Founder Self Talk (full audiobook) | Charles Cormier

Founder Self-Talk by Charles Cormier. This is Charles, the AI version of me, reading my book so you don't have to wait for me to find the time. Notes and plays on go-to-market, fundraising, systems, pain, and money. Let's go. A note before you start. I've been in lead gen since 2017. I started out doing lists and prospecting for realtors. COVID killed that business in a single week, and I had to pivot hard and fast. Since then, I've built Top Leads, GTM Ventures, Raz Rocket, and Podpire. And I've hosted thousands of founders, CEOs, and investors on my podcast. At my peak, I was doing 15 interviews a day. Over those years, I wrote a lot— thousands of LinkedIn posts and hundreds of newsletters. Most of it was written fast between calls, after a long run, or at 6 AM in Oaxaca. Some of it was smart, and some of it was me thinking out loud. This book is the best of it. I cut it, edited it, and put it in order. I didn't write it like a textbook, and you don't have to read it front to back. Open it anywhere. Each part has two kinds of pages: notes, short lines, the stuff I'd text a founder friend at midnight; plays, longer pieces with the actual system, the numbers, and how I run it. It's for founders, the people who stay in the game for 10 years when a normal person wouldn't last 30 days. If something in here makes you money, tell me. If something in here is wrong, tell me louder. Charles, I don't want to get lucky. I want to build a solid base and grow ground up through day-by-day habit building. Part 1: Go-to-market. Notes. Note: Cash in the bank beats vanity points on the scoreboard. Most founders go for ego, not cash. Forbes features, vanity podcasts, make-believe PR. It looks good on LinkedIn, but it doesn't build a pipeline. The real game is sending cold emails, getting hard nos, and grinding through rejection until you get enough yeses to hit product-market fit. Then you stack those yeses into cash. You don't have a cold email problem. You have a GTM problem. Personalization doesn't equal conversion. Loved your podcast from 2021 where you mentioned your dog Rocco followed by a generic offer is just lipstick on a cold email. A great offer is an instant pattern match. No icebreaker needed. Pain, then solution, then reply. The biggest bottleneck in B2B outbound isn't sending. It's what you're asking for. Hype is not conversion. Hype gets you leads, maybe. Conversion comes from clarity plus ICP alignment. If I need to stop and think to understand your offer, most people will just walk by. Cold email doesn't kill your brand, it exposes it. Most people can't handle that level of honesty from the market. Cold email is a stress test. It doesn't destroy strong systems, it reveals weak ones. Amateurs send from their main domain, get blacklisted, then blame outbound. They damage themselves by not understanding infrastructure. Being repelled by cold outreach is a net loss, just like being turned off by ads. That's your ego in the way. Tell it to move a bit. It's blocking the sun. Deep thinkers skip the apologies. Drop the I hate to bother you and the I'm sure you get this a lot. Go in with a precise intention and take one slice. Your prospect will tell you when it's time for the meeting link. Sending it too early makes you sound like a shark. If the only reply you get is, what's the cost? You can already discard it. Serious buyers want copy samples, ICP fit, proof. Nobody makes a decision off one cold email and a price tag. Most people talk about meetings before they talk about interest. They skip 5 steps and then complain they have no meetings. Serious offer, funny email. That's been my most consistent combo for opens and replies. Most outbound sounds like a CRM sneezed. The wallets aren't in the future, they're in the present. The money is in fixing last decade's problem for today's decision-makers. You're pitching autonomous agents to people who still struggle with email segmentation. Meet buyers where they actually are, not where you wish they were. The number one mistake isn't pricing, it's client selection. If you sell to high-level operators, you don't need manipulation tactics. Once your business reaches a certain level, avoid high-resistance prospects. Resistance means the person thinks you're a salesperson and you're actually a doctor. A healthy dose of resistance is fine, say 5 to 20%. When a meeting goes way over that and you can feel it, part ways politely. Disqualifying is as important as qualifying, especially when your time is the finite resource. Get to a no fast is great advice once you have 10 to 30 meetings a month. Before that, it's just ego, and ego doesn't equal revenue. Success is a staircase, not a jump. The only people winning from extremist advice are the ones selling it. Most software companies should run an agency arm until they find product-market fit. Clients confirm their pain by paying you with their hard-earned money. Reverse the filter on your clients. A great lead gen system will absolutely generate leads. If the client has product-market fit. More pitches means more money. It also means more resistance. Haters don't pay bills, clients do. You need an A, B, C, D, E, F, G plan. One channel as the cause of all your success is a feeding tube that can be unplugged at any moment. I force serendipity to happen constantly. The moguls on this planet don't wait for things to come to them. They reach out relentlessly. Reaching out kills the ego, just like stand-up comedy does. Play the 5x5x5 email matrix. If you can't get meetings with this system, you're in the wrong place at the wrong time. Write down your ICPs. Start with 5. Example: fintech CEOs with $5M in funding, 7 people on the sales team, Using HubSpot, headcount growing. For each ICP, write 5 pain points. Cost, hiring agencies, staff turnover, broken internal comms, broken systems. For each pain point, write 5 solutions. Lower cost, an integrated agency, an agency that stays, a shared Slack channel, a Zapier setup. 