238: Why Curiosity Makes Better Leaders and Businesses
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Curiosity can change the way we lead, work, and grow. In this episode of The Richer Geek, operations professional and entrepreneur Jon Bassford shares how curiosity shaped his career and why it’s the key to building stronger teams, smarter businesses, and better results.
In this episode, we chat about…
How Jon went from law school to operations leadership.
What it means to be a curious leader.
The three shifts leaders need: mindset, operations, and culture.
Google’s study on psychological safety and why it matters.
Stories from Steve Jobs and Jeff Bezos that show the impact of curiosity.
Why founders should hire outside their strengths instead of trying to do it all.
How curiosity shows up in both business and co-parenting.
Key Takeaways:
Curiosity helps leaders move past habits and try new approaches.
A culture of curiosity starts with making people feel safe to speak up.
Leaders need to ask questions and not settle for “this is how it’s done.”
Founders often waste time by hiring in their strengths instead of their gaps.
Delegating low-value tasks saves energy for the work that matters most.
Curiosity is not just for business, it can also improve family and personal life.
Resources from Jon
LinkedIn | jonbassford.com | Lateral Solutions
Grab your free chapter of The Curious Leader by texting “chapter” to 33777
Resources from Mike and Nichole
+ Read the transcript
Mike: Hey everybody. Welcome back to another episode of the Richer Geek Podcast. Today we have Jon Bassford. He's an operations professional entrepreneur, and he's driven by his Curiosity! Curiosity is his superpower, and it's driven his personal and professional advancement. After law school, Jon put this curiosity to work, launching, managing, improving operations for venture backed startups to global nonprofits.
How are you doing, Jon?
Jon: Great. Thanks for having me.
Mike: Absolutely. So it's two things. Curiosity can either kill the cat or it can, make you advance and make you just, you know? Open up your eyes. So before we get started on the curiosity-driven leadership, give us a little bit about your background and how in the world did all of a sudden just start like, "You know what? Let's start a business around curiosity."
Jon: Sure. So, I was born and raised in the Midwest. Decatur, Illinois was born and raised. I spent the majority of my time there. I went to law school in Ohio. I actually went to Washington, DC on a family vacation in high school, and I just fell in love with the DC Metro area.
And I spent a semester here in college, said, fell more in love with it and said, I'm gonna move there one day. After law school, I got a job offer in Baltimore. I'm like, close enough. So I was up there for about six years and been down here in the DC metro area for about 14.
I'm in Maryland, just literally right outside the beltway.
After law school, to be honest with you, I did not know what I wanted to do with my career. I wasn't quite sure I wanted to practice law and I fell into working for a legal organization I was a member of in law school.
And so it kind of launched initially a career in nonprofit association management. But actually it was a real blessing for me in the sense that working for a small organization, I got to have my hands on a lot of different things and really have a direct impact. My first year as a professional, I'm sitting in boardrooms.
I'm talking about governance. I'm talking about really high level things early on in my career, and that really allowed me to get this general knowledge of operations. And so I, when I switched to my next job, I kind of outgrew the organization a little bit and wanted to go a little higher.
I actually started working for another trade association, but it was a startup that worked with startups. So I kinda had this double immersion into the startup world and really working on operation from a startup phase really allows you to really focus on efficiency and effectiveness and doing it.
We always hear the phrase, "If you had to start all over from scratch, what would you do?" If you didn't have, you know, everything that already existed and could just start from scratch. And I've had the ability to do that throughout my career and just really learned that my jack-of-all-trades nature really lends itself to an operational career.
Mike: Yeah. And thank God that you're able to create, you know, find that, 'cause so many people are just spinning their wheels, right? And they're just like, what if, you know, I wish I'd have done this. And it's always nice when people sit there and say, "You know what? I kind of found the niche and it's actually fun."
Jon: Yeah.
Mike: Yeah.
Jon: I'm a big believer in that, you know, kind of purpose. I think it's over, over verbalized sometimes as this esoteric thing that we need to find and have to search for and I think it's just finding what you're good at, finding what you enjoy doing.
