Living on Purpose w/ James Madison

James Madison is the Founder and CEO of On Purpose Life, where he helps professionals become more effective and inspiring leaders.  His superpowers are connecting, encouraging, and maximizing professional and personal development.

James is an Army veteran who served in Germany and participated in Operation Desert Storm. After serving in the military, he spent 25 years in supply chain leadership, operations management, and customer development roles for Fortune 500 companies.  Most recently, he was a managing director at a leading executive search firm before being led into executive and leadership coaching full time.

In this conversation, we dive into James’ work helping individuals find their purpose and live life on purpose.


Time Codes:

(3:30) – How do you describe what you do?
(4:30) – Why do your clients typically come to you?
(6:01) –  How do you guide someone to figuring out what it is they should be doing?
(10:31) – How does one go about discovering their purpose?
(15:32) – Should you be working ‘in’ your purpose all the time?
(18:25) – Does your purpose have to be tied to your work?
(19:40) – Being in purpose, on purpose.
(21:22) – What are the biggest struggles your clients need to overcome in order to live on purpose?
(23:33) – Setting boundaries and saying “no” to the things they should say no to.
(25:40) – The difference between ‘Return’ and ‘Reward’.
(27:34) – How do you say “No” to a good opportunity?
(31:13) – Being clear and having confidence.
(32:55) – James’ 4-steps of coaching: Awareness, Assessment, Approach, Action
(36:09) – How do you help people come to the realization that the destination is the journey?
(39:59) – How do you help people with their relationship with money?
(42:30) – Helping people learn to shift their mindset on money before they’ve “made their money”?
(45:10) – Money makes you more of what you are.
(46:00) – How does someone know when it’s time to take action?
(47:14) – Getting out of your own head when you’re over-thinking.
(50:14) – What are you sick of talking about?
(51:07) – What should people be talking more about?
(52:01) – What do you believe about people that may be contrary to general consensus?
(52:41) – What is the purpose of business?
(53:15) – Where can people find and engage with you?

Finding Your Flow w/ Diane Allen

Diane Allen was the Concertmaster (lead violinist) of the Central Oregon Symphony for 15 years, a well sought-after violin teacher for 28 years, and the author of sixteen music workbooks sold worldwide. Today, she consults and speaks with individuals and organizations on the Flow State. Diane has developed a proprietary process that enables people to be at their best anytime, anyplace, no matter how high the pressure.

Time Codes:

(2:44) – What is a Concertmaster?
(4:10) – How did ‘Flow’ come into your life?
(7:22) – Stick with it or recognize when to shift?
(8:44) – When did you start to pay attention to flow?
(11:48) – How were you able to harness flow to the point where you’re now teaching it?(17:49) – Interruptions are the biggest killer of the flow state.
(18:52) – The key indicators of being in the flow state.
(23:13) – Extracting your flow strategy.
(25:34) – How do you prime yourself before getting into a new task?
(28:56) – Stories from Diane about planting the flow seed into all aspects of life.
(33:02) – The scientific data behind flow & positive feedback loops.
(37:33) – What does your work look like?
(42:06) – O’Brien’s Flow strategy.
(49:24) – Final Thoughts from Diane.

Building Better Leaders w/ Mary Herrmann

Mary Herrmann is the Managing Director of the Global Executive Coaching practice of BPI Group. She leads a team of professional coaches in the U.S. and abroad, helping organizations drive change and deliver results through proven best practices in leadership and executive team development.

With a wide range of executive coaching and team assignments under her belt, Mary offers clients leading edge thinking combined with a deep understanding of HR processes and how they impact business results. She has designed individual development plans for C-level executives, and implemented executive coaching programs for large corporations. She has also worked with executive teams to help them achieve their goals and produce greater results.

