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Jul 20, 2026
06 Blair Jeffery Honest XD Podcast
06 Blair Jeffery Honest XD Podcast
00:00
23:59
Transcript
0:00
[upbeat music] Hey again. Uh, all right, so I'm catching up on these last couple videos that I have sitting and have been collecting dust for a few weeks. Today, you're gonna meet Blair Jeffrey.
0:11
Blair is someone that I've had the good fortune of working with at a couple of different companies. His area of expertise is payments and fintech.
0:17
Just really, really smart guy in that, uh, industry, in that sector, way outside of my, uh, [chuckles] area of comprehension, uh, even though I've worked with him a few times. Really good heart, incredible mind.
0:28
He's always the smartest guy in the room. Would never admit it. Would actually roll his eyes at it.
0:32
But just somebody that, you know, I would jump at the chance to work with again in the future, and I think I'm certainly not alone in that [chuckles] in terms of people that have worked with him.
0:39
So we, we talk about things. We talk a little bit about payments and startups and AI. We get into talking about fatigue and just kind of our general, uh, culture that we're living through some shifts in right now.
0:50
So this is also the last video that I used Google Meet to record. So if, if you have been watching, you know the edits have been not choppy, but they just take me a little bit more time.
0:59
And so after this, I started using Riverside, which, uh, will hopefully reduce the, uh, friction in me getting out the videos and the, you know, the podcast segments. So enjoy this conversation I had with Blair.
1:10
Go give him a follow and, uh, yeah, we'll see you on the next one. What I typically say is, I've been in fintech and payments my entire career. I've been in and out of a bunch of companies. I do early stage stuff.
1:22
If you're asking me what I'm doing right now, um, it's a little bit of this and a little bit of that, but I'm not doing anything in a full-time capacity. I just walked out of one and,
1:32
you know, how long is it gonna be before I walk into the next? I don't know. I'm gonna have to get excited, um, before I decide that. I'm not so sure that my place in this world is my title at some company, so...
1:44
Do you get anxiety when you're in the in between? So present tense, no. Past tense, very. Uh, I used to get extremely anxious. Um, I think I was telling somebody the other day, and, you know, I've roughly worked,
2:02
call it 30 years-ish, and I've changed jobs a lot. Um, I think the longest I've-- I was, I was ever at a job was eight years, and prior to that was probably four.
2:12
So I've done, if you do the math, you know, I've probably been at 10 different companies. Um, up until this last one, I guess it's not necessarily true.
2:21
There's two instances where I've walked out of a company without walking straight into another opportunity, and when I say straight, I mean the next day or the following week, you know, after the weekend.
2:35
Um, and so it's a, it's a little bit... I would say that I was a little more anxious the last time I did it. Um, but I also was walking out right during COVID, and so kind of everybody was checking out for a period.
2:48
Um, so it wasn't as... didn't drive as much anxiety. This one, a lot different. Um, it was much needed,
2:57
and I've actually am having to tell myself to slow down, um, that I need to be patient, um, because things come up and people hear you're in the market, and then they make a phone call and, "Hey, let, let's make something happen."
3:10
And while it feels good to feel wanted, the reality is I also don't wanna just plunge back into something unless I really get wowed by it, and
3:21
part of the reason I introduced the concept of not having a title is 'cause I haven't been wowed by anything just yet. It's a good bar to set, I guess, having to be wowed. I don't know.
3:32
I mean, I, I, I think I've, I've told you this in the past. I-- for me, there's two primary components, um,
3:41
over my career that I've just kinda looked at now and, like, when I look at opportunities, and the first one is just that I'm working with people I
3:48
really respect, um, whether intellectually or from an integrity perspective or whatever. So I wanna work with people that I really like.
3:57
Um, and that's not always possible, uh, or it hasn't in my career, but I've just gotten to the place now where I've kind of uncompromised in that.
