The Conversation Factory

Daniel Stillman
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Feb 13, 2023 • 1h 5min

Launching a Remote, Asynchronous Venture Studio

Today I sit down with my friend 
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Dec 15, 2022 • 50min

Conscious Collaboration: Co-founder Conversations

In this conversation, I sat down with Beth Bayouth and Mario Fedelin, the COO and CEO (respectively) of Changeist, a non-profit organization dedicated to youth empowerment. They are building a community of young people that utilize their personal agency to create a more just society.  Changeist’s programs help 11-26 year olds learn a common civic language, engage in dialogue, and build community to investigate local and global social justice issues. Participants also work with other local community-based organizations to implement local solutions to local problems. Together, Mario and Beth explore how they met, built a relationship and decided to work on this project together…and how they continue to manage themselves and each other in the entrepreneurship journey.  A few insights we’ll unpack about conscious co-founder relationships: The key to a great co-founder relationship is that both of you do not fall apart at the same time! Fighting Well and how Cofounder Intimacy can help: With cofounder intimacy, there is an understanding that often there’s something else behind a conflict or a mood. Because when you're close, you tend to know about what’s going on or that it’s safe to ask. Knowing yourself and your skills The Power of working with someone with a Different Skill Set but Similar Values  On Knowing yourself and your skills, and finding compliments on your core team:  A great leadership team requires Comfort with yourself and your skills and Respect for the skills of others... and it takes Balance - but Balance of what?! On a leadership team you need: + Architects and Visionaries + Multipliers - someone who brings something you do not have to the table, who is also committed to the vision and the journey Another way to think about this is that you need: + A Balance of Openers and Closers on the team. This is the essence of conscious collaboration - knowing if you are more comfortable in a generative or divergent mode, ie, opening, or are more natural in the “Synthesizer” role - organizing, closing, or planning towards action. Mario owns his limitations as a “closer” and intentionally chose Beth as a COO for her natural “shark” skills - her ability to move things forward with clarity. Mario and Beth also talked about their balanced styles in “Speeding up”  and “Slowing Down” creative conversations - Beth will pump the brakes and ground ideas in reality when the time is right. Feeling that balance between creativity and clarity, speed and thoughtfully slowing things down, is the essence of conscious creativity and conscious collaboration…being comfortable with both opening and closing modes is critical, but collaborating with others who complement your natural approaches is powerful. Be sure to check out my other co-founder conversations. I discussed building an Integrity Culture with the co-founders of Huddle, Michale Saloio and Stephanie Golik, and investigated prototyping partnerships with Jane Portman and Benedikt Deicke, co-founders of Userlist. (Which Mario and Beth absolutely did, as well!)  I also sat down with Jennifer Dennard and Dan Pupius, the co-founders of Range to unpack Healthy Conflict in Cofounder relationships. Conflict and collisions will inevitably happen in relationships, so you might as well learn to lean into it! You may also enjoy my interview with Carolyn Gregoire and Scott Barry Kaufman, the co-authors of the 2015 bestseller, Wired to Create, where we unpack how they managed their working relationship and discuss Paired creativity, which is totally a thing! And if you really want to dive deep into the idea of being a conscious co-founder, make sure to check out my conversation with my friend Doug Erwin, the Senior Vice President of Entrepreneurial Development at EDAWN, the Economic Development Authority of Western Nevada. Head over to theconversationfactory.com/listen for full episode transcripts, links, show notes and more key quotes and ideas. You can also head over there and become a monthly supporter of the show for as little as $8 a month. You'll get complimentary access to exclusive workshops and resources that I only share with this circle of facilitators and leaders. Links Changeist On Healthy Conflict: https://theconversationfactory.com/podcast/managing-healthy-conflict-co-founder-conversations
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4 snips
Nov 10, 2022 • 48min

