In the dynamic world of entrepreneurship, taking risks is often a fundamental step towards achieving remarkable success. In this article, we delve into the stories of entrepreneurs who made daring decisions that paid off for their businesses.

Ross Crawford: Mr. Digital

Ross Crawford, Founder of Mr. Digital
Ross Crawford, Founder of Mr. Digital

Ross Crawford, the managing director and founder of Mr. Digital, boasts over 15 years of experience in the digital marketing space. His journey began seven years ago when he established Mr. Digital, a data-driven digital marketing agency based in Brighton, United Kingdom.

Ross Crawford’s most significant risk-taking venture involved establishing an office in Kerala, India. His primary objective was to harness the abundant pool of developer talent available in the region. Despite the inherent challenges of navigating cultural and regulatory differences, Ross embarked on this ambitious path. What made this risk even more substantial was the financial commitment required, leading him to sell his apartment to fund this venture.

Fast forward to 2023, he now leads a highly talented team of 15 individuals in India, complemented by a select group of UK-based team members. This strategic decision has propelled Mr. Digital to new heights in the competitive digital marketing landscape. The agency’s achievements include clinching the Small Business of the Year award at the Inspire Business Awards in 2020. As a testament to his success, Ross now proudly owns a charming bungalow in Brighton, complete with breathtaking sea views.

Dr. TJ Jiang: AvePoint

Dr. Tianyi Jiang, Co-Founder and CEO of AvePoint
Dr. Tianyi Jiang, Co-Founder and CEO of AvePoint

Dr. Tianyi Jiang, known as TJ, is the co-founder and CEO of AvePoint, a company specializing in optimizing SaaS operations and securing collaboration. TJ brings a wealth of expertise to his role, including a background in electrical and computer engineering. His academic journey includes earning a B.S. and master’s degree from Cornell University and a Master of Philosophy and Ph.D. in Data Mining from the Department of Information Systems, Operations Management, and Statistics at NYU’s Stern School of Business.

TJ Jiang’s journey to entrepreneurship was marked by a pivotal risk-taking moment. After a successful career as a software programmer in prominent financial institutions such as Lehman Brothers and Deutsche Bank, TJ realized his true passion lay in entrepreneurship. This realization came in the wake of the life-altering events of September 11, 2001. TJ decided to pursue higher education, eventually earning a Ph.D. in data mining and machine learning. This transition from a high-paying Wall Street job to a full-time student was a substantial risk in itself.

TJ’s risk-taking endeavors bore fruit as he co-founded AvePoint, a company that has emerged as a leader in optimizing SaaS operations and securing collaboration across various platforms. His journey from Wall Street to entrepreneurship garnered recognition, including being named CEO of the Year by the Globee Awards. TJ’s inspiring story underscores the importance of following one’s passion, even when it involves significant risks.

Justin Mauldin: Salient PR

Justin Mauldin, Founder and CEO of Salient PR
Justin Mauldin, Founder and CEO of Salient PR

Justin Mauldin is the founder and CEO of Salient PR, an independent tech public relations agency. He is a highly accomplished marketing communications leader with a track record of delivering exceptional results for dozens of fast-growing companies, ranging from prominent unicorns to emerging startups.

Justin Mauldin’s entrepreneurial journey was punctuated by a significant risk from the very beginning. His extensive experience in managing PR agencies on the client side and working for traditional PR agencies led him to a unique insight. He believed that scaling PR agencies with quality was challenging due to the prevalence of junior staff, templates, overwork, and a potentially toxic culture. Justin aspired to create a different kind of PR agency. He made a bold decision to be directly involved in managing client work, media relations, press releases, content writing, and more, instead of outsourcing these tasks to junior employees. Simultaneously, he created a network of freelancers to provide expertise when needed.

Justin’s risk-taking approach paid off as he successfully grew his business while maintaining high-quality standards. Collaborating with freelancers who excelled in their respective fields allowed him to provide top-notch services to his clients. This unconventional approach to scaling a PR agency proved to be both economically viable and efficient. Justin’s story exemplifies the importance of innovation and flexibility in the competitive PR industry.


Maggie Gerth: PROPS Luggage

Maggie Gerth, Founder and CEO of PROPS Luggage
Maggie Gerth, Founder and CEO of PROPS Luggage

Maggie Gerth is the founder and CEO of PROPS Luggage, a company born from her love of travel and her desire to solve a common travel problem. She is also a devoted mother of four daughters and is married to her husband, Bob. Maggie’s adventurous spirit extends beyond business as she enjoys paddle sports and even slalom water skiing during the summer.

Maggie Gerth’s entrepreneurial journey began with a simple idea sketched on a napkin. Frustrated by the lack of luggage racks in hotel rooms during family trips, she envisioned a suitcase with built-in legs, much like golf bags have extendable legs. This vision led her to embark on the challenging path of product development in the luggage industry, despite having no prior experience in the field.

After overcoming numerous obstacles, including multiple failed prototypes and the difficulties of navigating the luggage industry, Maggie’s determination paid off. PROPS® luggage, with its built-in legs, became a game-changing innovation in the travel industry. Her product gained recognition and popularity among travelers and airline professionals alike. Today, PROPS® luggage stands as a testament to Maggie’s dedication to solving a problem she encountered during her family travels.

Marco Bonanni: TAPNET

Marco Bonanni, Founder of TAPNET
Marco Bonanni, Founder of TAPNET

Marco Bonanni is an entrepreneur and the author of “Success Secrets.” He founded TAPNET, a platform that provides free book product and service reviews to help individuals on their journey toward self-improvement and success.

Marco Bonanni’s entrepreneurial journey began when he founded TAPNET, originally known as The Ad Place. His vision was to create a platform for local advertising, but the path was fraught with challenges. Starting a business from scratch in a competitive landscape required significant risk-taking. Despite the challenges he faced, Marco persevered and evolved TAPNET into a comprehensive digital marketing agency. This strategic shift allowed TAPNET to diversify its services and reach a broader audience. Today, the company offers a wide range of digital marketing solutions to clients worldwide.

Marco’s key to success was his commitment to continuous learning and adaptation in the fast-paced world of digital marketing. His journey demonstrates the power of innovation and determination in entrepreneurship.


In the dynamic world of entrepreneurship, taking risks is not just a choice; it’s often a fundamental and necessary step towards achieving remarkable success. The business landscape is a terrain fraught with uncertainties and challenges, and it’s those who dare to tread into uncharted territory that often emerge as trailblazers.