Nine Lessons I’ve Learned From Interviewing Young Entrepreneurs

by / ⠀Entrepreneur Interviews Startup Advice / June 20, 2013


For the last year, I’ve had the honor of authoring the young entrepreneur interview series here at During that time, I’ve spoken to over 40 of the most talented, passionate, innovative and hardworking individuals I’ve ever met. In addition to being consistently inspired, educated and entertained by their stories, I’ve been given a unique glimpse into the entrepreneurial mindset that has relevance to business people of any age.

Over time, certain themes have emerged in these conversations. Here are a few of the most prevalent ones I’d like to share with you now.

1) Follow your passion.

This is probably the thing I’ve heard most. The road to starting your own business is going to be fraught with unending obstacles, long work hours, and many ready-made opportunities to bail. If you don’t absolutely have a burning desire to make this business happen, don’t even bother.

2) Do your research.

Everyone has good ideas. Most of them will not get off the ground, and even fewer of those will succeed over the long haul. One of the key ingredients to success is knowing your market and understanding your competition. Make sure that your business is filling an actual need, and not just something you hope will gain traction.

3) Make lots of mistakes.

Iteration is at the heart of the lean startup model. A few of the people I spoke to have even suggested that it is the only genuine way to learn. Painful, yet effective. Along these lines, one of my favorite notions is that the truly innovative company remains in a state of perpetual beta. Honestly, in order to remain relevant and responsive to the changing needs of the marketplace, it does make sense to be constantly evolving.

4) There is no one size fits all.

There are companies that were bootstrapped from friends’ couches for months or longer. There are small businesses that are functioning well with two or three principals, and it’s the perfect model for all involved. Some companies have grown exponentially with significant outside investment, expanding from local to regional to national with surprising alacrity. Others have undertaken a slower, more measured approach to growth, or even decided to sit with a small, manageable size. Only you can know what size will work best for your business.

5) Pick your team carefully.

Not only are these the people who will be contributing to the overall success of your project, but you may be spending the majority of your waking hours together. You’d better be pretty certain that the individuals you choose possess the skills and positive attitude necessary to keep things going through the inevitable rough patches ahead. You should also like being around one another, and be able to tolerate one another’s particular brand of crazy.

6) Be prepared to scrap your business plan.

What??? You heard me. I can’t tell you how many CEO’s I spoke to who said that once they actually launched their companies, the outcomes were radically different from what they expected. This goes back to the idea of iterating. Ideas look one way on paper, but often play out much differently when tested against actual circumstances. Your business plan will probably function more as a jumping off point than a predictive instrument, so don’t be shocked when you are forced to think on your feet and rework your original plans.

7) Work with mentors.

It really helps to have trusted advisors who can share lessons with you from their own experience. Some of you may be lucky to start out under their tutelage, while others may have to go out and find some more experienced guides to consult for their advice. Be humble, and ask lots of questions. We all have something to learn.

8) Build strong relationships.

Being in business means being part of a community. It will include your industry peers, your investors, your vendors and your clients. From the beginning, it’s essential to build good relationships with people at every step along your path to success. Many have found that social media, in particular Twitter, was a great avenue to find allies and strengthen bonds with them. Depending on your industry, you may find that live interaction is more important than communications via social media. The important thing is to find good partners, and treat them with generosity of spirit and mutual support. You will find that this kind of good karma comes back to you many times over.

9) Just leap in.

Once you’ve done your research, created your plan, consulted your advisors, raised your capital and gathered your team, there’s nothing left to do but close your eyes and jump in. As much careful planning as you do, you don’t really have any idea what will happen until you get started. Don’t overthink, just go ahead and do it. I can’t tell you how many people told me that if they’d known then what they know now, they might never have taken the leap into this business in the first place. Their ignorance/naivete actually served them well. Not one person I spoke to regretted their decision to take the risk on realizing their vision.

It’s clear to me that there is ample opportunity for creating workable and profitable lifestyles way outside the traditional corporate box. Although the internet tech start-up field has gotten quite crowded over the last few years, there is still plenty of room for innovation, even in what have now become tried and true formats. Disruption continues. All. The. Time. Even the disruptors are now being disrupted. In addition, there are many opportunities for success in the non-profit world, as well as the relatively new field of social enterprise, which harnesses the power of profit to support projects that promote social good.

Indeed, these are strange and exciting times. We seem to be at the crossroads of a new era, where old financial power structures are losing their dominance and new business practices are gaining traction, presenting ever increasing opportunities for creativity and imagination to flourish. I salute you, the youngest generation of CEO’s and business adventurers, and look forward to your continued stories of transforming hard work and ingenuity into your own unique tales of success.

Deborah Oster Pannell is a freelance writer & blogger and the founder of Project Mavens, a literary based content creation firm. She is also the former director of communications at She writes her own blog, and is a regular contributor at and She specializes in the arts, innovative & socially responsible businesses and organizations, health & wellness and special events.  Her online portfolio can be found at

About The Author


Matt Wilson is Co-Founder of Under30Experiences, a travel company for young people ages 21-35. He is the original Co-founder of Under30CEO (Acquired 2016). Matt is the Host of the Live Different Podcast and has 50+ Five Star iTunes Ratings on Health, Fitness, Business and Travel. He brings a unique, uncensored approach to his interviews and writing. His work is published on, Forbes, Inc. Magazine, Huffington Post, Reuters, and many others. Matt hosts yoga and fitness retreats in his free time and buys all his food from an organic farm in the jungle of Costa Rica where he lives. He is a shareholder of the Green Bay Packers.

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