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Dave Kashen shared thisIf everyone on your founding team agrees with you, what do you actually need them for? Most leaders say they want dissent, then accidentally punish it the moment someone actually disagrees. Or worse, they invite input, get flooded with conflicting opinions, and then freeze. Paralyzed by the weight of all those smart voices saying different things. Here are 5 ways to be both collaborative and decisive at the same time: 1. The missing agreement Most teams don't have a clear agreement on how decisions get made. They discuss things for a while, try to get everyone on the same page, and hope clarity emerges. What actually changes it is clarity about the decision rule (how the decision gets made). In most leadership contexts, the intended decision rule is "leader decides with input." Founders gather perspectives to make an informed choice. But if the team doesn't know that's what's happening, they'll think it's a consensus decision and keep lobbying for their position. The fix is almost embarrassingly simple. At the start of the conversation, say: "I really want to hear your thoughts on this. We'll talk for 20 minutes, and then based on all your input, I'm going to decide." That one sentence settles people. 2. Ask for it explicitly "What doesn't make sense about this? What's wrong with my thinking here? Why might this not work?" When founders are too attached to being right, they get defensive. Letting go of sourcing worthiness from having the answers opens genuine curiosity about other perspectives. 3. Make it safe to disagree If a founder drills in or gets defensive, the message sent is: "This was a trap. Never do that again." Instead: "Thank you so much for bringing that up. I hadn't thought of that." Teams get more of what leaders appreciate. Founders who want people speaking up should appreciate when someone takes the risk. 4. Practice conscious listening This is where most leaders lose the game. They ask for input, then don't actually demonstrate they've heard it. Conscious listening means listening from the head (what are they saying?), the heart (what are they feeling?), and the gut (what do they want?). Repeat it back: "I hear you saying we should do this because of X and you feel Y and really want Z. Is that right?" When people feel genuinely heard, they can disagree with the decision and still commit to executing it. 5. Decide Decisiveness means feeling the doubt and deciding anyway. Indecision is a feeling problem. Founders wait for a certainty that will never come because they don't want to feel the fear of being wrong. The role of a leader is to decide in the face of uncertainty, which means deciding in the face of fear. A team doesn't need its founder to have all the answers. It needs to feel heard, and it needs a decision. Everything else follows from that. P.S. Repost to help a founder in your network ♻️ And follow Dave Kashen for more.
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Dave Kashen reposted thisDave Kashen reposted thisWhen clients tell me they don't know what they want, I ask them what they're angry about. Anger is the fastest shortcut to buried desire. Every resentment is a want you abandoned. Name the anger, and you'll find the want underneath it.
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Dave Kashen shared thisThe secret to becoming a more effective leader is to stop trying to improve yourself. I know that sounds counterintuitive… because how else would you become a more effective leader? Well self-improvement tends to begin with the idea that there’s something wrong with you and focuses on how to fix it. Moreover, in most self-improvement efforts the mind goes through what people call the 'self-ing' process, where the mind builds up and strengthens an image of itself that it holds and tries to improve. This reinforces the idea that who you are is the image your mind has of you. But you begin to unlock a deeper truth when you see that the image your mind has of you is itself just a thought. From that space, you can adopt new behaviors and see what’s in the way of actually serving your people and company best instead of simply trying to preserve or aggrandize your currently held self-image. But people don't start with a fixed self and then defend it. The act of defending creates the self. Every moment of grasping, resisting, or managing perception literally fabricates the identity you think you are. One of my clients, a founder who'd just raised $30M, came to me in complete overwhelm. "I can't stop trying to control how I'm coming across," he said. When we explored what would happen if he let go of being "the confident, visionary CEO," he literally started shaking. His nervous system was interpreting the dissolution of that identity as a survival threat. But here's what I've learned: that just means it's “unfamiliar”. As I often tell clients: "The conditions we learned to survive in become the conditions upon which our continued survival depends." You learned to survive by constructing this identity. Of course your system resists letting it go. The practice is to stay with that fear, to welcome it, to feel it., and to let it move. You don’t have to eliminate it. You just have to stop identifying with it. Your mind will keep creating stories about who you are. That’s what minds do. But you can learn to observe those stories without getting caught in them. You’re not the image your mind is trying to protect. You are the awareness in which all of that arises and passes. And from that place of recognition, leadership becomes natural and effortless. You’re simply responding to what this moment requires. The less you focus on appearing as a great leader, the more your natural leadership emerges. Because when you stop defending a prison you never needed, you discover a freedom you've always had.
