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Escape the 'feast or famine' cycle and build a 6-figure freelance business where everyone plays by your rules (and your income is automatic) …

“I quit my job 8 months earlier than I expected"

– Susan B.

Susan was working 3 jobs and 60+ hours a week; now she earns the same from freelancing 20 hours a week (and walks her son to school every morning).

“I can finally plan my life more than a month in advance”

– Colin M.

Colin was living “gig to gig” until he unlocked the secret to signing 6-figures in retainer income. Now he knows he can book a cool trip 6 months out and plan for the future.

“I’ve accomplished more in the past 5 months than in the past 5 years”

– Anthony Y.

Anthony’s efficient, flexible business allowed him to live his dream as an expat, traveling the world with the comfort of consistent freelance income.

'I'm sick and tired of being stuck on the freelancing rollercoaster...'

When you took the leap to become a consultant or freelancer, you accomplished one of life's biggest dreams – working for yourself, from anywhere, on your own schedule and your own terms.

You remember the thrill of saying goodbye to your demoralizing day job, once and for all. The joy of working long, late hours to build a business that was truly yours. The exhilaration of scoring that first client and cashing that first check. You were finally free.

And then, you realized it was up to you – and only you – to keep it all going.

When you had a big month, work was fun and life was easy. When you had a downturn, it felt personal. You asked yourself, "Am I really cut out for this?" When your bank account balance dwindled, you started to wonder: "Would I be better off with a real job?"

If you looked to other freelancers or consultants for help, chances are, they just smiled knowingly. "Welcome to my world," they'd sigh. "It's a never-ending cycle of feast and famine."

I used to think the same thing. Not anymore.

After more than a decade of experience and experimentation, I’ve learned that the popular wisdom is wrong. The feast-and-famine cycle is not a necessary evil, and it's not an inevitable trade-off for the benefits of being your own boss. It is a symptom of specific problems in your business that you can permanently solve.

You're already great at what you do. You deliver extraordinary creative and technical services, and your clients walk away happy. You just need a trusted ally to help you with the job behind the job – the one where you build a predictable, sustainable, serious business based on your existing talents and skills.

Without that business foundation, it’s all too easy to stay on the same old grind for years, saying things like...

“I’m on the rollercoaster of feast and famine. The big months are great, but I’m always anxious because I don’t know what’s coming next.”

“I could work 24/7 and still never get everything done. There’s no boundary between work and life.”

“I’m always wearing multiple hats … when I have a rush of projects, I’m too slammed to write proposals and sell new business.”

“Clients only care about cost. How can I earn more when they already think I’m expensive?”

These are the questions of skilled creators who haven't yet built a sustainable business that turns creativity into a career. If this sounds like you, you're not alone.

I've been there, and I've spent the past 14 years experimenting, studying, succeeding, failing, and devoting my life to building a business that actually lives up to my dreams. Along the way, I've helped my fellow freelancers and consultants apply the same lessons to their lives – dramatically increasing their incomes and making life and work a hell of a lot more fun.

The result? A clear, straightforward system for building consistent, predictable profit – without spending your whole life doing sales, without getting bogged down in the "busy-ness" of business, and while delivering amazing work to clients. And most importantly, while having fun doing your job.

The path isn't easy – you'll have to pass by lots of discouraged freelancers and starving artists along the way. But if you're ready to put in the work and invest in yourself, I'm ready to show you the inner workings of a thriving freelance career.

It's time to leave the cycle of feast and famine behind – and replace it with continuous growth. As you adopt the Automatic Freelancer system, you'll shift from hoping to sign your next project to stay afloat, to being assured of ongoing retainer and repeat-client income.

Introducing Automatic Freelancer, the secret to building predictable profit as a freelance web designer or developer.

Rob HowardI’m Rob Howard, the CEO of Understrap and Howard Development & Consulting, and the creator of Automatic Freelancer. For 20+ years, I’ve been on a full-time journey to build a thriving career as a freelancer, consultant and solo entrepreneur. Like you, I deliver high-end creative and technical services to clients – primarily in web development, augmented with interdisciplinary knowledge of design, advertising and publishing. And like you, I struggled for years to make it work as a real income stream.

