How I Quit My Job and Started Freelancing Asia Matos

A few years ago, when I quit my job to start freelancing, I was fortunate enough to already have a few contracts lined up before putting in my 2 weeks notice at work.

But, that’s not the path everyone takes when launching a freelance business (or any business for that matter). And I’m a major proponent of sharing about people’s journeys that are different than mine.

Today’s guest post comes from a boss marketer I’ve had the pleasure of getting to know over the past couple of years…

Asia Matos of Demand Maven quit her day job completely cold turkey earlier this year (without any clients, major deals in the works or a huge savings account to pad herself for months without an income). Since then, she’s been building a solid freelance business for herself, where she partners with early-stage SaaS companies to help build their marketing engines and get them to their first 100 customers.

Here’s Asia…

Asia Matos How I Quit My Job and Started Freelancing

From here on out, I’m going to turn this over to Asia so she can share her story and break down everything she’s learned since quitting her jobs to start freelancing earlier this year.

Consider this post a free crash course in how to quickly bootstrap your way into freelancing full-time.

Now, over to you, Asia!


“If it terrifies you, that means you need to do it.”

I was dreading making the phone call.

When I say dreading, I mean I was pacing in my living room and rehearsing what I was going to say.

Sitting on the couch and gazing despondently out of the window.

Then I’d refresh my inbox over and over again — hoping, wishing that someone or something would release me from what I was about to do.

I started pulling up articles and researching things like “how to tell your recruiter you’re withdrawing from their pipeline” and “how to know if you should start your own business” — because those are the types of things you’re totally going to learn from an article.

(cue the massive eyeroll and groan) Whatever.. no regrets, right?

Deep down, I knew I just needed to do it.

I knew that if I didn’t, it wouldn’t be fair to my recruiter who was working hard to place me, and it also wouldn't be fair to myself.

It was a requirement for me to dedicate the mental space and energy to doing what seemed unthinkable: going cold-turkey, and starting my own marketing consulting company.

My own slice of the endless entrepreneurial pie.

And as my first manager used to say, “If it terrifies you, that means you need to do it”.

Telling my recruiter that I was withdrawing his pipeline in pursuit of a dream I had been talking about for years was only the first step — and it was the scariest step.

I wasn’t actually removing a safety net, but it sure did feel like it in the beginning.

What I wasn’t expecting was the response from him, and my entire network.

This is the story of going completely cold-turkey, launching DemandMaven, and making $10k in 90 days.

In this post, I'm going to cover how I:

  • Pre-seeded my first clients
  • Designed a launch that booked my next few deals
  • Learned from my almost-made-me-quit mistakes

I'm going to be *completely* transparent about what worked, what didn't, and what I'm working on next.

Over the edge

“Asia, I think that’s absolutely fantastic,” my recruiter said, emphatically and utterly genuine.

(I breathe a sigh of relief) Omg.. he understands! He doesn’t hate me!

If I could do it over again, I would have started my company years earlier. This is an amazing move for you!”

We then discussed his business, how he got into recruiting, and why he decided to start his company in the first place.

He then gave me the most important advice about the journey I was about to embark on:

Focus on invoicing.

Fast-forward 75 days, and my Stripe account said this:

Before I made the call, I actually already had two clients, and they were what pushed me over the edge to go completely cold-turkey.

No, I didn't have a giant network of clients waiting for me.

I didn't even have a side hustle before starting DemandMaven.

I haven't written for Forbes, Entrepreneur, or any of the top publications.

I'm not famous (yet 😉).

Just a SaaS marketer with a passion for helping founders. 💁‍♀️

I love working with startups, and I've had the opportunity of working with two great ones over the past 2 years: both of which have 10x'd year over year, both funded companies, both at different stages in the startup lifecycle, and both incredibly crucial to my own learnings and success.

But the entire time I was living and breathing startup life, I couldn't help but develop my own entrepreneurship. I had an itch to build something on my own.

Startup life also means high-risk / high-reward, so in many ways, I felt like I was being conditioned to live in chaos while also growing something. I was already drinking from the firehose.

Plus, deep down I knew that job security was a myth — especially in startup world.

