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Hey, what is up?
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Welcome to this episode of the Wantrepreneur to Entrepreneur podcast.
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As always, I'm your host, brian Lofermento.
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There's one thing about realtors that we all know, that they all say, and that is location, location, location.
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Well, in the world of entrepreneurship, I would argue that those three words we should repeat over and over and over are systems, systems, systems.
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We are going to live by or die by the strength of our systems.
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That's why I've personally been so excited to have today's guest, an entrepreneur, on the show, because she is the systems queen.
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She's going to challenge us to really elevate the game that we're playing when it comes to our systems, our processes, our operations.
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If you're hearing that and thinking, brian, I don't have any operations.
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Well, that's why we are joined by the very awesome Natalie Gregorian.
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Let me tell you all about Natalie.
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Natalie helps entrepreneurs make their biggest impact without getting trapped as a prisoner within their own business.
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She's a fractional COO, that's chief operating officer.
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Again, if you don't have operations, natalie's gonna open your eyes to that.
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She's also a ClickUp expert who's helped over 75 entrepreneurs remove themselves as the main bottleneck of their business, to scale to multi, six and seven figures and win back the freedom that they started their business for in the first place.
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I love the way that she talks about all of these things.
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We're all in for a treat today.
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We're going to learn a lot, so I'm not going to say anything else.
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Let's dive straight into my interview with Natalie Gregorian.
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All right, natalie, I am so very excited that you're here with us today.
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First things first.
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Welcome to the show.
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Thank you so much, Brian.
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Thanks for having me.
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Heck, yes.
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Well, we are going to counteract that location, location, location that we hear from realtors, and we're going to implement systems here in today's episode.
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But before we get there, take us beyond the bio.
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Who's Natalie?
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How did you become the queen of systems and all this cool stuff that you're up to?
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It is sort of a long and stumbling story because most operators I know never decided as a little kid I'm going to go into operations.
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That's just not a thing that happens.
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Most people stumble into it and that's what happened to me.
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I've actually been working with entrepreneurs for just about a decade now.
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I started my ops career running operations for this like mastermind networking community of bootstrapped entrepreneurs and we would put on these big events all over the world.
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Like we got 200 entrepreneurs to a private island in Croatia and so that was.
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My job is to get people on planes and trains and automobiles and speedboats and ferries and get them all in one place so that they could learn how to grow their businesses, which was a really, really cool first dive dipping my toes into entrepreneurship.
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I never thought that I was going to be an entrepreneur, but all these people they were paying $10,000 to be in these rooms learning how to grow their businesses and it was my job as this little baby, 21 year old, to sit in those rooms and take notes so that we can distribute it to the guests afterwards.
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So it was literally my job to sit there and learn, which was the coolest job in the world, and what I found is that all of these business content sessions were so focused on growing your business.
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It was very front end focused big sales, big marketing and that was awesome.
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But then afterwards, after the content, you know, we had 200 entrepreneurs sitting down to dinner and talking about what's going on in their businesses, and every single one that I heard was, yeah, sales and marketing are going great, except for the back end of our business is in complete chaos and disarray.
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And so what I found is that there is a and this is not a knock on this particular event it's, I think, a failing of the entrepreneurial coaching community in general general, that we don't have enough talk around what happens when your front end marketing and sales are successful.
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What do you need to implement in the back end of your business in order to maintain that success so that your business isn't on fire, your team's hair isn't on fire, your hair isn't on fire trying to manage it all?
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And so I realized that this is a huge gap in the entrepreneurial community.
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So, from there, I became an operations consultant, working with six, seven and eight figure businesses and, surprise, surprise, they all had the same issues While, like their Stripe, screenshots of their revenue show that they were crushing it Secretly.
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What you don't see on the back end is that everything is in chaos.
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The team is on the brink of mutiny.
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Their clients are unhappy because there's dropped balls everywhere.
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They're unhappy because they started this business for I don't know for some level of freedom.
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We, as entrepreneurs, don't venture into this journey because we want to be working 10, 12 hour days and sacrificing our weekends, but that's what happens to these founders when they don't have the proper operations on the backend.
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So didn't matter if I was working with a six figure business or a seven figure business or an eight figure business.