5 ICPs times 5 pains times 5 solutions equals 125 emails. That's five pain campaigns per ICP, each with five emails, one solution per email. Twenty-five emails per ICP. Send it, and the market tells you which ICP, which pain, and which solution are real. That's what I call the product market fit machine. It pays the bills while it gives you market data in real time. Play the math of a simple outbound engine. When I first packaged my system, the stack cost me about $135 a month. 10,000 emails a month, 3% positive reply rate equals 300 leads a month in your calendar. Of course, it can be less. Of course, it takes iteration. But outbound is infrastructure plus iteration. Domains warmed and rotated, lists built from multiple sources, 3 to 5 angles tested in parallel, Follow-ups across months. That isn't a free lottery ticket. It's a system. That's also why I don't do commission-only deals with founders who don't have cash in the bank. Commission only is usually a signal of no cash flow and no skin in the game. Play: Why some emails get replies. I once had a campaign getting 2 to 5 positive replies a day on autopilot. Here's why it worked. People were very interested in AI outreach but didn't know where to start. Most weren't ready to buy, but they were ready to learn. My job at that stage was to educate. The email was lightly personalized. It was informal, short, and simple. It wasn't formatted like a cold email, so people didn't read it as one. No links in the email, so it stayed away from spam filters. It mentioned YouTube, which people trust. The call to action was tiny. Can I share it here? The signature was light. My thesis: people are all in for free stuff. You have to fight for free, meaning that even if the top of your funnel is free, you still have to earn the attention. And here are some of my best angles from a strong year of campaigns. No better city than my city. Drop their city name in the subject. Successful people consciously choose where they live. They love their city. No better days than uni days. Homo sapiens are really homophilians. People still remember their uni days. The reply rate showed it. Niche niches, femtech and female CEO campaigns. Hyper-specific beats broad every time. The podcast invite. Hey, first name, would love to have you on the CEO Wisdom Podcast to talk about company and vertical. Mind if I send you more info? More on this one in part 2. Play. Map the whole funnel. The leap from someone interested to someone booking a call is massive, and it's getting wider as attention spans shrink and trust drops. Map every step. Map cold reply, then soft interest. Soft interest, then content consumed. Content consumed, then value received. Value received, then meeting booked. Meeting, then closed deal. If you don't give before you ask, you get ghosted. If you don't optimize each step, your income will be capped forever. Stop manifesting. Stop crying no meetings. Engineer the actual conversion path. Play money days. About two or three years into entrepreneurship, I was traveling the world with my wife, and cash flow was sometimes tight because I had a big team. So I scheduled money days—a full day in Google Calendar devoted to one thing. Generating cash, selling, going after leads. Back then, I cold-called a lot. And it worked. Cash flow always came at some point. Energy flows where focus goes. When you're starting out, get your ass to work on what's important, which is sales. A lot of founders cruise along depending on one big client or referral partner. When the storm comes and they get cut off, they panic. Business is mostly cash. Stray from that and you're in danger. Part 2: The podcast is the funnel. Notes. Notes. Stop thinking you're the next Joe Rogan and that you'll make a fortune from podcast ads. Put lead gen in the podcast equation. If you cold DM someone, their guard is up. If you invite them onto a podcast, their guard drops immediately. Interviewing your ideal clients as podcast guests is one of the highest ROI moves in business. You get 45 minutes with your exact ICP. They show up prepared, in a good mood, and they talk openly about their problems. On a podcast, you learn their language, their objections, and how they make decisions, and you build rapport in the best possible context. I don't go to networking events. My podcast does that work for me. Charging guests to appear doesn't scale. Use the podcast as the first step toward your paid offer. My sequence: podcast, then mastermind, then paid offer, then client becomes an affiliate. Immediate money gluttony caps you at 6 or 7 figures. Patient podcasting goes for Everest revenue. Most people treat the end of the interview as the end of the relationship. It should be the beginning. If you want someone to trust you, spend time with them. A podcast lets you spend hours with your market every month. Sponsors don't care about you. They care about your audience. The podcast funnel checks every box of human psychology. It reverse sells like no other tool out there. In a world clouded by direct sales, lead gen podcasting stands out and sells out. Every guest is a potential client, partner, investor, or friend. The trap with podcasts is impatience. People think it's hard. They struggle to find the right guests, and they don't stay in touch with the ones they had. Play: What thousands of interviews actually did for me. When people asked why I was interviewing 15 CEOs a day, here's what I told them. Podcasts have been life-changing for me. 50% of my customers came from there. 