Tomorrow isn't promised.

And then a thought hit me: could I find clients while I'm looking for my next gig?

In my case, I was faced with a decision: find a cushy in-house job, join another high-risk / high-reward in-house job, or go solo.

I chose Solo.

Finding DemandMaven

I'm going to keep it real with you: there's a lot of marketing consultants out there.

Ugh.. great.. another marketing consultant? It's what the world needs.

On the one hand, it makes me feel like I have a network of people who already get me.

And on the other, very unspecial.

I realized pretty quickly that differentiating myself and communicating my value would be important.

But I'm a SaaS marketer! I'm used to doing it all.

Content? Done.

Product marketing? Done.

Sales enablement? Super done.

CRO on demos or free trials? Done.

The list ran on for me, and as a multipotentialist (I don't like the term "generalist" 🤮) I knew it was going to be tough to decide.

So in true Simon Sinek fashion, I started with my "why".

My why:

To help startup founders get their companies off the ground leveraging marketing and growth as lean as possible.

And the only way I know how to do that is through demand generation: combining high-quality marketing activities that prospects actually want with powerful AF funnels.

In ten minutes, DemandMaven was born.

(Except now I needed to test it.)

Pre-seeding my first two clients

Alright. Now that you know the context and the backstory, I can talk about the good stuff.

The first step to nailing my first two clients during this brief job search period was to test the market and get as informed as possible.

As a marketer, I realize I have a more-than-slight advantage.

I know how to carve a market, tell stories, define value, build funnels, and create programs that convert people into either customers or advocates.

Still, I started out like most new freelancers or entrepreneurs do: reaching out to their network.

But I wanted to be more focused than that.

I could totally go Wreck It Ralph on my entire network and asking for work.

Or I could research the market first.

This is the playbook I decided on:

  • Reach out to other marketing consultants in my focus
  • Reach out to exact people who were my target market - in this case, technical founders of startups or consulting firms
  • See what kind of response I get after launching DemandMaven

I targeted the people who I knew were marketers and were offering marketing services first because I knew they'd be honest.

The types of marketing consultants I know run the gamut — some are SaaS marketers catering to the SaaS world, boutique agencies, freelance writers, dev shops… The list runs on.

After hand-picking a few people I really trusted and admired, I reached out and offered to buy them lunch in exchange for their insights on the current market.

The response was a resounding "yes", and two of them actually led into my first deal!

Turned into:

And that's exactly how I landed my first client — a company I'm still working with to this day because they're what I consider to be a "star child".

My second client was one of the people I interviewed during this research process.

(And to be honest, I went into the conversation with zero expectations.)

But he was getting his startup off the ground and managing a devops consulting firm at the same time.

He needed help, and when he heard my story about what I was building, he wanted in.

His company became my first $4k deal and second client.

Overall, the conversations I had were eye-opening, but at the same, gave me some very real things to think about:

  • Creating repeatable packages and marketing services
  • Building a tech stack as fast as possible
  • Building a referral engine as fast as possible

But like many great conversations, I got a few new leads to reach out to and one I hadn't quite thought of: venture capitalists in the Atlanta startup community.

I sent a cold LinkedIn message to one of the partners from Atlanta Ventures (they run a kickass community over at Atlanta Tech Village), and warmed it up as much as possible with some common history:

Within minutes, I got this response back:

After meeting with Atlanta Ventures, I was introduced to several more founders with very real marketing and growth problems.

The first meetings were crucial because they gave me the perspective I needed to pinpoint my first set of marketing services.

Things to keep in mind here:

  1. I was still in the process of officially creating the business - I used Stripe Atlas to incorporate DemandMaven in a matter of days, but I was still figuring out my stack and what tools I needed to run my business as efficiently as possible
  2. I wasn't 100% sure how my packages were going to perform over time, so I started out with a general marketing retainer.
  3. I had to create and adjust my contracts and agreements as fast as possible. Luckily, my consulting friends sent me tons of examples.
  4. I hadn't even "launched" yet. The only people who knew what I was up to were the people I told.

