3 Key Traits for Entrepreneurial Success — full interview with early-stage investor Caroline Gash

Meet Caroline Gash, early-stage investor, devout Catholic, and philanthropist

Caroline Gash currently serves as the Managing Director at IrishAngels, one of the largest and most successful angel investing networks in the country. Caroline leads a dynamic team focused on strategic investments in high-performing startups across the U.S. She oversees the full investment process from sourcing, conducting due diligence, and supporting portfolio companies across various industries. 

Before her work in early-stage investments, she held pivotal positions at two boutique private equity firms, one of which she co-founded, including raising $330mm+ across multiple funds investing in energy, real estate, and international gaming. 

Caroline is deeply involved in her community through volunteer work, philanthropy, as well as advising and mentoring emerging founders and fund managers. She earned a B.S. in Science-Business from the University of Notre Dame an M.S. in Finance and an M.B.A. from the University of Denver. 

SENT is thrilled to host Caroline as one of our speakers at the SENT Summit in September. Read on for our full email interview with Caroline to hear her story, get her opinion on what makes a successful entrepreneur, gain insight into how angel investing is a force for good, and more.

Growing Potential > Chasing Success

SENT: How did you get started on your path to investing, and what was the tipping point for your exponential success?

Caroline Gash: My grandmother was a formidable woman. After my grandfather died, leaving her with three small children and no other living blood relatives (her mother and brother had died in a car accident 10 years earlier) she was forced to move from her philanthropic endeavors to developing a career. She was well educated so she became a university professor—in the 1950s! In addition to being a mother and a professional woman, she was a savvy businesswoman and investor. 

As a child, when she would visit us or I’d stay with her, I’d wake up in the morning, run down to her bedroom, and hop on her bed. This was back when the previous day's stock prices were printed in the newspaper and she’d always be sitting on her bed in her pajamas calculating in the margins of the newspaper how much she’d made or lost the previous day. It became a morning ritual for us. We’d discuss the previous day’s stock price movement and what caused them. These conversations evolved into her gifting me stock for Christmas and birthdays, while my cousins all got sweaters and money for slacks. (I’m not sure the difference between slacks and pants but she was always very specific that the money was for slacks!). So, as a pre-teen, I was managing a fairly healthy stock portfolio with my grandmother as my first co-investor, which was truly special. 

Fast forward to high school and college. I’ve always been gifted in mathematics and the sciences. Growing up, especially as a female, the only career that was ever discussed with me for someone who had outsized strengths in math and science was to become a physician. I never even considered anything else (except for that time in kindergarten I told my mom I wanted to be a bus driver so I could ride the bus with all my friends as we lived within walking distance to school and I thought I missed so much social action by not being on the bus in the morning!). While studying for the medical school entrance exam junior year of college, I started questioning if medical school was the right path for me

I had been smart enough as an undergraduate to declare a major at the University of Notre Dame that was pre-medical, but also allowed me to take sophomore-level business courses and some business electives. So, I had some exposure to business, or at least academic business. 

Instead of medical school, I decided to go straight from undergrad to earn an MBA. My thought was that physicians owned practices, and the MBA would help with the largest source of frustration I had from physicians: managing the administrative and business side of their practices. One semester into the MBA, I’d added a Master of Finance, and that reminded me why I loved those mornings with my grandmother so much. Investing is the art and science of understanding human performance. It requires quantitative tools to make sense of and fairly assess all the qualitative aspects of human behavior. It’s highly competitive and results-oriented. That’s what caused me to move into investing.  

After graduating from grad school with two master's degrees in business, I worked as a quantitative analyst, as I had the mathematical chops to build, run, and interpret the complicated algorithms used for trading strategies. I also worked as an equity analyst, putting to use not just my education but the many years of experience I had chatting with my grandmother on summer mornings. I had a skill set that allowed me to do project work, so when I completed a project, I could take a few months off and go to Copenhagen for the summer where my sister was living, or Jakarta for Christmas where my best friend from graduate school hailed from.