25% of my deep business insights came from there. I made lifelong friends who support my journey. I got paid to do it through sponsors and AdSense. I haven't found any other use of my time with a higher long-term ROI. At one point, I ran the numbers on my first 2,000 or so episodes, around 30 clients, and about 10 of them became close friends and business partners. That's the part people don't price in. A client is worth a few thousand a month. A friend who is a founder is worth a lot more over 10 years. It also replaced my reading. I've read more than 1,500 books on Kindle, Audible, and Scribd. Then I stopped, because interviewing 15 CEOs a day and asking them the exact questions that serve my business is way better. It's like getting $30,000 of consulting a day. Free billionaires answered my money questions. A guy with five IPOs answered my mandate questions. People sent me AI apps that replaced parts of my team. Play the invite that built the network. My template was this simple: Hey, first name! Would love to have you on the CEO Wisdom Podcast to talk about company and vertical. Mind if I send you more info? No link, no pitch. One question. That one approach got me in front of billionaires, top scientists, and future co-founders. People who are not on the monetized podcast trend are missing out. Play the podcast funnel step by step. One, pick guests like you pick clients. Most founders invite people based on name recognition, not client potential, and they waste months interviewing people who will never buy. Target your I. Founders, CEOs, high-ticket buyers. Use cold email to filter on revenue, funding, and niche. 2. Run a great interview. The goal is to make your guests shine. Prep custom questions. Know their niche so they trust you immediately. Keep it organic. Study Joe Rogan for rapport that feels real and Diary of a CEO for story. Follow up for a year, not a day. This is where the money is. See the follow-up play below. 4. Repurpose everything. One episode becomes YouTube, Shorts, LinkedIn posts, newsletter ideas. Shorts are the gateway to long form. 5. Turn trust into partnerships. Some guests become clients, some refer clients, some come into your mastermind, some become co-founders. Treat your podcast like a sales pipeline, not a side hustle. Play the follow-up system. Most people drop the ball after the first interaction, assuming if they're interested, they'll follow up. Wrong. After every podcast and every call, right away, follow me, I'll follow back. Any founders you'd refer to the show? Do you have a newsletter I can follow? 1 to 30 days later, a free strategy or insight tied to their business, case studies and testimonials. An invite to something with peers, like my CEO Meditation Club. 30 to 120+ days later. A free list or resource that's useful right now. How's business? An ROI calculator that triggers action. I once went on a full Calendly follow-up rage— texts and emails days, hours, and minutes before each call to kill no-shows, then a long value email after every call. Lists, my best campaigns, my newsletter, my masterminds, a referral offer. Long, because once I know you, going long is the goal. Most people send one follow-up and give up. I send many over months and close deals other people would have lost. The game isn't just about generating leads. It's about staying in the game long enough to win. Why the podcast beats the billboard. The best example of all this happened in 2026. OpenAI bought TBPn, a daily live tech show started by 2 founders, for a reported 9 figures. It was one of the most remarkable bootstrapped exits in media history. You don't need to sell your show to OpenAI. The lesson is that attention plus trust plus a specific audience is an asset. A podcast built around your buyers builds that asset every week while it fills your calendar. Part three: Selling and closing. Notes, note. Have a great product? Then sell the heck out of it. Jordan Belfort skipped the first step. Plenty of founders skip the second. I've had miserable startup failures with the best product and zero sales. Sell me this pen is the lowest IQ sales challenge there is. Sales has one job: to help someone decide on something that could be valuable to them. You're not there to convince the world your product works. You're there to talk to an educated person and guide them like a consultant. I can't sell someone a dream I don't believe in. It has cost me business, but only the wrong kind. Avoid the clients who expect magic without effort, want shortcuts but reject real systems, and drain energy, demand handholding, then disappear. Cash flow is king. Random holiday promos don't scale. They cheapen what you do. Swap discounts for partnerships. You promote me, I promote you. You refer a friend, you get a credit. If I can't personally use your product, I don't want to sell it. Exchange services so you understand the thing you're helping grow. For founders I really believe in, I'd rather take commission or equity than a bigger fee. It aligns us on the moonshot instead of the short-term cash grab. People who are in the game to win buy differently from people in it for the lifestyle. If your goals are mostly money-focused, sell to the ones in it for the big win. I respond to almost every pitch that makes me even slightly curious. It shows me whether the tool fits, what their pitch does better than mine, whether they follow up, and it lets me practice being the buyer. When an angry message comes in, first write the reply your ego wants to send. Then remove everything negative. Then send what's left. Most people fall in love with what they sell. Fall in love with who you sell to. Play