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How to Succeed in Business | Lessons from CEOs from OnSecondThought, Chicagoland Skydiving Center, Visible and Modest

Aug 28, 2015

By: Jenna DiMaria

Bootstrapping in America is a daily segment that we air on the tastytrade network. Tom and Tony talk to business leaders in Chicago and beyond, who share information about their product, why they created it, as well as general insights on starting a business and being an entrepreneur.

This week, after each of the bootstrappers wrapped their segment with Tom and Tony, we grabbed a moment of their time to ask what valuable lessons they’ve learned in business that would be valuable to entrepreneurs. While we got a lot of great answers, they all talked about the importance of focusing - whether that's on a business or on yourself or your team.

1) Maci Petersen - On Second Thought (August 24)

With On Second Thought, you can undo your texts before you send them. All you have to do is swipe your message left or right within moments after hitting "Send."

Her thoughts on gaining focus:

I pray and meditiate. It helps me keep my perspective.
— Maci Petersen

2) Doug Smith - Chicagoland Skydiving Center (August 25)

Doug Smith is the President/CEO at Chicagoland Skydiving Center. The Chicagoland Skydiving Center was opened in 2000 in Rochelle, Illinois.  It now is one of the premier centers in the U.S.

How does he say he would've focused his time?

Financing. I shied away from investors. I’ve always wanted to do this on my own, but if I could do it over, I definitely would’ve used other people’s money.
— Doug Smith

3)  Mike Preuss - (August 26)

Mike Preuss is the CEO & Co-founder of was launched in the winter of 2013 with a very clear mandate – to simplify the sharing, management, and reporting of data between startups and investors. 

His focus was on how to treat other people.

Be a good person. Treat your employees, partners, customers all the same. No one likes to work with dicks.
— Mike Preuss

4) Harper Reed - Modest (August 27)

Modest is a mobile commerce platform designed to allow customers to buy products with just a click of a button. The company is only two years old and was just acquired by PayPal for an undisclosed price.

His focus is on the importance of treating yourself well and your team.

Get sleep. Take care of yourself so you can do your best work. And take care of the people around you.
— Harper Reed

Are you an entrepreneur? What are your tips for hiring people? Watch all our Bootstrapping in America segments here and learn more about their entrepreneurial journeys. If you’ve got a story about starting a business, we wanna hear it. Get in touch with us at!

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