Charles goes one on one with David Goldhill, founder and CEO of Sesame, former president of television at Universal Studios, and author of Catastrophic Care, to tear apart why American healthcare costs so much and what it would actually take to fix it.

They walk through why the United States covers 40 percent of the world's healthcare spending while making up just 3 percent of the population, why insurance companies and government payers killed normal pricing, and why the fix isn't one big policy swing. It's a shift back to treating patients like customers.

The conversation covers the real economics behind a $900 million pill, why Sesame borrows its pricing model from a stone crab restaurant in Miami, why hospitals are stuck with a broken business model, and why the doctor in your neighborhood is about to compete with the best doctor on the planet.

KEY POINTS: 00:34 – Entertainment executive to healthcare founder: David walks through his path from Universal Studios and the Game Show Network to building Sesame, and why Charles calls it a classic swap from one broken industry to another. 01:57 – America is subsidizing world healthcare: David explains why the US pays 70 to 80 percent of the cost of medical innovation while capturing a fraction of the benefit, and why cutting that funding would collapse care standards everywhere. 04:04 – The NATO of medicine: David compares American healthcare spending to defense spending in NATO, and lays out the number that stops most people cold. The US is 3 percent of world population and 40 percent of world healthcare spend. 09:13 – Why the first pill costs $900 million and the second costs a penny: Charles and David break down drug pricing, and why a business model that looks terrible everywhere else works in healthcare because normal competition never gets the chance to bring prices down. 14:42 – The real lifetime cost of healthcare: David shares the number that shocked him while writing his 2012 book, what one employee puts into the healthcare system over a lifetime, and where all of that money actually goes. 27:30 – The Joe's Stone Crab model: Charles and David use a Miami restaurant to explain how Sesame built a cash pay system that gives patients upfront pricing without insurance, and why doctors are lining up to join it. 31:33 – Telemedicine breaks the map: David explains why location is about to stop deciding who gets access to the best doctors, and how remote care strips real cost out of the system instead of just shifting it around. 37:05 – What happens when incentives go wrong: Charles shares a story from his years in hospice about a system that started rewarding shorter patient stays, and David explains why neither side of that story is really about good or evil people. 44:11 – The biggest shifts in the market right now: David breaks down why patients are getting more financially sophisticated, why doctors are leaving independent practice, and why big hospital chains are structurally unable to compete on cost. 52:09 – Fighting conventional wisdom: David walks through the assumptions people in healthcare kept telling him were impossible, like doctors posting real prices, and why more of the best doctors in the country are asking how to get out of insurance entirely.

KEY TAKEAWAYS:

• Why the US being 3 percent of world population and 40 percent of world healthcare spend is the number that explains almost everything else in this conversation
• How third party payers removed the pressure that normally pushes prices down as a product matures
• Why Sesame's cash pay, upfront pricing model is pulling in doctors who are tired of spending their time on insurance paperwork
• Why hospitals keep growing their share of the healthcare dollar even though they play a shrinking role in actual care
• Why personalized, proactive healthcare cannot run on a payment system built for a world where medicine could only react to problems after they happened

Charles sits down with Mark Roberge, tech entrepreneur, Harvard Business School professor, and founding Chief Revenue Officer of HubSpot, to break down what AI is actually doing to sales, scaling, and the way companies get built.

From the real numbers behind AI adoption to the frameworks that separate companies that scale successfully from the ones that stall out, Mark shares why growth isn't about working harder. It's about measuring the right things before you push the gas.

Together, they dive into the four phases of AI in the workplace, why chasing revenue too early can kill product market fit, how big companies survive disruption by cannibalizing themselves first, and why mental health still gets treated differently than physical health in business. This isn't just a conversation about AI or sales. It's a blueprint for scaling smarter, staying human while everything speeds up, and building a company that lasts past the next hype cycle.

KEY TAKEAWAYS:

• How Mark Roberge built HubSpot's revenue engine from the ground up and turned that experience into a framework other companies now use to scale
• Why measuring selling time and rep to manager ratios says more about AI adoption than any buzzword does
• The difference between chasing revenue and building real product market fit rooted in customer retention
• How Salesforce, Workday, and ServiceNow beat established leaders by building something new instead of protecting what they already had
• Why venture capital isn't the right path for most founders, and how to know if it's the right one for you

KEY POINTS:

00:25 – From HubSpot's first salesperson to Harvard professor: Mark walks through building HubSpot's revenue engine as founding CRO through IPO, teaching sales at Harvard Business School, and launching Stage 2 Capital, while Charles points out how far the same starting line can take two different people.