Early on, most of my successes were accidental: a serendipitous introduction to a new client, a random project that paid more than the rest. Over time, I pushed myself to learn more, try everything, and book up on the inner workings of a successful consultancy. From hundreds of books, blogs and courses, I'd pluck ideas and give them a try. There was a ton of useless noise out there – but some concepts and approaches really clicked. Thanks to all that study and experimentation (and a lot of failure), after five years without a real job, I crossed over from running a sputtering business to earning a serious, professional, full-time income.

Since then, I've honed my process, crunched my data and begun sharing what I've learned with friends and colleagues in similar businesses – the first students of Automatic Freelancer. After seeing their businesses grow for years thanks to the systems I helped them build, I'm now sharing the same knowledge with you.

My businesses have been featured in Newsweek, U.S. News & World Report, Entertainment Weekly, Quartz and TechCrunch. My clients have included Harvard University, MIT and The World Bank. Today, I'm more than a decade into a life as a profitable, predictable freelance business owner. These tools and strategies have helped me live abroad (and take my clients with me), move across the country (with zero friction), start a family, and have both the time and the money to make most of every moment along the way.

I've always had an entrepreneurial spark and a love for building businesses – but it's much more than that, too. When I see a student earning more, that's a great start. But there are a lot of ways to generate income, and most of them are not accompanied by a higher quality of life. When I see a student with a totally new mindset (and a new trajectory through life to go with it) – that's when I know we've accomplished something that really matters.

Automatic Freelancer includes...

  • Lifetime access to all course material, so you can learn at your own pace and revisit it anytime.

  • 37+ in-depth video lessons, with step-by-step guides you can follow to grow your freelance business. Full closed-captioning on every video.

  • The exact, word-for-word proposal templates I use on every client project, plus my proprietary project-fee-calculator that allows me to write quotes in less than 30 minutes.

  • Two special live Zoom Q&A sessions for all Automatic Freelancer students – join me on Zoom and ask me anything. The events are on November 18 and December 7 – if you can't make it, submit your questions in advance and we'll share the recording.

Here's how the course works...

A four-week journey to a predictable, profitable freelance business.

Automatic Freelancer is a detailed, step-by-step guide to leveling up your freelance business. I've documented the exact systems I've used to scale from being a small-time solo freelancer (back in 2008) to running a highly profitable small business (repeatedly exceeding $200,000 a year in profit) as a web developer.

In the past few years, I've used the foundation I show you in Automatic Freelancer to start hiring a larger team and acquiring software companies, including the world-renowned Understrap theme framework. Without the strategies in Automatic Freelancer, I never would have had the consistency or profitability to make those leaps to building a larger company.

I've designed Automatic Freelancer as a four-week guided tour through everything you need to earn a six-figure income as the owner of a small web design or web development firm. Each week, you'll learn about a new topic – from retainers to direct client outreach to choosing a niche to preparing yourself to scale. Each weekly module is packed with in-depth videos tutorials and the exact proposal templates, calculators and other written tools that I still use every day with all my real-world clients.

A month from today, you'll be experiencing an absolute transformation of your freelance business – from one with unpredictable ups and downs, to a business with a clear, profitable trajectory for the long-term. Here's a complete outline of everything you'll learn...

Week 1: No-Brainer Retainers

Recurring revenue is the key to establishing long lasting financial security, and I want you to get there as soon as possible. That’s why I don’t waste any time getting to the good stuff.

Our very first sprint is all about creating and selling retainers that are… well… total no-brainers to your clients. That’s because my “Hybrid Retainer” approach combines measurable deliverables with intangible benefits, resulting in easy-to-offer, customizable retainers your clients actually want to buy. By the end of this sprint, you’ll have a simple, powerful retainer you can offer every single client (with 3 size options to fit any budget) and the confidence to start selling retainers and creating reliable income immediately.

Week 2: Rockstar Clients On Demand

Now that you’ve created your No-Brainer Retainers, it’s time to get lots of new clients in the door and start raking in that recurring revenue. In Sprint #2, I’ll teach you my simple, proven formula for identifying who your ideal clients are, how and where to find them and how to reach out in a way that’s calm, confident and most importantly — converts!

This sprint does NOT include content marketing, social media, sleazy sales tactics or any other “magical” passive income system. Just good old fashioned relationship building with clients that are both fun to work with AND profitable for your business. By the end of this sprint you’ll have a step-by-step plan for attracting and closing dozens of what I like to call “Clients for Life”.

