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Gabe Krajicek of Kasasa On How Leaders Make Difficult Decisions

Look for Levers to Impact or Change the Outcomes: Once you’ve got your mental model, the next step is to identify the levers you can pull to influence those outcomes. What can you do to mitigate risks or increase the chances of a positive result? When we faced a serious regulatory issue at BancVue, we spent a lot of time thinking through all the ways we could mitigate the impact. We engaged with regulators, tweaked our products, and communicated openly with our clients to navigate the crisis. It was all about finding those levers and using them effectively.

As a leader, some things are just unavoidable. Being faced with hard choices is one of them. Leadership often entails making difficult decisions or hard choices between two apparently good paths. What’s the best way to go about this? Is there a “toolkit” or a skill set to help leaders sort out their feelings and make the best possible decisions? As part of our series about “How Leaders Make Difficult Decisions,” we had the pleasure of interviewing Gabe Krajicek, CEO of Kasasa.

Gabriel (Gabe) Krajicek, CEO of Kasasa®, empowers community financial institutions with disruptive banking technology innovations and go-to-market strategies, challenging megabanks and new players. Since 2005, he and his team have equipped over 1,000 banks and credit unions with tools to drive new deposits at a lower cost and higher retention rate, resulting in roughly $20B in deposits for partner institutions. Kasasa ranks as the fourth largest bank in branches. Gabe is a recipient of EY Entrepreneur of the Year Central Texas. A Vanderbilt MBA graduate, Gabe led DealerSkins before its acquisition by Trader Publishing.

Thank you so much for your time! I know that you are a very busy person. 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?

During my junior year, while attending LSU for undergraduate school, I had been accepted to Emory Medical School. At that time, my stepmom encouraged me to take the Johnson O’Connor aptitude test, which evaluates various skills, including spatial orientation, numerical ability, memory, and hand-eye coordination. Unfortunately, I scored in the bottom 15th percentile for hand-eye coordination, which was not good for my goal of becoming a surgeon. It was clear that this was not the right career path for me, but the test indicated I had strong entrepreneurial potential. So, I continued on at LSU, finishing out with a degree in Zoology with a minor in Business.

During that time, my dad, who was battling brain cancer, spent his final year guiding and mentoring me. He was an entrepreneur and together we developed a business plan for Yankz, a company that produced shoelaces for triathletes, based in Lake Charles, Louisiana. We raised about half a million dollars for the company.

A year after my father passed away, I left the company and moved to Nashville, Tennessee, to work at a boutique investment bank with Private Capital Advisors. This was during the “dot-com” boom, and we were fundraising for early-stage tech companies, but many were failing, and investors were hesitant.

My boss gave me a choice: he would either let me go or I could take over as CEO of one of the companies we had put together at the investment bank. The CEO of this company, which built websites for car dealerships, was not working out, and I was offered the opportunity to lead it. At 22, I faced the choice of being laid off or running a company with very little experience, I chose the latter, which is where my CEO journey began.

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

I’m a big believer that none of us achieve success on our own — there’s always someone who plays a pivotal role along the way. For me, one of the most pivotal people is Vennesa Van Ameyde, our president at Kasasa. We’ve been working together for more than two decades now, and our professional relationship has been one of the most important of my career.

I first met Vennesa when I hired her at DealerSkins, and she was the last person I brought on board there. Even during her interview, she stood out — not just for her skills, but for her approach to leadership. She prioritizes a culture of high love and high excellence, which are values that I feel are mission critical for success. We later worked together at BancVue, where she ran marketing and operations, and now she’s my right hand at Kasasa.

What makes our partnership so strong is the empathy and interpersonal connection we’ve built over the years. She’s not just a colleague; she’s someone who understands the importance of balancing results with relationships. In every challenge we’ve faced together, she’s been someone who can navigate complex situations with both precision and heart, and I’m incredibly grateful for her partnership.

Thank you for all that. Let’s now turn to the main focus of our discussion. Can you share with our readers a story from your own experience about how you lead your team during uncertain or difficult times?

There are plenty of stories to choose from, but one that stands out to me is from a few years back. We were dealing with a serious compliance issue — our product was found to be in violation of an obscure federal regulation. We were in a tough spot because we needed the cash flow from setup fees, but we couldn’t legally launch any new FIs until we fixed the issue.

