From Freelance to 16-Person Team
Host Troy Trewin interviews Paige Wiese, founder of Tree Ring Digital, about her journey from a post-GFC freelancer to leading a 16-person digital marketing agency. Wiese details the company’s rapid growth, including its doubling during the pandemic, and how it has remained resilient through recent challenges. The discussion offers valuable lessons for small business owners, focusing on the power of prioritization, transparency, financial acumen, and the strategic advantage of being industry-agnostic.
Full Transcript
Troy Trewin 0:00
In 2009 just after the GFC, with not enough work in architecture, you decided to start your own digital marketing business, doubling in size after covid. Dropped a little soon after that, but consistent, 10 to 12% annual growth over most of those 16 years. Started on your own now with a team of 16 full time equivalents. Congratulations on the growth. That’s fantastic.
Paige Wiese 0:19
If you can’t figure out which one’s more important, if you can’t figure out where to spend the time first and then move into the next thing. And sometimes it’s small tasks first, then big, sometimes it’s big then small. But just what’s the prioritizing that you’re doing is really the key. I think our clients really like seeing that too.
Troy Trewin 0:39
G’day and welcome to the grow a small business podcast. I’m your host, Troy Trewin. Each week, we speak with an owner who has grown a business with five to 30 team members to something bigger, diving into their numbers and another thing, the pain they’ve experienced. We explore what they did to overcome each barrier and what they would do differently from day one. Let’s get into it. Welcome everyone. Today, I’m interviewing Paige Wiese from Trewin digital based in Denver, Colorado, United States. Thanks for your time today, Paige, absolutely. Thank you. Let’s start with how we know each other. Barry Cohen from Barry Cohen public relations has sent us a few great guests, and I’m sure you’re not going to disappoint. No pressure. I’ll do my best tell the audience a bit about your business, what it does and how it makes money.
Paige Wiese 1:26
All right. Yeah. So Trewin digital, we are a full service digital partner. We specialize in website development, online advertising, as well as digital asset, digital continuity for businesses, so that they’re able to keep everything together, keep ownership. We see a lot of mistakes and mishaps, and have done a lot of recovery, whether it be website side, marketing side, just why is this not working so working alongside growing businesses, typically, someone that’s scaling, looking to get into a new region, a new market, or preparing to exit, or they could also be looking at more of the M and A side, looking to acquire growth through acquisition. So really, in that growth mode is where our clients tend to fall, which is where everything that we offer really yields to be really good services for them.
Troy Trewin 2:12
In any geographic regions or industries you specialize in,
Paige Wiese 2:16
typically in the United States, we have clients all over the US, some in Denver. We obviously grew the company starting in Denver, so we still have a pretty good base there, but all over. And then from there, we are pretty industry agnostic. We’ve seen that what we do really can apply to every industry. We’re also extremely adaptable in how we do it. So, you know, I like the fact that we don’t stick to one industry, because it allows us to see, like, wow, this is really gaining traction. That’s a new approach over here. Should we try it on a different client that we haven’t been able to quite see the same traction on and mix it up instead of staying so cookie cutter for the businesses along the way? So it’s really yielded a great success for us to be industry agnostic.
Troy Trewin 2:58
I had a guest on about three years ago from Denver. You’re gonna love this. He digital marketing similar to yourself, and he’s a bit of an SEO nerd. Loves it, and wanted to start another business, but not an online one. So he used his SEO skills to identify there was a shit ton of searches each month for, I think it was outdoor spas in Denver, and there were no stores in the town at that point selling them. So he went and started one up. It’s done very well. And then opened another one up in another city not far away, using that data from the SEO, yeah.
Paige Wiese 3:28
I mean, people think it’s got to be one way or another. There’s, you know, like B to B can run differently than B to C, and at the same time, there’s reasons the strategies do work, and so being able to pull which one is the right one for the goals the client is trying to reach, instead of just selling them on a service that they don’t need. But that’s just what we do, day in and
Troy Trewin 3:48
day out. And how did you start out?
