HomeSocial Impact HeroesMichael Ryan Of On 5 Things They Forgot To Mention In...

Michael Ryan Of On 5 Things They Forgot To Mention In College

An Interview With Chad Silverstein

Roll with the punches. College teaches theories and models, but nothing prepares you for the unpredictable ups and downs of the real business world. Like lessons I learned from my dad and grandma, you have to adapt and find balance. Remember, the road to success is never a straight line — it’s a winding path full of twists and turns. You need agility and resilience.

We are starting a new interview series about the world of entrepreneurship beyond the classroom — a realm where theory meets grit, and education meets real-world challenges. We want to hear about critical business wisdom that often goes unspoken in academic settings. I had the honor of interviewing financial expert Michael Ryan.

Michael Ryan’s nearly thirty-year journey in finance has shaped him into a trusted guide in the realms of wealth management and retirement planning for affluent families and business owners. His expertise, honed over decades of hands-on experience, now finds a new home at, where he shares his knowledge through financial coaching. This platform reflects Michael’s commitment to financial education, offering a wealth of resources that empower individuals to take charge of their financial paths. His dedication to fostering financial savvy and self-reliance cements his reputation as a steadfast ally in the pursuit of financial security and independence.

Thanks for being part of this series. Let’s jump in and focus on your early years. Can you share who was your biggest influence when you were young and provide specific examples of what you learned from them that helped shape who you’ve become and how you live your life today?

Man, looking back I’m still kind of confused about how big of an influence my dad was, even though he was never around much. He was laser focused on making money, so he just wasn’t there for me and my sister. His #1 priority was gaining wealth, not being a good husband or dad. I guess that drive to make money is what led to my parents splitting up when I was just a kid. My mom had to raise me and my sister alone without a whole lot of money.

At the same time though, my grandmother also played a huge role. Since she lived through the Holocaust, she knew better than anyone not to take family for granted. She drilled it into my head when I was young that family should be above everything else, no matter what. I didn’t fully get it back then, but her words stuck with me.

Later when I started my own financial planning practice, I noticed myself picking up some of the same habits as my dad — working nonstop crazy hours and not making time for loved ones. I decided I didn’t want to end up like him, rich but alone. So I put a little note on my desk to remind myself: “You can choose more time or money — you can’t have both.” It helped me keep my priorities straight and leave work at a reasonable hour to be present with my wife and kiddos. In a roundabout way, my dad gave me a lesson in finding balance and not losing sight of what really matters most. His absence taught me the value of being their for the people you care about.

Staying on the topic of influence, who has been your biggest catalyst more recently and what can you share that you’ve learned from them that led you to making changes in your life?

You’d probably expect me to say a mentor or coworker has influenced me most recently. And I do have a long list of those. But you asked recently. And honestly, it’s been my kids who’ve been the biggest catalysts for me. And it’s because I am at the point in my life where I am thinking of giving back and getting the next generation to take over.

Watching my kids grow up and transform into adults, I’m constantly blown away by how mature and insightful they are. Way more than I was at their age. Their natural potential and passion for making the world a better place has inspired me to rethink my own perspectives and how I approach change.

They remind me every day that the ability to shape the future isn’t about years of experience — it’s about the freshness of your ideas and having the courage to go after them. My children keep me feeling young, hopeful and driven to do meaningful work that will make their future bright.

In this interview series, we aim to reveal what seasoned entrepreneurs wish they had known when they were starting out and capture what the textbooks and college professors left out.

This topic of getting real-world ready couldn’t be more relevant right now. I’m seeing it firsthand as my own kids go through school and start their early careers. My oldest is a junior in college and my youngest is applying as we speak. They’re right at that transition point.

I was chatting with my son and some of his college friends recently, and a lot of them expressed feeling anxious about entering the “real world” after graduation. They said they wanted more practical knowledge — like how to manage money, understand paychecks, and save for the future.

