Business · 23 episodes
Leadership for entrepreneurs
Every founder eventually runs into the same wall: the tactics that got the business off the ground stop working, and what's left exposed is how they lead people, including themselves. The guests here disagree about the tools — psilocybin, human design, stoicism, tapping, Reiki — but converge hard on one point: leadership capacity is built below the neck, in the nervous system and the body, not just in strategy decks. Vulnerability, presence, and self-regulation show up again and again as the actual lever, not soft add-ons to 'real' leadership.
Where they split is on where authority comes from. Some argue leaders need to relax control and let go of the comparing, judging, above-the-neck operating mode that built their success in the first place. Others insist on frameworks — SMART, the four cardinal virtues, pause-observe-decide — that impose discipline on emotion rather than dissolve it. Both camps agree that fear-based, survival-mode decisions produce worse outcomes than decisions made from steadiness, and that teams sense the difference immediately.
The recurring failure mode isn't cruelty or incompetence — it's founders who never separated their identity from their title, who couldn't delegate, or who ran their body and sleep into the ground while insisting the business needed them to. Selling the company, losing the CEO seat, or simply admitting fault in front of the team turn out to be the moments that actually test whether someone was leading or just performing leadership.
What holds across every conversation
- •When you catch yourself deciding out of fear or urgency, pause and name it — fear-sourced decisions optimize for your emotional wounds, not for the business's actual interest.
- •Apologize first and visibly when you react badly as a leader; guests across industries independently point to this as the single fastest way to build trust with a team.
- •Don't wait until you're depleted to build recovery practices — sleep, breathwork, and a wind-down routine are leadership infrastructure, not wellness extras, and their absence shows up in your decision quality before you notice it yourself.
- •If you're still the person answering the 800 number or setting your own meetings, you haven't delegated — that's the ceiling that caps founders around $1M in revenue.
- •Separate your identity from your title deliberately, before a sale, ouster, or pivot forces the separation on you; the identity crisis after losing a role is often harder than anything that happened while building it.
- •Build a small, specific reset practice (a walk, five minutes of silence, a breath sequence) you can use in the moment stress hits, rather than only planning big lifestyle changes for someday.
Vulnerability as a Leadership Skill
Multiple guests describe vulnerability not as weakness but as the mechanism that earns trust and unlocks performance from teams.
“If I'm vulnerable at all, then I won't be respected. But it turns out, when I do it from a place of intelligence, then people felt more safe. Because when I'm vulnerable, then they can let down their guard.”
Emotional Intelligence & Manifestation with Randy Lyman · 8:05· listen →
“Our power as leaders doesn't come from our title. It doesn't come from our intellect. It comes from, are we able to get the people we work with to get on board with the vision?”
Emotional Intelligence & Manifestation with Randy Lyman · 23:40· listen →
“We as entrepreneurs and leaders, that's what gets us where we are, is we think we have this energy above our neck most of the time. We're comparing, we're contrasting, we're judging, doing all the things that make our companies better, that make us better. And so I have to coach them to let go of that and to relax and be vulnerable and release expectations.”
David Kahl: From $100M CEO to Psilocybin Guide · 32:05· listen →
“We're not, we're not just colleagues and coworkers. We're actually mothers and fathers and caregivers. We're real people. But often we get stuck in this, you know, we're these human resources. We're not, we're not human resources. We're actually humans.”
Bart Foster: Business Outside and the Power of Nature · 13:44· listen →
Deciding from Fear vs. Presence
Fear-driven, survival-mode decisions and presence-driven, values-aligned decisions produce structurally different outcomes for the leader and the business.
“We need to be very agile how we navigate in those times. To be agile, we need to be in that growth mindset, in that abundant mindset. So the framework helping me to pause, observe, and decide, that framework, if I practice it, I enter quickly into the abundance mindset and get out of the fear of the survival mindset.”