Paige Wiese 3:50
I started out doing freelance work. I was actually in architecture before I got into all of this 16 years ago, and was just at a crossroads of what do I do? Architecture is not working out in the US. There was a huge, you know, downturn in the economy there as well. People weren’t building homes anymore. I’ve been laid off twice, and so I was decided to take a stab at creating code and building websites and all of that, and then from there, just continue to listen to clients and adapt. And hey, this is what their concern is. This is the problem. I always joke with the team, like, if we get a call often enough, how do we just stop the call permanently? What do we need to do? What do we need to change? Like, there’s obviously something happening here. So that’s really where we started to, you know, shift and adapt our services as well to make sure that we were addressing that pain point for clients.
Troy Trewin 4:38
So you started 2009 just after the GFC. How are we then, 16 years ago, when you made the jump?
Paige Wiese 4:45
Oh, man. 23 I believe. Yeah. 23 and do you have some
Troy Trewin 4:50
key numbers you can share to illustrate the growth of the business?
Paige Wiese 4:54
Yeah. So at first, you know we are. I was on a pretty decent trajectory over the whole time. Time that I was growing the business, we kept seeing like 10% increase, 10% increase. It was really, really great. We doubled in size as covid hit, and again, just fantastic to see during something like that, for us to be in a space, I credit a lot of that to just being in the community for so long, we had such a good grounding that we saw so many referrals come in that, yeah, we doubled in size, and then from there, businesses have just really struggled getting back on the ground and getting their feet back into business as normal. And so we started to take a dip for the first time about two years ago, and started to see that dip last year as well. And now we’re on the upwards, but definitely in more of a growth mode. But I think it was kind of a needed growth mode, and just kind of pushing us more into an ideal client, instead of, you know, how do we just help anyone and everyone? And what
Troy Trewin 5:50
about number of full time equivalent team members just started with and where you’re at now?
Paige Wiese 5:55
So when I started, it was just myself grinding away freelance, doing all the things I always joke, I made a lot of business because I was the only person that was ridiculous enough to answer the phone at 11 o’clock at night. But it yielded to a lot of business long term and a lot of referrals. And then, as I started to grow the team, we had eventually gotten all the way up to about 12 full time employees, full 40 hour work week employees about two, three years ago, when we were at that height of the growth as well. And then just coming back, trying to hire this space is people can, they can work from anywhere. So we had to kind of even there, adjust how we were handling employment. How did we handle remote work, compared to hybrid, compared to in person, and so taking a lot of look at the business models and what were the options. So right now, we’re down to roughly three or four full time employees, but we still have a team of 16 and most of our contractors, we’ve learned to just build really, really good long term relationships with so that they’re more dedicated to us than, you know, a one off contract, or us just hiring someone on the fly. So, you know, I typically tell people our team is about 16 strong, because we’re just doing a really, really good job of keeping that consistency with them.
Troy Trewin 7:11
That’s great. That’s wonderful growth. When was the moment you felt like you had succeeded?
Paige Wiese 7:16
There was a lot of times early on, you know, it was just like sometimes, just making the right connections and the right contacts of how we’re getting work and whatnot that I remember just being like, God. I feel like this is what it’s like to win the lottery, like things are just going so well. We’re just doing so good. But I think, you know, kind of, one of the times I felt that we hit success was when we started seeing, you know, some of the legal stuff start to come up where it was like, why are we having to call lawyers? Why are we having to have some of these conversations? Like, everything’s just been business as normal, or, I’m just a small business freelance, like, what is this about? And so probably about seven years ago, maybe five years ago, you know, it was just like, Okay, we must be doing something if people think that there’s, you know, money to come after, or whatever that looks like. And so I think that’s another, well, it could have been a very negative experience for us. I really took it is, we’re doing something right? People think that we’re worth more, or, you know, have something behind us to go after, instead of, you know, a lot of freelancers, people aren’t even going
Troy Trewin 8:21
to try. Never had anyone answer that question that way. It’s really interesting.
Paige Wiese 8:26
I was, I was like this. I mean, you got to look at it as a win, though, right? Or it’s a really good example of how to take such a negative and turn it into a positive. And, you know, I know I had to have that conversation a lot of, why would you come after me for something like this, when it’s really not that big of a deal, but you clearly thought there was something here, and you know, rightfully so, we had grown the business to a really good size, and so it made me just, yeah, we’re doing something
Troy Trewin 8:54
right? What does success look like to you?