Launching DemandMaven

There's two pieces of advice I've heard over and over again about going solo:

  1. Don't go "cold-turkey".
  2. Don't tell everyone about what you're building - yet.

Ironically enough, I actually agree with both despite the fact I've broken both rules.

Going cold-turkey and immediately jumping into consulting or freelancing after full-time in-house life is a shocking and unpredictable transformation.

I've heard horror stories about people trying to start their own consulting practice after years of in-house life, realizing the grind it was going to require, and then giving up.

Typically these businesses fail because they:

  • Can't figure out how to make it profitable fast enough
  • Can't make their services as repeatable as possible
  • Mismanage margins for each client project
  • Can't fix cash flow problems
  • Don't charge enough for their services

Knowing this, the only way I felt I was going to be successful was if enough people were both aware and excited about what I was building.

I broke the first piece of advice — meaning I was going to have to rely on the second if I was going to "make it".

There's research about telling people about your goals before you've actually taken steps to manifest them.

According to a study done in 1933, “Announcing your plans to others satisfies your self-identity just enough that you're less motivated to do the hard work needed.”

“Once you've told people of your intentions, it gives you a ‘premature sense of completeness.’” the LifeHacker article continues.

PsychologyToday covered it as well: “They suggest that when people announce an intention to commit to an identity goal in public, that announcement may actually backfire.”

Despite knowing the harm of a public announcement, I planned a launch for DemandMaven anyways with the intent to make a big splash in my network (even though I probably shouldn't have).

These were the steps I took to plan my launch and create my sales funnel:

  • Step 1: Research other consultant's "launches" or announcements
  • Step 2: Study other consultant's websites
  • Step 3: Design and build my own launch

Let's dig in.

Step 1: Research other consultant's announcements

What makes for an intriguing launch for a consultant? I thought to myself.

I've planned and participated in Product Hunt launches, beta launches, and full-blown product launches.

But consulting?

I wasn't sure what this could look like.

I pop open a new tab and start researching the agencies and consultants I knew were killing it.

The launches I unearthed were diverse in scale, but they each followed a few key themes:

1. They all told an amazing story. Remember Pixar's rules of storytelling? The fourth rule is the one I'm thinking of in particular:

Once upon a time there was ___. Every day, ___. One day ___. Because of that, ___. Because of that, ___. Until finally ___.

Every launch had an announcement with a story that leveraged this format, but instead, it was incredibly personal, humbling, and in many cases, vulnerable.

The authors highlighted very personal, but relatable reasons why they were leaving their full-time gigs behind and why they were choosing the freelance life.

2. They all leveraged their reach. For every single launch I studied, there was some kind of "press". In one case, literal press coverage.

For the most part, they all created an announcement that was then distributed through their networks.

This was going to be crucial for me and launching DemandMaven. I had a large network, but reaching enough people to get the sales process going was going to be a challenge.

3. They all had powerful CTAs and follow-up steps for interested parties. If you go through all the trouble to plan and build a launch, you should tell people exactly what do next if they read the announcement and have a need.

And if they decide to check out your website, make sure to have a funnel ready to convert visitors.

Step 2: Study other consultant websites

Since you're here on RyRob.com, you're likely already familiar with the side-hustlers, consultants, freelancers, and founders he features on his blog and podcast.

I also found Brennan Dunn, Jane Portman, Mojca Mars, Joanna Wiebe, and Nichole Elizabeth DeMeré — all incredibly prolific entrepreneurs and consultants who have built impressive businesses.

Naturally, I studied all of their websites.

I studied how they described their services, wrote their long-form sales pages, and every step of their funnels.

I signed up for their newsletters and downloaded some of their free lead magnets to study the emails they sent me.

It might sound like a lot of effort, but I needed to stand on the shoulders of giants if I had a chance at succeeding.

I wasn't trying to build Rome.

I just needed my launch to get conversations started and a funnel that would generate revenue.

Step 3: Designing and Building My Launch

Finally, I get to apply everything I’ve researched.