Find a way to monetize it and just get to work.
Mike: Yeah. If I could monetize what I'd love to do, that'd be great. But, you know, most of the time it's like going, "Hey, I'd love to do this and there's no way I could monetize it or make work." Then it becomes a hobby.
That's the big difference between, maybe you can expand on that. It's like people are listening. It's like, "Oh, well I love macrame," you know, but so there's this difference between hobbies and doing what you love, but can you monetize it, right?
Jon: Yeah.
In some sense there's people out there monetizing all kinds of crazy things these days.
It's gotta be a service or a product that people want, right?
If you are, you know, love making weaving baskets, but you can only turn out one per month, yet you're not gonna make your career off of it, right? But maybe if you love weave basket making, and you can find a system that can crank out $200 a month.
Then maybe it can become a business, right? So it's all about, just finding that right secret sauce where your skills lie, what you enjoy doing, and then being creative, being curious about how we can scale this?
Mike: So let's talk about, you know, what we're here for.
So, I know a lot of leaders and a lot of 'em aren't curious. There's some other things, you know, so give us a breakdown of what exactly is a curious leader. What is that definition?
Jon: Let me first talk about why it's important to be a curious leader?
And that's 'cause you know, our organizations are run by people and so they fall into the same patterns that we as humans fall into. And, you know, biologically, evolutionary, neurologically, whatever term you want to use, we are ingrained to have fear to keep us safe. To form habits, to form bias.
If we didn't have habits, you know, if you read the book, Power of Habit, if we didn't have habits, we'd literally be paralyzed with thought. Just how to take a step, how to turn a doorknob, just every single thing that we do without thinking about it. 'cause we formed habits, we'd be paralyzed by thought.
So all of these things are natural occurrences in humans and necessary for survival and help us get to this point in humanity. But when it comes to innovation, growth, and change. They're the enemy. And that's where curiosity comes into play. Curiosity is about having that intentional and inquisitive thinking that helps you look beyond your current situations and your own limitations to explore the possible.
Mike: Because you look at one of the two or three things that we're born with. And one is curiosity.
You're changing things. I mean, you're, It's all that, and at some point we lose that and a lot of it is, you know, maybe fear or maybe that we're just kind of our environment.
We're just getting to the point where, well, this is just how it is now.
And we no longer learn or we're no longer curious because of that.
Jon: Yeah, there's a stat that's been floating around for a while. I think Joe Dispenza, if you know who he is, coined it, but I think it's something like, by the time we are 35, either 85% or 95% of our actions and thoughts are completely programmed.
We don't think about it. We just do it. It's just ingrained in us and that's what we do. And seeing curiosity being intentional about curiosity is a way to break free from that and break away from those habits to truly challenge yourself to think and do differently.
Mike: Yeah. 'cause a lot of times we're, especially in our influential years. We listen to a professor, we listen to bosses, we listen to friends or coworkers, and all of a sudden we just become, "Well, this must be it."
And we no longer even fact check. We no longer even are curious about what the truth is.
It's just like, "Well, this is what my teacher said, or this is what this person said, so therefore it must be true. And I don't even,"
and you look at us today, I mean there's no curiosity, there's no, it's "This way, my way or no way." And people have just become very inflexible.
So how do you become that curious leader?
If you talked a little bit about what it is.
I own my own company. I'm a leader. How can I get back to being a curious leader?
Jon: So being a curious leader in my opinion, and I wrote about in the book, The Curious Leader.
If anyone is interested in a free copy of the first chapter, PDF, they can actually text “chapter” to 33777 and we'll email you the first chapter via PDF. But I talk about, in the book, three shifts that are required. What is mindset? Which is moving from a fixed mindset to a growth mindset.
And that's just simple thinking, right? It's just just getting out of your own way and realizing, getting away from the notion of like, this is just how it is. This is the way things will always be. Just keep the status quo going versus what can we do differently? How can we explore?
How can we change? So that's, you know, just mental, right?