Mentioned in this Episode:

  • “Only When I accept myself as I am, can I change.” – Carl Rogers
  • When Cultures Collide by Richard Lewis

Time Codes

(2:26) – Please pitch BPI Group and what you do.
(5:13) – How do you pick the clients you’ll work with directly?
(6:46) – What is it that clients are trying to make more effective?
(8:56) – Why are we so bad at seeing the impact we have on other people?
(12:15) – How do you structure a session that you know is going to sting the client?
(20:31) – How do you translate individual coaching to the team?
(22:48) – Examples of Conflict Norms.
(31:31) – Best practices for cross-cultural communication.
(35:32) – Do you find that Americans are better, worse, or the same at recognizing their way is just one way and not the best way?
(39:34) – Coaching the Coaches: What are the skills needed to be a good coach?
(42:50) – How do you slow down and ask a question when you clearly want to give a person advice?
(50:33) – Takeaways from the conversation.
(51:10) – What is the purpose of business?

The Career Editor w/ Leah Stallone

Leah Stallone is the founder of The Career Edit LLC, a full-service career strategy firm partnering with those ready to write, or rewrite, their career story. As a life-long career junkie, Leah spent the first 15 years of her professional life in talent management helping others find their professional sparkle. As “The Career Editor”, Leah shares the power of storytelling to help clients create meaningful career moments.

Mentioned in this Episode: 

Time Codes

(2:21) – Pitching The Career Edit and Leah’s work.
(3:01) – What element of storytelling do you specialize in?
(4:12) – How do you help shape someone’s resume into a story?
(6:09) – Why are people putting ‘Management’ all over their resume? Is it perceived as prestigious?
(7:33) – How do you help people decide whether they really need a new job or they just are feeling burned out?
(11:23) – What does the work look like to figure out what the issues are and what they really want to do?
(12:55) – Questions for people to journal on.
(21:22) – How do you help clients take this ‘next job’ off the pedestal and just figure out where they need to apply themselves?
(23:04) – Do you see a lot of folks turning their hobbies into careers?
(25:12) – Where do you fall on the spectrum of following your passion vs. not?
(30:24) – Learning what you don’t like instead of learning what you like.
(32:49) Role Play Scenario 1: 25-year old who doesn’t feel empowered at work because they don’t have the reps. What do they do?
(35:48) – Scenario 2: 35-year old who doesn’t feel empowered because they’re too far down the path. What do they do?
(37:51) – Networking when landing a new job.
(39:39) – What does good networking look like?
(43:51) – Networking when exploring a new field.
(52:42) – What is the purpose of a job?
(53:49) – Parting advice for someone in the job search

Making the Most of Your Money w/ Bill Bloom

Bill Bloom is the founder and CEO of Bloom Financial, a financial advisory firm focused on helping individuals “Retire as You Desire”. Among other clients, Bill works with business leaders and entrepreneurs to help them figure out what to do with their money and when. In this conversation, Bill shares his insight on our most common money issues, investing in ourselves and others, and how to get the help you need. 

Bill’s Books:


(2:24) – What is Bloom Financial?
(3:11) – Bill’s Origin Story.
(4:48) – What is the purpose of money and what should our goal be for money?
(6:28) – Do you think money is a corruptor?
(12:26) – The most common relationships people have with money, good and bad.
(13:38) – What behaviors do you see money scarcity creating?
(15:08) – Changing the scarcity mindset for over-spenders.
(16:14) – How many people can answer the question “what is the point of money?”
(17:39) – What are your conversations like with people who are under-spending?
(19:40) – Money Journaling.
(22:49) – What’s the balance between being frugal with money and having an obsession with non-spending?
(28:49) – Saving, Spending, and Investing for individuals.
(31:30) – What questions should individuals ask themselves when it comes to saving, spending, and investing?
(32:43) – Debt-free is the way to be.
(34:12) – Investing money in the market vs. investing money in yourself.
(37:04) – Investing in your people.
(38:34) – Where do you see business leaders getting hung up with money issues?
(40:33) – What do you say to people who have shame around money and saving?
(44:34) – Finding the right financial advisor and questions to ask potential advisors.
(48:59) – What are you sick of talking about when it comes to your work?
(50:09) – What are you most excited to be talking about?
(50:36) – What’s a belief you have that is contrary to what others might expect or say?
(52:18) – How does someone know when to bring on a financial advisor?
(52:44) – What is the purpose of business?
(53:58) – Wrap up & Bill’s Books

Corporate Responsibility w/ Marcy Twete

Marcy Twete is a leader in Corporate Responsibility & Sustainability with a history of working with multinational Fortune 500 companies. She has a background both broad and deep in ESG (environmental, social, governance) factors, ethical decision-making, marketing, and communications. She is the founder and CEO of Marcy Twete Consulting where she advises corporations of all sizes, their investors, and key partners on environmental, social, and governance risks and reputation management. 

