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3 ways serial entrepreneurship prepares you for success in business

The experience gained during a career in entrepreneurship can bring on a slew of successes. Whatever the scale of your own successes, your experience as a serial entrepreneur teaches you three important lessons.



When it comes to entrepreneurship, the statistics tend to focus on the failure rate. A study by Harvard Business School found that 75 percent of venture-backed startups fail. And research by Statistic Brain found that the first-year failure rate is between 25 and 30 percent, and that number rises to 70 percent by year 10. The good news is that this failure isn’t stopping serial entrepreneurs from bouncing back and starting another venture.

survey of 4,000 business leaders in Europe and the U.S. found that serial entrepreneurship is trending. Serial entrepreneurs make up almost half of all exporters, and they amount to 35 percent of those planning to introduce new products. Because entrepreneurs must frequently cope with failure, it’s no surprise that serial entrepreneurs are better positioned to be successful in future business than their peers.

The serial secret

Serial entrepreneurs are battle-tested individuals whose experience allows them to overcome setbacks that startups inevitably experience on the path to growth. For example, these individuals have extensive experience hiring talented individuals and setting up systems for scalable growth. While they’re open to experimentation, serial entrepreneurs typically require less of it to identify promising opportunities.

From hiring to delegating to marketing, every challenge I faced as an entrepreneur taught me invaluable lessons. Because I’ve started several companies, I’ve been able to accumulate quite a few lessons over the years, and I can bring them all with me for each new venture. As a result, I spend my time more efficiently and focus on the big picture far more than I did with my first company.

My business partner, Chris, is in a similar boat. When Chris started an underground boring company, he developed a reputation as a reliable and hardworking contractor in the utility industry. When he sold his company and started Utilimap, which provided asset management to large-scale power companies, he was able to capitalize on his previous relationships and create rapid growth. This rapid growth was eventually noticed by a larger competitor that acquired his company in 2011.

Serial entrepreneurship can also be incredibly lucrative. Michael Rubin is a serial entrepreneur whose success has brought him an estimated net worth of $3 billion. He bought a chain of ski shops before he even left home for college, and he has since started sports equipment company KPR Sports and e-commerce venture GSI Commerce — in addition to investing in the Philadelphia 76ers and the New Jersey Devils.

3 lessons from serial entrepreneurship

Whatever the scale of your own successes, experience as a serial entrepreneur teaches you these three important lessons:

1. Utilize trackable marketing methods.

Don’t just buy a billboard or place magazine ads out of desperation. Spend your marketing budget on efforts that are trackable so each purchase can prove its worth in terms of ROI. Data is extremely valuable, so collect it and store it in a way that makes it highly usable.

2. Delegate, delegate, delegate.

serial entrepreneurship

Delegate responsibilities to people who enjoy their roles and know how to perform them effectively. (Source)

We all have weak spots, but even if you’re perfectly competent at performing a certain task, chances are good that someone in your organization truly excels at it. Delegate responsibilities to people who enjoy their roles and know how to perform them effectively. This practice will help you manage your time, allowing you to focus on building the business as only you can. A career as a serial entrepreneur teaches this lesson over and over, allowing leaders to overcome the urge to micromanage more quickly with each new endeavor.

3. Focus on hiring A-team players.

As businesses grow, it’s easy for leadership to get complacent and hang on to B- or C-team employees who have been around for a while. However, replacing these underperformers with top talent will take your business to the next level. Serial entrepreneurship prepares leaders for this task by helping them build robust networks with a diverse array of contacts. Leverage your network and make strategic hires that advance your business, and help your contacts do the same in their industries.

Serial entrepreneurs are a curious bunch, which drives us to question everything around us and seek out new or improved ways of doing things. Do everything you can to encourage this curiosity because it’s also what allows us to bring new ideas from one venture to the next. Over time, the experience gained during a career as a serial entrepreneur will bring on a slew of successes.

DISCLAIMER: This article expresses my own ideas and opinions. Any information I have shared are from sources that I believe to be reliable and accurate. I did not receive any financial compensation for writing this post, nor do I own any shares in any company I’ve mentioned. I encourage any reader to do their own diligent research first before making any investment decisions.

Michael Kiel is a serial entrepreneur with a passion for boating and online marketing. He is the founder and captain of the startup Boat Planet, an online marketplace for connecting boat owners with reviewed and trusted marine professionals. He also founded a full-service inbound marketing and SEO agency that was a top HubSpot partner, as well as a commercial real estate and design firm.