[Q&A] Best Tools to Grow from Freelancer to Agency?

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On your journey from freelancer to agency-owner, your business tools and software inevitably need to evolve too. But with so many options out there, how do you choose? And when is it time to graduate from makeshift systems?

This was the dilemma facing Caesar from Data Nicely, who wrote into our show asking:

“As I move into being a founder, what types of tools do you recommend to grow our business?”

In this episode, we explore the common pitfall of over-complicating your tech stack, and how to keep things simple as your business expands.

Key Takeaways from this Episode:


  • Don’t choose tools before you have a process. The first step is to whiteboard your ideal process, regardless of the tools you use. This will help you identify the specific features and functionality you need in a tool.
  • Choose tools that are simple and easy to use. The more complex a tool is, the more time you’ll spend learning and using it. This can take away from your time actually growing your business.
  • Don’t switch tools just because you’re bored. If a tool is working for you, there’s no need to switch. Only switch if you find a tool that can significantly improve your process.

Picking the right tools for growth…

Our question this episode comes from Caesar, founder of a company called Data Nicely. They currently rely on a simple stack of Gmail, Google Docs and Sheets to manage their business operations and sales processes.

But as Data Nicely begins maturing from early startup to scaleup phase, Caesar knows their makeshift tools need an upgrade:

“As I move into being a founder, what types of tools do you recommend to grow our business?”

Specifically, Caesar explains they do a lot of cold outreach and need help tracking emails, managing outreach campaigns, and other sales automation workflows.

The problem? With so many options out there now, the decision feels overwhelming. Caesar finds himself paralyzed on how to choose the “right” tools to set them up for growth and prevent churn down the road.

It’s a common scenario many entrepreneurs face. You know you’ve outgrown your original systems, but struggle to identify and implement the next evolution. So where do you start?

We (Clay and Preston) share the strategy that’s helped us make smart SaaS decisions to streamline (not complicate) operations.

Map Your Processes First

Our first piece of advice? Don’t even think about software yet.

Instead, ignore tools completely and map out your sales and customer workflows on paper. Visualize what your ideal processes look like to take prospects from lead all the way to loyal client.

What are the key stages and steps involved? What does your communications cadence look like? How is data captured and leveraged across teams?

Get clear on what you need to happen, regardless of what tools can make it happen. Sketch it all out on a whiteboard or paper.

Once you have an aspirational view of your perfect processes, then you can start looking at tools to support that system, not the other way around.

Let your ideal workflows dictate which software you choose to facilitate them – not the other way around. Don’t distort helpful processes just to accommodate limitations in a specific tool.

I see many entrepreneurs fall into this trap with popular new tools like High Level. They adopt it as a silver bullet before mapping out their model for lead gen to client success. Then they struggle to wedge their disjointed processes into software designed for a more integrated approach.

So resist the urge to be swayed by hype. Map it, then find the tools to match.

Embrace the 80/20 Rule

When assessing your software needs, I like to think in terms of the 80/20 rule.

Identify the 20% of features that will solve 80% of your problems. Ignore the rest.

Most modern SaaS products are stuffed with hundreds of features across the board. Don’t feel compelled to use them all.

Preston shared how his former employer insisted on fully utilizing a complex project management tool called Jira. But it was overkill, requiring tedious data inputs for basic tasks. He spent more time managing Jira than doing actual work.

So be selective. Identify the critical features that will make the biggest difference, and ignore any fluff beyond that. Resist the temptation to utilize every bell and whistle just because you’re paying for the tool already. More features ≠ More value.

Stick With What Works

We both confessed our tendency to get bored and want to switch software just for something new and shiny. But we caution against it.

If your current system is working decently well, don’t jump ship purely out of novelty. Migration is painful. New tools take time to learn. You’ll deal with unexpected limitations and bugs.

Preston shared the example of switching his email provider just to access one new feature he thought he needed. But the switch made his day-to-day use way more complicated. A year later he migrated back.

So before abandoning your current setup, scrutinize whether the juice is really worth the squeeze. Will the new tool truly be better or just different? Incremental upgrades are rarely revolutionary.

Watch Out for “Shiny Object Syndrome”

In the entrepreneurial space, new software tools and apps emerge constantly. It becomes tempting to adopt every hot new offering for the sake of keeping up. But resist this “shiny object syndrome.”

What works well for one business may create unnecessary complexity for yours. Avoid adopting new platforms just because “everyone’s doing it.” Instead, keep asking how it fits into your unique processes and needs.

Evaluate each tool critically on its merits for your specific use case. Just because a big name recommends it doesn’t mean you should follow blindly.