Paige Wiese 8:58
Success for me, looks more, though, like just really, really great quality out the door, really listening to our clients, really collaborating with our clients, and having a well rounded team like our team right now is fantastic. They want to help the client. They don’t care what the question is. They want to find an answer, and they all want to communicate and collaborate internally, to love. I’m not the expert here, but this person is, let me go call them, let me slack them. Let me get in touch with them and get the right answer for the client. So for me, it’s just like when all of those pieces really start falling into place. As far as we’re putting really good quality out the door, even at a higher capacity, we aren’t just, you know, churning and burning. We’re really looking to build long term relationships with the clients that they know they can come to us for literally anything. That’s why I said digital partner at the beginning is, you know, come to us. We are a resource for you, not just something where you have to figure out, how can I go to the internet and find the answer, but. Us an email. We’ll have that for you right away. So for me, it really is, how are we producing work out the door and delivering for our clients?
Troy Trewin 10:08
Perfect question for you. Number one thing you’d recommend to marketing a fast growing business,
Paige Wiese 10:13
have a strategy and keep track. Know what you’re doing, know what metrics you’re going for. What’s the goal? A lot of clients come to us and it’s, you know, we’ll get the phone call. I want to run SEO because my cousin said I should be doing SEO. Okay, but what’s your goal? Is SEO really going to help us achieve that goal? Or if they want to grow quickly, same thing. What does that budget look like? And how do we want to diversify that budget to make sure that we’re putting the right pieces in place. Way too often I see clients just aren’t tracking the right metrics. So it’s really, really easy and quick for them to say it’s not working, when, in reality, they don’t know what they’re tracking.
Troy Trewin 10:52
Yep, absolutely it’s one of my bug bears. And one of the early things I talk with owners about is just start tracking some simple numbers around your marketing you know, understand lifetime value, LTV of your customers, and customer acquisition costs, the two key numbers in that ratios, which I’m sure you’re well aware of as well,
Paige Wiese 11:09
and I’m sure you’ve seen far too many not know those numbers. We get on calls all the time, and as we’re deciding what to do, we’ll start asking that, and the answer is always, I don’t know, and it’s like, I want to run marketing for you, but we kind of got to get to what is the best profit margin for you? What does this look like? What kind of budget can you actually spend? Should you be spending to get that acquisition cost back and everything? And so, yeah, if you can know those things up front, or you know really early on, you’re going to be way more successful than a lot of other businesses that are just saying, I want to run marketing, because I know I need to run marketing.
Troy Trewin 11:46
How did you fund the business? Funding was 100%
Paige Wiese 11:50
myself, just grinding and hustling. I’ve been a really big advocate for investing back in the business. So anytime that you know we’re seeing more of an upswing. How do I put that back into whether it’s a stronger team, whether it’s additional resources, whatever that looks like. So all self funded the whole
Troy Trewin 12:07
way. If you were to start up today with plenty of funding, would you go into your industry?
Paige Wiese 12:12
I love my industry. So yes, I mean, I think there’s, I always joke. There’s like, side things that I think could be fun to do. But I it really opened my eyes to how much I love business and how much I really love talking to business owners about business models, business strategies. Why are they doing it this way? Oh, wow. I didn’t realize you could make money doing that and just such a fun area that I’m I probably would. I think it’s also been a good catalyst to a lot of what I want to do long term career of having this strong background really yields for me to set myself up to invest in other businesses, or to, you know, be on advisory boards and different things where it’s a really strong suit to bring to a table.
Troy Trewin 12:58
Can you outline the most stressful point in your small business growth journey so our audience can learn from it.