pick your V. I C P. I started out working with realtors. Most were making dollar one hundred k a year, some dollar three hundred k. Almost all of them looked unfulfilled, working for demanding homeowners who negotiated their commissions down and threatened to go to a competitor, and they mirrored the same behavior onto me. So why would I keep working with them? About 5 years in, I made a big pivot. I'd only work with my very ideal customer persona: serial tech entrepreneurs with deep pockets and a high tolerance for risk, growth-minded, experimental in business and in life. Since then, I work with people I want to be like. They pay me, and they feed my fire while I feed theirs. Your ICP is not just demographics. Industry, age, and location are table stakes. The real filter is psychographics— how they think, how they decide, how they behave when things go wrong. I am my own ICP. I build for people wired like me. Play the price hike. I once raised prices and it cost me about 5% of my usual close rate. I didn't worry about it because the floor kept going up. Then one day a client negotiated me down to 2 weeks of work instead of my 1-month minimum. Normally I don't feel good doing anything under 3 months. But I asked one question, how soon are you able to start? Went with my gut and accepted. I launched the campaigns fast. The work took a few hours, and I effectively banked $1,500 an hour. I put it straight into ads. The lesson isn't be cheap or be expensive. It's have a floor, know your numbers, and be flexible when speed is the asset. Play young founders, fast results. At one point, I stopped taking on older execs who came with baggage. Younger founders had no false preconceptions slowing them down, no ego resistance to new systems, and no identity crisis when change was needed. They just executed, and they got results faster. This isn't about age. It's about coachability. Look for people who got promoted in their last job, then promoted again. Being promoted many times shows someone is coachable, adaptable, and a strong communicator. Hire and sell to those people. Play, contracts, and trust. For small engagements, I don't obsess over contracts. If someone wants to cheat me up front, I haven't lost much, and they've given up a relationship that could have been worth millions. When it's many hours of my time and 6 figures on the line, I send a simple contract. Controlling your ICP is how you eliminate drama. The right clients don't need a 40-page agreement to behave well. Part four: Raising money. Notes, note. Fundraising isn't pure merit, pure storytelling, or pure traction. It's a messy mix of psychology, timing, positioning, and process. Most founders treat fundraising like a side quest. Let me build the product, then I'll go raise. Then it becomes a second full-time job with no rules. VCs don't fund relationships; they fund momentum, clarity, and outcomes. Fundraising is a sales process. Lead gen, qualification, follow-ups, closing, urgency, scarcity, narrative control. Treat it like a pipeline, not a coffee chat tour. Investors don't want information. They want inevitability. Don't say, here's what we're building. Say, this market is shifting, and we're the only rational outcome. Your job isn't to convince. It's to make the alternative feel illogical. Almost nobody cold emails VCs correctly. Hi, do you have 15 minutes? With a deck attached is noise. Outbound to investors works when it's precise positioning, targeting, investor fit. Intros are overrated and meetings are cheap. The hard part is the closing infrastructure. The fundraising market has a temperature. Hot windows open and hot windows close. If your process takes 4 months to start, The market may already be gone. Momentum is a weapon. Interest and conviction are different things. Most investors will stay interested forever. Very few will move first. Investors don't lead because of a perfect deck. They lead because they're afraid of missing something that's already moving. The founders who close fastest aren't the best storytellers. They manufacture the conditions where waiting feels like a mistake. Maximum leverage is when capital chases you. When a company turns down a preemptive round because it doesn't need it, that's what leverage looks like. Most founders have the opposite problem. A hundred nos is not a verdict. Plenty of founders were rejected by every fund in the room and built the company anyway. Play the fundraising machine. Investor demand, then narrative, then pipeline, then process, then Demand. Build a list of funds and angels that actually invest in your stage, your sector, and your check size. Not VCs, your VCs. Narrative. One paragraph that frames the shift in the market and why you're the obvious winner. Test it in emails before you put it in a deck. Pipeline. Run outbound to investors like you'd run outbound to customers. Multiple angles, real follow-ups tracked in a CRM. 4, process. Control the timeline, batch the meetings, set dates, handle objections the same day. 5, close. Create competitive pressure, honestly follow up relentlessly and close clean. With RAS Rocket, we've run this for founders as a sprint. One client got to $18M in term sheets in under 4 weeks. That doesn't happen by begging for intros. It happens because the process is engineered. Solving the Lead Investor Problem. Here's how most seed rounds die. A founder spends 3 months taking meetings. Investors say, we love the space and keep us posted. Some say, we'd love to participate. Nobody says, we'll lead. The founder waits, follows up, and gets polite non-answers. And a room full of interested investors slowly goes silent. That isn't a pitch problem. It's a momentum problem. The Commitment Cascade. Stop looking for