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They all had the same problems.
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It just got a lot hairier and uglier and compounded at eight figures than six figures, and one of the main patterns that I saw across all of these businesses was that none of them had a functioning project management system, and that really put a light bulb in my head.
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I said this is where the highest leverage point is going to be for making sure that, as businesses grow, their founders and their teams and their clients aren't suffering.
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This is the place to really, really help other entrepreneurs.
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Yes, I love that overview, natalie, and I'm going to add in I also love the name of your business Tip Top Ops.
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It rolls right off the tongue and, with that in mind, natalie, honestly, when I hear you talk about all these things, quite frankly, as a content creator myself in the entrepreneurial scene, I would argue that it's the entire entrepreneurial content ecosystem that lets business owners down, because there's such a strong emphasis on revenue, on sales.
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You called out I love the shade that you threw on those striped screenshots that we see all the time, and you're right, it is so deceiving because we think that that's where we need to focus, and I love the fact that you bring us that real life transparency behind the scenes of these businesses.
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So, natalie, I'm going to put you on the spot in a super broad way here to kick things off, and that is what is operations?
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For listeners who are saying, gosh, a COO?
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I mean I'm not the COO, I don't have a COO, I don't even think about the O in there, I don't have operations.
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What is operations?
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What are these fundamental elements that we should be focusing on that all of our businesses should have to support the back end processes businesses should have?
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to support the back end processes.
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Operations is the, the optimization of really a couple key things across your business.
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It is making sure that you are making the most of your time, you're making the most of your energy, you're making the most of your money and you're making the most of your resources, and those resources include your team.
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Without all of that, what I've seen is you're just brute forcing your way through business, and that's a really, really hard way to do business.
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I worked with.
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It was an eight figure marketing agency and on the surface, things were going great, tons of revenue coming in right but everything was brute forced.
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Everything was so much harder than it needed to be.
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It doesn't have to be like that.
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When you have operations, everything becomes so much smoother, so much easier, and you're able to scale not only more quickly but also more sustainably, and that's the big part here.
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Yeah, I love that.
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It's funny when I hear you say that I'm a tech geek, so I my first thought is let me have tech support me in these efforts.
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And I know that you obviously are a ClickUp expert.
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I would argue actually, natalie, you probably know this far better than I do A lot of businesses don't really have a project management system to support them.
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We've all heard of companies like Asana.
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I view that I'm sure you view it a little bit differently.
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I view it, or at least I treat it more like a to-do list.
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I think that the powers of ClickUp I'm a big fan of Notion for example, these project management tools, they can support us, they can set us up for success.
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Talk to us about the importance of that project management system and how it fits in with that overarching view of operations that you gave us.
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So I love what you said about it's really just a fancy to-do list, right?
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Well, that's part of it, sure, but that is just scratching the surface.
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I was working with a client he's one of my favorite clients.
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He was running a seven figure business group coaching program and it was pretty much just him running it and he was getting really burnt out, really overwhelmed.
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There were so many balls that he had to juggle to run this incredible business and he was actually becoming resentful of what he had built.
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He was starting to think is this really what I want, and should I start disassembling it?
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Should I burn it to the ground?
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Because I'm working more than I want?
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My brain hurts all the time, I'm stressed out and overwhelmed all the time, and so he asked me to come in and take a look at what's going on.
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Turns out he's running his entire business off of sticky notes on his desk.
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There's some like Google sheets thrown in there here and there, but it's mostly him holding everything in his brain.
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One and anything that lived outside of his brain was was in a context, in a platform, in a channel that no one else could access.
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So when he was thinking about gosh, I would really love to delegate.
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I'd really love to bring on a team.
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I don't want to be doing this all by myself anymore.
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I don't want to be wearing all of the hats anymore.
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Well, he was incapable of passing that on to anyone else unless they were physically sitting next to him at a desk in his office, in his home.
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And in this post-COVID era of everyone working remotely, there's so many better options than that.
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Yeah, when I think about all those better options, natalie, I go straight to automations, apis, integrations.
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We all have a million tools already, so we need to get those tools to talk to each other.
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That's me again coming back to the fact that I love tech.
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What is that typical nature?
