Founder Self Talk

playthe 5 x 5 x 5 email matrix

If you can't get meetings with this system, you're in the wrong place at the wrong time.

1. Write down your ICPs. Start with 5. Example: fintech CEOs with $5M in funding, 7 people on the sales team, using HubSpot, headcount growing.
2. For each ICP, write 5 pain points. Cost, hiring agencies, staff turnover, broken internal comms, broken systems.
3. 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 x 5 pains x 5 solutions = 125 emails.

That's 5 pain campaigns per ICP, each with 5 emails, one solution per email. 25 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.

playthe 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
• = 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.

playwhy some emails get replies

I once had a campaign getting 2 to 5 positive replies a day on autopilot. Here's why it worked:

1. 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.
2. The email was lightly personalized.
3. It was informal, short and simple. It wasn't formatted like a cold email, so people didn't read it as one.
4. No links in the email, so it stayed away from spam filters.
5. It mentioned YouTube, which people trust.
6. The call to action was tiny: "can I share it here?"
7. 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 homo feelians. People still remember their uni days. The reply rate showed it.
• niched 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 two.

playmap 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:

• cold reply -> soft interest
• soft interest -> content consumed
• content consumed -> value received
• value received -> meeting booked
• meeting -> 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.

playmoney days

About 2 or 3 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 a 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.

playwhat 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 5 IPOs answered my M&A questions. People sent me AI apps that replaced parts of my team.

playthe 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 cofounders. People who are not on the monetized podcast trend are missing out.

playthe podcast funnel, step by step

1. 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 ICP: 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 guest 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.

3. 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 cofounders.

Treat your podcast like a sales pipeline, not a side hustle.

playthe 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 a 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.

playwhy the podcast beats the billboard

The best example of all this happened in 2026. OpenAI bought TBPN, a daily live tech show started by two founders, for a reported nine 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.

playpick your VICP

I started out working with realtors. Most were making $100k a year, some $300k. 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 five 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.

playthe 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 two weeks of work instead of my one-month minimum. Normally I don't feel good doing anything under three 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.

playyoung 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.

playcontracts and trust

For small engagements, I don't obsess over contracts. If someone wants to cheat me upfront, 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 six 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.

playthe fundraising machine

Investor demand -> narrative -> pipeline -> process -> close.

1. Demand. Build a list of funds and angels that actually invest in your stage, your sector and your check size. Not "VCs". Your VCs.

2. 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.

3. 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 RaaSRocket 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.

playsolving the lead investor problem

Here's how most seed rounds die. A founder spends three 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:

1. Stop looking for a lead first.
2. Go to 20 to 30 investors aligned with your thesis and ask one question: "if a lead closes, are you in?"
3. Collect soft, conditional commitments. No pressure, no terms.
4. 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.

playbuild 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.

playmy three best systems

The three systems that paid me the most while I slept:

1. The podcast. Episodes keep getting watched without me doing much. Guests reshare them, shorts get cut, search engines index them.
2. Cold outreach. Emails go out to my ICP every single day and book meetings automatically.
3. 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.

playSOPs 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 SOPs.

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?

playthe 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, five dogs, a company. "Good luck surviving that."

Here's how it works:

• Dogs -> walk or run twice a day. Non-negotiable.
• Family -> real support, nannies included. Energy over ego.
• Life -> buy leverage. Tech, help, anything that removes friction.
• Health -> 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 Y.

Being an Ironman, being a founder and being a dad run on the same principle.

playmy 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.

play21 questions for your next planning session

1. What did I miss yesterday that actually matters today?
2. What's the deeper structure underneath this problem?
3. What assumptions am I making that might be wrong?
4. What's the opposite of my assumption, and could it be true?
5. If this idea failed, what would be the real reason?
6. If it succeeded wildly, what made it work?
7. What question should I have asked instead?
8. Where is my biggest leverage bottleneck right now?
9. If I 100x this plan, what breaks first?
10. If I 0.1x this plan, what becomes trivial?
11. If I had to solve this in 24 hours, how would I do it?
12. With zero budget?
13. With 10x the budget?
14. What would the highest version of me optimize for right now?
15. What would make this problem irrelevant a year from now?
16. What's the one move today that creates the most leverage tomorrow?
17. What breaks if this suddenly scales to 10,000 users?
18. And to 100,000?
19. Where am I still thinking like an operator instead of an architect?
20. What's the simplest way to do this at a world-class level?
21. What am I avoiding looking at because I know it's the real issue?

playthe 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 four dogs out alone right after he eats and see what happens to his behavior and the other three'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.

playlessons 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 km 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. Ten highs and twenty lows. If you assume a low will last forever, you trap yourself.

3. Adversity is fuel. At km 55 it started pouring. Most people would quit, and that's where I doubled down. Extra challenge, extra credit.

4. 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.

playwhat 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.

playwhat 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:

1. 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.
2. 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.
3. Independent thinkers make the best CEOs. They talk about everything, because everything is business in the end.
4. They're open books. They share data in the name of experimentation.
5. They're weird, and they lean into it.

playthe 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.

playdigital nomad math

My Canadian passport lets me stay six 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.

playfrom partners to empire

I met Sunny Ray about four years ago. He was first a client, and I generated 300+ 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+ clients. So I said: "I like you, you like me, why not team up?" He came in as a cofounder at RaaSRocket, then at gtm.ventures and PodPire.

We agree on about 95% 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.

playwhat 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. Re-adapt 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. Two and a half hours of pain and seven days of a crippled body. Why? Because the long-term grit outweighs the short-term damage.

playfasting, 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.

playthe 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. Ten highs and twenty lows. A low never lasts forever.
• Regulation first, action second.
• Teams beat heroes.
• Finish strong. It sets up the next one.

playthe 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 hand-pick 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 HIITs 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.