What Is a Serial Entrepreneur?

- SmartAsset 3/6/22, 4:55 PM

Share Tweet

What Is a Serial Entrepreneur?

Mark Henricks | OCT 30, 2020

SHARE

A serial entrepreneur starts several

businesses one after another rather than
beginning one venture and staying focused
on it for many years like a more typical
entrepreneur. Serial entrepreneurs may sell
their businesses after they reach a certain
level of maturity. They may retain ownership
while delegating day-to-day managerial
responsibilities to other people. Or, if the
business is underperforming, they may close
it down and move on to the next idea. Some highly successful businesspeople are serial entrepreneurs.
Startups organized by serial entrepreneurs are generally regarded as attractive opportunities by
knowledgeable venture investors.

It’s not uncommon for people to start businesses, experience failure and then try again. Serial entrepreneurs
are generally seen as a different sort because of their track record of starting multiple successful
enterprises. Find an Advisor

There is no standard number of businesses that someone has to start to be considered a serial
entrepreneur, but three may be a minimum. Nor do all the businesses have to succeed or produce profits.
However, most people regarded as serial entrepreneurs have at least a couple of significant and enduring
successes to their credit.

https://smartasset.com/small-business/serial-entrepreneur Page 1 of 7
What Is a Serial Entrepreneur? - SmartAsset 3/6/22, 4:55 PM

Pros and Cons of Serial Entrepreneurs

While each startup has unique characteristics,
the process of beginning a new business
does have some steps that are common to
most if not all entrepreneurial ventures. Serial
entrepreneurs learn from experience,
sometimes the hard way by making mistakes,
how to get an idea for a business in motion
and off the ground. Along with developing
skills, they acquire contacts among investors,
talented employees and others who can help
them with the next enterprise.

Venture capital investors have expressed a preference for backing companies founded by serial
entrepreneurs because of the value the experienced startup leaders bring. This preference isn’t only for
serial entrepreneurs whose past startups have all been successes. Failure can be a good teacher, according
to this viewpoint, and past failure can pave the way to future success.

The practice of serial entrepreneurship can come with some limitations and risks as well as benefits. For one
thing, a serial entrepreneur who builds and sells a startup that later achieves great success can miss out on
the chance to acquire great wealth by cashing out too soon.

Another risk is that soon after starting a business a serial entrepreneur will be distracted by an idea for a
new startup. That may lead the entrepreneur to fail to pay enough attention to the first business so that it
flounders and is unsuccessful.

Examples of Serial Entrepreneurs

https://smartasset.com/small-business/serial-entrepreneur Page 2 of 7
What Is a Serial Entrepreneur? - SmartAsset 3/6/22, 4:55 PM

Many high-profile entrepreneurs have come

to attention because of their long-term
association with a single startup. Microsoft co-
founder Bill Gates, who is not thought of as a
serial entrepreneur, is an example of one of
these. However, serial entrepreneurs have a
special way of gaining public attention
because of their repeated, sometimes
spectacular, successes in a variety of fields.

One of the best-known serial entrepreneurs is Richard Branson, who has begun hundreds of ventures in
fields from airlines to soft drinks, all under the Virgin label of his first company, a mail-order record firm. Many
of Branson’s new companies have been folded after failing to achieve traction. But Branson’s multiple wins
in such diverse fields is one matched by few other serial entrepreneurs.

Oprah Winfrey is another serial entrepreneur who parlayed an early success into the foundation of a diverse
empire, this one focused on media. Winfrey has started prominent players in television production, cable
television and magazine publishing.

A more recent arrival to the scene, Elon Musk, began as a web software entrepreneur, moved to online
financial services and has since been upending industries from tunnel construction to space transport.
However, he joined Tesla, the electric car company that may be his most prominent venture, after it was
founded.

The Bottom Line

Serial entrepreneurs go from one idea for a new business to the next, starting companies and then selling,
closing or delegating them to others to manage. While their track record may not be one of perfect repeated
success, their hard-won experience and demonstrated diligence makes serial entrepreneurs attractive to
some new venture investors.

