096: $2 Billion Business Blueprint: Bootstrapping Kajabi With Jonathan Cronstedt

In this episode, we sit down with the digital titan, Jonathan “JCron” Cronstedt.

With over 20 years at the helm of executive leadership, JCron has been instrumental in the meteoric rise of ventures like Kajabi.com, helping to bootstrap the brand all the way to a $2 Billion Dollar Valuation.

Dive deep as we discuss:

• Embracing change in the tumultuous digital age.

• The influence of industry stalwarts like Joe Polish on JCron’s career.

• Key strategies that have been game-changers in the SaaS world.

• The significance of personal growth, mentorship, and taking calculated business risks.

Beyond his illustrious career, JCron is a beacon for future entrepreneurs as the CEO of The Jonathan and Nicole Cronstedt Foundation. From business insights to life lessons, this conversation promises a treasure trove of wisdom.

Inspiring Quotes

• “The quality of service in the US has eroded significantly.”

•  “One of the hardest parts and one of the most difficult truths of companies, the vast majority of companies are terrible at talent development.”

• The Importance of Standing Out
• Personal Accountability in Relationships
• The Decline of Service Standards
• The Enshrinement of the Highlight Reel and the Loss of Appreciation for Effort and Work Ethic
• Birthdays and Mentors
• From Bankruptcy to Business Success
• Taking Risks and Embracing Opportunities
• The Importance of Pivoting in Your Career
• Short Tenure and Hiring Concerns
• The Importance of Commitment and Family Business
• Seeking Knowledge and Expertise
• Tequila Preferences and Board Membership Challenges
• The Role of a Board vs. an Operator
• Defining Identity and Transitioning after Exiting a Company
• The Decompression Process and Overinvestment
• Delegation vs Abdication
• Free Course and Beyond a Million YouTube Channel Launch.

Brad Weimert (04:15.554)
J.Cron, it is awesome to see you. I wish it was in person, but I will, I’ll take remote when I have to.

JCron (04:21.558)
Dude, I wish it was in person as well. I’m very much one of those people that I think virtual and Zoom and all of that stuff just needs to die. I miss all of the IRL as the kids nowadays say. That was my jam. I was great IRL.

Brad Weimert (04:38.402)
Yep. You know, everything has transitioned in the era of Zoom, digital text, etc. The way that you communicate has changed the way that in fact, we don’t even have the acceptable protocol, like different eras, right? Different generations have different criteria for what acceptable text messaging is right or acceptable calling is. It’s not across the board. It’s irritating as hell.

JCron (05:05.674)
Well, I mean, there’s no doubt about it too. Like if there was something I was going to rail against generationally and like as the first birth year of the millennial, which means I qualify as what’s called a geriatric millennial, the thing that millennials do that just upsets the shit out of me is this idea that it’s socially okay to ignore emails. That like emails have been bucketed into this communication modality of.

If I don’t want to respond to you, I’m not required. And I don’t mean like LinkedIn spam. Do you have got a 15 minute meeting requests? I’m talking like there’s a boss employee relationship and it’s just like, I just didn’t think I needed to respond to that. It’s like, but I thought it was important enough to send to you. What gave you the idea that you didn’t need to respond to? Oh, well, if it was important, you should have slacked me or texted me. No.

false. Like, that’s not how this works. Like, you don’t get to tell me how I’m going to engage with you. And then they look at you like you’ve got an arm growing out of your forehead, you’re an idiot and should go retire. So I mean, that’s what I did. I retired. I’m out.

Brad Weimert (06:09.438)
I love it. I love it. Yeah. Well, these are I had a I had a friend years ago. I’m not going to tell this whole story. But basically, I was upset with somebody in my life. And because he was perpetually late, maybe I’m going to tell the story. He was late all the time. And like, I don’t mean a little late. I mean, like, an hour late, or an hour and a half.

JCron (06:29.562)
Like, late enough, like, why are we even still meeting? Because now I’ve had to cancel three other things to accommodate you being late, late? Yeah, no, I get it.

Brad Weimert (06:37.506)
Yes, and two things that he invited me to, where I didn’t know anybody else. Like it was just bizarre. So I was bitching to another friend and my other friend Thomas said, well, have you told him that it bothers you? And I said, have I told him that it bothers me that he’s 90 minutes late to things that he invited me to where I know nobody? And Thomas said, yes. And I said, no, Thomas, I have not told him that explicitly. And he said, well then you’re not allowed to get upset. And I was like, ah, fuck, you know, you’re right.

JCron (06:58.774)
Hahaha!

Brad Weimert (07:07.767)
And he said…

JCron (07:08.038)
No, he’s half right. He’s half right because it gives everyone an opportunity to be off the hook. But like, if someone is punching you in the face, you shouldn’t have to say, it upsets me that you punched me in the face. Like, we all operate in a society that has generally accepted rules. And if you choose to flippantly ignore them, your bad behavior is not my responsibility.

Like, I’m sorry, it’s just not. Like, I mean, it’s one of those things that there’s now, and at Dan Kennedy, I was just out at his Not Dead Yet Tour in Cleveland, a guy that I always love, and he was talking about this idea that now millennials have come up with a term called time blindness, which is now this supposed made up condition where you’re just unaware of time, and that’s why you are late or whatever. And I’m just like, this is just insane. Like, like.

There’s so little personal accountability that now everything is somebody else’s fault. So no, you don’t have to tell someone that being 90 minutes late is inappropriate. Like that would be a friend that the second time it happened, I’m like, yeah, I’m just not scheduling anything with you ever again.

Brad Weimert (08:17.571)
Well.

Brad Weimert (08:23.486)
and that’s where we went with it, was Thomas said, and if you tell him and then he does it again, you still shouldn’t be upset with him, but then you can elect to not spend time with him anymore. And…

JCron (08:35.21)
Dan Kennedy’s phrase is earned entitlement. And what earned entitlement is, it is I have carefully curated my life based on the priorities and the hierarchy of the people I have in it. And if you are willing to break mine because of how important yours is, I have the right to just opt out. That’s it. I don’t need to be a part of it.

Brad Weimert (08:59.414)
Yep. Well, I totally agree with that. And I also like the idea of extreme clarity and ownership of, um, different expectations. And so kind of what you’re defining is a culture in this case of people that have created their own expectations and we do not share them. And so while you and I believe that is not part of the general understanding of how life is supposed to work. Uh,

If you don’t explicitly state it, then you’re just being pissed at somebody else about it. And right or wrong, that probably doesn’t serve.

JCron (09:33.986)
Well, and it’s one of those things that for all of the entrepreneurs that follow you, that are listening to this, that are investing their drive time, their walk time, their whatever time to improve themselves, improve their opportunities, give them more opportunities in life to go after. If you’re hearing anything out of Brad and I sounding like, okay, boomer, whatever, what you need to hear is that if you’re trying to create a limitless future for yourself, the ability to stand out.

has never been an easier standard to meet. Like today, I mean, here we have the most luxurious hotel chains in the world, unable to answer their phone, but yet your corner pizza store for a $19 pie will pick up the phone and take your order with a real live human being. Like this is a universe where if you’re just willing to go one slight step beyond where everybody else is.

you’ll win everything. Like a friend of mine, Josh, he was just at an event and he was talking to a woman, I mean, I think she was probably in her mid thirties or something about dating. And he’s like, well, what’s the dating world like today? And she’s like, literally, every guy only communicates via text and that’s it. And she’s like, I swear to you, if anybody my age picked up the phone and called me, end game, done. Like I’m ready to settle down because somebody actually picked up the phone. And it’s like.

Holy cow, like that is the standard today of like, if you just pick up the phone, it’s done. I mean, yeah, this is a topic I could spend our entire podcast. I have lots of opinions and religion about it.

Brad Weimert (11:09.33)
I see that and hear that. So for clarity, do you think that the quality of service in the US or business in general has eroded significantly?