I had to lead the team through three intense months with attorneys and regulators to make the product compliant. During that time, we kept selling — transparently — offering places in the queue for when we could go live again. It was a tough call, but it was about survival, and leading from the front was crucial. I was right there in the middle of it with the team, ready to fight the good fight and not quit.

Another recent example is the turnaround during COVID. In 2019, we had a regulatory issue pop up, branches were closing, and we had to operate remotely. I started doing weekly video updates to keep the team connected, and we set up Zoom groups to maintain transparency and human connection. But it wasn’t quite creating the culture we wanted, so we made the decision in early 2024 to move everyone back to the office. It was risky with tons of uncertainty, but in those moments, how you react is everything. I focused on being present with the team, helping to problem-solve, and doing whatever we could to increase the probability of a good outcome.

Did you ever consider giving up? Where did you get the motivation to continue through challenges? What sustains your drive?

I never seriously considered giving up, at least not where I’d actually do it. But there were definitely dark moments where doubt would creep in, and I’d find myself battling between belief and uncertainty. It’s a real struggle, and I think it’s normal for any entrepreneur, founder, or leader to face those feelings.

What kept me going was the people around me — my coworkers and executive team. We all agreed to stick together and see things through, and that high level of trust was a huge motivator.

In those tough times, you need two things: first, you have to believe, logically, that you can get through it. And second, you need a team of people who believe it with you. That shared belief and the way we lifted each other up made all the difference. There’s something powerful about “shared suffering” — it builds camaraderie and resilience. Having a team that sticks together and inspires each other is what sustains my drive, even in the toughest moments.

Leadership often entails making difficult decisions or hard choices between two apparently good paths. Can you share a story with us about a hard decision or choice you had to make as a leader?

You could put all decisions into three buckets.

Easy decisions are easy; pick the right, most profitable thing. If given the choice between helping people and making a million dollars or hurting people and losing money, this isn’t really a choice, right? Few of these make it to the CEO’s office.

Hard decisions are ethically neutral, but suffer from uncertainty. These are the bulk of the decisions a leader faces. Both paths seem equally profitable and predicting outcomes is nearly impossible. For example, we once had to make choice on what product strategy to pursue. We could have invested more heavily in building out the marketing side of our service offering or create a new loan product. Even with lots of surveys and market testing, it wasn’t clear which would be the better new product. So how do you pick? I’d suggest picking the path you think will be most exciting for the team. Usually even when there is a quantitative tie, there is qualitative enthusiasm behind one of the ideas. In the end, the enthusiasm will be the difference maker; go where the energy is (loans in our case).

Values-based decisions are different in kind. These decisions tend to pit what aligns with your personal values against that which generates the most profit. I don’t feel comfortable telling others what to do in those situations. But for me, the filter is, “How will I feel about this when I’m dying and looking up at my kids? will they be proud of me?” That usually clears up any ambiguity pretty darn quickly.

What process or toolset can a leader use to make a choice between two difficult paths?

Traditional tools like making a pros and cons list or modeling outcomes can only take you so far. Those methods are useful, but they don’t always capture the full picture, especially when it’s a good/good trade-off where either choice has merit.

One approach I’ve found valuable is something I learned from Jonathan Coon, founder of 1–800-Contacts — it’s the idea of regret avoidance. Ask yourself, “Which decision am I least likely to regret five years from now?” It forces you to think long-term and consider the impact of your choices on the future, not just the immediate outcomes.

But honestly, a lot of it comes down to trusting your gut. You have to follow your intuition and ask yourself, “As the hero of this story, what am I supposed to do?” It might not always be what you want to do, but deep down, you know it’s the right thing to do for the audience — whether that’s your team, your customers, or your community. It’s about doing what’s right, not just what’s easy or beneficial in the short term.

At the end of the day, when it comes to making those tough calls, it’s about listening to that inner voice, understanding your role in the bigger narrative, and making the choice that aligns with your values and the long-term vision, even if it’s the harder path to take.

Do you have a mentor or someone you can turn to for support and advice? How does this help? When can a mentor be helpful? When is this not helpful?

I’ve had many mentors over the years — business coaches, chairmen of the board, and others. I think it’s crucial to have people you can turn to for support and advice. Mentors are incredibly helpful when you’re driving the ship and need a sounding board to bounce ideas off of. They can provide perspective, share their experiences, and help you think through tough decisions.

