4 Strategies for Success as a Serial Entrepreneur

Not everyone is destined to be an entrepreneur, but with the changing world economy, an increasing number of people are exploring it as an alternative.

In one recent study, researchers estimated that more than 40% of American workers will be independent by 2020. This includes freelancers, contractors, and temporary employees.

So whether you’re already running a company or just thinking about it, this guide will help you increase your odds of doing what most entrepreneurs never will: string together several big wins.

Successful serial founders like David Cancel and Hiten Shah are a rare breed. They’ve managed to launch one successful business after another, stair-stepping their way to bigger and more exciting projects.

Here are four habits that you need to succeed as a serial entrepreneur.

1. Build Personal Relationships in Your Industry

“I wouldn’t have got anywhere in the airline industry without the mentorship of Sir Freddie Laker [founder of Laker Airways]. Find a mentor.”

– Richard Branson, founder, Virgin Airways

Building a network is vital to any entrepreneur. It’s more than a list of potential clients and service providers – it’s every serial entrepreneur’s secret weapon.

Strategic alliances with the right people can either make or break your venture. A solid piece of advice at just the right time, or a getting the chance to work with someone who has deep experience in your industry can be game-changing.

Bonus benefit: you can leverage the relationships you’ve forged from one business to jump-start the next one. Instead of cold emailing for your first client, you can often make a few phone calls (or email your list) and get customers from day one.

Instead of growing a LinkedIn network of thousands of connections, build a solid foundation of 30 highly-skilled individuals that will help you expand. In this case the quality of your contacts trumps the quantity.

The benefits of a strong network can’t be stressed enough. They include: Shared knowledge, linking with people who have similar mindsets, discovering new opportunities, getting support – and personal enrichment from rewarding relationships.

Action Item: Identify one person who’s already built the exact type of business you want (in terms of revenue, lifestyle, size, industry vertical, etc.). Email them. Or simply offer to pay for 20 minutes of their time on Clarity.fm. Kindle a relationship by asking smart questions, taking their advice, and following up with your results.

Click Here to Learn How Drip Can Grow Your Business

2. Make Smart Hiring Decisions from the Start

Just how important is your choice of who you hire?

Anthony Smith used his own experience as a small business owner in the development of Insightly, a SaaS CRM application. He decided to move from Australia to Silicon Valley for one reason: The chance to hire the right people.

It was a bold move, but it paid off. Smith knew all about the importance of hiring the right team. He explains:

“By delegating responsibilities, skilled employees can take on new tasks. This is why it’s important to make smart hiring decisions from the beginning.”

If your strategy is sound, and you’re on the path to becoming a serial entrepreneur, at some point you’re going to have to step out of the management role. Hiring the right people will ensure your startup doesn’t fall to pieces when you move on to the next project.

It takes time to sift through hundreds of applicants, so it makes sense to find creative ways to narrow down the list to just a handful of ‘stellar’ applicants. Avoid the giant recruitment platforms with generic job offers. Instead, search for experts on niche sites or ask for referrals on your LinkedIn network. Another solution is to hire just one person who’s talent is hiring the right people.

Action Item: Start treating hiring like any other skill set. You need to read books, craft a process, and iterate based on feedback.

Need a mind-blowing book on hiring for startups? Here are a dozen.

3. Work on Improving Your Own Psychology

Why is it that most entrepreneurs fail?

There are many reasons. But one of the most underrated reasons is mindset.

Serial entrepreneurs don’t string together multiple wins without facing significant obstacles. If you want to succeed in business, you might as well train your brain to respond positively to inevitable obstacles.

In Serial Winner: 5 Actions To Create Your Cycle of Success, author Larry Weidel (who built several companies in the financial services industry) explains how to create a cycle of success long-term, despite temporary circumstances.

Weidel breaks down five steps that entrepreneurs can take to create their own cycle of success. He advises:

  • Move forward when you feel stuck. Instead of stagnating, make the decision to keep building on what you’ve already accomplished. Keep the momentum going.
  • Crush early doubts and give yourself the best shot at succeeding. Instead of feeling stymied because your ideal opportunity hasn’t come yet – get out there and create it.
  • Overcome obstacles to win anyway. In other words, be realistic about your abilities, but don’t let that stop you.
  • Maintain your mental toughness until you cross the finish line. Focus on what needs to happen next, and don’t allow anything to distract you.
  • Avoid the winner’s trap and use the momentum of each win to achieve the next. There’s no time to rest on your laurels.

In Weidel’s view success isn’t the final destination, or the single pinnacle of an event – it’s something that becomes a habit. It’s about cultivating the permanent habits that turn into a cycle of success.

Bonus Reading: The Obstacle is the Way by Ryan Holiday dives into more specific strategies for responding to challenges. And the book has made its way onto the bookshelves of NFL coaches and players, so you’ll be in good company reading it.  

Action Item: Challenge yourself to see your next business obstacle as an opportunity. If you lose a customer, call them and ask them why — and use their exact language to improve your marketing and retention. Your next bad day is an opportunity to start practicing how you want to respond.

4. Find a Business Model That Can Scale

Paul Graham famously wrote, “Do things that don’t scale.”

That’s great advice when you’re getting started. But one of the best things about the Internet is the opportunity to make companies scalable and achieve rapid growth.

Instead of a linear model where more income necessarily requires more expenses, an exponential model can grow fast without the same costs.

Usually there’s a big initial cost, but running costs are kept low by minimizing the need for staff, maintenance and service. It’s the ideal way to let technology work for you. Plus, once you scale one startup into a valuable company, you can command a multiple that funds bigger, more exciting projects.

Ways To Make Your Business More Scalable

  • Keep your business model, and your business plan really simple, standard and consistent. Strip it down to the bare essentials, while keeping your core idea intact.
  • Automate everything that can be automated. If you’re a regular reader of this blog, you already know that marketing automation is essential. But there are online tools that can help you automate other repetitive tasks, such as inventory, accounts and project management.
  • Outsource everything that isn’t essential. To be more scalable you want to avoid anything that’s labor intensive or that constantly require the addition of more staff members. Peripheral tasks like bookkeeping, payroll and social media management are ideal candidates for outsourcing.
  • Make yourself unnecessary as far as possible. In other words, your scalable business can become a lot bigger if you don’t limit it by trying to do everything yourself. You need to step out of running the business in order to guide its growth, while allowing a capable team to get on with what they’re good at. Then move on to the next source of income.

Action Item: Ask yourself: “what else can I delegate?” If you don’t have a virtual assistant, go to Virtual Coworker right now and buy 10 hours as a test drive. Once you start offloading repetitive and administrative tasks, you will free up time to think strategically and do the work that only you can do.


While some people will always prefer the security of a regular paycheck, entrepreneurs excel at designing their own future – even if it’s risky. While building a sustainable income is one thing – creating a series of successful ventures is quite another.

Have you been thinking of turning your online business into a series of wins? If so, remember to keep the following points in mind:

  • Think in an exponential way instead of linearly. A scalable business is infinitely easier to manage.
  • Put the right people in the right positions from the start to ensure a sense of continuity.
  • Build a network of like-minded people around you – and utilize their skills, knowledge and experience.
  • Instead of dreading bad news in your business, turn obstacles into pivots and improvements.

And if you’re ready to grow faster so you can start your next project, now’s a great time to…

Try Drip and Automate Your Marketing

Have you started your journey as a serial entrepreneur? What strategy did you choose? Share your thoughts with us in the comments section below!