IAM1644 – Entrepreneur Shares Raw Lessons of his Journey

Podcast Interview with Jake Jorgovan

Why it was selected for “CBNation Architects”: Jake is a wealth of knowledge and it's always great to have another podcaster in the podcast community on the show. He talked about the entrepreneurial journey and the things that we learn along the journey. I also loved hearing the questions or prompts he uses to journal as well which is a space that's created to reflect on the journey.

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Previous Episode: https://iamceo.co/2021/09/20/iam1134-entrepreneur-shares-raw-lessons-of-his-journey/


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Jake Jorgovan :00:00

Yeah, one of my favorites, my first business advisor, Alex McClafferty. He's one of the co-founders of WP Curve, which they did a phenomenal thing and then went off and sold the GoDaddy and started working with him. And that was like a key turning point in my life and business. And one of the things that he said to me that has always stuck with me is, your business is a reflection of yourself.

Intro 00:20

Are you ready to hear business stories and learn effective ways to build relationships, generate sales, and level up your business from awesome CEOs, entrepreneurs and founders. Without listening to a long, long, long interview? If so, you've come to the right place. Gresh values your time and is ready to share with you the valuable info you're in search of. This is the I am CEO podcast.

Gresham Harkless 00:46

Hello, hello, hello. This is Gresh from the I am CEO podcast and we're doing something a little bit different this year with some of our episodes. We're repurposing some of our favorite episodes around specific topics related to entrepreneurship. This month we're focusing on entrepreneurship and community. Us, we, our, together and we're gonna look at entrepreneurship and industries and different types of entrepreneurship and ultimately what that really means. But we're also gonna delve deeper into the importance of community, networking, niche communities and how that supports being a CEO, entrepreneur, and business owner. So sit back and enjoy these special episodes around entrepreneurship and community.

Hello, hello, hello. This is Gresh from the I am CEO podcast and I have a special guest on the show today. I have Jake Jorgovan of Jake- jorgovan.com. Jake, it's great to have you on the show.

Jake Jorgovan 01:32

Thanks for having me on here, Gresham.

Gresham Harkless 01:33

Super excited to have you on. And before we jumped into the interview, I wanted to read a little bit more about Jake so you could hear about all the awesome things that he's doing. Jake is a serial entrepreneur, author, podcaster, and business advisor. He's the founder of Content Allies and Lead Cookie. Through these companies he has generated. $40M+ million in sales for his new clients. Jake is the host of the Working Without Pants Podcast and Leaders of B2B podcast. He also shares the raw lessons of his entrepreneurial journey on his site, and Jake's professional focus is on building companies that enable freedom of time and financial profitability.

He does that by being an active entrepreneur in the trenches and through training others on entrepreneurship, leadership and sales and marketing. Jake has degrees in entrepreneurship from Belmont University and has been awarded Nashville's Youth Entrepreneur of the Year. He has spoken at conferences such as South by Southwest and has been featured in publications such as Inc and Forbes. Always super excited to have a fellow podcaster, especially one that focuses and has so much knowledge on B2B. So Jake, super excited to have you on the show. Are you ready to speak to the I am CEO community?

Jake Jorgovan 02:29

I'm ready.

[restrict paid=”true”]

Gresham Harkless 02:30

Awesome. Well, let's do it then. So to kind of kick everything off, I wanted to rewind the clock, hear a little bit more on how you got started, what I call your CEO Story.

Jake Jorgovan 02:37

Yeah, so I basically have been self-employed in some capacity since 19. Pretty much at that point, I had been doing a handful of part-time jobs, was in college and really started off my first company, which back then I was just doing like audio and video production. And I just at some point committed to like, I'm gonna like work and figure out a way to make this work. So it was some level of business and freelancing that then evolved into what became a first agency that I ran for a while, and I did that for a number of years. Eventually you know, exited the agency with my partner. Wasn't anything crazy or anything, but just kind of basically like sold the business to him and then moved on and then basically fumbled around for a number of years. Freelance, did the whole nomad thing. And then probably about, I guess going on four and a half years ago or so, I started Lead Cookie, which became one of the next companies I had that really actually hit some level of scale. And then, a couple years ago I started up Content Allies, which is my current business of focus as well, which is a podcast production agency. And currently have another one that's in the works as well. But that is kind of the high level story and in a nutshell, there.