a lead first. Go to 20 to 30 investors aligned with your thesis and ask one question: if a lead closes, are you in? Collect soft, conditional commitments. No pressure, no terms. Now go to lead candidates with this: I have this much ready to close behind you. You set the terms and you get the best deal. Your job is to lead a round that's already won. Not to take a lonely first bet. You've changed the whole conversation. The lead's risk drops dramatically and their upside stays intact. They aren't going first into the dark. They're leading a room that's already full. Play: Build the room. I like putting founders and investors in the same room, on camera, with structure. That's why we built Spark Tank. Startups pitch in a few minutes, VCs give fast in-or-out decisions live, and the whole thing streams on LinkedIn, X and YouTube. It isn't a demo day; it's structured signal. Every founder and every investor is vetted, and distribution is shared, so everybody wins. If you're raising, find or create rooms where investors watch each other react to you. Momentum is contagious. Part five: Systems, AI, and leverage. Notes note. LinkedIn influencers talk about systems, but what is a system? A system is something that keeps generating outcomes cash once it's set. A bot, an automation, an AI agent doing work while you're away. You don't rise to the moment, you fall back on your systems. Most people try to handle life, and that breaks fast. Design a life that handles itself. Being busy is a weak flex. If you're always busy, your systems are broken. Your business should run without you. If it needs you every day, it's a job. Most entrepreneurs are really entrapreneurs trapped in their own business. They forgot why they wanted to be entrepreneurs in the first place. Stop putting all the responsibility on yourself. That's an ego thing. Yes, your team will mess up. Yes, your name might get a stain or two. It's fine. It took me 6 years and OpenAI to understand that employees wouldn't scale the way I wanted. The most toxic thing about hiring the wrong people isn't the salary. It's the opportunity cost of coaching people who don't want to climb the tree. Founder mentality doesn't transfer by declaration. It's earned through ownership, risk, and consequences. Early on, I treated low-level hires like founders, with the same incentives and the same expectations. That mistake cost me years. Once I had predictable systems and repeatable lead flow, full commission reps started coming to me. The system de-risks execution. AI will go as far as your brain goes. If you're not sharp, the AI you're commanding won't be either. It's still about the best offer for the best ICP, and no AI can tell you that yet. Most people saying ChatGPT sucks don't realize they suck at prompting. Give me a sales strategy gets you something generic. Give me a 3-step cold email sequence for B2B SaaS CTOs at $10M plus a RR gets you gold. Give the model as much context as possible, evaluate its answers, and keep going in the same chat. It keeps getting better. Agencies that sell hours are squeezed to death. The next wave sells agents, not hours. Productize your brain. One human brain managing many AIs. If your business isn't built that way, restart the clock now. AI will compress execution, commoditize skills, and reward leverage. It won't replace obsession, long-term thinking, or pain tolerance. That's the new moat. Your emails have em dashes? Must be AI. Clients don't care how the words were written. They care if it lands, resonates, and converts. Stop being stubborn about your old thesis. Plenty of stubborn people died trying to prove a wrong thesis right. Play. My 3 best systems. The 3 systems that paid me the most while I slept. The podcast. Episodes keep getting watched without me doing much. Guests reshare them, Shorts get cut, search engines index them. Cold outreach. Emails go out to my ICP every single day and book meetings automatically. LinkedIn on autopilot. Content, outreach, and comments handled by AI, so I stay present without living in the app. Later, these grew into a mostly agentic outbound stack generating 20 to 30 positive replies a day. The principle didn't change: build it once, let it run, improve it every week. Play: SOPs without a chief of staff. One of my last attempts at the hire a human for this model was hiring a chief of staff to write SOPs. Thousands of dollars, a lot of my time, and a lot of frustration. Then one day, riding my motocross bike, it hit me: record all my calls, feed the transcripts to an AI, and let it write the S. O.P.S. That's the pattern now. Before you hire for a process, ask: Can I record it, document it with AI, and hand it to an agent? Play: The Dad Stack. Becoming a dad reinforced something I already believed: systems keep you alive, And systems let you thrive. People thought I was crazy. A kid, 5 dogs, a company. Good luck surviving that. Here's how it works. Dogs, then walk or run twice a day, non-negotiable. Family, then real support, nannies included. Energy over ego. Life, then buy leverage. Tech, help, anything that removes friction. Health, Then still locked in. Did things go wrong? Of course. Scares, emergencies, chaos moments. But we didn't collapse because we don't rely on hope. If plan A fails, plan B kicks in. If X happens, we already know why. Being an Ironman, being a founder, and being a dad run on the same principle. Play my office. I'm a productivity nut. Here's what's in my office. A pull-up bar. If I pass under it, I do a pull-up, and at least 10 a day. A treadmill under the standing desk. If you're going to stand, you might as well walk. It looks funny, it starts conversations, and it helps after leg day. A screen looping my vision board, the