Managing Healthy Conflict: Co-founder Conversations

In this conversation I talk with Jennifer Dennard and Dan Pupius, the co-founders of Range, software that helps teams be more connected, focused, and productive no matter where they’re working. Global teams at Twitter, New Relic, CircleCI, and more keep their teams in sync and connected with Range. Jen is the co-founder and COO. Prior to founding Range, Jen led Medium’s organizational development team. Jen has partnered and consulted with startups and multinational corporations on empowering autonomous and distributed teamwork. She lives in Colorado with her two cats and husband. Dan is co-founder and CEO of Range. Prior to Range, Dan was Head of Engineering at the publishing platform Medium. And before that he was a Staff Software engineer at Google, where he worked on Gmail, Google+, and a variety of frontend infrastructure. He has an MA in Industrial Design from Sheffield Hallam University and a BSc in Artificial Intelligence from the University of Manchester. In past lives he raced snowboards, jumped out of planes, and lived in the jungle. This is a fairly meta conversation (in the old sense of the word!) since we talked about how Dan and Jen structure their relationship and how they built their company…which is a company that builds software that structures relationships - specifically, effective teams. As Dan outlines, “Human behavior requires structure to facilitate it…in an organization, software provides a lot of architecture, which shapes our behavior, but we're (often) not intentional about that software. The whole theory of Range was… how can we build software that acts as architecture that shapes the behaviors that we believe to be present in effective teams?” My book Good Talk is built around the idea of a Conversation OS, or Operating System.  One element of the Conversation Operating System is error and repair. As Jen says in the opening quote, conflict and collisions will inevitably happen in relationships. Dan suggests that “if you have productive conflict or if you encourage productive conflict, there will be times when you step over the boundary and it's what you do then that is the important thing, in how you recover.” In other words, how you repair the error or breach in the relationship is often more important than the error itself. Many folks shy away from conflict, or hope it never happens. Planning for it and knowing it will happen is a fundamentally different stance, a more effective Error and Repair Operating System. I also love the “reasonable person principle” that Jen and Dan use in their relationship, as long as it never slides into gaslighting. We unpack a lot more great stuff, from uninstalling Holacracy at Medium to the importance of being journey-focused in entrepreneurship relationships, and the power of crafting explicit processes ahead of needing to use them. Dan and Jen are also big believers, like me, in the power of the “check-in''. For example, in my men’s group we share in 30 seconds how we're doing emotionally and physically at the start of every group. At Range, it can be as simple as a “green, yellow, red” check-in or as deep as going straight to the question “how are you…really?”  They suggest that baking human connection into each and every meeting is much much more effective than trying to isolate connection into one “vibes” meeting. As with many of my co-founder conversations, there is a common thread of clear roles along with an awareness of and respect for the Venn diagram of skills between the co-founders. Another common thread, as Dan says at the end of our conversation: looking after yourself and attending to yourself is key, because “if you're not in a good state, you can't be a good teammate and you definitely can't be a good leader.” Be sure to check out my other co-founder conversations. I discussed building an Integrity Culture with the co-founders of Huddle, Michale Saloio and Stephanie Golik, and investigated prototyping partnerships with Jane Portman and Benedikt Deicke, co-founders of Userlist.  You may also enjoy my interview with Carolyn Gregoire and Scott Barry Kaufman, the co-authors of the 2015 bestseller, Wired to Create, where we unpack how they managed their working relationship. Paired creativity is a thing! And if you really want to dive deep into the idea of being a conscious co-founder, make sure to check out my conversation with my friend Doug Erwin, the Senior Vice President of Entrepreneurial Development at EDAWN, the Economic Development Authority of Western Nevada. Head over to theconversationfactory.com/listen for full episode transcripts, links, show notes and more key quotes and ideas. You can also head over there and become a monthly supporter of the show for as little as $8 a month. You'll get complimentary access to exclusive workshops and resources that I only share with this circle of facilitators and leaders. Links Range Lawrence Lessig’s Pathetic Dot theory Daniel Coyle’s Belonging Cues: Belonging cues are non-verbal signals that humans use to create safe connections in groups. The three basic qualities of belonging cues are 1) the energy invested in the exchange, 2) valuing individuals, and 3) signaling that the relationship will sustain in the future. Kegan’s Levels, specifically, Stage 4 — Self-Authoring mind Lead Time Chats
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Oct 25, 2022 • 54min

