Jack Plotkin

Start by understanding yourself. Understand your purpose in the context of a professional career. Then, proceed backward from that to figure out the type of organization you want to work for and the sort of work you want to do.


Jack Plotkin is the CEO of Cardinal Solutions, a boutique advisory and investment firm based in New York City. He has more than two decades of experience at the crossroads of business and technology and has advised more than a hundred Fortune 500 firms across all major industries, including healthcare and life sciences.

Where did the idea for Cardinal Solutions come from?

After I graduated from Harvard in 2000, I did the investment banking thing and had the chance to advise Fortune 500 companies on billion-dollar financial strategies.

This work and experience were invaluable, but I realized I wanted an opportunity to go beyond finance I decided to pursue an entrepreneurial career at the nexus of business and technology.

In 2012, I opened my own advisory and investment company, and that was the beginning of Cardinal Solutions. I get to help build startups as well as consult with established companies.

What does your typical day look like and how do you make it productive?

Every day is a little bit different.

I focus on solving strategic issues across a broad range of problems. The diversity greatly appeals to me—I have the opportunity to deal with a full spectrum of challenges and explore different perspectives.

I generally start the day by eating the elephant, so to speak, and reviewing my email. After that, I get to work on key business deliverables. This includes research, analysis, and meetings with everyone from line personnel to C-suite executives.

Given what I do, the workday never really ends, and I take business-related calls right up until the wee hours on some days.

I try to make the most of my time by prioritizing tasks and batching similar tasks together. This way, I have time to complete my work and still make it to key meetings.

How do you bring ideas to life?

I have a lot of experience in not only building technologies but optimizing the processes behind those technologies. I studied some computer science at Harvard and still leverage that background in some of what I do. I have always been incredibly excited about technology’s potential to shape humanity’s future in unimaginable ways.

I’m driven by a desire to genuinely help my clients. I approach situations with a fresh eye and curiosity to bring new solutions to the table. The key to success is to pair transformative innovations with a solid business strategy and quality execution to make those ideas real.

What’s one trend that excites you?

I have done a lot of work in the healthcare field and I see a lot of exciting developments on the horizon.
In the coming years, healthcare is going to become increasingly personalized and digitized. There is a rising focus on the concept of “patient engagement” in healthcare, resulting in everything from patient portals for viewing prescriptions and labs to automated text messages for appointments to connected devices for tracking vitals. But that’s just the beginning. From AI to digital therapeutics, we are standing on the precipice of a tectonic shift.

New healthcare technology start-ups are appearing all the time to challenge the status quo and bring new ways of thinking. It’s an exciting time.

What is one habit of yours that makes you more productive as an entrepreneur?

I never learned how to multi-task. My key to productivity is maintaining a single-minded focus on the task at hand. I want to make a tangible positive impact on the world, and I know that I can only make that happen when I’m executing as well as I’m ideating.

What advice would you give your younger self?

Be patient. Be thoughtful. Start by understanding yourself. Understand your purpose in the context of a professional career. Then, proceed backward from that to figure out the type of organization you want to work for and the sort of work you want to do.

Tell us something that’s true that almost nobody agrees with you on.

Great teams are always better than star players. We focus so much on stars in sports, in politics, in business, but throughout history the most amazing accomplishments were always done by cohesive, collaborative teams. Whether it was the U.S. hockey team winning gold at Lake Placid, or putting a man on the moon, or the invention of the first Apple computer – it was not the coach, the astronaut, or the entrepreneur but rather the team they were part of that made the impossible possible.

As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?

From time to time, let your mind wander. Read a book in a new field, listen to a podcast about a new subject, take a class in a new arena. When your mind returns to the problem at hand, it will often surprise you with new insights and perspectives.

What is one strategy that has helped you grow your business?

I have been fortunate to receive advice and help from people at every level and every walk of life. The most important lesson I learned is that you should always keep an open mind and never assume that someone is not qualified to give you advice just because of their age or job title.

Some of the best advice I’ve received was from people who were younger, or less experienced, or from a different profession or walk of life. Rather than judge the messenger, be thoughtful about the message.

What is one failure you had as an entrepreneur, and how did you overcome it?

I built a product based on a business model that sounded good in theory but failed miserably in practice. At that point, I could have quit but I knew the product had great potential. Together with our small team we were able to pivot and find a different business model for the product. In the end, the product transformed an entire industry. It taught me that a failure doesn’t have to be a stumbling block, but can actually be a stepping stone to your greatest success.

What is one business idea that you’re willing to give away to our readers?

One business idea that I think could work is a 100-calorie dessert shop. Kind of like the dollar store, but instead of every item costing a dollar, every dessert would be 100 calories. That way your customers can indulge without feeling guilty.

What is the best $100 you recently spent? What and why?

The best $100 I recently spent was on a sushi dinner at Zawa on the Upper East Side in New York City. It’s a very unassuming place, but for die-hard sushi fans, it’s a true hidden gem. Their blue-fin tuna is out of this world. And we were celebrating a close friend getting a new job, so the occasion made it that much more special.

What is one piece of software or a web service that helps you be productive?

I probably sound like Johnny-come-lately, but Slack is a great piece of software for staying connected and being productive. I like that it’s minimalist, functional, and designed exceptionally well for what it does.

What is the one book that you recommend our community should read and why?

I would recommend Tribal Leadership. It should be required reading for anybody who wants to build or be part of a high-performing team. It’s eye opening.

What is your favorite quote?

My favorite quote is “You don’t have to be great to start, but you have to start to be great.”

Key Learnings:

• Diversify your mindset. When your mind is strongly disagreeing with someone’s opinion, assume they’re right and see where it takes you.
• Don’t be limited by the established way of doing things. When someone says that something is impossible take it as a challenge to find a way.
• The most important goal of creating a business is to make a lasting, positive difference in the world. Money and success are just byproducts.


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