Jake Jorgovan: from solo consultant to three companies

Full transcript

Edited for reading. Select a time to play the audio from that point.

The 24-page article that never went live (00:00)

Alex: Now, why would I do something like that?

Jake: It’s a 24-page article and you didn’t let me publish it.

Alex: I remember this now. This is actually a great jump into the convo. What was going on? Was I freaking out or something?

Jake: I don’t know, man. We coached for years, and I used the same Google Doc the whole time. I have it somewhere.

Alex: That one’s called “Alex McClafferty Agendas”. I’ve looked at that one.

Jake: Yeah. It’s hundreds of pages of notes from those calls, and me prepping notes for calls. One day I went through it, highlighted all the key learnings and turned it into this whole thing. I think you just didn’t want me to publish it for some reason, and it never went live.

Alex: I’m glad you found it. Dude, that’s so weird. You know this very well about me: I had a lot of trouble self-promoting. I was never comfortable with it. I used to make this joke with people: my marketing team is Jake Jorgovan.

Jake: Yeah, because I was all in on the thought leadership and the blogging. I didn’t really know what I was doing, but I blogged a lot and people thought I knew what I was doing. I was like, no, I just work with Alex and he knows what he’s doing.

Alex: That was kind of the vibe. And then I’m like, don’t say anything nice about me, it’s weird. You can refer me, but just don’t tell people.

Who Jake is (01:50)

Alex: Let’s kick it off. I’m joined by Jake Jorgovan. In a lot of ways Jake is the guy who prompted me, and helped me, to become a legitimate coach. I dabbled for a while and used it as a pseudo-therapy, to share stories and have cathartic moments with people who were trying to build businesses. Then I would talk to Jake, and you would say things like, “You’re actually quite good at this, and this is helpful.” So before we jump in, Jake, thank you for continually pointing the mirror back at me. It’s a very coachy move. Welcome to the pod. For people who don’t know you, who are you? What’s your background?

Jake: I’m Jake Jorgovan. You can find me at jake-jorgovan.com. Serial entrepreneur is the best way to describe me. We worked together from the early days, even before Lead Cookie, all the way through into Content Allies, and now it’s turned into multiple other businesses.

The way I explained it to my dad, when I could finally explain what I do for a living, was this. When you run online businesses, you can start a new business overnight. You set up a new website and a new offer and you can start. So I’ve improved the skill of building online businesses, and I’ve solved better problems each time I started something. Most of the time I would start something, get into it and realize I’d screwed up the business model. Then I’d do a little better the next time, and a little better the time after that. Now I’m in a spot where the momentum has hit and I’m like, OK, wow, I’m on the path. But that took five iterations of digital businesses.

From a college video agency to Content Allies (03:50)

Alex: You landed on the radar in, I want to say, 2014, with a guest post on the WP Curve blog about Squarespace. Is that right?

Jake: Yes. I did a Squarespace versus WordPress article, which was one of your top performing articles. Back in the day I was doing Squarespace web design. I had no clue what I was doing on SEO, but you guys did. You guided me to that post, it ranked well and it drew some traffic.

Alex: That wasn’t your first foray. You’d done some stuff in business land before that. Take me back to the inception.

Jake: Inception: a video agency. I started it in college. We did productions for live events, like graphics for stage productions at concerts. That turned into corporate events, where we designed the cool animation that goes behind the speaker when they walk on stage. We did projection mapping before it became mainstream.

That was the first business, and it was really cool. We worked with really big customers. It was wild. I was really young and hitting success, I had some good advisors and mentors, and I played the “I’m a young college kid, help me” vibe. People would coach the hell out of me. That’s something I’ve learned through my whole life: any time I have a coach, I accelerate much faster.

Then I went freelance in digital marketing for a while. That turned into digital businesses: various forms of consulting, web design, stuff like that. Lead Cookie was a cold email and LinkedIn outbound agency. We got in early, when it was good. Then it became saturated and spammy and everyone was doing it.

So eventually I segued into Content Allies, which has been a podcast agency. Today it’s growing into a full B2B content, marketing and growth agency. I still run that. And I have some other crazy ventures, like a healthcare recruiting company, which is getting momentum right now, and an HR consultancy. I’m taking those marketing skills and applying them to other industries. Professional services is where my focus has landed.