02:53 – The four phases of AI in sales: Mark breaks down how AI moves from clearing out busywork to fully autonomous agents on both sides of a deal, while Charles pushes him to define what being AI enabled actually means beyond the buzzwords.

13:18 – Comparing AI to the biggest shifts in human history: Mark compares the AI transition to humanity's move from nomadic life to agriculture and from feudalism to democracy, while Charles connects it to how badly people misjudged the internet's arrival.

25:24 – Turning scaling into a science: Mark explains why most founders decide to scale off gut feeling instead of data, while Charles pushes him for the exact numbers that separate a real strategy from a guess.

29:50 – Fixing churn before it kills growth: Mark introduces the lead indicator of retention and how to diagnose why customers stop getting value, while Charles asks what founders should change the moment this episode ends.

36:37 – The innovator's dilemma, all over again: Mark explains how Siebel, PeopleSoft, and BMC lost their categories to Salesforce, Workday, and ServiceNow, while Charles compares the moment to a hockey team showing up to find the rink turned into a pool.

59:41 – What people get wrong about funding: Mark explains why venture capital is the wrong move for most founders, and why more wealth gets created outside VC backed companies than inside them, while Charles closes the conversation on why the proceeds from Mark's book go straight to mental health.

In this eye opening episode, Charles sits down with Garrett Gunderson, entrepreneur, bestselling author, and financial educator to challenge the conventional wisdom surrounding money, taxes, and wealth creation. Growing up in a coal mining town and learning painful lessons from his first bad investment at just 18, Garrett spent the next two decades uncovering why so many of the beliefs people hold about money are fundamentally flawed. What he discovered changed not only his own financial future, but the way thousands of entrepreneurs approach wealth.

From debunking common myths about investing and retirement to exposing the hidden opportunities buried inside the tax code, Garrett shares why financial success isn't about working harder, it's about thinking differently. He explains how entrepreneurs can build the right financial team, maximize deductions, and create strategies that preserve wealth instead of simply deferring taxes. Along the way, he reveals why most traditional financial advice is reactive rather than proactive, and why understanding the rules of money is one of the greatest competitive advantages an entrepreneur can possess.

Together, they dive into the mindset of true wealth-building, why cash flow matters more than accumulation, why financial freedom starts with education, and how aligning money with purpose creates lasting abundance. This isn't just a conversation about taxes or investments. It's a blueprint for breaking free from outdated financial beliefs and building wealth that serves your life, your business, and your legacy.

KEY TAKEAWAYS:

• How Garrett Gunderson turned early financial mistakes into a lifelong mission to challenge conventional wisdom about money
• Why many traditional beliefs about investing, retirement, and taxes are keeping entrepreneurs from building real wealth
• The difference between accumulating assets and creating true financial freedom through cash flow
• How understanding the tax code can become one of an entrepreneur's greatest competitive advantages
• Why proactive financial planning beats reactive money management

KEY POINTS:

01:08 – Growing up with the wrong money lessons: Garrett reflects on his upbringing in a coal mining town and the painful lessons from his first investment, while Charles explores how early beliefs often shape our financial destiny. 05:14 – Why conventional financial advice falls short: Garrett explains why much of what people are taught about money is outdated, while Charles highlights the importance of questioning accepted wisdom. 09:38 – Cash flow versus accumulation: Garrett challenges the obsession with net worth and retirement accounts, while Charles reframes wealth as freedom, not just numbers on a statement. 14:27 – Understanding the hidden opportunities in the tax code: Garrett shares how entrepreneurs can legally keep more of what they earn, while Charles emphasizes that financial literacy creates leverage. 19:11 – Building the right financial team: Garrett explains why advisors should serve as strategic partners rather than product salespeople, while Charles reflects on the power of surrounding yourself with experts. 24:43 – Proactive versus reactive wealth strategies: Garrett reveals why waiting until tax season is too late, while Charles discusses how intentional planning compounds over time.

