Wisdom From Wizards with Nitin Kartik

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...

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, th...

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 use...

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 appl...

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...

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...

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...

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...

Would you rather take one big risk or a hundred small ones? That’s the question we recently discussed with Adam Saghei, CEO at We Recycle Solar. Adam chooses the hundred small risks. And for CEOs thinking about writing a book, that answer matters. A bestselling book can feel like one giant leap. Big idea. Big deadline. Big public launch. Big “please don’t let my college roommate find a typo on pag...

Would you rather have your team describe you as fair or inspiring? That's the question we recently discussed with Irad Eichler, CEO at Circles. For Irad, the answer is inspiring. Why? Because his team is working on a deeply human mission: helping people facing life challenges deal with loneliness. Fairness matters, of course. Nobody wants a CEO who treats promotions like a game of musical chai...

Would you rather write a book on sales or operations? That's the question we recently discussed with Austin Burns, CEO at Burns Pest Elimination. Austin chooses operations. And honestly, that answer may not sound as flashy as sales at first. Sales gets the spotlight. Operations gets the spreadsheet. But Austin makes a powerful point: operations workflows shape the personal brand inside your bu...

Would you rather build something enduring or something exponential? That's the question we recently discussed with Ron Salazar, CEO at MR2 Solutions. Ron shares how exponential often sounds exciting, but it can turn into chasing profit. Enduring means chasing value. Pursuing enduring value applies equally to CEOs thinking about writing a book. A book should not just be a shiny credibility trop...

Would you rather have 10 loyal enterprise clients or 10,000 active users? That's the question we recently discussed with John Cecilian, CEO at Cecilian Partners. John shares that for a SaaS company like his, the answer is 10 loyal enterprise clients. Why? Because deep enterprise relationships can create stability, meaningful ARR, co-innovation, and retention. In other words, fewer customers, s...

Would you rather have perfect documentation or perfect onboarding UX? That's the question we recently discussed with Paul Powers, CEO at Physna. Paul makes a clear choice: Onboarding UX. His point is simple. Great products should not require users to earn a PhD in “Where Is The Button Studies.” Documentation has its place, especially for complex products. But the best UX removes friction befor...

Would you rather have a slow, steady growth #trajectory or take big bets that could 10x your business? That's the question we recently discussed with John Snyder, CEO at NetFriends. John shares why he prefers slow, steady #growth over giant “please let this work” gambles. His view: 10x growth sounds exciting, but it can also create 10x #chaos if you haven’t thought through the second-order eff...

Would you rather invest in people or invest in technology first? That's the question we recently discussed with Scott Eakin, CEO at Randy's Automotive. Scott’s answer is refreshingly direct: people, all day long. Technology can accelerate a business, but only if the right people know how to use it. Otherwise, it is just a very expensive way to make bad decisions faster. Basically, a shiny...

Would you rather out-price your competitors or out-think them? That's the question we recently discussed with Shekar Raman, CEO at Birdzi. Shekar’s answer: out-think them any day. Because price competition is often a race to the bottom. And sadly, “We are cheaper!” is not exactly the kind of sentence that makes customers build a statue in your honor. For CEOs thinking about writing a book, thi...

Would you rather take a big bet once a year or small bets every quarter? That's the question we recently discussed with Ganesh Gandhieswaran, CEO at ConverSight. Ganesh makes the case for small bets, especially in B2B enterprise SaaS. His point: when the market is moving fast, especially with AI, you may be early, late, or wondering if the market changed while you were opening your laptop. Sma...

Would you rather exit at peak growth or after maximizing your margins? That's the question we recently discussed with Vivek Joshi, CEO at Entytle. Vivek shares a wonderfully CEO-ish answer: it depends. In 2021, growth was the belle of the ball. In 2022 and 2023, profitability walked in wearing a tuxedo and suddenly everyone wanted to dance with margins. Seasons change. Markets change. Buyer pr...

Would you rather win an industry award or land a high profile case study? That's the question we recently discussed with Damon Lembi, CEO at Learnit. Damon chooses the high profile case study. Awards are nice. They sparkle on a website. They make your About page feel like it went to prom. But a strong case study does something more powerful: it helps prospects see themselves in your work. And...

Would you rather triple your demo conversion rate or halve your customer acquisition cost? That's the question we recently discussed with Kneko Burney Miller, CEO at Change3. Kneko chooses halving customer acquisition cost. Why? Because for her, CAC is not just ad spend, funnels, dashboards, or some spreadsheet goblin hiding in row 47. It is time. And time is the one cost CEOs cannot magically...

Would you rather stay deeply embedded in research or step fully into the CEO role? That's the question we recently discussed with Jacob Hooker, CEO at Sensorium Therapeutics. Jacob shares why he left academia and stepped into the CEO seat: impact. As a Harvard professor and researcher at Mass General, he worked on meaningful science. But leading Sensorium Therapeutics gets him closer to the pa...

Would you rather increase average revenue per user or reduce your churn? That's the question we recently discussed with Vivian Allen, CEO at SigmaPro. Her answer: reduce churn. Because churn is not just a spreadsheet problem. It is often a trust problem wearing a finance costume. Vivian explains that in industries like medical device manufacturing, switching suppliers is painful. Assets move....

We recently collaborated with Fathy Shetiah, CEO at 7C Lingo. Here we discuss why accuracy beats reckless speed when the details can make or break trust. Fathy shares how one word, one letter, one accent, one period, or one number can create serious problems in language and culture. The same is true for a CEO’s book. Yes, speed matters. Nobody wants a book project that moves slower than airport Wi...

We recently collaborated with Geoff Rego, CEO at Hushly. Here we discuss why customer adoption beats disruption every time. Founders love the word “disruption.” Customers hear something else: “Oh great, more homework.” Geoff points out how customers don’t adopt disruption as much as they adopt relief. If your product instantly removes pain, buyers don’t care whether it is revolutionary, incrementa...