Chelsea Winstead’s Online Money Maker Review — Can You Start Freelancing Without Any Digital Skills?

March 15, 2024

Online Money Maker is a free freelancing class by Chelsea Winstead and Hollie Prescott. It teaches you how to begin your own freelancing business and leave your 9-5 job. Chelsea and Hollie quit their corporate jobs after finding financial freedom through freelancing.

The program covers the essentials of starting a freelancing business. It begins by explaining digital services and freelancing. Then teaches two methods of offering services: hourly and output-based. Chelsea also discusses the potential earnings in various niches. She then finishes it by promoting the Online Business Builder.

Being a freelancer can be highly profitable. Research shows 31% of freelancers make $75,000 or more annually. However, it's important to note that the industry is quite crowded. Statistics reveal that 71% of U.S. workers are planning to freelance in 2024. There are currently 73.3 million freelancers in the United States. Is Online Money Maker the best option to start freelancing?

If you’re looking for an alternative option, consider local lead generation through the rank and rent model. The freelance market is overcrowded, with millions of freelancers worldwide, making it hard to stand out. In contrast, local lead generation focuses on 20 to 30 companies in your area, giving you a targeted approach. With this business model, you create a lead-generating website and rent it to local businesses, earning passive income. While there's still competition, it's more manageable than the freelancing industry. 

Online Money Maker Pros And Cons


Online Money Maker is free.

Chelsea and Hollie are both successful in their niche, making 6-figure income.

Online Business Builder is also free.

You can have access to their growing community.


It has no coaching and mentoring.

It contains only the basics that you can also find on different platforms.

Freelancing industry is already crowded.

They’re more focused on catering to women.


Online Money Maker is free.


You can join their community, which is Online Money Maker w/HerHQ. 


Online Money Maker started in 2022.


The community already has 16.1K members on Facebook.

Can You Start Freelancing Without Any Digital Skills? 

No, starting freelancing with no digital skills is not recommended. Freelancers rely heavily on technology and digital platforms to deliver their services. Without digital skills, you may find it challenging to compete in the freelance market and meet client expectations. For example, if you're a graphic designer, you need proficiency in design software like Adobe Photoshop or Illustrator to create high-quality visuals. Without these skills, it would be difficult to produce professional designs that meet client requirements.

Similarly, if you're a writer, digital skills such as using word processing software, and understanding content management systems are crucial. Clients often expect freelancers to be familiar with these tools and processes, and lacking digital skills can put you at a disadvantage.

Having digital skills allows you to communicate and collaborate with clients and other freelancers. Most communication in the freelance world happens through digital channels like email, messaging apps, and project management platforms. Without proficiency in these tools, it becomes challenging to show your ideas, share files, and stay organized.

Fortunately, there are many online resources available to help you develop digital skills. You can find tutorials, courses, and communities where you can learn and improve your digital proficiency.

What Do I Get In Online Money Maker?

With Online Money Maker, you will get lifetime access to their leaving corporate portal. This portal contains five videos that run for over 16 hours, giving you valuable information. Plus, you can become part of their growing community and connect with others who are on the same journey.

Lesson 1: Why We're Here

In Lesson 1, Chelsea introduces herself and her mission to help women make more money, have more options, and empower them. She shares her background as an Air Force officer and IT project manager. The lesson focuses on providing clear steps for working online and avoiding scams.

Lesson 2: Digital Services

This lesson discusses digital services to make money online. Digital services are "done for you" services provided to businesses. By offering these services, freelancers solve business owners' problems and get paid upfront. Chelsea highlights that digital services need fewer skills compared to other methods, like affiliate marketing. Making it a simpler and faster way to earn money without relying on consumer purchases or ads.

Lesson 3: Selling Digital Services

Lesson 3 explains two ways to sell digital services. Starting with freelancing platforms helps gain confidence and navigate the online space. You can go from hourly work to fixed-price packages, allowing freelancers to maximize their skills and income.