So, we had this impromptu session around my kitchen table where I walked them through stuff like setting up bank accounts, how paychecks work, the power of compound interest, and why it’s so important to start retirement savings like a 401(k) early on. It was eye-opening for me too, realizing there’s a major gap in our education system when it comes to basic financial literacy.

Since then, I’ve been passionate about trying to fill that gap, not just for my own kids but for any young person about to leave school and enter the real world where theory gets replaced by tangible things. I want the next generation to feel confident and prepared, not anxious about handling their finances in the workplace.

Mistakes are invaluable. Can you name one specific mistake that you made early on, and learned the most from, but wish you’d been forewarned about?

The fear of failure was a formidable adversary in my journey, especially as a self-confessed perfectionist. It was a mentor who shifted my perspective with a simple, yet profound question: “Why fear failure when it’s an inevitable part of growth?” He likened it to Wayne Gretzky’s famous adage, “You miss 100% of the shots you don’t take.” This conversation illuminated the self-sabotaging nature of my fear

An example that stands out is when I launched a new financial product I believed had immense potential. Despite meticulous planning, it didn’t take off as expected. Initially, I was disheartened, but then I chose to view it through a lens of learning rather than one of failure. I dissected every aspect of the process, from conception to execution, and it became clear that I had overestimated market readiness for such an innovation.

This ‘failure’ was a turning point. It taught me to better gauge market trends and client readiness, leading to improved strategies for product launches in the future. Embracing this experience as a success in learning rather than a failure in execution has been instrumental in my professional development.

Is there a leadership myth you believed early on that you’ve since debunked through your real-world experience?

One of the most pervasive myths I held as a financial planner was the belief that I needed to have all the answers. This notion was deeply rooted in my perfectionist tendencies — how could I be seen as an expert if there were gaps in my knowledge? Clients came to me seeking guidance to their financial goals, and I felt immense pressure to be their infallible compass.

This myth was shattered by an estate attorney colleague, Ben, during a joint client meeting. When posed with a question, he casually admitted he didn’t know the answer but promised to follow up. I was taken aback, especially since I knew Ben was well-versed in the subject. He later explained that clients respect and appreciate the honesty and diligence of verifying information before providing an answer.

Taking a leaf out of Ben’s book, I decided to adopt this approach. The impact was immediate. At the end of a consultation, a client commended me for not fabricating a response on the spot, expressing appreciation for my commitment to accuracy over appearance. This experience was a turning point, teaching me that true expertise isn’t about having all the answers — it’s about dedication to finding the right ones.

What’s the key operational insight you’ve gained since running your business that was never mentioned in any classroom?

The most critical operational insight I’ve gained is that the essence of running a business is not captured in textbooks. While my academic background in business, finance, and accounting provided a foundation, it’s the hands-on experience of navigating through mistakes that truly educates an entrepreneur. Earlier, I touched on the fear of making mistakes and my tendency towards perfectionism. Overcoming this has been pivotal.

In practice, I’ve learned that there’s no one-size-fits-all approach to business. It’s about discovering what uniquely works for you and your enterprise. This involves seeking mentorship, embracing continuous learning, and being adaptable to acquire the specific knowledge needed at various stages of your business journey.

Did college prepare you for scaling a business? What specifically was missing?

College gave me a good baseline education, but running a successful business requires skills that go way beyond just book learning. What I realized was missing from my schooling was the art of delegating tasks and hiring the right talent. You don’t need to be an expert on every legal and tax detail yourself — it’s about recognizing when you should bring in specialists, like really stellar CPAs and lawyers, who can handle the complex stuff for you.

The key is surrounding yourself with a team who complement your strengths and fill in gaps in your expertise. I had to learn that I can’t do it all alone. If I am the dumbest one in the room, then my business will do just fine!

The schools don’t really teach you how to identify and empower others who can take things off your plate so you can focus on the big picture vision and strategy. That’s been crucial for me in terms of scaling my company beyond what I could accomplish solo. So while college provided the fundamentals, growing a successful business required skills I could only pick up through hands-on experience.