JCron (11:21.674)
Utter dog shit. Like, I mean, there’s not even a standard to point to anymore. Like, you look at an environment where other countries still view the idea of surprise and delight in a service capacity as a sustainable advantage and a moat that can be built and valued. In the United States, we are desperately trying.

Brad Weimert (11:23.662)
Hehehe

JCron (11:50.35)
to get rid of every aspect of going above and beyond in any capacity. And it’s why entry level jobs will be replaced by robots, because robots don’t bitch, they show up on time, they don’t ever, you know, collectively bargain. Like we are going to become victims of our own view of how work works. And I think Elon Musk said it best when he talked about why he’s not supporting this work from home, you know, thing, because he’s like,

It literally is dividing society by creating a different class of people that somehow, because you can code, you’re held to a different standard than someone who’s in business development or someone who’s in a service capacity of some kind. And you could totally say like, oh, well, you know, I deserve to be able to do that. And maybe you do. But at the end of the day, this is still hastening this divide of there is no service, there is no interaction, there is no human component anymore.

it’s simply just screens. And so, yeah, I think that when you look at a service experience in the United States, even today when you go to some of the best restaurants or best hotels in the world, it’s unrecognizable. Like you watch a video of what a flight attendant was in the 1950s when my mom was flying for TWA versus your experience today, where as long as you don’t get yelled at, it’s a good flight, it’s a whole different deal.

Brad Weimert (13:12.018)
Yep. Yeah. Well, I generally agree with you on the service front. I had a experience at I’ll throw the brand under the bus at a Hyatt the other day. There was an event at a Hyatt. And I, I called and I said, Hey, do you have room service here? And they said, yeah. And I said, I said, Okay, can I can I talk to them? And they said, Yeah, I’ll transfer you to the restaurant. It rings over.

nobody picks up, I get an answering machine, so I call back and they say, oh, did nobody pick up? And I said, no. And they said, well, you could just download the app and order it on your phone. And I was like, or you could put somebody on the phone and I could just verbally tell them what I want. And they said, well, yeah, but they might not pick up. And I said, let’s try again, again to voicemail. And I call a third time.

JCron (13:56.59)
I’m gonna go.

JCron (14:00.154)
Yeah.

JCron (14:07.992)
Mm-hmm.

Brad Weimert (14:10.618)
And same conversation. And I was like, do you think maybe you could walk over there for me and just see if you could get somebody there to take the call? And she was like, yeah, I guess I could do that. What the fuck? You know, like literally it’s supposed to just be room service, it’s supposed to work. And I don’t know if that’s a product of, it’s a generational product or if it is a, you know, a post COVID product or.

JCron (14:27.254)
I agree.

Brad Weimert (14:39.606)
if it’s management eroding, but it’s…

JCron (14:41.982)
Oh, I can, I can absolutely tell you where I solely lay the blame. Um, I, I 100, 100 million percent blame social media, 100% blame social media. So like, let’s just say you’re that person, you’re sitting at the front desk at the hi-at and your manager says, okay, your job is to answer this phone at the front desk, make every guest feel welcome and have a memorable experience and do whatever you can to make their stay amazing. That’s the job. And then while you’re sitting at the desk.

Brad Weimert (14:46.31)
I think I know.

Brad Weimert (14:51.4)
Oh, interesting.

JCron (15:10.838)
you are endlessly scrolling Instagram about all of these people that are on private planes, driving exotic cars, staying in amazing hotels, dining at the finest restaurants, and you’re sitting here with some dude calling you demanding room service, and you’re just like, I don’t give a shit about any of this. My life is supposed to look like everybody else is on this screen, so I’m just gonna do the least amount possible because this job is dumb and I should be an influencer anyway.

Brad Weimert (15:13.882)
Hmph.

JCron (15:38.026)
Like, we have completely enshrined the highlight reel of everybody else, and we have completely lost the appreciation for effort, tenacity, and a work ethic. It’s just gone. Everybody wants it today, everybody wants it delivered, and everybody wants what everybody else has, whether you have to work for it or not.

Brad Weimert (16:00.346)
Well, the other thing that you brought up that is part and parcel with this, and I think they both play into this notion of short-term gain, contrary to the long-term vision, is collective bargaining, collective negotiating. And what I heard was union. And unions made a lot of sense in the early 1900s, perhaps, or maybe late 1800s. Unions today do a lot of damage. And they are frequently at odds with the longer term.

vision and goal of a company that is sustaining the staff and employees for short-term gain of the workers, for the union workers. The auto workers union in Detroit, which is where I came from Ann Arbor, destroyed the big three, because when the big three were hyper profitable, which is not recently, decades ago, the union pushed for tons of benefits.

high salaries, et cetera. And as those companies failed to be competitively profitable, they couldn’t sustain those salaries. But the unions were still there, and they destroyed the companies. And I think that the problem, again, is just misaligned instead of short-term versus long-term. But you’re highlighting it in different areas, and that’s scary.

JCron (17:18.358)
Well, and what’s interesting about it to me is so collective bargaining, I think, is a very interesting topic. And where I actually get the most frustrated about it is I.

JCron (17:35.986)
I would say that I have less of a problem with collective bargaining in private enterprise because you’re at least negotiating with something that can fail. So that there is a point where you have to recognize if you push it too far, you’re going to kill the very thing you’re trying to optimize and then you have nothing to point to. Where I have a huge issue with collective bargaining is at…

Brad Weimert (17:56.554)
You should recognize. Yes.

JCron (18:03.618)
state, local or government levels when you are negotiating with something that theoretically can’t go bankrupt or can’t fail. Like, I mean, when, when you look at the unfunded pension liabilities on governments throughout the United States, it is unfathomably gigantic. Like it is completely unsustainable, should have never existed. But when you have collective bargaining with somebody that has no profit standard, like there’s not.

There’s not a point at which you can break it. That’s where it gets problematic. It’s like, you know, everyone’s mad about our education system. Everyone’s mad about the vast majority of our infrastructure and things that are failing. And it’s like, we have nobody to blame but ourselves. Like, we did this. Like, we created this.

Brad Weimert (18:49.802)
Yep. I can’t argue with any of that. And for the sake of people that don’t give a shit, I want to talk about business with you because you have an interesting business background. And I didn’t really realize it until getting into poking around. I knew like, you’ve been around in sort of similar circles as me for many years. And I even more recent years.

JCron (19:15.446)
Yeah, we’re old now. It’s weird. I don’t know when it happened. Like I turned 42 tomorrow and I’m just like, I mean, I’m even listening to this now. It’s like this episode. I think I’ve become the angry old man. Like I think I’m one iteration away from like sitting outside and like with a hose, like get off my lawn kind of thing. Like it’s really close.

Brad Weimert (19:30.05)
Sounds like it.

Brad Weimert (19:37.046)
Well, I am 43 on Thursday. So I got a year and a day, but I did not realize we were so close.

JCron (19:43.422)
Wow, yeah, well, dude, you, me, and Ryan Moran, birthdays this week.

Brad Weimert (19:48.714)
When’s Ryan’s? 7th? 8th? What?!

JCron (19:50.254)
Ryan’s is today, mine is tomorrow, and yours is Thursday. So literally, we’ve got Tuesday, Wednesday, Thursday locked up. So the third, fourth, and fifth.

Brad Weimert (20:00.29)
That’s amazing. Well, that’s a good plug for the Ryan Moran episode that I did a few months back. He’s super entertaining, and I’ll have to text him later.

JCron (20:07.766)
that if any of your listening to this was the rise up is that the dude is unbelievably brilliant way more entertaining than i am probably less angry to sell you know i would i would do that

Brad Weimert (20:17.35)
angry at different things equally entertaining. So, okay, I, the reason that I didn’t realize the background is because the majority of the time that I’ve known you, you have been running Kajabi. And there’s this super interesting path across like, basically just a ton of OG marketer clients of easy pay to racks. And you kind of

JCron (20:19.628)
Hehehehehehe

Brad Weimert (20:45.93)
ran or heavily participated in a bunch of them. So why don’t we, I wanna talk about the path here because this is what I’ve got. Car sales, mortgages, and then a shitload of like internet marketing, direct response stuff. And now this big software company.