Gresham Harkless 03:42

Yeah, I absolutely love to hear that. And especially like, I think so many times we forget, like our journey doesn't start right when we like pitch out our sign and say we're open for business. A lot of times, I'm sure a lot of things you've learned probably through the audio and production obviously you're probably using today with you and your team.

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Jake Jorgovan 03:56

Yeah, it's just, whenever I tell people like when people are starting an entrepreneurship, I'm always just like, you're in for a ride because you have no idea how many skills you need to develop to be an entrepreneur. And it's like you'll neglect a certain skill like finance or sales or marketing or stuff like that, and you'll gravitate to the things you excel at and you'll get by at some point and then some point that will just bite you. Like, I just remember at one point like finances just went, it was just like clear that I was neglecting this skill and I had to like reconcile two years of books in a matter of a 60 day window. And so there's so many skills you have to learn and I think it just comes through getting started doing it and then just figuring out where you're weak and trying to up-level those skills.

Gresham Harkless 04:42

Yeah, absolutely. And I think it's so important too, to be able to have those people around you that maybe have different skills. Because like you said, I mean it is building a business so many different and moving parts and a lot of times just like we are as individuals, we'll be stronger in one area than the other. So we have to make sure that we're kind of taking care of that balance, being active of entrepreneurship.

Jake Jorgovan 05:00

That's true. And I think there's the level of surrounding yourself by people that can augment you where you're weak, but not neglecting to gain a base understanding. And basically my mistake in finance was I just was like, I'm not a numbers guy, that was like my story and I love numbers now. But I was not a numbers guy, and so I neglected it. And then thus I was hiring this bookkeeper who was basically just like taking advantage of me doing basically zero work and nothing was actually organized in our books at all. And so I, think there is that, you know, surround yourself by people, but like, you need base level at least in like everything, or you can kind of get taken advantage of if something that can happen.

Gresham Harkless 05:38

Yeah. I appreciate you mentioning that and being transparent about that too, because I think so many times those things don't get told as much and to understand like the lesson that comes from that, which is to make sure that you do have an awareness of who potentially you're partnering with or you're hiring or something along those lines so that at least you know you're getting what you paid for at the very least. And so, I know you said you like numbers now. So I mentioned the, over 40 million that you've been able to do for clients. Could you take us through a little bit more on how you've been able to do that and how you're serving clients now and what's, what it's like to work with you?

Jake Jorgovan 06:05

Yeah. It's been through a variety of different means, but I mean, where I kind of gravitated toward I started off with the agency and video production and at some point I realized that I was, really good on the sales side of things. And my partner was really great on the production. So in my first agency I was kind of like running sales and everything. That led to me for a long period of time doing basically outbound sales consulting where I was doing just a lot of outreach. And that's kind of what Lead Cookie became, is basically an outbound sales agency. And so through that we've done a lot of business development, a lot of sales and everything outreach through that, just direct outreach and just cold email, LinkedIn outreach, cold calling, all those kind of things. That is like one capacity that's been really valuable. But the other, is actually through podcasting, which is one of the other reasons I started at this agency because as I'm sure you know, as a podcast host, when you interview people you build a relationship with them and you can probably make an ask to them or try to, you know, support them.

They become kind of like your peers because you know, you interviewed them and everything like that and you just become friends. And so that, honestly, my podcast drove a massive amount of revenue for my own business. And so I started doing this for others and started seeing how this could drive revenue as well through partnerships, through, even interviewing your customers or interviewing influencers, people that have lists of your customers. These are kind of like a lot of the two of the big channels that I've done a lot of the work through, which have really generated the results. And so it's really been that outbound consulting and the podcasting side of things that have really been the revenue drivers that have produced results for clients.

Gresham Harkless 07:31

I wanted to ask you now for what I call your secret sauce. And this could be for your business itself or your podcast, or a combination of both, but what do you feel kind of sets you apart and makes you unique?

