I recently went one-on-one with Chris Kelly, CEO of Upwave.
Adam: Thanks again for taking the time to share your advice. First things first, though, I am sure readers would love to learn more about you. How did you get here? What experiences, failures, setbacks, or challenges have been most instrumental to your growth?
Chris: Starting any company is always challenging. I haven’t heard of any startup that grew without their fair share of material setbacks! Upwave took a circuitous route to where we are. We started as a market research platform for small businesses, evolved to sell to brands, then stumbled into ad measurement. We survived lean years and near-death experiences. Fortunately, the team’s perseverance paid off, and we built a nice business with durable growth, sustainable profitability, and a happy customer base!
Adam: In your experience, what are the key steps to growing and scaling your business?
Chris: That depends on the business, and what you should focus on depends on your stage. But a common mistake is underappreciating the small steps in the early days. If you’ve worked at big companies, it may be difficult to get excited about a $100 sale. But the first $100 sale for a new business is exciting! It should be celebrated. It’s the proverbial first step in your thousand-mile startup journey.
Adam: What is your best advice on building, leading, and managing teams?
Chris: The only simple advice I have is treating employee satisfaction as a critical KPI. Seems obvious, but so many companies don’t do it. That means you formally track it, swim in the data, investigate root causes, and always be looking for ways to improve it. What makes one employee base happy and motivated may not work on another employee base. What matters is to genuinely care about their happiness and motivation.
Adam: What are the most important trends in technology that leaders should be aware of and understand? What should they understand about them?
Chris: Everyone probably expects an answer about AI to these questions. Perhaps that’s obviously what any leader should be paying attention to. What’s interesting for me to watch is how the cost of developing a digital product is falling to zero. The cost of a rough prototype done by AI is already zero. Does this mean every product or app that’s built will succeed? No. Taste is still king. So those who can clearly see a business problem, envision a solution, and tastefully design a user experience will win. And those folks no longer are gated by engineering resources to build their vision. That’s an exciting future.
Adam: What do you believe are the defining qualities of an effective leader?
Chris: I once heard the art of leadership is discernment. There are no universal rules: you have to know when to keep things simple vs. embrace complexity, when to stick to your principles vs. make reasonable exceptions, when to grind vs. recharge, when only the headline matters vs. the devil is in the details. And on and on. Better discernment wins.
Adam: How can leaders and aspiring leaders take their leadership skills to the next level?
Chris: Ben Hogan once said, “The secret is in the dirt.” You only get better at golf by playing golf, not with magic shortcuts. The same is probably true for organizational leadership; you get better by doing. I don’t think there are “silver bullet” books, although plenty of good ones can give you useful mental models. If you’re running a company, and you’re being introspective, you’ll get better at it.
Adam: What are your three best tips applicable to entrepreneurs, executives, and civic leaders?
Chris: Don’t get outworked. Repeat the important stuff. Be succinct.
Adam: What are your best tips on the topics of sales, marketing, and branding?
Chris: Watching videos of yourself do a sales pitch is powerful. Yes, we all hate the sound of our own voice. But you’ll see mistakes you didn’t realize during the call: when you overanswered, where you got rabbit-holed, where you rambled on, when you missed the body language of the prospect, etc. Also, when marketing your story, ensure everything you say ties back to your positioning.
Adam: What is the single best piece of advice you have ever received?
Chris: Take your work seriously, but never yourself.
