Today, I sit down for a conversation with *my coach* Robert Ellis, about his new book, Coaching From Essence. Robert has been described as “one of Silicon Valley’s best-kept secrets” and has been coaching leaders at startups, mid-stage companies, Fortune 500 giants, and nonprofits for over 30 years. Robert has taught leadership and coached entrepreneurs at Singularity University and developed Level UP, the leadership curriculum for the Global Startup Program, and taught leadership courses at Stanford University. We met through radical serendipity and I’m grateful for the generosity and grace Robert has coached me with. All of his teaching materials are now publicly available on his free circle community and on youtube. Robert’s book is like sitting in a fireside chat with Robert, absorbing his profoundly wise and profoundly simple approaches to coaching. Sometimes, a new idea can feel so true that it lands like common sense - all the pieces fitting together so seamlessly and effortlessly. Roberts’ metaphors, stories and models hit like that - like powerful truths you knew all along. Robert’s visual models help ground a coaching conversation, make it easy to follow along, and make the conversation incredibly sticky. And literally every time I’ve drawn one of these diagrams for a client, it lands with them and becomes a new metaphor for thinking about their challenge and their path forward. This book isn’t just for coaches who want a more effortless and human approach to doing this work, it’s for anyone who wants to be deeply helpful to their clients, their teams, their organization, and to lead conversations in a more impactful way. Coaching from Essence is based on the radical idea that everyone has an essence, and that, when we work from it, we can effortlessly create value and impact. Coaching from essence works both ways - the coach coaches from *their* essence, their natural approach…and the coachee is coached to work from their *own* essence - their own natural approach. We’re not telling people how to be. We are here to help them remove the obstacles that get in the way of them finding their own way. According to Bill Gates, everyone needs a coach.  I would flip this suggestion on its head and say that at some point in everyone’s lives, accessing a Coaching from Essence mindset can be a generous, powerful and transformative way to help someone in our lives. Some of us choose to make coaching our life's work, but Coaching from Essence is a powerful, generous and transformative approach to helping people that everyone can (and should?) access at the right moment for the right person.  Robert Ellis is the embodiment of what he teaches - he is a generous, powerful and transformative coach who I’ve had the pleasure of working under for several years. I’m so glad this book is finally out in the world so that everyone can have the experience of working with him. Links https://coachingfromessence.com/ https://www.futurosity.com/ Coaching from Essence, by Robert Ellis

I first met Avantika Daing, a General Partner & Managing Partner at Plum Alley Investments (and Tedx Speaker!) while she was onstage at an Entrepreneurs Roundtable Accelerator event. She was there to share a bit about Plum Alley’s Investment thesis as well as unpack six pitches live from early-stage companies. Let’s level set a bit so you understand Avantika’s and Plum Alley’s mission, which revolves around an important number that hasn’t moved much in years, despite a lot of effort - 2%.  According to Pitchbook, in 2022, companies founded solely by women garnered just 2% of the total capital invested in VC-backed startups in the United States. Plum Alley only funds gender-diverse companies and works to create an ecosystem to help them not just get funded, but to grow and succeed. That’s one of the reasons I wanted to bring Avantika on, to share some of her ways of thinking strategically about funding as an investor, how Plum Alley is working to create a more sustainable funding ecosystem for diverse founding teams, and how she coaches founders to be more strategic about funding, too. Watching Avantika on stage peel back the layers of the onion (one of her favorite metaphors!) on a company’s story in conversation with a founder and work to understand the company’s potential was fascinating - it’s a tremendous act of intellectual rigor and curiosity. Her questions also reminded me that founders can make an investor’s job a lot easier through more powerful and intentional storytelling. Another powerful metaphor that Avantika came back to in a number of pitches was the idea of a Basecamp. In other words, Avantika, as a funder, wants to know: Is your company building a core technology or defensible market position (a basecamp) that will provide you with multiple paths to success?  Avantika acknowledged that a “single story” about how your company will “win” or “summit the mountain” is powerful, but she was clear that she prefers companies that are creating a powerful “basecamp”...why? Because: 🏒A “many shots on goal” strategy can help create longevity and increase options for success. I’m so grateful that she was willing to have a longer conversation with me on the record to explain her ideals about storytelling and the basecamp-summit metaphor. She also helped peel back some layers on another idea she loves to coach founders on: “Dressing their cap table” for sustainable success from seed to IPO and well beyond - since capital needs don’t stop at IPO. I love how Avantika’s metaphors shift,  refocus and redesign the conversation about pitching, funding and sustainable success for startups. 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 Plum Alley Avantika's Tedx Talk: There is No Balance. There is Juggling Daniel’s LI post on Avantika’s Entrepreur’s Roundtable Session, highlighting key questions and perspectives from Avantika, including the “base camp/summit” metaphor.