Jake Jorgovan 07:40

Yeah, I think what it really comes down to, I guess when you talk about your zone of genius. I also like the kind of phrase, like unique ability from Strategic Coach and stuff like that. And so I've put a ton of time into self-improvement and self-development. And one of the things that the unique ability book from Strategic Coach is like, I think a really great process and there's others that are similar, but the core idea is, literally learn and understand yourself and where you are uniquely talented. When you fully, deeply understand where you are great and where you are weak, that enables you to excel. So basically I know that I am someone who likes to achieve things. That's like my number one. I'm a good achiever, but I also. I'm a person who's like, I just like to start something like right away. I want to jump in and I want to go. I like one-on-one conversations. I don't like group dynamics. And I am very much like about ideation, just going in on stuff. But I also have learned that my weaknesses are anything that is like repetitive and recurring.

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And so it's like you give me something I'm excited about and I'm just like, boom, go in and I'll just like work and  I'll just work into my weekend or something because I'm so excited about a project, but it's like, okay, every Tuesday you got to do this thing Jake. And, I'm just like, Ugh. Oh God I just won't do it. That actually held me back for a really long time because whenever  before I had a company, I'm doing outbound, I was trying to just be an outbound consultant and it was just like crazy because I would like sell someone on an outbound like sales retainer where we would just do cold email and all I had to do was just check the inboxes every day and like, did anyone respond?

And if it worked the leads and like I would just show up, be like, ah, I just like wouldn't do it. And then like clients would churn and results would get terrible. And eventually it was like I need other people right to do that daily thing. There are people that enjoy structure and repetition and the same thing every day. I've had other people just on my team that are like I want to come to work on Monday and I don't want anything unpredictable to happen in my week . That is not me, that would be horrible. So I think that's what it comes down to, is understanding yourself where you're really good. And then getting yourself into that seat and then surrounding yourself by people that are good at the things that you are not.

Gresham Harkless 09:47

Yeah, that's absolutely huge. I appreciate you sharing that, from a personal perspective, like what works for you. So I wanted to switch gears a little bit, and I wanted to ask you for what I call a CEO hack. You might have already touched on this, but this could be like an app, a book, or a habit that you have, but it's something that makes you more effective and efficient.

Jake Jorgovan 10:02

So many different, I guess, kind of frameworks. But I guess one that I love is I do like a guided framework of morning questions every morning when I journal. Let me actually just pull up a few of my questions just because  I go through these every day. These I've gathered from various things like Strategic Coach or even my advisor or stuff like this, but I answer the question I want blank every day. And it's just kind of like clarifying a want and then what is moving the needle? And so what am I doing that's actually making a difference toward getting to what it is I want? What am I procrastinating on? That's a very useful one. If you just ask that every day there is something that you're, annoying in mind. This today has some expletives in it because it's something I really didn't wanna do, but I had to do and then let me see, what are some of the others here?

I ask, like what is one specific and massively important reason why I want more money and why I want it, why is it so important? Similar thing I ask about my fitness stuff like that and ask what is something I should question every day? And so I just try to question my assumptions, like, should I be doing this? Should I not? Is that accurate? And yeah, that is. And another one is just, you know, what drains me and then what makes me happy. I kind of journal through these each day. And those are just pretty good questions that are on my journal, daily journaling. But that daily reflection and a time to pause and think and kind of look at what's working, what's not working, what am I avoiding? I find that those are really great things to align that can like actually drive actions each day that'll change things.

Gresham Harkless 11:20

And so I wanted to ask you now for what I call a CEO nugget. This could be a word of wisdom or a piece of advice. It might be something you would tell a client or if you hop into a time machine, you might tell your younger business self.

Jake Jorgovan 11:30

Yeah. One of my favorites, my first business advisor, Alex McClafferty he's one of the co-founders of WP Curve, which they did a phenomenal thing and went off and sold to GoDaddy. And I started working with him and that was like a key turning point in my life and business. And one of the things that he said to me that has always stuck with me is, your business is a reflection of yourself. That is just something where there are so many people where they are looking for tactics or they're looking for things or someone else that'll give them the answer, but ultimately if revenue is an exchange of like a measure of value that you're creating in the market, then it's simply you don't know how to create enough value. That's really what it comes down to. So you need to figure out, okay, how do I create more value, whether that's marketing to more customers or delivering a better service or delivering a service that more people want and deem valuable. And this whole idea that anytime like you're not happy with your current situation, that it's like in some capacity like you can work on that or improve that or figure it out or up level of skill. It was just like, you know, at one point my profits were terrible and I realized because I'm horrible at finance and I'm just blowing money and I have no idea why there's no money left at the end of the month. And so that came down to me learning and having to upskill that and gaining finance as a skill. That's where I think just kind of like looking at that is your results in business are that kind of reflection in some capacity.

