Community//

“Don’t perfect your prototype, progress is more important than perfection” With Phil Castro CEO of BarPass

“Progress over perfection” — One of the biggest rookie mistakes is trying to perfect your prototype. In the end, the market always tells you if your product/service is valuable or not. With that being said, a founder should just focus on getting an MVP (minimal viable product) out to understand if there is a need in the […]


“Progress over perfection” — One of the biggest rookie mistakes is trying to perfect your prototype. In the end, the market always tells you if your product/service is valuable or not. With that being said, a founder should just focus on getting an MVP (minimal viable product) out to understand if there is a need in the market for that particular product or service. Worry about adding all of the bells and whistles after you are past the proof of concept. I had a problem doing this at first from being a perfectionist, but you quickly learn that market feedback trumps product perfection.


I had the pleasure of interviewing Phil Castro who is the CEO/Founder of BarPass. BarPass is a digital bar promotion platform that allows after-work professionals to receive exclusive deals (typically one complimentary cocktail at each event) at the trendiest bars and restaurants. Bar owners love BarPass since it fills up their slower time frames and users love BarPass since it’s a great way to discover bars, meet people and taste spirits. Phil can best be described as a serial entrepreneur and a startup veteran from Chicago. In the past 10 years of his career, Phil has started multiple successful companies of his own as well as worked for multiple venture backed startups under the Lightbank umbrella. He has won awards like “35 Under 35”, “Startup of the Year”, “Most Innovative Entrepreneur” and more. Along with winning such prestigious awards, he has also been on dozes of media outlets like TastyTrade, BuiltIn, Inc Magazine, Crain’s, ABC, Voyage, WGN, etc. Lastly, Mr. Castro also gives back to the new wave of entrepreneurs by providing a 1 day crash course in early stage entrepreneurship, startups and venture capital. You can register for his 10 hour workshops held in different cities around the nation by checking out www.StartupBootkamp.com.


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

My pleasure! Well, I started throwing events at my college bar to make some extra cash during my 4 year stay at WIU. Unfortunately, the economy tanked right as I graduated and I knew I had to do something to make ends meet. That is when I officially started my first company in promotions and event planning in the Chicago area, due to my recent college experiences. One year later, I was approached by one of the biggest Midwest VC firms that wanted me to work for a new nightlife portfolio company they recently founded. This particular startup was actually mocking their sister portfolio company Groupon (which was also a fairly new startup at the time) but in the nightlife industry. So during the day, I would gain these invaluable experiences being in the startup ecosystem and at night I would run my own company on the side. Having both sides of experience has truly molded my career and paved the way for decades to come.

Can you share the most interesting story that happened to you since you started your company?

The most interesting time was when I had to host the greatest athlete on earth, Michael Jordan. In my career I had to host dozens of celebrities and athletes but I was only star struck once and it was with my all time NBA idol from the windy city. I was mostly speechless for the first half hour but after a few cocktails I was able to speak like a normal human being again, thankfully.

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?

Believing everything would run as smooth as I envisioned. The truth is that starting a business is one of the toughest things you will ever do. I unequivocally learned the final destination doesn’t change but the route to get there often must.

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

Happy hours were banned in most states for the past 30 years. Not many people know this information, but they had some strict laws in place prohibiting actual happy hours (happy hour: an alcohol price fluctuation between a certain time period at a bar/restaurant) to take place. Recently in late 2015, many of the states started amended these laws and allowed happy hours to commence again. I got wind of this and shut down my last startup in order to start BarPass almost immediately. So, I am the first mover to market with a company solely focused on happy hour promotions. I assume there will be pop up competitors soon, but that doesn’t really bother me too much.

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

Startups are nearly impossible to execute and only the strong survive. Execution plays the biggest part in success, but one must have a clear mind in order to execute on a daily basis. While building your startup seems like life within itself, your mental and physical health should always come first! So I very much recommend clearing your mind with any healthy activities (gym, yoga, walks, reading, etc.) that you should prefer on a weekly basis. Your clarity and healthiness will help your startup flourish, I promise you.

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 parents. Although they never showered me with materialistic things growing up, they did in fact provide me with everything that is important in life: like morals, discipline, manners, education, etc. I was born on the south side of Chicago but always wanted to move to the downtown area as a kid because of the “cool” buildings (I was easily amused) and business professionals. My parent’s would tell me to work hard while being a good person and anything would be obtainable in life. Along with parents, I must include my wife as well for always being by my side and allowing me to live this roller-coaster entrepreneurial lifestyle. I owe all of my success to them and not a day goes by that I am not grateful for the sacrifices they have made.

