Key Takeaways:

[3:24] Charlie’s background and why he decided to become an entrepreneur.

[9:16] It typically takes 18 months to 36 months just to figure out what you're doing as an entrepreneur.

[13:13] Mark talks about his career journey from going to film school to going to a corporate company at a franchise company making videos. There, he started to look at which projects he enjoyed the most and which ones had the highest profit margins that he could deliver.

[14:01] The lowest point in Mark’s business and how it changed.

[16:13] Mark’s story of using his high intelligence, talent, and energy in a way that served himself and others.

[23:47] Asking for help is one of the greatest things we could do.

[24:15] When you accept the gift of not knowing, it opens up all these possibilities.

[24:20] It’s okay that you don’t know, and you don’t have to fight that.

[31:42] What path will get your message in front of the people you want to speak to, and then once you are there, how do you build an experience better than your competitors?

[33:16] The principles of marketing and sales haven’t really changed since 2000 years ago. We’ve just gotten better at implementing those principles.

[45:28] Mark’s decision to stop running his business.

[1:04:11] Doing our best work requires us to center ourselves on our dreams and our passions.

[1:11:05] Ask yourself: what’s the smartest thing you can do next, and then, what’s the most courageous next step you can take on that project?

[1:19:38] Mark’s Challenge: Let him help you.

Mentioned:

Mark Drager: Website | Podcast

Richard Branson

Fast Company

Breakthrough Advertising

Key Takeaways:

[2:57] Ruby and Eric discuss some of the unique delights and challenges of being part of a writing trio.

[7:45] What is the bridge between this book and Morag’s book Cultivate: The Power of Winning Relationship?

[8:05] What are the intentional choices you can make to build ally relationships?

[12:44] Ruby and Eric break down the five components of an ally mindset:

• abundance and generosity
• connection and compassion
• courage and vulnerability
• candor and debate
• action and accountability

[13:23] In order to get more allies, you have to be one yourself.

[25:43] How can we start with small ripples of joy in our own lives and have that branch out to help others?

[28:12] Are two-hour staff meetings really necessary? And if so, how do we make them more efficient and profitable for everyone involved?

[34:13] If you’ve invested in your relationship, it’s going to withstand weird moments. In the meantime, what should we do when a sideways moment occurs?

[59:54] Challenge: lean into having the hard conversations. Keeping your head down isn’t going to change a damn thing. And, check out the Ally Mindset Profile to give you some insights into what comes naturally to you, as it relates to the five practices.

Mentioned:

You, Me, We: Why We All Need a Friend at Work

Ally Mindset Profile

John Gottman

Key Takeaways:

[6:20] We are in a media environment that is saturated with messages about how much more we could be doing.

[7:27] Charlie, Jenny, and Tara define capacity and what that means to them.

[10:51] What are some of the things that can make working in a team overwhelming?

[14:17] When our world gets too big, we tend to get disengagement and boredom.

[15:38] The difference between rigidity and rigor in goal setting.

[17:09] Why is it important to bring in conversation about rigidity versus rigor as it relates to capacity and the ambitions that so many of us have, especially for creative pursuits?

[21:55] How do you effectively and professionally communicate when you’re overcommitted?

[29:07] Just be honest about what you can and can't do.

[32:07] Yes, technically we all have the same 24 hours as Beyonce, but we have different 24 hours.

[45:34] At the heart of hustle culture is a solution to a substantially larger problem that we have in the 21st-Century economy. Charlie, Jenny, and Tara discuss how hustle and bro culture is a larger sign of a patriarchy and white male privilege.

Mentioned:

Jenny Blake

Tara McMullin

Key Takeaways:

[3:13] Jennifer discusses finding her voice in the workplace equality movement as a professional, a member of the LGBTQ+ community, and someone who recognizes their privilege.

[5:25] Jennifer talks about carrying the LGBTQ identity as a source of challenge, and using it as a vehicle to transform her own leadership.

[12:22] When getting leaders and insiders to enact lasting change, we need to focus on DEI efforts on the moral case, just as much, if not more than, the business case.

[15:43] If you are an insider, you can push on other insiders to lead differently.

[17:40] Up to 75% of change management efforts fail, especially the top-down-led ones.

[21:01] We can find core issues that we can focus on, which will then create ripples of change. One example of this can be toxic masculinity.

[33:01] We should recognize that the differences between us are ones we should face and name, rather than sweep them under the rug.

