The Blunder Years

There’s a huge ecosystem of recruiting and HR content out there in the world these days, which I’ve contributed to in part for sure. In fact, just on this podcast since I launched it, I’ve had Tim Sackett (Episode 35) and William Tincup (Episode 18), who are both semi-big names in that world. Well, to spare you some additional bullshit about dealing with recruiters and how to get jobs, especially in a layoff-heavy pandemic period, here I talked to Robert, who was one of my original antagonists on LinkedIn, where everyone seems to broadly not like me that much. In this interview, we talk about how recruiters work, agency (third-party) models vs. in-house models, AI, how to get the most from a recruiter relationship, and more. We cover all this in a little under 22 minutes, so it should be what they call “snackable” content for you. I cannot promise you a job or anything, because I myself really haven’t had much success north of 33 landing a conventional W-2, but I can promise you some context for how to work with and think about the recruiting sphere in this one.

This is an interview with my friend Jack. We met at ESPN in 2005; I started there that year, and I think he had been there about four years at that point. As such, we've been friends for 15 years now, and a chunk of it is definitely rooted in sports. This interview even begins with sports discussion -- Coach K, whether he's dirty, recruiting in basketball, and the 1992 Kentucky vs. Duke game. (The Laettner shot.) But Jack and I have also both struggled with drinking over the years, so eventually we get into that. What is a sober journey? What is the difference between sober friends and drunk friends, and the context of where you meet people? Then, near the end, I took out a little section where he educates me on how health insurance works (he worked within that space post-ESPN). I learned a bunch there, but not sure you wanted to hear it. Instead, we talk about rearview mirrors vs. windshields, staying on "the path," God, more about drinking, and just two guys being friends for all these many years. 

Eamonn, who was on Episode 44 of this show, is also a friend from that time period. That Eamonn discussion is more about the broader biz world of advertising and data, and this episode is more about the intensely personal world of friendships, faith, and addiction struggles. I hope you find something in here of value. 

This guest is named Diana. If you scroll back in your podcast player from this episode all the way to Number 29 of this show, it’s the same guest. We originally met in June 2003 doing Teach for America, both of us training in Houston. OK, so Episode 29 -- not this one -- is largely about an assessment she sent me and I completed and what that says about me and her as professionals. So that’s a little bit more of a “work” episode, and this is a little bit more of a “personal” episode, because we’ve both been divorced somewhere among the 17 summers since we first met. The core difference contextually is probably that she’s still close with her ex and they have a spot in each other’s lives, which is not my experience. But we talk about a bunch of stuff in this episode, including the first wedding you attend after your own divorce, which can be trippy. Plus: expectations, reaction vs. response, coaching, COVID as a near-death experience, and more. Alright, let’s get into it.

I met this guest, Todd, on LinkedIn -- I think that is an under-discussed channel of mid-30s and above male friendship, oddly -- within the last six months to a year, I think. We interacted on a few posts about different work things and then taped this episode, which starts with a look at the early days of TiVo. Todd was actually in the room the first time live TV was paused. Then we get into parenting and the idea of 13 year-olds having a moral obligation to be dicks to their parents, and then we get into some life lessons including what he learned from a book called “Cured.” Along the way there’s also a discussion about swim lanes of life, and how to decide whether to even have kids. Hope you enjoy it. Let’s roll.

This is an interview with my friend Gabe. I think we first started connecting sometime in 2018, on LinkedIn first. You know it’s some real serious shit because eventually we became Facebook friends too. This is a pretty far-reaching discussion on religion, relationships, being a manager at work, conspiracy theories, drinking, partying, growing up, and more. I hope you find some value in it. Let’s roll. We’re actually going to start by me telling Gabe about a conversation I had with my pastor, who actually also ended up on this podcast at Episode 37 I think, if you want to go check that out.

At this point, I am not even sure the first time I met this guest, Mr. Eamonn. We were friends at ESPN, so I figure we met sometime around fall 2005. It’s incredible to think that we’ve known each other 15 years at this point, and/or the fact that I’m almost 40 and he’s over it. Since we met in Central CT, we’ve probably lived in a combined 10 places, and he’s been in Hawaii and now back in Ireland. Life is weird. This is basically a discussion between friends and sometimes biz-type partners who belittle each other along the way, on topics ranging from God to data to sports to advertising to algorithms to relationships and back again. It’s in line with a few episodes I’ve done where I catch up with old friends about the status of their life and belief structure at the moment, which I probably can’t monetize that successfully, but hell, I think it has value. So, here we go. I think we’re going to start with a Pope and religion discussion.

I started doing Teach for America in mid-June 2003. It was still about two weeks before LeBron would even be drafted into the NBA. The previous summer, the Knicks had made the second round of the NBA playoffs -- and I don’t think they have been back to that round since. As of mid-June 2003, I think the only time I had been to Texas was a layover in DFW Airport. So I moved down there with a bunch of preconceived notions and no idea what I was in for in terms of teaching in the inner-city, and one of the first kids (we were all kids at the time, like 22 or so) I met was named Dave. He was also from the general Northeast, a Knicks fan, etc. We became friends. 17 summers later, we still talk periodically, so we taped this podcast and talk about a bunch of different stuff, from fixing education to middle-school basketball to the difference between living in Houston and living in NYC (it’s not as big as you think). At the end, we talk about male friendships in your 30s. Dave actually still teaches, and went from Houston back to NYC. I went from Houston back to CT and NYC, then back to Texas but in the DFW area. Life is weird, and maybe this conversation underscores that. Let’s get to it.

I initially heard this guest, James Hollis, on The Art of Manliness podcast. That episode was on finding meaning in the second half of life. Hollis is a Jungian therapist, i.e. Carl Jung. We don’t get into a tremendous amount of Jungian stuff here, but we talk about meaning throughout life, masculinity, and the ability to be with one's self in a quiet room. Having been divorced and trying to cope with that reality, I can tell you that’s a very real measure of a man. This episode is only about 20 minutes, so give it a whirl when you can. Let’s dive in.

I would guesstimate that the largest percentage of my first 40 episodes were people between the ages of 25 and 45. This episode is with Terry, who is a little bit north of that arc -- to the point that our first discussion here is actually about retirement. She’s retiring from a W-2 later this month, actually. And her and her husband are selling a house they’ve been in since 1987, so we talk about that as well. (My mom and dad actually moved out of the apartment I grew up in around early 2016, and they had been there since 1974.)

She wrote a cool piece on Medium about down-shifting houses and the role of your adult children in that process. Terry is also a member of Just Be Social on Twitter. I’ve interviewed a bunch of them at present, including Brenda, Mollie, Theresa, Angelica, etc. Fun little group. OK, let’s get into this episode.

I’ll keep this intro short, but I’ll make it a tad personal. Last summer (2019), I had just been piped out of this agency gig that I thought would have ended up better. Instead, I was there eight months, it largely seemed like most people disliked me, and I had a very unceremonious exit. Because of that and largely being fed up with the broader work ecosystem and how people get gigs and jobs, I was kind of a mess for part of summer ‘19, day-drinking and the like. Nothing I’m really proud of. Well, I have a couple of decent in-real-life friends who were helpful in that time, and then I have a few “Internet friends” who also were. Mike Simmons is my guest on this episode, and he falls into the latter category. Always down to discuss work or football or working out or finding mentors or getting better as a person. Interesting dude. This is about maybe 45 minutes of us talking about a wide variety of topics, including parenting, learning, the movie Cast Away, and more. We come back to COVID-19 a lot, though, and in fact we’re going to start there in terms of how to communicate with your team regarding what’s happening in the business in these moments. Let’s roll.