Week 3: Crafting Irresistible Offers that Sell Themselves

By Week #3, you’ve got new prospects lining up around the block, which means it’s time to streamline the rest of your business so you can focus on the important things: your family, your relationships, your health, and everything outside the office. In this sprint, we’ll build a fixed-fee project menu full of sizzling offers that will make your clients drool (and send your competition running out of the kitchen).

I call this process the “30-Minute Profitable Proposal System,” and it’s the cornerstone to earning more income while spending less time on sales. By the end of this sprint you’ll have an elegant, strategic system to calculate confident quotes and create professional, high-ticket proposals in a matter of minutes.

Week 4: The Psychology of Scaling Up

By now, you’ve built a full-fledged freelance business that’s on track to earn 6-figures a year or more… Now it’s time to think about scaling. This week is all about removing yourself as a bottle-neck, delegating and serving more clients WITHOUT slipping back into the feast-or-famine grind.

During this week, you’ll learn how to set meaningful boundaries, maintain a healthy work-life balance and deliver top-notch work to your clients, all at the same time. By the end of this sprint, people around you will wonder how you get so much done but still seem to have unlimited time to devote to your family, friends and personal growth.

Here's your full curriculum...

Automatic Freelancer includes 37 in-depth video lessons, plus downloadable tools to help you take action fast.

    1. Sell Less, Earn More

    2. Live Hybrid Retainer Workshop (Freelance Business Week Denver)

    3. The Secrets of the Hybrid Retainer

    4. The Complete Hybrid Retainer Proposal Template

    5. The Hybrid Retainer Brainstorming Worksheet

    6. The Counterintuitive Unlimited Access Plan

    7. Becoming a Trusted Expert and Friend

    8. Bonus: The Recurring Revenue Transformation

    9. Workshop: Learning to Love Commitment

    1. The REAL Ideal Client Formula

    2. How To Track The Right Data – So You Can Make Smart Decisions

    3. No More Unicorns: How To Target Clients You Can Actually Find

    4. Download: The Client Profit-Per-Hour Worksheet + Calculator

    5. Workshop: Mike Discovers His Ideal Audience

    6. Workshop: Targeting the Right Audience Without a Big Portfolio

    7. The Magic of Exclusivity: Rapid Qualification and Sales

    8. The Most Powerful Way to Build a Pipeline (... and what not to waste your time on)

    9. How The 'Active' Pipeline Changes the Game

    10. Workshop: Susan Hones Her Exclusivity Pitch

    11. Workshop: Writing a Powerful Outreach E-mail

    12. Nurturing Your 'Not Yet' Leads

    13. Clients that Keep Coming Back

    14. Referrals (and Playing the Long Game)

    15. Workshop: Prospecting Success & Why High-Pressure Tactics Make Life Worse

    16. Workshop: Keeping Up Your Momentum as You Build Your Pipeline

    1. The Shocking Power of the Fixed Fee

    2. Building Your Project Menu

    3. Bonus: The Irresistible Offer That Makes Competition Irrelevant

    4. Download: The Fixed-Fee Proposal Template

    5. Raise Your Prices, Risk-Free

    6. Creating Your 30-Minute Profitable Proposal

    7. Download: The 30-Minute Profitable Proposal Worksheet + Calculator

    8. How To Negotiate With Clients (And Win)

    9. Bonus: The Personal Finance Framework for Sudden Income Surges

    1. Before You Delegate, Eliminate

    2. Never Check E-mail Again

    3. Workshop: How to Defeat Scope Creep

    4. Eat Dessert First

    5. The 'Money Machine'

    6. How To "Turn Off" a Thriving Business

    7. The Dark Art of Firing Clients

    8. Hiring Help – And Beyond...

    9. Bonus: The Hidden Financial Formula of High-End Freelancing

    1. Live Q&A Session: November 18

    2. Live Q&A Session: December 7

About this course

  • $500.00
  • 45 lessons
  • 17.5 hours of video content

What students are saying...

'Instrumental in helping me grow my business'

– Anthony Yeung, Digital Marketing Consultant

"Rob has been instrumental in helping me land deals, navigate the life of a self-employed consultant, and grow my business. It’s not just his experience that sets him apart, but his commitment to constantly improving."