In addition to leading her consulting practice, Marcy also hosts Table Stakes: The Podcast for Responsible, Sustainable Businesses & Leaders, discussing the issues of sustainability with forward-thinking leaders to forecast the future of responsible business.

Mentioned in this Episode:


(2:21) – Defining Sustainability & Corporate Responsibility.
(4:22) – The origin story of ESR & Corporate Philanthropy.
(6:26) – The changing expectations of corporations & the ‘Glass Box Company’.
(7:35) – Why should companies care about Corporate Social Responsibility?
(13:48) – Companies pursuing abusive policies vs. choosing not to do anything about systemically abusive policies.
(15:13) – Where do companies start to build out solutions?
(19:55) – Where does the responsibility fall in mid-sized companies?
(22:39) – Do you see clients working CSR into their values? How are they making it part of the fabric of the organization?
(26:16) – How do you build a process that is always evolving and never fall into the status quo?
(28:23) – The importance of not becoming complacent.
(32:34) – Self-policing & having tough, effective conversations.
(40:17) – Black, white, & gray areas. 
(43:59) – What are the biggest people issues you see companies dealing with today?
(47:29) – What is the purpose of business? 

The Only Constant is Change w/ Stephanie Waite

Stephanie Waite is the co-founder of ChangeNerd, an online community for change management professionals.  She is also the Founder & CEO of 7 AIR, a people strategy firm that unlocks & activates the people potential within organizations through consulting, executive coaching, and designing large-scale people systems, experiences, and strategies.  Stephanie serves as the President of the Association of Change Management Professionals (ACMP) Midwest Chapter, the largest chapter in the world.

Mentioned in this Episode: 


(2:18) – What is Change Nerd?
(4:52) – Stephanie’s Origin Story
(11:49) – What’s the smallest level of change that would necessitate change management?
(14:34) – What are the key frameworks of change management?
(21:03) – Is this just an exercise in getting your people comfortable with constant change or is it about one change at a time?
(25:09) – Eliminating the term “new normal” and selecting frameworks to implement.
(32:16) – How do you coach people to be able to make the time to start these processes?
(37:33) –  The difficulty of achieving short-term steps to implement a long-term change.
(44:44) – How did you train yourself to create imagery with your language?
(53:57) – The importance of reps, feedback, and values.
(59:08) – O’Brien’s experience taking a negotiating class.
(1:00:35) – Authenticity
(1:05:31) – What is the purpose of business?

Smartest One Loses w/ Christian Espinosa

Christian Espinosa is the Founder and CEO of Alpine Security, a cybersecurity firm now part of Cerberus Sential. He is an Air Force veteran, an Ironman triathlete, and a lover of heavy metal music.

Christian used to value being “the smartest guy in the room” but realized that to be his best and to win the fight against cybercriminals, he had to check his ego and build his emotional intelligence. He is now a speaker, author, and trainer in the Secure methodology, helping to make the smartest people in the room the best leaders in the field.

