“A win today is a win for today. Tomorrow is a new day and you need to win tomorrow, too.” with Robert Brill and Chaya Weiner

There’s a constant need to bet on yourself. The truth is that betting on yourself doesn’t go away with success, it continues on with greater risk every time you “level up”. There is no time for complacency. A win today is a win for today. Tomorrow is a new day and you need to win […]

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There’s a constant need to bet on yourself. The truth is that betting on yourself doesn’t go away with success, it continues on with greater risk every time you “level up”. There is no time for complacency. A win today is a win for today. Tomorrow is a new day and you need to win tomorrow, too.

As part of my series about the leadership lessons of accomplished business leaders, I had the pleasure of interviewing Robert Brill, the CEO and Founder of, a hyperlocal advertising company. With 16 years of experience in the digital advertising business, Robert leads his team of media buyers to help agencies and advertisers tackle complex business challenges.

Thank you so much for joining us! Can you tell us a story about what brought you to this specific career path?

I had three goals out of college: I wanted my work to be seen and noticed. I wanted to work in a fun environment. I wanted to make my parents proud.

Two weeks after graduating, I got my first agency job at Universal McCann. I had a great boss in Elias Plishner and found that I love the ad business.

After 10 years of working in advertising, I saw a golden moment to start my own company. I realized there is a need for digital advertising to make its way to small and midsize advertisers and with that I created

Fast forward to 2019, I have an incredible team of 10, happy clients across the USA, and mid-seven-digit sales revenue.

Can you share your story of Grit and Success? First can you tell us a story about the hard times that you faced when you first started your journey?

Achieving success might sound simple with the lens of hindsight, but it took two years to establish momentum for my dream. I originally started as a consulting firm. At the same time, I also developed a social ad platform, an influencer marketing venture, and an Instagram business. All of these separate elements turned out to be distractions from one of the things I do best — ad buying.

Once I found focus for my business and defined exactly how to talk about the work we do, I hit the ground running with newfound enthusiasm. I spoke to hundreds of people at conferences and events, and used that market research to understand the key phrases that resonated with clients. That’s how we came to focus on hyperlocal advertising.

Where did you get the drive to continue even though things were so hard?

There weren’t any other opportunities that excited me the way my vision for did. I knew there was a need in the marketplace and that I was able to provide answers and valuable answers problem solving services. Luckily, I found great business partners to connect with and develop pipelines with. My drive came from the belief that there wasn’t a better option on the horizon; I had to push forward with the progress I was making.

So, how are things going today? How did Grit lead to your eventual success? has evolved in fantastic ways. Clients return year after year. Our team is growing. In the face of changes and challenges, we have developed important processes that make our team stronger and operations more refined, which makes our clients willing to place greater trust in our company.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

As a passion project I wanted to become an influencer and created a food photo account called Dudeletseat. It gained some traction. Dudeletseat allowed me to attend special events, enjoy free meals, and generate minimal revenue. I learned that the world of influencer marketing is so different from programmatic ad buying.

I also realized that deviating from what I know best and trying a new endeavor cost me energy that I could have spent developing my ad buying business. I still keep Dudeletseat live on Instagram and Facebook as a creative outlet — everyone needs a hobby — and inspiration for good places to eat.

What do you think makes your company stand out? Can you share a story?

The key goal for us is to eliminate the complexities of digital ad buying for our clients. offers the best data, algorithmic optimization, and platform targeting to our clients who normally would not have access to these capabilities. When we work with agencies, we take on their processes and become an extension of their teams.

We work with agencies who specialize in a variety of different campaign types, from digital out of home, to ticket sales, lead generation, and CPG sales. While we have one process internally within our org, we adapt our process to meet the needs of our clients. Our mission is power disparate ad buying groups for agencies across the US.

Which tips would you recommend to your colleagues in your industry to help them to thrive and not “burn out”?

Three tips: mindset, exercise, and disconnection.

Mindset is critical as it helps frame all circumstances. Bad situations become tolerable with context. Great situations become launching boards with context.

Exercising is key for me because it provides a way to raise endorphins in the morning and burn off some of the stress.

Finally, I try to disconnect one day a weekend. If I feel maxed-out, I’ll spring for a vacation.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story?

My wife Nicole is this person. While many people supported me as I started the business, she was the one who gave me the most consistent and valuable advice as we were dealing with various stages of growth — from the “where are our clients” phase to the “holy cow we need to hire” phase.

She is a talented advisor and the single person I go to regularly who gives me amazing points of view that have direct impact on our business.

How have you used your success to bring goodness to the world?

Yes, I hope so. I think this is happening in two ways. First, for our small business clients, we provide a venue to build business that would otherwise be hard to access outside of The second way is that we work on great campaigns that have a positive impact on people’s wellbeing and health.

What are your “5 things I wish someone told me before I started leading my company” and why. Please share a story or example for each.

1. Choosing a life partner is choosing a business partner. Getting married was the best thing I ever did (up to having our first baby Henry Alexander)! I should have done it sooner because having my wife as my trusted partner is so incredible and I’m so much more focused on the important things.

2. You’ll probably have to hire people before you feel like you’re ready. Hiring people is great, but it’s also a risk. If you’re questioning it, it’s probably time to hire.

3. There’s a constant need to bet on yourself. The truth is that betting on yourself doesn’t go away with success, it continues on with greater risk every time you “level up”.

4. There is no time for complacency. A win today is a win for today. Tomorrow is a new day and you need to win tomorrow, too.

5. Stick to what you are good at. My time learning influencer marketing was good, but it’s likely that that time could have yielded better results doing programmatic ad buying.

6. Your boss (aka yourself) will work you harder than any boss has ever worked you. I work harder for myself than I ever have before.

You are a person of great influence. If you could start a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

Life is short. Celebrate it, and the people you love, every chance you get.

How can our readers follow you on social media?

This was very inspiring. Thank you so much for joining us!

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