He Built A Billion Business By Turning Online Transactions Into Relationships
Oisin O’Connor built a formidable eCommerce company by bootstrapping it for years before taking outside investor money. Now they’ve raised almost $300M to empower even more businesses to go online. During our interview on the Dealmakers Show O’Connor shared how he discovered he was just cut out to be an entrepreneur, the importance of knowing yourself, and what you are not great at, as well as finding the right market and timing. Plus, the advantages of building a remote-first company, and the pros and cons of waiting to raise money.
Oisin O’Connor built a formidable ecommerce company by bootstrapping it for years before taking outside investor money. Now they’ve raised almost $300M to empower even more businesses to go online.
During our interview on the Dealmakers Show O’Connor shared how he discovered he was just cut out to be an entrepreneur, the importance of knowing yourself, and what you are not great at, as well as finding the right market and timing. Plus, the advantages of building a remote first company, and the pros and cons of waiting to raise money.
Listen to the full podcast episode and review the transcript here.
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Here is the content that we will cover in this post. Let’s get started.
- 1. Born To Build Things
- 2. BBQ & Bootstrapping
- 3. The Pros & Cons Of Bootstrapping Your Business Startup
- 4. Meritocracy & Building A Remote First Company
Born To Build Things
Oisin O’Connor was born and raised in LA, after both of his parents had immigrated from Ireland to the US.
They were both architects, who taught him creativity, design thinking and about building things from a young age. This took him to school for architecture, and then economics. He also came to the realization that in today’s modern world the logical evolution of builders is the entrepreneur. That got him interested in computer programming.
His parents were adamant that he went out and got a real job. He ended up at Deloitte. Though quickly realized that one of those old traditional jobs just wasn’t what he wanted to do at all.
During college he had been involved with an organization that had provided microfinancing and medical relief in Central America. It really impressed upon him the power of technology to help people around the world.
So, his first entrepreneurial venture was Empowered.org. A crowdfunding organization that aimed to help communities and projects. Unfortunately, crowdfunding for nonprofits was slow to take off. It was his first experience in that while you can get a lot of things right, if the timing isn’t there you still don’t have the market to support a fast growing startup.
BBQ & Bootstrapping
At a BBQ in LA Oisin ran into Mike Flynn. They were worth both trying to work on software projects, and quickly hit it off.
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