Conscious Leadership: Deciding from Presence, Not Fear · 5:46· listen →
“Okay, we want to achieve something, but who says we will achieve it? We decided. Okay, it's a game. So the moment I understand and come a little bit more relaxed about that, it's a game. So let's play the game the best we can. Then I become agile, then I see the waves, and then I can adjust whatever needs to be adjusted in the moment.”
Conscious Leadership: Deciding from Presence, Not Fear · 20:26· listen →
“It's okay to let the world burn for a while. So, you think you need to fight every fire, but if you let it burn, usually it's not as bad as you think. And then in stillness, you find clarity.”
Phil Neil: Emotional Mastery & Entrepreneurial Reinvention · 19:58· listen →
“Fear restricts. Fear holds back. Fear makes people timid in the process. Whereas when you empower your employees, where you empower your leadership team as a C-suite leader perhaps, when you empower those people and build them up and encourage the dialogue and encourage the conversation, encourage in a respectful way the challenges to maybe to what's being done, that just sets you up for greatest success.”
Anthony DeNino: SMART Mindset for Entrepreneurs · 16:57· listen →
Identity Beyond the Title
Losing a company, a CEO seat, or a founder role forces a reckoning with how much of one's identity was actually the job.
“I essentially, I got forced out of the company I founded and it was really hard for a few months. And I, you know, for me it was so much of my personal identity because I founded the company, you know, and without the CEO title, like, who am I?”
Bart Foster: Business Outside and the Power of Nature · 4:31· listen →
“After it happened, it was probably the most difficult period of my life. I mean, even more difficult than growing and scaling the company because like, as I said, when you're like, when you're in it, John, you don't realize how much you're in it and how much of your every living drop of energy is going into it.”
David Kahl: From $100M CEO to Psilocybin Guide · 15:57· listen →
“some people express like the exhaustion they have for carrying all the damn masks way too fucking long, if I can say it that way, because that's how they feel. They're like, and here I am, I've got my own company, right? It is being successful, and I'm still not free.”
Dr. Jax Black: Redefining Success Through Joy · 28:58· listen →
“Potential is what you see, potentiality is what we can't even see. We live in this world where, yes, we wanna maximize our potential, but that's actually not the ceiling, that's the floor, because we don't let that expansion of the magic that can happen, the trust, the alignment, like all the invisible take its step.”
Sara Gilbert: Intuition, Language & Leading with Courage · 3:23· listen →
Culture, Accountability, and Trust
Whether it's a locker room or a boardroom, guests point to the same behavior separating high-trust cultures from cover-your-ass ones: who admits fault first.
“There's a cover-your-ass culture in the NFL because if you don't have security or you haven't won recently, you're on the line. That's coaches, that's general managers. No one wants to tell the owner bad news. So it always is someone else's fault. So the spotlight's off them and on somebody else.”
From NFL to Entrepreneurship: Justin Pugh's Playbook · 28:22· listen →
“I don't know if I believe in balance. I think some days it's like 80/20 and some days it's like 60/40. We had this business now for 27 years... I never had balance. Somebody something always got left.”
Positive Activity: Daily Mindset Habits with Lori Rogers · 20:55· listen →
“If you leave things unsaid, then they fester. They fester in a marriage. They'll fester in a partnership. And then they blow up. And when they blow up, sometimes it's irrecoverable.”
Personal Branding for Entrepreneurs with Alan McLaren · 32:29· listen →
“I have something called 4-3-2-1 and everybody should have these in their proverbial backpack. 4 stories, 3 quotes, 2 facts, and 1 question.”
Bart Foster: Business Outside and the Power of Nature · 15:57· listen →
The Founder's Physical and Emotional Fuel
Sleep, breath, nervous-system capacity, and unresolved emotional weight repeatedly surface as the hidden infrastructure behind leadership performance.
“There was also a 2012 study in Stockholm where they found that the strongest predictor of burnout across about 500 working individuals, it wasn't work hours or demands. It wasn't thoughts of work on days off or leisure time. It was too little sleep, right? Sleeping less than 6 hours.”
