Freelance Family Man 90-Day Apprenticeship

In 90 days, you’ll build or repair the foundation of your service business, so you can provide for your family on your own terms.

This program is designed for busy dads who are either struggling to earn enough income as a freelancer or haven’t started yet but are ready to escape the 9-5 employee trap.

Find The Right Niche

Figure out what services you should be selling or refine your current services that best aligns with your strengths, passions and market demand.

Create Offers That Sell Themselves

Design the right packages and pricing with an offer so good, you’ll have prospects lining up.

Find Clients Consistently

Learn marketing and sales strategies that attract leads and clients consistently.

Contact Us To Enroll

WHO THIS IS FOR

  • You are not earning enough income in your business to support your family comfortably

  • You may only be freelancing part-time or not at all yet

  • You feel stuck between a job you don’t want and a business you don’t know how to launch or grow

  • You want to build a real business around your skills, not chase occasional gigs

  • You feel like you don’t have a solid system to attract clients consistently

  • You are ideally based in the United States or Canada, and want guidance that aligns with Western business structures, traditions and laws

Whether you’re starting from zero or trying to fix a broken foundation, this apprenticeship is designed to help you move from uncertainty and scattered effort to clarity, structure, and direction.

You don’t need to already be the most disciplined and confident to join. You do need to be willing to submit to a proven structure and follow the process. You’ll be guided step-by-step. New habits, skills and self-assurance are built inside the apprenticeship.

WHO THIS IS NOT FOR

  • You’re already earning enough stable freelance income and just want to scale

  • You’re looking for quick wins, cheats, or guaranteed income results

  • You want private 1-on-1 coaching

  • You expect someone else to do the thinking and action steps for you instead of taking responsibility for implementing what you learn

  • You see freelancing as just a side gig and aren’t serious about building a real business

WHAT YOU GET

  • Structured 12-Week Course Curriculum

  • Weekly Live Group Coaching Call (1 Hour)

  • Private Community Access with Async Support

  • Paced and Focused Format Built for Men with a Busy Schedule

This apprenticeship is a guided process designed to help you build a strong foundation so your business can thrive, not chase bandaid tactics.

Enroll: Contact Us

How The 90-Day Apprenticeship Works

This is a structured, cohort-based apprenticeship with a clear beginning and end.
It’s designed to help you build your business foundation the right way, without rushing, skipping steps, or getting overwhelmed by too many actions. This program will blend into your current busy schedule with minimal daily time investment.

I provide you the system, action steps, education, coaching and structure. YOU bring home the bacon. Results come from YOUR actions.

Program Duration and Start Dates
New apprentices start on the 1st of each month. Each cohort runs for 90 days. This staggered enrollment allows me to provide you with the best support and process.

You’re not joining an open-ended program or a content library where you passively consume information. You’re here to create real change for your business and life within a defined period.

If you need longer than 90 days, you’ll have the option for extensions. More details on that are at the end of this page.

Weekly Structure and Pacing
Course modules unlock weekly, or sooner once you complete the action steps for that lesson. Each of the 12 modules builds on the previous one. The material is sequential by design and the same sequence works regardless of whether you’re building a new business or repairing the current one.

You’ll always know what to focus on next, without needing to guess.

This is not just an online course that just gives you information without transformation. So trust the pacing and process.

One Live Group Coaching Call per Week
We meet live once per week for a 60-minute group coaching call. These calls include focused training, built around your needs, and some personalized/group coaching.

Everyone in the apprenticeship participates in the same weekly session, whether they’re new to the program or not. The calls are structured so everyone at any milestone in the program will benefit from the calls. Calls are recorded and posted to the private group feed.

Community-Based Support Between Calls
Between calls, you’ll have access to a private group where you can ask questions, share progress or advice, and learn from me and other men in the group.

This is professional, async support, not instant messaging or private 1-on-1 coaching. I will be checking the group messages at least once per week to give feedback.

Clear Expectations
This apprenticeship works when you show up, follow the build sequence, do the work, and take responsibility for your progress. If you commit to that, you’re very likely to be where you want to be in 3 months and have a business foundation that can hold real weight.

You’re not expected to be perfect, and everyone will move at their own pace with unique goals and challenges, but you are expected to engage and apply what you’re learning to the best of your ability.

This isn’t public school. You will not be tested, graded or micro-managed by your teacher. Nobody will be considered behind or ahead.

This is not a passive membership that you forget you’re paying for and later cancel because of making no progress.

What Past Students Have Said…

“Working with Chad was a decision I'm so glad I made. Since I was new in business, I was hesitant to make any financial commitments, but Chad asked important questions to help me find out what my real problem was, rather than giving general advice. After working with Chad, my schedule filled up with clients!”

- Matt H.

“It is amazing how much growth and change can happen in a short period of time. That is a clear indication of the quality of Chad’s mentoring approach. I had no idea in which direction I wanted to take my career. In just six weeks, I made significant breakthroughs.”

-Jorge F.

Joining Chad’s Freelance Family Man community and taking part in his coaching calls has been the best thing to happen to my freelance business. I’d been freelancing for about 4 years and was having a tough time getting to the consistent monthly income level I wanted. We’ve had a number of coaching sessions, and every time I’ve gotten immense value. I could say more, but if you feel like you’ve hit a wall in freelancing/Upwork or are just trying to get started, my suggestion is to simply try Chad’s FFM membership community out for a month. You don’t have to go at this alone, and working with Chad is an awesome investment. 

-Spencer T.

