How Mark Woodbury’s Dropshipping Side Hustle Led to a Career in M&A

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How Mark Woodbury's dropshipping side hustle led to a career in M&A

In the world of business acquisitions and sales, success stories often trace their roots back to unconventional beginnings. Meet Mark Woodbury, an entrepreneur from a small town in Northern California who has turned his entrepreneurial drive into an inspiring success story.

Mark developed his love for business as he pursued his passion for football at Colorado State University. Despite the rigidity of college life, it was during these years that he made powerful connections that introduced him to the world of entrepreneurship.

Mark’s transition from a humble start, including dabbling in dropshipping and launching a successful boutique brokerage, culminated in his current role as Managing Director of Raincatcher‘s Digital Division. This remarkable progression mirrors his entrepreneurial spirit – one that has guided him to a job he’s truly passionate about, where he collaborates with fellow entrepreneurs each day.

Mark’s story is a testament to the boundless possibilities that await those willing to chart their course in the digital landscape.

Small-Town Life to Webpreneurship

Mark Woodbury’s path began in a small town in Northern California. When he earned the opportunity to play football at Colorado State University, it marked the beginning of a journey that would lead him to discover his true passion – entrepreneurship.

As Mark quickly realized that the rigid structures of academic life didn’t resonate with him, he found himself surrounded by a remarkable circle of people who were forging their paths in self-employment and entrepreneurship.

“I disliked the rigid structure of college but was fortunate enough to meet a handful of people who were pursing self-employment, which made me realize that it was possible.”

These peers dared to dream beyond the boundaries of traditional employment. One friend launched a small security company, and another was immersed in the complexities of affiliate marketing. With their entrepreneurial zeal and audacious spirit, these friends ignited a spark within Mark.

Although there were difficulties and setbacks in some of these early ventures, the entrepreneurial spirit they represented greatly influenced Mark’s ambitions.

Career Transformation

Mark started his first online business as a part-time venture alongside his studies and early career. With limited capital and a humble skill set, he embarked on the journey of self-discovery and self-education. Mark began offering web development and search engine optimization (SEO) services to local businesses, with skills he taught himself using online resources like YouTube.

As he continued to hone his skills and explore opportunities in the digital realm, Mark stumbled across the concept of dropshipping in late 2013. Recognizing its potential for success, he embarked on a journey to establish a dropshipping business of his own. “I brainstormed and searched Google Shopping results and AdWords Keyword Planner for search volume and CPC bids. Eventually, I landed on a category that I believed I could have success in, being metalworking and woodworking equipment.”

His calculated risk paid off, as he successfully persuaded suppliers to partner with him to get their products to consumers. Mark’s dropshipping venture wound up as a success, but his interest in the business faded quickly.

After about a year of managing this eCommerce website, Mark decided it was time for a new challenge. His entrepreneurial itch still needed to be scratched, and he looked forward to the next opportunity.

In early 2015, Mark and his partner decided to market the business to potential buyers. Speaking about that experience, Mark said, “Once questions arose about how to get the purchase financed, how much working capital was included with the purchase, etc., we realized we were in over our head and looped in a small business broker to help facilitate the diligence and closing process.”

Despite some minor challenges, the exit was a success. They sold the site for a low six-figure sum, which “felt like life-changing money at the time.”

Through selling the business, Mark saw an opportunity for a new venture. He said, “Throughout the sales process, I realized that the historical business sales process was quite inefficient and that the business brokerage industry hadn’t quite caught up with newer business models and online-only companies.”

Upward Exits

As Mark’s journey through entrepreneurship continued to unfold, he found himself at a crossroads – a juncture that would lead him to the world of mergers and acquisitions (M&A). Recognizing an opportunity to play a pivotal role in facilitating business transactions, Mark launched Upward Exits with his co-founder Alex Shute. Upward Exits began by representing direct-to-consumer (DTC) brands before venturing into content and affiliate websites as well.  

Upward Exits carved a niche in the market, focusing on businesses earning between $200,000 to $500,000 annually. It aimed to provide a level of service above what traditional marketplaces and brokerage firms could offer – dedicated support for business owners looking to sell.

Mark’s journey with Upward Exits represented not just a career transition, but also a logical progression. Mark said, “I also thought this would mesh with my skillsets well as I studied finance and was interested in investment banking and private equity.” His background in finance, coupled with his entrepreneurial spirit, made him uniquely suited to understand the ins and outs of business transactions. 

Mark was introduced to Raincatcher through his journey with Upward Exits, which led to the next chapter of Mark’s story.


The Road to Raincatcher 

After Mark connected with the former CEO of Raincatcher, they decided he would be an ideal fit for their team in February of 2021. Mark says, “I spent some time with the partners, and we realized that there was a strong alignment with culture and skillsets and in what we were all looking to accomplish.”

Mark is now the Managing Director of Raincatcher’s Digital Division, playing a pivotal role in the company’s mission to facilitate mergers and acquisitions for businesses in the digital realm. His responsibilities are multifaceted, encompassing a range of tasks that showcase his expertise and adaptability.

Within the digital division, Mark’s focus extends to a diverse array of digitally-native businesses, including SaaS companies, e-commerce websites, content websites, and marketing services. 

While the workload is heavy and Mark and his partners must wear multiple hats in the company, Mark finds value in every bit of his career path with Raincatcher.

When asked what his favorite part of his job is, Mark says, “I have the time, money, and freedom that I desire, but that is not nearly as rewarding as having the ability to work with people I like, trust, and admire. Both my colleagues at Raincatcher and the entrepreneurs we represent inspire me on a daily basis. As Warren Buffet often says, ‘I tap dance to work in the morning.’ ”

Valuable Lessons Learned

Mark Woodbury has had a diverse range of entrepreneurial experiences, each providing valuable lessons. Aspiring web entrepreneurs can gain inspiration and insights from his journey, learning from the challenges and triumphs he has encountered along the way.

Mark’s path is a testament to the power of starting small but thinking big. His early ventures, though modest, served as building blocks for future endeavors, sending a message that the journey often begins with small steps. 

Strategic decision-making, resilience, networking, and adaptability are principles that Mark has brought to the forefront. The entrepreneurial path is inevitably marked by hurdles, and Mark’s tenacity in overcoming them demonstrates the necessity of resilience in the face of adversity. 


Mark Woodbury’s journey, from the heart of a small Northern California town to the forefront of online entrepreneurship serves as an inspiring narrative of passion, persistence, and strategic innovation. His commitment to continuous learning, willingness to embrace big and small challenges, and his knack for strategic decision-making have been the cornerstones of his success.

Aspiring entrepreneurs can draw invaluable lessons from Mark’s experiences, whether it’s the importance of starting small, the value of networking, or the need for adaptability. Mark’s story serves as a guiding light for those who dare to chart their course in the exciting world of entrepreneurship. 

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