When I eventually took a “real” job, a career job instead of a lifestyle job, I landed with a boutique private equity firm in my home city of Denver, Colorado. The firm was unique as the three general partners were serial entrepreneurs and company builders. They’d built and sold a couple of companies together and decided they wanted to be on the other side of the cap table this time. So, they founded a private equity firm. I was their first investment hire. 

I honestly don’t know that I’d ever even heard of entrepreneurship or start-ups before that job. What I learned from them was that I could use my quantitative skills to gather and analyze 100% of the data, but I’d miss the opportunity 100% of the time. They taught me about the hardest part of business: growing it. They gave me responsibilities for which I was woefully unqualified and because my real superpower is that I’m the hardest working, most resilient person in the room, I rose, and then some, to every challenge. Working with them, and with any entrepreneur, is like working in dog years. One year with them is like seven years working with anyone else. I was ignorant enough to be fearless. I was successful enough in other areas of my life—academically, socially, philanthropically—to be confident. And, I was grateful enough for the opportunities that I excelled at because I was focused on learning and growing my own potential, not generating exponential success. 

Keys to Entrepreneurial Success

SENT: As a long-time investor, what do you see as critical characteristics for a founder or entrepreneur to succeed?

Caroline Gash: Only three things: A certain level of intelligence, world-class grit, and some luck. 

When I speak of intelligence, I don’t mean academic success or how one scores on tests. I mean the ability to figure out what you know, what you don’t know, what matters, and how to reduce your risk. Founders, by definition, are under-resourced. Their ability to succeed hinges on their ability to figure out how to get more out of less. They do this through a lot of different strategies. They tend to be brilliant listeners as they’re endlessly calculating people’s motivations, whether to understand their customer’s pain points or figure out how to entice a heavy hitter to work with them. They typically have high self-awareness, and while they tend to be utility players who can do a lot of things at a high level, they understand how to build a winning team based on the unique skill sets each person brings to the overall mission. They know how to learn, how to assess needs, how to recruit, and how to inspire. 

When I speak of grit, I mean the ability to keep going, be resilient, and be determined with a single goal in mind. To face adversity and persevere not because you should but because the conviction to achieve the goal is stronger than the need to feel secure. The best entrepreneurs turn major setbacks into minor ones because they know that founding a company is an ultra-marathon, not a sprint. They conserve their energy for only the things that really matter. It takes a lot of energy to constantly switch between strategy and tactics, sales and operations, leader and listener. Coupled with the intelligence I also spoke about previously, they know when to quit (opportunity cost is the highest one of all!) and when to push their own boundaries even further. It’s that almost innate need to push boundaries to achieve something most others wouldn’t even attempt, that makes an entrepreneur an entrepreneur. 

Finally, it takes luck. The one out of the three we have no control over. We don’t determine where lightning strikes, but with some intelligence and some grit, we can place ourselves in as close proximity as possible to where lightning is known to strike. The best founders figure out what they can do to increase their chances of catching that lightning in a bottle. 

Community Amplifies Achievements

SENT: How has joining Irish Angels changed your professional life?

Caroline Gash: Joining IrishAngels as the Managing Director introduced me to the inspirational community of early-stage investors and founders who are shaping the future. At its best, it’s an ecosystem of doers working on the largest problems facing our generation and beyond. At the center of that ecosystem are founders who refuse to wait for someone else to solve the challenges they see and know. The founders dare to continuously move forward in ruthless pursuit of audacious goals, and the investors dare to take the high financial risks associated with investing in leading-edge technology. These are my colleagues; they shape not only my professional but also my personal life, daily. It is this community that dares to build legacies that will far outlast any one of us. 

SENT: Why is community so critical for the successful development of founders at large and in Irish Angels, a group comprised of Notre Dame alumni?

Caroline Gash: Entrepreneurship, like life, is too hard to do alone. And, just like life, experiences and achievements are amplified when done with the support of others. When working in a community, there is shared risk but also shared synergies. 

