
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
Across the index
#3140 of 6183
Substance
Top 51%
outscores 49% of the index
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.
Averaged across 1 recently scored episode, with cited evidence.
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”
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”
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”
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”
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”
2026-06-29
First period on the Index - history builds from here.
1 scored on substance · 59 tracked in total.
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