I realized recruiting is not far from running a marketing firm. You hire different kinds of people. You hire the right ones, deploy them and drive leads. That’s my journey in a nutshell.

An email list makes a launch fast (06:35)

Alex: I looked back at the very old version of my coaching site, and there’s a testimonial on there from you. When we first started working together, it was something like 60 days to $20K MRR.

Jake: I think that was the Content Allies launch. Maybe. I feel like Lead Cookie hit really fast, and Content Allies did pretty well out of the gate too.

I credit a lot of that to having an email list and a following. The one thing I did well the whole way along was build the personal brand. I think it’s a Dynamite Circle concept, spotlight marketing: you have an audience, and you can point them at different offers. So I kept trying stuff and saw what worked. When you have an email list of a few thousand people, you say, “Hey, I’m doing this,” people buy, and it’s pretty fast. It also tells you pretty quickly when you’re failing. You put out an offer and no one buys.

The offers that sold but didn’t work (07:55)

Alex: That’s a heartbreaker, the launch to silence. But there’s an inverse of that, and we had some of it at WP Curve. Do you remember Content Club?

Jake: Yeah, yeah.

Alex: It wasn’t a runaway success, but it had enough people, a kind of critical mass, to do something. And it tricked us into thinking we were community moderators. That’s a completely different business model, with a completely different cadence and rhythm. It was enough for us to feel like there was something there. I think it lasted six months. Those are the worst.

Jake: I had some of those as well. We had a VA service for content marketers, to do all their publishing for them. It was called Tell Betsy. It got to $5K or $6K a month, and you think, OK, cool, there’s something here. And then it hovers. You get some churn, you sign some new people. Customers are paying, but it’s not really profitable. Those are the ones that linger for four or five months, and you’re like, this sucks. But it’s not a clear no out of the gate, because you make a bunch of sales and you think, whoa, we’ve got something.

Copy a business that already works (09:15)

Jake: What I realized from launching all these things is that it’s one thing to sell it. Then you have to deliver it, and it has to be a business you want to be in from the delivery side.

What I found over the years is that whenever I tried to come up with some new idea, like VAs for content publishing, it kind of sucked. Just copy some level of something that already exists. That’s the validation. You told me this: do market research. With every company I launch now, I ask, can I find some big players who are succeeding in this space? That’s an indicator that it’s a good move, and that I’ll succeed if I stay focused on it. The blue-sky ideas never really panned out.

Alex: Yeah. It was something something compound annual growth rate, something something businesses in the market that have customers. There’s a whole acronym. RESCUE, the RESCUE framework.

Jake: I used that a lot, whenever I was looking at things. Is it recurring? I can’t remember the rest.

Alex: We’ll find it. I’ll add it to the notes.

Jake: You’ve got to republish that. Over time I started building my own framework too. It’s the Ray Dalio model: would I be happy if I had started this business five years ago? Will I be happy five years from now if I start it today?

Platform risk at Lead Cookie (10:50)

Jake: I remember when we started Lead Cookie, you said, “Hey Jake, I don’t know, man. There’s a lot of platform risk with LinkedIn. You might want to be careful about building your whole business around this one platform.” And I was like, ah, whatever, man, people are buying like crazy.

And then LinkedIn changes their whole thing. I’m still friends with the Lead Cookie guys and it’s a great business, but the number of times LinkedIn has changed everything on them, and they’ve had to rebuild their whole ops. It’s massive platform risk. Those are things you can ignore early, and they really do become serious problems down the line.

Alex: I do remember there were certain things I would drone on about, and platform risk was one. I’m not going to tell you not to do the business. But I also have to be honest and say, listen, make hay while the sun shines, but you can’t bank on it. You’re building on a sandy foundation that doesn’t have anything solid underneath it.

Excitement versus conviction (11:55)

Alex: One thing about the RESCUE framework, and it’s taken me some time to learn. One of the Es is excitement: do I actually care about this problem space? The one I’d add is a C for conviction, because there’s a difference between excitement and conviction.

With some of the businesses I’ve worked on, I had an intuitive sense that there’s something here. This is a real business. Emotionally I can click with it, and logically it’s a matter of following through. With WP Curve it was: have a thousand people felt this pain, and would they pay 70 bucks a month to have it taken away? That was really easy to get to. The conviction was so strong that it became a function of time.