Tips for Entrepreneurs

Starting even one business is a complex and uncertain process. Before taking it on, consider working
with an experienced financial advisor. Finding the right financial advisor who fits your needs doesn’t
have to be hard. SmartAsset’s free tool matches you with financial advisors in your area in five

https://smartasset.com/small-business/serial-entrepreneur Page 3 of 7
What Is a Serial Entrepreneur? - SmartAsset 3/6/22, 4:55 PM

minutes. If you’re ready to be matched with local advisors who will help you achieve your financial
goals, get started now.

Keeping close rein on a startup’s expenses is critical. There are four tips for doing that successfully.
It’s also essential to squeeze every dollar spent to get the most out of it.

Photo credit: ©iStock.com/Drazen_, ©iStock.com/alvarez, ©iStock.com/ra2studio

MARK HENRICKS

Mark Henricks has reported on personal finance, investing, retirement, entrepreneurship and other topics for more than 30
years. His freelance byline has appeared on CNBC.com and in The Wall Street Journal, The New York Times, The Washington
Post, Kiplinger’s Personal Finance and other leading publications. Mark has written books including, “Not Just A Living: The
Complete Guide to Creating a Business That Gives You A Life.” His favorite reporting is the kind that helps ordinary people
increase their personal wealth and life satisfaction. A graduate of the University of Texas journalism program, he lives in Austin,
Texas. In his spare time he enjoys reading, volunteering, performing in an acoustic music duo, whitewater kayaking, wilderness
backpacking and competing in triathlons.

Was this content helpful?

Yes
No

Share Tweet

RELATED POSTS
7 Mistakes Everyone Makes When
Hiring a Financial Advisor
20 Questions to Tell If You're Ready to
Retire
The Worst Way to Withdraw From Your
Retirement Accounts

MORE FROM SMARTASSET

! Compare Up to 3 Financial Advisors Near You

https://smartasset.com/small-business/serial-entrepreneur Page 4 of 7
What Is a Serial Entrepreneur? - SmartAsset 3/6/22, 4:55 PM

! Mortgage Calculator

! How Much Do I Need to Save for Retirement?

! Calculate Your Capital Gains Tax

! Should I Refinance My Mortgage?

! Compare Mortgage Rates

CATEGORIES

! Advisor Resources

! Auto

! Career

! Checking Account

! Credit Cards

! Credit Score

! Data Studies

! Debt

! Estate Planning

! Financial Advisor

! Insights

! Insurance

! Investing

! Life Insurance

! Mortgage

! Personal Finance

https://smartasset.com/small-business/serial-entrepreneur Page 5 of 7
What Is a Serial Entrepreneur? - SmartAsset 3/6/22, 4:55 PM

! Personal Loans

! Refinance

! Retirement

! Small Business

! Student Loans

! Taxes

GET IN TOUCH SMARTASSET

Contact About

Careers SmartReads

Captivate

SmartAdvisor

Press

SmartAdvisorMatch

GET SOCIAL LEGAL STUFF

Like on Facebook Terms of Service

Follow on Twitter Privacy Policy

AdChoices

GLB Notice

Online Tracking Opt-Out Guide

https://smartasset.com/small-business/serial-entrepreneur Page 6 of 7
What Is a Serial Entrepreneur? - SmartAsset 3/6/22, 4:55 PM

SmartAsset Advisors, LLC ("SmartAsset"), a wholly owned subsidiary of Financial Insight Technology, is registered with the
U.S. Securities and Exchange Commission as an investment adviser. SmartAsset’s services are limited to referring users to
third party registered investment advisers and/or investment adviser representatives (“RIA/IARs”) that have elected to
participate in our matching platform based on information gathered from users through our online questionnaire.
SmartAsset does not review the ongoing performance of any RIA/IAR, participate in the management of any user’s account
by an RIA/IAR or provide advice regarding specific investments.
We do not manage client funds or hold custody of assets, we help users connect with relevant financial advisors.

Smartly made in NYC © 2022 SmartAsset, all rights reserved.

... ...

https://smartasset.com/small-business/serial-entrepreneur Page 7 of 7