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

In the beginning of my career, I did have a few mentors that have helped me persevere through the dark times of entrepreneurship. Being a startup founder is often glorified by the media and honestly that is far from the truth most of the time. I always remembered these times of need and have made a conscious effort to give back to founders or beginning stage entrepreneurs (thus my traveling entrepreneurial workshop Startup Bootkamp). I believe they call this concept “paying it forward.”

Do you have a favorite “Life Lesson Quote”? Can you share a story of how that was relevant to you in your life?

“It’s more important to learn and fail than it is to always be right.” Failing is inevitable and is unfortunately often associated with shame or other negative connotations. I believe learning from mistakes makes one ten times stronger than any successful venture. I’ve lost a lot of money and time with previous startups, which I used to deem as a tragedy; I now deem them as a blessing since I am ten times smarter and have learned invaluable lessons. If you are smart, you never lose; you either win or you learn.

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

1. “Startups are hard” — Everyone knows the statistics that most startups fail, but you don’t really understand why until you launch your own. You truly have to juggle a million things on a weekly basis, make great decisions in a timely manner, be ferocious everyday and outsmart your competitors. Easier said than done, right? There is no handbook for startups and you get reminded of this (like I often did) throughout your career.

2. “Entrepreneurship isn’t what it seems” — You will be down in the dumps one day and on top of the world the next. It is truly an emotional roller coaster and takes a toll on your body. I recall one day I was featured in a huge magazine, but also lost my #1 client all in the same day. When your baby (your startup) goes through something similar, it really messes with your emotions in a very confusing way. As I mentioned, the media glorifies entrepreneurship and I think a lot of the younger generation just witnesses the big wins and assumes that it’s easily obtainable or event probable. The truth is that you should buckle up because you are in for one bumpy ride!

3. “Timing is everything” — Even the best ideas fail because of bad timing. This could be due to laws in place, technology barriers, the comfort zones of the market or just being too early/late to the party. The last startup I founded, we wanted to connect to the users’ bank account and it was way too early for that in 2014. So we had to adapt and edit the concept of collecting payments to match the comfort level to the current market. Now the market uses these payment methods everyday!

4. “Progress over perfection” — One of the biggest rookie mistakes is trying to perfect your prototype. In the end, the market always tells you if your product/service is valuable or not. With that being said, a founder should just focus on getting an MVP (minimal viable product) out to understand if there is a need in the market for that particular product or service. Worry about adding all of the bells and whistles after you are past the proof of concept. I had a problem doing this at first from being a perfectionist, but you quickly learn that market feedback trumps product perfection.

5. “Understand the VC game” — I can come up with multiple analogies for raising venture capital funds; it’s like a game of chess, it’s like dating, etc. It truly is a game and every founder should play it extremely well to have a fair shot of getting funded (if that is the route they wish to take). Ideally, you can self-fund yourself with profits, but this is usually not the case for multiple reasons. So when you do go out to raise capital, understand the mindsets of venture capitalists before taking any meetings with them, speak their lingo, know your numbers and understand their investment strategy. I made the mistake in wasting countless hours and meetings with VC’s who didn’t even have the proper funds (due to them being at the end of their fund life) or their portfolios didn’t match my industry very well.

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. 🙂

I would form an entrepreneurial program that serves underprivileged teenagers in urban areas. Most of these kids do not have access to this form of education or resources within their neighborhoods. So, I would be providing them with consistent content and unconventional education that will help them understand they are capable of starting companies too; despite any cultural or economic backgrounds.

How can our readers follow you on social media?

Instagram: @ThePhilCastro

Twitter: @Phil_Castro

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

The Thrive Global Community welcomes voices from many spheres. We publish pieces written by outside contributors with a wide range of opinions, which don’t necessarily reflect our own. Learn more or join us as a community member!
Share your comments below. Please read our commenting guidelines before posting. If you have a concern about a comment, report it here.

You might also like...

Community//

“Lean Is Important” 5 Startup Strategies With Ziko Atamuloev

by Yitzi Weiner
Community//

“With Multidimensional Economics, I have started a movement that will bring the most amount of good to the most amount of people” With Doug Howarth

by Yitzi Weiner
Community//

“Fintech Is Nurturing A New Generation Of Innovators Focused On Setting a Higher Standard For UX/UI” with CEO Phil Barrar

by Breana Patel

Sign up for the Thrive Global newsletter

Will be used in accordance with our privacy policy.

Thrive Global
People look for retreats for themselves, in the country, by the coast, or in the hills . . . There is nowhere that a person can find a more peaceful and trouble-free retreat than in his own mind. . . . So constantly give yourself this retreat, and renew yourself.

- MARCUS AURELIUS

We use cookies on our site to give you the best experience possible. By continuing to browse the site, you agree to this use. For more information on how we use cookies, see our Privacy Policy.