Sleep Science for Entrepreneurs with Dr. Elie Gottlieb · 17:08· listen →
“I'd rather have the surgeon who slept 9 hours that maybe didn't go to the best medical school over the Harvard surgeon who is only working on 2 or 3 hours of sleep. That's how much I know about the effects of sleep deprivation on cognition, on performance.”
Sleep Science for Entrepreneurs with Dr. Elie Gottlieb · 21:23· listen →
“I'm not going to go into the gym on day 1 and try to lift 100 pounds off the rack. You know, I'm going to go with a 5 or 10-pound weight. And then over time, I'm going to slowly increase the amount of weight that I can lift until I get to that 100-pound weight.”
Cognitive & Embodied Awareness with Carissa Karban · 22:30· listen →
“A lot of people were sold on this idea that you're supposed to get less sleep. And because of that, that means you're working hard and get up at 5:00 AM and all this crap... I mean, for some reason, it feels like you're accomplishing something, but you're really just depriving yourself of higher brain function, honestly.”
Debt Strategy for Entrepreneurs: Leverage Without Crushing · 34:00· listen →
Letting Go of Control to Lead Well
A counterintuitive theme across founders who worked with psychedelics, coaching, or conscious-leadership frameworks: the comparing, judging, controlling mode that built the business has to be set down for the next stage of leadership to work.
“We as entrepreneurs and leaders, that's what gets us where we are, is we think we have this energy above our neck most of the time. We're comparing, we're contrasting, we're judging, doing all the things that make our companies better, that make us better. And so I have to coach them to let go of that and to relax and be vulnerable and release expectations.”
David Kahl: From $100M CEO to Psilocybin Guide · 32:05· listen →
“The mushroom is a bit of a house cleaning mechanism that helps you to make decisions and choices to move forward. So the vessel, the human vessel, is sort of like stronger and cleaner as you move forward in decision making.”
Conscious Leadership Through Psychedelic Journeys · 13:07· listen →
“I believe entrepreneurship is a hero journey, which means that you step into the unknown. But the way we're approaching entrepreneurship right now is we're doing it in reverse. We're aiming for tactics, tools, skills that we can plug and play into a trail that's known in our forest.”
Phil Neil: Emotional Mastery & Entrepreneurial Reinvention · 21:44· listen →
“It's more of setting that intention, going into space and just stepping in and relaxing and trusting yourself, trusting the conversation and knowing that the right people in that moment will always come find you.”
Mel McSherry: Human Design & Mental Profitability for Founders · 6:32· listen →
The companion guide
Reading about leadership is one thing. Changing it is another.
John’s companion guide turns what these conversations cover into something you can actually work through.
More moments worth hearing
Everything else these conversations turned up on this subject.
“I believe every single human being has the beautiful power within them to transform, to come home to themselves, as I like to say. And so my role is really to provide the safety, the love, the education, and the tools that people need in order to kind of cross that bridge into self-transformation.”
Cognitive & Embodied Awareness with Carissa Karban · 2:25
“Everything is a choice. Truly, everything is a choice to wake up, to say yes, to say no.”
Cognitive & Embodied Awareness with Carissa Karban · 6:12
“I said, okay, well, I see the divorce and I raise you. I'm quitting the job, selling the house. I'm gonna go on this travel sabbatical and just, you know, kind of my own little Eat, Pray, Love adventure because I knew that I could handle whatever came my way.”
Cognitive & Embodied Awareness with Carissa Karban · 14:50
“It's really hard for judgment and curiosity to coexist, 'cause if we can truly embody curiosity and say, huh, where does that pattern come from? Why do I think that? What am I afraid is going to happen? Then that's where we're really opening a door rather than judging something and closing a door.”
Cognitive & Embodied Awareness with Carissa Karban · 16:19
“I also really love the one, worrying is like a rocking chair. It'll pass the time, but it won't get you anywhere.”