Garrett Gunderson grew up in a coal mining town, made his first bad investment at 18, and spent the next two decades figuring out why almost everything people believe about money is wrong. Now he's written the books, built the business, and works with the entrepreneurs and high earners who are tired of being told to just wait it out.

Charles and Garrett get into the real problems with how most people handle money, from the three myths that keep even hard workers broke, to why the wealthy spend their time managing risk instead of chasing it, to the tax moves that the average business owner never hears about until it's too late. Garrett breaks down why cash flow beats the long game, how relationships and ideas build more wealth than capital, and why the financial industry is designed to work for itself first.

They also go deeper on what it actually looks like to build a life you don't have to escape from, why waiting until retirement to enjoy your money is a losing trade, and how the right environment, the right people, and a few unconventional reads can change the way you think about all of it.

This is not a lecture on saving more. It is a straight conversation about why the rules most people follow are keeping them stuck.

KEY TAKEAWAYS:

• Why hard work with the wrong philosophy still leads to broke, and what needs to change before the work pays off
• How the three biggest money myths were built to benefit institutions, not the people following them
• Why the wealthy focus on mitigating risk while everyone else is told to take more of it
• How cash flow and enterprise value beat the long-haul savings model for anyone who wants financial independence before old age
• Why the average business owner overpays taxes by $11,000 per quarter million in revenue, and what to do about it

KEY POINTS:

03:53 The first bad investment: Garrett walks through the decision that cost him money at 18 and turned him into someone who questions everything, while Charles connects it to the moment most people stop trusting their own instincts with money.

05:40 The three myths: Garrett breaks down why it takes money to make money, high risk equals high return, and playing the long haul are the three ideas that do the most damage, while Charles pushes him on where he first saw these fail in real life.

26:44 Risk is not what it looks like: Garrett explains what the wealthiest people actually do with risk and why taking action gets mistaken for recklessness, while Charles ties it to the entrepreneurs he has watched blow up and the ones who did not.

39:25 The tax moves most people skip: Garrett walks through the checklist he uses with business owners to find the $11,000 per quarter million in taxes they are overpaying, while Charles digs into which ones apply the moment someone starts making real money.

53:22 The books and the habits: Garrett names the reads that shaped how he thinks about money, relationships, and health, while Charles shares the unconventional places he picked up his own best lessons.

Jeff Byers turned a $1.8 million Department of Defense contract into a sports nutrition brand trusted by every NFL team, nearly every pro and college sports program in the country, and a long list of operators inside the world's most performance-driven environments, all while disrupting a $200 billion supplement industry where the average competitor is winning on hype and losing on quality. Now he is opening up the playbook on exactly how he did it.

Charles and Jeff dig into the real mechanics of building a category-leading brand in a category where customers have learned to assume the worst, from the leadership rhythms that keep a fast-moving team aligned, to the three-strikes feedback system that turned company culture into a self-policing engine, to the supply chain standards that have cost Momentous seven figures in lost sales and bought them a reputation no competitor can match. Jeff lays out the three supplements that should anchor any stack, the brand-building flywheel that turned college sports dietitians into long-term distribution, and the specific habits that wreck more entrepreneurs' sleep than anything else.

Together, they unpack why the cost of standing for something is far lower than the cost of pretending, why authoritative voices outperform paid social by a wide margin when you are playing a long game, and why the hardest people decisions get easier the moment you stop confusing kindness with avoidance.

This is not a sales pitch for supplements. It is a field-tested breakdown of how to build a brand customers cannot afford to doubt.

KEY TAKEAWAYS:

• Why the leader who shows up the same way after a loss as after a win is the only kind of leader anyone follows for long
• How a three-strikes feedback system strips ambiguity out of people decisions and lets a culture self-police without micromanagement from the top
• The single supply chain habit that separates a brand customers trust from one they tolerate, and why every batch matters more than every marketing campaign
• Why protein, creatine, and omega-3s are the only foundational stack that holds up under actual research, and why most everything else on the shelf is condition-specific at best
• How to take the high road with people you have to let go, and why your reputation in those moments compounds harder than any deal you will ever close

KEY POINTS:

03:53 The Pete Carroll lesson on leadership: Jeff describes the trait that separates teams that win championships from teams that fall apart, while Charles ties it to the founders who lose their best people without ever knowing why. 05:40 The ball always gets snapped: Jeff lays out the mental model from the NFL trenches that maps directly onto how startups either move or die, while Charles pushes him on what that looks like the moment a decision starts going sideways. 11:34 Three strikes, no surprises: Jeff walks through the feedback system that forces real conversations instead of vague one-on-ones, while Charles connects it to the moment every founder realizes avoiding the conversation is the more expensive choice. 26:44 The Momentous three: Jeff names the only three supplements that have enough clinical research to justify daily use for almost everyone, while Charles digs into why the rest of the shelf is mostly noise. 35:22 The seven-figure standard: Jeff explains why Momentous walked away from $700,000 in lost sales in a single quarter rather than ship one questionable production run, while Charles unpacks what that level of discipline actually does to a brand long term. 39:25 The flywheel of trust: Jeff breaks down how Huberman, Tim Ferriss, Rich Roll, and eventually Arnold Schwarzenegger ended up behind the brand without a single influencer deal, while Charles challenges him on whether that playbook still works for a founder starting from zero.

Cem Atik built a portfolio that generated over two billion dollars in revenue without founding a single company from scratch, scaled a SaaS business from barely seven figures to forty-five million in twelve months, and now runs one of Europe's most active acquisition and growth operations buying distressed e-commerce and SaaS businesses and turning them exit-ready. Now he is pulling back the curtain on exactly how it works.

Charles and Cem get into the real mechanics of acquiring and scaling businesses that other operators have given up on, from identifying the unit economics that separate a hidden gem from a money pit, to building a lead generation engine that converts without burning through ad spend, to running A/B tests that take a company from stagnant to scaling inside a year. Cem breaks down the organic content strategy that consistently delivers higher ROI than paid channels, the onboarding tweak that boosts conversions by up to forty percent, and what he would do in the first ninety days if he were starting a SaaS company from zero today.

Together, they explore why selling the result always outperforms selling the product, why the highest return on investment platform is one most operators are already ignoring, and why knowing your unit economics matters more than any marketing tactic you will ever run.

This is not a masterclass in theory. It is a field-tested breakdown of how overlooked businesses become acquisition-ready machines.

KEY TAKEAWAYS:

• Why unit economics are the single most important number in any business and how most founders are measuring them wrong without knowing it
• How Cem's offer-testing framework identifies the highest-converting angle without committing your full budget to a single bet
• The landing page principle that will cost you more than your entire ad spend if you skip it before scaling traffic
• Why targeting an audience with purchasing power changes the complete math of your business model regardless of what you are selling
• How to use AI as a sparring partner rather than a search engine and why that shift produces decisions you can actually trust

KEY POINTS

01:21 Two billion in revenue: Cem reveals the scale of what his team has built for businesses they did not start, while Charles breaks down why the number changes everything about how you think about acquiring versus building.

02:06 Finding deals no one else sees: Cem explains the M&A network strategy and why paying consultants above market rate ensures the best opportunities land with him first, while Charles connects it to how he ran the same play in real estate.

04:30 The unit economics test: Cem walks through the exact numbers he looks at before touching a business, while Charles pushes him on what it really looks like when a company thinks it is healthy but is not.

07:27 Sell the result, not the product: Cem uses a telehealth case study to show why reframing your offer around the outcome rewires the entire conversion process, while Charles ties it back to how every great brand in history has done the same thing.

12:20 The A/B tests that actually work: Cem shares the specific experiments that consistently outperform across industries, while Charles digs into where founders should be running those tests if they want the fastest feedback loop.

14:52 Where the real ROI lives: Cem breaks down why LinkedIn and Reddit outperform paid channels for most operators and what organic content actually needs to say to move an audience, while Charles challenges him on how you cut through when everyone else is doing the same thing.

Victor Damasio built one of Brazil's longest-running masterminds, grew an audience of 700,000 on Instagram, and helped hundreds of professionals turn their expertise into high-ticket income, all without recording a single polished course. Now he is bringing that playbook to the United States for the first time.

Charles and Victor get into the real mechanics of monetizing what you already know, from landing your first paying mentee without a following, to charging what your time is actually worth, to running a group program that people renew year after year. Victor breaks down the four-question framework that flips the sales dynamic entirely, putting clients in the position of pitching themselves to you rather than the other way around, and shares what he would do in the first 90 days if he were starting from scratch today.

