How Startups Support Freelancers With Entrepreneurial Aspirations

The modern workforce is witnessing a significant shift towards freelancing, with more professionals seeking career independence and flexibility.

Freelancers and startup founders share common traits, such as self-reliance, passion for their work, and a willingness to embrace uncertainty. As a result, many scholars interested in the industry are prone to asking, “Is a freelancer an entrepreneur? The evidence suggests that they are, as many look to transition into successful startup founders eventually.

Therefore, this blog explores how startups can play a vital role in supporting freelancers’ entrepreneurial mindset, nurturing their talent, and facilitating their growth toward running their own companies.

The similarities between freelancers and startup founders

Startup founder doing work on a laptop

History is peppered with instances of freelancers eventually starting their own businesses and becoming successful entrepreneurs. The ability to learn their trade by contracting with different companies gives them unfettered access to how founders style their business models and earn money.

Already familiar with being their own boss, many freelancers realize the next logical step is to focus on building their own small business and provide existing clients with a service and solution that meets expectations.

The following are just a few characteristics that startup founders and freelancers share.

Independence and self-reliance

By nature, freelancers work independently and are responsible for their success. They manage their time, seek clients, and deliver projects with minimal external guidance. Similarly, startup founders must be able to make critical decisions, set a clear vision for their business, and navigate challenges without a corporate safety net.

By recognizing these shared traits, startups can better understand and relate to the needs of freelancers aspiring to become entrepreneurs. If they happen to engage with an outsourced hire that provides stellar freelance work, they can impart valuable knowledge that might benefit them in the long run.

Pursuit of passion and purpose

Man climbing a rockface at sunset

Freelancers choose projects that align with their interests and skills, enabling them to perform at their best.

Similarly, startup founders often embark on entrepreneurial journeys fuelled by a compelling vision to solve problems or bring a transformative product to the market.

Many startup founders capitalize on this shared desire for purpose-driven, self-employed work and create an environment that nurtures freelancers’ passions and long-term goals. Over the last decade, and especially since Covid-19, this relationship has been fruitful for both parties – offering end clients more choices when selecting the right people to perform essential tasks.

Embracing uncertainty and taking risks

Freelancers are no strangers to uncertainty as they navigate project-based work, income fluctuations, and variable client demands.

Similarly, startup founders face a myriad of uncertainties, from market reception to funding challenges.

Both freelancers and founders are willing to take calculated risks, learn from failures and adjust their strategies accordingly. Startups can acknowledge and celebrate this shared risk-taking spirit, fostering an atmosphere encouraging innovation and experimentation.

The path from freelancer to entrepreneur

Man climbing a rockface at sunset

Unlike full-time jobs, where employees have assigned tasks and job descriptions prescribed when they commence employment, freelancers change tasks weekly, if not daily.

Unrestrained by management’s expectations, freelancers acquire a mindset that they can earn a living under their own steam. The logical step for many is to start their own business, where they complete the cycle by hiring freelancers for their own projects.

Understanding the challenges of entrepreneurship

Freelancers often have an advantage when transitioning to entrepreneurship as they have first-hand experience dealing with the challenges of managing their own time, finances, and resource allocation. They understand the importance of effective time management, client relationship-building, and delivering high-quality work.

Startups can leverage this valuable experience and develop it further by providing mentorship programs or networking events, allowing freelancers to learn from seasoned entrepreneurs.

Acquiring diverse skills through freelancing contracts

Freelancers work across various projects and industries. One day they could work for a marketing consultant, and the next for a social media management company. For most freelancers, these learned skills often extend beyond their core expertise, encompassing project management, brand consulting, communication, and client negotiation.

In some cases, remote workers acquire contracts with big corporations; in others, the job could perform tasks for a new business. Through solid performance, this results in repeat work. The more freedom a freelancer has to experience different work modes, the more entrepreneurial they are likely to become.

Startups can recognize the value of this developing entrepreneurial mindset and actively seek freelancers who demonstrate adaptability and a willingness to learn. By integrating freelancers into their teams, startups can tap into this knowledge base and foster a culture of continuous learning.

Significance of business skills when transitioning to a startup founder

To become successful startup founders, freelancers must augment their skill sets with essential business skills. These skills include financial management, marketing, strategic planning, and team leadership.

Startups can facilitate freelancers’ development by organizing workshops, seminars, or webinars on relevant topics. This benefits freelancers in their entrepreneurial journey and helps startups build a pool of talented individuals who may become future co-founders or critical team members.