4:04
And the second is that I want, really wanna work on something challenging. I like working on tough stuff, tough problems. Um, I'm not a
4:14
person who likes to work in a manufacturing space and kinda just build the next widget and widget and widget, um, and do small tweaks. I, I like looking at big stuff.
4:23
But I will tell you over time, probably the last 10 years, that so when I take those two components, the distance between one and two has drastically expanded. One is infinitely more important than two now.
4:39
I just really have to work with people that I respect and wanna be around because, you know, I spend anywhere between 60 and 80 hours a week doing this, you know?
4:49
And then how much mind share gets taken up in addition to that? I don't know. I mean, we're probably all sitting... If we're serious about it, we're probably all sitting between 80 and 100 hours of mind share a week.
5:03
That's a lot. Um, and so anyway, to do that with, um, a team of people that maybe you don't, or y- you just are misaligned, maybe it's not respect, but just misaligned, for me it's just a, it's a lot of wasted time.
5:18
What are some of the things you've ob- observed, like so culture and people being one of them, um, what are some of the other things you've either struggled with or that you've, like, gone through in terms of any sort of transformation in how you value or, you know, find your identity and stuff?
5:36
I mean, for me, uh, work's always gonna be humbling because I don't... I'm not the kind of person that feels like I have it all figured out. Um, I don't have that level of confidence.
5:48
And in fact, I probably skew a little bit the other direction, just the imposter syndrome thing of, you know, there... From time to time, people have to actually talk me into,
5:58
"Actually, you do have that skill set," you know? Um, 'cause I, I think I'm a tough grader on myself. So, um, what I've seen In five years, um, a dramatic shift in the pace. It was...
6:14
It, it always seemed like, you know, you and I spent a lot of time in startups, and startups always have a pace and a cadence to them that is kind of unsustainable by design, right?
6:25
You, you can do it for periods of time, but at some point you are going to break down. And when you break down is when you start bringing on other people. Um, that's sort of one of the thoughts, if you have the cash. Um,
6:39
and sometimes even if you don't have the cash, you gotta do it. What I've seen is that pace
6:45
accelerate dramatically, um, just in the last five years and, and whether that's just an interconnectedness from a global perspective, um, you know,
6:56
just walked out of a company that I think for the most part was taking itself pretty seriously on a global expansion opportunity, um, not having any idea how to do it, but took it seriously.
7:10
Prior to that, I didn't spend a lot of time even thinking about global. Um, the US market and/or at least tangentially the North American market was plenty big enough.
7:20
And what we're seeing now is there's so many people in the space, and the barriers to entry, whether that be technology,
7:29
throughput, or personnel, um, a lot of those barriers have been lowered, if not eliminated, and so people can enter the market really quick. And so the, the answer to that is how do I increase my market size?
7:43
Okay, well, I can get broader and wider, but when you do that, the pace at which you have to grow and operate becomes so much faster. So I've seen a, a huge acceleration there. I know the, the big
7:59
thing to talk about out there is AI and does, you know, d- does, has AI changed things in the space? Um, uh, uh, my honest perspective is that I think,
8:11
uh, while I think AI has the promise of doing an awful lot of things, I think the reality is, um, it hasn't necessarily made us more productive at this point.
8:24
Um, un- unless you just look at your job as purely automatable, and then yeah, I think, you know... And, and I would look at that and say, "Well, it's probably about time."
8:32
Maybe you should've been automating your job prior to the... But so the pace isn't-- I don't think the pace is accelerating necessarily with AI.
8:40
I think the pace in AI is accelerating, but I don't know if the pace from a productivity has, has changed. But the promise of it has accelerated people's movement within companies.
8:53
Um, and I, I always think back to the... I'm old enough to remember, you know, Netscape browser and, oh, we have the promise of the internet. It's gonna change everything.
9:01
And I, I remember reading all the time that this was gonna change the world because, um, which ultimately it did, but it was gonna change the world because it was gonna eliminate paper.
9:12
You know, people weren't gonna print things anymore and whatever. And what I found in my own experience and in the experienced professionals, actually, people just printed more.