Together, they explore why you do not need to be the best in your field to teach, why your next client is probably already in your phone contacts, and why selling before you have a perfect program is not a shortcut but the actual method.

This is not a masterclass in theory. It is a step-by-step look at how ordinary expertise becomes extraordinary income.

KEY TAKEAWAYS:

• Why you do not need to be number one in your field to mentor others and start generating income from your knowledge
• How Victor's four-question application framework gets prospects to sell themselves into your program before you ever pitch them
• The mindset shift that moves you from free advice to a paid mentorship offer with people who already know and trust you
• Why launching a messy first cohort beats waiting until your program is perfect every single time
• How to build a mastermind where clients stay for over a decade by leading with care over credentials

KEY POINTS:

01:13 Turning passion into profit: Victor explains why you only need to be a few steps ahead of the people you want to help, while Charles connects it to what most people get wrong about expertise.

03:10 Selling before you are ready: Victor reveals why starting with a blank iPad was intentional, while Charles digs into what separates people who launch from people who keep preparing.

06:26 Finding your first mentees: Victor shares why your next client is already in your contacts, while Charles pushes him on how to move from a friendly relationship to a paid one.

08:08 Charging for what you know: Victor walks through the moment people stop doing free coffees and start getting paid for them, while Charles connects it to how his own team handles the same dynamic.

12:11 The four questions that close clients: Victor breaks down the reverse polarity framework that makes prospects pitch themselves to you, while Charles unpacks why hiding the price always costs you more time than it saves.

40:04 Keeping clients for 12 years: Victor shares what actually drives long-term retention, while Charles challenges him on what it really takes to build that kind of loyalty.

As a co-founder of Hims and Hers, Joe helped take a direct-to-consumer healthcare brand public at a $1.6 billion valuation. Now as CEO of Dutch, he is reshaping how pet owners access veterinary care through telemedicine. Joe has spent 15 years learning what it actually takes to build something that lasts, and in this episode, he holds nothing back.

Charles and Joe dig into the real mechanics of building a venture-backed business, from knowing when to burn everything down and start over, to hiring the right kind of crazy, to leading a team through failure without losing them. Joe breaks down the pivot that took Hims from a product nobody wanted to a $200 million valuation in a single month, and what he would do completely differently if he had to do it all again.

Together, they get into why execution beats ideas every time, why dreaming too small is just as dangerous as dreaming too big, and why the best businesses are built on a simple formula: faster, cheaper, better.

This is not a highlight reel. It is a masterclass in what entrepreneurship actually looks like from the inside.

KEY TAKEAWAYS:

• Why execution and perseverance matter more than the original idea when building a scalable business
• How Joe took Hims from a failing product to a $200 million valuation in just one month after a full rebrand
• The hiring mindset that separates startup survivors from people who need stability
• Why dreaming too small is one of the most underrated mistakes founders make
• How faster, cheaper, and better remains the most reliable formula for building something people actually want

KEY POINTS:

• 01:12 : Building venture-backed businesses: Joe breaks down what VCs actually look for, while Charles connects it to the grind most entrepreneurs overlook.
• 03:49 : The power of the pivot: Joe walks through the moment Hims almost died and what it took to start over, while Charles explores why most founders wait too long to make that call.
• 06:21 : Leading a team through uncertainty: Joe shares what it feels like to jump off a cliff and hope for the best, while Charles digs into how you bring your people with you.
• 08:49 : Hiring for startups: Joe explains how to spot someone built for the chaos of early stage companies, while Charles challenges the conventional wisdom around who makes a great hire.
• 48:06 : Lessons from a billion dollar exit: Joe reflects on ringing the NYSE bell and what he wishes he had known sooner, while Charles pushes him on what would have made it faster.
• 51:58 : Dreaming bigger: Joe makes the case for setting goals that feel impossible, while Charles ties it back to building a business that is genuinely in service to others.

Most people think cybersecurity is complicated. MK Palmore disagrees. With 32 years in the federal government, two decades as an FBI special agent, and executive roles at both Google Cloud and Palo Alto Networks, MK has seen every angle of the threat landscape, and his message is simple: the basics will save you.