Based off of what I found through research and my own goals, I decided to keep my launch list simple:

  • Set a launch date
  • Build a kickass website
    • Drive visitors towards taking a limited-time-only free marketing strategy call
  • Write an announcement
    • Drive people to the website
  • Leverage the LinkedIn platform to take advantage of reach
    • Publish as an article
  • Distribute through social
  • Point all of my profiles to the website
    • Everything from Quora to Twitter to Instagram to Angellist.co

The result?

Here's a deep-dive into some of the key decisions I made:

Build a kickass website.

After studying the greats, I had a few strategic decisions to make.

I could either build an entire marketing engine leading up to launch day (email courses, checklists, nurture campaigns from downloads, a few blog posts that convert prospects into those things, etc) or I could keep the engine as lean and simple as possible.

I chose the lean route. Here's why:

  1. I didn't know what kind of services my target audience actually wanted. Part of this is because I didn't have a long list of previous clients and lessons learned. I work with startup founders, and it was tough guessing what services they'd actually bite on.
  2. I wouldn't know how to optimize my funnel if I built the entire machine first. This might seem obvious, but I'm a huge believer in building your marketing and conversion engine as you go rather than trying to build it all at once. Trying to figure out why it fell apart later is not fun — the process is usually too overwhelming to tackle at one.

Your time is very limited.

The only times I've seen building the engine all at once work are when you, the marketer or entrepreneur, know your target audience so intimately that you already know what they're going to bite off on.

You also already know how long it's going to take to sell and close deals, so you can build an engine for that accordingly.

When you're just starting out, I recommend keeping it simple, and then layering on pieces that could help accelerate and automate your prospecting and selling process.

What do I mean by "marketing engine"?

I'm talking about all the content, sales emails, conversion funnels, and experiences you could implement to sell your services.

That said, when I built my website, I focused on the only objective I knew closed deals: booking meetings with qualified prospects.

Booking a marketing call was my number one CTA.

Leveraging the LinkedIn platform for my advantage

I feel so villainous even saying that.

You will do my bidding, LinkedIn!

It's true, though.

If there's one thing I know about LinkedIn, publishing an article will give you a lot more mileage than posting update — unless, of course, your LinkedIn audience is just so engaged, that the "likes" alone boost distribution.

If you've ever seen a LinkedIn post by Josh Fechter, you'll know exactly what I mean.

Might be a shock, but I haven't spent the greater part of a year hacking LinkedIn's distribution algorithms through statuses and copywriting.

My LinkedIn audience isn't that engaged with my status updates (3 - 4 likes max per updates), but LinkedIn would do the hard work of distributing an article if I published it through their site.

Which, if you think about it, makes total sense.

LinkedIn would love nothing more than for you to put your original content on their site.

Plus, my target market was already there.

It made a lot of sense for me to use the platform to get the most reach.

I also hadn't built up a Medium audience, so this was my best bet.

There was also another trap card I had stashed away in my back pocket: updating my job status.

If you want to trigger your network, update your title or “change jobs” in LinkedIn. People will come out of the woodwork.

As the #1 employee at DemandMaven, I owed it to myself to make it known I was venturing out.

Launching DemandMaven

After writing my announcement, I published it on LinkedIn on a Tuesday morning (probably the best day of the week to launch anything, honestly).

I then distributed the LinkedIn post through my personal Facebook page, a few Facebook communities, and Twitter.

The response was huge.

My calendar was packed the week after. Everything in orange is a discovery call. Everything in purple is more of a reconnect meeting (less sales, more networking).

And it stayed like this for several weeks.

You can see the traffic spike, too, in Google Analytics from when I launched.

And much to my satisfaction, I booked several of my first marketing calls — one of which became a client.

8 Lessons I've Learned Since Going Cold-Turkey

So what didn’t work during this process?

The learnings have been a-plenty since I started DemandMaven.

And in total transparency and vulnerability, I wasn't entirely sure I was cut out for it.

This could fall apart at any minute, but from what I've seen and heard from others, we all (mostly) start the same way.

These are some of the big lessons I've learned. I really hope they serve you in some way.

Lesson 1: Cling to your "why".

Remember my "why" from earlier in the post?

It keeps me going.

It keeps me centered, and grounded, and from feeling like I'm not going to be able to find success.

