The Conversation Factory

Welcome to The Conversation Factory, the podcast where we explore the deep mental models that turn difficult conversations into opportunities for clarity and alignment. 
Founding a company is often viewed as a binary choice: win big or fail completely. But what if success isn't about total victory (what would that even mean?) but about mastering the long game, the infinite game,  and the quality of the relationships you make along the way? In this episode, I sit down with seasoned venture capitalist and author of Founder Unfriendly, Charlie O'Donnell, to explore the communication strategies and clear thinking that fuel successful entrepreneurship.
Charlie is a 20-year VC veteran, a Partner at Brooklyn Bridge Ventures, and an active presence in the NYC Startup scene…and his recent book is a very helpful guide for the 99% of founders who will struggle to fundraise. 
​We dive deep into the essential, often-avoided conversations that make or break a startup. Charlie explains why your co-founder is your most important hire—they provide the deep trust, honesty, and pushback that AI really can't - you can't walk away from a real person like you can from your laptop - and a real partner will want to be real honest with you in a way an employee just can't. He also explains why key documents, such as a structured financial plan and weekly hypothesis-and-progress conversations rooted in OKR thinking, are not "fiction" but an essential anchor for strategic conversations, even at an early stage.
We also talk about the power of a "conversational judo" approach to tricky investor conversations and how to marshal the inner resources to steer difficult questions towards your strengths.
One thing I really loved about this conversation was the moment I chose for the opening quote - Charlie was pointing to an idea near and dear to my heart that I've been noodling about -  Emotional Metabolism. As he says, you can't tell someone to feel differently than they feel. No one has an emotional metabolism that is that fast! If you don't believe me, reflect back on what happened the last time you told someone to calm down - I'm guessing the opposite happened? 
I often deal with difficult emotions on coaching calls - even leaders in the C-Suite or C-minus suite sometimes feel impostor syndrome, struggle to step into boisterous team debates, or feel like they don't belong or don't have anything worth hearing at networking events. And telling them NOT to feel those emotions and to do something different is not an effective way to change their outcomes. While I'm not a therapist, I sometimes have to create a therapeutic experience for my clients, based on what I understand is best practice, to create a space to process those emotions.
Accepting that they feel their feelings is an essential first step. Feeling these difficult feelings fully can help you metabolize them…and for certain, avoiding feeling our feelings doesn't make them go away, it just stuffs them down - metastasizes them, more than metabolizes them.
But feeling our feelings is only one step towards fully metabolizing them into something useful. Eventually, we have to learn to calm those feelings when they return - which they very well might.
We can calm those feelings through meditation, journaling, and breathing, but we can also calm those feelings by stepping outside of ourselves and focusing on others instead. Charlie suggests a healthy coping mechanism for our anxieties, which is not to pretend that we don't experience them but to think more about what another person needs to hear than what we feel - we could call it the "get out of my head and get into their head" approach - in this case, focusing on an investor's desire to, as Charlie describes it, buy a "ticket to a very large outcome" and focus on how to craft our messaging towards that goal.
And we dive into a very worthwhile and very likely conversation founders will face - how to strategically design the conversation after a startup failure, where Charlie argues that avoiding investors and ghosting them is an (understandable) mistake, but one that surrenders control of your narrative. Instead, Charlie shares how to lean into hard conversations with some clear 2 X 2 thinking!
This episode is jam-packed with actionable advice for navigating the complexities of raising and running an impactful company.
Links
https://www.thisisgoingtobebig.com/
What's next after you lose someone's money? https://www.thisisgoingtobebig.com/blog/2025/11/29/whats-next-after-you-lose-someones-money
https://www.brooklynbridge.vc/team
Want to get Great at something? Get a Coach: The TED talk from Surgeon Atul Gawande https://www.youtube.com/watch?v=oHDq1PcYkT4
New Yorker article behind the TED talk https://www.newyorker.com/magazine/2011/10/03/personal-best
Humble Inquiry by Edgar Shein https://amorebeautifulquestion.com/humble-inquiry-the-best-kind/