Paige Wiese 13:03
Yeah, most stressful point, it’s small business, it’s it’s a roller coaster. It’s up and down, for sure. I think that’s part of just what has gotten me here, though, is the resilience. To say, keep going at it. But I think one of the hardest parts was like, I mean, the last two years, honestly, I mean, I’ve been in business for now 16 years, and I’d say, yeah, about 14 years in is when we started to see the dip. And it’s, it’s stressful, it’s defeating. It’s why am I doing this? I’ve been in it for this long, and now we’re starting to see this happen. And, you know, really having to pull yourself back and go, you have to look at all of the other circumstances surrounding you. Or is there something that we do need to fix internally that would, you know, help prevent some of this? We’ve had to do a lot of pivots along the way right now, even more so of you know, we do WordPress websites, we specialize in it, but there’s a lot of competitors coming out quickly with do it yourself, AI builders. And while it’s still not amazing tools, like it’s a buzzword, you know, people start asking and wanting to know, and so how do we stay at the forefront of it all and continue to educate and learn so that we can have those conversations with the client? But you know, I think those times start to get really, really hard when you just every time you feel like you’re turning something over, it’s just not clicking, and you know that it should be clicking, it’s you’ve done it for so long. So definitely, I would say the last few years has been one of the more stressful
Troy Trewin 14:34
parts I heard on a podcast the other day. Almost half of the world’s websites run on WordPress.
Paige Wiese 14:39
Yes, it’s a very, very high I think the only other one that’s kind of close is like Shopify takes over a lot more e commerce than ever before. WordPress just hasn’t done a fantastic job staying up on that. It’s still a great tool for us, because there’s a lot more custom code we can do for those more technical e commerce clients. But beyond that, a WordPress has, by far, always owned the market is in website builds.
Troy Trewin 15:06
What area in business do you feel you’ve had to work on the most to add the greatest value?
Paige Wiese 15:11
Oh, I think finance is probably one of the ones. It’s always the the trickiest, the hardest. You know, like, do we have the funds for this? Are we making sure we’re keeping track of how much we’ve spent in website add ons, and are we paying for those or the client paying for them? And are we staying within the scope of work? Are we losing money? Are we making sure that, you know, we are quoting appropriately, that our team is invoicing appropriately? How do we really tighten all of that up. So I’d say finance has probably been the area for me that is been the most stressful, compared to, like a lot of business, I say is pretty second nature. It’s pretty easy for me on the rest of it.
Troy Trewin 15:52
What have you enjoyed the least about managing fast growth?
Paige Wiese 15:55
I love it. I work better under fast growth. I work better under just heavier, higher circumstances. I joke anytime we’re slow or I’ve got even a day of what am I gonna do? I am the laziest person. And if we are busy and, you know, go, go, go, I am right there. Let’s just keep this thing moving so I like it more than I hate
Troy Trewin 16:18
it. What do you love most about growing small business, most
Paige Wiese 16:22
just that everything’s a little bit different every day. There’s a different challenge. There’s so many ways we can continue to drive business. There’s so many opportunities, as long as you’re looking at the right areas and just the strategy behind it all. And I think also moving from like freelance to a small business, I just really, really learned to enjoy working with the team. I loved seeing the team thrive. I i was thriving more by being around them and seeing their ideas come to life, or getting the stuff that I didn’t like doing over to somebody else who absolutely loved it, and watching all of that positive energy come together. It’s just like this feels so, so good to have a team behind this. And I’m really glad that, you know, I was growing it into a business, instead of trying to stick, you know, 15 years later, doing freelance the entire time,
Troy Trewin 17:13
what has been the biggest mindset shift you in your small business growth journey?
Paige Wiese 17:18
I can do it. Keep pushing, you know, like you’re capable of it, don’t give up. There’s definitely been times along the way where I’ve had to ask myself, why am I still doing this? Is this what I’m should be doing? Or would it make more sense to go get a corporate job? And every single time I go through that and come back out of it, I’m so happy that I stayed in it, but it is a testament of you can do it. It’s it’s good to go through hard times.
Troy Trewin 17:42
The number one habit you think a small business owner needs to develop and maintain prioritizing.