Then we shift into operational excellence, which is looking at how our organization can be managed to achieve the intended results. As efficiently and effectively as possible.
And the last shift is, unless you're the lead singer of a one person band, you gotta bring the team along with you, right?
And so you gotta create a curious culture, which allows for that kinda creativity to flow throughout the entire environment. So those are the really three shifts that are required in my mind to become a curious leader. And it all starts with just your thinking. Just changing the way you're thinking and stepping outside the box. Some tactics and steps for that or asking questions. Challenging the status quo. Making sure that nothing is just, we're doing it because that's what we do and how we do it.
Mike: Yeah.
Jon: But really learning to just dive in everything and say, is this the best way? Is this the best process?
What can we do to change this to make it better?
Mike: How hard do you think it is for leaders? 'cause you know, I see a lot of leaders are just like going, you know, "I'm the boss. It's my way, the highway."
How hard is it to make that switch? I mean, you gotta like, you know, bop 'em upside the head and say, look, you know, there's a reason why no one wants to work for you.
Jon: Yeah. It's a tough one. And I actually, I, I talk about this in my TEDx talk . On the DIY Dilemma and how curiosity gets away from that and sometimes it takes leaders kind of hitting rock bottom a little bit to shake loose, right? Because they have this mentality that ideas have to come from and through me only.
And then constantly question their staff why they keep getting the same results.
And that's why the people don't wanna work for him. 'cause I mean, I literally have had a CEO that I worked for who was famous for asking the staff the organization was founded the same year as Amazon.
"Why aren't we Amazon?" But he also put his guard up about making changes in how the organization operated. Even things like adopting video content for a younger generation, which is king, right?
And his response to me was that's not how I envisioned this organization operating when I started it 27 years ago.
You mean before YouTube, before TikTok, before Instagram, you did not envision video being a mechanism of content and education?
So sometimes you do have to help them get outta their own way and just see it. You do it through data, you do it through inspiration but sometimes that is the hardest part.
Mike: And yeah, I agree with that. And also that affects culture, right? So talk to us about, you know, it's in order to grow, with my employees at the different hotels, it's like, welcome to the family, welcome to, I want them to feel part of a culture.
And that kind of goes right along with it.
There are people with that the culture, you can tell. It's like everyone's miserable. Yeah, you can usually trace it up to that leader, right?
Jon: Yeah, absolutely. I mean, cultures formed whether you want them to, are trying to or not. And it's usually when you don't dictate what it is, it's usually one you don't want.
And you're absolutely right. Culture has to be led from the top.
I've worked in places where leaders thought they were creating this most innovative, results-oriented culture and what they created because of their attitude, their mechanism of leadership, was teaching employees to keep their head down, do as little as possible, and that was the best way to not put your neck out there and be fired.
So curious leadership or curious culture is about bringing everyone, like you said, making it feel like a family, creating an atmosphere where people can exchange ideas, give feedback without fear of arisal and being fired. It actually, the backbone of curious leadership or curious culture, is rooted in a study that Google did.
Google did a study called Project Aristotle. They were trying to define what made 18 successful degrees, experience diversity, whatever it was. And what they came back with was psychological safety. And it was creating that environment where people felt secure and safe to speak up, speak out.
Instead of living in that nature where everyone just sees the problem and ignores it because they don't want to be the tattletale, they don't wanna be the one who tells the boss that their process, their procedure they put in place five years ago is no longer working. That curious culture allows that to happen and allows things to almost work.
Kinda like what the way agile development works, for software, right? Where you're constantly reiterating and solving problems as you go along through the operation.
Mike: Yes. We've kind of talked about companies already in existence, leadership and things like that. I've worked for someone, I wanna start my own gig.
Create a startup, what are the elements that I have to know beforehand in order to launch successfully into this type of realm of new type of leadership?
Jon: Yeah, so obviously there are some logistical things that you gotta do. Like if you wanna form a company, you gotta LSC, whatever it may be.
You gotta incorporate, you gotta get your AA in. Yeah, bank account, gotta get your insurance, you gotta make sure the risk management piece is there.