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Post-it notes aside, I'm sure that that guy probably needed a lot of help to get that into the tools that will support his business.
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But I think what a lot of people miss out on is the fact that these things can roll up together.
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There are so many ways that they can work together, because I'm sure that's one of the big obstacles, as people say.
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Well, you know, my email happens in this platform and my sales register here and my website analytics are in a completely different silo.
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Natalie, is that part of it?
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Is it taking all of these things into one place?
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I'd love to hear where's that love for ClickUp?
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Just use that as an example of project management software, because obviously you're very adept at that.
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Where do you even start making sense of all the happenings inside a business?
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The beautiful thing about.
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Of course I love ClickUp so much, but any project management at its core.
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It should be the single source of truth for your business.
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It should include all of the to-dos, all of the activity, all of the projects, all of the data that you want to be tracking in your business and to your point earlier around.
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It's not just a fancy to-do list.
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To-do list.
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You should be aggregating data across how, not only like your client fulfillment how are you actually doing, what is the performance that you're getting for your clients but also how is your team doing, what is your team's productivity look like?
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But it is also the data tracking tool that is going to help you make better database decisions in your business, and that is again where that scaling becomes so much easier and so much quicker, because you're not making decisions based on your gut, because that works up to a certain extent.
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But once things start growing beyond what you can hold inside of your brain and inside of your gut, you really need data to be able to make those good decisions, and so a good project management system should be what is helping you make the next step in your business, based on what you're seeing in the performance of each department that you're running.
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All of that is held within a project management system and all of that works towards helping you, as the CEO, scale more quickly and scale smarter, so you're not brute forcing your way through any of it.
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Yeah, so well said, natalie.
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I'm excited to go here with you because I'll tell you this One thing that I really admire about your business is the fact that you create custom click ups from scratch, and I think that to me, the zero to one, that's the hardest step, because, to go back to the post-it note example, our businesses are a mess a lot of times behind the scenes and to make sense of it after the fact is much more difficult than hopefully.
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This episode is catching people at the very beginning and they can start doing it correctly, but for those of us who haven't, who we do have to go from zero to one and architect it after.
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That's actually the verb that I want to pick on, natalie, because it's something that I saw in your messaging is you architect custom click-ups?
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Talk to us about the importance of that, because starting from scratch a blank canvas, I would imagine is the most intimidating part.
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Where the heck do you start?
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Because while you're doing the technical side of things, your business and strategic mind is at work, trying to make sense of their operations, whether they've made sense of it or not.
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Yeah, I will say that most entrepreneurs are not operators in their brain chemistry and brain structure.
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That's just not how they think and that is okay.
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Like you, not being an operator is not going to affect your ability to grow a thriving business, your ability to be a visionary and a true entrepreneur.
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That's what counts, and you have a lot better things to be doing than trying to figure out how to create your own click up system.
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Like that's just not a good use of your time.
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I've seen entrepreneurs who try to figure it out themselves and they end up just like wasting a bunch of hours on YouTube and creating something they're not happy with anyways.
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So I would highly recommend don't waste your time on that.
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Definitely bring in help.
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That's something that me and my team love to do.
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We love to play in it, and that word that you're using, brian, that like architecting word, is really something that we take pride in.
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We look at what is important for your business specifically to be tracking.
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What are the processes specific to your unique model and your unique fulfillment process that we need to be taking into consideration.
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What is the vision that you have for how you want to grow your business and how can we tangibly translate that into a system that is going to support and enable that.
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So when I introduce myself into a system that is going to support and enable that.
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So when I introduce myself, I often say that I am an architect, because one of the beautiful things about especially something like ClickUp is that it's so hyper customizable.
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You can build anything under the sun, and that's a little overwhelming to people, especially these visionaries and entrepreneurs who are not operations minded.
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But when you have a savvy architect on your side in your corner, that unlimited possibility of customization is more like a playground.
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It's more like a sandbox, and so we can design it to be whatever it needs to be to work for your business specifically.
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Yeah, natalie, and even hearing in that answer, you talk about a very key role that has to exist within a business.
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You talk about that operator role and I want to broaden our conversation and zoom way out, aside from just the project management system and tool that we use, obviously, you serve also as a fractional COO to other businesses.