But I’ve also tinkered on other projects where I was fooling myself a little. I’d say, “If I could just convince someone that this would make their life better, then this could be huge.” Whenever you’re saying “could be”, you’re maybe slightly off course.

Jake: A hundred percent. That’s a huge part of how I look at it now. When I decided to start a healthcare recruiting company, I knew hardly anything about the market. But I’m learning, and I’m seeing the opportunity. I research it, I look at other companies in the space, and my God, these companies are huge.

So the conviction I have is this. I know other people are succeeding at this. I’m talking to some of them, and I don’t think they’re very savvy. I think if I go into this, I can absolutely crush it. It’s a probability thing. Chances are, if we invest in this, we’ll crush it in time. You gather data points, and you’ve got to not get delusional about it, like you said.

One of the biggest things I remember you saying is: “Assuming that you will succeed in whatever it is you do, why are you choosing this business?” I still remember that exact quote from years ago.

Alex: That was a great one. You could do anything. And if you can find other people who have done it, you know it’s possible to succeed in that business. So then the question is, why choose that one of all the things?

Solving more expensive problems (14:25)

Alex: So, to the current day. I know there’s some action happening that we’ll keep private. But if you answer that question for yourself today, what’s the juice behind what you’re doing? Why are you working on what you’re working on?

Jake: Over the years I learned to solve more expensive problems. You told me to go upmarket, and that’s kind of what shifted me out of marketing. Selling marketing stuff is annoying. If I can go learn another industry, and use my marketing skills in that industry to solve a way more expensive problem, that’s pretty awesome. That’s what excites me: how can you play business at a bigger level? Where do you have a competitive advantage, or some unique skills?

Alex: You’ve got your quiver of things you know you can do: launch, get traffic, get referrals, build relationships, get something moving, set up a process, run it quick.

Going upmarket: the first deal was Meta (15:35)

Alex: OK, this is a good one: me nagging you to go upmarket. I want to preface it by saying this is very, very common when you’re starting out, and even a few years in. You deeply understand your customer’s pain, because your customer is in a very similar position to you.

When we started WP Curve, the launch note went out in the Dynamite Circle, and we grabbed a couple of customers who had websites and were hacking away and starting up. They were awesome, because they were the early customers who gave us the validation. They were also terrible customers, because they churned within two months. They didn’t really have a business and couldn’t sustain 70 bucks a month.

So when you and I were talking, maybe across Lead Cookie and Content Allies, it was about the positioning. Let’s talk through the positioning and the client profile.

Jake: Lead Cookie has gone upmarket since, in some capacity. I sold that one to the guys who are running it. Lead Cookie is still awesome and they do amazing work. I use them for all our outbound. But we didn’t really go upmarket when I was in that business.

Content Allies is when we went upmarket, and we got lucky by stumbling into the first one. The first deal we signed was Meta. I remember the guy at Meta said, “My manager said we should hire the young and hungry agency and not the big established player. So we’re taking the risk on you.” And I was like, awesome.

Once you have one of those logos, the rest come easier. You rinse and repeat. You’ve got to learn enterprise sales. It’s a different world, and you have to learn how to sell consistently at that level. But the dollar amounts get way bigger. It effectively isn’t as much work, but it’s also more work, because you’ve got to deal with a bunch of crap. Really, you’re charging them more for all the overhead: presentations to show value, KPIs, all the things you don’t do with small business.

It helped us raise rates, which was very important and needed, and it got us to a much healthier margin. We still serve a ton of small business, but not the same small business. I used to serve independent coaches. That’s not our market any more. We might take independent consultants who are making a million dollars plus and want their podcast done easy and right. But for the most part we serve small and mid-market businesses and enterprises, with a good mix.

It was a journey. I was talking to my partners in the other business the other day, and I said, I remember when I used to look at agencies with big logos and think, God, how do they have all those logos? And then you’re on the other side of it, and it’s not that different. It’s a matter of learning how to market to those customers, and then learning how to manage them and what they want. It forces you to grow, but it’s well worth it and far more stable. It’s really nice to get large, stable revenue on an annual contract. It tends to be quite profitable as well.

Enterprise revenue swings harder (19:00)

Jake: The hard part is that the upmarket stuff swings way harder with the economy than small business does, which is why I like a balance of both. When the upmarket stuff is good, it flows and it’s beautiful. But we’ve gone through so many weird economic swings and recession scares in the past several years, and everyone cuts budgets so fast on this kind of thing.