There's really kind of, about seven to ten things that you really gotta make sure in place to have a true functioning business.
And I think where a lot of people go wrong is not being strategic about their operational systems early on to create systems that are efficient and effective. It's kind of an afterthought. They just add piece by piece as they think they need it.
But I really encourage people to be strategic about how you're setting it up and what systems you're using.
And another thing that I often see with founders is they tend to outsource or higher up in areas of their own genius first. And not the areas where they're not.
Mike: That's interesting.
Jon: If you're a sales person, you're a product person, you're a developer, whatever it is, they'll go out and hire salespeople.
They'll go out and hire marketers, they'll go out and hire developers, but they don't hire a bookkeeper. They don't hire an operations manager. So what happens is that the founder gets sucked down into these areas that really aren't worth their time for the cost of what their hourly wages should be worth.
And it's also an area where they're not overly proficient and it causes a lot of stagnation in their growth.
Mike: Oh, yeah. I'm guilty of that.
I worked in my business for so long and finally I'm like going, I hate accounting. I hate bookkeeping. Why am I paying the bills?
And it wasn't until I delegated and, you know, I went through some coaching also, and they talked about finding your unique ability. What are you good at?
And then only do that thing and then you delegate because there's someone else that's an expert, unique ability in bookkeeping, operations, sales, marketing.
And I don't like any of that.
Jon: Yeah. I always encourage people to ask kind of questions, right? What am I good at? What do I like doing? And what is worth my time to do? You should have a thought in your head of, if I were just a, you know, working for myself and I was billing out my time hourly.
Whatever I wanna make per year, divide by 20/80, which is what a 40 hour work week is, right? Over the years, find out what it is you wanna be making and if usually for an entrepreneur, that's probably gonna be somewhere between $150 to $300 an hour.
When you're starting out consultants, that's kind of a going rate.
Then why are you doing the $30 an hour bookkeeping job?
You're devaluing your worth by using your time in these tasks.
Mike: Yep. And you know, there's different ways. I mean, I started out with VAs. It's like, hey, I mean, not be able to afford $30, $35, $40, you know, an hour, $50,000 a year but you can find there are other ways there.
There are no longer really excuses, you know, is there just like, well, I can't afford to get in help. It's like, eh, you know what, you can.
Jon: You use sites like Upwork, right? Even a project base, right? Like a lot of times people, another problem, a lot of owners will make, founders will make is they ramp up hiring full-time people for part-time jobs and that tends to be when they get in trouble.
Use sites like Upwork, find consultants, work with people on a fractional basis until you have the recurring revenue to justify and the time needed from these individuals to justify full-time roles.
Mike: Yeah. And that's great advice. Absolutely wonderful advice. There are so many platforms. You know, when I got started, I called PG Days, which is Pre-Google days.
That's when I started my business. So I had excuses, ladies and gentlemen, for those 'cause small town Indiana. I'm like going, I don't know how to do anything, you know? It's yellow pages, flip to the yellow pages, how they do something. I mean, I don't know. But nowadays it's like listening to everyone.
You have people like Jon, you have his website, his expertise, his information. There are no excuses anymore. The only excuse is right here inside your own head, you know? If you don't believe you can do it, you're not gonna believe it. You're not gonna do it.
You know, we talked a little bit about The Curious Leader.
Are there any other things inside of that book that you'd like to share with our audience?
Jon: That's really the main thought, is the book to highlight some of it for you guys is, I dive into my own personal experience from consulting, my real life example as I came across. But I also tap into stories and the big names, right?
Talk about Steve Jobs. There's a great story about when he was being brought prototypes. Again, think about challenging the status quo and asking questions and looking at things differently. People kept bringing him prototypes with a physical keyboard at the bottom of the phone.
And because that's what we had. We had blackberries, we had, you know, Nokia and all that type of stuff.
And he dared to ask the question. Why does it have to have a physical keyboard? And that's what revolutionized the phone into the iPhone and what we all do now. Yeah, obviously there's some that have the flip and all that type coming back, but just stories like that, that truly showcase, you know?