Today my conversation partner is Matt LeMay! Matt is an internationally recognized product leader, author, and consultant. He is the author of Agile for Everybody (O’Reilly Media, 2018) and Product Management in Practice (Second Edition O'Reilly Media, 2022), and has helped build and scale product management practices at companies ranging from early-stage startups to Fortune 500 enterprises.  Matt and I met at UX Lisbon last year where he gave a talk that included him describing his extremely actionable recipe for team agility: the One Page / One Hour Pledge, a powerful commitment to minimize busywork and maximize collaboration that has been adopted by individuals and teams at Amazon, Walmart, CNN, and more.  I was excited to bring Matt into a conversation about this pledge, because I know how easy it is to get caught in a rabbit-hole of perfectionism before sharing my work with others. Teams can work more fluidly if we reduce the cycle time between solo work and team work. Matt is an advocate for the power of focus, subtraction and feedback loops over perfection - I mean, would you rather ride a bike you can only aim once or one that you get to steer continuously? I never dreamed I’d get to have a podcast conversation that includes references to Alan Watts and the power of Ego Death to accelerate your team’s success and ultimately, one’s own success…but glad that we are!  Matt and unpack how TIMEBOXING (ie, Tight-and-almost-thoughtless constraints ) helps shift the relationship between thought and action in teams and organizations…and can help move the conversation forward. 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 Matt's website Product Management in Practice https://www.onepageonehour.com/ Matt’s talk at UX Brighton on “You Don’t Get anyone to do Anything” “When we attempt to exercise power or control over someone else, we cannot avoid giving that person the very same power or control over us” Alan Watts Alan Watts “The wisdom of Insecurity

In 2019 My friend Philip invited me to a 2-hour cocktail party at his tiny apartment in the Lower East side. True to his word, the gathering, which was on a Tuesday night, started at 7 PM sharp, and at 9 PM he kicked us out onto Orchard Street to enjoy the rest of our night and/or to get to bed on time (since it was a weeknight, after all!) I met a whole bunch of awesome people, and if I’m honest, I thought Phil was super cool for bringing such a lovely group of people together. The food and drinks were nothing to write home about, but no one cared. Phil stopped the party two or three times to get us to circle up and introduce ourselves and respond to an icebreaker prompt. It was pretty fun. He mentioned during the party that he was following an early draft agenda, a recipe if you will, for such gatherings, that was being developed by his friend Nick Gray, who I knew of through other friends. Nick had started a company called Museum Hack that had blown up - in the good sense. They were leading creative tours in Museums around the city, so I guessed this guy Nick knew a thing or two about getting people together. Cut to 2022 when Nick Gray’s book “The Two Hour Cocktail Party: How to Build Big Relationships with small gatherings” came out. Here it was, four years later! I was fascinated to talk to Nick because I thought “How much could there be to this? Isn’t it all in the title!?” How much could the form have evolved over 4 years of prototyping and testing?!  I’ll tell you folks…this is a polished gem of a book. If you’ve followed my work, you know that I’m a bit of a nerd when it comes to gathering/facilitation/conversation design. I love card decks about it, books, diagrams, narrative metaphors to fuel creative innovation in gathering science for skilled facilitators to bring diverse stakeholders together to tackle wicked problems. I have coached leaders on this skill, all over the world. I hosted many, many cohorts of my 3-month Masterclass on Facilitation that people lovingly described as “drinking from a firehose” of facilitation while somehow being spacious and deeply mindful of how we gather. Managing complex gatherings is a crucial skill! Companies that can’t come together to discuss and decide on actions for their biggest challenges will not survive! And I love these types of gatherings - they are never the same, they have to be absolutely customized, and deeply considered.  Nick, on the other hand, has designed the “CheckList Manifesto”, the “Design Sprint” or the “Joy of Cooking”...not for any and all types of gatherings - but for one, single, Life-changing, surprisingly powerful gathering - a 2-hour, midweek cocktail party. Nick’s book is designed with absolute beginners, or those hesitant or nervous to lead gatherings in mind…but masters of gathering will be pulled in too…I was. Nick designed this insanely in-depth book to cover everything from snacks to drinks to how to write an invitation to…everything. Where to put name tags. How big those tags should be. You get the idea. While I am a nerd in the sense of being an omnivorous gathering nerd, Nick is an obsessive-compulsive nerd of this one form…and for good reason. Nick believes, and I now do, too, that if more people felt more comfortable with having more gatherings we would all be more connected. The midweek 2-hour cocktail party just might save the world. You can get the gist of the form from this conversation (I mean, even from the title!), but if you’re a gathering nerd like me, you'll absolutely enjoy Nick’s insanely thorough guide, which I found myself flipping through regularly as my wife and I prototyped our own first midweek,  2-hour cocktail party, which we titled a “Serendipity Salon”.  I think we all need more serendipity in our lives, and that’s why I loved the opening quote I pulled from my conversation with Nick - the ability to take a short conversation with someone and turn it into a deeper one, to create a space where your old and new friends can connect with each other…only good things can happen from creating more of that type of serendipity in our lives. My wife and I have hosted two parties like this already and, as Nick has advised, we have our next one in the books! I hope you will, too. 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 Nick's website The 2-hour Cocktail Party

Today I sit down with my friend 

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

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

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

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

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