Wisdom From Wizards with Nitin Kartik

Would you rather own 60% of a $30 million business or 10% of a $300 million one? That's the question we discuss with Vivian Allen, CEO at SigmaPro in Wisdom From Wizards episode 382.

Vivian chooses 60% of the $30 million business.

Not because the calculator is broken.

She explains that success is not always about maximizing the size of the pie. For her, it is about knowing yourself, leaning into your natural strengths, and having a gr...

Would you rather lead through expertise or relationship trust? That's the question we discuss with Fathy Shetiah, CEO at 7C Lingo in Episode 381 of Wisdom From Wizards.

Fathy makes a great distinction: expertise gets you a seat at the table, but trust is what actually gets things done.

For CEOs thinking about writing a book, that matters.

Your expertise may convince someone to pick up your book. But your stories, perspective, honesty,...

Would you rather pioneer a category early or dominate a proven market leader? That's the question we recently discussed with Geoff Rego, CEO at Hushly in Episode 380 of Wisdom From Wizards.

Geoff’s answer: be early, but don’t be first.

He explains that the first company often wins the press, while the second, third, or fourth may win the market. Why? The pioneer spends years, and plenty of cash, educating everyone about t...

Would you rather meditate daily or workout daily? That's the question we recently discussed with Kristina Gent, CEO at SIX° Connections.

Kristina chooses lifting weights. It makes her feel strong, gives her mind a break, and becomes its own form of meditation.

There is a useful lesson here for CEOs thinking about writing a book: clarity does not always arrive while staring at a blinking cursor. Sometimes your best ideas show up while...

Would you rather win awards or win advocacy? That's the question we recently discussed with Scott Arias, Founder at ACE Consulting Company.

Scott chooses advocacy, even with five years on the Inc. 5000.

He shares why ACE invests back into its local community and why advocacy matters especially when connecting with Gen Z, who increasingly want to support something bigger than themselves.

For CEOs thinking about writing a book, there&rs...

Wisdom From Wizards #377:

Would you rather hire highly independent thinkers who challenge decisions or highly aligned operators who execute flawlessly? That's the question we recently discussed with Ed Macha, CEO at Reliable Controls.

Ed’s answer is both, depending on the role.

He wants C-suite leaders who challenge his thinking and field teams who follow procedures with precision. One group questions the playbook. The other run...

Would you rather retire wealthy or fulfilled? That's the question we recently discussed with Dave Hansen, CEO at ClientTether.

Dave admits fulfillment does not exactly cover the dinner bill, but he still chooses it over a bigger bank balance.

He shares that successful people rarely reach the end of life wishing they had earned more. They think about legacy, relationships, and whether they left people and communities better than they ...

Would you rather manage global risk or local complexity? That's the question we recently discussed with Barri Blauvelt, CEO at Innovara.

Barri explains that global risk does not faze her team. The bigger challenge is the economic cycle.

When markets weaken, training and development is often one of the first corporate budgets to meet the red pen. Internal trainers also protect their roles, making outsourcing less likely.

For CEOs think...

Would you rather do 10 podcasts or one keynote in front of 5,000 people? That's the question we recently discussed with Eric Pratt, CEO at Instrumental Group.

Eric chooses the keynote.

Podcasts are valuable, but the audience can be mysterious. Who is listening? When will they listen? Are they taking notes or reorganizing the garage?

A keynote offers greater predictability. You know exactly who is in the room, and 5,000 people are a pr...

Would you rather focus your roadmap on user demand or internal vision? That's the question we recently discussed with Rich Sheridan, CEO at Menlo Innovations.

Rich chooses user demand because customers are the experts on the problems you are trying to solve. But he also leaves room for visionary leadership. After all, customers can tell you where the shoe pinches, but they may not sketch the next sneaker.

For CEOs thinking about writ...

Would you rather have a team that over communicates or over delivers? That's the question we recently discussed with Jennifer Schielke, CEO at Summit Group Solutions.

Jennifer chooses over communication, and her reasoning is one every CEO should hear.

Over delivery may look great on the scoreboard, but if your team is exhausted by halftime, the strategy is not sustainable. Strong communication keeps everyone in position, prevents cos...

Would you rather handle a failed launch or a failed hire? That's the question we recently discussed with Eric Chang, CEO at Claira.

Eric chooses the failed launch.

Why? A launch is like a missed shot on goal. You study the replay, adjust the formation, and take another shot. In an early-stage AI company, experimentation is part of the game.

A failed hire can be more like losing your goalkeeper in the first ten minutes. On a small team...

Would you rather be loved by engineers or by customers? That's the question we recently discussed with Drew Sechrist, CEO at Connect The Dots.

Drew’s answer is refreshingly simple: customers.

Engineers may build the elegant product. They may admire the architecture, the clean code, the beautiful design. But customers are the ones who write the checks.

For CEOs thinking about writing a book, there’s a big lesson here.

Don&rs...

Would you rather dominate a niche or shape a category? That's the question we recently discussed with Bonnie Hagemann, CEO at EDA Inc.

Bonnie’s answer? Both.

Her company is building CultureView, an AI platform that replaces the need for traditional culture engagement surveys. Since they are first in the space, the opportunity is not just to win a niche, but to define the category.

That’s a useful lesson for CEOs thinking a...

Would you rather partner with innovators or hire them? That's the question we recently discussed with Andrew Devlin, CEO at Pitchhub.

Andrew shares that the best innovation often happens at the edges of the ecosystem. Partners bring speed, leverage, fresh thinking, and, best of all, they do not require you to add another person to the Monday morning meeting calendar. Small mercy.

The same applies to your book.

You do not have to build...

Would you rather promote loyalty or push for ambition? That's the question we recently discussed with Mark Michael, CEO at DevHub.

Mark shares a refreshingly honest take: loyalty sounds noble, but leaders can overdo it. Sometimes the best thing a company can do is become the launchpad for someone’s ambition.

That’s a powerful mindset for CEOs thinking about writing a book.

Your book should not just ask people to stay loyal...

Would you rather win market share in a declining industry or hold steady in a booming one? That's the question we recently discussed with Ari Tulla, CEO at Elo Health.

Ari shares a simple but powerful answer: find the wave.

As a surfer and rock climber, he knows effort matters, but direction matters more. You can paddle heroically on a flat ocean and still go nowhere. Very motivational, except for the going nowhere part.

For CEOs thin...

Would you rather have a leadership style that inspires loyalty or one that drives performance at any cost? That's the question we recently discussed with Milind Katti, CEO at Demand Farm.

Milind chooses loyalty.

Not the “please like me, I brought donuts” kind of loyalty.

He talks about loyalty as self-drive, motivation, intent, and effort. The inputs that eventually create performance.

That’s a powerful insight for CE...

Would you rather dominate one geography or diversify across five? That's the question we recently discussed with Jason Pearsall, Founder of Club Caddie.

Jason chooses focus.

For Club Caddie, that means North America, especially the United States. Why? One language. One currency. One major set of expectations. One market deep enough to build a real machine without turning the team calendar into a 24-hour support smoothie.

That same les...