But there’s a fine line. A mentor is there to guide you, not to tell you what to do. It’s a mistake to lean too heavily on them for answers. That’s a bad mentee move. The real value of a mentor is in their stories and the wisdom that comes from their experiences. Listen to those stories, extract the lessons, but don’t expect them to give you a step-by-step guide on what to do next.

As a leader, it’s your job to evaluate the data, consider the advice, and then make the decision. You have to own it because, at the end of the day, you’re the one steering the ship. I’ve made the mistake in the past of relying too much on advice instead of trusting my own judgment, and that never works out well. Your mentors are tools in your toolkit, not the decision-makers. You’re the one who has to lead, make the call, and be the cause of the force driving your company forward.

What would you say is the most critical role of a leader when faced with a difficult decision?

To lead with conviction. That doesn’t mean you can’t change your mind if new information comes to light, but you can’t afford to be double-minded. The team will sense any hesitation or uncertainty, and that can undermine their confidence in the direction you’re leading them.

Take, for example, the decision to move back to the office. It wasn’t an easy call, but once I made it, I had to deliver that message with certainty and honesty. It’s about speaking your truth with a tone of authenticity — that’s what makes your message magnetic. If you’re clear and committed, your team will follow you, even if the decision is tough.

Do you ever look back at your decisions and wish you had done things differently? How can a leader remain positive and motivated despite past mistakes?

Absolutely — every day! I think it’s only natural to look back at your decisions and see things you wish you had done differently. But the key is realizing that you can’t go back and change the past. Those decisions, even the mistakes, are the building blocks of your personal growth. They’re where the real lessons come from.

The important thing is to not make the same mistakes twice. It’s about growing your character — leveling up, so to speak. You don’t want to get stuck playing the same level over and over again. Instead, learn from those mistakes, apply what you’ve learned, and keep moving forward. Each mistake is an opportunity to become better, stronger, and more capable as a leader.

What is the best way to boost morale when the future seems uncertain? What can a leader do to inspire, motivate and engage their team during uncertain times?

The best way to boost morale when the future seems uncertain is to lead by example — exaggerate the qualities you want your team to embody. If you want your team to be resilient, focused, or committed, you need to display those traits at 150%. The reality is, they’ll likely model a fraction of what you show them, so you have to go all in.

During uncertain times, it’s also important to send clear signals about what you stand for and what you believe in. People need something to connect to that isn’t just about the outcome, especially when that outcome is unclear. Don’t tell them “we’re going to be fine” if you don’t know that for sure — that kind of false reassurance doesn’t work and can backfire.

Instead, find something authentic to say that will motivate your team to keep pushing forward. Focus on the importance of executing with excellence, regardless of what the future holds. Let them know that what matters most is how we perform and grow through these challenges. That’s much more inspiring than empty promises, and it gives the team a sense of purpose and control, even when things are uncertain.

Can you share 3 or 4 of the most common mistakes you have seen other businesses or leaders make when faced with a hard decision? What should one keep in mind to avoid that?

I’ve seen a few common mistakes that leaders, CEOs or businesses tend to make (I’ve also screwed up every one of these by the way):

  1. Copying Other Businesses: One big mistake is trying to mimic what other businesses are doing. Most businesses fail! Don’t copy for copying’s sake. That’s not a strategy — it’s a shortcut, and it rarely works. Just because something works for another company doesn’t mean it will work for yours. You have to think deeply about whether a particular decision makes sense for your business, not just follow what others are doing. Failure to think critically for yourself leads to poor outcomes.
  2. Keeping the Brilliant Jerk: Another common mistake is failing to fire the brilliant jerk. It’s tempting to keep someone around if they’re delivering results, but the hit to team morale often outweighs any benefits. When you allow toxic behavior to persist, it erodes trust and productivity across the team. Sometimes, letting go of that brilliant jerk is the best thing you can do for the overall health of your company.
  3. Top-Down Modeling: A third mistake is relying on top-down modeling that isn’t grounded in the reality of bottom-up time, motion, and unit economics. It’s easy to throw around broad assumptions — like targeting a percentage of market share — but without understanding the actual, operational mechanics, like how leads translate to sales, you’re setting yourself up for failure. There’s a big difference between saying you want to own a percentage of the market and actually building a model that reflects the day-to-day realities of your business. It’s crucial to align your models with the real-world complexity your team is dealing with.