How startups are developing the next generation of entrepreneurs

Freelancer outside on a laptop with papers

As the demand for freelancers grows, many startups and small businesses recognize that they must allocate resources toward developing freelancers’ skills to attract the best talent. This strategy benefits both parties as the company can extract the best possible result from dedicated talent. At the same time, the freelancer can engage in relevant professional development that will grow the career on an upward trajectory.

The following are a few ways startups can nurture those freelancers who show considerable aptitude within the startup ecosystem.

Offering mentorship from experienced entrepreneurs

Mentorship plays a pivotal role in guiding aspiring freelancers toward entrepreneurship.

Startup founders can collaborate with experienced entrepreneurs or industry experts to create mentorship programs where successful freelancers can seek advice, gain insights, and receive valuable feedback on their entrepreneurial endeavors. This mentorship enhances freelancers’ skill sets and helps build a sense of community and shared vision.

Providing exposure to entrepreneurial experiences

Startups can create an entrepreneurial ecosystem that allows freelancers to observe and participate in various aspects of the business. By involving freelancers in brainstorming sessions, strategy meetings, and product development discussions, startups can offer invaluable exposure to the entrepreneurial process.

Such experiences foster a sense of belonging and encourage freelancers to explore the idea of entrepreneurship further.

Collaboration and the exchange of knowledge

Collaboration is a hallmark of both freelancing and entrepreneurship.

Using the latest project management software, teams can share ideas, exchange knowledge, and potentially find fellow outsourced hires worth working with in the long term. The startup community can be a fertile ground for nurturing freelancers’ entrepreneurial ambitions.

Understanding the pitfalls of business ownership

Man worrying about money

Many entrepreneurs find that business ownership is much different than working on a contract-to-contract basis as a paid freelancer. Of course, employees who work for a monthly salary don’t need to worry as much about financial security as those who ply their trade in the gig economy.

Whether paying taxes, dealing with compliance issues regarding staffing, or general cash flow management, things can get stressful when you run your own company.

Equally, freelancers experience nerve-wracking moments when contracts dry up as feast and famine cycles can swing wildly. That is why the step up to startup founder, while challenging, is not as shocking as it would be if you were coming straight from a nine-to-five.

Financial management and budgeting challenges

Man doing financial calculations

As freelancers manage their income and expenses independently, they gain insights into budgeting and financial planning.

However, transitioning to entrepreneurship demands more financial acumen, including managing startup costs, revenue projections, and long-term financial sustainability. Acting as a guiding hand, startups can provide resources and training to freelancers on these crucial financial aspects, softening the blow considerably.

Balancing work and personal life as an entrepreneur

Freelancers already experience the challenge of maintaining a work-life balance. However, entrepreneurship can intensify this struggle, as founders often invest heavily in their businesses.

With a wealth of knowledge regarding flexible work arrangements, the need for downtime, and the importance of self-care, startup founders can educate freelancers on burnout and prioritizing mental health over work.

Freelancers often handle basic administrative tasks, such as contract agreements and invoicing.

However, as entrepreneurs, they encounter more complex legal and regulatory requirements. Startups can provide access to legal expertise, services, and resources, helping freelancers better understand and comply with relevant laws, thus mitigating potential risks associated with business ownership.

Quickly Hire: Matching talented freelancers with entrepreneurial startup founders

Asian startup founder looking happy and pointing at something

At Quickly Hire, we regularly see how the partnership between startups and freelancers is mutually beneficial. With over 100 talented freelancers worldwide in our network, many of whom are aspiring entrepreneurs, they work hard to bring unique skills and perspectives to the startups we serve.

We recognize the shared traits and aspirations freelancers and founders share, and that is why we work hard to pair individuals with similar skill sets that complement each other.

Our community fosters a nurturing environment that encourages freelancers to pursue their entrepreneurial dreams and a place for successful startups to impart their knowledge to others in the ecosystem.

By recognizing the collaborative spirit between startups and freelancers, innovation, creativity, and sustainable growth in the modern business landscape becomes a normality.

If you are a startup founder or small business owner searching for the perfect freelancer to collaborate and complete pressing tasks, we encourage you to contact us!


  • Alex McInnes

    Alex is Quickly Hire's content strategist and digital marketer. He's a New Zealand-born, Thailand-residing copywriter extraordinaire. Dad to two beautiful girls, Alex loves playing rugby, reading, and running with his soi dog, Effie.

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