Cognitive & Embodied Awareness with Carissa Karban · 34:58
“How is this happening for me? Not to me. What is this teaching me right now? Okay, a little patience, a little calmness. So when your brain is working from a higher vibration and it's more positive and optimistic, ideas flow to you easier.”
Positive Activity: Daily Mindset Habits with Lori Rogers · 12:23
“Our brains work in the opposite way... Be it first before you see it, right? So I don't mean pretend, but I mean, go to the emotion of having it now and then see what happens.”
Positive Activity: Daily Mindset Habits with Lori Rogers · 16:55
“On top of my vision board, it says, this or something better... The universe says, no, no, no, this over here is gonna be amazing for you and you don't even know it yet.”
Positive Activity: Daily Mindset Habits with Lori Rogers · 18:42
“I asked him one day how he knew so much about love, and he spelled out, I learned it from Jesus Christ.”
Positive Activity: Daily Mindset Habits with Lori Rogers · 32:14
“Society tells us we're going to be happy when we get there. And you're right, they get difficult because in order to take a business beyond a certain level, we have to be able to connect with people in the way they can feel us.”
Emotional Intelligence & Manifestation with Randy Lyman · 2:55
“So, people need 3 things... They need to be acknowledged for who they are as an individual. They need to feel like they're contributing to the cause. They want to have meaning in their life... And then, they want to feel like they belong to the group and they want to feel safe within the group. So, those 3 things are more important than money.”
Emotional Intelligence & Manifestation with Randy Lyman · 6:38
“It's a 3-legged stool, and we could sit on a 3-legged stool, but you take one of those legs away— thoughts, actions, or emotions— and don't consider all 3, then we tip over.”
Emotional Intelligence & Manifestation with Randy Lyman · 22:25
“When I started incorporating the emotional side of life into my own growth, and then my business, the business grew 30 times. We're not talking 10x. We're talking 30x.”
Emotional Intelligence & Manifestation with Randy Lyman · 22:25
“I hold my vision. This is my goal. And I say, this or better. And I keep working towards my goal, but I'm always open to other opportunities and other guidance.”
Emotional Intelligence & Manifestation with Randy Lyman · 27:15
“I think that's a big mistake with serial entrepreneurship is people see it as diversifying their risk. But because the root cause of startup failure is the internal mismanagement that derails decision-making, what will happen is that you're going to be fighting fires everywhere.”
Phil Neil: Emotional Mastery & Entrepreneurial Reinvention · 16:46
“You manage them like you manage a plant. You won't water a plant if it's raining for a week. So, just as you don't have to water your energy if you've been at a Spartan Race boot camp for a week.”
Phil Neil: Emotional Mastery & Entrepreneurial Reinvention · 18:50
“I think part of the answer is acknowledging that the real treasure is not the exit. It's the broken icons that you had when you started the journey about how it should play out, who you are, what are your skills that are being destroyed by the reality of the experience that you can now integrate into wisdom.”
Phil Neil: Emotional Mastery & Entrepreneurial Reinvention · 28:20
“We confuse hustling with business and entrepreneurship. To me, they're all different.”
Phil Neil: Emotional Mastery & Entrepreneurial Reinvention · 26:13
“You don't get the journey you want, you get the journey you need. And so my journey was nothing like what was— nothing came up that gave me any indication about what was next for me. What came up for me were a lot of things from my past that I thought I had processed, but I didn't process.”
David Kahl: From $100M CEO to Psilocybin Guide · 20:26
“So I quit my job that day. I felt it so strongly, John. I knew what was happening and I just didn't want to be there. I'd come off the street with complete strangers feeling a deep connection and I got into this workspace and I was like, this isn't my environment.”
David Kahl: From $100M CEO to Psilocybin Guide · 10:22
Every episode on leadership
23 conversations, oldest to newest.
Cognitive & Embodied Awareness with Carissa Karban
Living safely and checking boxes for success often leads to burnout rather than fulfillment.
Positive Activity: Daily Mindset Habits with Lori Rogers
Daily positive activities like affirmations, gratitude journaling, and meditation are scientifically linked to increased sales, productivity, and resilience.