It also helps keep the imposter syndrome at bay — something I find even the most talented freelancers and entrepreneurs experience.

When we find purpose and meaning in our work, we can move mountains to get closer to fulfilling that purpose.

You'll hear stories over and over again about founders pursued their vision — seemingly over the most impossible of circumstances and despite all odds.

I encourage anyone reading this to stick to your purpose.

Stick to your "why".

It will carry you through the trough of despair.

Lesson 2: Fix your cash flow.

In the beginning, I didn't always feel like I could be picky about the projects I took on, so I’d pretty much take anything that would pay the bills.

Cash flow is one of the number one reasons why businesses fail.

You're operating at a loss when you first start out and it seems like you can't rise above the profitability line.

So what happens?

You take on ill-fitting projects out of desperation.

You're negotiated down to a lower rate because you're desperate.

You're suddenly behind on other obligations.

You end up not being able to pay yourself (or others).

And it just spirals from there.

Even I haven't quite mastered this, but to prevent myself from getting stuck in this cycle, I've become best friends with my accountants (of which I actually have two).

By understanding how cash flow works (and really just basic finance and accounting), I've made adjustments to how I both position my projects and how I charge for projects.

It's made a world of a difference, and enables me to stay in business.

Lesson 3: Sell your value, not your time.

This might not always be true for everyone's side hustles, but for marketing consultants, you can't sell your hours — at least, not for too long.

Time is the only thing that can't physically scale.

It's one of the few things in life that are truly limited.

That said, if you can avoid selling your hours, then do it.

Selling time is a trap, and unless you plan on expanding your business with employees or contractors, you won't be able to scale yourself.

And since time doesn't scale either, you'll undoubtedly be judged based on your hourly rate.

I've learned this the hard way several times over.

Granted, I was just starting out. And while I knew better, the imposter syndrome prevented me from pitching based on value.

Learn from my mistake as fast as you possibly can. And if you’re stuck in the cycle, take the steps towards value-based selling.

Being seen as a commodity is death.

Lesson 4: Find your tribe.

When you become a side hustler or business owner in any way, you inevitably attract other side hustlers and business owners.

I've built a solid network of SaaS marketers, founders, and consultants, and I'm not sure I'd still be doing this if I didn't have them.

They've become my tribe.

They keep me motivated — in both a friendly and competitive way, and through camaraderie.

It's unlikely that your friends will understand the highs and lows of founder life.

They might be able to deeply empathize, which is still valuable, but might not be able to offer any insights from personal experiences.

Your peers, however, absolutely will.

Reach out to them. Befriend them. Have them in your corner.

I actually compete with a lot of my network. We all have the same common understanding, though: the pie isn't finite.

And someone else's slice of the pie doesn't mean I don't get any.

Opportunities are boundless, and from what I’ve found, there’s plenty to go around.

My network provides referrals as well, so it’s a win-win.

I literally just got a message like that in my inbox this morning:

Lesson 5: Niche as much as you can.

This is something I'm still working on.

The nature of my industry demands that marketers be multipotentialists and have a number of very strong, but diverse capabilities.

SaaS marketers are some of the most sophisticated marketers out there.

We kind of have to be.

Try selling "sophistication", though, and you'll inevitably be hit with questions about your niche and your number one strength — i.e. Facebook Ads or CRO.

One of my peers offers *only* copywriting for email onboarding. (And she's really good.)

That said, I don't pitch myself as a pure anything-marketing-related retainer anymore for many reasons.

They weren't specific enough, I ended being a virtual CMO for too little in return, and it just doesn't scale very well unless it’s the only thing you do and you have two-max clients at a time.

Now, I offer just two packages:

  1. Traffic-building + Content Marketing Strategy & Creation
  2. Campaign Design and Implementation

I'm focused on SaaS businesses with at least a Seed round of funding. I do take on non-SaaS clients, though, if it's a no-brainer fit (leveraging some previous experience I have marketing something similar).

The harsh reality is that even this probably isn't focused or niche enough.

Give me 6 months and I'll let you know how it shakes out. 😉

Lesson 6: Going cold-turkey isn't for everyone.