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Dave Kashen shared thisYour manager has a greater impact on your health than your doctor. Think about what that means. As a leader, you aren't just influencing KPIs and quarterly results. You're shaping the mental and emotional health of your people… possibly for years to come. In essence, effective leadership means helping your team grow up. Because as your team "grows up" as human beings, the sum of the parts truly becomes greater than the whole. Each person matures, showing up as their best self, transcending their limiting patterns and collaborating in ways they never could before. But you can't force human development. You can only create the conditions for it to emerge. Here's what I call the C.O.R.E. framework, for creating those conditions looks like in practice: 1. Curiosity over Certainty When someone on your team makes a mistake, resist the urge to immediately correct or instruct. Replace "Why did you do that?" with "I'm curious, what was going on for you when you made that choice?" Model asking questions instead of having all the answers. Show your team that not knowing is often more valuable than being right. 2. Openness instead of Withholding Create an environment where truth is valued above all else. Where vulnerability is seen as strength, not weakness. Share your own uncertainties and struggles. When you reveal your authentic thoughts and challenges, you give your team permission to do the same. 3. Responsibility without Blame Help your team members see themselves as the creators of their experiences, not victims of circumstances. When someone struggles, ask: "How might you have contributed to creating this situation?" and "What would you do differently next time?" Hold them as creative, resourceful, and whole. Don't see them as broken people who need fixing. See them as capable humans who are learning and growing. 4. Empathy for the Human Experience Recognize that your team members aren't just intellectual beings. They have emotions, bodies, and spirit that affect their work. When someone is struggling, get curious about not just the facts but also what they're feeling. Ask: "How are you doing with all of this?" and actually listen to the answer. Remember that behind every "performance issue" is often a human being dealing with fear, insecurity, or old patterns that need compassion, not correction. When humans heal their limitations and step into their potential, they naturally take ownership. They lead themselves. They bring solutions instead of just problems. When you stop trying to manage people and start helping them grow up, they stop needing to be managed. It's not always easy. But it's worth it. P.S. Repost to help a founder in your network ♻️ And follow Dave Kashen for more.
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Dave Kashen shared thisMost founders think they're helping when they jump in with solutions. But most of the time… we're just recycling thoughts the team already had. For example, on one of our early community calls, a founder shared a challenge he was stuck on. He was dealing with an underperforming team member who had potential but low follow-through. He had ideas, but none felt right. He wanted support. Now, here's where most groups would jump into advice-giving mode. You know how it goes: "Have you tried setting clearer expectations?" "Maybe switch to weekly check-ins?" "Just fire him." But that approach assumes the person needs more information. Most of the time, what they actually need is more awareness. Moreover, trying to fix reinforces the idea that there’s something wrong with them or their life; that they are a victim and need your help. So we did something completely different. We asked him questions... and didn't let him answer a single one. Here's how it works: someone shares a real challenge. Then everyone takes turns following their curiosity by asking open-ended questions. The person with the challenge doesn't answer. They just listen. People asked things like: "What are you avoiding feeling?" "How do you know none of your ideas will work?" "What's in the way of you already knowing the answer?" There were no solutions. There was no advice. Just curiosity in question form. And something shifted. I could see it in his posture, his energy. The questions had illuminated something he couldn't see before. It’s easy for founders (myself included) to think our job is to have all the answers. But what if our greatest leadership superpower was simply asking better questions? Not just of our teams, but of ourselves? Try it this week. Write down ten questions about your biggest challenge. Don't answer them. You’ll see that the quality of your leadership is directly tied to the depth of your awareness. And sometimes the fastest way to expand that awareness is to stop trying to be right and start getting curious.