Any unexpected challenges in team dynamics that your academic experience didn’t prepare you for? How did you handle it?

Do you remember having to do group projects in school? And we all hated them, because every team would have the know it all, and another member who didn’t contribute anything. Welcome to the real world…

Traditional academia didn’t really prep me for navigating the complexities of human behavior and team dynamics in the workplace. That’s an area I think every college program should cover, maybe with classes in psychology or something.

I remember my mentor Mitch — he had this unbelievable ability to just understand people on a deeper level. He could read a room instantly and always knew how to communicate in the moment. I was so impressed watching him. He inspired me to work on developing that talent myself throughout my career.

Whether you’re dealing with employees, clients, vendors, whoever — being able to pick up on interpersonal cues and intuit what to say when is so valuable. It’s a skill that goes beyond any one field or industry. I’m still working on getting better at it, but I’ve realized firsthand how crucial it is to understand both the logical and emotional sides of working on a team. The human element is something the textbooks never really prepared me for.

Have you had to unlearn any widely-accepted business ‘wisdom’ in your journey? What was it and how did it affect your strategy?

Over my years as a financial planner, there’s one common saying I’ve had to unlearn — “the customer is always right.” Now don’t get me wrong, I’ve always valued client relationships highly and treated people’s financial goals with care, like I would with family. But I realized that doesn’t mean clients always see the full picture.

There were definitely times when a client wanted to go in a certain direction that I knew from experience wasn’t actually best for them financially. It was a tricky balance to guide them towards a better path without compromising my professional principles.

This led me to take a more collaborative approach, where open communication and mutual respect are key. I found that by engaging clients in the decision-making process, explaining the reasoning behind strategies, and even pushing back on their ideas sometimes, we can land on outcomes that truly serve their long-term financial well-being. It’s not about who’s right or wrong — it’s about doing what’s right for the client.

I applied this principle internally too, recognizing that as an advisor, I’m not infallible either. I actively sought out my colleagues’ insights and encouraged roundtable discussions to ensure we designed the best strategies for our clients. That humility and openness to collective wisdom have been so important for improving my practice and delivering top-notch service.

What’s your advice for new entrepreneurs? What are your “5 Things You Won’t Learn in College But Must Know to Succeed in Business”?

Roll with the punches. College teaches theories and models, but nothing prepares you for the unpredictable ups and downs of the real business world. Like lessons I learned from my dad and grandma, you have to adapt and find balance. Remember, the road to success is never a straight line — it’s a winding path full of twists and turns. You need agility and resilience.

Relationships over transactions. In my practice, I realized clients aren’t just numbers on a sheet — they’re partners in a journey. No college course teaches you to build the human connection and trust needed to turn clients into friends. Make those relationships a priority — they’re the foundation of successful businesses.

Listen to life’s whispers. Your best teacher can be your own experiences. My kids, with their fresh takes, showed me profound lessons can come from unexpected places. Be open to learning from everyone and everything around you, even life’s silent whispers.

Master delegating. College may teach self-reliance, but real success means building a team you trust. Just like I had to leave work to spend time with family, learn to delegate — to empower others and grow beyond your personal capacity.

Unlearning matters too. As I navigated my career, I had to unlearn the myth of “the customer’s always right.” You’ll need to shed preconceived notions and relearn too. Unlearning allows you to stay nimble, adapting to the ever-changing business landscape.

These insights won’t be found in any textbook — they come from the trenches, blending professional wisdom and personal growth. Essential stuff for any entrepreneur about to dance with the complex world of business.

How do you ensure your team not just understands but embodies your business principles? Any techniques you wish you’d known earlier?

Lead by doing. Nothing convinces people more than seeing principles in action. If you demonstrate a real commitment to company values in your own behavior, your team will likely follow. For example, if family is a core value, show it by respecting work-life balance for yourself and your crew.

Tell stories. Use real examples of how sticking to business principles has positively impacted the company. Share client experiences, business decisions, personal anecdotes — make those abstract principles tangible through narrative.

