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Welcome to episode #116 of the Morning Upgrade Podcast. In this week’s episode I spoke with Jack Tompkins, owner of Pineapple Consulting Firm.

Top Talking Points

  • Having structure in some parts of your day, but not all the time.
  • Getting a solid foundation with your side project before leaving your main job.
  • Knowing when a client is too much of a drain on your time.

Resources & Links

Connect With Jack at pineapplecf.com or LinkedIn.

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Thank you for listening to this episode of the Morning Upgrade Podcast. If you enjoyed my conversation with Jack, be sure to subscribe to the podcast and please leave a review.

Episode Transcript

Announcer  

Welcome to the Morning Upgrade podcast with Ryan Cote, where we feature casual conversations with entrepreneurs about personal development and growth.

Ryan 

Hey, Jack. Welcome to the Morning Upgrade podcast. How’s it going?

Jack  

Doing great, thanks. How are you?

Ryan  

I’m doing good. Yeah. As we record this, it’s August, and the heatwave in New Jersey finally broke. It was, like, brutal for two or three weeks, and it was the summertime. But this was, like, going out for a walk for 30 minutes and coming back, soaking wet, kind of heat. So it finally broke.

Jack

I understand that in the Carolinas, we get a lot of humidity for about five or six months straight. And it’s brutal to go on a walk outside.

Ryan  

Yeah, so you’re no stranger to it. So Jack, let’s kick this off. Let’s tell my audience of morning upgraders who you are and what you do for a living, and then give us a big win that’s happening in your life right now.

Jack 

So Jack Tompkins again, Ryan, thanks for having me on, and I very much appreciate it. But I run a company called Pineapple Consulting firm. So we are sort of your outsourced analysts for small businesses. So anything from, you know, fixing Excel tools to building full web-based and automated dashboards? I love everything, data, analytics, and data visualization. It’s been a fun ride so far. Recently, when company wise actually brought in an employee just a couple of months ago, and she’s killing it. We’re growing the team is a really exciting time to be scaling and growing. And I’ve always loved managing people. So it’s been a really fun journey.

Ryan 

How did you get into this business to seem kind of like a niche company?

Jack  

Yeah, that is a very good question. Right? Who the heck grows up was like data visualization. That’s, you know, that’s what I’m gonna do. I worked corporately for a while and really liked the analytics piece of it. I was frequently in the spot where I had to present to, you know, like the CFO of the division, or like my boss’s boss’s boss or something. And I’d get in there, and they’d asked me for this huge request, and I’d have three minutes to talk about it. So I ended up just making dashboards. And here’s my analysis. Here’s what I did. Here’s the end result. And they were able to pick everything up within 10 seconds, asked me the question they needed, and boom, done. super efficient, really effective. Those are really good insights, too. So I love that I did not love a corporate world, but love that piece of the work and figure it all right; I bet small businesses don’t really have access to that. So let’s put some feelers out there and get a good reception and been doing it for coming up on three years now.

Ryan  

Excellent. And you mentioned that in your when the team, it’s amazing what a good team member can do what a good team member could do. For the business? It’s okay.

Jack 

It is it really is. Yeah, it’s, it’s, it’s fun, too, which is great.

Ryan 

Yeah, it’s like the, what do they say, the small hinge that swings the big door just makes such a big difference. Having the right team in the right seats on the bus. Alright, so let’s go to your morning routine. Tell us how you start your days.

Jack  

Sure, So I am, I get, you to know, reasonable hours, I’d say normally, on an average day, somewhere around like 8 am ish, trying to make sure I get seven and a half hours, which I’m typically working to midnight. So 8 am kind of works. But I try not to have meetings before 10. Cuz I like to have sort of a morning huddle with myself. And what am I doing today, both personally and professionally? And just kind of level setting up a little bit and making sure that I’m kind of clear. I’ll call it to use the buzzword strategy. Make sure that my strategy is good for the day again, both personally and professionally. I kind of start my day slow and then get into a groove. Once the meeting starts. morning huddle.

Ryan  

That’s it. I think that’s like a spin on the morning routine word. I might steal that. Yeah, go for it. You’re working till midnight? So you’re, that’s a long day. Yeah. How do you turn your brain off to go to sleep?