I remember reading something from Ryan, actually, about the importance of building a side hustle and his own aversion to taking big financial risks (like going cold-turkey .. hehe).

I acknowledge and respect that 100%.

Building something on the side isn’t less impressive than what I'm doing.

If anything, it's the wiser, more grounded choice.

Doing what I did over the past 3 months isn't going to be for everyone.

It's been both terrifying and rewarding at the same time.

I'm pretty lucky to have a rock-solid support system. I don't think I'd be doing this without the support and wisdom of my fiancé Zac.

While this business is not lucrative yet (I'm definitely not swimming in money), I believe it will be one day — either through actual revenue or just the experience alone.

Sometimes, abundance doesn't mean money.

During one of my tougher weeks, I texted and called my CEO from my previous job. I was having problems with cash flow and closing higher quality deals, and I was pretty close to just giving up and taking a cushy in-house job.

I knew he'd have a keener insight.

He reframed my problem and reminded me of how far I’ve come:

Him: Asia, you need to think about this differently. How much does an MBA cost?

Me: .... Like $100K? More if it's from Emory.

Him: And how long does it take to complete a degree?

Me: .... Two years?

Him: And how much have you invested in starting this business?

Me: .. $1500 bucks. Of which I actually already reimbursed myself.

Him: So then think of this journey as your own personal MBA of which you've already made some ROI from your own initial investment. On top of that, you've learned more in 45 days than most people learn while pursuing their MBA. And what you'll gain out of this is a network more powerful than you could ever imagine, and a business sense you'll leverage for the rest of your life.

I bet you're an even better marketer too, now.

He couldn't have been more right.

Lesson 7: You’re the expert.

When you’re first starting out, you’re going to make mistakes. You’ll mess up. You’ll mis-pitch.
Undersell. Take on clients that you maybe you shouldn’t have.

And then you’ll circle back to other people who have been there, done that, and can offer some insight on how to avoid those mistakes and overcome them.

In a few cases, I took on deals where the client didn’t ultimately see me as the expert.

That might sound weird.

Why would they hire you if they didn’t see you as the expert?

I’ll tell you, my friend.

It’s the kiss of death: they want to hire you as a full-time employee.

Over the past 90 days, I’ve learned that when prospects secretly want to hire you as an FTE, the consultant-client relationship changes.

It's not a bad thing if they'd like to add you to the team. In fact, I consider it an honor.

But it definitely changes the dynamic — one that could lead to underselling on your value and compromising to keep them as a client and make it work (which is a very tough situation to be in).

It should be the other way around.

You’re the expert, after all.

When you pitch your projects, make sure you’re taking it from the approach of an expert.

It’s true that you’re always learning from clients and the projects you take on, but avoid being too casual about your expertise.

I’ve made the mistake about being too casual about what I’ve accomplished in my marketing career, and it’s cost me leverage.

Lesson 8: Get your imposter syndrome in check.

Or if you can just surgically remove it from your brain, even better!

It's important that we're humble.

But it's more important to have your own back, and to keep any negative self-talk out of your head.

It will affect the way you pitch yourself, the way you close deals, and the way you negotiate.

Your clients won't get your best work, which will impact any future case studies and results you can achieve for them.

I could talk forever about how to manage your imposter syndrome, but the gist is this: be aware of the stories you tell yourself.

Some of them could be preventing you from finding success. ❤

So what's next?

I've got this giant, chunky list of things I need to build and execute to grow the business.

I've finally started my own content marketing strategy and distribution - which, if you're into a good Website Teardown, I'll be pumping out a few every month.

I'm speaking and presenting as much as possible.

I'm also doing some high-quality outreach (sending 10 emails max with a custom video in each one) to book some meetings with qualified prospects.

I have plans to build out and automate the amount of teaching I do on every discovery call (since I end up educating just about every founder on how acquisition works). My goal is to have an email course (or something similar) out by the end of Q3, 2018.

But no matter how big the list of to-dos feels, I know that chipping away, piece-by-piece is still progress.

And thankfully, I've got the hustle-muscle to get there. 💪

Thanks so much for reading!


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