Entrepreneurship: The Second Time Around

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Four thoughts on how serial entrepreneurs can best apply lessons from their earlier forays as founders.

By Sarah Merrion Isaacs (CEO, Conventus)

For some startup leaders, launching another company after an initial foray into entrepreneurship is comparable to marrying for the second time, which Samuel Johnson famously described as "the triumph of hope over experience." It’s true that entrepreneurship, like marriage, can be an all-consuming experience. It’s also true that second-time entrepreneurs can apply lessons learned in the first go-round to make the next venture more successful.

For first-time entrepreneurs, taking a look at the processes, options and possible pitfalls of launching a new company with the benefit of a second-timer’s hindsight might also be helpful. Second-go startups are like second marriages; they still require hard work, even with gained experience. Here are four thoughts on entrepreneurship the second time around:

Pay Close Attention to Organizational Development

In fiction and theory, entrepreneurship nearly always entails a genius new concept, with the inventor single-mindedly focused on bringing the idea to life in product form, and it’s natural and necessary for an entrepreneur to focus on her product or service and spend a lot of time perfecting it. Beware, however, of being uni-dimensional.

It’s just as important to focus on growing the company around the product. A positive company culture, sound organizational infrastructure and effective processes and procedures don’t happen by accident. As a second-time entrepreneur, I learned to give this building process its due and make the commitments necessary to develop it from the get-go.

Remember that Your Reputation Depends on Making Great Hires

Whether it’s your first, second, third or tenth venture, it’s important to never lose sight of the fact that your team is your company, as far as your customers are concerned. Sometimes you’ll be lucky enough to have a great group come together during the development phase. Recognize that you’ll need to build and manage that team. This is key to sustaining a great reputation.

For first-time entrepreneurs who are focused on getting product and service delivery just right, it can be tempting to think that all you need to do is build a great product and find some warm bodies to deliver it to your customers. But anyone who has actually managed a company can tell you that putting the right team in place and supporting it will ensure high quality outcomes.

Keep an Open Mind About What’s Really Important

When you’re busy perfecting your product, organizing your company and building your team, it’s easy to fall into habits of thinking that may not help you achieve your ultimate goal. For example, with my first venture, I assumed it was important to have a brick-and-mortar business presence to create the kind of company culture I envisioned.

But as my second venture began to evolve from the first, that assumption was turned on its head. The second venture took shape when our customers reported a hole in the market, and we assembled a team to develop a new technology solution. The technology and function was completely separate from the first venture, so it made sense to launch a new company. But as the new venture formed, it became clear that we already had a vibrant, productive culture:  Our high-performance virtual team demonstrated that it was possible to excel without a brick-and-mortar location, a "requirement" that turned out not to be so important after all.

Toward a Successful Venture

Success doesn’t mean doing everything perfectly the first time, and it’s especially important to remember, as an entrepreneur, the saying that, “perfect is the enemy of good." Learning from failures and unexpected opportunities or consequences is valuable in building new ventures. No matter if this is your first, second or third venture, you’ll learn lessons along the way that can help you run your present company – and any future businesses you start – more effectively and efficiently.

As you get started, remember to pay close attention to how you develop your organization: The patterns you establish and the team you assemble will have far-reaching effects. While learning from experience, don’t forget to question any assumptions you’ve made along the way about how your company should be structured. By focusing on the fundamentals and keeping an open mind, you can find success the first – or second – time around. 

Sarah1About the guest blogger: Sarah is CEO of Conventus, an information security consulting firm that protects companies from security attacks and data breaches. Conventus specializes in optimizing the performance and use of endpoint and server security software. The company also offers incident management and PCI, HIPAA, and SOX security compliance consulting.