Being a founder, entrepreneur, or a business owner can have many exciting and thrilling moments. But it is also punctuated with periods of doubt, slump, and anxiety. So how does one successfully and healthily ride the highs and lows of Entrepreneurship? In this series, called “How To Successfully Ride The Emotional Highs & Lows Of Being An Entrepreneur“ we are talking to successful entrepreneurs who can share stories from their experience. I had the pleasure of interviewing Michael Patrick Carroll.
Michael Patrick Carroll is an experienced entrepreneur, and the Founder and CEO of CARROLL, a nationally recognized leader in the real estate development sector. As a hands-on leader, M. Patrick Carroll led his innovative team to the successful exit of more than 88 properties from the portfolio, resulting in $4.2 billion in sales proceeds. Committed to philanthropy, M. Patrick Carroll actively participates in various charitable endeavors, donating to over 50 charities worldwide.
Thank you so much for joining us in this interview series! Before we dive in, our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’ and how you got started?
What was the “Aha Moment” that led to the idea for your current company? Can you share that story with us?
Michael Patrick Carroll: The “aha moment” that led me to my current company was spurred by one of my biggest accounts when I was in the clothing business. I was always picking the owner’s brain, asking him for advice. One of the things I was struggling with was leaving the clothing business to get into the real estate business. Literally, I was preparing to ask him what his thoughts were about potentially making this jump. He stopped me halfway through and said, “Listen, Patrick, if you don’t get into the real estate business, you’re an idiot.” I respected him as a business leader, so this made the decision a little easier. I was about 23 at the time, so in hindsight, it was a low-risk proposition.
In your opinion, were you a natural born entrepreneur or did you develop that aptitude later on? Can you explain what you mean?
Was there somebody in your life who inspired or helped you to start your journey with your business? Can you share a story with us?
What do you think makes your company stand out? Can you share a story?
Michael Patrick Carroll: I think CARROLL stands out because we’re constantly trying to improve. There’s nothing really about our company that I would consider traditional, stagnant, or status quo. While the real estate business has been in existence for generations, we’re constantly trying to take different approaches. At CARROLL, we’re constantly trying to identify new trends and trying to push the envelope. I believe that even the people we employ are cut from a different cloth. They’re more entrepreneurial in nature and they come to CARROLL because they are entrepreneurial in nature. So, I think that separates our business from a more bureaucratic, institutional type company.
You are a successful business leader. Which three character traits do you think were most instrumental to your success? Can you please share a story or example for each?
Michael Patrick Carroll: One of the three character traits that have been most instrumental in my success is salesmanship. A lot of people have good ideas and good plans. However, if you can’t convince other people to follow you, invest with you, partner with you, and if you can’t really articulate your plan, then your plan is not going to be very fruitful. Salesmanship is definitely something that I think is very important and a character trait of mine that I think has been helpful in my business career tenacity. Not giving up, not just settling for things, and always wanting to improve are also character traits that have helped me in the past, and will hopefully continue to guide me toward success. Finally, I think that general paranoia can be a positive thing. I’m always paranoid, I’m always trying to think about what could go wrong, and the ramifications of things going awry. I think I’ve done a good job at protecting the downside, which leads to that overwhelming fear or paranoia forces you into critical thinking, and making good decisions, that hopefully expand the business.
Often leaders are asked to share the best advice they received. But let’s reverse the question. Can you share a story about advice you’ve received that you now wish you never followed?
Michael Patrick Carroll: I’ve received a lot of good advice. I’ve typically tried to not follow what I would consider “bad advice”. If it didn’t sit well with me when offered, I didn’t follow it. An example would be hiring somebody that looks great on paper, and that comes highly recommended, but something doesn’t click during an in-person interview. If there’s an internal feeling that tells you it’s not the right decision to make, you may sometimes talk yourself out of listening to that internal guidance. That has never ended up well for me and not something I would recommend. I’ve certainly learned how to hone in on those feelings and to trust them. My advice is to listen to your gut, listen to your intuition, ask for opinions. You can trust but should verify.
Which tips would you recommend to your colleagues in your industry to help them create a work culture in which employees thrive and do not “burn out” or get overwhelmed?
What would you advise other business leaders to do in order to build trust, credibility, and Authority in their industry?
Can you help articulate why doing that is essential today?
Michael Patrick Carroll: The world is extremely competitive. It’s probably more competitive today than ever, in history, and it’s because barriers have been broken down. People and companies can shift into industries overnight. You have to constantly be conscious about what you bring to the table. What’s your value proposition? Why are you in the arena you’re in? Why are people doing business with you? You have to constantly be asking those questions. To the extent you’re comfortable with that, you have to be articulate in it. Sales, marketing, and reputation are all part of growing your business. Remaining front and center to customers, clients, investors, and partners, I think that’s all crucial.
What are the most common mistakes you have seen CEOs & founders make when they start a business? What can be done to avoid those errors?