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I want to talk about that role in and of itself, because a lot of people we all know about CEOs, we all know about CMOs, people love talking about marketing and sales and all that fun stuff that falls under there.
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What is that key in that core role that a COO plays inside of a business?
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Yeah, I will say, even like your listeners may be intimidated by the I don't know the title of COO, most businesses starting out don't need a COO.
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Most businesses starting out could really benefit from even someone like an operations manager.
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So you don't have to give away that C-suite title right away.
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I would say, in fact recommend, that you don't start someone where you need them.
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The operations manager is going to take so much time and mental energy off of your plate, because what's important, especially when you're first starting out, is that you are truly serving as the front end of the business, you as the founder.
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You should be focused on sales, on marketing.
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That is your most valuable use of time.
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Your most valuable use of time is not streamlining things on the back end.
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That's not something that has to be done by your brain specifically, and so if you can bring someone on who does have that brain wiring, that DNA, to look at something and say I know how to make this a thousand times more efficient, that's the kind of person you want in that role and that's the kind of person you want owning the optimization of your time, your energy, your money and all of your resources.
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Yeah, natalie, I love the fact that you called out and you openly acknowledge the fact that our needs are different.
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When someone's just starting out and they have $0 in revenue, of course you know not only do they not need a COO, but they probably or definitely cannot afford a COO.
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So I love the fact that you acknowledge that and I that's one of the things that really caught our eye when we came across.
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Your business is right there on your website you call out you've probably outgrown and then you've got a list of bullet points working endless hours and yet always feeling behind the conflict of not being able to increase revenue without also increasing your workload.
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And, natalie, I know for you personally that comes from.
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You've experienced all different sizes of businesses, types of businesses six figures, seven figures.
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You mentioned eight figure businesses, and so I would love to hear your perspective on those different inflection points or milestones that businesses go through, because I would imagine, in the operational projects that you work on, sub 10K a month business probably has very different needs than $100,000 a month business.
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So what are some of those differences that you focus on, depending on the inflection points that you experience with your clients?
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Yeah, the irony, like you would guess, probably, that an eight-figure business needs a lot different things than a six-figure business, and there's some parts to that, some truth to it, but the reality is that they need a lot of the same things.
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They just need it much more urgently and it's more painful for them.
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So that's why it is so important and I feel so strongly and I want to help entrepreneurs and founders who are just starting out to do it right early on, because even if you get to six figures, even if you get to seven figures and eight figures, you're going to have the same problems.
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They're just going to hurt a lot more and I hate seeing entrepreneurs in that much pain.
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So, absolutely, if you can get it done earlier rather than later and some of those big things, even if you're sub 10K, you have client onboarding that can be templatized.
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You have client offboarding that can be templatized.
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You may have some sort of VA or executive assistant helping you and they need to know what to do every single day helping you, and they need to know what to do every single day and you don't want to be the glorified babysitter nagging them, saying, hey, did this get done?
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Or hey, what's the status update on this.
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You have better things to do, and so that is again where these systems and project management can come in handy is it can take all of that managerial load, and I've seen it give entrepreneurs back 70% of their time.
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They don't have to be babysitters, they don't have to be unwitting micromanagers.
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They can let the system do all the heavy lifting so that they can get back to doing their actual jobs and their team, as they grow it, can also get back to doing their actual jobs.
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There doesn't have to be all of this back and forth communication that just ends up wasting everyone's days.
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Yeah, for sure, natalie.
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It's so cool hearing about the what behind what you do, but I do also.
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While we have you here on the air today, I want to talk about how you do it, because I'll tell you what.
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I interview a lot of entrepreneurs and I see a lot of websites and the ways a lot of businesses are structured and a lot of offers, but what I really love about the way that you serve entrepreneurs is your scalability accelerator.
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I think it is such a brilliant way that you've structured the way that you serve people.
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Please, you're gonna explain it way better than I can from the summary on your website.
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Talk to us about what is that scalability accelerator?
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I wanna hear behind the scenes of how it works, how you've structured it.
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Listeners, it's a 10-week mastermind.
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It's really cool the way that Natalie has boiled all of this down.
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So, natalie, what's your scalability accelerator?