JCron (21:03.19)
Well, I’ll give you like the three minute, how did I get to here? Because it’s actually kind of a fun story and I think it’s fairly instructive for everybody listening is. So here I am, I moved to Southern California when I was starting high school. And coming from the Midwest, Northwest suburb of Chicago, if I saw an S-Class Mercedes, it may as well have been a spaceship. And then moving to Southern California, finding out that an S-Class is a Newport Beach Honda Accord, you all of a sudden are confronted with, oh my gosh, like I…

Brad Weimert (21:10.115)
Dig it.

JCron (21:32.914)
I’m gonna have to play at a very different level because this is a very different universe. So here I am, I’m in college. I meet my very first mentor, buddy of mine named Steve James, still friends to this day, 23 years later. Met him because I dropped a business card in the missing roof of his Diablo VT Roadster in a parking lot. And just wrote a note, sent it to him, and calls me up, and I literally called him once a week for eight weeks, and every time he blew me off.

And finally eighth call, he picks up and says, look, if I have lunch with you, will you just stop calling me? And I’m like, yes, of course. So, because I needed a mentor, I needed somebody that I’m like, okay, look, you’re driving a Lamborghini, you’ve clearly figured out some aspect of life that eludes me and maybe you’ll tell me about it if I buy you lunch. That was like my grand plan. So.

Brad Weimert (22:03.874)
Wait, why were you calling him? And why did you put a business card in his open roof?

Brad Weimert (22:20.169)
Awesome.

JCron (22:20.65)
We end up having lunch and he’s like, yeah, you know, I’ll, I’ll mentor you. I’ve mentored a couple of guys, uh, you know, over the course of my life. And it’s gone very, very well. So, you know, it seems like you’ll, you’ll do it, but he’s like, bottom line, you got to learn to sell. He’s like, sales is everything. It’s where it all starts. So he calls up the general manager of Fletcher Jones motorcars in Newport beach, and I interviewed for what was then a very unique concept of business development center, which is essentially a unified call center.

follow-up system for all phone, internet, and sales traffic for a dealership. So end up there having an unbelievable time, making great money while I’m in college, thinking I figured it all out. And I end up getting a guy that I’m telemarketing following up who came to the dealership. And I’m like, hey, you got to buy this car, got to buy this car. And he’s like, I don’t know what you do. And I don’t know what you make. But if you were doing what I’m doing, you’d make five times as much. And I’m like, you should take me to lunch. And so it turns out…

He was in the mortgage business. I didn’t know what a mortgage was, didn’t know anything about it, but it was 2004 at the time. And I was like, I could do mortgages. So, leave Fletcher Jones, go into mortgages, end up as VP of sales with probably 70 loan officers, a couple hundred thousand pieces of direct mail a week, printing money. Like it was unbelievable. Took all of my phone sales and scripting knowledge from the card dealership, put it into mortgages, massive success ensued. Like any smart guy.

heavily invested in 100% finance real estate because real estate never goes down. Then 08 happens, business is out of business, all the real estate’s underwater. I have no job and no income, everything goes back to the bank, file personal bankruptcy. I bought my parents a house that I then had to have them move out of because the house went back to the bank. One of those real character building seasons. And so coming out of it, I ordered Dan Kennedy’s whole enchilada info package because…

there were all these guys selling into the mortgage business with their sales systems. And that was my first exposure to direct response marketing. So first product I opened up 1995 mastermind recording, I hear Joe Polish on there and I’m like, this guy sounds amazing. He can teach me how to be a marketer. So I call up his office, say, Hey, I’d like to hire Joe to teach me how to be a marketer. They’re like, great. He’s $25,000 a day. And I’m like, well, I’m bankrupt, so I’ll give him $500 for five minutes. And if he doesn’t see any potential, then cool, we’re done.

JCron (24:42.83)
So Joe and I become fast friends and he basically says, hey dude, move out to Arizona. I have a one bedroom apartment built off of my office. I’ll teach you everything I know. So literally follow Joe around like a lost puppy dog for the next three months, meeting an unbelievable selection of marketers, captains of the universe, super, super fun. And then Joe’s like, well, what do you want to do next? I’m like, I want to learn the online side. So very similar approach, reach out to Matt Vesak in Atlanta, ask to hire him for consulting. Matt’s like, you know what? Why don’t you just move out here?

So I move out to Duluth, Georgia, spend six months following Matt around to every internet marketing event imaginable, get hired out of there by Chet Holmes when he was launching Business Breakthroughs, which then a year later sold to Tony Robbins, which is now Tony’s business mastery curriculum. Hired out of there by Mike Koenigs, spent a year and a half at Traffic Geyser learning product launches, doing local marketing with video syndication. Hired out of there by Bill Glazer coming full circle at GKIC after he sold the Silver of Partners.

Then went into independent product launch consulting, which is how I met Roland, Ryan, Perry, eventually leading to my CEO role at Digital Marketer for a year, where I also started consulting for Kajabi at the time. Kajabi let me go as a consultant to work with Frank Kern, which I still give Frank shit about today. Then spent two years in the world of MLM, a year at Success Magazine, and then the whole time was renting an office from Kajabi.

So then September of 2016 rolls around, success wanted me to move to Dallas. I wasn’t gonna move to Dallas. Kenny walks in on a Monday morning and says, hey dude, what’s new? And I’m like, I gotta figure out what I’m gonna do, not move into Dallas. And he’s like, well, we’ve grown, you’ve grown, we should probably figure out a way to, you know, take this thing to the moon because it’s easier than moving your shit out of the office. And that began. Kenny is the technical founder of Kajabi. So co-founder of Kajabi, coded everything.

Brad Weimert (26:28.506)
Who’s Kenny?

Brad Weimert (26:34.051)
There we go.

JCron (26:36.838)
over a year before launch and really was my partner in crime. He was the CEO, I was the president, up until July of 21 when we stepped out of operations. So my journey was July of 21, sorry, July of September of 16, six million ARR, 25 team members, July of 21, north of 100 million in ARR, 400 team members and a $2 billion valuation.

And Kenny and I stepped out of operations, moved to our board positions, and I’ve now been gainfully unemployed for the last, roughly two years.

Brad Weimert (27:13.998)
I have questions. First of all.

JCron (27:17.609)
I hope you do. I ran through my entire life story in three minutes or five or whatever it was.

Brad Weimert (27:18.938)
Hehehehehehe

Brad Weimert (27:24.206)
First of all, you sound kind of crazy. Living in random people’s garages and extra bedrooms and whatnot. Second, I have to highlight that you started that with the value of sales and learning how to sell and holy shit did that turn out to be true because not everybody is going to get Joe polished to take time for 500 bucks, first of all. And second,

get an invite into his home. So that has to be the foundation of selling.

JCron (27:58.338)
I still to this day probably once a quarter call Joe for no reason other than to just say thank you. That so often in many industries you don’t know how impactful the people you meet are until long after their impact has happened. And when I think of an industry where I could have met a variety of different…

mentors different people and to find somebody that literally would give me the ethical foundation and the view of what marketing can mean, I give Joe all the credit. Because to go from, I’ve never done anything with direct response to I’m selling tickets to the first super conference where Joe’s bringing in Richard Branson, beginning to exit from working with carpet cleaners to becoming

You know, one of the highest level networking mastermind groups, you know, Genius Network now is a gigantic brand. Being there at that beginning and getting to follow Joe around, like, you know, meeting, gosh, Dean Graziosi right after Motor Millions meeting Tim Ferris, you know, two weeks after the four hour work week book was first published and, and seeing him still traveling the world in his, you know, like three pound compression backpack and, you know,

Josh Bizzoni before BioTrust, you know, just after Bill Phillips with EAS. And it was, it was an unbelievable season. And like, you know, for everybody listening, it’s like, wow, that was a really cool adventure. I would say the themes that I would lean into are being willing to take those risks, being willing to ask how you can show up and be of value to somebody. And just being willing to say, I don’t know where this is going to go, but I know that if I focus on who I’m becoming in the process, it’s going to work out.

