How to be a Successful Under 30 Entrepreneur

SmallBizChat on TwitterEvery week as SmallBizLady, I conduct interviews with experts on my Twitter talk show #SmallBizChat. The show takes place every Wednesday on Twitter from 8-9pm ET. This is excerpted from my recent interview with Michael Simmons @MichaelDSimmons. Michael is an award-winning serial entrepreneur who started his first business at age 16. He’s the bestselling author of The Student Success Manifesto. Hiscompany, Extreme Entrepreneurship Education, has worked with hundreds of colleges & universities to help young people become more entrepreneurial through books, in-person and virtual events, and an online mentorship software. For more information:

SmallBizLady: What is the single most important thing that potential small business owners under 30 should know?

Michael Simmons: They should know that it’s possible. I know that sounds very basic, but a very small percentage of young people even realize that entrepreneurship is a viable career pathway.  A survey of high school students found that this number was only in the low single digits. If you don’t think something’s possible, then you definitely won’t take the necessary steps in order to be successful at it.

SmallBizLady: How do you get young people to believe that entrepreneurship is a viable career pathway?

Michael Simmons: Based on my company’s experiences on over 500 campuses with the Extreme Entrepreneurship Tour (, the first critical step is people being exposed to role models they can relate to. Our goal is always to get audience members to the point where they think to themselves, “If he or she can do that, so can I!” We want to avoid people thinking, “This person was only successful because they had xyz advantage. I don’t have that so I can’t be successful.”

SmallBizLady: What are keys to a good role model?

Michael Simmons: I’ve found that the more similar a role model is to someone, the more they can relate to them. What makes someone similar varies depends on the person. Different key factors for types of role models are:

  • Age
  • Ethnicity
  • Gender
  • Perceived Intelligence
  • Financial Upbringing
  • Where They’re From

At the end of the day, the sign that someone is a good role model for someone is emotional awakening where the individual is inspired to do something that they previously thought was not possible.

The other sign of a good role model is that the person has actually accomplished what you want to accomplish. That way, their advice isn’t based on theory; it is based on practice.

SmallBizLady: Once people believe in themselves, what’s the best way to get them started?

Michael Simmons: There are some people who can simply hear how to start a business and then they’ll start taking action. If those people don’t know something, they’ll find the missing information on their own. Realistically, 99% of people are not like that. They need to be put in some sort of program that provides ongoing support and accountability that will give them momentum.

SmallBizLady: How can people interested in entrepreneurship programs find the best program for them?

Michael Simmons: You can see one of the most comprehensive lists of national organizations serving entrepreneurs at To find local organizations, I would recommend searching for SCORE, SBDC, Co-Working, and Accelerator offices in your community. From there, you can ask these organizations for referrals to other organizations. If you’re in school, I would see if your school has an entrepreneurship program.

SmallBizLady: When evaluating programs, what are some keys to look for?

Michael Simmons: In starting a business, momentum is key. If you get enough momentum, you reach the point of no return. That point is where it is actually harder to stop than it is to keep on going.

I would look for entrepreneurship support programs that focus on helping you get momentum rather than just theoretical knowledge.

SmallBizLady: Once someone gets started, how can they avoid failure?

Michael Simmons: I would first distinguish between types of failure. There is business failure and personal failure. Business failure is when a business goes out of business. Personal failure is when you give up on yourself and take yourself out of the entrepreneurship journey. I think the biggest cause of business failure is personal failure.

I don’t want to completely minimize the importance of business how-to knowledge. However, I do think that people overestimate it. That knowledge can be learned with practice, but once you take yourself out of the game and stop practicing the skill of entrepreneurship, then you will not succeed.

SmallBizLady: What should people’s expectations be about the entrepreneurial journey?

Michael Simmons: When people have the expectation that entrepreneurship is easy and that success will come quickly, they’ll label themselves as a failure and give up too soon. For people who look at it as a journey, they’ll look at failures as learning lessons and keep improving. Even if the first business someone starts doesn’t work, a long-term entrepreneur will realize that they are much better prepared to start the next business.

SmallBizLady: What is the best way for young entrepreneurs to raise money?

Michael Simmons: Young entrepreneurs starting today are lucky that there are now a number of funding sources for aspiring entrepreneurs with low incomes, no assets, and little credit history. If you’re looking for debt, I would recommend searching for local micro-enterprise organizations at or using crowdfunding platforms like KickStarter, Indiegogo, or Fundable. If you’re looking for equity investments, I would recommend applying to a startup accelerator and also creating a profile on

SmallBizLady: Entrepreneurship is a humbling process. What are specific strategies that people can use to keep up their motivation?

Michael Simmons: I think the first phase involves introspection and taking time to understand what is the most meaningful for you in life. I personally like to build businesses around what’s most meaningful to me, even if that business is not a mainstream business and people don’t immediately understand it. Secondly, I think the key is setting up things so that achieving your goals becomes a MUST rather than THAT WOULD BE NICE. Once things are a must, they get done.

SmallBizLady: How can young entrepreneurs take advantage of being young?

Michael Simmons: Young entrepreneurs have a number of competitive advantages as a generation. First, young entrepreneurs understand how to reach other people their own age better than people from a different generation. Secondly, Generation Y is the first generation to grow up with the Internet. A lot of things that Generation Y entrepreneurs take for granted in terms of their technical skills are much harder for people who are older to understand and apply. Finally, young entrepreneurs have much less to lose, and they’re at a phase in life where it’s easier to take on more risk.

SmallBizLady: What are the two biggest mistakes people make in entrepreneurship?

Michael Simmons: I would say that the two biggest mistakes that people make when it comes to entrepreneurship are 1) Not getting started 2) Not keeping on going and improving. If you don’t make these two mistakes, then your success is a matter of time rather than a matter of chance.

If you found this interview helpful, join us on Wednesdays 8-9pm ET follow @SmallBizChat on Twitter. Here’s how to participate in #SmallBizChat:

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  1. says

    I do enjoyed the twitter chat last night. I however feel that if you don’t understand finances or take the time to learn them that can be a huge obstacle in your buisness. It is necessary for you to know what money is coming in and from where and know where it is going as well.

  2. says

    I think it’s also important to know what expenses to take on. You don’t need the very best furniture. You don’t need a huge Google Adwords budget for broad terms.

    You do need a website that can rank well in relevant terms, and that can convert people into customers.

  3. says

    I enjoyed reading the transcript of this Twitter chat. Michael Simmons covered both fundamental steps to take as well as the importance of the proper mindset, which is easily overlooked with young people. We often have the energy and enthusiasm, but can quickly get discouraged when immediate results don’t occur.

    The quote about most business failures actually coming from personal failures was a great insight.

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