In a lot of cases you’re far removed from any real, quantifiable value. With a small business you can say, “Look, we’re moving the needle for you.” With an enterprise it’s, “Cool, you got views.” With a massive company you mostly have no ability to track. You can’t even say, “Let’s set up an email capture.” That’s against compliance, or it takes a developer. So you’re in vanity land with a lot of them, which means you can be cut.

One January we had forecast an almost $600,000 to $700,000 swing in revenue, just from enterprise churn because of recession fears. I had to do a bunch of layoffs, and that sucks. Fortunately we still had a lot of small business, so we were good. But that’s three or four enterprise accounts deciding to cancel, and that much changes that quickly.

A day across three companies (20:40)

Alex: So you’ve gone from a solo consultant slinging websites all the way up to sitting with the big dogs and selling big deals. Where do you spend your time now? What does a day in the life of JMFJ look like?

Jake: It’s busy. I’m effectively split across three companies, so I’m leading teams. Currently I run sales for Content Allies, which I look forward to getting out of. I made the decision to bring in a really awesome account manager, and we did a merger. At the size we’re at, the business can’t afford an ace account manager and a salesperson. So I run sales, because account management was draining me.

Then I’m in the weeds building up the healthcare recruiting piece and leading the team there. My goal is, within the year, to be out of any doing and into full leading. I would be already if I had one company. But I don’t do that. I end up with multiple.

I’m a very operational person. I like to dive in, build a rough system and then put other people in place to run it. That’s how I attack business. It’s what I enjoy. So I’m almost always in the weeds somewhere, and managing a bunch of teams in the places where I’ve already got out of the weeds.

So it’s a lot of team calls, a lot of leadership calls, working some larger sales deals, connecting with partners in the other businesses, and trying to work out other partnerships and growth avenues. We’re even looking at acquisitions. It’s a full mix these days.

Leadership, and what marriage counselling taught him (22:35)

Alex: Talk to me about leadership. Going from solo to having a team is a pretty big jump, and going from one team to multiple teams means a lot of moving parts. How did you get into a position where you could be an effective leader? What are some practices you’ve learned over the years to get the most out of your team?

Jake: I got a lot of that from you early on: how to run one-on-ones, and that book, The One Minute Manager. Super basic, simple things that get you into management and delegation.

But there are so many levels to it. There’s the idea that management is getting results through people instead of doing them on your own. That’s a soft skill, and you have to keep levelling it up.

Oddly, some of the biggest leadership lessons I got came from marriage counselling. My marriage counsellor said, “Oh, so you’re an autocratic leader.” I was like, what does that mean? I don’t even know that word. So I started researching it. It’s not quite micromanaging, but I like to have control. I like to be fully in there. I did a whole thing with ChatGPT: this seems like a limiting thing, how do I overcome it?

It’s levels of self-awareness. I also have triggers, the whole “not enough” thing, or when someone criticizes me. I uncovered that through counselling. Some level of leading is working on yourself, so that your bullshit doesn’t get in the way of actually leading people. Because it so easily can. It’s that, combined with getting good at understanding, listening and connecting with people.

Alex: It’s a funny one, because it’s warm and fuzzy and hard to wrap specifics around. But it’s very evident when a business has a leader who knows how to get the best out of their people, versus one who wears them down.

Out of nowhere last week, the second WP Curve developer, Juan Pablo, popped up on my LinkedIn. It’s been 11 years, and we’re still cracking jokes from back in the day. Do you remember that song, “What Does the Fox Say?”

Jake: Yeah, yeah.

Alex: For whatever reason, that song put me into a trance state of productivity, and I listened to it over and over again. This was the early days. I think we hired him two or three months in, when we had enough clients to bring in a second dev, and we were like, whoa, we’re building a team.

There’s something to be said for having a huge gap in time and being able to pick up where you left off, with mutual respect. How’s the family? How’s life? I think that’s sometimes lost, because you’re under heaps of pressure, you want your team to perform, and you push them really hard. If they can’t get there, they’re “not a good fit”.

Layoffs (26:20)

Alex: Have you dealt with conflict? You’ve mentioned layoffs. Talk me through that.