And that’s been my story the entire way. Because there’s no doubt about it. I’ve been in places and been in rooms that I had no business being in, simply because nobody told me I didn’t belong there. I just was like, oh, cool, I should be here.

Brad Weimert (29:55.23)
So there are, I’ll call it, two different camps of people that are probably listening. You’ve got the people that are fledgling entrepreneurs that are trying to kind of forge their path, and then you have established people that are looking at tactics and strategies to grow once they are beyond a million. I think that there are different lessons for each of them, so I wanna ask you a couple questions. The first, I wanna highlight everything you just said for the fledgling entrepreneurs.

Because you jumped, and this is the question along that, you jumped from roll to roll to roll for several years, seemingly opportunistically. Your narrative was take risk, basically, was go after the opportunity, don’t miss it, just show up in the room and see how it goes. And you gave us a couple examples of that.

Are there any regrets through that path? Do you feel like you didn’t stick around and get all the lessons you could have out of any of those stops along the way?

JCron (30:59.546)
say regrets because I think regrets would indicate that I’m not happy with how things have turned out. I feel unbelievably blessed. I tell everybody that God watches out for fools and little children and I consider myself half of each. It’s been an amazing, amazing journey. What I would say outside of regrets is I would say I have come to have a greater appreciation for the alternative paths that may have happened.

So let me explain. So if we go back to that moment in the mortgage business where I filed bankruptcy and I decided that I needed to reinvent myself in the world of digital marketing, because that was my path to a new career, there were other ways that could have gone. And so some of my friends that were a little bit more mature, a little bit more experienced, they didn’t just.

shut down the company because they had a whole bunch of unbelievable phone sales people in a room that needed something to sell. They had the wisdom to pivot. So where I said mortgage business is done, I got to go find something else. And what I learned is it takes you about a decade to be good at anything. So right around my decade mark is when things connected up. But the other people that did really well, they didn’t leave the mortgage business.

Brad Weimert (32:11.854)
Hmm

JCron (32:18.358)
they transitioned from mortgages into loan modifications. And then when loan modifications had different legislation, they transitioned into debt settlement. And then debt settlement had different legislation, but by the time debt settlement was beginning to wax and wane, all of a sudden the A-Paper refi market boomed. And so the guys that stayed, the guys that struggled, the guys that pivoted, they were the only game in town when the market started to come back and they just succeeded massively.

because they sort of stayed where they were planted. So there’s definitely a lot of opportunity there. I think for me, I had just not seen enough of the mortgage business to know what could be done. I was like, yeah, I was in the mortgage business, it didn’t work, I’m gonna go do something else. Whereas a lot of people were, here’s how my resources of a room full of trained salespeople.

Brad Weimert (33:07.802)
Mm-hmm.

JCron (33:14.55)
the tools and systems and marketing ability to fill those salespeople’s pipelines with something, I’m going to stay here and I’m going to win and I’m going to be back when the cycle repeats itself, which it always does. If you look at where we are today, it’s only a matter of time before we get back to low interest rates and everyone’s going to refi again. So not a regret, but an awareness of now if things were to change or if industries were to shift.

I would sooner look for the opportunity or gift in that shift versus the, I’m going to go start over somewhere else and reinvent myself entirely. Because I didn’t know it would take a decade to be any good at it.

Brad Weimert (33:55.774)
Well, I’ll piggyback on that last sentence, which is your frame that it takes a decade to be any good at it. Another perspective on that, or what I saw through that path is that you are accumulating skills. And so when you left the mortgage space, consciously or unconsciously, you lacked skills to thoroughly develop something. And so you started accumulating these skills, in this case, probably copy direct response, but marketing at large.

that you got from this new space. You didn’t have that, and possibly the competitors in mortgage did, and they had some other skillset, maybe they were older or whatever, and that allowed them to pivot more effectively. I don’t fundamentally think things are right or wrong or good or bad, they’re all contextual, and that’s another lens to see that through.

JCron (34:46.174)
No, you’re probably very right. Like when I look at the mortgage business, I might’ve been a one trick pony or maybe one and a half. Like I knew sales and I had a grasp of systems. So scripts, CRMs, that kind of thing. But as far as like the direct mail pieces we had, didn’t write them, didn’t know anything about it, just knew that the phone rang and people were excited to talk to me.

Brad Weimert (35:05.923)
Mm-hmm.

JCron (35:13.25)
So you’re 100% right. Like if I go back to that, I was one and a half skills in my now Swiss army collection of things that I can or know how to do. So you’re 100% correct.

Brad Weimert (35:27.286)
Nobody likes half a trick, J.Cron.

JCron (35:31.882)
Isn’t that the truth?

Brad Weimert (35:35.491)
So the other question is for the season folk, I look at that resume and if I didn’t know you and maybe even if I knew the names, the companies on the list, I would look at that and say short tenure, short tenure, short tenure, short tenure, what the fuck’s wrong, maybe I don’t want to hire them. So today with your most recent journey.

running a large company with presumably lots of employees, you can tell me the stats on that in a second, how would you look at that resume? And how would you think about hiring that person? Because presumably you would wanna hire yourself. How would you identify that was the case by looking at the resume?

JCron (36:22.306)
I would probably say it would largely depend on the role. So if I was looking at hiring somebody with a resume like mine for a senior software engineer, massively concerning, because that position typically does not have, unless it was all startups that, you know, funding issues, whatever, like unless there’s context that indicates that someone who is looking for a home and desiring to hone their craft didn’t have the opportunity to do so.

I would look at short 10 years as being very challenging. On the flip side, if I was hiring somebody in a sales or marketing or revenue generating role that had a fairly limitless potential to it, assuming they could execute, I would look at a short 10 year role as pretty much irrelevant because I would wanna see how well this person has done what they set out to do, where they set out to do it. And…

I’ve now been in enough companies to understand that one of the hardest parts and one of the most difficult truths of companies, the vast majority of companies are terrible at talent development. They’re terrible at career planning. They’re terrible at advancement. It’s just a very challenging thing. I don’t know anyone that’s done it really, really well. And so I think that most people that are very aggressive, very enterprising and desiring efficient growth.

They oftentimes bounce around more than you would like to see them bounce around, but it’s more because the companies are just not built to give someone the ability to advance as fast as you can advance by quite frankly, hopping around on your resume. Like, I mean, if you think about how long it would take you to be the CEO of a company and you look at it, getting there from, you know, starting in sales to moving to VP of business development to then moving to, you know,

I don’t know, more of a COO role to then a CEO role, well, you could do that path in three or four years with three or four companies. So to me, if you had somebody where it’s a three month stint, six month stint, that’s something I would be concerned about the personality dynamics. If you’re talking about somebody that’s been at a company for a year, to me, a year tenure today is not nearly as short as it was five years ago. So it would be something that I would say, and this is one absolutely that

Brad Weimert (38:40.952)
Mm.

JCron (38:45.034)
I think what matters more than anything is the reference checks. I see so much value today in reference checks that I didn’t see then. And most people are like, oh, well, no one’s honest in a reference check or nobody wants to throw anyone under the bus. It’s like, that’s not true. You can literally have a reference check where if they say a lot or if they say very little, the amount they’re saying, whether it’s all positive or not, is going to tell you everything you need to know. So I would say any resume that you’re like,

I don’t really understand that. Ask about it, push on the reference checks for sure, but the position you’re hiring for, I think matters a whole lot.

Brad Weimert (39:23.222)
How many people currently at Kajabi?

JCron (39:27.215)
Uh, 400-ish? Somewhere in there?

Brad Weimert (39:31.266)
That’s terrifying to me. What questions do you ask? What questions do you ask in reference checks?

JCron (39:35.301)
I don’t disagree with him.

JCron (39:40.866)
So for us in reference checks, number one, we’re always really hopeful that somebody had experience in some type of an entrepreneurial capacity. Like the one thing for me that has been the greatest divining rod of finding people that are super committed, super enthusiastic and super talented, is if they’ve ever been in some type of family business. Because to me, the number one thing that destroys an organization is if you ever let anybody in that utters the words of that’s not my job.

