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Serial Entrepreneur or Serial Failure?

Heidi Thorne is an author and business speaker specializing in sales and marketing topics for coaches, consultants, and solopreneurs.

Do multiple unsuccessful business ventures make you a serial entrepreneur—or just a serial failure?

Do multiple unsuccessful business ventures make you a serial entrepreneur—or just a serial failure?

What Are Serial Entrepreneurs?

Through networking or online, have you ever run into people who proudly declare that they are serial entrepreneurs like it’s a badge of honor? In some cases, it truly is an accomplishment. But in many cases, this self-description is merely a cover for being a serial failure at starting and running a business. I’m always tempted to ask, “How much did you sell your last business venture for?”

Sadly, I fear the answer may be zero or a loss. Or they might have just shut down without selling.

True, being able to call it quits on an idea, project, profit center, or entire business that is not succeeding and moving on to something else takes guts, especially if it took a hefty investment of time, effort, emotion, and money. However, if that effort was jettisoned without a careful analysis of why it didn’t thrive and how to avoid the same result in the future, the potential for becoming a serial failure increases.

You’re No Fun Anymore

Launching a new business is a fun, exciting adrenaline rush. Then, when faced with the daunting daily tasks of accounting, administration, management, marketing, etc., entrepreneurs can get disenchanted with the whole thing, even to the point of just giving up and closing the business. Serial entrepreneur/failure alert!

As I emphasized in my book, Small Business Failures Solopreneurs and Self-Employed Consultants Need to Avoid!, this behavior is akin to running a kid’s lemonade stand. It’s something fun to do for now. But when it gets tough or when something more exciting (like another new business opportunity) comes along, the business comes to a screeching halt.

Consequences of Being a Serial Entrepreneurial Failure

While there may be less financial loss associated with the rapid and frequent starting and closing of small businesses these days, there are a number of issues that this behavior can cause:

1. It Becomes a Habit

Entrepreneurs who are addicted to the rush of a new business launch have their focus trained on the next new shiny object venture. Like addicts, they’re always looking for a bigger, often riskier hit, which can jeopardize their futures in so many ways.

2. It Can Hurt or Confuse an Entrepreneur’s Brand

This is the “So what are you today?” problem. The entrepreneur has so many business identities that it’s difficult for customers and colleagues to figure out what he is or what he stands for because it keeps changing. Though mega entrepreneurs (e.g., Richard Branson) have pursued many different types of ventures in their entrepreneurial careers, for the majority of small-scale entrepreneurs and solopreneurs, having too many business identities is not a way to build trust and sales.

3. It Can Drain Resources

This is like the stop-and-go traffic problem for cars. It takes a lot of energy to get going from a complete stop. So the car’s fuel efficiency is lowered in stop-and-go driving. Same for businesses. Though today it’s easier and less expensive to start a small business than it’s ever been in history, new ventures can take a huge toll in terms of time, talent, stress, and cash.

This results in low or no profits that can be used to sustain the business for continued success and, ironically, even lower the business’ ability to invest in more new ventures. A vicious cycle.

4. It Becomes an Excuse

Not making a profit? With the huge investment in serial ventures, it’s not surprising. So it becomes easy to emotionally justify being unprofitable and a failure.

What’s the ROI?

Ever watch the reality show Shark Tank? (Must-see TV for me.) The investor “sharks” are looking for how their investment in any featured entrepreneurs’ business will make them a profit. They’re looking for ROI.

Entrepreneurs would be well advised to think more like successful shark investors. This means not being in love with the process of starting businesses but being in love with the outcomes!

Thinking about outcomes may also entail thinking about exit strategies. What conditions will prompt a business closing decision? How will the business be closed? These are not motivating questions for those who just like starting businesses, but they’re necessary ones to ask nonetheless.

This article is accurate and true to the best of the author’s knowledge. Content is for informational or entertainment purposes only and does not substitute for personal counsel or professional advice in business, financial, legal, or technical matters.

© 2017 Heidi Thorne


Heidi Thorne (author) from Chicago Area on January 03, 2018:

Lawrence, I agree. Truly successful entrepreneurs create a team. They rightly realize they can't do it alone.

But you're also right in that many entrepreneurs have their eyes so trained on the prize, that they can be insensitive to others along their path. That, to me, is not building an empire; it's conquest.

Thanks so much for sharing your experience! Happy New Year!

Lawrence Hebb from Hamilton, New Zealand on January 03, 2018:


I've come across both, the 'serial' entrapeneur and the serial 'failure' and one difference I noticed, the entrapeneur builds a team in the business, they can't help it, they just look for good people and bring them on board.

About ten years ago we worked with an entrapeneur building one of his businesses, it took about a year, then he sold the two sites we helped him with for an eight figure sum, but the way he cut us off was brutal, I try to avoid these people, they can be brutal to work with.

Heidi Thorne (author) from Chicago Area on November 30, 2017:

Larry, great example! Glad your brother-in-law finally landed on a good business for him.

True, minimizing losses is paramount. It's the "live to fight another day" scenario. That way you can bolster your odds of succeeding at something that works someday.

Thanks for providing your experience to the conversation! Hope you're enjoying the holidays so far. Cheers!