Jack 

It’s pretty much it’s funny because most entrepreneurs have a difficult time sleeping. And there are days where I’m in that, but I’m working, working, working, and my head hits the pillow. I’m just exhausted to the point where my brain is already off.

Ryan 

I guess that’s a good point. I mean, I’m trying to I, you know, people that listen to this, like nice. He’s mentioned this a few times. He’s obviously not doing it. But I’m trying to get to the point where I turn off electronics 30 minutes or an hour before bed like nothing. No TV, phone computer. So hard. But I see the benefits in it. I just haven’t been able to do it.

Jack  

Yeah, I’m not even sure how I would end my day without electronics.

Ryan

Real freedom. physical book.

Jack 

Yeah. Go talk to somebody face to face me. I don’t know. Yeah.

Ryan  

Yeah, this is our all working progress. Right. So Exactly. Right. Obviously, your analytical guy, I’m assuming to be in your business. I’m assuming structure too if I mean, they usually go hand in hand, maybe not, but maybe very structured in your habits, like what habits do you have, are there any today that you really rely on?

Jack  

I’m sort of a weird combo because there are certain things that I’m very, very structured in meetings with my team or meetings with clients; there’s, I know, the exact agenda, and you know, very structured there. For general life things, it gets a little bit less structured. And it’s kind of just whatever the day holds. We kind of run with that. And I’m, I like living on the fly to an extent. So I don’t really stick with a whole lot. I try and work out a lot. I try and make sure I have time to de-stress and maybe just like watching an episode of TV or something. But there are just a couple of key things that I try and fit in throughout the day.

Ryan  

I mean, you work until midnight save the title. I have a lot of time for this structure. Right? Right. Now we’re kind of working out what does that look like feed for fitness.

Jack  

Nothing too crazy. I’ve always just been kind of like a bodyweight at-home gym kind of guy for a while. I live in a complex now that has a good facility. So I do use it a lot. But I don’t do anything too crazy. It’s really just something that’s always been an outlet for me, and not trying to become a bodybuilder, not trying to lose a whole bunch of weight or anything like that. Just really keep focused, and get my heart rate up. And that’s kind of my turn-off my brain for 20 minutes. Half an hour. Kind of thing a day.

Ryan

Yeah, yeah. Working out. It’s okay. It’s like I have like every guest I have on there like most are entrepreneurs, they all work out. You know, I started I’ve been working out since I was a young kid. And I recently started doing Krav Maga, which is like this Israeli combat training self-defense type thing. And it’s, man; it’s pushing me like I had training yesterday where I literally thought I was going into cardiac arrest because that’s how out of breath I was. And it’s been really it’s really pushed me out of my it’s actually been, like a weird thing. Like, where it’s like, its fitness was also pushing me out of my comfort zones was like a personal development thing, too. Because every class is a little bit like what am I doing right now? Kind of thing? Oh, yeah. So yeah, I think it’s a secret weapon for sure. Fitness.

Jack 

That’s pretty cool. And literally a secret weapon with Krav Maga.

Ryan  

Yeah, well, I mean, I’m only five foot seven, so I’m as unintimidating as you can get, and I have three young girls; I figure I’ve got like, I’ve got like a good solid five years. And so I might have to defend them, you know, maybe three, three to five years; I figured by then I can turn myself into somewhat of a, somewhat of a lethal weapon. You know?

Jack 

There you go. Yeah, like a light one, you know, short, but a functional.

Ryan 

Functional. Yes. So let’s talk about your business. So you’ve been around, you said, for three years, talk us through, you know, maybe there’s a new entrepreneur listening, or they’re thinking about it. Those first few years here. It’s very rough, like how’d you get it? What did you encounter in terms of challenges? And how did you push through them any tips?