Um, that to me is just this, this immediate shift into something that is just horrible for an organization. So if I ever come across somebody who was part of a family business, I’m very, very excited in the reference checks. For me, all I’m trying to do is find out if this person was a passenger or a driver. That’s the number one thing. Um, did they do it or were they just around for it?

Brad Weimert (40:37.386)
I love that. I love that frame. Were you responsible for hiring? Were you the one doing the hiring at Kajabi?

JCron (40:46.09)
Depends on the season. So if you go back to when I started, when you know we were 25 team members, Kenny and I were involved in every aspect of hiring for every department. And then as we continued to grow, it went from we are integral to the hiring process to we are overseeing and participating in the hiring process, to we are setting the vision, the core values, and the foundational management principles, and the team is executing on them. So it just really depends on which season.

But yes, it was we’re everything to we’re part of it, to we’re Checkpoint Charlie, to we’re out of it in time.

And for everybody listening, sorry for the background noise. My three-year-old daughter loves to participate in my podcasts occasionally, so.

Brad Weimert (41:24.396)
Um…

Brad Weimert (41:34.482)
It’s delightful. So I have a lot of questions about that process.

At what point did you decide through, you know, go from 25 employees to 400? What were the breaking points where you said, Hey, I no longer have to be involved. And was it a product of what, what was that decision making process? I guess is the question.

JCron (41:59.594)
Um, it was probably more driven by circumstance than choice. So if you look at where Kajabi was, we were probably about 75 or 80 employees going into the two weeks to slow the spread thing. And then all of a sudden when the world was forced into a digital first versus a digital someday or a digital supplement, that was when all of a sudden our world got.

easy. That was your Mach 5 hair on fire, you know, compound growth rate of 10% month on month on month and literally breaking everything, trying to hire as fast as possible to support the demand. So I would say that we didn’t ever step back and say, well, you know what we should do is remove ourselves from this process.

It was more, we didn’t have the ability to be everywhere we needed to be. So we had to be very selective and the scale was sort of forced on us by the marketplace. Um, it was also something as well that, you know, Spectrum Equity were amazing partners. Uh, we joined up with them in the very beginning of 2020, just before March of 2020, when, you know, the, the two weeks, the slow spread thing kicked off. And having.

Brad Weimert (42:51.738)
Mmm.

JCron (43:16.838)
a group that really understood what hyper growth looked like, the intellectual capital that they brought to the table was invaluable during that season because it gave us a new lens on how to scale because our lens was always bootstrapped. It was bootstrapped, profitable. We will hire when absolutely necessary and there was no system or other methodology for improving what we needed to improve. Okay, we’ll hire.

JCron (43:45.406)
this is what massive scale looks like. And guys, it’s time to lean into it. So it was a major mental shift for us.

Brad Weimert (43:54.014)
Okay, so that’s a that’s another interesting topic. And that’s super enlightening for me. Why did you take money in the first place? I didn’t even realize that was part of the equation. So you bootstrapped up to what number and then you decided to take money? Why?

JCron (44:10.99)
So we bootstrapped until well beyond eight figures in revenue. And we probably would have stayed bootstrapped indefinitely because we didn’t need the money. We ignored a tremendous amount of inbound from private equity firms all over the place just because we didn’t have a need for it. We felt confident in our plan. We didn’t need the money. We had all the capital we needed to develop and grow.

whatever we wanted to do. But all of a sudden what changed was we started to really see a universe where things were changing. So we were bootstrapping profitable. You had Teachable at the time, which, you know, has largely now been relegated into a rounding error in another giant organization, but at the time they were VC backed and you know, they were growing and that’s how they were.

And then if you look at Thinkific, same thing, they were in the process of about to go public on the Canadian exchange. And so they were doing their thing. And so we sort of started to kind of step back and say, okay, what, um, you know, give me one second. Hey Morgan, daddy’s on a video conference right now. So if you would, can you go back in there and maybe play in the playroom until I’m off? All right. Thank you so much. And don’t forget to close the playroom door. Okay. All right. I love you.

So very much with Thinkific filing for their IPO, and we’re sitting here saying, okay, all we’ve ever wanted is to actualize the potential of this organization. And we’ve believed that this idea of, whether you call it the knowledge economy, the creator economy, whatever terms you assign, this will change the way the world learns. That as you see more people getting broadband internet access.

Brad Weimert (45:50.389)
Ahem.

JCron (45:57.654)
they’re gonna want to learn the same things. They’re gonna want to improve their career, improve their skills, find things they’re passionate about, learn about hobbies, all of the things that our industry powers. And we know that a book’s gonna be written about it at some point. And our only goal was to make sure the book’s written about us, not that we’re the footnote or the early stage company that somebody else built this industry. And so we really started asking ourselves, how can we surround ourselves with people?

that have seen where this is going to go and can help advise us. So it was far more of an intellectual capital exercise of who are we around and who are we having at that table for those key inflection points than it was a financial arrangement. And what we actually did in that process is a very scientific move called tacos and tequila, which we basically would go to our favorite Mexican restaurant with any private equity group that wanted to meet with us, and we would have tacos and tequila.

And the rule was if we wouldn’t have another lunch with these guys, even if we had no business involvement whatsoever, we’re out. So it’s like, if we didn’t want to be friends with them, we’re definitely not getting into business with them. And that was a process that, um, you know, spectrum has been amazing partners. And they’ve always solved for our customers more so than anything. They’ve always asked how to add value to our user base more than anything, much more so than that.

the spreadsheet modeling and everything else that comes with equity guys. So they were amazing partners and could not have shown up at a better time because, you know, with the growth that came, we definitely needed that around the table.

Brad Weimert (47:29.826)
Got it. So two questions. The first is you were seeking knowledge and understanding and expertise around how to go to the next level. But it sounds like for clarity, you were seeking that with money partners.

JCron (47:40.494)
Mm-hmm.

JCron (47:48.358)
I think we went with Money Partners because there was not really a lot of people that would be vested in our journey in just purely an advisory role. It doesn’t mean that we couldn’t have found it that way. It just means that we had all of this inbound, so we started having conversations and it just kind of organically became the right decision. It doesn’t mean that we couldn’t have done it another way. I mean, I think for everybody listening now that…

Brad Weimert (47:59.716)
Got it.

JCron (48:13.63)
is in that season of entrepreneurship where every day you’re the biggest company you’ve ever been and it will be true tomorrow and the day following, you begin to ask yourself, what don’t I know, what haven’t I seen? And I think that we had reached a point where our existing network didn’t have the experience set that we needed. So we went out to find it.

Brad Weimert (48:37.442)
Second question, what kind of tequila?

JCron (48:42.294)
Back then, it was probably 1942. That was normally the go-to, which has now been replaced by Classe Azul Reposado, just because the vanilla notes are delicious and a little bit more pronounced. So.

Brad Weimert (48:55.842)
best mass-produced tequila that exists.

JCron (49:00.146)
Yeah, I actually, it’s funny, I love it. It is just my absolute happy place and everyone that gets all snobby about it, they’re like, oh, that’s an industrial tequila. I like insert random brand that nobody carries and nobody gives a shit about. I’m just like, dude, that’s wonderful. I’m glad, you’re the guy that’s gonna tell me the book was better than the movie and I’m like, I just liked the movie and I finished it in two hours. So just stop being that guy. It’s wonderful your hipster happening. It’s great tequila, yes.

Brad Weimert (49:25.954)
just like the bottle of Claucer Azul. Yes, note I said mass-produced tequila just to accommodate the conversations with those people. And you know what? I like the one-off brands.

JCron (49:39.825)
Yes, I’m gonna start saying that. My favorite mass produced tequila.

Brad Weimert (49:44.114)
Yes. Because I do like the other brands. I do want to try all the other ones. But all the things you said are accurate. So I would be remiss if I did not ask about development because you’re running a software company. Oh, but before I do, can you tell me numbers on the PE split and how that shook out? Is that NDA stuff? Or are you able to talk about that?