Jake: It’s never easy. The biggest thing is that I’ve always operated from transparency. Whenever I had to do layoffs, I’d say, “Guys, this is where we’re at. Either we do this now or it gets worse down the line. This is what we have to do.”

It sucks. The first time you do it is terrible. It gets easier, because you will have to do this multiple times in your career as an entrepreneur. Guaranteed.

I’ve learned how to approach it and not take it so personally. The first time I laid someone off, I think I literally curled up in the fetal position and felt sick. It was horrifying. Further in, you think, this sucks, but you get through it, and people understand. You do the best you can to support them, help them find other positions and give them recommendations. You do everything you can. But these customers all churned and we have no choice.

I don’t want to say you get immune to it. But the pain of it also makes you a lot better.

A structure that survives a 20% drop (27:45)

Jake: I had to do layoffs a couple of times, and after the last one I asked, how do we not have to do this any more? So we built a structure. 80% of the company’s capacity is full time. Everyone else is hourly. That gives us a flex staff. We can handle a 20% drop in revenue by ramping down hourly team members, and we don’t have to lay people off.

That structure came out of two rounds of layoffs. The reality is that the business will go through up and down trends. How do we build a more resilient company? The pain forces you to evolve the model.

Alex: Did you ever feel that sense of personal responsibility, where you’ve hired someone and you think, these people rely on me for their salary?

Jake: It’s rough when you put it in that framing. You have to realize that you’re not fully responsible for them. You are responsible for being a fair employer: you commit to what you said you would, and you give notice or severance. You try to be the best you can. But I definitely had that feeling, and it’s not a good mental place to be. At some point you have to do some emotional distancing, so you don’t wreck yourself when you go through these things.

Alex: I see it quite a bit, especially at early stage. You build a small team, and everyone puts their heart and soul into the business you’re building. Then either they’re not a fit or the business environment changes, and you’ve got to make some difficult decisions.

It took me a long time to get my head around it. I had a real sense of ownership and responsibility. When I talk to folks who have that now, I can see it really quickly. You dive right into someone else’s world and make yourself indispensable to them. But you’re also hamstringing yourself and them, because there’s a dependence that comes with it. It’s nuanced, but it’s for sure a trap.

The ukulele business (30:20)

Alex: One of the things we chatted about when we reconnected after a few years was ukuleles. I try to drop this into a couple of podcasts now, as a sidebar, to bring some flavour to the convo. Talk to me about ukuleles.

Jake: I love this, because it’s impact. I finally did the trip to visit my team in the Philippines, which you tried to get me to do for years. We did a three-day team get-together. We all went out to an island and hung out. While I’m there, the team gifts me a ukulele, and they’ve all signed it. Let me grab it real quick.

Alex: Can you play a bit? Is it in tune?

Jake: It’s terrible and it’s out of tune. I’m normally better. They gave me the tiny one. But the whole team signed it, and it’s gorgeous. It’s made out of bamboo.

So I say, “This is amazing,” and one of the guys says, “Yeah, I made this.” I’m like, what? You made this thing? He says, “Before I was doing podcasting, I had a ukulele company, from 2009 to 2022. We went under during COVID.” They were making 50 ukuleles a month and shipping them to a buyer in Hawaii, who sold them to tourists. Tourism died, and then they couldn’t export. The whole business went under. It was him and his wife running it.

He’s one of our top podcast producers, and he’s still with us. So I came back and had him ship me the ukuleles. He had about 20 that had been sitting there for years, finished, that he never could sell. He shipped them to me on consignment and I paid for the shipping. This is the crazy part: I funded the whole thing with the credit card points in the business.

We put up an Etsy store. I got them professionally photographed and used ChatGPT to write some cool descriptions, and we started selling ukuleles on Etsy. I’d say we’ve sold 50 to 60 now, across a bunch of different models. There’s effectively a luthier or two in the Philippines working on this full time. His wife runs the Etsy store. My producer is the lead designer. He comes up with the ideas and gives them to the other luthiers to build. The other instrument makers had been driving taxis.

Alex: Sorry, what is a luthier?

Jake: A luthier is someone who makes wooden instruments. A woodworker of instruments. It’s wild. They make them and ship them out. I have not made a dollar off this, but it’s a self-sustaining business now. They sell three, four or five a month, and they’re all able to make a living doing this, which is super cool to me.