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Dave Kashen shared thisEvery hyper-successful founder I've worked with has confessed essentially the same thing behind closed doors: "I just don't know if I have what it takes." Not just occasionally. But more often than they'd ever admit. They can't tell the difference between doubt that serves them and doubt that sabotages them. So they either fight all doubt (which is impossible) or listen to all doubt (which is paralyzing). Destructive self-doubt makes it about your identity. It sounds like: → "Maybe I'm not really a good entrepreneur" → "Maybe I can't do this" → "Why did you think you could do this?" → "Maybe I'm not good enough" This kind of doubt attacks your fundamental worth as a person. It's binary thinking: either you're good enough or you're not. Destructive self-doubt makes your identity dependent on your performance. On the other hand, healthy self-questioning focuses on functional discernment. It sounds like: → "How could I be better?" → "How am I awesome at this? And how am I not so awesome at this?" → "Where do I have opportunities to improve?" → "What am I doing that's going great and working really well?" Healthy self-questioning treats challenges as information you can work with. The difference is profound. Destructive self-doubt makes your identity dependent on your performance. Healthy self-questioning treats challenges as information you can work with. Your doubt doesn't make you different from successful founders. It makes you exactly the same as them. Rather, welcome and appreciate the doubt for being there. Because ultimately, it is just trying to keep you safe. But with this understanding – and in seeing the difference between healthy doubt and destructive doubt – you can choose to only listen to the doubt that further empowers you. You already have everything you need. You just need to remember that you're equal to every founder who's ever built something that mattered. Including the doubt they felt along the way. P.S. Repost to help a founder in your network ♻️ And follow Dave Kashen for more.
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Dave Kashen shared thisA founder asked me recently: "Should I wait until fear and lack have gotten me to my number, to my exit, and then do the deep work?" He was considering my next retreat in Sun Valley. He'd been in a group with post-exit founders doing inner work, and he wanted to know if he should wait. Because fear worked. It brought him this far, so why mess with it now? This is the ultimatum many founders find themselves stuck in. Founders know they're running on dirty fuel (fear, lack, proving something) and they see it's exhausting them. So they want to let go of the attachment, but they are scared of not being scared and having nothing to motivate them. They are afraid they’ll stop caring as much about everything. That the vision that used to excite them feels distant. The mission will feel like just words on a wall. That they’ll slide from attachment into apathy. And that apathy will kill their company. So the question becomes, how do you care deeply without being attached and falling into apathy? Click below to read the full newsletter ⬇️
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Dave Kashen reposted thisGreat leadership starts with three words the majority of founders avoid: “I don’t know”. Here’s what I mean: When you “know”, you are relating to the current situation from the past. When you are in the past, you are not in reality. You are in the mind experiencing memory, which no longer exists here in reality. So the bridge outside of the mind into the present moment, where everything is real, alive, and true... is curiosity. Or in other words, saying the words "I don't know" and seeing everything for the first time with all its novelty. I watched it happen during a coaching call when a founder was spiraling about his Series B fundraise. The data room had been live for less than twelve hours… Only two investors had accessed it so far, and his mind was already catastrophizing: “Maybe I need to talk to my team about what happens if we don't raise money.” “Maybe I should pivot the strategy.” “Maybe…” "There's this knot in my stomach," he said, his voice tight. "Like everything's closing in." I replied "Good. Just be with that for a moment." I could hear him breathing on the other end of the line. "You know what's interesting?" I said. "You're trying to solve a problem that doesn't exist yet. The fundraise isn't failing, you just don't know how it's going to unfold." The shift was immediate. His breathing deepened. The frantic edge in his voice softened. "That's... relieving," he said, sounding surprised. "I've been treating this uncertainty like the worst is guaranteed to happen when I actually have no idea." He was living in an imagined future based on past