[38:11] The journey of understanding others is challenging and may reveal things about ourselves that we never expected. It’s important to be patient, humble, and transparent about our experience. Humans don’t learn by shaming one another.

[1:01:28] Leaning on others within your community is super important, and Jennifer talks about the profoundness of an ally showing up to help speak for someone who can’t.

[1:09:49] Jennifer’s challenge: get comfortable with being uncomfortable.

[1:10:44] DEI is a laboratory for human evolution, and it challenges us at the deepest level in the not knowing.

Mentioned:

Jennifer Brown

How to Be an Inclusive Leader

DEI Deconstructed: Your No-Nonsense Guide to Doing the Work and Doing It Right, by Lily Zheng

bell hooks

Can magic strike twice? As we learn in this episode, it most certainly can. Charlie welcomes Jadah Sellner, best-selling author, business coach, and the host of the Lead with Love podcast. Jadah shares wisdom from her own experience of going from the “green smoothie girl” to an anti-hustle and pro-sustainable leadership business coach. Jadah talks more about her #shebuilds movement, which helps founders build sustainable businesses without burnout, some tips on moving forward when you feel like you’ve outgrown your current situation, and how we can apply anti-hustle productivity in our personal and professional lives. Jadah and Charlie talk about their creative process of book writing, moving from fear to love, and how we can define our “enough” to move through the world more intentionally.

Key Takeaways:

[3:41] Jadah talks about co-founding Simple Green Smoothies with her then-business partner Jen, and the interesting journey to have the conscious uncoupling not only with a business partner but with an identity of a body of work that she built.

[5:20] Can magic strike twice? The answer is yes.

[5:58] What should you do when you feel stuck in a pattern, yet your heart and soul call you in a new direction?

[10:08] Sometimes we need separation to rebuild on our own and find our way.

[10:52] Jadah shares a few people and situations that helped her create her own skill set and tools to pull from in her current life.

[11:13] How is She Builds different from anything Jadah has done before?

[12:17] Pay attention to where your natural curiosity and interest lie.

[14:31] Jadah is an immersive creator, and she talks about giving herself the space to process and creatively cocoon while she is going through the process of creative writing and output.

[17:41] Things flow much more easily when we embrace the fact that each project brings a new creative process.

[23:15] The core message behind She Builds is that hustle culture isn’t working for women.

[32:51] Sometimes advocating for yourself also means having to push back deadlines and be honest with yourself and others that things may not happen on the exact day you plan for them to happen.

[38:55] How can we move from fear to love? Jadah breaks down her definition of “L.O.V.E.”: lead, optimize, visualize, and expand.

[41:23] In a world where your to-do list can be a bottomless mimosa, it’s important to have an intentional and practical relationship with your to-do list.

[48:47] Jadah’s growth edge now is being in a creative process with her book.

[50:43] Jadah’s challenge: define your “enough” number. It is personal for everyone and can help move you out of hustle culture.

Mentioned in this episode:

Productive Flourishing

Start Finishing: How to Go from Idea to Done, by Charlie Gilkey

The Academy

Momentum App

Jadah Sellner

@jadahsellner

Lead with Love Podcast

She Builds: The Anti-Hustle Guide to Grow Your Business and Nourish Your Life

Elizabeth Gilbert

Neil Gaiman

Toni Morrison

Key Takeaways:

[4:36] Tara talks about what led her to create the What Works book, a blend of her own personal quest to re-establish her relationship with work and goals, mixed with conversations with people who had all sorts of different relationships to productivity and goals.

[6:08] In the process of Tara’s research for the book, it brought up a deeper conversation of how much culture, family, and upbringing have on our identity, which makes an impact on how we structure our work and the goals we set.

[6:49] We are bombarded by marketing and societal messages that make us feel like we aren’t good enough, or aren’t doing enough.

[7:22] Tara and Charlie discuss why we don’t do the things we really want to do, and why working on teams can be so hard, even though we are primed to work with others.

[12:25] We unpack the validation spiral, and why it’s so common.

[16:21] Externally, one of the ways that we play into the validation spiral is by saying yes to things, taking on projects, and spreading ourselves too thin to do anything impeccably.

[20:23] So many of us are socialized to be the supporting actor when really we can be the lead actor in our own story.

[24:01] Ask yourself: what resources do you need, and where might they come from?

[33:15] When “shoulding” and “supposed to-ing” yourself, get clear and concrete about what exactly you are looking for. Try to get specific about numbers and benchmarks.

[40:15] Why don’t we ask for help before we absolutely need it?