Lesson 4: Actual Hourly Rates

Chelsea highlights the potential to earn significantly in freelancing in this lesson. She explains that many freelancers are making two to three times the amount they currently earn in corporate roles. Chelsea provides examples of hourly rates for various digital services. Copywriting, social media management, project management, and email marketing, ranging from $30 to $65 per hour.

Lesson 5: Leaving Your 9-5 Job

This part outlines the five steps to leave your 9-5 job and start making money online. Chelsea encourages those serious about making money online to join the Online Business Builder.

Who Are The Creator Of Online Money Maker?

The creators of Online Money Maker are Chelsea Winstead and Hollie Prescott. They are the Founder and Co-founder of Her HQ, an organization dedicated to providing women with more opportunities to make money online. Both Chelsea and Hollie are successful multi-six-figure online business owners.

Chelsea Winstead is a former Air Force officer and corporate IT project manager. She transitioned into the online space and scaled her project management business to earn $50k per month within a year. Chelsea serves as an Online Business Manager (OBM) and Operations Strategist. She specializes in implementing sales tactics, using price anchoring techniques, and building confidence among service providers. Chelsea has collaborated with esteemed companies such as CEO School, Jenay Rose, The Nutrition Addiction, and Guide Culture. She established herself as an expert in operations and leadership for 7-figure companies.

Hollie Prescott, a former marketing manager, pursued her dream of traveling the world with complete freedom. She transitioned into the online space and offered website and branding services, charging $10k to $15k per project. Hollie made the bold decision to leave her role as an Advertising Account Manager at McCann. Hollie quickly gained a reputation as a sought-after brand strategist through word-of-mouth referrals. She works with notable companies such as BossBabe and Club Life Design. She showcases her expertise in creating long-term marketing strategies for scaling businesses.

Is Online Money Maker Worth It?

The Online Money Maker program is worth it as a starting point for freelancing. It is a free, concise class that provides essential information for entering the industry. Chelsea effectively explains the payment process and potential earnings for digital services. Additionally, you can take part in the Online Business Builder, a free program that guides you through the 5-step process of leaving your 9-5 job. It's a risk-free opportunity to explore freelancing and determine if it aligns with your career goals.

Chelsea and Hollie’s 3-Step Program

Step 1: Online Business Builder

Online Business Builder is a self-paced program designed to teach you the skills to make money online by offering digital services. In this program, you will learn about the various digital services available, discover strategies for finding clients, understand the essential techniques required to earn money online and gain insights on securing your first few beta clients.

Who is it for?

  • Online Business Builder is for aspiring freelancer who want to make money online without falling for "get rich quick" schemes.
  • It is for someone who has skills but is unsure how to translate them into an online business.
  • It is for beginners who feel that their current income, job, or life is not aligned with their goals and desire for more freedom and income.
  • This program is to empower everyone who believe they are destined for greater things.

What's included?

  • Lifetime access to the comprehensive curriculum.
  • Access to the Online Business Builder workbook.
  • Membership to the private Online Business Builder Facebook community for guidance, support, and assistance.

5-Steps To Leave Your Job:

  • Step 1: Understanding and selecting a digital service to offer.
  • Step 2: Setting up essential business foundations required to work with remote clients.
  • Step 3: Reviewing the tech platforms for effective communication and support with remote clients.
  • Step 4: Exploring strategies for finding digital clients and connecting with potential leads.
  • Step 5: Providing guidance and a checklist for successfully transitioning out of your 9-5 job and preparing to quit.

Step 2: Foundation

The Foundation is a live program that provides a structured learning experience to equip you with the essential sales and marketing skills required to establish a six-figure online business.

Who is it for?

  • It is for someone who excels in their skills but face challenges in effectively marketing their value.
  • It is for people who are tired of working with "low budget" clients and aspire to be recognized as industry leaders.
  • This is for beginners who desire to shift from hourly rates to being compensated based on the value they provide.
  • Foundation is for anyone who seeks clarity, confidence, and direction in their business, including defining their offerings, determining to price, and effortlessly marketing their services.

What's included?

  • Access to a close-knit, private group of like-minded freelancers.
  • A 12-week experience with weekly curriculum drops, homework, and actionable tasks for fast progress.
  • Personalized feedback, support, and guidance to help you shape the long-term vision and goals for your business.