Mentioned in this Episode:


(3:05) – What is Alpine Security and Cerberus Sentinel?
(5:15) – What is White-Hat hacking & Red-Teaming?
(6:25) – How did you get into the world of cyber security?
(9:39) – Can you pitch your book and why you wrote it?
(11:33) – Do you have an example of how these High IQ-Low EQ team members interacted with a client?
(13:18) – How did you address your team’s claims that the clients were “ just not getting it”
(15:10) – What was the process of changing your own story internally of not being good with people?
(17:16) – Was it as simple as flipping a mental switch or was it more difficult?
(20:24) – How do you help others become better with people?
(22:18) – How did you help your team identify if they have a growth mindset?
(23:35) – What did you see that told you the team was making progress?
(25:35) – Neuro-Linguistic Programming & EQ Training
(28:26) – What does this Neuro-plasticity training look like in practice?
(31:38) – Doing vs. Being
(33:40) – What does EQ training look like in practice?
(37:41) – Establishing Core Values
(39:27) – Were there any other elements that had an outsized impact on training yourself or your team?
(41:00) – How much of people & EQ skill needs to be screened for when building a technical team?
(44:41) – The problem with High IQ – Low EQ in Technical leaders
(47:56) – What are you most sick of talking about when it comes to this topic?
(48:41) – What are you most excited to be talking about?
(50:06) – What is the purpose of business?
(50:56) – How did you become an instructor at the Bear Grylls Survival Academy?

The Glass Cliff w/ Tracey Wik

Tracey Wik is a business leader focused on helping women who’ve broken through the glass ceiling survive out on the glass cliff. A growing body of research shows that women who achieve leadership roles often do so in times of crisis or downturn, when the chance of failure is highest. On top of that, they are often given shorter timelines and fewer resources than their male counterparts. In this conversation, Tracey explains the issue and discusses what women can do before and after taking on these leadership roles to put themselves in a better position to be successful.

Mentioned in this Episode:


(3:20)- Tracey’s background and how she decided to begin doing this work
(5:20) – Was there a moment where the light bulb went off for you in realizing these issues for women were going on?
(8:01) – Defining ’Systemic’ and the idea of Bias
(14:01) – Do you have any examples where you’ve been in the room where decisions were made that negatively affected women?
(18:26) – O’Brien’s experience solo-parenting during Covid
(20:21) – The counter-argument: Women aren’t as interested in these high-intensity jobs or the pool of candidates isn’t wide enough
(22:52) – Thought Experiment: Fortune 500 company hires their first female CEO. What’s your response to that?
(25:02) – Defining the Glass Cliff
(28:05) – Is there something women can do when she’s up for a leadership role to get ahead of the Glass Cliff?
(31:14) – Are men being given the benefit of the doubt when in similar situations?
(34:56) – Tracey’s thoughts on “Women will be other women’s worst critics”
(39:54) – Changing the way we think about “Good Female Leader” vs. “Good Leader”
(45:51) – Do you have any other examples of the Glass Cliff?
(48:39) – The Bumble CEO having to constantly talk about her failures
(52:27) – What are you sick of talking about?
(56:31) – Wrapping Up

Kill Them With Kindness w/ Azimuth Leadership

Chris Schmitt and Scott Morley are West Point Grads, Army Special Forces “Green Berets”, and corporate leadership coaches with Azimuth Leadership. Chris founded Azimuth after 30 years in the Army to continue his life of service and pass along the leadership lessons he’d spent a lifetime learning. Whether it’s through their one-on-one and group coaching or their outdoor leadership excursion called The Traverse, Chris, Scott, and the Azimuth team are guiding their clients to show more kindness, live epically, and be stoked.

Mentioned in this Episode:


(3:33) –  Can you pitch the story of Azimuth to the audience?
(6:29) – How do you blend leadership consulting with the outdoors?
(10:32) – Scott’s transition out of the military.
(11:04) – What was it about Azimuth that made you want to make this your next career step.
(13:19) – What are the leadership frameworks that you learn at West Point?
(21:04) – Becoming a leader within West Point.
(22:20) – How do you suggest the average person get leadership reps in their own lives?
(30:50) – Leadership by Example
(33:07) – Living your values and guiding others to set their own values.
(35:28) – Is it important to have written values that everyone knows or should leaders just be good leaders?
(39:14) – Do you have any examples of how value shifting showed up in your time in the field?
(50:08) – The importance of coaches.
(54:57) – How do you balance accepting failure and needing great performance?
(1:00:15) – What is the purpose of business?