9:21
They had more access to information, and so they did more and more and more of it.
9:25
And I think AI's gonna kinda do that, but I think the, some of the pace I don't think has necessarily been affected by AI, at least my experience.
9:34
I spent some time wondering what the, what the differentiators are gonna be as the playing field- Mm-hmm... gets leveled in a lot of ways. Um,
9:43
when you think about where you wanna be in the next five years, I think the next five years are gonna go even faster than the last five.
9:50
But, like, what are the things you're gonna double down on personally because you think they're gonna be differentiators? You gotta get out of the noise. Um, and that's what I always struggle with. Like,
10:01
all the apps and all the things on my phone, at least from a consumer perspective, regardless of whether they're fintech or not, there's just a lot of noise. And is there, is that consolidation that solves the noise?
10:14
Is that platform that solves the noise? Or overall, are people gonna reject noise at some level and
10:25
get a, a shrinking on, you know, I, I need to minimize my overall sort of intellectual footprint or whatever that ends up being, like technological footprint's probably the better way to put it.
10:36
And so I, I wonder about some plays there, you know, um, to... I think we've done a lot of, a lot of stuff on XD on, like, getting better and more streamlined approaches, but yet
10:51
there's more and more software that I'm having to interact with on a daily basis, and it feels like there's a little bit of a fatigue there. And I wonder if that fatigue, if somebody's gonna step into that space and
11:05
kind of push back on a little of that fatigue and end up monetizing on it. I don't know. Just two sort of things that I ponder. Yeah. I, I spend a lot of time thinking about that fatigue word. I've probably used it
11:18
with you multiple times over the past couple of years. Yeah. Um, when it comes to, like y- you've talked about a bunch of stuff that circles around the topic of problem statements.
11:28
I think one of the things that I've realized for myself after all this time I've spent in SaaS is like I've, I've spent a lot of time forcing myself to become a problem solver because that's how I've justified my existence, so to speak.
11:42
So, like, I've- I'm a creative person, but I have to f- I have to fall in love with a problem in order to justify my existence.
11:48
I think you're a type of person that just you look at problems much more inherently as, like, fun. Maybe not fun's the right word, but I guess my question is: how do you continue staying in love with problems
12:01
and letting that be the thing that never satisfies you or leads you to be a builder? Uh, it's been an inhibitor for me. Like, I, I feel like there's roles in companies, and
12:16
sometimes the problem solver is not the best role. Um, yeah, and, and that has been a persona that I've taken on is, like, somebody who, who can solve problems.
12:28
Uh, but then the, the challenge with that is if you think of yourself strategically, and I, I don't know, you know, am I the most strategic person on the planet? No.
12:38
But I do have sort of a, a, a thought process around vision and whatever. But at the same time, from an executor perspective, it seems like all I was dealing with is problems. And
12:49
some of that can be handled with delegation and good managers and, you know, I think to a large extent that somewhat happened in a couple of different roles, um, couple that you and I are involved in. But, um,
13:03
o- o- overall, I mean, I don't look at... I certainly don't get, uh, concerned when problems arise. I kinda look at it, that is the work. It's why it's called a job. If, if all we were ever working on was,
13:18
uh, you know, sort of the next new thing and there were never problems, well, these companies wouldn't need dozens or 50 or 100 people, right?
13:28
I mean, that's the whole point is that everything's always going to break at some point. There's, uh, there's some level of breakage that's always gonna happen.
13:40
And so to me, that becomes part of the challenge of just, hey, w- w- we wanna build this product, but we also know there's always this built-in distraction of go-to-market problems or system breakage or whatever, regulatory compliance, whatever it is.
13:57
And so I wouldn't say that I necessarily love it as much as I've just embraced the fact that that's the way the world works, that Murphy shows up in every environment, and it's kind of a truism in my life.
14:10
He just likes to show up and in inopportune times. And so the reality is, while you're really, really focused on doing something, there's always gonna be some distraction.
