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#3140Leadership is Tricky61.0 / 100Get badge
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Leadership is Tricky

Hosted by Erick Ocasio

Leadership is Tricky was born in 2019, as a platform to share experiences in exercising formal and informal leadership with a broad and diverse audience across a wide spectrum. A by product of us living our PURPOSE to serve and give back to servant leaders everywhere.

59 episodes · publishes fortnightly · latest 2026-06-29 · ~37 min/episode

Rank

#3140

Substance

61.0

/ 100

Breakdown

Scored 2026-07
Updated monthly

Leadership rank

#385 of 1041

Best B2B Leadership Podcasts →

Across the index

#3140 of 6183

Substance

Top 51%

outscores 49% of the index

Why it scores where it does

Leadership is Tricky ranks #3140 on The B2B Podcast Index with a substance score of 61.0 out of 100, scored across 1 recent episode. It scores highest on guest caliber and specificity & evidence. Byerly is a genuine practitioner - battalion commander, advisor to JSOC and 18th Airborne Corps-level generals, 13-year blog with 4-5 million views - giving him real credibility as an operator. However, his expertise is military leadership and personal reading habits, which is only loosely relevant to B2B operators, and he is partly a media-and-publishing personality now rather than a currently active executive.

The five-dimension breakdown

Averaged across 1 recently scored episode, with cited evidence.

Insight Density

12.0 / 20

The episode contains occasional useful specifics - the decision-journaling method (write the predicted outcome, revisit in six months), the jump from 4-5 to 45-50 books per year, and the advisor role framework - but these are buried in extended personal biography, mutual admiration, and generic leadership platitudes. The ratio of actionable insight to filler is low for a 45-minute runtime.

“I went from reading four to five books a year to like 45 to 50 books a year, uh, shortly after command. And what I found was like, as I was going into those positions of increased authority...I was able to not only rely on those experiences...but I was also able to rely on the stuff that I'd read about in books”

“he would write decisions down, and then he would write what he thinks going to result from that decision. And then he would go back in his notebooks and look at them. Six months, you know, um, removed from them to see if it was a good decision or not”

Originality

10.0 / 20

The core arguments - read more, journal daily, learn from bad leaders as well as good, find your passion - are thoroughly recycled leadership-podcast staples. The South Pole expedition analogy and the Ego is the Enemy recommendation are widely circulated. There is no contrarian or first-principles argument anywhere in the episode.

“just remain curious about yourself and remain curious about the world around you. Because I guarantee you, whatever problem, leadership problem or personal problem you're facing, somebody...has dealt with the same exact problem and they've written about it”

“Seth, uh, Godin, who's one of my favorite authors, he says, uh, you don't need more time. You simply need to decide”

Guest Caliber

16.0 / 20

Byerly is a genuine practitioner - battalion commander, advisor to JSOC and 18th Airborne Corps-level generals, 13-year blog with 4-5 million views - giving him real credibility as an operator. However, his expertise is military leadership and personal reading habits, which is only loosely relevant to B2B operators, and he is partly a media-and-publishing personality now rather than a currently active executive.

“I worked for the commander of jsoc, I worked for the commander of Resolute Support Mission Afghanistan. And then I worked for, for General Donahue, uh, when he was in the 82nd, and then as he transitioned over to 18th Airborne Corps”

“my very first company commander, guy named Lewis Netherland, was, uh, a platoon leader under, at the time, Lieutenant Colonel H.R. McMaster”

Specificity & Evidence

13.0 / 20

There are pockets of genuine specificity - named generals, exact dates, book titles with authors, a claim of 4-5 million website views and ~1,000 notebook sales - but most assertions rest on personal anecdote rather than data, and the book recommendations lack any explanation of what concrete outcomes they produced.

“January 1, 2021 was the first time I started journaling, and I've done it every day since then”

“we've sold like a thousand copies of it which is cool because people are giving it as gifts”

Conversational Craft

10.0 / 20

The host asks broad, open-ended questions ('what was that like for you'), never pushes back on any claim, and frequently redirects the conversation to his own experiences and reading list. There is no productive disagreement, no follow-up that extracts deeper mechanism, and the closing section devolves into a mutual book-club exchange.

“What was that like for you, uh, going through the service college. And then who were some of those early inspirational figures in your life?”

“Yeah, it's funny though, just to watch you through this...you light up when you talk about what your passion and what you feel like your purpose is”

Standout episodes

  • Season 6 - Episode 4 - Joe Byerly

    2026-06-29

    61

Rank over time

First period on the Index - history builds from here.

Episodes

1 scored on substance · 59 tracked in total.

  • Season 6 - Episode 4 - Joe Byerly

    2026-06-29 · 45 min

    61 / 100

Frequently asked

What is Leadership is Tricky's substance score?
Leadership is Tricky scores 61.0 out of 100 for substance and ranks #3140 on The B2B Podcast Index. That puts it ahead of 49% of the B2B podcasts we rank and #385 of 1041 in Leadership. The score reflects insight density, originality, guest caliber, specificity and conversational craft across recent episodes - not downloads.
Is Leadership is Tricky worth listening to?
Leadership is Tricky is ranked on The B2B Podcast Index with a substance score of 61.0/100. See the five-dimension breakdown above to judge whether it fits what you're after.
Who hosts Leadership is Tricky?
Leadership is Tricky is hosted by Erick Ocasio.
How often does Leadership is Tricky publish?
Leadership is Tricky publishes fortnightly, has 59 episodes, released its most recent episode on 2026-06-29.
Which Leadership is Tricky episode should I start with?
Our highest-scoring recent episode is "Season 6 - Episode 4 - Joe Byerly" (61/100) - a good place to start.

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Guests who've appeared

Joe Byerly

Topics this show covers

The themes that come up most across this show's episodes.

82nd Airborne DivisionFrom the Green Notebookproperty accountabilityJSOC (Joint Special Operations Command)Resolute Support Mission AfghanistanGeneral DonahueGeneral MillerGeneral HoweH.R. McMasterBattle of 73 Easting

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