IAM1134- Entrepreneur Shares Raw Lessons of his Journey

Jake Jorgovan is a Serial Entrepreneur, Author, Podcaster, and Business Advisor.

He is the Founder of Content Allies and Lead Cookie. Through these companies, he has generated $40M+ in sales for his clients. Jake is the host of the Working Without Pants Podcast and Leader of the B2B Podcast. He also shares the raw lessons of his entrepreneurial journey at Jake-Jorgovan.com.

Jake’s professional focus is to build 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, sales & marketing.

Jake has a degree in entrepreneurship from Belmont University and has been awarded Nashville’s Youth Entrepreneur of the Year. He has spoken at conferences such as SXSW and has been featured in publications such as Inc & Forbes.

• CEO Hack: Guided framework of morning questions and daily reflections/journaling
• CEO Nugget: Your business is a reflection of yourself
• CEO Defined: Building a business that can exist and run without you

Website: https://jake-jorgovan.com/

https://contentallies.com/

https://jake-jorgovan.com/blog/top-podcast-production-companies-services

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Transcription

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00:20 – Intro

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.

00:49 – Gresham Harkless

Hello. Hello. Hello. This is Gresh from the I AM CEO podcast and I have a special guest on the show today.

00:53 – Jake Jorgovan

I have Jake Jorgerman of jake-jorgerman.com.

00:53 – Gresham Harkless

Jake, it's great to have you on the show.

00:57 – Jake Jorgovan

Thanks for having me on here Gresh.

00:59 – Gresham Harkless

Super excited to have you on. And before we jump into the interview, I want to read a little bit more about Jake so you can hear about all the awesome things that he's doing. And Jake is a serial entrepreneur, author, podcaster, and business advisor. He is a founder of Content Allies and Lead Cookie. And through these companies, he has generated 40 plus million in sales for his new clients.

Jake is the host of the Working Without Pants podcast and leader of the B2B podcast. He also shares the raw lessons of his entrepreneurial journey on his site. 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 and always super excited to have a fellow podcast, 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?

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01:56 – Jake Jorgovan

I'm ready.

01:57 – Gresham Harkless

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

02:04 – Jake Jorgovan

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, you know, part-time jobs 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 of 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 the 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 like a kind of basically like sold the business to him and then moved on.

And then, you know, basically kind of fumbled around for a number of years, freelance did the whole nomad thing. And then probably about, I guess going on 4 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 of 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 the high level story and then a nutshell there.

03:15 – Gresham Harkless

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

Yeah, it's, it's just that 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 was like, and like, you'll neglect a certain skill, like finance, or sales, or marketing, or stuff like that. And you'll go 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 like, I was neglecting this skill and I had to reconcile 2 years of books in a matter of like a 60-day window.

03:59 – Jake Jorgovan

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 uplevel those skills.

04:17 – Gresham Harkless

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 as you said, I mean, it is building a business, so many like different and moving parts. And a lot of times, like, 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, you know, taking care of that balance being backed off entrepreneurship.

04:35 – Jake Jorgovan

That's true. And I think there's the level of surrounding yourself with people that can augment you or your week, but not neglecting to gain a base understanding. Yeah. And basically, my mistake in finance was I just was like, I don't, I'm not a numbers guy. I don't, that was like my story. 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 0 work, and nothing was actually like 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 and like everything, or you can kind of get taken advantage of as something that can happen.

05:15 – Gresham Harkless

Yeah, I appreciate you mentioned that and being, you know, being transparent about that too, because I think so many times, you know, those things that 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 on 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 40 million, 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 how you're serving clients now and what it's like to work with you?

05:44 – Jake Jorgovan

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 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 kinds of things. And so it's that is like one capacity that's been valuable. But the other is actually through podcasting, which is one of the other reasons I started up 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 support them.

They become kind of like your peers because you interviewed them and everything like that and you just become friends. And so that honestly, like 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.

So these are kind of like a lot of the 2 of the big channels that I've done a lot of the work through, which have generated the results. And so it's really been that outbound consulting and the podcasting side of things that have been the revenue drivers that have produced results for clients.

07:15 – Gresham Harkless

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

07:25 – Jake Jorgovan

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 like self-improvement and self-development. One of the things that the unique ability book from a strategic coach is like, I think a really great process. And there's others that are similar, but The core idea is literally to learn and understand yourself and where you are uniquely talented.

When you fully, and deeply understand where you are great and where you are weak, that enables you to excel. And so basically I know that I am someone who likes to achieve things. That's like, it's like when my number one, I'm a good achiever. But I also am a person who's like, I just like to start something like right away. Like 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.

So it's like, you give me something I'm like riled up and excited about. And I'm just like, boom, go in and I'll just like work. And I like, I was just like working to my like weekend or something, cause I'm so excited about a project. But it's like you like, okay, every Tuesday, you got to do this thing, Jake. And it's just, I'm just like, oh God. And I just won't do it. And that actually held me back for a really long time.