Paige Wiese 17:48
I think prioritizing is one of the most important things I see, just even when we’ve had, you know, employees in different pieces, if you can’t figure out which one’s more important, if you can’t figure out where to spend the time first and then move into the next thing. And sometimes it’s small tasks first, then big, sometimes it’s big then small. But just what’s the prioritizing that you’re doing is really the key. I think our clients really like seeing that too. We don’t run in a ticketing system. We run in a priority and not necessarily. This one pays us more and this one pays us less. But what does the impact have on that client in this moment? If that website is down, that’s obviously a much bigger priority than Can I add this new blog page to our website? Right? If a marketing effort is down and a credit card failed, we want to get those things addressed pretty quickly, so we’re going to look at every single inquiry that comes through our door, and prioritize it that way, understanding where the client’s at. And I think way too many companies agencies just kind of go to a ticketing model, or just we’ll get to when we get to it. And so the prioritizing has also led to our success.
Troy Trewin 18:57
Yeah, if everything’s a priority, nothing is.
Paige Wiese 19:00
If everything is a fire is going to get done either, right? I mean, it’s really, Hey, you’re the one that took two months to get this information to us. It’s not going to be our immediate within four hour turnaround, you know, timeframe like, it’s just not urgent to that point. But clients think it can be at times. So being able to keep that internally really buttoned up of no no that can wait, this is what needs to come first.
Troy Trewin 19:31
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Paige Wiese 20:06
hire slow, fire fast. I know everyone has heard that one over and over. It’s still going to be one of the hardest things you can do, but I definitely know that there’s been times where we should have fired a little bit faster, you know. But there’s a lot of factors that go into that, whether it’s the team morale, whether that’s, hey, we need somebody right now, and that’s the only way we’re gonna go. But I think by making that mistake, it has led to a slower growth, you know, turnaround at times, or, yeah, a crappier team culture at times than I want to keep. And so I think that would be, you know, one of the biggest ones, or strategically grow, we are purposefully on more of a contractor mindset right now, because it does allow us that cash flow during the ups and downs. And I don’t think enough people talk about that. That’s how I grew from usually a contractor into full time employee when we were hiring people so that we knew, hey, can we get them to 40 hours? Great. Now let’s bring them on full time. And that just allowed, as a growing company that, you know, payroll, the cash flow to stay a little more ebb and flow. If we’re not heavy in marketing, we’re not putting out a ton of money in payroll. But if we are great, then let’s bring on that team. So I definitely think there’s some strategy around that approach too. What are
Troy Trewin 21:24
some of the things you recommend to building a sustainable and kick ass cultured out with the growth
Paige Wiese 21:28
transparency, I think is one of the biggest things. I am such an open book with my team. I make sure, like, Hey, you tell me what’s going on too. Like, we’ll figure it out, but I can’t have you hiding that we made a mistake someplace, or that we missed a deadline, or whatever that looks like, and so really maintaining more of that, like calmness and teamwork of Okay, now let’s go fix it, like what’s now that we know. How do we go address it? I’ve probably been through it, so, you know, don’t try to go through it alone as an employee. Don’t stay up at night stressing about, oh my gosh, I made this huge mistake. What are we going to do? Just come to me immediately. Client’s not happy about something. Let’s talk about it, because maybe it’s just a bad day for them. Maybe we screwed up. But when we can start to have those conversations and or even our growth goals, what are we trying to do? I’ve got Exit Planning stuff on my calendar every single day that could be stressful for a team to see exiting, but that’s not why we’re doing it. We’re doing it because that’s our ideal client in situations, right? So making sure that the team is fully aware of what is our gross plan, so that when those things start to come up, they’re not worried about their job in any capacity, and they understand why that stuff’s on. So I think the more that you can be transparent, it’s definitely led us to more success.
Troy Trewin 22:48
Tell our audience how you’ve handled balance. I don’t know
Paige Wiese 22:50
if I still have that handled you know, I do time blocking. I do make sure that we, you know, I’ve, I think it took a little while for me to figure out what is it that I want to be doing outside of work? I have always said that business is also a hobby, and so finding that separation between when do I go from assisting clients to working on the business is sometimes a blurred line. For a lot of people, they think I’m working a ton of hours and really like the moment I get to put my like work stuff away and actually focus on the business. I am so happy, so you know, but still making sure I find time to work out, to do the trail running, to do certain things that I know will allow me to kind of clear my mind and get out of work
Troy Trewin 23:35
mode. How much professional development have you invested in yourself?