Get free chapters of my book, Good Talk, and master the art of conversations big and small: https://www.danielstillman.com/good-talk
Please support the podcast!
💌 subscribe on Spotify: https://spoti.fi/3QzcPAW
💌 iTunes: https://apple.co/4ifh6pb
or with a monthly contribution here: https://bit.ly/support-tcf-monthly
one-time donation here: https://bit.ly/support-tcf-once
Check out https://theconversationfactory.com/podcast/the-power-of-nature-to-fuel-creativity-with-warren-berger for the full transcript and video highlights.
Warren Berger, a bestselling author and "Questionologist," advocates for reconnecting with deep, purposeful questioning by taking our most important questions into nature—specifically, a 2-hour walk in the woods followed by 3 hours of focused work. He argues that in the digital age, our creativity is being eroded by constant connectivity and AI-generated "good-enough" answers, which prevent us from wrestling with truly meaningful problems. Drawing on Henry David Thoreau's philosophy, Berger promotes this practice as a way to reclaim breakthrough thinking and move beyond surface-level solutions.
Beyond the woods-and-work framework, Berger emphasizes the craft of questioning itself—encouraging people to root their questions in deep empathy, design them for maximum impact, and sequence them thoughtfully within conversations. His "Question sandwich" approach demonstrates how context and framing shape how questions land with others, ultimately enabling more powerful and authentic dialogue.
Key Moments
00:00 Exploring Creativity and Nature 
07:32 The Role of Questions in Organizations 
11:23 The Power of Collaborative Inquiry 
18:54 Designing Beautiful Questions 
23:21 Empathy in Questioning 
24:50 The Outside-In Method for Creativity 
28:22 Nature's Impact on Creative Thinking 
30:30 Balancing Structure and Flexibility in Creativity 
34:15 The Commitment to Creativity 
39:31 The Role of Companionship in Focus 
42:57 Defining Creativity and Its Broad Applications
Links
Here's a recent NYT article from Warren talking about his experiences with nature's effects on creativity - specifically, an area in Ireland called the Burren. https://archive.ph/tgnrG
You can find more information about the Burren Creativity Experiment here. https://www.burrencreativityjournal.com/creative-experiment
Here's a NYT article talking about my cousin's company, Caveday, that we mentioned. https://archive.ph/sC7pX

Marcy Syms is a pioneering businesswoman and advocate for respect in leadership.
She's seen leadership fads come and go.
She was a CEO when people still thought "women shouldn't do that sort of thing" 
And she's done something many folks have never had to endure - shuttering her family's business while making her key creditors whole - an act deeply in line with her core value of respect.
Marcy shares insights from her journey in the retail industry, her experiences with leadership dynamics  and her advocacy for the Equal Rights Amendment - something she hopes to see made part of the constitution while she's still around to enjoy it!
Why Respect?
🗝️Respect drives sustainable growth - respect for your team allows them to feel empowered to be the face of your business and to build the processes and systems that make growth sustainable.
🗝️Giving respect helps you get respect - starting first, leading the conversation with respect at the core helps get things done, especially in times of stress and turbulence.
🗝️Respect is outer behavior and inner work - to make it a core habit and your default behavior takes strategic reflection and personal growth.
Check out the full conversation 👇
🎙️ Spotify: https://spoti.fi/3QzcPAW 
🍎 Apple: https://apple.co/4ifh6pb 
📺YouTube: https://www.youtube.com/@danielstillman-TCF-podcast
🌐more episodes at https://theconversationfactory.com/listen
And please subscribe on Spotify or iTunes!
Also! support the podcast with 
a monthly contribution here: https://theconversationfactory.com/conversation-factory-insider
or a one-time donation here.: https://dastillman.gumroad.com/l/dscoffee
Don't have time to watch or listen to the full episode? To learn more about leading conversations more powerfully and beautifully, watch these short clips 👇
👀make respect a habit and start from within
https://youtu.be/tmURMgvcnIs
👀How to Respond to Disrespect with Dignity and Strategy
https://youtu.be/f21aAalKGLU
👀To Scale you need to Respect your team
https://youtube.com/shorts/HczFY9-ASFw
👀Leadership Balances Top Down Strategy and Bottom up Insights
https://youtube.com/shorts/57yWfiQtykw
👀Know your board as humans
https://youtu.be/eH5Mv95iunE
One Takeaway to not forget: Fight for the ERA! Marcy shares how she sees the ERA as the ultimate sign of respect and continues to fight for women's full inclusion in the constitution. Watch here: https://youtu.be/YAbEAqIVxzU
Key Links:
Marcy's book: Leading with the Respect
Marcy's website