Jack 

So I started the very beginning of COVID, like April 2020, when I went full time. And I was doing it on the side for a bit before that. So by the time this airs, I’m sure it’d be pretty close to three years. But a whole lot of challenges, right? I mean, COVID aside, it was just starting a new business. I really like Excel, who else needs it kind of thing. And, like, that’s not really a marketing pitch. So developing, developing a talk track and some sort of marketing plan around the stuff that you love. That’s like the main part of your business, because everybody gets into business because they’re really good at doing their thing, making their widgets or providing their service, all the other stuff. And suddenly, you kind of have to figure it out on the fly. And I’m a big test and try kind of guy and do some A-B testing and figuring out what works and also what I like. So that’s specifically, finding a good talk track was a very difficult thing for me. And I ended up just getting into a group where we had to present every single week. And kind of like what you were saying with Krav Maga pushed me out of my comfort zone and pushed me to actually make sure that I had something consistent to say that was digestible and would resonate well with people that I actually want to work with.

Ryan  

What’s the first thought that comes to mind? Like what’s the biggest challenge you’ve had to overcome so far? And how did you do it?

Jack 

Scalability? So I provide a very customer service, a little background; I don’t have anything that is just plugged and play. Every single client has a new dashboard, or a new piece of analysis, or something like that, which I love. And I really want to stick with that. Scaling that is very difficult because it all comes back to time. And how do we get more efficient? Obviously, you could bring on people, and you could do some repeatable parts that transfer from client to client, but getting as efficient as possible and working with the right clients has been what I would kind of call it the key to my scaling so far.

Ryan 

So true. So with our family agency, Ballantine, it’s the systems and processes for sure. Very important, like we just moved over from Trello to Monday with a very specific config duration, and the team seems to be liking it much better now, maybe it’s brand new, but I really think it’s going to help a lot. And then you’re right, like the clients, man, the right, the wrong client could just destroy you, you know, such a time suck. Right?

Jack  

Right. It is, and like I, you know, have dashboards, my own track hourly rates for those clients. Because a lot of them feel like time sucks, and a lot of them are, but it’s important to do kind of like the data check, if you will, of, are they actually spending a whole lot of time and for the ones that truly are? Most of them are? Then you have the conversation of okay, you know, we might need to raise rates are changed the agreement, or, or just or just part ways, right? There’s, that’s not really a bad ending. It’s just a possibility.

Ryan  

Yeah, we track our time on time sheets. And I say that they’re a time suck. I mean, it doesn’t mean they’re a bad client. They’re just not a good client, for us, like sometimes this is not a good match. Like, they might have a method to find another agency where they just click better. And it’s just a better marriage. You know, the way it is, I’ve really changed my mindset on the few who agree with this, but that clients, but it’s a win-win, you let them go and help and let them find some that are a better fit. Because the team is happier. It’s, it’s actually a win. Like it’s a, it’s addition by subtraction. In those cases.

Jack

It’s such a good point that somebody told me really early on you won’t truly be a consultant until you fire your first client. And it’s so true because you’re to your point, right? It’s an addition by subtraction, which is the math part of me is all flustered by that, but it’s so true in real life.

Ryan

Guys, does that make sense? So let’s go to the opposite side of challenges. It’s all about the winds and growth, like what’s anything, anything, again, to entrepreneurs listening, or new ones are thinking about it? Growth? What have you had the most success with in growing and getting your first set of clients?

Jack 

Absolutely. So a big thing that I did was actually changed, my business model. And it wasn’t a really crazy pivot. It was just; it was kind of just refining the goal. So I would start off with very simple like, Hey, let me work in your Excel. And super easy, you know, I could do a job for like 500 bucks, but that obviously isn’t really sustainable. And so I kind of changed what I was looking for of, let me not only just go build some little thing in Excel, but let me do the dashboard online, let me make it web-based. Let me do all the data stuff. And it’s almost like a vertical integration type thing, where from start to finish, we help you out. And it ends up being that most people have heard of like a fractional CFO and stuff like that. Basically, you have outsourced the CFO, right? We’re kind of fractional analysts. So give us all your analytical needs, and we’ll continue to do it with you; it’s an ongoing process, and we’ll have a couple of projects going on at the same time. And that offering one has been a really good success for the business, but too provides a lot more value for the clients do. So to any entrepreneur listening. Just because you’re getting paid more for longer doesn’t mean that you’re just sucking money from the client. It can actually be a hugely beneficial thing to both parties.