Step 3: Accelerator

The Accelerator is Her HQ's most comprehensive program. It is designed for maximum support and impact. Chelsea and Hollie are currently working on revamping the program this year to bring you even more valuable content and resources.

Who is it for?

  • It is for someone that is ready to take her business to the next level and scale.
  • Everyone who understands the value of strategic planning and wants to maximize the impact of her work.
  • This is for you if you desire more time and space to make a bigger impact.
  • Anyone who wants to elevate her business without compromising the results for her clients.

Is Freelancing Still Worth It In 2024?

Freelancing is still worth it in 2024, particularly because of the pandemic's impact. According to Fiverr, 78% of companies plan to rely on freelancers instead of hiring full-time staff. This shows the high demand for freelance services. However, the industry is already crowded, with 1.57 billion freelancers worldwide as of 2024. Looking ahead, the number of freelancers in the USA is projected to reach 90.1 million by 2028. Despite the competition, freelancing can still be a passive income stream while working full time.

How Much Do You Actually Get Paid In Freelancing? 

Here are different niches in the freelancing industry and their average hourly rates sourced from Upwork:

  • Freelance Writer: Earns between $30 and $40 per hour or $42,000 per year.
  • Freelance Data Analyst: Makes, on average, $55–$65 per hour and $100,000 per year.
  • Freelance Editor: Often makes between $25 and $35 per hour and around $40,000 per year.
  • Freelance Programmer: Typically makes $60–$70 per hour and around $120,000 per year.
  • Freelance Photographer: Earns between $35 and $45 per hour or around $42,000 per year.
  • Freelance Developer: Makes between $50 and $60 per hour and around $1 million per year.
  • Digital Marketer: Often makes $50 per hour and $1 million per year.
  • Mobile App Developer: Earns between $55 and $65 per hour, or $1 million per year as a freelancer.
  • Freelance Transcriptionist: Typically makes between $20 and $25 per hour or $32,000 per year.
  • Graphic Designer: Charges $40–$45 per hour, with annual pay of roughly $90,000.

How Do Freelancers Get Paid?

Here are the common ways freelancers receive payment:

  • Hourly Basis: Freelancers are paid a predetermined fee per hour for the work they perform.
  • Monthly Basis: Some freelancers receive regular monthly payments based on the expected workload for that month
  • Project Basis: Freelancers receive a fixed fee for completing a specific job with a defined scope and deadline.

Online Money Maker Alternatives

The Headquarters™ Package by The Hemon Group is an online program that helps freelancers build a scalable service funnel. With a 3-step system, participants can position themselves as top-tier digital talent in their market. The package includes a core curriculum, personalized feedback on homework, and three weekly live coaching calls.

Price: The Full-Ride Headquarters™ Package costs $997.

More Info: Headquarters™ Review

Freelance Domination is an online course by Daniel that teaches people how to start and succeed in their own online freelance consultancy. Daniel, an experienced freelancer, quit his job in 2011 and began his own venture with little money and free time. This course is designed for industries where online freelance work can be done easily and without complications.

Price: Freelance Domination costs $1,297.

More Info: Freelance Domination Review

Can Freelancing Offer Ticket To Passive Income?

Yes, freelancing can offer a ticket to passive income, but it is not the best option. You must consider the competition in the industry. With over 1.57 billion freelancers worldwide and about 79.6 million freelancers in the USA by 2025, the market is already saturated. It leads to intense competition for clients.


However, local lead generation offers the best ticket for passive income. It involves creating and optimizing websites to rank highly in search engine results for specific local keywords, then renting those websites to local businesses. By focusing on this niche approach, you can tap into a smaller, more targeted market of 20-30 companies in your local area. This strategy allows for higher chances of success, the potential for ongoing passive income streams, and the ability to build long-term relationships with clients.

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Ippei Kanehara

$52K per month providing lead generation services to small businesses is for digital hustlers, industry leaders and online business owners.

His #1 online business recommendation in 2024, is to build your own lead generation business.

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