'I have virtually unlimited leads'

– Mike Kohl, Web Developer

"Rob was tremendously helpful as I was stuck in my lead generation process. Because of my time with him, I now have virtually unlimited leads to go after."

CASE STUDY: ‘I went from zero to $100,000 a year in retainer income…’

“I just got introduced to a new client, and it was such a smooth conversation – she found me, talked for one afternoon, and signed up the next day. It was like – wow, I didn’t know it could be this smooth and low-stress.

Colin had been freelancing for years and was living “gig to gig.” He was always in reaction mode, putting out fires and worried about selling the next job to stay afloat.

After learning how to create irresistible retainer offers in Automatic Freelancer, Colin is no longer “hunting” for clients – he’s booked solid, and very picky about which new work he takes on. His client interactions are less transactional and more about building lasting relationships, taking all the sleazy sales pressure out of the equation. And he’s earning way more than at he did at his old 9-5 tech job.

“I have more flexibility in my life and a higher sense of security of knowing what next month is going to look like financially. I can do things like plan for travel 6 months out, whereas before I had no idea what my finances were going to look like in 6 months.”

Now, Colin wakes up bright and early, not out of stress and anxiety but because he actually wants to start the day and work on his business. He can plan for the future and book travel in advance because he has complete confidence in his income, months and years in the future.

CASE STUDY: ‘I was able to quit my job 8 months earlier than I expected…’

For two years, Susan struggled to get her consulting business off the ground.

She was signing good projects here and there, but she wasn’t making enough recurring revenue to confidently quit her day job. It all added up to 60+ hour weeks and the feeling that she wasn’t making any progress.

After discovering her ideal client and creating a powerful set of project and retainer offers in Automatic Freelancer, Susan’s freelance retainers replaced 100% of her full-time salary, and she was finally able to set out on her own.

“Once I sold that first retainer, the dominos just started falling. My last day of my full-time job is Friday and I was able to quit 8 months earlier than I expected.”

Now, Susan works 20 hours a week, makes the same amount she did when she was grinding away at her full-time job, and she gets to walk her son to school every morning, something she could never fit into the schedule before.

Meet Your Instructor

CEO of HDC Rob Howard

Rob is the CEO of HDC and the Publisher of MasterWP. Based in Denver, he brings 20+ years of full-stack development experience and an eye for design, publishing and communication to the MasterWP Workshops team.

Rob is a graduate of Syracuse University. He's been featured in Wired, Entrepreneur, Entertainment Weekly, Newsweek and TechCrunch, among many other major publications. His clients have included MIT, The World Bank, Marriott and The United States Holocaust Memorial Museum.
The World Bank
Colorado State University
Colorado Dept. of Public Health and Environment
United States Holocaust Memorial Museum

Is Automatic Freelancer right for me?

The course will help you level up your freelance or consulting business – but it's not right for everyone. The most successful students check these boxes...

  • You provide creative or technical services, such as design, programming, writing or marketing

  • You have 3+ clients and are on track to earn $30K+ this year

  • You're a solo business owner or part of a small team (and all your partners are committed to improvement, too)

  • You're ready to commit at least a few highly focused hours a week to improving your business

  • You want to build a highly profitable, full-time business you love ... not chase magical, passive income from the beach

This is not right for you if...

  • You're just starting out. You'll need data from at least three clients or projects for these systems to help you level up.

  • You're moonlighting and don't plan to go full-time with your freelance or consulting business.

  • You're earning more than $200K a year from your business. You may get a few valuable takeaways, but this course won't change the game for you. (Stay tuned for more advanced material.)

  • You want to hire staff to solve all your problems. This course is about building an extraordinarily efficient, profitable system with a very small team, so you can grow exponentially once you have a solid foundation.

  • You're stuck in your ways. This course intentionally challenges the conventional wisdom and looks at hard data and real dollars-and-cents. Prepare to exit your comfort zone.

Our unbeatable 60-day money-back guarantee

Try Automatic Freelancer for a full 60 days, risk free.

Your investment is protected by our unconditional 60-day 100% money-back guarantee. Try the full course for 60 days, and if you aren’t blown away by the course for any reason, we insist that you get 100% of your money back.

Just e-mail us within 60 days and we’ll provide a full refund. That means you can start building your freelance business today, 100% risk-free.

