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. Their answers really surprised me…mostly because a common theme among all of their tips was to stress the importance of hiring the right people.

So let's get to their gems of advice!

1) Zachary Johnson - Syndio (August 17)

Speaking of hiring the right people, Zachary Johnson’s business gathers data on this very process. Syndio collects information and data from companies to measure employees and how they interact with each other.

His tip on hiring?

Make sure you’re finding people at the right stage at the right time, and be honest if it’s not working [out with them].
— Zachary Johnson

2) Ravi Bhatt - Branchfire (August 18)

Branchfire designs software to streamline how people work. People across all industries - education, law, film - use their technology to power their productivity.

His tip:

You end up learning that scaling a business doesn’t mean growing a team exponentially. I hired a few more people than I needed to, and that wasn’t the right way for us. Instead of hiring more, it was better to have a few folks who really understood what we were doing.
— Ravi Bhatt

3) Neeraj Berry - Sprig (August 19)

Sprig is a delivery service that brings healthy, fresh and hot meals to your door in select cities under 15 minutes.

His tip:

Surround yourself with people that inspire you and who you can learn from. I have so much fun with people everyday, and I don’t settle when it comes to finding co-founders. Put in the hard work and find people who are gonna do the same.
— Neeraj Berry

4) Dan Willenborg - aptAmigo (August 20)

aptAmigo is a website with detailed rankings and reviews on Chicago neighborhoods and specific inside information on renting and owning property in the city.

His tip:

Delegate. You need help! As the founder, I can’t be the bottleneck for everything. I can’t run every ad campaign. Delegate your weaknesses and assign [yourself] your strengths.
— Dan Willenborg

5) Ryan Coon - Rentalutions (August 21)

Rentalutions provides software for residential landlords to find and keep tenants.

His tip:

Surrounding yourself with people you want to be around is uber important. If you work with people you want to be around, it makes work fun...and it just feels like you’re hanging out building things and making a cool company.
— Ryan Coon

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!