patterns. But the moment he said "I don't know" and got present, everything shifted. Fear draws its power from imagining what could go wrong. And from my experience, fear and wonder can't coexist. When a founder chooses wonder, fear literally can't be there at the same time. Fear makes leaders myopic and stressed. Curiosity is enlivening and expansive. Here's how to practice this: 1. Welcome "I Don't Know" When the anxiety of not knowing shows up, the move is to pause and say, "I'm actually confused about this, and that's okay." Founders can start saying "I don't know" in meetings, with their teams, with investors. And follow it immediately with: "Let's figure it out together" or "What do you think?" Most leaders fight confusion because they think it's a problem to solve. Confusion often signals the edge of a breakthrough, where new information is being integrated that doesn't fit old mental models. 2. Choose Wonder Over Fear When founders catch themselves spiraling with worry, they can interrupt the pattern with wonder questions: "I wonder what this situation is here to teach me?" "What would we do if we started all over?" "What's one thing we've never tried that just might work?" These questions work as doorways into new possibilities rather than quizzes where someone needs to get the answer right. 3rd step is in the comments ⬇️
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Dave Kashen shared thisLeadership maturity is measured in how fast a founder can recognize the pattern they're in and shift out of it. For example: When startups hit a roadblock, leaders often fall into predictable patterns. It's called the Drama Triangle, and understanding it might be the most important leadership skill that most founders don’t even know exists.. Take Evan, a CEO I coached. On a Friday night, he was the last person out of the office. He was working so hard and was so unappreciated, playing out the "poor me" of the Victim. Why are things like this? Then he shifted to Villain and started blaming his team for being lazy and entitled. He next shifted the blame to himself. What's wrong with me? If only I was more charismatic! He went to grab a drink and blow off steam, commiserating with a few of his CEO friends. They stepped into the Hero role, validating his complaints, and that made him feel better (temporarily). But when Monday morning came, it was back through the Drama Triangle cycle all over again. Evan had hired me in hopes of figuring out what was wrong with his team and how to better motivate them. But what he got instead was a deeper understanding of himself and how he created the very thing he said he didn’t want. He became aware that he was operating from a state of threat nearly all the time. He saw how he had viewed himself as a victim of his team’s behavior and blamed them for his frustration. He acknowledged that he was scared of failing. Once Evan became aware that he was below the line and scared, he was able to be compassionate with himself and accept himself as he was. This is important. You can’t shift from below the line to above the line if you haven’t first accepted yourself just as you are. Remember, what you resist persists. As Evan began to shift and take 100% responsibility (without blame), he was able to see how his view of his team as “Villains” was self-fulfilling. In a myriad of small ways, he was sending them the message: “There is something wrong with you.” His being below the line was creating a culture of toxic fear, shame and guilt that made people want to be less and less connected with the company. He owned the impact of being below the line and blaming his team, and began to take action: He revealed all the thoughts he had been withholding about his team, not to be right, but to begin to create a healthy culture and put the past in the past. But then he accepted himself as he was and took action to create the conditions for a highly engaged, thriving team. Notice when you find yourself in the Drama Triangle. Which role do you default to first? How quickly do you cycle to the others? The next time you feel yourself getting pulled into drama, pause and ask: "How am I creating this situation?" This simple question can create the space needed to shift from reaction to response.
Dave Kashen commented on a post
1w
5. Don't Take It Too Seriously
Conflict feels deadly serious when it threatens our need for approval, control, or security.
But this seriousness activates fear, which destroys creative thinking.
Ask yourself: "Will this matter in 5 years, 10 years, 25 years?"
This single perspective shift opens up creative solutions that fear-based thinking blocks completely.
The moment you stop justifying your stories and start exploring reality, the entire dynamic shifts.
I've found that if you're both genuinely open, curious, and willing to commit, you can typically find a win-for-all solution.
