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Discover the freedom in shifting from a solopreneur to a fully fledged business owner, with actionable insights to make 2024 your best year yet.

Every entrepreneur has their own unique journey, and the beginning of 2024 brings a profound shift in mindset and courage as new entrepreneurs begin their journey.

Through my own experiences and insights, having founded multiple businesses and currently facilitating Bay Area Mastermind, true success, as I’ve come to realize, extends beyond the confines of solopreneurship.

It beckons a transition toward true entrepreneurship. Building a real business with a dedicated team not only fosters a financial freedom; it also gives the freedom of time, allowing you to choose who you want to work with and unlocking the true benefits of entrepreneurship.

Take the Step

The concept of waiting for the ‘perfect moment’ is a familiar one and one of the most common reasons solopreneurs don’t become true business owners. True entrepreneurship involves strategic planning; a continuous process aligned with the business’ long-term vision.

For example, waiting for enough capital to bring on team members is often followed by, “I just don’t have enough yet”. Or perhaps you have a standard operating procedure that works for you, but you haven’t developed one that is meant for a team, making it hard to retain new employees.

Having a group that will provide candid feedback on recent campaigns or strategies, hold you accountable to your goals and celebrate your successes is truly invaluable.

Drawing from my personal journey as an entrepreneur, I’ve seen firsthand the success of an organized business and a great team. With that said, every individual, industry and business is different, with their own unique challenges along the way.

However, throughout the course of my career I have coached, mentored and extensively interviewed successful business owners, asking them how they went from solopreneurs to fully fledged business owners.

While there are many variations depending on industries, individuals and other factors, I have uncovered many common factors.

Trust in Others

As a solopreneur, you are handling everything yourself. In your business, you may be the expert, but that doesn’t mean you are an expert in every part of a successful business. Sure, you wear many hats and have your hands everywhere, but it is important to realize where your weaknesses lie so you know how to build your future team.

It is important to know the ins and outs of your business, but once you realize that there are experts in marketing, IT, social media and more who can provide real value to your business, you will see the difference.


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Another issue many entrepreneurs face is being able to properly delegate. Delegation is a skill I’ve honed over the years, recognizing that empowering others fosters a culture of shared responsibility. True entrepreneurs understand that steering the ship is more impactful than manning every oar.

Micromanagement not only causes frustration with oneself, but can cause employees to feel they are not trusted and can’t do anything right. As a result, they eventually leave. This ultimately costs you more money to find, train and manage a new hire.

Collective Wisdom

Finally, I urge new entrepreneurs, even veteran entrepreneurs, to join a mastermind group. Being part of a mastermind not only gives you a virtual board of advisors supporting you and sharing your struggles, but also a peer advisory group that has overcome these challenges and can share how they did so.

True entrepreneurs understand that steering the ship is more impactful than manning every oar.

It will boost your expertise by you gaining collective wisdom from entrepreneurs in different industries with different strategies and, as I like to say, will allow you to work on your business instead of in it.

Having a group that will provide candid feedback on recent campaigns or strategies, hold you accountable to your goals and celebrate your successes is truly invaluable.

As we venture into 2024, I hope solopreneurs and entrepreneurs in all phases of their journey break free from the confines of solo venture. Entrepreneurs who embrace this, building robust businesses with the guidance of these principles, can unlock true entrepreneurial freedom.

Jeremy Shapiro

Contributor Collective Member

Jeremy Shapiro is a serial entrepreneur with a focus on software as a service, technology and information marketing. In his role as a mentor and coach to entrepreneurs, he has helped small business owners make the transition from solopreneur to business owner – an important distinction that many entrepreneurs can easily miss when working ‘in’ their business instead of ‘on’ their business. Since 1998, Jeremy has been helping entrepreneurs discover the core strengths in themselves and their businesses, and to realize their true potential by combining passion and expertise to grow their businesses and attain the freedom they deserve. https://bayareamastermind.com/coaches/jeremy-shapiro/

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