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Talk to us about that, so that that is a version of my fractional COO process that I take one-on-one clients through.
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So most people um, most people may not need that one-on-one attention with me, but they still need the tools and the resources and the templates in order to get all the things done.
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So what I've done is I've essentially packaged up a, a one-on-one experience, and given it to people in a group context, which, honestly, I think works almost better, because then it turns into a mastermind.
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There is peer-to-peer accountability and peer-to-peer support, and so really, what we do across those 10 weeks is we?
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Well, there's a couple of core things.
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One is we make sure that we are optimizing your time, because your time is the most valuable in the entire company.
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So we are using data, of course, because we love data, to find out what is the highest leverage first hire to make, and then we make sure that you are able to go get a rock star hire to take over all of the jobs that you hate, anything that is sucking your time and your energy.
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That's going to be the first thing that we offload.
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You hate the things and they love the things, so we get that person in place, then we install one super simple operating system to manage your business for you.
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That is the project management system.
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We get that online and running so that you don't then spend all of that time.
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You've just won back micromanaging the person that you've brought in.
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So that's really important.
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And we make sure that you have all of the communication rhythms, all of the feedback loops and all of the data in place to keep growing scalably and sustainably, and so all of that happens in 10 weeks.
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We work fast, we make sure that you are getting results fast and, essentially, you get all of my templates, all of my resources, all of my support handed to you on a silver platter so that you can go and execute and you don't have to waste time figuring it out by yourself yes, I love the way you've laid all of that stuff out.
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Natalie, I want to interject this.
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I think it's really important.
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I can't believe neither you nor I have mentioned it here on the air today.
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A lot of people will probably be listening to this saying gosh, it click up sounds really powerful and that's a project management system and it's this big piece of software that's going to integrate a lot of things and it's going to have all this data inside of it.
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Natalie, you and I know the entry price point for it, but a lot of listeners probably think that it is outrageously expensive.
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Talk to us about the pricing structure of ClickUp.
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Do we have to go to that paid version, which I just did?
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A little bit of a spoiler alert of how much does it start at?
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What's your recommendation when people enter that world?
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Well, guess what, brian?
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Clickup starts at the big old grand price of free.
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There is a free version and that can take you, honestly, pretty far.
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Even if you do upgrade to like the first tier to get a couple more features and functionality, you get the most functionality at the lowest price.
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Compared to all of the other project management platforms out there, even something like a lot of people really like Asana.
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They come to it as sort of an entry point.
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Asana is one of the most expensive platforms.
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So that's why I like starting people on ClickUp is because it is so approachable at the grand price of free and then, when you are ready to upgrade for increased functionality, it's really, really affordable.
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Yes, I'm so glad that we put that in there because listeners will be mind blown.
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Natalie, I love that you stress the fact that you can go far with that free plan.
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This is not one of those tools that you'll use in your business and realize I can't do anything in here unless I pay Genuinely.
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I'm sure full-on businesses, multiple, six, probably even seven-figure businesses, can operate on that free tier.
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So, natalie, while we've got you here, I also want to open the floor for you to talk about the tech stack that you've seen supporting so many other businesses as well as your own.
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What are some of those other tools that you really enjoy that plug in nicely with the things that you build out in ClickUp or just the things that really support your clients and your own business behind the scenes.
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Such a good question.
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So for sure, of course, clickup is the one that I suggest for everyone Other tech stacks that I really like, that I will say ClickUp is just not built for, but can play nicely with ClickUp.
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So things like calendar scheduling I use things like Calendly or TidyCal.
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There's even some free options out there, so start there for people booking onto your calendar.
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I would also say that it's not a great like newsletter platform.
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There is some email automations that you can do out of it, but I would say those are better for like one-off things.
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So getting some sort of like email service provider whether that's ConvertKit who's now Kit or ActiveCampaign or MailChimp, anything like that that would be good.
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And I've also seen people you can run CRM type activity out of ClickUp, especially when you're just starting out, but eventually you'll want to transition to something like a legit CRM platform and most people that I work with they end up coming on to HubSpot and that all of those play nicely within ClickUp.
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Yes, I so appreciate that transparency, natalie, and especially a shout out to a good Boston-based company and HubSpot.