Download free chapters from Good Talk and master the art of conversations big and small: https://www.danielstillman.com/good-talk
Listen now 👇
🎙️ Spotify: https://spoti.fi/3QzcPAW
🍎 Apple: https://apple.co/4ifh6pb 
And please subscribe on Spotify or iTunes! 
Also! support the podcast with 
a monthly contribution here: https://theconversationfactory.com/conversation-factory-insider
or a one-time donation here: https://dastillman.gumroad.com/l/dscoffee
Full show notes: https://theconversationfactory.com/listen
 
SUMMARY
In this conversation, Adam Kahane discusses the complexities of transforming systems, emphasizing the importance of understanding systems thinking, collaboration, and the role of individual contributions. He shares insights from urban transformation examples, the significance of culture, and the necessity of engaging with systems responsibly. Kahane introduces seven habits for transforming systems, highlighting the importance of finding cracks as opportunities for change and the balance between closeness and distance in understanding systems.
 
KEY TAKEAWAYS
Systems can't be transformed without understanding them.
Transformation requires many people to do many things.
You can't just change a system by force.
Look for what's unseen in a system.
Forget your perfect offering; there's a crack in everything.
Acting responsibly is crucial for transformation.
We all have bells we still can ring.
Engaging with the system is a collective activity.
You can make wiser decisions by understanding others.
Change how you think, change how you are.
 
CHAPTERS
00:00 Understanding Systems for Transformation
02:29 The Role of Collaboration in System Change
05:05 Insights from Global Examples
07:46 The Importance of Proximity in System Change
10:10 Cracks and Leverage Points in Systems
12:46 The Journey of Transformation in South Africa
24:31 The Journey of Collective Engagement
24:55 Radical Engagement: Understanding System Transformation
26:13 The Role of Outsiders vs. Insiders
27:41 Spotting Cracks: Micro Interactions in Systems
28:46 The Art of Persuasion vs. Convincing
30:29 Granular Habits for System Transformation
31:41 Relating in Three Dimensions
33:43 Understanding the Seven Habits
39:32 Acting Responsibly in Systems
43:21 Finding Light in the Cracks
 
LINKS
Learn more about Adam's work at www.reospartners.com , www.reospartners.com/adamkahane and find him on twitter/X at @adamkahane

Get free chapters of my book, Good Talk, and master the art of conversations big and small: https://www.danielstillman.com/good-talk
Please support the podcast!
💌 subscribe on Spotify: https://spoti.fi/3QzcPAW
💌 iTunes: https://apple.co/4ifh6pb
or with a monthly contribution here: https://bit.ly/support-tcf-monthly
one-time donation here: https://bit.ly/support-tcf-once
Check out the episode page for the full transcript and video highlights.
Episode page: https://theconversationfactory.com/podcast/innovation-connection-and-conscious-leadership-with-othership-ceo-robbie-bent
AI Summary:
Introduction and Connection: Daniel Stillman introduces Robbie Bent, highlighting the connection through mutual acquaintance Robbie Hammond.
Inception of OtherShip: Robbie shares the story of starting with a backyard ice bath, fostering community connections without the influence of alcohol.
Innovative Experiences: Discussion on unique offerings at OtherShip, such as comedy nights and men's work sessions, blending wellness with entertainment.
Creativity and Experimentation: Robbie emphasizes the importance of allowing creativity to emerge through testing and iteration.
Challenges and Growth: Insights into the challenges faced in expanding OtherShip, including managing stress and maintaining personal well-being.
Community and Relationships: The role of community in personal and business growth, with Robbie working closely with his wife and friends.
Facilitating Conversations: The significance of open communication and addressing conflicts early in both personal and professional settings.
Future Aspirations: Robbie's excitement about expanding OtherShip and continuing to innovate in the wellness space.
Links
Othership - https://www.othership.us/
Follow Robbie Bent on Instagram | LinkedIn
IG: https://www.instagram.com/robbiebent/?hl=en
LI: https://www.linkedin.com/in/robbiebent/