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Dec 2, 2020 · 28m · we-live-to-build

The Oxygen Mask Rule Every CEO Forgets

Gresham Harkless Jr. · 15m spoken Sean Weisbrot · 9m spoken
0:00 / 0:00
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In this episode of the We Live to Build podcast, host Sean Weisbrot interviews media entrepreneur Gresham Harkless Jr. about building scalable media systems, delegating operational workflows, and implementing essential daily mental wellness hacks. Harkless emphasizes the foundational oxygen mask rule, reminding leaders that prioritizing personal self-care is vital for sustaining long-term venture growth.

How this conversation actually went

Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Sean holds 38.7% of the talking time here. How this is scored →

Sean as informed peer 4.3 Guest teaching 2.0 Guest disagreement 0.2 Sean pushing back 0.0
05100:0010:0020:002:12–6:12 · Sean as informed peer 4/10 Childhood Origins and Diverse Paths to Entrepreneurship Sean and Gresham have a warm, collaborative discussion contrasting their entries into entrepreneurship. Sean details his own unconventional start in China, while Gresham shares his early childhood newspaper venture.6:12–8:57 · Sean as informed peer 3/10 Founding Blue 16 Media and Modern Journalism Gresham shares his motivation for launching a media company amidst shifting journalism landscapes, and Sean builds on this by reflecting on modern news negativity.8:57–16:01 · Sean as informed peer 5/10 Overcoming Founder Loneliness and Building Support Networks Both exchange actionable management insights regarding founder loneliness and delegation. Sean elaborates on his structured hiring skill tests, while Gresham explains staging tasks internally before giving client-facing roles.16:01–22:14 · Sean as informed peer 6/10 Cultivating Daily Grounding Through Gratitude Journaling Gresham presents his gratitude journaling and meditation routine, prompting Sean to share an in-depth explanation of his own meditation methodology and thought-observation philosophy.22:14–25:16 · Sean as informed peer 4/10 Unlocking Subconscious Problem Solving with Coloring Books Gresham explains the cognitive benefits of coloring books for entrepreneurs, and Sean validates the psychological premise with his personal habit of stepping away to solve difficult problems.25:17–26:53 · Sean as informed peer 4/10 Applying Blue Ocean Strategy and the Oxygen Mask Rule Gresham shares his takeaways from Blue Ocean Strategy and emphasizes founder self-care through the oxygen mask rule, which Sean ties to notable business figures like Elon Musk.2:12–6:12 · Guest teaching 1/10 Childhood Origins and Diverse Paths to Entrepreneurship Sean and Gresham have a warm, collaborative discussion contrasting their entries into entrepreneurship. Sean details his own unconventional start in China, while Gresham shares his early childhood newspaper venture.6:12–8:57 · Guest teaching 2/10 Founding Blue 16 Media and Modern Journalism Gresham shares his motivation for launching a media company amidst shifting journalism landscapes, and Sean builds on this by reflecting on modern news negativity.8:57–16:01 · Guest teaching 2/10 Overcoming Founder Loneliness and Building Support Networks Both exchange actionable management insights regarding founder loneliness and delegation. Sean elaborates on his structured hiring skill tests, while Gresham explains staging tasks internally before giving client-facing roles.16:01–22:14 · Guest teaching 2/10 Cultivating Daily Grounding Through Gratitude Journaling Gresham presents his gratitude journaling and meditation routine, prompting Sean to share an in-depth explanation of his own meditation methodology and thought-observation philosophy.22:14–25:16 · Guest teaching 2/10 Unlocking Subconscious Problem Solving with Coloring Books Gresham explains the cognitive benefits of coloring books for entrepreneurs, and Sean validates the psychological premise with his personal habit of stepping away to solve difficult problems.25:17–26:53 · Guest teaching 3/10 Applying Blue Ocean Strategy and the Oxygen Mask Rule Gresham shares his takeaways from Blue Ocean Strategy and emphasizes founder self-care through the oxygen mask rule, which Sean ties to notable business figures like Elon Musk.2:12–6:12 · Guest disagreement 0/10 Childhood Origins and Diverse Paths to Entrepreneurship Sean and Gresham have a warm, collaborative discussion contrasting their entries into entrepreneurship. Sean details his own unconventional start in China, while Gresham shares his early childhood newspaper venture.6:12–8:57 · Guest disagreement 0/10 Founding Blue 16 Media and Modern Journalism Gresham shares his motivation for launching a media company amidst shifting journalism landscapes, and Sean builds on this by reflecting on modern news negativity.8:57–16:01 · Guest disagreement 1/10 Overcoming Founder Loneliness and Building Support Networks Both exchange actionable management insights regarding founder loneliness and delegation. Sean elaborates on his structured hiring skill tests, while Gresham explains staging tasks internally before giving client-facing roles.16:01–22:14 · Guest disagreement 0/10 Cultivating Daily Grounding Through Gratitude Journaling Gresham presents his gratitude journaling and meditation routine, prompting Sean to share an in-depth explanation of his own meditation methodology and thought-observation philosophy.22:14–25:16 · Guest disagreement 0/10 Unlocking Subconscious Problem Solving with Coloring Books Gresham explains the cognitive benefits of coloring books for entrepreneurs, and Sean validates the psychological premise with his personal habit of stepping away to solve difficult problems.25:17–26:53 · Guest disagreement 0/10 Applying Blue Ocean Strategy and the Oxygen Mask Rule Gresham shares his takeaways from Blue Ocean Strategy and emphasizes founder self-care through the oxygen mask rule, which Sean ties to notable business figures like Elon Musk.2:12–6:12 · Sean pushing back 0/10 Childhood Origins and Diverse Paths to Entrepreneurship Sean and Gresham have a warm, collaborative discussion contrasting their entries into entrepreneurship. Sean details his own unconventional start in China, while Gresham shares his early childhood newspaper venture.6:12–8:57 · Sean pushing back 0/10 Founding Blue 16 Media and Modern Journalism Gresham shares his motivation for launching a media company amidst shifting journalism landscapes, and Sean builds on this by reflecting on modern news negativity.8:57–16:01 · Sean pushing back 0/10 Overcoming Founder Loneliness and Building Support Networks Both exchange actionable management insights regarding founder loneliness and delegation. Sean elaborates on his structured hiring skill tests, while Gresham explains staging tasks internally before giving client-facing roles.16:01–22:14 · Sean pushing back 0/10 Cultivating Daily Grounding Through Gratitude Journaling Gresham presents his gratitude journaling and meditation routine, prompting Sean to share an in-depth explanation of his own meditation methodology and thought-observation philosophy.22:14–25:16 · Sean pushing back 0/10 Unlocking Subconscious Problem Solving with Coloring Books Gresham explains the cognitive benefits of coloring books for entrepreneurs, and Sean validates the psychological premise with his personal habit of stepping away to solve difficult problems.25:17–26:53 · Sean pushing back 0/10 Applying Blue Ocean Strategy and the Oxygen Mask Rule Gresham shares his takeaways from Blue Ocean Strategy and emphasizes founder self-care through the oxygen mask rule, which Sean ties to notable business figures like Elon Musk.