14:20
And so, I don't know, to some extent, maybe I embrace the distraction a little bit, um, too much because the reality is it does inhibit growth and it, it inhibits focus.
14:34
Um, you know, and there's, there's people that I respect that will tell you just hyper, hyper-focus on the two or three things that matter and only look at those things and be able to shut all of the other stuff out.
14:46
Uh, that's great as a, you know, sort of a motto and, you know, I, I haven't lived my life that way. Maybe it would be better if I did. I don't know. I do think you're pretty...
14:58
Just in terms of people I've worked with, like, I consider you very intentional. Like, when you're in a room or when you're on a call, like,
15:04
there's a-- there's never a question that you-- I have your attention and, and, you know, like vice versa. Like, whether you're playing with your sunglasses case or what, like, you're just always, like, really in it.
15:15
Um, and I've always appreciated that about you.
15:17
I'm curious how, how you stick with that and how you always, with all the stuff and all the distractions and all the problems, how do you maintain that ability to, like, stay really intentional in the moments?
15:29
Yeah, it k- kind of goes back to the thing I started with, which is I, I think I do get kind of the hyper-focus kind of person. Um,
15:40
and oddly enough, I'm actually pretty protective of my time, uh, just 'cause I think that's one of the only things I can provide is time.
15:48
And so I kinda look at it as if, if I've given you the time or you've given me the time, then I'm gonna try to focus on that period of time and, um, and listen.
15:58
I've just learned over the years, like I-- That intentional part is probably more me listening than talking. I feel like if I'm talking, it's either 'cause I've been prompted
16:10
or I feel like I have something that needs to be said at least now. Um, but I, I try my best to listen more than I speak, and I tend to learn better that way than, like, hearing myself speak. Um,
16:26
it, you're-- I mean, it's very kind that you think I'm intentional. Um, I, I think... I'm not sure I would characterize myself that way.
16:33
Um, maybe focused, but I also don't like wasting time, um, particularly your, you know, your time or somebody else's time. I just feel like time's a valuable commodity. I know we got a, we got a couple of minutes left.
16:48
I'm curious, if you set aside the fintech, set aside payments, what kind of stuff are you spending more time thinking about or getting excited about- Hmm...
16:58
that k- kind of falls outside your typical bounds of what your working days look like? This may not age well, uh- [chuckles]...
17:05
but the, the reality is, like, I, I, I am concerned about some of the global stuff going on, just the geopolitical and so, um... But I also, maybe this goes back to the, what you were bringing up.
17:18
I, I, I look at things and I tend to not get super excited or, or I, I'm not easily excited about things that are kind of out of my control. But I do view them in a lens of i- interest from a learning perspective.
17:33
So you, you think about, um, what we've got going on in the Middle East, and, you know, I could take a political bent on one or the other sides or three, you know, however, however many sides are on.
17:44
But that to me is boring. Um, whatever. But what I am interested in is downstream collateral effects of the things that are occurring. And this sense,
17:58
I think that there's kinda two, two kinds of people, and that's probably inappropriate to say there's only two kinds of people, but I just find there's two kinds of people.
18:06
There's one side of the people that are like, "This stuff always happens. It's gonna be fine. We may have some intermittent blips and blah, blah, blah." And surely they thought of X, Y, and Z.
18:17
And then I think there's, there's the other group which is, uh, maybe more prone to, uh, fatalistic thought processes and, you know, catastroph- how do we say that word? Catastrophizing everything. Um,
18:32
I swing back and forth, by the way, uh, so I was... I'm not, I'm not making any, you know, character, uh, determinations on that.
18:38
But I am interested in like, what does the economy do in the next 12 months, and what factor- what effect does that have on me?
18:46
You know, my- I've got two college kids that just graduated and have jobs, you know, what is that gonna do to their job, job process? And, and ultimately,
18:55
what does life look like if we move into a hyperinflationary environment? Um, if there really are food shortages and things that, that in my lifetime I've never really felt the pain of. Frankly, I haven't.