With regards to what community means to IrishAngels, an organization comprised of Notre Dame alumni, Oxford defines community as, “a feeling of fellowship with others, as a result of sharing common attitudes, interests, and goals.” Community requires a commitment to something bigger than yourself. At the University of Notre Dame, we talk about “God, Country, Notre Dame” when referring to the importance of Notre Dame in our lives. God first. country second. Notre Dame third. It speaks to the passion we have for the place, our shared experience, and one another. It’s a commitment we make to champion our ideals and one another. As Notre Dame alumni, we have a joke, “How do you know within five minutes of meeting someone if they’re a Notre Dame grad or not? They’ll tell you!” The Notre Dame family is so core to who we are, how we want to present ourselves to the world, and what we want to share with it, that we do within minutes of meeting someone! 

For IrishAngels, we share this relentless community-building and connection-making with our founders. We bring them into the Notre Dame family and commit to them with the same passion and gusto, both professionally and personally, as we do for our fellow Notre Dame alumni. 

Private Equity, VC, and Angels Investing as Catalysts for Good

SENT: How can private equity be a force for good?

Caroline Gash: Private equity, venture capital, angel investing—they’re all catalyzers. Money isn’t enough to ensure success, not by a long shot, but it is a necessity. That money can be used to do many things, but in the investing world, we use it to make more money. It’s an enlightened and long-term view to believe that the most sustainable way to ensure the highest returns is to do so through improving the lives of those impacted by the business.

Two concrete examples:

The first is Chime – We were early investors in the neobank Chime. Now a unicorn, a company valued at more than $1 billion, Chime has around 14.5 million customers. For those millions of customers, Chime does not charge overdraft fees, monthly service fees, nor does it require monthly minimums. Chime ushered in a new era of fintech companies committed to profiting with customers, not off of customers. It has allowed customers to keep more of their paychecks and democratized banking services.

The second is Hallow – We were early investors in the Catholic prayer app Hallow. Hallow has become the #1 Catholic app in the world, has been downloaded 14 million times, and has assisted in 400 million prayers across 150+ countries. It has helped me, personally, lead rosaries in environments where I don’t know if I could have done so otherwise, bringing me closer to my faith and community.

Hello Dolly is one of my all-time favorite musicals. A perfect though ineloquent quote (it was said by Barbara Streisand who played Dolly in the movie adaptation, so I feel like I’m in strong enough company to say it here), “Money, pardon the expression, is like manure. It’s not worth a thing unless it’s spread around encouraging young things to grow.” 

The best way to encourage innovation and ideation is to create a business model that allows the product or service to self-sustain by making a profit. 

Learning to Lead as a Catholic

SENT: Throughout this journey, what’s your favorite thing you’ve learned about designing your life intentionally as a Catholic business leader?

Caroline Gash: I’ve learned that stepping into my career as authentically and intentionally Catholic creates a pull rather than a push. I’d been taught to keep religion out of business, so I spent the first part of my career not referencing it, not talking about it, and not comfortably allowing it to be openly shared with my colleagues. Interestingly, that changed when I hired a colleague who is an Orthodox Jew. He was so comfortable with being Jewish first in the business setting that I was in awe. We spoke openly about our beliefs and how they guide us. It’s funny that my Jewish colleague helped me find the confidence to be intentionally Catholic in my own career, but sometimes these lessons come from the place you’re least looking.

Being around people who have principles, who have conviction, who have a sense of working for something bigger than themselves is magnetic. It is those leaders who build lasting communities, and those lasting communities that change the trajectory of humanity.

Want to hear more from Caroline? Register for the SENT Summit!

Attend the SENT Summit: Build Like the Saints this September! Join 400+ Catholic entrepreneurs and executives paving the way to transform society through new initiatives, guided firmly by Catholic principles, and supported by community. Hear from the foremost leaders and gain the inspiration and insight necessary to drive your growth and the growth of your company.