Simplify Wherever Possible

As a general philosophy, Preston and I agreed: seek simplicity.

Choose straightforward tools that streamline your workflows rather than complicate them. They should fade into the background and get out of your way, not become just another thing to manage.

Style and interface matter too. Look for software with intuitive, minimalist design over cluttered, overly-engineered products.

Migrating from complex legacy systems to simpler cloud-based platforms has been an ongoing process for us. It’s reduced friction and freed up mental bandwidth to focus on business growth.

So Our Advice to Caesar?

We acknowledged Caesar didn’t get a tidy Top 5 list of tools from us. But hopefully he now has a strategic framework for making smart software decisions as Data Nicely scales up.

Here’s to picking technology that simplifies, not complicates your path from freelancer to founder!

Episode Transcript

This transcript was auto-generated and may have grammatical errors.

00:00.00

Preston Lee

Hello there and welcome to a special Q&A episode of Freelance to Founder. My name is Preston Lee with Millo.co and joining me on the air as always is my friend Clay Moseley from GetDripify.com. Hey Clay, enjoying the new offices?

00:12.97

Clay

What’s up man? Yeah, now that I’m moved – moving is the worst.

00:19.29

Preston Lee

Yeah, that’s no fun until that’s all finished. But new location – Austin, Texas still – but just found a new office to work in. You cool? You posted? Yeah yeah, you’ve always loved that city as long as you’ve been there.

00:28.74

Clay

Yeah, we’re downtown Austin now which is cool. Love the energy here, yeah it is, yeah cool, weird vibe.

00:37.21

Preston Lee

Just a, just a cool vibe.

00:43.11

Preston Lee

Ah, well good man. We’re gonna tackle this short question here today from – I’m pulling it up here – we go, ah, from Caesar, or Saad, how you want to say it. We’ll call him Caesar. He says “Hey guys, this is Caesar from Data Nicely, his company. My question is: as I move into being a founder, what types of tools do you recommend to grow our business?”

So, um, let me give a little more context. He says Caesar says they like to do cold outreach. Ah, there’s some different tools that help them find email addresses, or track if an email is opened, or manage build campaigns. He says there’s just lots of options out there and then he says it can be overwhelming as a founder as we mature away from doing everything in Gmail, Google Docs and spreadsheets.

What are the top 5 tools you recommend we get in place to set ourselves up for long-term success? So the real question is best tools as their company grows.

01:47.17

Clay

Huh, I mean, this is a pretty loaded question. You know, I mean, there’s… Okay, here’s my philosophy on tools.

01:49.20

Preston Lee

Why do you say that?

02:00.12

Clay

I think – and I’ll just say this because the question was asked and I get asked this question a lot – “Hey, what’s your favorite software for whatever?”

Um, I think first and foremost, I think what someone, what every business needs to do, is to completely whiteboard their process –

02:05.90

Preston Lee

Hello.

02:17.88

Clay

– for their sales pipeline from prospect to new client to raving fan. What does that look like regardless of software? Like completely ignore software. And then what you do is

02:32.70

Preston Lee

Yep.

02:36.61

Clay

What you do is, when you whiteboard it out, you whiteboard it out in a way where you think is perfect – in a perfect world, how does that process look? Everything from sales calls to onboarding to, you know, project management to, you know, whatever, right?

Um, and it’s in a perfect world. What does that look like? And then what you do is you go out and look for the tools that will fit that. So like I can sit here and like name so many different tools but I have no freaking clue if that’s going to fit

03:05.10

Preston Lee

Mm, yeah.

03:13.97

Clay

this person’s process.

03:15.75

Preston Lee

Yeah, I had the same thought when I read the question. I was like, well, you know, there’s some basic tools like for cold outreach I could say like Reply.io – I love them, they’ve added so many cool features. You know, there’s like for finding emails there’s Hunter, or, and there’s just like so many.

But I agree – like, I think, first of all, recommending tools is tough because the reason there are so many different tools – aside from capitalism of course – is because people have so many different preferences. Like, we work with

03:34.20

Clay

Ah, her.

03:44.52

Clay

The

03:47.89

Preston Lee

hundreds and thousands of freelancers all the time and someone might be diehard about FreshBooks, and another person completely hates FreshBooks, and they literally are freelancers who do similar work, right? And it’s, it’s just like such a personal preference.

So I’m with you – I sort of hesitate to say “Here are the best tools”

03:52.47

Clay

Um, yeah.

04:06.96

Preston Lee

to use. For me, it’s about like what tools I think – I’ve swung both ways. I’ve gone all in on tools and thought that was going to be the most important piece of my business. And then I’ve gone super simple and I think I prefer the latter.