JCron (50:07.174)
Yeah, that’s NDA stuff, unfortunately. I can tell you that what our culmination was, was in March of 2021, we raised $550 million on a $2 billion valuation, and that was anchored by Tiger Global, TPG, Owl Rock, Maritech, and Tidemark. But everything else is, you know, under NDA. So that was the last round that we did. And…

Brad Weimert (50:32.286)
That’s enough.

JCron (50:34.294)
They’ve been amazing partners as well. It’s been really, really cool to see the excitement that people have for what this industry is doing. Kajabi today is now powering roughly $1.9 billion annually in GMV, which is a fancy way of saying gross merchandise volume, but it means that our users are selling $1.9 billion a year of their knowledge products through the platform. And for us, that is the single greatest source of pride because it means that value is being

created, it’s being put out into the world by people that are passionate about it, and it represents $1.9 billion a year in transformative value for those businesses that are on the platform. So that’s our North Star metric. It’s really been the North Star metric of the company forever, which is our hero success. That’s pretty much our foundational belief. That’s where we start with everything.

Brad Weimert (51:27.35)
Love that. And it sounds like then you’ve had multiple rounds.

JCron (51:32.706)
Yeah, so Spectrum was our first partners and then our second set of partners were the group that I just mentioned and so that’s who now comprises our intellectual capital group, our board meetings, all of that.

Brad Weimert (51:46.458)
How do you like having a board? Oh, you’re on the board now, aren’t you? So you’re one of those guys.

JCron (51:50.398)
Well, yes, so Kenny and I are both on the board and what I would say is.

It has been tremendously frustrating, but it’s my fault, not the board’s fault. Um, going from being an up, it’s, it’s so hard because I mean, when you go from being an operator to then being a board member, it is, it is a massive shift in how you think, how you interact, how you lead it, it’s an entirely different universe, um, as an operator, it’s.

Brad Weimert (52:06.05)
There’s that ownership I was looking for in the beginning.

JCron (52:27.638)
do this right thing, let’s go. As a board member, it is very much nose in, fingers out. You are asking questions, you are probing, you are encouraging, you are advising, but you’re not operating. And that is a very big shift for people that have an operational bias. I’ve never been accused of being a patient guy. Being on a board is a very patient position.

It’s just a very different universe. So I would say that now two years into it, I understand it a lot more. I enjoy a lot of it. I appreciate the intellectual curiosity and intellectual capability that we have on the board. And now I understand a whole lot more of the role of what a board is versus early on, I had just come out of operating and I was like, literally trying to operate from the board. And that just doesn’t work.

It’s not what a board’s designed to do.

Brad Weimert (53:29.242)
How did you like running the company when you didn’t have a board to report to versus when you did through both phases?

JCron (53:38.446)
Um, I would say that if I were to look at my highest and best use as a leader, as an operator, the band that I got to participate in at Kajabi, that 6 million ARR to a hundred ish million ARR. That’s my sweet spot. Like it is product market fit is defined and it’s about how do we create a category and become an iconic company within that category.

That’s where I feel like my skill sets align most effectively. Um, where we are today and the growth that we’re experiencing and beyond. It’s amazing. I love that I get to participate as an advisor. I love that I get to participate in keeping the focus on the vision and why we do what we do, but it is a season of growth that is not as it doesn’t overlay as perfectly on my skill sets as the season that I participated in.

I would say that if I had a dream, if I had a magic wand, if I had Brad’s network of people and could figure out how to create it, I would love to find a few companies that are in that same zone and do the exact same thing because I just enjoy it tremendously. So like what I got to experience, my favorite season by far.

Brad Weimert (55:02.542)
Hmm. As the operator.

JCron (55:05.142)
I definitely as the operator when I was at Kajabi, I would say today with a three-year-old daughter, I would probably prefer to be in more of an advisory position than an operating position. Yeah, I’ve just gotten too accustomed to having a little bit more flexibility. So I would like to be important, but I would like to not be necessary is the way I would describe my involvement.

Brad Weimert (55:28.002)
Mmm.

Brad Weimert (55:31.23)
Interesting. Yeah, I mean, I could talk to you for an hour about that. That’s a it’s a curious next chapter of life. And I don’t often, I seem to and maybe I’ve got bias here, but I seem to not often come across people that move into an advisory position. And then think, you know what I want to do? Roll up my sleeves and get dirty building another business.

JCron (55:55.787)
I go back and forth on it. Like it depends on when you catch me. I mean, if I were to describe to you my, you know, my weekly rotation, it normally, and it takes a break during the fall and the holidays because I love the fall and the holidays. So I don’t think I’ll be as crazy about it right now. But over the last couple of years, it was basically on Monday, wake up, all right, I gotta get my shit together. I wanna do something fun. I wanna…

take something on, I want to really get going again. By Tuesday, I’m looking at industries, evaluating companies. By Wednesday, I’m starting some cursory diligence and starting to ask some serious questions. By Thursday, all of a sudden, I’ve uncovered some bumps in the road or challenges that seem like work and I don’t want to do it. And by Friday, I’m having lunch with my wife and deciding not to do anything. And then it starts over again on Monday.

Brad Weimert (56:47.278)
Sounds like you’re shopping.

JCron (56:48.402)
Yes, I would definitely say I’m interested, but I’m not committed. And I think that’s what I’ve come to learn that like I’ve spent the last two years trying to force something because there was this huge personal existential crisis of I’ve always been defined by what I do. I’m Jonathan Cronstedt, I go by J. Cron, but my identity was.

I’m the guy that builds companies. I’m the guy that runs launches. I’m the guy that sells things. I like, it was always defined by what I do. And when I wasn’t doing something, it was a very unmoored feeling. It was just like, I don’t know who I am. I don’t know. Today I’m the guy that has way too many pairs of Lululemon joggers and, you know, probably should wear adult clothes occasionally. Like it’s just one of those things where it was very disorienting. So.

I think that I spent a lot of time trying to force something. And I would say that now I wrote my book, my book’s finished, I have no idea what I’ll ever do with it, but I’m glad that I did it. And next up for me is more just a, I’m curious to see what life brings my way. I don’t know what it will be, but I think my season of trying to force it, probably done.

Brad Weimert (58:08.503)
What is the name of the book?

JCron (58:10.166)
The book is called Billion Dollar Bullseye, grow as big as you want, as fast as you want, and exit if you want on your terms. And the framework of the book is designed around playing darts. I believe the way that you win at darts is not to actually be better at darts than everybody else, but to throw at a bullseye that’s bigger than what everybody else is throwing at. So it’s kind of this idea where if you’re looking for a framework of how to build a business and what we learned building Kajabi, starts at the center with purpose, then profit, then product. Those are your…

core three that if you don’t have it, you really don’t have a business. And then your amplifiers after that are going to be your prestige, promotion, persuasion and people. So that’s essentially your customer experience, your marketing, your sales and the people that run those systems. And it’s a methodology of really how I look at, evaluate and approach scaling companies. The one that’s the most fun that I enjoy talking about is that people are last on that. Everyone’s like, oh my gosh, I can’t believe you say people come last. And it’s not that people come last. It’s actually that…

Brad Weimert (58:58.074)
Mm.

JCron (59:07.13)
I hate the amount of people that just talk about, oh, just hire A players, just hire A players. It’s all about the talent. It’s all about who you hire. And it’s like, that is the worst advice imaginable. It is the hardest thing to systemize. It is the hardest thing to depend on. And the reality of it is no A player wants to fix your dumpster fire. Like if you’ve got some areas of business that are super ugly and you’re like, I’m just gonna hire someone really talented. That really talented person is gonna feel like you tricked them in the interview and they will be looking for the exit right away because

All they want to do is go where they’re going to be viewed as talented. They don’t want to, you know, like I said, fix something with super broken. So I believe that your people are an incredible asset, but they will only shine as brightly as the stage you put them on and they will only perform as effectively as the systems you give them the ability to run and improve. So that’s why for me, the order of those areas is so important because if you’re not nailing each of the areas in order, you’re going to supplement or surrogate

another ring and you’re going to miss the multiplying that’s supposed to happen. So if you’re relying on people to fix bad sales or bad marketing or bad customer experience or worse yet, bad product or bad profit, you’re done. It’s just not going to happen. So that’s kind of the book.