[45:10] Get a support team together before you need the help.

[52:12] As a community, we can learn to break down resistance to ask for help and more openly offer help to others without expecting much in return.

Mentioned in this episode:

Productive Flourishing

Start Finishing: How to Go from Idea to Done, by Charlie Gilkey

The Academy

Momentum App

Broken

Down Girl

Tara McMullin

What Works: A Comprehensive Framework to Change the Way We Approach Goal Setting

What Works 

What Works Network

Key Takeaways:

[4:17] Mark talks about the experience of almost dying from a rare form of lymphoma when he was in his 30s, and how it was the introduction to facing the unavoidable work of the friction that comes with life.

[5:32] We must face what is done to us, but we are more than what has been done to us.

[5:41] Mark talks about how the pandemic showed our generation it’s time to learn to choose love over fear, and compassion over self-interest.

[11:20] One of the first “faults” goes back to the Industrial Revolution, where this is the first time in history that where we live and work is separated.

[17:16] Reality TV is our present-day virtual Colosseum.

[27:23] Often spiritually, the safest place is in the center.

[28:09] Every one of us has a daily and perennial choice between love and fear. But there’s a difference between letting fear move through you and obeying it.

[34:38] Through solitude, we restore our direct connection to the universe, and through relationships, we restore the wonder of being human and compassion and kindness.

[37:11] The bad news is we’re always falling. The good news is there’s no bottom.

[47:56] Mark’s challenge and invasion: inhabit life fully by being as open-hearted and as loving as possible. This will require courage, strength, and kindness.

Mentioned in This Episode:

Productive Flourishing

Start Finishing: How to Go from Idea to Done, by Charlie Gilkey

The Academy

Momentum App

Mark Nepo

Surviving Storms: Finding the Strength To Meet Adversity, by Mark Nepo

The Social Dilemma

Think Like a Monk: Train Your Mind for Peace and Purpose Every Day, by Jay Seti

No Mud, No Lotus: The Art of Transforming Suffering, by Thich Nhat Hanh

Key Takeaways:

[4:54] Lisa would consider herself mentally ambidextrous. She likes structure and hard problems but also enjoys free thinking. Both these qualities help her as a storyteller and entrepreneur.

[5:04] Lisa talks about deciding that she wanted more out of early retirement than sitting and eating pancakes all day!

[8:36] As a polymath, you can both be multidisciplinary and singularly focused.

[12:44] Sometimes people put themselves in a prison of their own making. Lisa talks about how we can lean into creativity and fun rather than being stuck feeling like we have to do one thing.

[13:21] When we start thinking about making decisions that affect our evolution, we tie in three factors that make them super hard and high-stakes: we make a decision, it is non-reversible, and it seems like it’s non-recoverable.

[15:02] Sometimes we think that we are failing, when we're really in the middle of succeeding, but the only way you know that is to know that you are trying a new thing and experimenting.

[27:00] Lisa discusses how her definition of success was flawed and how she was basing success on outcome rather than creating a process that really reflected where her money and time were going, and if this matched her values.

[38:26] Lifestyle changes can take time.

[1:04:29] It’s often what we are ashamed of and embarrassed about that can lead us to really get what we want.

[1:08:03] Lisa’s challenge to you: make yourself a “to don’t” list.

Mentioned in This Episode:

Productive Flourishing

Start Finishing: How to Go from Idea to Done, by Charlie Gilkey

The Academy

Momentum App

Behind the Brilliance Podcast

Lisa Nicole Bell

@lisanicolebell

A Whole New Mind

Mr. Money Mustache

If you’ve ever wanted to do interesting projects with friends and family but traditional business ownership models didn’t feel quite right, this episode is for you. Kate Strathman is an artist, writer, and rebellious spirit. As a multidisciplinary business owner, Kate taps into each of these traits to help others build equitable team structures and dream up alternative business models that may have never previously existed. In this episode, Kate talks about the definition of a collective and how it differs from a cooperative, how to know what purpose, structure, and operating model to use, and what to do when you know it’s time to shift. Kate also discusses how we can better create value for people through our business.

Key Takeaways:

[3:56] Kate talks about how someone with an art degree and a love of wandering around India ended up in bookkeeping and a finance consultancy.

[12:35] Kate defines a cooperative as a business that is owned by the people that benefit from it. There are different types of cooperatives. A worker co-op is a type of business where the employees directly own and control the business, generally on a democratic basis of one person/one vote.

[15:20] In a worker co-op, ownership derives from working in the company, rather than investing in capital.