04:15.35

Clay

Um, yep.

04:23.30

Preston Lee

For me, it’s like what tools get out of my way the fastest – they help me get the job done but then they get out of my way so I can do the real work. Because I think way too often, we end up – instead of having tools that help us with our processes we have tools that then we have to build processes just to manage our tools and it just becomes this whole thing.

04:39.42

Clay

Yes, it’s backwards! I see it all the time with, for example, High Level, or Go High Level as people like to refer to it to – are you familiar? It’s a, it’s a super popular –

04:42.84

Preston Lee

Yeah, it’s totally backwards.

04:50.26

Preston Lee

I haven’t heard of that. What is that? No.

04:56.38

Clay

Marketing all-in-one marketing software. Um, it does emails, it does SMS text messaging, it does – it’s a CRM, has a pipeline – anyway, it’s, it has like everything.

Um, it is what I use and so, um, you know,

05:01.98

Preston Lee

Oh yeah, okay. I’m yeah I’m looking it up right now while we talk. Okay, cool.

05:15.48

Clay

I hate the interface. I hate it. Um, the only reason I’m still using it is because once you learn it – because the learning curve is so high on this – but once you learn it, it’s super powerful. It’s like the most powerful marketing automation tool that I’ve worked with. But

05:18.67

Preston Lee

Ah, yeah.

05:24.95

Preston Lee

Yeah.

05:34.82

Clay

Um, but anyway, to your point, this is, this right now is a shiny object to at least the circles that I’m in and people are signing up for High Level because they think it’s going to solve all their marketing problems. I’m like, no, it’s a tool!

And so what they do is they go sign up for this thing, which by the way, the people at High Level, they built this for agencies – not the end user. Not the chiropractor. Not the HVAC service, but I’m seeing a whole bunch of these end users, these small business owners, signing up for it.

06:03.46

Preston Lee

Ah, got it. Okay, yeah, yeah, yeah.

06:10.45

Clay

And then they’re like “I don’t get it, I don’t understand how to use it.” Well it wasn’t meant for you, but they’re buying this thing and then they’re altering their processes and their systems to fit this software. And I’m like, going back to my original point: Like, go whiteboard your shit out and then find something that fits. But they’re like –

06:12.38

Preston Lee

Yeah.

06:29.30

Clay

They’re trying to jump on the bandwagon because everybody’s signing up for this thing.

06:30.78

Preston Lee

Yeah, yeah. I experienced this when I worked at, ah, so I moved from like more of a traditional old school corporate setting, a company that had been around probably over 100 years – I don’t actually know but a long time – and then I, I got hired. I left that job and I got hired at a tech startup that was just a few years old, really high tech guys I was working with, all pretty young people, and it was, you know, traditional tech startup.

And we used – what’s that product by Atlassian? Atlassian –

06:50.57

Clay

The.

07:06.77

Preston Lee

Um, I don’t remember either. I’m going to look it up while we’re talking. Ah yeah I think maybe it was, yeah that sounds right. It’s sort of, it’s sort of like a really complex –

07:06.79

Clay

Ah I know you’re talking about. I don’t remember what it’s called now. Now we’re both googling it. Jira! J-I-R-A.

07:23.64

Clay

Yeah.

07:26.29

Preston Lee

Because I know Atlassian bought Trello, which is like a sort of drag and drop, really simple. But I think yeah I think Jira was it. And we, I’ve spent probably – I don’t know – a third of my day

07:26.94

Clay

Yeah, oh.

07:43.26

Preston Lee

managing my Jira cards, whatever I don’t even remember what they were called. It was just like so complicated. And management, like, would not let us, you know, not completely fill out a card. For that, like if I had to go use the restroom, I feel like I had to fill out a Jira card and like give them all the details. It was ridiculous. And I just –

07:48.20

Clay

Um, yeah.

08:02.13

Preston Lee

I pushed back so hard but they just held on to that and I was just like, “Guys, we are wasting so much time just managing the process instead of having a process that gets business done.” I hope, I hope you know they’ve maybe solved that problem since then but, again for me it’s like, simplify, simplify.

08:15.52

Clay

Um, yeah let’s, yep.

08:20.96

Preston Lee

Just because a tool wants you to add categories and tags and dates and deadlines, that doesn’t mean you have to. If that’s helpful, use it; if it’s not helpful, leave it alone. We used ClickUp for the longest time, ah, and I think we probably used like 20% of the features they offered because it’s just like, you don’t –

08:24.43

Clay

The.

08:36.50

Clay

Yeah I feel the same way. Like we, we’re switching to Notion for that. Notion’s like, simple. Yeah, yeah it’s very minimal.