Brad Weimert (01:00:23.67)
Love it. Second question. You mentioned and before we started, I think and you just hit on it a little bit, that you’re leaning into the unknown and trying to calm the fuck down and figure out what comes next in life. For anybody that is you know, that has exited a company. How do you do that?

JCron (01:00:47.178)
Um…

JCron (01:00:51.306)
I don’t know that I know. I would love to say that I’ve got a formulaic approach to it, but I would say that it probably just requires time. It requires time to decompress a little bit. I’ve probably got some bad wiring from the PTSD of my bankruptcy, of that fear of, oh my gosh.

I have to be working, I have to be doing something, I have to be producing, I have to be… And all of those tracks, the longer that they’re running, the quieter they get. It starts out deafeningly loud, freaked out, panicked. It’s why you see a lot of people that exit a company that all of a sudden are over invested in 142 things and they miss it because those things are so loud that you can’t…

give them the time to kind of dilute and go away in a certain sense. So I don’t know that I have an answer other than I feel better about it now than I did a year ago than I did a year before that. And I would say that what I’m learning is the likelihood of something happening is just as good with me forcing it as it is with me allowing it to happen.

Brad Weimert (01:02:13.242)
Hmm.

JCron (01:02:13.782)
in the season that I’m in now. So we talked about the two audiences you have being the individuals that are just getting started and the individuals that are just starting scaling. And I think that those require two very different approaches. That when you’re just getting started, you should be saying yes to everything. You should be getting exposed to as many opportunities as possible. And your focus, in my opinion, should not be on systems or scale, but on yourself. It should be on the skills that you need to be the person you need to be to achieve the outcome that you want to have.

That’s what that stage is. When you start to get to scaling, it shifts because you should now be saying no to a whole lot more things than you’re saying yes to. You should be moving from just in case learning to just in time learning and only really digging into the skills and the growth for the area that you need next to move forward. You’re not trying to go to a buffet. You’re simply saying, I need a thing. So learn that and then that will present the next thing. So.

Brad Weimert (01:02:57.59)
Mm-hmm.

JCron (01:03:11.582)
I think there are two very different scenarios for starting versus scaling. And today my season is much more significance than it is anything else. That I’m seeking the thing that I just want to do so badly that I can’t say no to it, that I can’t not do it. And I would say that I’ve come up with a lot of things that I could do, but I haven’t come up with anything that has such a strong pull that I can’t not do it.

and I’m waiting for that thing that I can’t not do.

Brad Weimert (01:03:46.074)
Awesome, that’s helpful. Well, I want to be respectful of your time. I have a question about development that could snowball, but in simplest forms for the sake of your time. What are the necessary elements of a development team? And let me give you some context here. I know lots of people that stumble through software development.

Myself included. And I hear different approaches to the required team members in necessary to build a product. But if you were to have a small team, let’s go back to when you had 25, what are the necessary roles in a small software development team?

JCron (01:04:30.158)
So I’m going to give you two answers. The first of which is I’ve got thoughts here, but this was an area where I was extremely fortunate that Kenny, my, my partner, the engineering side was him. You know, he was at the time when we had 25 team members, he was the chief product officer, he was the CTO more or less. Um, it was.

a situation where that was his zone. And so I would say that I have a lot of thoughts on, as I’ve watched us grow and scale. And here’s the part that I think would be informative or helpful to answer your question from my point of view. And it would simply be, there is a huge difference between delegation and abdication. Delegation is equipping others to do a job or a task that you know enough about to manage the outcome.

Brad Weimert (01:05:13.165)
Mm-hmm.

JCron (01:05:20.898)
Abdication is handing somebody something that you don’t know what they’re doing. You don’t know how they’re going to do it. And you’re hoping you get the outcomes you want. Delegation is extremely effective. Abdication is extremely dangerous. So I would say that if you are trying to get into software and your position on it is abdication, namely, I’m just going to start hiring some people, be prepared for an extremely expensive and soul sucking boondoggle that you’re going to hate.

If you’re talking about delegation in the sense of your first hire must be somebody that has the skills and knowledge that also has the vested interest in the long-term success of the company, not the long-term success of their contract for billable hours. You got to have that person because I think that outside of it, unless, unless you’re in a market.

that you can benefit from today, this rise of no code, this rise of off the shelf modular, like Dharmesh from HubSpot, quite frankly, he’s done a lot of discussion about the role that AI is gonna play in development. And everybody thought AI and robots were gonna take out all the lower end jobs. And I actually think it’s the opposite. I think they’re gonna come after the higher end jobs much faster. So it won’t be long before you can show up on a website with a chat bot and tell them what you want built, and they’ll do all the coding for you.

and they’ll literally just serve you up a box of code that you plug into ship. So that’s coming. But I would say until it gets there, if you don’t have the technical knowledge, you better have somebody on your team that does, that is in that foxhole with you. Otherwise, there’s just way too many people that are perfectly happy to take your money. One thing I would suggest reading, I’m looking for my book here.

Stahil Lavendia, he was the one who founded Gumroad, wrote a book called The Minimalist Entrepreneur, which I think is really good regarding this. And the other one that I love is Aman Agarwal’s, the tech fluent CEO. It’s a spectacular field guide that really is like, okay, you’re not a developer, but you’re in a software engineering business. What do you need to know? How do you need to ask? How do you manage those things?

Brad Weimert (01:07:14.154)
Mmm.

JCron (01:07:38.622)
If you can at least build those muscles, that’s where I think you can be incredibly successful.

Brad Weimert (01:07:45.282)
That’s awesome. I’ll, uh, I’ll read that for sure. And, um, I need to know that stuff.

JCron (01:07:51.094)
The number one thing just makes your interests are aligned. If you’re building a company that’s based on profitability and effectiveness and you’re writing checks to people that are paid on time in, code lines written and things that have nothing to do with the metrics you’re measured on, if you don’t know how they do what they do, your equation is not gonna work, just flat out won’t.

Brad Weimert (01:08:12.598)
Love it. J. Cron, I appreciate carving out time, man. It is always entertaining to talk to you.

JCron (01:08:18.21)
Thanks man, this was a lot of fun. I hope that for everybody there that this was valuable, enjoyable, that you got something out of spending your time here with Brad and I. I would certainly say anybody who’s listening, Brad is one of the most consummate professionals in the world of entrepreneurship. His experience in a variety of businesses and his vantage point is very unique. So it’s something where you’re going to see EasyPay Direct’s knowledge set continue to bring you unique insights because they’re participating in

more industries in a more meaningful way than very many people. So you found a great spot. You’re going to learn a ton, stay in part of this. And I would just say, take the risks, take your shots. Life’s too short to live a life of quiet desperation and doing something you hate. The world needs you to be excited about something, whatever it is. So find it. I’m trying to find the same thing.

Brad Weimert (01:09:09.646)
Jay Kron, thanks so much, man.

JCron (01:09:11.658)
You got it. Chat soon everybody.

Brad Weimert (01:09:16.374)
Love it, man. Thank you.

JCron (01:09:17.886)
Yeah, that was fun. I haven’t gotten to complain about how millennials are ruining the world lately. So it was a really enjoyable one.

Brad Weimert (01:09:27.409)
Yeah, it was a good way to kick it off

JCron (01:09:30.519)
Always a good time, man. I love getting to say what I actually am thinking. It’s so fun.

Brad Weimert (01:09:36.238)
I think it’s fantastic. Do you plan on leaving your house at any point in the near future? I.e. travel?

JCron (01:09:43.411)
Mmm.