[23:20] Pay and power are not the same things. Just because you have 50/50 ownership in the business, it might not necessarily mean you get paid the same.

[28:07] Kate talks about some of the conditions that skew us towards a co-op versus more of a standard partnership: the number of people, owner obsolescence, and creating a multi-generational structure.

[49:11] What is the line between resilience and interdependence?

[51:27] Kate’s challenge: think about one way the structure of your business could shift to benefit all the humans and communities it touches.

Mentioned in This Episode:

Productive Flourishing

Start Finishing: How to Go from Idea to Done, by Charlie Gilkey

The Academy

Momentum App

Wanderwell Consulting

Kate Strathmann

Simple Numbers, Straight Talk, Big Profits!: 4 Keys to Unlock Your Business Potential, by Greg Crabtree, with Beverly Blair Harzog

This week, New York Times bestselling author and essayist Esmé Wang joins the show. Esmé first talks about growing up with immigrant parents, and how that shaped her ideas of accomplishments and what it meant to succeed as a creative. She details how she went on to go to Yale, became a scientist, and then veered onto the path of writing and how her illness taught her to just “be” instead of always trying to be productive. She shines a light on the lessons she learned from having her book rejected 41 times before being selected as a once-in-a-decade award winner. Esmé is also the founder of The Unexpected Shape Writing Academy.

Key Takeaways:

[2:51] When you’re a creator and dealing with disabilities and chronic illness, one of the things you have to accept is that your plans don’t always work out the way you want them to, because life happens.

[3:19] Esmé talks about growing up as a professional writer with immigrant parents from Taiwan who put a very high emphasis on attending an Ivy League school and productivity.

[12:02] One of the problems of living a creative life and unconventional path is that the normal markers people would use for success may not be there.

[13:05] Esmé’s first book was rejected 41 times before it was picked up by a publisher. She talks about how luck plays a role in success.

[17:53] We all have the same hours in a day as Beyonce, but definitely not the same level of support!

[21:01] Esmé discusses her own dealing with illness as a person that put high importance on output and productivity.

[25:07] How can people with chronic illness and disability reframe the way they look at productivity and time management in a way that doesn’t lead to frustration and disappointment?

[28:01] Culture and our capitalistic society are obsessed with productivity.

[35:08] Able-bodied people often don’t realize how much it takes for someone with a disability or chronic illness to do the things they view as “normal” or easy.

[38:41] How the Momentum App can help.

[42:22] How we can better communicate with the people in our lives when we need a break or are running out of energy.

[53:24] Challenge: write down EVERYTHING you do in a day. Everything. You are doing way more than you think you are.

Mentioned in This Episode:

Productive Flourishing

Start Finishing: How to Go from Idea to Done, by Charlie Gilkey

The Academy

Momentum App

Esmé Wang

The Unexpected Shape Academy

Adam Grant

Brené Brown

Tara Newman is the Founder and CEO of the Bold Profit Academy and host of the Bold Money Revolution. She joins the show today for a conversation about the importance of remembering why most of us start businesses and seek out entrepreneurship, how common growth strategies can lead to a lack of resiliency, and how service providers can avoid the mindset of selling themselves. This is a great episode for those wanting to make their business work for them and their life, rather than having their life be working for their business.

Key Takeaways:

[3:58] Many of us come to entrepreneurship out of necessity. Tara talks about her diagnosis of Lyme Disease, and how getting COVID-19 also flared up her EB Virus. To heal, she needed proper time and space to focus on her health journey, which having your own business can allow.

[8:00] The pandemic cycle introduced new layers that we hadn’t had to consider before. 

This resulted in many of us having to re-engineer our businesses.

[15:26] Why it’s detrimental to condition your reward system to seek likes, followers, and comments rather than true value.

[19:32] Tara explains how the online business model is the most costly thing she has ever seen.

[23:03] Tara is a big believer that you can be a millionaire without having a million-dollar business.

[24:49] There is no regulation for digital advertising and research shows that up to 88% of ad clicks are fraudulent.

[27:45] Publicly held companies are cutting their ad revenue and marketing because they know they can make sales without them.

[38:07] The biggest benefits to having a profit-first framework as a method.

[48:05] What has Tara learned as a wartime leader?

Mentioned in This Episode:

• Productive Flourishing
• Start Finishing: How to Go from Idea to Done, by Charlie Gilkey
• The Productive Flourishing Academy
• Momentum App
• Tara Newman: Bold Profit Academy