What No One Tells You About Hiring Freelancers

Like many founders who haven’t fully experienced the pain of hiring, I went on a freelance marketplace to get my first website (I went on Upwork, but Fiverr and other platforms are similar).

I had a good idea of what I wanted for my website, I expected to get some branding and a home page.

However, I didn’t recognize 3 things about myself:

1. My standards and expectations were high (while I thought they were just average).
2. My understanding of who I actually needed to hire was low.
3. My deadlines were tight, and my willingness to pay for the result was relatively low.

Back then, I felt very confident with my choice.

However, looking back, it was obvious that I was about to fail.

I thought my project was a quick win. I thought it would take less than a month, and I’d spend less than $15,000 for everything.

With the knowledge I have now, it’s definitely possible.
With the knowledge I had back then, it was not.

It took me 2 painful years, 5 website iterations, over $60,000, and a lot of pain along the way to get to the current result.

Do I regret what happened?
Yes and no.

Yes, because looking back, it’s obvious to see how naive I was. I also feel like I wasted a lot of time and money.
No, because we don’t know what we don’t know.

The problem is that I ended up learning this the hard way…

What did I learn in between?

I’m extremely grateful to anyone who reads my articles, so I want to save you from this painful journey.

The 3 Hardest Lessons That Changed Everything

Here are 3 big lessons I want to share with you.

1. ”If you aren’t willing to hire someone for 10 years, don’t even think about hiring them for 10 minutes”. It hurts me seeing startups spending 2 months to hire in-house but not willing to spend 2 days to hire a freelancer because I know what they’re about to live.
2. The second lesson helped me recognize that wanting a “designer” or a “marketer” is not specific enough. Design and marketing are broad fields, with many specialties. So I learned to pick the right person to do the right task because the penalties of doing otherwise are huge.
3. The third lesson is the most expensive since it showed up slowly over time, and it took me 2 years to realize this one: “If you think it’s expensive to hire a professional to do the job, wait until you hire an amateur”.

Once I deeply understood these lessons, I was able to build great websites within 1 month.

Let me say this again: it took me 2 years to understand what I can now do in 1 month.

Not only that, but I also build great brands, great apps, great marketing materials, great marketing execution, and so much more.

The power of hiring right is incredible.

Today, I’m very happy to hear: “It’s obvious you know what you’re doing. I want a similar website for my company”. Because it tells me that the Team&Tonic brand is doing its job. It’s clear, appealing, memorable, and trustworthy. It will attract a great community, and I get to work with great startups.

Even better, when clients book a call and start the conversation by telling me what Team&Tonic is about. They literally pitch me Team&Tonic (my own company!!). This means that I don’t need to pitch (which is great because it’s not the part I enjoy the most). But more than that, I can just focus on having a great conversation, understanding their needs, and building an amazing relationship.

This is all I wished for back when I got started.

The problem is that back then, I expected this to take one month.

Instead of 2 long years…

So let’s dive into these lessons that I painfully acquired but that changed my life.

Lesson #1: It’s Either “Hell Yes” or “No Thanks”

For those who know me, I’m a huge fan of Warren Buffett.

One of his most powerful pieces of advice is:

“If you aren’t willing to own a stock for 10 years, don’t even think about owning it for 10 minutes.”

That philosophy completely changed how I think about hiring.

And I translated it to:

If you aren’t willing to hire someone for 10 years, don’t even think about hiring them for 10 minutes.

It sounds extreme, but it’s the only mindset that’s ever saved me from the pain of bad hires.

Every person you work with leaves a fingerprint on your company

Every hire you make either elevates your brand or dilutes it, moves things forward or slows them down, builds momentum or creates endless work.
And yet… most startups spend 2 months interviewing for in-house hires, running reference checks, and aligning values.
But only 2 hours hiring freelancers (just because “they’re available”).

That’s how I started too.

I believed freelancers were short-term solutions. I thought I was saving time and money.

What I didn’t realize is that those quick decisions cost me years of progress and a bigger budget than what I could afford.

Freelancers aren’t a shortcut. Depending on how much effort you put into hiring them, they’ll either be an asset or a liability.

Which is why avoid any generalist freelancing platform like Upwork or Fiverr at all costs!!

Because if you pick the wrong freelancer, you spend your time managing, fixing, and second-guessing.

Those platforms bring a lot of volume but nothing to help you make the right choice…

Now I don’t hire anyone (freelancer or in-house) unless I feel I can work with them for the next 10 years.

The Mindset Shift That Changed How I Hire Forever

Hiring is not about filling a role. It’s about choosing my company’s future.

Now, I live by this rule:

If it’s not a “hell yes,” it’s a “no thanks.”

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Because anything less than “hell yes” always turns into regrets, delays, and rework.

And if you’ve ever felt stuck re-explaining your vision… fixing sloppy work… or paying for results you can’t use, you already know how costly a “maybe” hire can be.

This mindset shift changed everything for me. Now, when I work with a designer, marketer, or developer, it’s because I know they’re exactly right for the job.
Not just skilled, but committed, aligned, and exceptional.

And when startups come to me today and say:
“I knew you were the one.”
“This is the only agency I’ve seen that actually gets it.”

It’s because we built Team&Tonic on this same principle: clarity and quality, no compromise.

That’s why we only match startups with people we’d personally bet on for the long run. People I’d hang out with on weekends. Because I know what it takes to build something great. And we shouldn’t settle for less.