Alex: I love it, man. I’ve mentioned this to a couple of folks: the idea of being in a position where you have the free time and the resources to do something that’s not just commercial, but useful for a community or for folks who need a helping hand. I’ve got to commend you on that. It’s one of my favourite stories of this year. Just you, strumming away on the ukulele, talking to Meta.

Jake: It’s opened up a whole dream for me. I have this in a separate LLC, and my vision is: can I make a company that helps creatives get self-sustaining projects going, using my skills? There are so many artistic, creative people who are really bad at business. These things are amazing. For me it’s not that hard to get those steps moving. For a woodworker who doesn’t understand internet marketing, it is. So how can you use your skills in a unique, fun way, and get to a level of abundance in your business where this isn’t a distraction? It’s fun.

Assume you will succeed (35:20)

Alex: I’m having a flashback to 2019 or so. The comparison between Jake of 2019 and Jake today: I’m very impressed, man. I’m so pleased. It comes through in what you say. You seek improvement, you do therapy, you seek coaching. But you also execute, and you keep failing forward. You make mistakes and course correct, make mistakes and course correct. There’s something to be said for the willingness to give it a crack.

Jake: You coached me on this many times. You’d say, “Yeah, cool. Just do it. Sounds good.” And then, “All right, what have you done?”

Alex: There’s something to that. I’ve got to commend you on it. I don’t know if it’s a nature thing or a nurture thing.

Jake: I think it’s resilience. I’m looking at that article again, and it’s that question: assume you will be able to succeed at anything, so why this? Once you assume success, things change.

There’s a whole journey in this too, of wrestling with your money mindset. You have to go through a phase and get to an abundance mindset. It sounds fluffy, but it’s a real thing to go through.

At some point a couple of years ago, I decided: I’m going to be a multi-millionaire. It’s going to happen. Time is the only variable. I’m going to screw up. I’ve definitely hit some cash crunches, and had debt on businesses at times, and thought, oh crap. You feel like you’re backsliding. But in the grand scheme, I know I’m going to keep learning, I’m going to overcome this, and I will get to that success point.

Then it becomes a whole abundance mentality. I’m not going to worry about buying the more expensive thing at the restaurant. I’m going to buy the good version of what I want and not try to be cheap. Even though I don’t have unlimited capital, money is infinite. I will make more. That’s a whole other part of the journey. It gets you comfortable taking risks and playing at a bigger level, because you realize a setback is not a big deal. You’re going to overcome it, as long as you don’t make your risk exposure too big. Which you also taught me: risk management.

Risk management (38:00)

Alex: Oh, no one wants to hear about risk management, dude. But I think it’s so prudent. It needs a sexier name so people will actually listen, because as soon as you say “risk management”, they’re asleep.

Jake: It gives you so much comfort when you think about it. Take a bet on something new, like starting a venture or ramping up a new service line. It’s thinking in probability and odds. I’m going to put down a $5,000 bet. I’m going to hire for this, and I have high conviction it will turn into a $100,000 payoff. My downside is $5,000. And the bigger the bet gets, the more you ask: what’s the risk on the downside? What other things can go wrong with the business?

Some of it just helps you sleep at night. I remember doing the whole exercise: what are all the things that could cripple me? Then, what can I put in place? Let me get business insurance. Let me make sure I’ve got two-factor on everything. You go through and do a bunch of those things. You’ve looked at what can cripple you, you’ve taken the actions you can, and you move forward. I feel a little safer when I sleep at night.

Alex: That exercise. If there’s one thing people listening or watching take away, it’s this. You have a business, and there’s a portion of the back of your head, 10 or 15%, that’s taken up with a swell of things that could go wrong.

Write down a massive list of everything you think could cripple your business. Make it as small or as large as you want. In the next column of the spreadsheet, write the actions you can take to manage each one. Just getting it out in front of you, holy crap, dude, it’s freeing. It gets all that noise out of your head. You can take some action on it. You’re not going to get everything, and there will be weird black swan events, because that’s how life goes. But it’s for your day-to-day sanity.

Is there a better way to say “risk management”, so I can make it more appealing to people?

Jake: Downside mitigation.

Alex: I don’t know if that’s an improvement. Actually, that’s pretty good.

You are the worst person to do every job in your business (40:40)

Alex: All right. This blog post that has never seen the light of day. One of us has got to publish it. I think some of it still stands. Hopefully all of it. Is there anything that jumps out as you scan that table of contents?