Charles and MK go deep on what everyday consumers and small business owners are getting dangerously wrong about their digital security, why a data breach can be the last thing a company ever survives, and how the adversary is quite literally banking on your laziness. MK also gets candid about the tools he personally trusts, the privacy myths that need to die, and why doing a few simple things consistently beats any fancy security stack money can buy.

Whether you're a solo entrepreneur or running a growing team, this episode is a wake-up call you didn't know you needed, and a practical roadmap to making yourself a much harder target.

KEY TAKEAWAYS:

• Why multi-factor authentication is still the most underused line of defense for consumers and businesses alike
• How a single data breach can financially and reputationally destroy a small business overnight
• The truth about privacy tools, what's worth your time, and what's just noise
• Why consistency, not complexity, is the real foundation of digital security
• The devices and platforms a former FBI cyber executive actually uses to protect his own data

KEY POINTS:

• 01:20 – The basics most people ignore: MK breaks down the simple steps that make the biggest difference, while Charles connects them to everyday consumer behavior.
• 07:45 – Inside a data breach: MK walks through how attacks unfold and why SMBs are prime targets, while Charles unpacks the real financial and human cost.
• 15:30 – The SMB blind spot: MK explains why small businesses underestimate their exposure, while Charles shares why the assumption of being "too small to target" is one of the most dangerous myths in business.
• 28:10 – Building a security culture: MK lays out what it takes to get a team bought in on cybersecurity, while Charles explores the leadership gap that leaves most companies vulnerable.
• 45:00 – Privacy tools, myths, and what's actually worth it: MK cuts through the noise on VPNs, incognito mode, and Faraday bags, while Charles weighs in on his own approach to personal data protection.
• 56:55 – The everyday carry of a cyber expert: MK reveals the exact devices and platforms he relies on, while Charles reconsiders his loyalty to Microsoft.

In this thought, provoking episode, Charles sits down with Nir Eyal, author, behavioral design expert, and investor, to explore the psychology behind why people become attached to certain products, ideas, and habits. Nir unpacks the core principles from his bestselling book Hooked: How to Build Habit, Forming Products, revealing the behavioral frameworks that the world's most successful companies use to create products people return to again and again.

From the science of triggers and rewards to the ethical responsibility of building technology that shapes human behavior, Nir explains how entrepreneurs and product creators can design experiences that truly resonate with users. He also dives into the difference between manipulation and meaningful engagement, sharing why understanding human psychology is essential for building products that serve people rather than exploit them.

Together, they explore how habits are formed, how attention has become the most valuable currency in the modern economy, and why the future of innovation lies at the intersection of psychology, technology, and intentional design.

This isn't just a conversation about product development. It's a blueprint for understanding human behavior, and for building companies, tools, and ideas that people genuinely want to make part of their daily lives.

KEY TAKEAWAYS: -How Nir Eyal developed the behavioral design framework behind Hooked: How to Build Habit-Forming Products -Why the most successful companies design products around psychology, not just technology -The four-step "Hook Model" that explains why users repeatedly return to certain products and platforms -The difference between ethical engagement and manipulation when building habit-forming technology

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

KEY POINTS: 01:10 – The psychology behind habit-forming products: Nir introduces the behavioral science that inspired his work, while Charles explores why understanding human behavior is essential for modern entrepreneurs. 04:35 – The Hook Model explained: Nir breaks down the four-step framework behind habit, forming products, while Charles reflects on how the world's most successful platforms keep users coming back. 08:12 – Internal triggers and human behavior: Nir explains how emotions like boredom, curiosity, and uncertainty drive digital habits, while Charles highlights how these triggers influence everyday decisions. 12:40 – Engagement vs. manipulation: Nir discusses the ethical responsibility of product creators, while Charles explores the line between building value and exploiting attention. 17:05 – Why distraction is an internal problem: Nir challenges the idea that technology alone causes distraction, while Charles reflects on how self-awareness plays a role in productivity. 22:18 – Designing products people love: Nir shares how companies create experiences that naturally integrate into daily routines, while Charles emphasizes the importance of solving real user problems. 27:44 – Behavioral design as a business advantage: Nir explains why understanding psychology gives entrepreneurs a massive edge, while Charles ties it to building products that last. 32:10 – The future of technology and human attention: Nir closes by discussing the evolving relationship between technology and human behavior, while Charles reflects on the responsibility innovators carry when shaping habits.