Building an Integrity Culture: Co-Founder Conversations

In this conversation, I sit down with Huddle Co-Founders Stephanie Golik and Michael Saloio. Huddle is a platform for designers and builders to invest in startups with their time.  Stephanie has spent her career building alongside founders at studios and leading design and product at fast-growing tech companies. She was an early design leader at Cruise, building user experiences for self-driving cars. Before that, Steph was Head of Product at Mapfit (acq. by Foursquare). She's a proud Cuban-American born, raised and currently residing in Miami. Michael is a product and team-focused entrepreneur and investor. He’s spent his career working with technology executives and investors. As an investment analyst at Oppenheimer & Co., he followed some of the biggest names in technology including Cisco, EMC, and Apple. Prior to Oppenheimer, Mike covered special situations at Sidoti & Co. Over the past five years, Michael reimagined his career to focus on early-stage businesses. He was the first employee at SuperPhone, a messaging application backed by Ben Horowitz, Betaworks, Bessemer, and more. Since 2014 he has consulted with, invested in, or advised more than 35 startups that have raised more than $200M in venture financing. I met Michael years ago and have tracked his rise…when I saw that his latest venture raised 3.3M and was a co-founded company, I reconnected to include him in my co-founder conversations series. My question throughout this series has been simple - what does it take to build and sustain a powerful co-founder relationship?  Michael and Stephanie shared some of the insights and principles that helped them do exactly that. The biggest aha was the umbrella concept of an Integrity Culture, and how many powerful values fall into place with a focus on Integrity. As Michael points out, it’s not just “I do what I say I will” it's also about a culture of Coaching and Feedback to help everyone right-size their commitments and to give themselves (and others) feedback along the way when they find themselves falling short. Stephanie and Michael share a conversation format that they use over the course of each week to keep their team on track and in integrity! Integrity Culture also implicates one of my favorite words: Interoception, a concept I learned from Food Coach Alissa Rumsey. Michael and Stephanie’s vision of an integrity culture is one where you commit to a thing because you are intrinsically motivated to do it, not through force or pressure…you self-select the thing you are going to do. And that means you know what you want! Interoception is the ability to feel and know your inner state.  Some additional keys to a powerful co-founder relationship that line up with the other conversations in this series are the ability to have Healthy Conflict (rather than an unhealthy “peace”) and the regular asking and giving of generous and generative deep feedback. One other insight that was fresh for me in this conversation was Michael’s idea of a good co-founder relationship as one that is “Energy Producing” vs. energy sucking. A powerful co-founder relationship is like a flywheel - the more energy you invest into it, the more energy it throws off. Be sure to check out my other co-founder conversations, like this episode with Jane Portman and Benedikt Deicke, co-founders of Userlist, on how they connected through shared communities and learned how each other really worked through real-world, previous projects. You may also enjoy my interview with Carolyn Gregoire and Scott Barry Kaufman, the co-authors of the 2015 bestseller, Wired to Create, where we unpack how they managed their working relationship. And if you really want to dive deep into the idea of being a conscious co-founder, make sure to check out my conversation with my friend Doug Erwin, the Senior Vice President of Entrepreneurial Development at EDAWN, the Economic Development Authority of Western Nevada. Head over to theconversationfactory.com/listen for full episode transcripts, links, show notes  and more key quotes and ideas. You can also head over there and become a monthly supporter of the show for as little as $8 a month. You'll get complimentary access to exclusive workshops and resources that I only share with this circle of facilitators and leaders. Links Huddle website
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Sep 20, 2022 • 50min