Jake: The first one at the top: you are the worst person to do every job in your business. I love that one. It’s a great reminder to myself now, because there are so many times when you think, no, I can’t give this to anybody else.

I held on to account management for years. Then I brought in this guy who’s an account manager. He’s ex-Salesforce. He’s been trained in account management. It was instant upsells. I’m like, what the hell? I didn’t upsell anybody. I just avoided churn.

You find people who are good at the role. Even if they’re 80% as good as you, they’re not overburdened by everything else you’re doing in the business, so they’re going to do it better than you.

I tried to start this recruiting thing, and I was trying to manage the whole recruiting team. We flopped on our face and failed horribly. As soon as I put a lead in there, we were crushing it. Get the hell out of the way. Hire people who know how to do what you’re trying to do. They deliver better than you will. That’s a beautiful thing to learn: you are not the superhero you so badly want to be.

I called out one of my partners on this at one point, because there was a huge client issue. I said, “Look, man, I know you want to Superman this.” I call it Supermanning it. There are points in business where you’ve got to Superman it. You hop in there and brute-force fix some huge client problem. But I said, “You can’t keep doing this at the scale we’re getting to. You’ve got to let go, give someone ownership, put a bonus structure on the other side of fixing this problem, and get the hell out of the way.”

That works. It’s amazing what you can do. I’ve done it a bunch of times. At one of our huge enterprise accounts we were flopping. I went to my lead on the account and said, “If they renew their contract, you get a $2,500 bonus.” Contract renewed. Simple things like that let you get out of the way, and what it does to level people up is next level.

Trust, and letting go (43:35)

Alex: There’s something about the trust that requires. The way I’m wired, I trust by default. I’ll give you space to operate, you’re going to make mistakes, and that’s completely cool. For you, coming from a solo background into building a team, did it take time to feel comfortable with that level of trust, and with letting go?

Jake: A hundred percent. That was a lot of the autocratic thing I had to overcome. It was hard for me to trust people fully. I would manage way too closely. It was really hard to let go.

I remember going through the exercise. Give someone a clear outcome. Get really good at defining what success is. Give that to them, and then ask, “What support do you need? Check in with me. Here’s the outcome. Go.” It’s next level.

Everyone’s a little different on that. I’ve got partners whose fault is over-delegation. They over-trust people, and then they look in later and say, “What the hell is happening?” They come at the problem from the flip side. But if you hire the right people, I think that’s almost a better model for quicker growth than being overly controlling. My partner grew faster, but I had much tighter ops. And he’s making more money. So there are pros and cons both ways.

Never hire someone to solve a problem you haven’t solved yourself (45:12)

Alex: We’ll do one more off the list and then we’ll wrap. Is there anything else that jumps out from that mega list?

Jake: I love this one: never hire someone to solve a problem you haven’t solved yourself. It’s almost counter to the last one, so I’m wondering where it sits.

But think of the number of startup founders who say, “I have a sales problem, so I’m going to hire a salesperson.” That mistake gets made over and over. Or they try to hire an ops person without learning the ops themselves and building the foundational systems.

If I updated this one, I’d say you need some level of competency in every aspect of the business to hire for it effectively. A lot of business owners say, “I’m not good at that, I’ll just hire somebody.” That doesn’t work. You’ve got to get decent at it first, so you can manage the person you hire.

Alex: I was at a conference two weeks ago, talking to a founder who’s quite early. They make patient-note software for clinicians, more or less, and they sell B2B, into surgical people, practitioners and doctors. They’re looking to make their first marketing hire. She asked me, “What should I look for?”

The first direction I went was: have you sold to people outside the people you know? Because when you launch, you go to the folks you know, and they say, “This is an awesome product.” She said, “No, not really.” OK, that’s a good starting point. Walk the process yourself. Feel how difficult it is just to get in the door.

Then, when you hire, you’ll feel the pain of that problem so much that your view starts to distort. You want a shining light, someone who can come in and save the day. Your Superman.

I’ve seen this pattern over and over. We have a functional gap in the business. We hire someone really competent to fill it. But they don’t have specific experience solving the problem we need solved. Maybe their experience is in an adjacent product, or they’re more of a brand marketer than a boots-on-the-ground marketer. After two or three months, the disappointment wells up. They’re a gun at whatever they used to do, but they haven’t done what you need. And the story becomes, “They were a bad fit.”

