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Patrick Shanahan of DaySmart: “Be patient”

Be patient. Leaders must be able to make decisions but avoid reacting too quickly. This balance comes with maturity. As a young professional, your emotions are more likely to get the best of you. However, if you can be patient — without being paralyzed — you can still push the envelope and drive the company forward. The COVID19 pandemic has […]

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Be patient. Leaders must be able to make decisions but avoid reacting too quickly. This balance comes with maturity. As a young professional, your emotions are more likely to get the best of you. However, if you can be patient — without being paralyzed — you can still push the envelope and drive the company forward.


The COVID19 pandemic has disrupted all of our lives. But sometimes disruptions can be times of opportunity. Many people’s livelihoods have been hurt by the pandemic. But some saw this as an opportune time to take their lives in a new direction.

As a part of this series called “How I Was Able To Pivot To A New Exciting Opportunity Because Of The Pandemic”, I had the pleasure of interviewing Patrick Shanahan.

Patrick Shanahan is CEO at DaySmart, a provider of business management software empowering entrepreneurs to operate and grow their businesses. Patrick is an expert in the payments and FinTech space and served as COO at CardConnect prior to DaySmart.


Thank you so much for doing this with us! Before we start, our readers would love to “get to know you” a bit better. Can you tell us a bit about your childhood backstory?

I am the youngest of five boys — that’s the most important thing to know about my childhood. Together, my brothers and I started a family business. My brother Brian, who is 14 years older than me, was a serial entrepreneur in the payments space. He built and sold a couple companies, and most recently started CardConnect in 2006. I joined in 2008, when I was 23 years old, as did my brother Jeff.

Over the years, CardConnect grew both organically and through acquisition. In 2010, we took a private equity investment and continued acquiring smaller payment companies. In 2012, CardConnect pivoted to the technology side of the business and built out the payment processing platform that DaySmart uses today. Shortly thereafter, in 2013, Brian left the business, Jeff became CEO and I became COO. We took the company public in 2016 and sold it in 2017.

Building a business with your bothers is a unique experience. The highs are high, and the lows are low –fortunately, as the youngest brother, I got to learn a lot because we saw success early in my career.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

Don’t be afraid to make decisions.” When you’re growing a business, people often get paralyzed by the decision-making process. My brothers all shared the mindset that good businesses make decisions, and more often than not, they end up being right.

Is there a particular book, podcast, or film that made a significant impact on you? Can you share a story or explain why it resonated with you so much?

I have to recommend 10% Happier: How I Tamed the Voice in my Head by Dan Harris. With how fast the world moves, from cell phones to email, mindfulness can bring you back to the current moment. It’s easy to constantly move on to the next thing; it’s much harder to listen and be patient and present. At CardConnect, we organized mindfulness classes and even held a retreat where the group didn’t speak for seven hours. It was difficult, but there are clear benefits, personally and professionally.

Let’s now shift to the main part of our discussion. Can you tell our readers about your career experience before the Pandemic began?

Because I’m the youngest of five boys, I am naturally competitive — which can be both positive and negative — never satisfied and always striving to do better. Throughout my entire career, I have always tried to challenge the status quo. Becoming a COO at 26 years old, I was given a lot of responsibility at a young age. It required me to mature faster, catch up with the older professionals I was surrounded by and aspire to do more. This track contributed to who I am today and how I’ve grown over the years.

What did you do to pivot as a result of the Pandemic?

When COVID-19 hit, DaySmart’s business quickly reacted to the evolving needs of its small business customers, which were affected disproportionately by the pandemic. Knowing our customers had to change the way they operated their businesses, DaySmart pivoted its product roadmap to release features our customers needed. For instance, we developed better telecommunications tools to help small businesses engage with their clientele in times of uncertainty, especially during state-mandated closures. Ultimately, we adapted and grew in a difficult environment, empowering our customers to do the same.

Can you tell us about the specific “Aha moment” that gave you the idea to start this new path?

The solutions that DaySmart provides are critical for our customers to operate and grow their businesses. Now more than ever, software is needed for small businesses to succeed — from managing their customer base to working more efficiently. DaySmart lays this foundation as it’s required to survive and thrive in high-growth, rapidly changing markets. This capability and mission resonated with me, and I saw the opportunity to grow the payments side of the business and enable customers even further.

How are things going with this new initiative?

When building technology and feature functionality, nothing gets done overnight. That said, many features in Q1 and Q2 will provide ample value-add to our customers, helping them operate their businesses more efficiently. Simultaneously, DaySmart is continuing to grow from an M&A perspective. We are identifying every opportunity to become even more competitive.

Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

My brother Jeff, the CEO of CardConnect, and I have been attached at the hip since childhood. Not only did he provide me with several opportunities, but we grew in business together. We moved from Pittsburg to Cleveland, where CardConnect was originally headquartered, with just 15 employees. He was also young when building CardConnect, so I appreciate looking back on both of our journeys, from where we started to how far we’ve come.

Can you share the most interesting story that happened to you since you started in this new direction?

Since joining DaySmart as CEO, we have acquired two companies virtually. I’ve never been faced with this opportunity, or challenge, before — especially not before the pandemic — but accomplished two virtual acquisitions within 40 days.

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

While I’ve accrued ample experience as a leader over the years, there are a few things I wish I knew in the beginning of my career:

  1. Listen more than you speak. All great leaders listen. It’s a Catch 22 — as a leader, you’re expected to speak, but you really need to hear and understand your teams, customers and partners.
  2. Be patient. Leaders must be able to make decisions but avoid reacting too quickly. This balance comes with maturity. As a young professional, your emotions are more likely to get the best of you. However, if you can be patient — without being paralyzed — you can still push the envelope and drive the company forward.
  3. Trust your people. As a leader, it’s likely that you take on too much. You must trust everyone in your company and management team. Delegation is key!
  4. Don’t take yourself too seriously. Businesspeople need to check their egos are the door. We aren’t solving the world’s problems, like doctors — we’re helping businesses operate more efficiently. It’s okay to be self-deprecating. Work hard and have fun — play golf!
  5. Keep things simple. If businesses prioritize simplicity, they can make decisions quickly. Don’t overcomplicate things — understand where you’re going and create tangible milestones to get there.

So many of us have become anxious from the dramatic jolts of the news cycle. Can you share the strategies that you have used to optimize your mental wellness during this stressful period?

To maintain my mental wellness, I pay less attention to the news than I normally would. Early on, I was engulfed in the 24/7 cycle, reading endless articles a day. It was overwhelming. Now, I strike a balance to stay sane. Live your life and be aware of current events but stop before you become over-stimulated. Mind you, you may not master this balance — right away or ever — but bringing awareness to these habits can restore a healthier mindset.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be?

It may sound ironic, but I want people to rethink the way they use technology — even if it means using it less. Members of our society are so quick to judge because the media moves so quickly, constantly spreading information. In response, there is a movement of people raising awareness around how much social media and news has taken over our lives. My goal would be to help people make technology and screen work for them, ensuring it truly benefits them or helps their business operate more efficiently. It’s a fine line.

Is there a person in the world whom you would love to have lunch with, and why? Maybe we can tag them and see what happens!

Michael Jordan — it’s cheesy, but I’ve always been enthralled by his competitiveness. You’ve seen the Last Dance, right?

How can our readers further follow your work online?

You can follow me on LinkedIn, especially for the latest on our exciting work at DaySmart!

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