Meet Your Coach

Chad Gravallese

I’m a husband, and a dad of 4, first and always.

I’ve been self-employed most of my career and founded my video marketing agency, ArrowLight Video in 2015. Like many dads, my path wasn’t linear. I cycled through multiple employee jobs early on, chasing security and stability, only to discover how fragile that “security” really is.

I was laid off just months before my first son was born, and in that moment it became painfully clear that the employee path wasn’t going to give my family the stability, flexibility, or income we needed long-term.

I turned to freelancing for 9 months, failed hard, went back to an employee job until enough was enough.

I was determined to provide for my family on one income so my wife didn’t have to work. We both wanted that. She wanted to manage our home and homeschool our kids. It was up to me to make that possible for her.

So I quit my 9-5 job and made a second attempt at starting a business. This time I stopped guessing. I identified my weaknesses (and there were many), learned sales and communication, rebuilt my offers, hired coaches, and put real structure around my work.

Underneath it all, I made a choice to step out of my comfort zone, and it paid off. Within 3 months, my income climbed from $2k/month to $6k/month, just enough to pay the bills. Then my business kept growing over time, to well over $100k/year, so I could support my family comfortably on one income.

Since our kids were born, my wife hasn’t had to work, and our family has the flexibility to homeschool and build life around what actually matters. Self-employment helped us get around the system that is splitting families apart.

I built Freelance Family Man so you can succeed much faster and easier than I did, because I know what it’s like to carry the pressure of providing without a clear path forward. This program isn’t theory. It’s the structure I wish existed when I was in the middle of it.

If you would rather keep the status quo, stay where you’re at, just dabble in self-employment, and consume content without change, this will not be a good fit.

But if you’ve made it this far, chances are that’s not you.

You’re done quietly going along with the “safe” career path society expects of you.

You’re done drifting, tired of excuses, and tired of hoping things work out somehow…someday.

You want to create a life that doesn’t keep cycling in survival mode, where providing isn’t a source of constant stress, but something you carry with confidence.

You may not feel ready, but it’s time to choose to step up, do the work and become the leader your family can rely on.

Join The Founding Group

Total Investment: $597 $237

Payment Options

Paid Upfront: $200 (15% Off)

Payment Plan: $79/month for 3 months

Payment plans are offered for convenience, but the commitment is to complete the full process.

Before your start date begins, or 7 days after participating, if you decide the program isn’t for you, you can cancel and get a full refund.

Enroll Here

Why Become a Founding Member?

This pricing is intentionally lower than future groups because:

  • This is the first group

  • The structure is proven, but the delivery is being refined

  • Your feedback helps shape the apprenticeship going forward

Future cohorts will be priced at $597 or more.

What Happens After 90 Days?

After completing the 90-day apprenticeship, you’ll have the option to continue with alumni access for $21/month.

This includes:

  • Continued access to the community posts and peer group

  • Continued access to the course material

It does not include:

  • Live coaching calls

  • Ongoing coaching or feedback

This option exists if you want to stay connected while continuing to execute on your own.

If you’d like continued group coaching and live calls beyond 90 days, you can choose to extend your apprenticeship for another 90 days and you’ll be able to get the same pricing you had the first time. Alternatively you can ask about 1-on-1 coaching options.

Frequently Asked Questions

  • No. You could have never freelanced before and have no business yet or you have been freelancing part-time or full-time but struggling to earn the income you want. The foundation training process is the same either way.

  • While this apprenticeship is designed primarily for current dads in mind, it’s also a fit for young men who are married or planning to have a family in the future and want to plan ahead and build their business before the pressure is on.

  • This program is designed for men who have or will have families to provide for. The context of my trainings and coaching is framed with that context in mind so while I won’t turn away a woman who wants to be in the program, you likely won’t feel comfortable here. There are many women-led and women-focused business coaching programs out there that you can join that will better support you.

  • This program is designed primarily for US-based dads or if you’re currently living elsewhere but have US citizenship. Many of the business structure, legal, and operational guidance is specific to the United States.

    That said, men in Canada, the UK, or Australia may also find the program to be a good fit due to similarities in language, business norms and laws, and economic systems.

    Although if your time zone is too distant, you’ll struggle to attend the live calls, which will limit your engagement.

    If your home base is outside of these regions, this apprenticeship is likely not the right fit at this time. You’ll likely get more out of the general Freelance Family Man membership.

  • Plan for a few focused hours per week, 1 hour per day on average. This includes the weekly live call, working through the modules, and applying what you’re learning. This is built to accommodate those who currently have full-time jobs or businesses but it does require effort and time management.

  • The live calls are an opportunity to receive some 1-on-1 coaching depending on the size of the group and you’ll also receive some personalized feedback from me in the community feed but this is designed as a group coaching program. There is no private 1-on-1 coaching or instant messaging support.

    I offer private 1-on-1 coaching as a separate service. If you’re interested, Contact Me.

  • The program is paced to keep you focused, not rushed. Some move faster than others or experience life interruptions that cause you to miss a week. Unless you choose to share, none of the other students will be aware of your progress with the curriculum. If you don’t finish the course by the end of the 12 weeks, extensions are available.

    You’re expected to keep moving forward the best you can, not to be perfect or compare your progress with someone else’s.

  • This program is specifically for men who are still working toward stable, reliable income from their business. If you’re already there and looking to optimize or scale, this won’t be the right fit. Consider 1-on-1 coaching or contact us if you’re interested in a future program for scaling.