speaking balance: gold is Sean, purple is the guest (3 minute bins)

0:00 · Sean 72.5% · guest 27.5%0:00 · Sean 72.5% · guest 27.5%3:00 · Sean 47.1% · guest 52.9%3:00 · Sean 47.1% · guest 52.9%6:00 · Sean 27.6% · guest 72.4%6:00 · Sean 27.6% · guest 72.4%9:00 · Sean 44.2% · guest 55.8%9:00 · Sean 44.2% · guest 55.8%12:00 · Sean 22.9% · guest 77.1%12:00 · Sean 22.9% · guest 77.1%15:00 · Sean 32.7% · guest 67.3%15:00 · Sean 32.7% · guest 67.3%18:00 · Sean 45.3% · guest 54.7%18:00 · Sean 45.3% · guest 54.7%21:00 · Sean 23.6% · guest 76.4%21:00 · Sean 23.6% · guest 76.4%24:00 · Sean 33.4% · guest 66.6%24:00 · Sean 33.4% · guest 66.6%27:00 · Sean 56.7% · guest 43.3%27:00 · Sean 56.7% · guest 43.3%
Sharpest disagreement ▶ 15:20 Gresham clarifies his delegation background

In a very amicable conversation, Gresham gently clarifies that he did perform tasks himself before hiring others, clarifying his delegation approach after Sean's remarks.

