* Focus on what you can control and maintain strong risk management - whether in trading or business, calculate your risks and never invest more than you can afford to lose
* Build businesses and hire teams based on trust and complementary skills - successful partnerships require people you'd trust with your financial future, and company culture flows from authentic leadership rather than corporate buzzwords

Head over to podcast.iamcharlesschwartz.com to download your exclusive companion guide, designed to guide you step-by-step in implementing the strategies revealed in this episode.

KEY POINTS:
02:34 - From floor trader to tech pioneer: How Scott transitioned from trading at the Chicago Board Options Exchange to co-founding Thinkorswim, revolutionizing online trading by creating sophisticated platforms that retail investors could actually use.
05:35 - Why this market crash was different: Scott explains how the recent volatility was completely self-induced by political decisions, making it unlike previous crashes and creating unique opportunities for prepared traders.
06:09 - The young investor's advantage: Why people in their 20s and 30s need to take significant risks and stay engaged with volatile markets, since they have 40-year time horizons that virtually guarantee higher returns.
13:01 - The psychology of trading size: Scott's gambling wisdom about getting opponents to play for more than they're comfortable with, and how to know immediately if you're trading too big by your physical reaction.
35:00 - Selling flood insurance after the flood: Scott's current strategy of selling puts during high volatility periods, explaining how elevated option premiums create profit opportunities for patient investors.
39:40 - Building culture through trust: How Scott creates family-like company environments by challenging employees beyond their comfort zones while promising that any mistake can be fixed with time and money.
52:54 - The entrepreneur's regret insurance: Scott's passionate plea to anyone considering starting a business - the worst outcome is working for someone else again, but the regret of never trying lasts a lifetime.

In this revealing conversation, Charles sits down with Amanda Dopler, a successful health coach who built a seven-figure business entirely on her own.

Amanda shares her journey from struggling with yo-yo dieting to creating a health coaching empire that generates six figures monthly, highlighting how authenticity and consistency drove her success in an oversaturated market.

The interview dives into Amanda's unique approach to both business and weight loss, focusing on sustainable habits rather than quick fixes, and how she managed to build a thriving community despite starting with just her phone and basic tools.

Charles and Amanda explore the realities of entrepreneurship, with Amanda candidly discussing the challenges of scaling a one-person operation and the importance of believing in yourself when others doubt your vision.

Key Takeaways:
* How authenticity and blunt honesty helped Amanda stand out in the crowded health coaching industry
* Why focusing on client testimonials and real transformations was her most effective marketing strategy
* The power of creating a supportive community that becomes the most valuable part of your offering
* Why entrepreneurial success requires eliminating "Plan B" thinking and committing fully to your vision

Head over to podcast.iamcharlesschwartz.com to download your exclusive companion guide, designed to guide you step-by-step in implementing the strategies revealed in this episode.

KEY POINTS:
02:54 - Disrupting the diet industry: How complete honesty about eating whatever you want while still losing weight created a breakthrough approach in a market filled with unnecessary restrictions and quick-fix promises.
07:16 - The long-term mindset: Why putting your head down and focusing on who you want to become rather than overnight success created the foundation for sustainable seven-figure growth.
12:15 - The engagement revelation: Building a $75,000 monthly business with just 5,000 followers by prioritizing deep audience connection over vanity metrics that rarely convert to actual revenue.
15:43 - The solo empire builder: The behind-the-scenes reality of managing every aspect of a million-dollar business alone – from social media and coaching to operations and customer service.
27:42 - The testimonial blueprint: How showcasing the complete transformation story with specific pain points and sustainable results converts dramatically better than oversimplified before-and-after narratives.
32:42 - The community advantage: When the unexpected value proposition became the supportive network of clients rather than one-on-one coaching, despite initial resistance to group formats.
40:16 - The entrepreneur's ultimatum: Why having absolutely "no plan B" and viewing corporate employment as completely unacceptable creates the determination required to overcome inevitable obstacles.

In this insightful episode, Charles explores the entrepreneurial journey and personal resilience with Bobby Mesmer, founder and CEO of RMG Erectors & Constructors, LLC, now valued at $4.5 billion.

Bobby reveals his path from bootstrapping his business to building one of the largest steel erection companies in the world, sharing how multiple life-threatening health crises transformed both his personal outlook and business approach.

The conversation shifts from business strategies to profound personal reflection as Bobby opens up about facing mortality through multiple strokes and a heart attack that left him partially disabled and questioning his worth as a leader, husband, and father.

Rather than focusing solely on business tactics, Charles and Bobby explore how vulnerability and self-belief become essential components of both personal recovery and business growth.
Together, they challenge conventional entrepreneurial wisdom, emphasizing that true success comes from learning from failures and sharing those lessons with others—what Bobby calls paying the "dummy tax."

Key Takeaways:
* Why bootstrapping creates more resilient business owners than seeking venture capital
* How near-death experiences can reveal your true purpose in business and life
* The operational excellence formula that transformed Bobby's company into an industry leader
* How embracing personal vulnerability after health setbacks can become an unexpected source of strength

Head over to podcast.iamcharlesschwartz.com to download your exclusive companion guide, designed to guide you step-by-step in implementing the strategies revealed in this episode.

KEY POINTS:
02:13 - The Dummy Tax Philosophy: Bobby explains his core business philosophy: "Dummy tax. I made the mistakes learned from me, right? Like, and you know, it started anybody in business, if you're not failing, you should be because that's the only way you're learning."
06:00 - The Scale of Success: Bobby reveals the impressive scale of his business achievements: "We develop that business into also manufacturing and engineering and design... We're the largest purchaser of fabricated steel in North America."
09:44 - The Problem with VC Funding: Bobby shares his strong view on bootstrapping vs. seeking investors: "When you take on capital, the problem with that is, is you're creating a crutch with the capital you're taking on because you're not going through the heartache of running a business and learning how to grow."
13:01 - The True Entrepreneur Test: Bobby explains how to identify real entrepreneurs: "It's very simple. What are you doing in the face of diversity? It starts there. When that adversity hits you, what are your actions? Either you're sticking your head in the sand or you're pulling yourself by your bootstraps."
35:53 - The Health Crisis Reality: Bobby opens up about his devastating health challenges: "When I had my stroke, I lost a whole left side of my body, like I couldn't move my face... that was the first time in my life, like, I felt real fear, you know, like, I was like, holy shit, like, this is, this is real."
37:46 - Wrestling with Unworthiness: Bobby reveals his deeper struggles after health setbacks: "You have a lot of, you know, self-awareness that comes about you through that... You start to question things and you go through so many emotions of, you know, am I really the strong? Should I really be doing this? I'm not worthy? I'm not good enough for my wife. I'm not good enough for my kids."
50:02 - Finding Purpose Through Pain: Bobby shares how he found meaning after his health crises: "I have more to do. I have more to do. I know that I've been gifted with a gift in a lot of ways. I've been gifted with a gift that I need to give back to people... if my survival through what I went through is that gift that I need to give back, that I need to give that back until it's done."