Proven Podcast

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.