properties, the things I want to launch. Water and tea all day. A journal to scribble and visualize. Your environment is a system too. Design it so the right behavior is the default. Play 21 questions for your next planning session. What did I miss yesterday that actually matters today? What's the deeper structure underneath this problem? What assumptions am I making that might be wrong? What's the opposite of my assumption, and could it be true? If this idea failed, what would be the real reason? If it succeeded wildly, what made it work? What question should I have asked instead? Where is my biggest leverage bottleneck right now? If I 100x this plan, what breaks first? If I 0.1x this plan, what becomes trivial? If I had to solve this in 24 hours, how would I do it? With zero budget? With 10x the budget? What would the highest version of me optimize for right now? What would make this problem irrelevant a year from now? What's the one move today that creates the most leverage tomorrow? What breaks if this suddenly scales to 10,000 users? And to 100,000? Where am I still thinking like an operator instead of an architect? What's the simplest way to do this at a world-class level? What am I avoiding looking at because I know it's the real issue? Part six: The founder mind. Notes note. I've been in startups for ten years and watched founders drop like flies. Winners delay gratification, and not in a cute motivational way; in a brutal, irrational way. They stay in the game for 10 years when a normal person wouldn't last 30 days. That's the real filter. Not intelligence, not ideas, not timing. Can you keep going when there's no reward? Pick your foxhole carefully. You don't need more people. You need people who'll still be there in 10 years. Patience is the ultimate cheat code. But most people are patient in the wrong places. They quit a business after 3 months and stay in a dead-end job for 10 years. It took me 7 years to really improve my relationship, 10 years to build a business that prints cash, and 3 months, 3 broken doors, a wrecked bed, and 4 vet visits for a rescue dog to adapt to a new life. Some things take years and some take months. Impatience in the wrong place kills both. I take 200 times more shots than most people. I don't give an emotional damn about negative responses. Hate is just a data point on the experiment. Reputation is a temporary human construct. Results last. If you're not a bit quirky, you're probably not onto something. Every highly successful CEO I've met was openly odd. They don't reboot themselves to fit in. They adapt their environment to their quirks. The best CEOs are open books. They share everything because sharing gets feedback, and once it's out, it's old news, which forces them to go find something better. Intellectuals and independent thinkers make great CEOs. Everything relates to business in the end. Cross-pollinate from other fields and connect the dots. The best thing a loser can do is hate. Instead of hating from the sidelines, come play on the field. Copy, paste, improve. That requires leaving your ego in the stands. Even if a 20-year-old is doing YouTube better than you, Quality doesn't scale on its own. Quantity of reps is how you get quality. I've passed thousands of quality lane high performers by doing more reps and improving faster. Execution beats ideas. A bad plan executed beats a genius idea collecting dust. Perfectionism is procrastination dressed up as discipline. High performers keep their perfectionist on a tight leash. Low performers let their perfectionist leech on them. Your inner coach is everything. Mine is calm, fatherly, and honest. It boosts me in the low moments and reinforces patterns in the high ones. The last thing it does is throw a pity party. Let the visionary set the impossible goal. Let the planner handle the small final details. If you set hard goals and expect to hit every one with zero flexibility, you'll suffer more than you benefit. Long-term goals stay fixed. The weekly and the daily stay flexible. Most goals we set at first aren't relevant. In a world changing daily, revisit the plan constantly. Faith matters in the arena. Early on, I was often anxious about money, but the universe never disappointed me. There were always lessons in the making. If you do what you're supposed to do and give your maximum effort, there's nothing to worry about on the outcome side. That's Stoicism. Staring at the bank account, angry about the leads that didn't come, is a scarcity state. You attract flies with it. Fall in love with the game, the grind, and the rest happens by itself. Business is enlightenment. The greatest benefit of being an entrepreneur isn't cash or freedom. It's becoming a better human being. Ask better questions. Am I in the right niche? What am I missing? How can I see this differently? Questions are the key to the magic. What fairy tale could I be stuck in right now? Play: The Experimental Mindset. If I had to pick one mental tool that's responsible for an outsized share of my results, it's this one. On paper, it's simple: I take way more shots than most people. That doesn't just mean discipline; it means not getting emotionally knocked over by negative responses. I'm constantly taking bets and noting the outcome. In business, in fitness, even in dog training. Today I'll take one of the 4 dogs out alone right after he eats and see what happens to his behavior and the other 3's. Outcome: the dog behaves better. Noted. When I need pure data, I give my experiments to an AI and argue with it for a while. Otherwise, I trust my gut. The result? I hit most of my moonshot goals sooner or later, and the negative feedback in between is just noise. It's the same as the voices during an ultra. They're part of the adventure, but they don't get the wheel. Play. Lessons from a 70K training run. 1. Overthinking kills energy. The less you think, the more power you keep. Most entrepreneurs burn fuel obsessing over things they can't control. Meditation trains you to think about what matters and drop the rest. 2. Don't let your frontal brain hijack the ride. At kilometer 45, I started to bonk, and my brain asked the wrong question: How the hell are we getting through the next 25K? Ultras, like business, are waves— 10 highs and 20 lows. If you assume a low will last forever, you trap yourself. 