Undoubtedly, a lot of people make mistakes when they start businesses. They may try to move too fast, which is almost always a mistake, or they feel like they need a partner. Sometimes, I see these great ideas with these CEOs, these Founders, and they have multiple Co-Founders. To me, I look at that and hope that the Co-Founder brings a lot to the table because they’ve just reduced their equity by 50% or more. Naturally, I think people take comfort in having a Co-Founder or having a Partner sometimes. Sometimes, that’s a very expensive proposition to make. What can be done to avoid that is simply to surround yourself with people that you trust, incentivize them but don’t be afraid to go it alone. Don’t be afraid to be a Founder. Don’t be afraid to make the tough decisions. That’s the best way to do it.
Ok fantastic. Thank you for those excellent insights, Let’s now shift to the main focus of our interview about How to Successfully Ride The Emotional Highs & Lows Of Being An Entrepreneur. The journey of an entrepreneur is never easy, and is filled with challenges, failures, setbacks, as well as joys, thrills and celebrations. This might be intuitive, but I think it will be very useful to specifically articulate it. Can you describe to our readers why no matter how successful you are as an entrepreneur, you will always have fairly dramatic highs and lows? Particularly, can you help explain why this is different from someone with a “regular job”?
Do you feel comfortable sharing a story from your own experience about how you felt unusually high and excited as a result of your business? We would love to hear it.
Michael Patrick Carroll: Each time that I traveled to New York City and raised capital or completed deals, I felt great. One of the things I would do if I had a successful capital-raising trip was to treat myself. There’s a watch store next door to the hotel I’d stay at called Wempe. I would go in there and frequently, if I had a good trip, I’d buy myself a nice watch. It was an expensive habit, but it was really at a time when I was getting a little bit of burnout. I would do things like that. I would always stay at nice hotels, I would always eat at nice restaurants as a way to reward myself for putting in a lot of the hard work. Now, I look back on that sometimes and say, “Okay, that might have been overkill”. It’s important to reward yourself along the way and to celebrate successes, and to remind yourself, especially when you’ve done a good job, that this is not as easy as it looks, and it should be fun.
Do you feel comfortable sharing a story from your own experience about how you felt unusually low, and vulnerable as a result of your business? We would love to hear it.
Michael Patrick Carroll: The worst feeling in business, and the worst part of running a business, is employee turnover. Sometimes, you’ve had employees for 5–10 years, you’ve grown and it almost becomes like family. When they leave, don’t work out or somehow let you down, that’s always hard. The best part of it, though, is to bounce back from that.
Based on your experience can you tell us what you did to bounce back?
Michael Patrick Carroll: There are always new people searching for an opportunity, there are always new ideas. There are always new people you can bring in, and fresh blood, sometimes, is a good thing. It’s always disappointing when you grow accustomed to working with someone and there’s a transition. That’s probably the hardest part about business, regularly reinventing that type of relationship. The bright side is that I’m always surprised, in a good way, about the quality of people out there that can bring stuff to businesses, that can really come in and add a lot of value on day one. The more you grow your business, the better talent you tend to attract.
Ok super. Here is the main question of our interview. What are your “Five Things You Need To Successfully Ride The Emotional Highs & Lows Of Being An Entrepreneur”? Please share a story or an example for each.
We are living during challenging times and resilience is critical during times like these. How would you define resilience? What do you believe are the characteristics or traits of resilient people?
Did you have any experiences growing up that have contributed to building your resiliency? Would you mind sharing a story?
Michael Patrick Carroll: Taking a non-traditional route after high school graduation has taught me that success can take various avenues. Starting from the bottom has also helped me to build resilience, to recognize that I need to always pick myself up by the proverbial bootstraps, and to depend on myself for my own success. My earlier points about creating a company independently, without Co-Founders and Partners, speak to this point of creating resiliency. When you have to rely on your own skills, leadership, and tenacity to move forward, you learn to be resilient.
In your opinion, do you tend to keep a positive attitude during difficult situations? What helps you to do so?
Michael Patrick Carroll: I certainly attempt to maintain a positive attitude during difficult times. Often, I try to find learning opportunities within those difficulties and to leverage those tough moments into innovation. For example, the COVID-19 pandemic has created a brand new workforce based at home. Thus, in order to meet the evolving demands of this new workforce, we’re committed to offering the amenities that a work-from-home population needs to thrive in this new environment. Together, we’ve adapted to offer solutions to an evolving (and sometimes out of control) situation.
Can you help articulate why a leader’s positive attitude can have a positive impact both on their clients and their team? Please share a story or example if you can.
Michael Patrick Carroll: As a leader, your team members are constantly looking to you for non-verbal queues, responses, and general demeanor, and emulating the energy that you emit throughout the day. Thus, your attitude can largely shape their attitude. The way that you react to something can impact the rest of the team, and set the standards and tone for future situations. That’s something to always keep in mind, as a leader and entrepreneur.
How can our readers further follow you online?
Michael Patrick Carroll: If you’d like to ready further professional musings, please visit my Medium page at
This was very inspiring. Thank you so much for the time you spent with
this. We wish you continued success and good health!