Spotlight rockstars. Publicly highlight when team members showcase core principles. This encourages them and sets a clear example for others to emulate. It’s a proactive way to reinforce the behaviors you want to see, making the principles lived experiences, not just concepts.

These strategies are interconnected. Leading by example lays the groundwork. Storytelling provides the narrative. Recognition ties it all together, creating a culture where principles aren’t just words on paper — they’re the bedrock of how we work every day.

If we were sitting together two years from now, looking back at the past 24 months, what specifically has to happen for you personally and professionally, for you to be happy with your results?

Looking back in two years, what really counts for me boils down to some simple stuff.

Personally, I just want to know my family’s healthy and happy. That we’ve had more good days than bad ones, and made a ton of great memories together. It’s the little things that matter most — Sunday dinners, game nights, that kind of quality time.

Professionally, I’d be pumped if I really helped people get smarter with money, and maybe made their lives a bit easier because of it. It’s not the amount you have, but what you do with it that can make life better.

So yeah, at the end of the day, it’s about enjoying the simple joys and being there for one another. That’s my goal.

Looking back over the last two years, what key accomplishments make you satisfied with your progress?

On the personal side, I’m proudest of all the quality time I’ve put in with my family. Being there for the big moments and the small ones — my kids’ milestones, weekend hangouts, all of it — has brought us so much closer. Those times together are what really make me feel successful in what matters most.

Professionally, it’s been super rewarding to help guide my clients towards financial stability and confidence. Seeing them reach their goals, whether it’s saving for college, planning for retirement, or just getting better at managing money day-to-day, feels amazing. It’s not just the numbers — it’s giving people that peace of mind and security that comes with solid financial planning.

And lastly, I’m proud of pushing myself to keep learning. Staying current on the latest in finance, adapting to new tech and methods, has let me provide the best service possible. It’s an endless process, but one I find fulfilling and key for both my own satisfaction and professional responsibility.

As someone with significant influence, what’s the one change you’d like to inspire that would benefit the most people?

If I could give one piece of advice, it’d be this — start thinking about money the minute you step into adulthood. I’m talking your college years when you’re figuring out loans and costs. That’s where it all kicks off, and it’s a big deal.

Fast forward to landing your first gig after school. Here’s where things get real. Forget trying to keep up with everyone else — that’s just noise. The focus is you. Make smart money moves early on and you’re not just saving for a rainy day — you’re building a fortress for your future self.

See, every smart choice you make, every penny you save, it all adds up over time. It’s like rolling a snowball down a hill — it keeps growing. And the people who get this right from the start? They’ll have the freedom later to do what they love, not just what pays the bills. That’s the shift I want to see happen.

How can our readers keep up with your work?

For anyone interested in following along with my journey and getting my take on financial planning and money management, swing by my website There you’ll find tons of helpful resources, updates on stuff I’m working on, and my latest thinking on how to turn your financial goals into real results.

I’m always adding new content and commentary there, so it’s a great way to stay up to date on my work in the world of personal finance. Whether you’re just starting out or have been at this a while, I hope you’ll check out the site and reach out with any questions. I’m excited to keep sharing my passion for helping people gain confidence and clarity around their money situation.

Thank you so much for joining us! We wish you only success.

About the Interviewer: Chad Silverstein is an accomplished entrepreneur and visionary leader. He started his first company, Choice Recovery, Inc., while attending Ohio State University and grew it to become an industry outlier before selling the business after 25 successful years. With the launch of his second venture, [re]start, a career development platform, Chad aimed to help people find meaningful career opportunities. Under his leadership, his team was recognized as a “Top Workplace” award winner for over a decade, twice being ranked the #1 small and medium-sized business to work for in Central Ohio. Chad sold [re]start in 2023, enabling him to focus on building an online community of high-performing leaders and continuing to make a positive impact in people’s lives.

Michael Ryan Of On 5 Things They Forgot To Mention In College was originally published in Authority Magazine on Medium, where people are continuing the conversation by highlighting and responding to this story.