Community Building for Founders through Conversation and Hosting

Today my guest is Yehong Zhu, the founder and CEO of Zette. We discuss three key layers of conversation design:  + The conversation with yourself - even with so many companies founded…why not me? + The importance of community, community building and hosting as an integral part of staying sane, informed and productive as a founder. + The broader, cultural conversation - how does a founder design the conversation around why does this company matter? Shaping this narrative arc can help you connect your company’s mission to the mission of potential funders and advisors Prior to starting Zette, she worked as a journalist at Forbes Magazine, where she reported on business, market and technology trends. She also worked as a product manager at Twitter on two consumer teams—the Tweets team in San Francisco and the Events team in London—where she shipped features on desktop, mobile web, iOS, and Android to 330M users globally. She graduated from Harvard College in 2018 with a degree in philosophy and government. Be sure to check out my conversation with Michael Bervell about his “Conversation Onion” model that we reference in the conversation. Head over to theconversationfactory.com/listen for full episode transcripts, links, show notes  and more key quotes and ideas. You can also head over there and become a monthly supporter of the show for as little as $8 a month. You'll get complimentary access to exclusive workshops and resources that I only share with this circle of facilitators and leaders. Links Playing Nice with Paywalls Zette
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Aug 22, 2022 • 59min

Clarity and Intimacy in Co-Founder Conversations

In this conversation, I dive into the nuances of co-founder relationships with Clarity.so co-founders Richie Bonilla, CEO and Eni Jaupi, CTO. Clarity.so is a y-combinator funded startup that has built a groundbreaking DAO contribution platform. DAO stands for Decentralized, Autonomous Organization, which you should totally google if you want to know more.  While Clarity isn’t a DAO, you can see how the radical transparency that is at the heart and spirit of the cryptocurrency movement is also at the core of Richie and Eni’s relationship. I mean, it’s also the name of the company! Like a few of the other conscious co-founder interviews I’ve been doing, these two co-founders prototyped their working relationship before jumping into their company together, which helped them build a foundation of trust and respect. They also talked a lot. Like A LOT before even starting the company. Starting with a few times a week, they gradually transitioned to talking for at least an hour, daily, for a year. What this conversation re-established for me was that it’s important to have agenda-ed conversations, and it’s also very important to have stream-of-consciousness, unagendaed conversations, too. Generally speaking, we’re great at structure, and less good at making space for wondering and wandering. For more on the power of wondering and wandering, make sure to check out my interview with Natalie Nixon. Be sure to check out my conversation with Jane Portman and Benedikt Deicke, co-founders of Userlist, on how they connected through shared communities and learned how each other really worked through real-world, previous projects. You may also enjoy my interview with Carolyn Gregoire and Scott Barry Kaufman, the co-authors of the 2015 bestseller, Wired to Create, where we unpack how they managed their working relationship. And if you really want to dive deep into the idea of being a conscious co-founder, make sure to check out my conversation with my friend Doug Erwin, the Senior Vice President of Entrepreneurial Development at EDAWN, the Economic Development Authority of Western Nevada. Head over to theconversationfactory.com/listen for full episode transcripts, links, show notes  and more key quotes and ideas. You can also head over there and become a monthly supporter of the show for as little as $8 a month. You'll get complimentary access to exclusive workshops and resources that I only share with this circle of facilitators and leaders. Links Clarity.so
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Jul 25, 2022 • 50min