3. Adversity is fuel. At kilometer 55, it started pouring. Most people would quit, and that's where I doubled down. Extra challenge, extra credit. Finish strong, no matter what. The last climb up my street, the right song, my wife cheering, a bit of hallucination, and I don't think I've ever run faster. Finishing strong gives you confidence for the next event. What a 24-hour team race taught me about leadership. I signed up for a 24-hour Spartan endurance event in winter in Vermont because I felt myself plateauing. Physically it wasn't the hardest thing I've done. But it taught me more than most races. Regulation beats intensity. I threw up early, misread a gear requirement, equipment didn't arrive and the tasks kept changing. None of it rattled me. Not panicking saved more energy than any fitness advantage could. Team over individual. I showed up a lone wolf and left with a pack. The next level isn't heroics; it's orchestration. Kindness is a force multiplier. Under pressure, being calm and kind bought us grace, flexibility, and trust. Being an asshole isn't toughness; it's inefficiency. Courage without discernment is just ego. Knowing when not to push is part of maturity. What 1,000 CEOs Taught Me. After a long stretch of 15 CEO interviews a day, here's what I saw beyond the surface-level advice. The best use deep tech stacks and AI heavily. It's less outsource, outsource, and more systems on systems on systems. That takes a hacker mindset. Endurance athletes make great CEOs. Some days are a barrage of pain. Top CEOs go through them without permanent damage. Pain tolerance and patience correlate. Independent thinkers make the best CEOs. They talk about everything, because everything is business in the end. They're open books. They share data in the name of experimentation. They're weird, and they lean into it. Part 7: Money and Freedom. Notes. Notes. My definition of wealth is radical independence. Not depending on anyone or anything, from money to time to my values to who I spend my days with. It took me a good 10 years to get there. Lots of hard work, lots of friction, lots of heart-wrenching moments. Freedom means choosing. Money gives you the wings to choose good over bad. Most people bend their ethics to fit how they make money. FU money is noble for one reason: you're nobody's hostage. To keep high ethics at scale, you have to get rich. As long as you depend on one client's satisfaction to pay your people, you'll agree to be the nice guy even when the client is wrong. Rich people think in decades. Broke people think in paychecks. You get rich by owning, not earning. High-income skills beat frugality. Cutting coffee won't make you rich. Learning to sell will. You don't need more money. You need more leverage. Your first dollar 100k is pure suffering. Everything after that is easier because the hard part is momentum. Your network is an ATM. Rich people help rich people make money. Build a high-value network. People who chase only profit risk emotional bankruptcy. It's not passion or profit. Nerd out on your passions, see if you can monetize them, and A/B test them with pure cash flow ventures. Following the money and nothing else is an endless quest. You get the never-enough type. Overnight millionaires fall harder. I don't want to get lucky. The only non-obscene answer to what would you do for a million dollars is provide value. That's what society was built on. If you're reading this, you have the internet. That means you can start a business with zero capital, learn any high-income skill for free, and build a network of top operators without leaving your house. 50 years ago, that was impossible. The biggest wealth gap today isn't money. It's mindset. Partner with ambitious co-founders instead of starting everything from scratch. You give up equity, but it's energy-efficient, avoids total losses, and scales. One needs about 10 moonshot attempts before one hits. Money buys freedom, not happiness. The goal is what it unlocks. The founder who's making money but isn't satisfied. Lots of founders make good money and still feel empty. Usually it's because of who they serve. If your buyers negotiate every dollar, compare you to cheaper alternatives, and threaten to leave, you'll start to look and feel like them. The fix isn't a bigger number. It's a better customer. Work with people you want to be like. When they pay you and also feed your fire, money and satisfaction stop being opposites. Play. Digital Nomad Math. My Canadian passport lets me stay 6 months or more in lots of places. I spent years living mostly in Mexico, running a company built to work from anywhere. Freedom isn't a visa or a citizenship, it's a business model. If your income needs you in one specific office, you're not free yet. Design the company so your location is a choice. From Partners to Empire. I met Sunny Ray about four years ago. He was first a client, and I generated 300 plus leads for two of his companies. He listened to my feedback. We tried a bunch of things, and it worked. Then he referred me 50 plus clients. So I said, "I like you. You like me. Why not team up?" He came in as a co-founder