How just little thinking, asking questions can do it. If we have time, I'll do another quick story.
It's from Bezos. I love this story. You know, Bezos, took a bookstore to an international marketplace to the largest storage company for data. The developers use it all around the world.
Manufacturing got changed, not manufacturing, but supply chains got changed because of how he did it, but he contributed an employee early on with the greatest idea that helped change Amazon. This was when he was just working in his basement, in his garage, had a handful of employees and it was all hands on deck, boxing up books, and they're all on the ground and they're all aching about how their knees hurt.
And Jeff's like, "Man, we really need to get knee pads."
And the employee goes, "No, we need a packing table."
He went out, bought a couple of packing tables, got off their knees, they increased, they doubled their production within a month. And so that's the single biggest idea that helped propel Amazon because he was looking at the wrong problem.
The problem wasn't that their knees hurt, the problem is that they were on their knees and she thought to say, "Hey look, this is the real problem. Let's fix that."
And it made all the difference.
Mike: Wow. Absolutely. Wonderful.
I know you have another book, The Co-Parenting Secret.
Is there anything else that you'd like to share before we finish up today?
Jon: Yeah, I can talk briefly about the Co-Parenting book. I'm hoping that comes out here in the next three or four months, mid to late summer of 2025 here.
But really that's much more of a personal project.
After I got divorced with my ex-wife, I kept having people, family, friends, say, "Hey, what's it like parenting with, with your ex-wife?"
And I was like. "Great. Like we could write a book on co-parenting."
So about a year and a half ago I said, I'm gonna stop just talking about that and actually do it. And it really, again, kind of thinking about curiosity and challenging the status quo. I was a product of divorce growing up in the 80s.
I had a typical arrangement where I lived with mom and stepdad. My dad saw us every other weekend.
My mom had all the real responsibility of sickness and homework and all that type of stuff, and dad got to be the fun dad on the weekends. But now things are changing, right? Both parents are more engaged in a daily process of the kids' lives.
And it's really kind of just challenging to look, again, look beyond that status quo of how things used to be done and what are the best practices to truly bring about co-parenting in a different way. And the secret for me, which is the subtitle of the book, is it's not about You. It's not about selling old scores, it's not about your ego.
It's not about, you know, are you getting all the right time? It's about the kid or the kids and what they need first and foremost. And then looking at the nucleus, looking at the whole, whole group. My ex-wife and her parents and her uncles were at my wedding, to my current wife. We still, you know, I talk to my ex-wife on a daily basis.
Usually about the kid. But we were intentional about creating, staying together as a family even though we weren't divorced and it's really made Yeah. A major, major difference in how my son sees the world.
Mike: Well, absolutely. Yeah. You know, I can go back. Yes. This is much better than probably what we went through.
And good for you. It is hard, you know? 'cause sometimes divorce is not it can be a little sticky, you know, and to actually fight through that thing of, you know, it's not about me. It's not about her. It's about us together and forming something strong from when our child grows up, you know, that there's an environment that's productive.
How can people find you, Jon?
Jon: Yeah. Best of ways for the consulting side, go to think-lateral.com. And on my kind of personal brand side, they can go to jonbassford.com, J-O-N, B-A-S-S, like a fish, like a car dot com. And those are the two best ways to get hold of me.
Mike: All right, Jon. Well, I appreciate you coming on The Richer Geek Podcast.
I hope you have a wonderful day.
Jon: Thank you. Thanks for having me.
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ABOUT JON BASSFORD
Jon Bassford is an operations professional and entrepreneur driven by his curiosity. Curiosity is his superpower, and it has fueled both his personal and professional growth.
After law school, Jon put this curiosity to work, launching, managing, and improving operations for everything from venture-backed startups to global nonprofits with impact. For Jon, there is nothing that curiosity can’t help.
Today, he is known for his curiosity-driven leadership, helping organizations and individuals innovate, change, and grow by adopting curiosity as their own superpower.