Conscious Co-founders

In this conversation, I sat down with my friend Doug Erwin, the Senior Vice President of Entrepreneurial Development at EDAWN, the Economic Development Authority of Western Nevada. Doug is a former serial entrepreneur turned economic developer and executive coach, and he’s committed to growing Northern Nevada’s startup and technology ecosystem. His community work has helped change the perception of Reno and lay the foundation for future generations of entrepreneurs to thrive in the region. Doug is proud to support entrepreneurs as they embark upon their own journeys.    Doug shares, with great clarity, vulnerability and humility, his entrepreneurial journey and some key lessons he’s learned along the way. I invited Doug to have a conversation with me about what it might mean to be a conscious cofounder, given Doug’s personal work on mindfulness. Towards the end of the conversation, we arrive at the idea that we are our own most important cofounder - the conversations we have with ourselves will either lead us to lean into or turn away from challenging conversations with our cofounders. And with the lens of Triple Loop Learning, we can start to create better cofounder relationships, not just with better contracts and financial structures, but from our way of being. The basic metaphor is this: Work is a relationship. And relationships are made of conversations. And you can hear this in Doug's description of a company as a “rebound startup” or talking about startups like a marriage. And just like in personal relationships, sometimes, as Doug says, people want to turn away from the discomfort of having difficult conversations. Doug mentioned research about splits among founders and how it related to the future success of the company. I did a bit of digging and... It’s counter-intuitive, that a startup with equal distributions is a red flag to investors, and that such a company is more likely to fail. Doug suggests that unequal distributions are proof that the founders have had some hard conversations - which is a key skill in work and life. However, roughly three out of four startups decide to split the business equally when they start up. One of the main issues with this approach isn’t a question of HOW to make the split, but WHEN. A 2016 HBR article suggests that founders should wait to split shares until later, co-creating rules to determine the value of various contributions. (I recommend the book Slicing the Pie!). The HBR authors suggest that “teams that negotiate longer are more likely to decide on an unequal split: the harder you look, the more likely you are to discover important differences. More generally, [they] argue that if cofounders haven’t learned something surprising about each other from their dialogue, they probably haven’t engaged in a serious enough discussion yet.” The HBR article suggests that a hastily created equal split will sour over time - the percentage of founders who are unhappy with their split increases by 2.5x as their startups mature. That discontent can lead to rapid turnover, which can be problematic. Another study, led by Professor David Noack, Executive Director of the Hall Global Entrepreneurship Center at the Goddard School of Business and Economics at Utah’s Weber State University suggests that an equal split, especially in early-stage companies, has another unexpected effect - making it unclear who’s driving the bus. According to Professor Noack’s research, if no one feels that they have ownership and responsibility, no one takes the wheel, which has a real effect:  Companies with an unequal split were 21.7% more likely than other firms to be up and running a year later. And just like in a marriage, having a “pre-nup” conversation can be awkward, even when people know the data about divorce.  While it’s uncomfortable to do so, hosting a conversation to explore all the negative scenarios that might occur in the future, with corresponding actions to help avoid them, can help founders avoid headaches later on…and increase startups’ chances of success. This is a conversation worth listening to…And I’m excited to share it with you! Head over to theconversationfactory.com/listen for full episode transcripts, links, show notes, and more key quotes and ideas. You can also head over there and become a monthly supporter of the show for as little as $8 a month. You'll get complimentary access to exclusive workshops and resources that I only share with this circle of facilitators and leaders. Links EDAWN - Startup Reno Growth Pioneers Podcast
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Jul 17, 2022 • 55min

Stories as Medicine

I first met Dr. Paul Browde as part of a multi-month intensive men's work program we were both part of. We were just about to break out into a few parallel sessions about various elements of running men’s groups when Paul raised his hand and said something to the effect of “would it be useful to have a breakout session about our personal narratives and how we use them to lead?” I watched as the heads of 40+ men swiveled to focus on this one unassuming gentleman and witnessed nearly half of the group switch over from whatever session they were planning on going to and instead, go to sit around Paul to listen to him tell his story and share his wisdom about how to share our own stories. That’s the power of story! Paul is a doctor of psychiatry and a TedX speaker. He has shared the stage with luminaries like Esther Perel, has taught Narrative Medicine at Columbia University, and co-founded a storytelling company called Narativ. Paul has some profound wisdom to share about how to become aware of a different type of story - the stories that tell us, as well as the power of sharing our own stories, and examining the stories we tell about ourselves to ourselves and to others.  As Paul writes on his site: We are born in connection, we are wired for connection, and it is through connection that we heal and experience our true aliveness. I have always felt that stories can be the most powerful elements of communication - indeed, they are the thread that holds together each and every conversation.  Stories are how we connect, heal and come alive. Listen onward to learn about Paul’s mental models of how to become a space for others to share their stories - to shape your listening as a vessel, a bowl, to receive stories generously. Narrative is powerful medicine that we can give to ourselves and to the people around us. Enjoy this conversation as much as I did! Head over to theconversationfactory.com/listen for full episode transcripts, links, show notes and more key quotes and ideas. You can also head over there and become a monthly supporter of the show for as little as $8 a month. You'll get complimentary access to exclusive workshops and resources that I only share with this circle of facilitators and leaders. Links Paul Browde: Healing through connection The Power of Two: How Listening Shapes Storytelling Two Twosomes, Not a Script in Sight The Masculinity Paradox: Warmup with Paul Browde - Sessions Live by Ester Perel
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Jun 20, 2022 • 50min