Ryan  

I mean, I know we’re always changing our services and getting rid of services that are fit or aren’t profitable. So like, it’s like an evolution. But how did you know to test that that model is just you’re just trying new things and and it clicked, or was there someone that mentored you on it,

Jack 

it was really a tested-out kind of thing. I didn’t have a mentor to go through it with, unfortunately. But I did look at a lot of people who were like fractional CFOs, and stuff like that. And their model made a lot of sense to me. And it was very much Hey, I’m not an expert in this. So I’m going to bring on a fractional CFO who is an expert. And we know that it’s going to take five or six months to really see some change, Maldis. And I was like, I totally understand that. Why don’t I just do that for myself? And so I tried it out first few clients, all loved it, and it’s worked well.

Ryan  

Got it. Do you have a mastermind that you belong to that you can bounce ideas off of? Just curious.

Jack 

I did for a while. I change it up and do some more kind of one on one coaching now. But I do have a couple. I guess I would call them like key contacts with people that I keep up with every now and then. And honestly, they’re more friends than business partners. But there’s still just looking for that intellectual conversation. And it’s helped.

Ryan  

But you also invest in coaching for yourself? Yes, yep. I don’t do the coaching. I might have had coaches in the past, but I do. I have a few masterminds that I belong to, so it’s sort of like, I guess, kind of group coaching in a sense, so important.

Jack 

It really is, and business coach, they’re like really good referral partners for me, and I see what they do for clients of mine and and their clients. And, again, it was one of those, like no dumb moments when I hit myself in the face kind of thing like, why don’t I just do that for myself?

Ryan  

I have one last question for you. And then we’re gonna wrap up with you telling everyone how they can learn more about you. My last question, you know, we’re gonna go back to personal development ish topic, through the lens of Jack through your experience, and thus far, all the experiences you’ve had. What is the meaning of life?

Jack 

That’s a heavy question. I hope this isn’t too generic. It’s really just about being happy. And it’s, it’s who you’re with what you’re doing. And there’s, there are some really good talks on it. There’s actually a comedian. Daniel’s loss was a really good jigsaw puzzle analogy. And it’s just fulfilled in every aspect of life, and actually contributing back to the economy, the community, whatever it is that you’re really passionate about doing, as long as that contributes back and helps other people out. I think that’s kind of what we’re all striving for, in some sense or another.

Ryan

And I don’t think there’s a basic answer at all. I mean, I think it is happiness as I get older; I’m 43. Now, so statistically, halfway over and happiness, fulfillment, having fun, me, I’m going to work hard, make money, great impact, all that stuff. But the fun and Happiness Equation, I think, is just really, really important. Because otherwise, like, what’s the point? You know, if you’re like making a lot of money, you’re doing X, Y, and Z, but you’re miserable. It’s, like, it doesn’t make sense. Like, what are we doing here? You know, and so I think that answer is actually perfect.

Jack

Perfect. Excellent. I appreciate it, man. I guess more about me, right? That’s what we’re on.

Ryan 

Yeah. Yeah, did Yes, share it, share whatever you want to share, website, whatever you wanna share? Then we’ll wrap up.

Jack 

Perfect. website is a great place to learn more about what we do and a bit about me too. And that is www.pineapplecf.com. And that’s abbreviated for pineapple consulting firm.com. I’m also all over LinkedIn all the time. If you want to connect, seriously reach out to me, and let me know that you heard me from this podcast kind of thing. And I’d love to connect. So thanks again for having me on. Ryan. This was a blast.

Ryan  

Yeah, it did a great job, Jack. I just want to ask you one more. One more thing. Why pineapple? What’s the story there?

Jack 

There’s a whole video on my website, but the short answer is southern hospitality. And a sort of vacation feeling that comes with pineapples.

Ryan  

Very nice. Okay. Excellent. Look. Great job, Jack. Thanks for everything you shared.

Jack  

Thanks so much, Ryan. I appreciate it.

Announcer 

Thanks for listening to the Morning Upgrade podcast. Please subscribe and review. And don’t forget to visit us at morningupgrade.com for more content.

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