P.S. Repost to help a founder in your network ♻️. And follow Dave Kashen for more.
Dave Kashen commented on a post
1w
3. Trust the Present Moment
Wonder requires trust. Trust in life, in a team, and in oneself.
When leaders stop trying to control outcomes and start getting curious about what wants to emerge, they often discover solutions far better than anything they could have planned.
Remember: you're not living in the past (what you know) or the future (what you fear) – you're creating from the present moment where everything is alive and possible.
Within 48 hours of our call, my client stopped trying to figure everything out and instead got curious about what his investors were actually looking for.
He reached out with genuine questions rather than desperate pitches.
Two weeks later, he had three term sheets.
"I realized I was so busy trying to have all the answers that I forgot to ask the right questions," he told me.
That happened because great leadership doesn’t look like knowing all the answers. It's asking the right questions:
"As soon as I admitted I didn't know everything, everyone started wanting to help me figure it out."
The next time you feel that familiar anxiety of uncertainty, try this: take a deep breath and say:
"I don't know... and I wonder what's possible here."
You might be surprised by what emerges.
– DK
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Dave Kashen reacted on thisDave Kashen reacted on thisBack when I was in my twenties, I came across a picture of me when I was crying as a little kid. My parents had been taught to feel uncomfortable about the emotions I was having. So to feel less uncomfortable, they would tease me. It was quite an image: You could see the dumbfounded expression on my face. I couldn’t believe my parents had the camera out. I realized then: “That must be why I haven’t cried in nearly fourteen years...” After I saw that picture, I put it on my desk, and told myself: “I’m going to learn how to cry again.” A whole year went by of that picture sitting on my desk… but I still hadn’t figured out how to cry. I just couldn’t get the tears to come. So I decided to try something different. I went out into the woods to a faraway trail where no one could see or hear me (that’s how much shame I had around it) and I started fake crying. I did that for about three months, just faking it. Until all of a sudden, it started to actually happen: I began to cry. It was one of the biggest reliefs of my life. My body let go of years of tension in just days. I just let myself cry for nearly four days straight — while I was brushing my teeth, while I was eating lunch, whatever I was doing. The most beautiful part I discovered was that underneath all that sadness was a deep, persistent joy and a deeper capacity to feel and love.
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Dave Kashen reacted on thisDave Kashen reacted on thisLinkedin peoples - figured I would share a bit of a professional pivot that I have undertaken over the last year. After nearly 25 years investing in technology and media companies, I left the finance world to try my hand at something more entrepreneurial. I am now helping run a small start-up called Dobson's Choice which produces an all-natural CBD-based muscle and joint balm targeting amateur athletes that don't want to stop doing what they love just because they are sore! We make it in Sonoma, California and sell it on our website (www.dobsonschoice.com) as well as through a network of retail stores, chiropractors/masseuses/acupuncturists, wellness centers, and sports clubs. Would love to get your feedback (good/bad/ugly!) as we have a number of new products in the pipeline and are embarking on a larger wholesale push. Use the discount code PB15 upon checkout for 15% off and let me know what you think!
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Dave Kashen reacted on thisAxiomProver, an AI, published a handful of papers in math journals!Dave Kashen reacted on thisSince February, 8 papers across algebraic geometry, representation theory, number theory, combinatorics have been quietly appearing on arXiv. Proofs by AxiomProver. 5 papers are now accepted at solid peer-reviewed math journals. To our knowledge, a first for the literature. Math journal review cycles can famously take years. Why so fast now? Every proof is generated in machine-verified Lean, then paired with a human exposition. The mathematician authors are there to explain the theorem, not to prove it. AxiomProver produces math one can trust. We sat down with Ina Fried of Axios on AxiomProver's first 100 days as an AI mathematician -- and discussed how our AI went from first-time competing at math Olympiads (Putnam) to publishing journal papers in under four months. https://lnkd.in/g7CRYnYV
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