Based on your experience and success, what are the five most important things a leader should do when making difficult decisions?

  1. Build a Mental Model of Key Outcomes: When facing a tough decision, I always start by building a mental model of the possible outcomes. Think of it like running a “Monte Carlo” simulation in your mind, where you consider all the possible scenarios and assign probabilities to each one. This helps you understand the range of potential outcomes and prepare for what might happen. For example, when we had to decide whether to move back to the office after COVID, I ran through every possible scenario — how it would impact the team, productivity, morale, and the business — to help us make a more informed decision.
  2. Look for Levers to Impact or Change the Outcomes: Once you’ve got your mental model, the next step is to identify the levers you can pull to influence those outcomes. What can you do to mitigate risks or increase the chances of a positive result? When we faced a serious regulatory issue at BancVue, we spent a lot of time thinking through all the ways we could mitigate the impact. We engaged with regulators, tweaked our products, and communicated openly with our clients to navigate the crisis. It was all about finding those levers and using them effectively.
  3. Evaluate the Impact on All Stakeholders: It’s easy to get tunnel vision and think about a decision from just one angle. But it’s crucial to broaden your lens and consider how your decision will impact all stakeholders — employees, customers, partners, and the community. When we decided to launch Kasasa during the Great Recession, we had to think carefully about how it would affect community banks and credit unions, as well as their customers. We looked at it from every side to ensure we were making a decision that would benefit everyone involved.
  4. Apply the Logic Filter: After you’ve done all your analysis — considered the outcomes, identified levers, and evaluated stakeholder impact — it’s time to apply the logic filter. What does the data tell you? What’s the best possible outcome based on all the information you’ve gathered? Logic should guide you toward the right decision. For instance, when we were in a cash flow crunch and still needed to sell, logic dictated that we be transparent with our customers about the situation. We let them know they were buying a place in the queue, not an immediate solution, which helped us maintain cash flow and integrity.
  5. Use the Gut Filter: Finally, after all the logic, you have to check in with your gut. Does this decision feel right? Do you feel okay about what you’re about to do? Sometimes the data might point in one direction, but your gut tells you something different. It’s important to listen to that. There have been times when my gut told me to pause, even when everything else seemed to line up perfectly. Trusting your intuition is key because, at the end of the day, you have to live with the decisions you make.

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

“Chance favors the prepared mind.” — Louis Pasteur. This quote captures the essence of how I approach both life and business. You can’t control the uncertainty of the world, but you can certainly tilt luck in your favor by being prepared.

In my experience, whether it’s navigating a crisis or making a difficult decision, the outcome often boils down to whether you’re ready when the moment comes. It’s easy to write off success as luck, but I believe that luck is often just preparation meeting opportunity. The energy should go into preparing yourself and your mind, so when you’re faced with uncertainty, you’re ready to take advantage of whatever chance comes your way.

How can our readers further follow your work?

You can find me on LinkedIn at: https://www.linkedin.com/in/gmkrajicek/

Visit us online at www.kasasa.com and follow us on all the social platforms!

Thank you so much for sharing these important insights. We wish you continued success and good health!

About The Interviewer: Maria Angelova, MBA is a disruptor, author, motivational speaker, body-mind expert, Pilates teacher and founder and CEO of Rebellious Intl. As a disruptor, Maria is on a mission to change the face of the wellness industry by shifting the self-care mindset for consumers and providers alike. As a mind-body coach, Maria’s superpower is alignment which helps clients create a strong body and a calm mind so they can live a life of freedom, happiness and fulfillment. Prior to founding Rebellious Intl, Maria was a Finance Director and a professional with 17+ years of progressive corporate experience in the Telecommunications, Finance, and Insurance industries. Born in Bulgaria, Maria moved to the United States in 1992. She graduated summa cum laude from both Georgia State University (MBA, Finance) and the University of Georgia (BBA, Finance). Maria’s favorite job is being a mom. Maria enjoys learning, coaching, creating authentic connections, working out, Latin dancing, traveling, and spending time with her tribe. To contact Maria, email her at angelova@rebellious-intl.com. To schedule a free consultation, click here.


Gabe Krajicek of Kasasa On How Leaders Make Difficult Decisions was originally published in Authority Magazine on Medium, where people are continuing the conversation by highlighting and responding to this story.

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