at Raz Rocket, then at GTM Ventures and Podpire. We agree on about 95 percent of things business-wise, which is rare given the thousands of micro philosophies under my macro mental. Model. We disagree often and invite the debate. Just like in a marriage, that's healthy. Our moat is a funnel most people don't understand. Convert clients into partners, then share revenue or equity in the best projects. It's a venture studio meeting a consulting firm. The best clients become friends. The best friends become partners. That's how you compound. Part 8: The Biohacked Founder. None of this is medical advice. It's what I did to my own body. Talk to a doctor before you copy any of it. Notes. Notes. Energy is everything in the productivity game. Your body is a system. Run it like one. If you chase comfort, you get pain. If you chase pain, you get comfort. Pain is wisdom. It brings your traumas out, exposes your flaws, and shows you the shortcuts you've been taking, so you can replace the broken parts with titanium. Sport has saved my life many times. It pulled me out of drinking and trouble and turned me into someone I'm proud of. I have obese genes, and I was always outpaced at sports when I was younger. I took it into my own hands. Endurance sport taught me to slice long, impossible things into small, doable chunks. That's also how you build a company. We run because it's boring, not because we like it. A 30K means at least 300 F-offs to the demons telling you to stop. Go into the hard stuff with no expectations. Reality is always different from the plan. If it hurts more than expected, don't make a drama of it. Stay flexible and move on. The greatest growth a seasoned CEO can get is through painful endurance events done together. If we connect through pain, we may be adventure partners for life. I don't eat for flavor. I eat for clarity. One wrong meal can cost you a whole day of brain. Caffeine was my crutch. Quitting it didn't give me more energy; it stopped me borrowing energy from later. The real flex isn't more energy; it's calm, controlled execution. Coffee makes you go, go, go. Not every problem is solved by going faster. Once I quit coffee, I noticed how many other dopamine loops I was stuck in. Sleep routine. Look at the stars, lavender, and read Wikipedia instead of business books. Business books inject cortisol. Pirate history puts me to sleep. Play reduces cortisol and increases creativity. Play with your dogs, make your partner laugh, make yourself laugh. Play. What 1,000 lunges teach you. One weekend while everybody else was chilling, I did 1,000 lunges, 1,000 jump ropes, 500 jump lunges, 500 dips, 500 push-ups and 500 jackknives. What I learned? Pain brings the child out. Help me, save me. Being an adult means handling pain and protecting your family from too much of it. Leading is carrying something on your back and going for more. No expectations. Reality never matches the plan. Readapt the strategy to get through the reps. Keep cortisol low and ride the endorphins. The inner coach takes over. You say you'll do something? You do it. You finish it, whatever the time and whatever the form. I later did 2,100 jump squats, 1,100 push-ups, and 600 jackknife crunches on a YouTube Live. 2.5 hours of pain and 7 days of a crippled body. Why? Because the long-term grit outweighs the short-term damage. Play fasting my way. I've done multi-day water fasts. Here's what I noticed. The brain handles stress better in a fasted state. I had brutal days during one fast and still slept well. The first time is hard— headaches, sluggishness. It gets easier once you've done other hard things. Ultras, vipassana, climbing a mountain— all add layers to the mindset. The mind thinks about food constantly, just like it wanders during meditation. Keep it busy with work and light movement. The most dangerous moment is celebration time after. Break the fast gradually. Play: The endurance résumé? 3 Ironmans. A 100K in the mountains of Puerto Vallarta. The 110K UTMB Paraty in Brazil with 4,800 meters of climbing, much of it run half in a dream state. Spartan ultras. A 24-hour winter Spartan in Vermont. Climbing Mexico's highest peak. I'm not telling you this to flex. I'm telling you because every one of those events taught me something I later used in business. Waves. 10 highs and 20 lows. A low never lasts forever. Regulation first, action second. Teams beat heroes. Finish strong. It sets up the next one. Play the Founder Pack. I've been trying communities for years. I'm not naturally a community guy. I'm the alien in most rooms. So I started my own CEO groups. Here's what I learned about which ones survive. You need a growth engine bringing you enough high-level founder leads to handpick each group. People need financial skin in the game. Accountability gets stronger when it costs something. You have to prove the ROI of the group. Plug big shots in with other big shots. You have to be a great mediator so everyone gets their time. Then add pain. We've done ultra heights on Zoom, 100K park loops, mountain climbs, Spartans, ice-cold rivers and saunas in Montreal. And masterminds in the mountains of Oaxaca. People reveal their best selves under shared hardship. That's where the real network is built, not at a networking event. Last page. That's it for now. Everything in here came out of the same loop: take a lot of shots, write down what happened, keep what worked, share it, go again. This book is just the loop printed on paper. If we met on the podcast, thank you. A lot of these lines exist because you answered a question honestly at 7 a.m. your time. If you want to talk GTM, fundraising, podcasting, or which ultra to sign up for next, hit me up. I reply. Go take 200 shots. Charles.