Try Automatic Freelancer, Risk-Free.

I've designed the course to pay for itself with your first new (and improved) client.

Your enrollment is backed by my unbeatable 60-day 100% money-back guarantee.

Frequently Asked Questions

  • How long do I have access to the course?

    You have lifetime access to all course material – so you can take it at your own pace and build your business in the way that feels right for you. There's at least 3 to 6 months worth of big wins packed into 37 lessons, so plan to play the long game and implement Automatic Freelancer over the course of many months.

  • What if I get busy and fall behind?

    The course is entirely self-paced – you can speed through it and implement over time, or you can watch each lesson and digest it slowly. Either way, you have lifetime access, and you'll be able to implement the specific strategies and tactics in the course for many years to come.

  • What if the course isn't right for me?

    First, I encourage you to take your time and make sure you're ready to fully commit before you enroll. To get the most from this program, you should run a creative or technical service business, have at least 3 clients, and be on track to earn $30K+ this year. You should be ready to spend 3+ hours a week improving your business.

    I promise an unconditional 60-day 100% money-back guarantee. If you aren't blown away by the program for any reason, I insist that you get 100% of your money back. Just e-mail me within 60 days and I'll provide a full refund. That means you can start growing your business today, 100% risk-free.

  • Will the live sessions be recorded?

    Yes, you'll have the opportunity to submit questions in advance (if you can't make the live sessions on Zoom) and will receive full recordings of both live sessions.

Automatic Freelancer includes...

  • Lifetime access to all course material, so you can learn at your own pace and revisit it anytime.

  • 37+ in-depth video lessons, with step-by-step guides you can follow to grow your freelance business. Full closed-captioning on every video.

  • The exact, word-for-word proposal templates I use on every client project, plus my proprietary project-fee-calculator that allows me to write quotes in less than 30 minutes.

  • Two special live Zoom Q&A sessions for all Automatic Freelancer students – join me on Zoom and ask me anything. The events are on November 18 and December 7 – if you can't make it, submit your questions in advance and we'll share the recording.

Imagine a future that's all feast, no famine.

You’re on the verge of getting off the freelance rollercoaster for good – and unlocking the secret to building a predictably profitable freelance business.

That means no more questions from family and friends about when you’re getting a “real job.” No more jokes about whether or not you wear pants to work. No more anxiety and stress over the seemingly endless cycle of feast and famine.

And most importantly, no more longing to fulfill your true purpose or wondering if you’re on the right path.

Instead, you’ll stroll into your office each morning, do work that you LOVE for clients that you enjoy working with, and rest easy at the end of the day knowing you’ve got reliable cash-flow booked for the long term.

There’s a lot of freelance advice out there. You could cobble together a plan from a grab-bag of Top 10 lists, self-help books, questionable “common wisdom” and whispered advice from friends. But let’s be honest – the chances that this cacophony of Internet nonsense will actually lead you to a simple, focused, powerful blueprint for a flexible, profitable business are slim to none. 

With Automatic Freelancer, you can instantly unlock a proven, meticulously documented, data-driven formula for 6-figure freelancing. 

I’ve invested 20+ years learning how to make my freelance business automatic. That includes thousands of hours of reading, learning, testing and failing – again and again – before finding the techniques that worked. I’ve spent tens of thousands of dollars on education, courses and conferences and at least 4,000 business days in the trenches.

Everything I’ve learned – thoroughly tested and perfected – is packed into this course. And now, it can all be yours.

Don’t waste precious time and energy making the same mistakes I did. Join the Automatic Freelancer today and skip the stress, hassle and sleepless nights…

Try Automatic Freelancer, Risk-Free.

Your enrollment is backed by my unbeatable 60-day 100% money-back guarantee.

'A teacher who makes complex challenges feel simple'

– Margo A.

“Rob has this really clarifying way of explaining things – unlike other courses I’ve taken and instructors I’ve seen. He’s a great teacher, and he executes. He’s action-oriented, but the way he shows you what actually matters is so, so helpful.”

'Literally changed my life'

Colin McCann, Security and Performance Specialist

The ideas that Rob introduced me to, and how to authentically integrate them into my business, have literally changed my life in ways that are difficult to describe. My clients are better, my income is not only much higher but far more consistent, and the flexibility I have with my day is unmatched.
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