19:09
Um, my parents felt a little of that pain, at least initially early in my life and my brothers' lives, but I've never known that. I've never had to wait in line for gasoline. I've never...
19:20
You know, we had food shortages and some things during COVID, but man, toilet paper's different than I can't get potatoes, you know, or whatever. And so
19:30
I am interested to see how that plays out and the sort of global ramifications, that there's no way somebody built an effective enough model to think through what's happening there. And so, um,
19:48
I think for me, I'm trying to determine like, how does that play into what I'm gonna do the next 10 years of my life, and is this a inflection point for some new thing? Um, and so for me, it's more of a
20:04
case study or something that I can spend time kinda going over in my brain and reprocessing, um, hopefully without getting hysterical about it, which I think is the key. Uh, I don't wanna do that. Who are like...
20:17
Who are people that are doing interesting things? Who are you following? Who are you paying attention to? Are you doing it? Like, what's giving you energy personally?
20:23
What are you working on, um, that kinda pulls you forward each day? Yeah.
20:30
I think for me it's, um, I spend a lot of time in the angel investing network stuff, and which is always awesome for me because, you know, one, there's a, there's a heavy, heavy hit rate. Um,
20:44
uh, well, it's a failure rate, but I get to see an awful lot of stuff out there, and that stuff is really, really compelling.
20:53
Um, and so anything from medical device to consumer to things that I just don't get a lot of feel for, and so able to see that, um, I am...
21:04
You know, and, and that tends to be a younger crowd that's doing that, which helps me because I kinda wanna see how they think about problems and how they think about problem-solving and, and that kind of excites me just to kind of watch that evolution and staying plugged into that.
21:21
And, um, I mean, sports is always a thing in my life. It'll always be a thing in my life, kind of embrace at times or whatever.
21:29
But, um, and so I'm, I'm, I'm genuinely interested in like what happens in a new sport environment.
21:35
You know, your, your son's about to go off into that too, and NIL, all these other things, and I, I view them kind of like these geopolitical things. I'm really curious to see how life operates. You know, it
21:46
seems like semi-professional or professional, maybe it's just full-on professional sports at this point. Um, and so I, I like watching that evolution just to see...
21:56
And, and maybe there's opportunities there too, um, from a technology perspective, I'm not sure. Any f- any final like thoughts,
22:04
recollections about like a time in your life where you, like you really came up against it, where you thought you might be looking at yanking the rip cord, but you powered through something, or you just, you took one more step and it was enough to keep going?
22:18
For me, the I- the one thing I would lean on is just my place in the world, and that it's a very small place in this world, and so, you know, um, how much can I control?
22:31
Uh, can I operate or lead or follow with integrity and with patience and compassion and kindness? And you know, that i- this isn't that big of a deal in the grand scheme of things.
22:43
And I, I struggle with like overall fulfillment in jobs, period. I mean, you're in FinTech and payments, who cares? At the end of the day, it's like I don't know that I'm advancing anything, uh, from that perspective.
22:57
I mean, I put food on the table, whatever, but, um, it's just not that important. And certainly, there are people in this world that are working on things that are tremendously important. Um, I'm not one of them.
23:10
I'm not doing brain surgery.
23:13
Uh, so I have to put everything into those little buckets so I can understand priorities and, hey, I'm gonna work as hard as I can on this problem, but ultimately, if the problem consumes me, it consumes me. You know?
23:25
And I guess part of that, even though it feels like it may be detached from something greater, is like it's how people like you and I get to meet each other, you know? Working on these big problems that seem really
23:37
outside of [chuckles] what we're interested in at our core, but like it still leads to relationships, working, creativeness, all that kind of stuff. So- Amen. Amen. Thanks, man. I appreciate you doing this with me.
23:49
It's good to see you. You bet. Yeah, it's great to see you, man. Take care, bud. [outro music]
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