Whenever I had company, I was doing outbound, I was trying to just be an outbound consultant. And it was just like crazy because I would like to sell someone on an outbound sales retainer where we would just do cold emails and all I had to do was check the inboxes every day. And like did anyone respond and fork the leads? And I would just show up like, I just like, wouldn't do it. And then clients would like to churn and like results would get terrible. And eventually, I was like, Oh, no, I need other people to do that daily thing.

Because there are people who enjoy structure and repetition and the same thing every day. Like I've had other people just on my team that are like, no, like I don't, I want to come to work on Monday and I don't want anything unpredictable to happen in my week. And it's like, that is not me. Like I wouldn't, that would be horrible. So I think that's what it comes down to understanding yourself where you're really good and then getting yourself into that seat and then surrounding yourself with people that are good at the things that you're not.

09:38 – Gresham Harkless

Yeah, that's absolutely huge. I appreciate you sharing that, you know, from a personal perspective, like what works for you. I think I love how it kind of segues into what we were talking about before like making sure that people around you have their own ingenious, their strength point that they're able to kind of lean into and they can compliment each other then you have a really great team.

09:54 – Jake Jorgovan

Exactly, yep, that is, it's such a big part of it.

09:56 – Gresham Harkless

Yeah, absolutely. 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.

10:09 – Jake Jorgovan

Yeah, I would say so many different, I guess, kinds of frameworks, But I guess one that I love is I do kind of like a guided framework of morning questions every morning when I journal. And let me actually just pull up a few of my questions. Just because I go through these every day. And these I've gathered from various things like a 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?

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 and mine 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, 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.

11:13 – Gresham Harkless

I ask, what is something?

11:13 – Jake Jorgovan

I should question every day. And so I just try to question my assumptions like, should I be doing this? Should I not? Like, is that accurate? And yeah, that's another one is just, you know, what drains me, and then what makes me happy. And I kind of journal through these each day. And those are just pretty good. Most of the questions that are on my journal daily journaling, but that kind of daily reflection and a time to pause and think and kind of look at like what's working, what's not working, what am I avoiding? I find that those are really great things to align that can actually drive actions each day that'll change things.

11:45 – Gresham Harkless

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

11:56 – Jake Jorgovan

Yeah. one of my favorites, my, my first business advisor, Alex McClafferty, he's one of the co-founders of WP Curve, which did a phenomenal thing and then went off and sold the GoDaddy and, started working with them. That was 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're looking for like tactics or they're looking for things or someone else that will give them the answer. But ultimately, like your business, like the revenue, the if like if revenue is an exchange of like a measure of value that you're creating in the market, then it's simply like 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 delivering a better service or delivering a service that more people want and deem valuable. And this whole kind of idea that anytime like you're not happy with your current situation, that it's like in some capacity, you can work on that or improve that or figure it out or level a skill.

It was just like, at one point my profits were terrible and I realized like, that's cause I'm horrible at finance. And like, I'm just like blowing money and I have no idea why there's no money left at the end of the month. And so like that came down to me, like learning and having to upskill that and like gaining finance as a skill. And so that's where I think just kind of like looking at that is like your results in business are that kind of reflection in some capacity.

13:24 – Gresham Harkless

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

13:35 – Jake Jorgovan

And 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's really being able to kind of 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, it's also then, though I think there's like the CEO of the business, and then there's like the CEO of just kind of your life and like your portfolio. And for me, I've got multiple companies because while I'm not active in lead cookie, I also realized that there's a lot of inherent, just, problems in the business model of a lead gen company.

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 kind of take that bigger picture and look back and saying, you know, like I'm the CEO of these businesses, but I'm also the CEO of my life. And like, what is the life that I want to design and like, how do these businesses that I'm building, like, how do they fit into that? I think that's a really cool, interesting thing, especially with small business owners.

14:45 – Gresham Harkless

Awesome. Awesome. Awesome. Well, Jake, truly appreciate that and appreciate your time even more. What I wanted to do is 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 podcasts, all your different projects, and all the awesome things that you're working on.

15:00 – Jake Jorgovan

Yeah. So, the main hub where I kind of do all my writing and my podcasting and everything is at jake-jorgerven.com. If you try to type any variation of that into Google and Jorgerven, 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 2 main projects, leadcookie.com and contentallies.com.

So you can check either of those out there, but that's kind of the main place to go. And 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 the kind of main avenues for me there.

15:38 – Gresham Harkless

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 do whatever it always does. But for people that are listening, they wanna listen to your podcast too, you're covering different business topics and information related to podcasting, business in general as well as who they're, right?

15:52 – Jake Jorgovan

Yeah, so I do a mixture of kind of solo episodes where I just kind of share things that I'm learning. Then I do a lot of interviews with agency owners and consulting companies in the Working Without Pants podcast. And so yeah, it's a mixture of those and just kind of whatever peaks my interest at the moment, but we're going over 200 episodes strong, and have a lot of fun with it. And people seem to get a lot of value out of it. So I enjoy it.

16:12 – Gresham Harkless

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

16:23 – Outro