08:38.70

Preston Lee

You don’t have to use it just because it’s there.

08:45.96

Preston Lee

Um, yeah, yeah they sort of pride themselves on being simple if I remember right.

08:54.32

Clay

Um, I think everything’s actually black and white for the most part. Um, but yeah I, I think, ah, you know, sorry Caesar, you’re probably not going to get satisfaction out of our answers but, like, two things: Whiteboard your process out and choose software that fits that. And then – but simplify, is what you said.

09:11.76

Preston Lee

Yeah, yes, just, just choose something simple and I think, I think our advice goes hand in hand right? Because it’s like, I’m just saying like pick something that gets the job done and you’re saying figure out what the job is to be done first and then pick something that accomplishes that. So.

09:24.00

Clay

Um, yeah. I want to make one more point, um, because I get caught in this little circle where I just get the itch to switch software, right? Yeah but like –

09:34.93

Preston Lee

Oh I was gonna say this same thing. Yeah go for it. Yeah.

09:40.76

Clay

And I’ll do this for stuff where I’m like, my current software is working. Why do I want to switch just because I get bored, right? And don’t, don’t follow that light. Ah, don’t fall into that trap because if something’s working –

09:46.58

Preston Lee

Um.

09:57.69

Clay

Just don’t even think about switching. It’s working. Ah.

09:59.85

Preston Lee

Yep, yep. Yeah, or even if, I would say, even if it’s working like 90% – I, okay, so here’s a really concrete example: I was on MailChimp for the longest time, like years, like maybe a decade on MailChimp, and this other software –

10:09.91

Clay

Yeah.

10:15.61

Preston Lee

Was it ActiveCampaign I think was the other software? They had this one feature that I really wanted to try. So I went through the terrible, awful process of migrating tens of thousands of email addresses and customer – ah, customer –

10:24.40

Clay

Oh god.

10:30.76

Preston Lee

All the customer data and whatever, all over to ActiveCampaign, importing it, setting it all up, resetting up all my campaigns. It’s all very manual. It took forever. It was a pain learning the new software because it was all different. And then I kind of used this new feature but I didn’t really take full advantage of it.

Meanwhile all the other, like, basic stuff that I had to do on a regular basis, like sending just a typical email campaign or a follow-up or like sign-up forms – they were all way more complicated. MailChimp made them super simple; ActiveCampaign overcomplicated them. And so, meanwhile I’m miserable –

10:59.82

Clay

Assisted.

11:06.19

Preston Lee

And then a year later I just switched back to MailChimp because I just – I mean part of it is what you get used to, right? So take that with a grain of salt if you’re deciding between those two pieces of software, but. I just, it wasn’t worth it for that one feature, for that 10%, if it’s working eighty or ninety percent just like make do

11:10.94

Clay

Um, yep.

11:22.67

Clay

Um, yep.

11:25.48

Preston Lee

with what you’ve got and stick with it. And stick with it for a while. I feel like people tend to switch, like, every time, you know, Pat Flynn says there’s a new software that will make you rich or whatever, people will switch over to it. And it’s just like, look, you know –

11:42.13

Clay

Ah.

11:42.55

Preston Lee

it’s not that different and not that much better. And particularly if it’s new, it’s not going to be better than this thing that you’ve been using for 10 years. It’s going to lack a lot of features. So yeah, yeah, yeah. So.

11:47.98

Clay

Yeah it’ll have bugs too that’ll have bugs.

11:56.26

Preston Lee

Anyway, lot. Ah, clearly we have – or at least I personally have – some soapboxes on that particular topic. But Caesar, we hope that was helpful, man. Ah, the real truth of the matter is we can’t give you a list of top 5 tools you should be using. Um, but that’s some, those are a few things to consider while you’re choosing tools to help

11:59.23

Clay

Assist with the.

12:15.58

Preston Lee

grow your business. And we hope that was helpful, man. Best of luck to you as you grow your business. If you want your question answered like Caesar – or not answered like we did for Caesar today you can visit freelance to founder.com/ask.

 

12:17.79

Clay

Um.

 

12:29.67

Preston Lee

And just fill out a quick form there and we’ll answer your question on the air send you the link to the podcast and you can listen in. Hopefully it’s helpful to you and Clay Mosley from gitripify.com thanks so much man, right? Take care.

 

12:40.60

Clay

All right see? ah.

 

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Written by Preston Lee

Editor at Millo.co

Preston Lee is the founder of Millo where he and his team have been helping freelancers thrive for over a decade. His advice has been featured by Entrepreneur, Inc, Forbes, Adobe, and many more.

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Reviewed & edited by Mateo Melgar, Editor at Millo.

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