JCron (01:09:46.99)
Probably not. Like, I might, I’ll probably be at TNC in Vegas just because I want to see TNC in Vegas, but I would say if I don’t have a specific reason to be someplace, I’m probably not doing a lot of it just because, you know, it’s kind of like I could be at home with my daughter and I know that these years are magical and not to be repeated. So I would say once she’s in school and doesn’t really give a shit about dad.

That I would probably say I’d pick up the travel because I miss it I love just getting to connect with people doing cool shit. Like what I missed the most was being a Kajabi seeing the amount of businesses that were being launched and grown and talked about like it’s It’s intoxicating when you’re around that much entrepreneurship and to go from that to I Get a couple of stimulating conversations a week not super fun So I miss it, but I don’t know that it’s gonna come back that fast

Brad Weimert (01:10:42.803)
Oh.

Brad Weimert (01:10:46.81)
Oh yeah, well, you know, trade-offs in life.

JCron (01:10:50.834)
Absolutely, that’s the, you know, you got to step into that joy of missing out and just decide that you’re going to own it. So I would say I’ve spent two years trying to force it and now I’m just going to spend some time seeing what happens.

Brad Weimert (01:11:07.678)
Yeah. How much time do you spend on?

JCron (01:11:10.227)
How about you, dude? How’s everything with Easy Pay Direct? What’s new in Brad’s world?

Brad Weimert (01:11:16.61)
It’s, it’s crazy. It’s a yeah, it’s all good. We bought a new office building and crushed it on the old one, which is great. Brought on a head of strategic partnerships this year and a new VP of sales. And the partnerships person’s already been amazing. She’s been doing payments partnerships for seven years. Yeah.

JCron (01:11:19.796)
Crazy good crazy?

That’s awesome.

Brad Weimert (01:11:45.898)
And so, you know, her Rolodex, I had a conversation about how weird it is that I still use the word Rolodex recently, but

JCron (01:11:52.73)
What else are you gonna call it? Nobody says the Contacts app on your phone. I mean, way to go Rolodex, nicely done, yeah.

Brad Weimert (01:11:58.922)
Address book. Yeah. It’s deep. So that’s, that’s great. We’re doing some cool shit. We just did an integration with payments AI for click funnels to handle all the stuff that they can’t. So you know, there’s just this whole host of stuff when you’re trying to leverage a payback that you can’t board. And so it’s all of the, we’ll call it high risk stuff, but it’s such a broad

section of stuff. So that’s big. And then we’re looking at other platforms got a we’ve had a couple calls with high level about doing their payments entirely, like being the payment engine for high level payments or whatever the fuck they’re going to call it. It’s great. That’s all great. But it’s, it’s a lot, you know, we’re moving fast. And I could tighten up to the dev team more than it is. And, you know, doing too many things at once.

JCron (01:12:42.318)
It’ll be fun.

JCron (01:12:55.902)
Yeah, but cashflow covers a multitude of sins and it’s way easier to figure out how to grow faster than it is to save your way to growth. So I mean, if that’s the season you’re in, I think your orientation is dead on.

Brad Weimert (01:13:07.946)
It is, and it’s easier. You know, those are, those are big conversations too, because there’s a lot of that’s mindset, right? As a bootstrap, a hundred percent owner. Um, I just, and, and with my background, you know, like I had to hold on tight for, for long enough.

JCron (01:13:23.842)
That’s the hardest reality of scale. Like that’s the thing that it is so hard. My favorite line that, you know, I’m sure I stole it from somebody, but I call it my own is, you know, you’ll never know the price of success until after you’ve paid it. You can only decide to buy it and then find out what it costs afterwards. And I think that scale is one of the hardest things because it’s sort of like, okay, I’m gonna make less and I’m gonna do more.

And I don’t know how long I will make lesson do more for in order to get to this place where I then make way more. And it’s, yeah, I mean, it’s a weird, uncertain, like congratulations, you’re now in the abyss. And we have no idea how long you’ll be there for. And we know it’s gonna be really scary and you’re gonna be wondering why you ever did it. And I mean, there’s something to be said for that. There’s also a great book I read called,

Brad Weimert (01:13:57.057)
and if it’ll work.

JCron (01:14:16.758)
I think it was tiny giants, but it was the amount of companies that stayed small on purpose and just chose to pursue excellence rather than expansiveness. And it was kind of interesting. It was really one of those like, look, if you’re in a business with a durable, sustainable advantage, you might just love being the greatest version of yourself, whether you ever exit or not.

But if you’re in a business where it’s a binary land grab of sorts, then yeah, the only thing to do is grow real fast and get taken out by somebody bigger. So it’s a fun season, man. If I can ever be helpful as a sounding board, obviously you know how to reach me.

Brad Weimert (01:14:57.29)
Yeah. Well, I appreciate that man. And it’s, this is the first year where I had this, like, I, and I think realistically, um, I try to create, I try to create frameworks that allow me to make things more black and white, um, knowing that there are very few absolutes in the world. I still try, right? The frameworks help navigate that. And, uh, I had these frameworks around spending that like, even if they’re logical, I need to be so far past.

a logical framework in terms of like what I have versus what I spend versus what’s coming in. And I think once enough got cleared off the table, then it opened me up to be like, I don’t I don’t what else do I need? You know, like, okay, now let’s fucking go. And I always said, you know, a minute for growth, and then enough money started coming in. And I was like, oh, shit, maybe like, just give it to me. Give me the money.

And really that’s about security, right? It’s really for me about what if it all hits the fan?

JCron (01:15:58.922)
The only wisdom I would give you that I think I wish I had held in a more top of mind space, whatever you do when you’re scaling, never not pay yourself, ever. Because it was one of those moments where I remember it clear as day, I’m CEO of Digital Marketer, we were a launch driven company, so literally we were only as good as our last promo. And there was a moment where I’m CEO and I’m like, guys, we might…

miss payroll, like we’re not doing distributions this month and whatever. And Roland said to me, he said, you know, we are absolutely doing those distributions and I’m like, but we can’t. And he goes, no, you don’t understand. If we don’t, we’re going to leave this in a machine that right now is not doing what it’s meant to do. And we will never know where it’s broken or how we need to fix it. If we don’t hold it to task. So if we take the distributions and somehow we need to recapitalize, that’s fine.

But if we don’t take them, we’re never gonna figure out where it’s broken, why it’s broken, or what to do about it. So bottom line, we’re taking them. And at the moment, when I was the CEO, it was my ass, I was fucking furious. I was like, you guys are assholes. I don’t wanna do this, this sucks, blah, blah. And now looking back on it, I’m like, man, that was so smart. Like when I look at the amount of people that are like, I’m not taking any money out, I’m foregoing a salary, I’m got growth, I got it, I got it, I got it. And I’m just like, man, if you don’t,

recognize that this is supposed to do the thing that you created it to do and you don’t hold it to that, you’re not going to find your way. Because it is so important to have those guiding moments of, okay, I took the money, but now it’s broken and I got to figure out what.

Brad Weimert (01:17:43.326)
Yeah, I love that. I think that’s great insight and great advice. And I have no intention of not paying myself. It’s only to say that I don’t need to take so much, you know.

JCron (01:17:50.222)
Give me the money! I love it.

JCron (01:17:57.732)
Mm-hmm. No, dude, I dig it. I’m excited to continue to hear about the scaling and I will keep you apprised of my wayward wondering, so.

Brad Weimert (01:18:06.166)
Please do, if you make it to Austin, hit me up.

JCron (01:18:09.618)
Most definitely, dude. If I go anywhere, it’ll probably be that because Roland keeps asking me to go to Austin with him. So, I mean, it’s only a matter of time before I’m like, yeah, I’ll go to Austin, so.

Brad Weimert (01:18:19.026)
Awesome. Well, yeah, hopefully it’s sooner rather than later. And if I make it out your way, I’ll do the same.

JCron (01:18:25.058)
Sounds great, Brad. Always a pleasure, dude. Great to see you. Bye.

Brad Weimert (01:18:27.906)
Likewise, man, you too. See ya.