Emotional Intelligence & Manifestation with Randy Lyman
Business success without emotional awareness leaves entrepreneurs unfulfilled, even after reaching high levels of financial achievement.
Phil Neil: Emotional Mastery & Entrepreneurial Reinvention
Three emotions—uncertainty, fear, and unworthiness—derail entrepreneurial decision-making and push founders into a 'shadow' failure zone.
David Kahl: From $100M CEO to Psilocybin Guide
Selling a company can trigger a harder identity crisis than building it, because founders often don't realize how fused their identity is with the business.
Jack Adler on Building Out2Win and Raising $1.3M Young
Jack pivoted his NIL agency into a scalable AI athlete-marketing intelligence platform after recognizing brands lacked data to evaluate athletes as marketers, not just performers.
Lindsay Mastrogiavanni: Spiritual Entrepreneurship & Mediumship
Conscious entrepreneurship means building a business grounded in your why, mission, vision, and values rather than external expectations.
From NFL to Entrepreneurship: Justin Pugh's Playbook
Justin Pugh built NFL Biz Week to teach players financial literacy and deal-vetting skills because most athletes retire with no plan and high bankruptcy rates.
Conscious Leadership: Deciding from Presence, Not Fear
Decisions made from fear and survival mindset produce competition and destruction, while decisions made from presence and abundance mindset align with purpose and values.
Sara Gilbert: Intuition, Language & Leading with Courage
Potentiality is the invisible expansion beyond what we consider our maximum potential, and most people treat their ceiling as a stopping point rather than a floor.
Dr. Jax Black: Redefining Success Through Joy
Joy, not deficits or trauma, is our natural born state, and fear of judgment or failure is taught by others rather than innate.
Mel McSherry: Human Design & Mental Profitability for Founders
Entrepreneurs should prioritize mental and emotional profitability before financial goals, or financial success becomes unsustainable and leads to burnout.
Chris Streveler: NFL Mindset for Entrepreneurs
Mental rehearsal and visualization, standing behind the starter and simulating throws, prepares you to seize opportunities when they suddenly appear.
Personal Branding & Fear of Judgment With Ivana Ivanek
Building a personal brand requires showing your real voice, face, and environment to build trust, not polished perfection.
Sleep Science for Entrepreneurs with Dr. Elie Gottlieb
Chronic sleep deprivation, not workload itself, is the strongest predictor of burnout and undermines the long-term success entrepreneurs are chasing.
Stoicism for Entrepreneurs: Lessons from Ken Davenport
Stoicism trains entrepreneurs to separate what they can control from what they can't, which reduces anxiety tied to uncertainty and outside events.
Debt Strategy for Entrepreneurs: Leverage Without Crushing
Debt is leverage that helps a business grow when used within its cash-flow cushion, but becomes the primary cause of business failure when it exceeds what the business can safely service.
The Clarity Map: Lynn Mull on Purpose and Alignment
Career transitions away from toxic, high-pressure environments often take years and require deliberate financial and emotional planning, not a sudden leap.
Nicole Van Valen on Joy, Spirit & Resilient Leadership
Resilience doesn't have to come from grit and misery; it can be built through cultivating internal, self-sustaining joy.
Bart Foster: Business Outside and the Power of Nature
Conducting business outdoors and walking shoulder-to-shoulder makes people calmer, more authentic, and more vulnerable, leading to deeper connections than coffee or lunch meetings.
Personal Branding for Entrepreneurs with Alan McLaren
Personal branding works best when framed as generous knowledge-sharing rather than self-promotion, which removes much of the anxiety around it.
Anthony DeNino: SMART Mindset for Entrepreneurs
Success follows a four-step SMART process: mindset, emotion, confident speech, and action.
Conscious Leadership Through Psychedelic Journeys
Psilocybin mushroom journeys can act as a 'house cleaning mechanism' that releases habitual patterns and unresolved grief, trauma, or depression.