I’ve heard that story many, many times. Then my question is, “Had they demonstrated the ability to do what you hired them to do?” No. “And you expected them to succeed in that role?” Yes. OK, let’s play that back. Eventually the penny drops.

Jake: A hundred percent. That’s why you need some level of understanding. Without it, it’s a massive growth impediment.

Take finance. I went through several painful finance hires until I said, all right, I’m going to learn the hell out of this. Now when I vet a new fractional CFO, I know what to look for. I want to see their model, and I get it, because I learned it myself. I went through finance courses. I could do it all. I don’t have time to do it all, but I understand it all, and that makes me way more effective with my fractional CFO.

Same with ops. I had a project manager trying to be the COO of the company, and they didn’t know how to build systems. What that really meant was that I needed to get better at understanding what the company needed from a systems standpoint. My next ops hire was awesome, because I knew exactly what I was looking for. I’d built that core competency and some foundational systems. They were messy and ugly, but they did the job and got us to the first million. Then things start to break, and the ops become a lot of me.

Some people are different. Some people are just better at understanding and finding talent, and if you have that skill, great. For me, I need a strong level of competency in every area of the business so I can manage it properly.

Learning finance the hard way (50:49)

Alex: I remember when you were studying the accounting and finance stuff. You were seeing a whipsawing effect in your revenue and cash, and then you were looking at layoffs. There was a gap in your competency around managing the funds sitting in the business, and it was creating a huge amount of distress, because you’re talking about people’s jobs. Then you put your head down and buried yourself in all this education.

Jake: That’s a good tactic. I’m weak in some area, so let me learn as much as I can. Find the best books. Find an advisor or a coach who can point the way.

The money stuff is super stressful. It’s how I ended up in debt a few times. It’s crazy as you build a business. Your costs are $5,000 a month, and then one day you’re spending $100,000 a month. Screw that up for three months and it’s big. The mistakes get bigger as the numbers get bigger.

I remember talking with an advisor I hired specifically for the finance stuff. He said, “Oh yeah, you’ve got a $100,000 mistake there. I had a half-million-dollar mistake when I learned that lesson.” Those are the lessons you have to learn.

Eventually you have the tools. This is how I look at my finances. I check this every week. This is how I get ahead, so I never end up in that situation again. You start to see things like customer prepays that you’re not tracking properly, or cash you’re not holding aside. Those are the things that trip you up as you go from small business to enterprise. Someone pays you $100,000 for the year, and you need to hold that money. You don’t do that when you’re a rookie. You screw up.

Alex: In these catch-ups I’ve heard about the beast of accrual versus cash accounting many times. It’s a funny one. You start to make money, but you don’t know how to manage the money. You overextend. You hire like crazy, or invest in marketing like crazy. And then: oh shit, a client just cancelled. Oh shit. Oh shit.

Jake: You’re flying blind when you don’t have the tools or the understanding. It’s horrible. You look at the account and think, oh God, where are we? We don’t have money. You can’t comprehend it.

Without that visibility, you can’t tell the difference between “we’re unprofitable” and “we have a customer who’s slow to pay”, or “we just signed an enterprise customer and they take a long time to pay”. I think that trips up everyone as they go through these growth stages. The big customers pay on net 60 or net 90, and that can crush you. That’s why lines of credit become a thing. You’re not used to waiting that long for payment. Enough of those hit at once and suddenly you’re extended pretty far. You need visibility. You need to understand what the hell is going on.

Where to find Jake (54:25)

Alex: A lot of wisdom in this. All right, let’s wrap it. Dude, thank you so much for joining. If people want to find out more about you and what you’re working on, where should they go?

Jake: jake-jorgovan.com is the main site, with all the blogging. And contentallies.com is the other great place to go, to see the full B2B growth agency.

Alex: Right on. Thanks again, man.

Jake: And again, sincere thanks for being my coach. You’ve coached me a lot. We’ve coached each other, and I’ve gotten a ton out of it. Let me drop my recommendation here. If you haven’t worked with Alex, you should work with Alex, because he levelled the hell out of me. I would not be where I am without all the support and guidance. So thank you, man.

Alex: Thank you. Appreciate you, man.