Larry Rankin from Oklahoma on November 30, 2017:

I have a brother in law that has had like 10 business ventures over the years. He's finally found one that has worked.

The point is, even if you are a failure, you got to try to mininmize your loss and keep at it. Law of averages, something is bound to work eventually.

Atanas Yonkov from Bulgaria on November 24, 2017:

Thank you very much! Have a nice weekend!

Heidi Thorne (author) from Chicago Area on November 24, 2017:

Atanas, I think deciding when to move up and start something else is the toughest decision ever! And, yes, I've seen those who abandon the entrepreneurial careers after one or two attempts. You have to wonder if they really did want to do it in the first place. Thanks so much for stopping by and commenting! Have a great weekend!

Heidi Thorne (author) from Chicago Area on November 24, 2017:

Linda, agreed, it is a massive effort to launch a business, even today with all the tools and resources we have available. So that makes it all the sadder when they don't have the commitment to even try to make it work. Thanks for stopping by and chiming in! Have a great weekend!

Heidi Thorne (author) from Chicago Area on November 24, 2017:

Glad you found it helpful, Nikki! Thanks for stopping by and have a wonderful day!

Atanas Yonkov from Bulgaria on November 24, 2017:

Very good and concise article. Sometimes we should move up though and start something else. From what I have seen, most of the people just give up after the first or second unsuccessful attempt to start a business.

Linda Crampton from British Columbia, Canada on November 23, 2017:

This sounds like some more great advice, Heidi. After all the effort required to set up a business, it seems a shame to give up on it without making a major effort to get it to succeed.

Nikki Khan from London on November 23, 2017:

Interesting point for entrepreneurs’ failure in businesses.Thanks for advice dear.Highly appreciated.

Alan R Lancaster from Forest Gate, London E7, U K (ex-pat Yorkshire) on November 23, 2017:

Heidi it's a pleasure!

"Why did the turkey trot? 'Cos he saw what the farmer's got! His number's on the butcher's list, the farmer his cheque has kissed, the bird's as good as in the pot!"

Enjoy the feast!

Heidi Thorne (author) from Chicago Area on November 23, 2017:

Bill, one more for the Heidi file. :) Thanks for taking time from your holiday to read and comment. Hope you and Bev are enjoying the holiday. Cheers!

Heidi Thorne (author) from Chicago Area on November 23, 2017:

Alan, you may be right on the gambling thing! True, all new business ventures are a risk, but some are more than others. And, as you've noted, some entrepreneurial types may take more risks than they should.

Even though you're not celebrating Thanksgiving across the pond today, I want to thank you for your support and for always making me smile with your comments. Cheers!

Alan R Lancaster from Forest Gate, London E7, U K (ex-pat Yorkshire) on November 23, 2017:

Maybe it's the same excitement that comes from gambling (cards, roulette, one-arm-bandits, horses... snail racing, some people have done it!) It's a venture, like onceover in Scandinavia men went a-Viking - raiding and pillaging around the rivers and shores of western or southern Europe. You can't do that now ("whyever not?" "shame!"), you have constraints. However... Some of this 'serial entrepreneurship' could be a front for less legal business, like in the early days of mass migration to the States (even to here, and still) from southern and eastern Europe. If they've got no 'record' they do 'business' below the radar until someone they can't 'buy' gets hurt. Put up a smokescreen and you get away with murder... for a while. Then they get greedy... Or they're just harmless fantasists as we think.

Bill Holland from Olympia, WA on November 23, 2017:

What great advice, Heidi! It's going into your file of advice on this Thanksgiving Day. Happy Thanksgiving, my friend, and thank you for your friendship.

Heidi Thorne (author) from Chicago Area on November 23, 2017:

Mary, thank you for sharing your firsthand experience with us! And that is such a dramatic shift in product (Tilapia to coconuts? Wow!) that I can't even imagine the expense and effort that took. But you understood the value of analyzing your situation and pivoting (that's one of the new buzzwords) to keep your farm business sustainable.

Like you, when a huge shift in one of my business profit centers started occurring, I had to make some tough decisions and shut it down. I would not have been able to turn the tide of market trends, even if I plowed significant funding into it. Onward!

Glad to see you have a positive mindset for future endeavors. Even though you're not in the US, I want to thank you for your support on this Thanksgiving holiday!

Heidi Thorne (author) from Chicago Area on November 23, 2017:

Flourish, agreed, giving up is easy. And it's so easy to get in and out of business these days, that I don't think people have the patience to let things develop, struggle, and grow. Thanks for stopping by. Hope you're enjoying your Thanksgiving holiday!

Mary Wickison from USA on November 23, 2017:

You're right about it being costly. Even here on our small farm, we have had to completely change from raising tilapia to growing coconuts when this area suffered an unprecedented drought. That shift cost us time and money.

I think it is necessary to shake off that feeling of failure, analyse why it happened, and push forward. It is too easy to think, "it failed and so will the next one".

As you say, people love the excitement of starting a new business but not the hard work it entails to keep it going and make it profitable.

FlourishAnyway from USA on November 22, 2017:

So many people fall in love with an idea but really won’t invest what it takes to be successful— rolling up your shirtsleeves and really working hard. Not everything’s easy, but giving up is all too easy a solution.