 Hardest push from Sean ▶ 4:14 Sean challenges natural-born entrepreneur narrative

Sean contrasts Gresham's natural early entrepreneurial instincts by explicitly noting he never possessed that innate drive as a kid.

 Biggest teaching moment ▶ 13:24 Gresham explains founder bottlenecks via The E-Myth

Gresham educates listeners on how leaders become the primary bottlenecks in their own companies when they fail to delegate outside their zone of genius.

 Sean holds their own ▶ 19:42 Sean expounds on his meditation mastery

Sean demonstrates deep domain expertise by contrasting Gresham's balloon visualization with his own nuanced framework of becoming an emotional observer of thoughts.
the scores for every segment, with the reasoning behind each
ChapterTopicSean as informed peerGuest teachingGuest disagreementSean pushing backWhy
Childhood Origins and Diverse Paths to Entrepreneurship 4100 Sean and Gresham have a warm, collaborative discussion contrasting their entries into entrepreneurship. Sean details his own unconventional start in China, while Gresham shares his early childhood newspaper venture.
Founding Blue 16 Media and Modern Journalism 3200 Gresham shares his motivation for launching a media company amidst shifting journalism landscapes, and Sean builds on this by reflecting on modern news negativity.
Overcoming Founder Loneliness and Building Support Networks 5210 Both exchange actionable management insights regarding founder loneliness and delegation. Sean elaborates on his structured hiring skill tests, while Gresham explains staging tasks internally before giving client-facing roles.
Cultivating Daily Grounding Through Gratitude Journaling 6200 Gresham presents his gratitude journaling and meditation routine, prompting Sean to share an in-depth explanation of his own meditation methodology and thought-observation philosophy.
Unlocking Subconscious Problem Solving with Coloring Books 4200 Gresham explains the cognitive benefits of coloring books for entrepreneurs, and Sean validates the psychological premise with his personal habit of stepping away to solve difficult problems.
Applying Blue Ocean Strategy and the Oxygen Mask Rule 4300 Gresham shares his takeaways from Blue Ocean Strategy and emphasizes founder self-care through the oxygen mask rule, which Sean ties to notable business figures like Elon Musk.

Statements from this episode (4)

Disclosure
Weisbrot Gives Employees a Weekly Report of His Own Tasks
“I have a very open relationship with my employees and they know I give them a weekly report of what I've accomplished so they know what's going on outside of their own realm in the business.”
Sean Weisbrot Dec 2, 2020 ▶ 10:17
Opinion
Weisbrot: Founder Loneliness Stems From Busy Peers and Unique Pressures
“Because entrepreneurs are so busy, it's hard to find entrepreneurs that have the time to be your support network, which makes it even worse because the only people you find yourself wanting to know are other entrepreneurs. Because they're the only people who u…”
Sean Weisbrot Dec 2, 2020 ▶ 10:35
Insight
Harkless: Fixing Employee Mistakes Yourself Is a Major Leadership Failure
“Especially when things don't go as well as I want them to go, or, you know, somebody messes up on something with a client, you know, you want to jump in and just do it and just like, I'll just take care of it. But I know that is one of the worst things that yo…”
Gresham Harkless Jr. Dec 2, 2020 ▶ 14:10
Disclosure
Harkless: Restrict New Hires to Internal Tasks Before Client-Facing Work
“I usually have different levels to where a person is. So often when they first get started, they'll work on something that's internal that won't be anywhere close to the client facing. And it usually takes some time before they get to client facing work.”
Gresham Harkless Jr. Dec 2, 2020 ▶ 15:30
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