Paige Wiese 23:40
Oh my gosh. So much as a self taught person, it’s it’s all been professional development over the whole 16 years I’ve done I found a little trick when I got started that there’s a lot of workshops in town, very poorly attended, often, and it’s great because it gives you the opportunity to talk directly with the expert and have your questions answered and how it reflects your business, instead of going to a college where there’s all sorts of things and they’re just teaching you the textbook, if you will. So I really took advantage of those resources when I got started, and then invested in a business coach for the better part of seven years of my business to really help me get to that next level, to really help me work through these hurdles, to remove my own emotions and put someone else in there that has a calmer mind in it, because it’s your baby, like you want to do everything so right? But when you’re so caught up in it all, it’s really hard to think logically. And so I think you know, that was another really key piece. And then beyond that, just hours and hours of, you know, whether it be webinars, whether it be audio books, whether it be, you know, just Googling and YouTube videos, whatever that looks like. Just, there’s been tons of professional
Troy Trewin 24:56
development. You’ve mentioned you had a coach. Have you had mentors along? Way I
Paige Wiese 25:00
wouldn’t be where I’m at without coaches and mentors. I think that any small business should definitely look at putting that in. It’s not about whether or not you’re good at what you do, or this or that. I purposefully grew the business. One, like we talked about, without any investment, but two, where I sat in every single role. I’ve done the graphic design. I’ve done the HR, I’ve done the accounting, I’ve done, you name it, everything, the taxes and so but I’ve also had to have mentors that are like, helping guide me. Of like, this is what you need to be looking at, though, this is what you should be doing. This is what that looks like. So, you know, being able to rely on them, it gives me a much stronger business base, and at the same time the people that go to and I’m just like, I’ve never done this before. Have you, like, what are your ideas? Or let’s think about this from a different angle. This is what I’m seeing. But there’s probably a better way that we could go about it. So definitely it had both and highly recommend doing both. Do you
Troy Trewin 25:56
have a board of directors or advisors?
Paige Wiese 26:00
No, not yet. We haven’t moved into that stuff yet. We’re on
Troy Trewin 26:04
page one of our final five questions, what do you think’s the hardest thing in growing a small business,
Paige Wiese 26:08
just the confidence and the just resilience to stick with it and just keep going? It’s gonna be ups and downs for sure. So, you know, be ready for them.
Troy Trewin 26:18
Favorite business book which has helped you the most,
Paige Wiese 26:21
I think one of them would be do less. I think just really understanding there’s ways to get stuff off of your plate. You don’t have to say yes to everything. And how do you make sure that you’re focused on kind of where you need to be focused,
Troy Trewin 26:32
any great podcasts or online learning tools you use for your own professional development?
Paige Wiese 26:37
Just, kind of, honestly, just plugging away. I listen to a lot of podcasts, but I’m still trying to, like, get in the groove of which ones are the ones I really, really enjoy. For me, it’s, you know, picking up a business book and trying to catch one little piece out of it, even, or, you know, just trying to better understand, I would say, honestly, be going back to the mentors though I’ve done so much networking and just talking with people that I’ve really been able to better understand by just having genuine conversations with
Troy Trewin 27:03
people. One tool you’d recommend to help grow a small
Paige Wiese 27:07
business, I would say, a CRM. We use Insightly. I know there’s tons out there, but I think if you are looking to grow any business whatsoever, some sort of CRM is an absolute must. I don’t know how people operate a business without one final
Troy Trewin 27:20
my favorite question, what would you tell yourself on day one of starting out,
Paige Wiese 27:24
you can do it. It’s going to come with some challenges, but you got this.
Troy Trewin 27:28
Thanks so much for the chat today. Paige really enjoyed it. In 2009 just after the GFC, with not enough work in architecture, you decided to start your own digital marketing business, doubling in size after covid. Dropped a little soon after that, but consistent, 10 to 12% annual growth over most of those 16 years. Started on your own now with a team of 16 full time equivalents. Congratulations on the growth. That’s fantastic.
Paige Wiese 27:50
Thank you so much. Yeah, definitely something I’m proud
Troy Trewin 27:53
of. That’s it. Thanks for listening. Please leave a review in iTunes or whatever platform you listen to us on. It means more small business owners will find our cast and help people with their business growth journey. You.