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Gresham Harkless 12:52

Nice. Absolutely appreciate that. And so I wanted to ask you now my absolute favorite question, which is the definition of what it means to be a CEO. And we're hoping to have different quote CEOs on the show. So Jake, what does being a CEO mean to you?

Jake Jorgovan 13:04

I think being a CEO ultimately comes down to building a business that can exist and run without you. Like that's the really big longer term challenge. And it is really being able to get to that point where you can step back and guide it. And what's interesting is I've actually been able to pull that off with Lead Cookie and to an extent where I'm not involved in the day-to-day. I basically invest probably less than one hour a week in that just kind of a weekly call to check in with my leadership team. But that's pretty much all I do and that's really cool. But also I think there's like the CEO of the business and then there's like the CEO of just kind of your life and your portfolio. For me, I've got multiple companies because while I'm not active in Lead Cookie, I also realize that there's a lot of inherent, just problems in the business model of a lead gen company and which is what led to me going off and starting Content Allies and starting another company. So I think it's also being able to take that bigger picture and look back and saying, you know, I'm the CEO of these businesses, but I'm also the CEO of my life. What is the life that I wanna design? And like, how do these businesses that I'm building fit into that? And I think that's a really cool, interesting thing, especially with for like small business owners.

Gresham Harkless 14:08

Awesome. Well, Jake, truly appreciate that and appreciate your time even more. What I wanted to do was just pass you the mic, so to speak, just to see if there's anything additional that you can let our readers and listeners know, and of course, how best they can get ahold of you, find out about your podcast, all your different projects and all the awesome things that you're working on.

Jake Jorgovan 14:24

Yeah, so the main hub where I kind of do all my writing and my podcasting and everything is that Jake-Jorgovan.com. If you try to type any variation of that into Google and Jorgovan you will, I'm the only one out there, so Google will spell correct you and hopefully get you over to my website. But that's kind of the main hub for it. And then Lead Cookie and Content Allies are my two main projects, leadcookie.com and contentallies.com. So you can check either of those out there, but that's the main place to go. I try to publish articles on everything I learned. And I have a podcast called Working Without Pants as well. So those are a lot of main avenues for me there.

Gresham Harkless 14:56

Absolutely, and we'll definitely have the links and information in the show notes, just to make it even easier so you don't have to let Google, you know, do whatever it always does. But for people that are listening that wanna listen to your podcast too, you're covering like different business topics and information related to podcasting business in general as well too, there, right?

Jake Jorgovan 15:10

Yep. Yeah, so I do a mixture of solo episodes where I just share things that I'm learning, going over 200 episodes strong, have a lot of fun with it, and people seem to get a lot of value out of it, so I enjoy it.

Gresham Harkless 15:19

Yeah, definitely. Appreciate you making it. Of course, you know, spending some time here. We will again, have the links and information and show notes as well for that. But Jake, truly appreciate you again, my friend, and I hope you have a phenomenal rest of the day.

Outro 15:30

Thank you for listening to the I am CEO Podcast powered by CB Nation and Blue 16 media. Tune in next time and visit us at iamceo.co. I am CEO is not just a phrase, it's a community. Get your driven CEO gear at ceogear.co. This has been the I am CEO podcast with Gresham Harkless, Jr. Thank you for listening.


Dave Bonachita - CBNation Writer

This is a post from a CBNation team member. CBNation is a Business to Business (B2B) Brand. We are focused on increasing the success rate. We create content and information focusing on increasing the visibility of and providing resources for CEOs, entrepreneurs and business owners. CBNation consists of blogs(CEOBlogNation.com), podcasts, (CEOPodcasts.com) and videos (CBNation.tv). CBNation is proudly powered by Blue16 Media.

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