But learning this first lesson wasn’t enough. Soon, I had to learn another painful one…

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Lesson #2: Your Business Is Only as Good as Your Hiring

I used to think hiring a “designer” or a “marketer” was enough.

As if those labels were clear job titles with universal skill sets.

But I quickly realized that’s like saying “I need a doctor” without knowing whether it’s a heart surgeon, dermatologist, or pediatrician.

I may get the nicest person, but not the one who can solve your problem.

Design and marketing are massive domains, filled with specialists.

In design, you have brand designers, product designers, UI/UX experts, illustrators, motion designers, and more.
In marketing, you’ve got performance marketers, brand strategists, content writers, SEO experts, CRO specialists, growth hackers, and demand gen leads.
Each role solves a different problem. Each requires different thinking. And if you hire the wrong one (even if they’re talented), it leads to misalignment, frustration, and wasted money.

After learning the first lesson, I learned this second one the hard way too.

I hired people who were smart, creative, and even enthusiastic. But I was completely wrong about the problem I was trying to solve.

The result? I had to redo projects. I paid for work I couldn’t really use.
And I wasted months trying to “make it work” when it was never going to.

That’s when I came across this quote by Sony’s co-founder, Akio Morita:

“When I find an employee who turns out to be wrong for the job, I feel it’s my fault because I made the decision to hire him.”

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That quote hit me like a brick. Because it was true. It wasn’t the freelancer’s fault. It was mine.

I didn’t take the time to understand what I really needed. I didn’t vet for fit. I didn’t respect the complexity of the task.

Hiring the wrong person is the fastest way to silently destroy your business.

They don’t always cause drama. They seem to be doing the job right but they just quietly slow things down, drain your energy, and prevent great work from happening.

Now, I only hire specialists. And I only hire people with a track record of solving that specific problem for the specific stage of my company.

That mindset changed everything.

And it’s the reason Team&Tonic exists. To help startups hire the right person for the right task and work for as little as 5 hours.
Because when the right person is working on the right task, it doesn’t take them long to deliver a great result.

After experiencing bad quality hires, wrong hires, I had gone through cheap hires… This lesson was long, slow, and difficult to realize.

Lesson #3: The Cost of Cheap Is Hidden Until It Hurts

This is the most expensive lesson I learned. But it didn’t show up as a big invoice at first.
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It showed up slowly. In wasted time, missed deadlines, mediocre results, and constant stress.
And the invoice ended up being HUGE after 2 years.

I always had tight timelines and wanted to limit my budget.
Which can be fine, if I hadn’t been clueless about all of these lessons from the start.

Like many early-stage founders, I thought I was being smart by finding someone “good enough” for less. I believed I could cut corners without consequences.

But every shortcut came with a hidden cost:
The deliverables weren’t usable. The communication was broken. The revisions were endless. And by the time I realized what was happening, I had already burned through months, budget, and motivation.

That’s when I learned a painful truth:‍

“If you think it’s expensive to hire a professional, wait until you hire an amateur.”

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Since then, I’ve flipped the script. I now interview as many people as it takes to find the right one.

And I do what Jeff Bezos says:

“I’d rather interview 50 people and not hire anyone than hire the wrong person.”

Hiring the wrong person doesn’t just hurt your wallet.

It kills momentum, drains morale, and sets your startup back months.

Conclusion: Hiring Isn’t Just a Task. It’s a Growth Decision

If there’s one thing I hope you take away from this, it’s this:
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‍Every person you bring into your company either compounds your progress or drains it. So if you aren’t willing to hire someone for 10 years, don’t even think about hiring them for 10 minutes.

I spent 2 years learning what I now do in 1 month. I burned through time, money, and energy because I misunderstood what hiring really meant.
I thought I was saving money.
But I ended up paying for the same mistakes, over and over again.

I thought I was being efficient.
But I ended up delaying my company’s growth.

I thought I needed a freelancer.
But I actually needed a partner in execution.

Hiring is the most leveraged decision we make as a founder. It’s not about filling seats. It’s about shaping our company’s future.

So if you’re building something great, don’t settle. Don’t pick the cheapest. Don’t pick the most “available”. Pick the RIGHT person for each task.

A “hell yes” hire can unlock everything you’re trying to build.

Now, if you don’t know where to start, that’s exactly why I built Team&Tonic. To help founders like you avoid the mistakes I made and instantly work with the top 0.8% of freelance designers and marketers.

The painful road doesn’t need to be yours. You just have to choose better. And start now.

The Team&Tonic network was carefully built over the years by doing everything I’ve shared above. Finding A-players takes time, rigor, and systems. We’ve done the hard work, so founders don’t have to spend months (or years) getting the right people on board.

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If you’re feeling stretched thin, doubting your design or marketing hires, or your startup’s needs have just suddenly ramped up, now’s the time to upgrade.

You’ll get matched with a great freelancer who is committed to your success.
You can start on a flexible freelancing agreement, and bring them in-house once you've loved working with them.

There’s no excuse for not working with the best of the best.

Now, what if you don’t have clarity on what strategy is the best for your startup?

I recently created Startup Mentor Matching at Team&Tonic that gives you direct access to incredible startup CMOs and Creative Directors for just $50/month (only during beta!).

They’ll audit your actions, bring clarity, and help you design a growth system that actually works.

That price is a total steal to get access to incredibly talented people who have helped startups day in, day out.

So there’s no excuse not to get clarity on your brand.