Prototyping Partnerships

How do you make a friend? How do you become lovers with someone? How do you become business partners? In RomComs, there’s a “meet-cute”...the hilarious and unlikely way two people in this topsy-turvy mixed-up world collide and fall madly, rapidly in love.  In the real world, taking time and gradually testing, trying and yes, prototyping a relationship is ideal. In love, we call it dating. There’s no good word for “friend-dating”, especially when you’re doing it with someone of the same sex.  And with founding a company…where does the conversation start? In this conversation, I sit down with Jane Portman and Benedikt Deicke, co-founders of Userlist, on how they connected through shared communities, and learned how each other really worked through real-world, previous projects. They also share their insights on setting the stage for both a long-term vision for building a company AND for a possible exit from a partnership through thoughtful conversations. Userlist is a tool for sending behavior-based messages to SaaS customers and recently completed a pre-seed round with 21 angel inventors. Benedikt is a software engineer from Germany who loves to plan, build, and grow web applications. He co-hosts the Slow And Steady Podcast and organizes the Femto Conference, a tiny conference for self-funded tech companies. Jane is a leading UI/UX consultant specializing in web application design, and has been the host and founder of the  UI Breakfast podcast since 2014 (she kindly invited me to join her show in early 2022). Enjoy my conversation with these two delightful co-founders as much as I did. Head over to theconversationfactory.com/listen for full episode transcripts, links, show notes, and more key quotes and ideas. You can also head over there and become a monthly supporter of the show for as little as $8 a month. You'll get complimentary access to exclusive workshops and resources that I only share with this circle of facilitators and leaders. Links UI Breakfast Userlist benediktdeicke.com Better Done than Perfect podcast  Jane's Story: Turning Thirty: Story of My Life Culture, Values, Operating Principles & More Inspire, Not Instruct: How We Do User Onboarding at Userlist
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May 30, 2022 • 51min

Wired to Create Together

Today I host a conversation with Carolyn Gregoire and Scott Barry Kaufman, the co-authors of the 2015 bestseller, Wired to Create. Their working title was “Messy Minds” and one of the core ideas of the book is just that - deeply creative folks can manage messiness, plow through paradox and move calmly through contradiction. These capacities are also powerful tools for managing a creative relationship. I’m doing a series of interviews with co-founders on how they design their conversations (ie, their broader relationship) and manage themselves and each other while building and running a company.  A book is a mini-company, and so when I met Carolyn through a friend, I thought she and Scott would be amazing folks to unpack how a high tolerance for dissonance, complexity, ambiguity, and chaos can help us make amazing things, together. Creativity, making something new, isn’t ever a clear linear progression towards the dream, the magical ideal goal. There’s always iteration, recursion, re-invention…and being patient with the process, your creative partner and yourself - that last one is a truly powerful key. One of my favorite insights was the idea of the importance of sensitivity and awareness of your own inner state and the willingness to take downtime…both to manage yourself, refuel and to trust that stepping back will always help - since constant production isn’t possible! One thing you’ll hear over and over again is the complementarity and flow in a positive creative relationship: being able to feed back and forth between each other and also give and take, grounded in respect and admiration for each other's skills and contributions. This respect for the other’s skills allows for a dramatic increase in output through parallel work, or relay-race style collaboration. Make sure to check out Carolyn’s other writing and book doula work at carolyngregoire.com and Scott’s podcast, course, and his recent best-selling book, Transcend, at scottbarrykaufman.com. Head over to theconversationfactory.com/listen for full episode transcripts, links, show notes  and more key quotes and ideas. You can also head over there and become a monthly supporter of the show for as little as $8 a month. You'll get complimentary access to exclusive workshops and resources that I only share with this circle of facilitators and leaders. Links Carolyn Gregoire's website Scott Barry Kaufman's website Wired to Create, by Scott Barry Kaufman and Carolyn Gregoire Trust the Process, by Shaun McNiff The Messy Middle, by Scott Belsky Origami: From Angelfish to Zen

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