The Power of Uncomfortable Conversations, According to Marketing Powerhouse Jenne Lombardo The Make It Awards judge and marketing genius has some inside tips to inspire and fire entrepreneurs up.

By Dan Bova

Jenne Lombardo

Could you use $30,000 to launch or grow your business? Yeah, we thought so, which is why we wanted to share application information for the second-annual Make It Awards, a program sponsored by the New York Knicks and Squarespace that will award four entrepreneurs with $30,000, publicity and guidance to help take their businesses to the next level. Interested? Apply here before the December 14 deadline.

As applications roll in, Entrepreneur spoke with one of the judges, Jenne Lombardo, co-founder of MADE Fashion Week and founder of The Terminal Presents, about what she is looking for from contestants, and any advice she has for aspiring entrepreneurs. Lombardo has been called a "pint-size branding genius" by T Magazine, so pay attention here, folks.

Why was it important for you to be part of the Make It Awards?

When I was younger there were not too many organizations that supported entrepreneurs. In fact, I am not even sure the entrepreneurial spirit was supported in its entirety. I think we were considered "loose cannons" in the corporate world. At the time it was conflicting, because here I was having out of the box/bigger picture ideas but being reprimanded for thinking differently and not like everyone else. The New York Knicks and Squarespace supporting entrepreneurs and providing access to a platform like the Make It Awards is such a gift for burgeoning businesses that have the spirit and drive to "make it," but not necessarily the means and access. To be in a position to encourage this talent to make their mark and do something different is an honor for me.

Related: Pitching Your Business to a Journalist? Here's What Works.

What would you have done with a $30K prize when you were just starting out?

It would have created a clear financial roadmap that would allow me to prioritize expenses instead of being reactionary. I would cut through all the clutter and determine what the absolute necessities are to get a company off the ground. I would also ensure that I locked in the best business partner to help me achieve our goals -- I work better as a team as opposed to alone.

Last year's Make It Awards winners, image credit: MSG

What do you look for in a company or founder that you are considering investing your time, effort and money in?

Passion, persistence and vision. Someone that eats, lives and breathes their concept. Talent is up there, too, but a lot of people have talent. It's the ones who can execute and get past the "I have a great idea" stage who are the most interesting to me. Also, it's important to be confident and know your business and the competitive landscape -- but don't confuse confidence with arrogance.

What are the three most common mistakes you see people/companies make in marketing?

1. Not having a clear sense of identity. Know who you are and who you are not and stay in that lane. You cannot be everything to everyone.

2. Not connecting with customers in a truly authentic and meaningful way. Without customers, you don't have a company. Honoring them, engaging with them and incentivizing them is paramount.

3. Not spending marketing dollars. This day and age you have to pay to play. I am not saying spend without a clear understanding of how to measure success, but consider dollar allocations toward online ads, events, collaborations, influencer marketing, gifting, etc.

Related: His Parents Loaned Him $30,000 to Start a Company. Now It's Valued at $1.7 Billion.

Describe your leadership style.

I work with my team, I learn from them, include them in crucial decision-making processes and ask them questions. I hired them for a reason -- because I don't know everything and rely heavily on their areas of expertise. I try to lead by example and not govern with fear. When you act as a team everyone is more motivated and encouraged to take ownership of their projects.

Are there any quotes or sayings that you draw inspiration from?

One I have been thinking about a lot lately is, "A person's success in life can usually be measured by the number of uncomfortable conversations a person is willing to have." I wish I had more uncomfortable conversations with people personally and professionally during my younger years. It is important to establish your voice and not be afraid to use it. You will earn more respect from people, but most importantly you will walk away having respect for yourself.

Relate: 8 Financial Tips for Entrepreneurs Launching a Startup

Have you seen the role of women in business change since you started out? How so?

Absolutely -- I have first-hand got to experience this shift. Let me preface this by saying there is still a long way to go, but the most important change I see is the camaraderie and the support fellow female business leaders are offering to each other. We realized that if we don't support each other first and foremost no one else will.

Please give us a playlist guaranteed to get people motivated to kick some ass during their day.

"WIN" -- Jay Rock

"Never Recover" -- Lil Baby & Gunna, Drake

Not All Heroes Wear Capes -- Metro Boomin

"Sicko Mode" -- Travis Scott

"In My House" - Little Dragon

Wavy Line
Dan Bova

Entrepreneur Staff

VP of Special Projects

Dan Bova is the VP of Special Projects at He previously worked at Jimmy Kimmel Live, Maxim and Spy magazine. Check out his latest humor books for kids, including Wendell the Werewolf, Road & Track Crew's Big & Fast Cars, and The Big Little Book of Awesome Stuff.

Editor's Pick

'Catastrophic': Here's What You Should Know About the Debt Ceiling Crisis — And How a Default Could Impact Your Business
I Helped Grow 4 Unicorns Over 10 Years That Generated $18 Billion in Online Revenues. Here's What I've Learned.
Want to Break Bad Habits and Supercharge Your Business? Use This Technique.
Don't Have Any Clients But Need Customer Testimonials? Follow These 3 Tricks To Boost Your Rep.
Why Are Some Wines More Expensive Than Others? A Top Winemaker Gives a Full-Bodied Explanation.

Related Topics

Business News

'All Hell Is Going to Break Loose': Barbara Corcoran Issues Warning About Real Estate Market, Interest Rates

The "Shark Tank" star appeared on FOX Business' "The Clayman Countdown" this week.

Money & Finance

3 Ways to Create Multiple (Big) Streams of Income

Here are three ways to create multiple streams of income. These strategies require effort and resources but offer significant financial potential.


The Real Reason Why The Return to Office Movement is Failing is Revealed in New Study

There is a vivid sign of the disconnect between employees and their workplace, a glaring indication that companies need to revise their scripts to improve their hybrid and remote work policies.

Business News

An NFL Coach Saved a 3-Year-Old Boy From Drowning in a Hotel Pool. 'I'm Thankful I Knew What To Do.'

Los Angeles Rams defensive coordinator Raheem Morris was at the right place at the right time — with the right knowledge.

Science & Technology

She's Been Coding Since Age 7 and Presented Her Life-Saving App to Tim Cook Last Year. Now 17, She's on Track to Solve Even Bigger Problems.

Angelina Tsuboi, a full-stack mobile and web developer who also happens to be a pilot, has always been solution-oriented.

Business News

7 of the 10 Most Expensive Cities to Live in the U.S. Are in One State

A new report by U.S. News found that San Diego is the most expensive city to live in for 2023-2024, followed by Los Angeles. New York City didn't even rank in the top 10.