I recently went one on with David Siegel. David is the CEO of Meetup, the largest platform for finding and building the local community. Prior to joining Meetup, David was CEO of Investopedia, and before that, President of Seeking Alpha. David is also the author of the new book Decide and Conquer.

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? 

David: Wow. There is a lot in that question. How did I get here? I came from a wonderful family with two loving and encouraging parents. I have no doubt that this strong upbringing helped to build the psychological, emotional, and mental foundation for my future success. So I owe everything to my parents.

From a career standpoint, I was fortunate to be an early employee in one of the top internet companies in New York City: DoubleClick. Having early digital experience then propelled my career. After earning my MBA I became a director at a $2 billion pharmacy chain. After that, I became a VP and then a Senior VP at 1-800-Flowers. Later, became the President of a major financial publisher, Seeking Alpha. Then, at 40 years old, I became CEO of Investopedia, the world’s largest financial education website. We were able to more than triple the company’s revenue in three years and increase its valuation by five times before selling it. In late 2018, I became CEO of Meetup, which was owned by WeWork at the time. The experience of leading a company under WeWork and adapting a company that was all about in-person connections during a pandemic led me to write a book, Decide & Conquer, which is coming out on March 8, 2022. A final passion of mine is teaching. I have been teaching entrepreneurship and strategic planning for six years as an adjunct professor at Columbia University. 

Adam: In your experience, what have been the key steps to growing and scaling your businesses? 

David: Growth is about understanding the needs of a business. You must decide whether a greater focus on a company’s core function will drive success or whether growth can best be derived from expansion into other channels. I’ve seen both strategies succeed and both fail. The key step is to understand whether more focus or more channel expansion is the path to growth. At Investopedia, the company was actually too focused on its core service. It stuck to being a financial dictionary for many years and didn’t realize how many opportunities there were to expand. We built an e-commerce business, a lead generation business, expanded advertising opportunities, and revenue grew dramatically. Conversely, when I started at Meetup the company was taking on far too many different projects. It needed to focus back on its core business to drive a better customer experience and future growth. Understanding this one question is critical for future success. 

Adam: In your view, what is the future of the workplace? What are the key trends that leaders should be aware of and understand? 

David: Since people always seem to like chunking their answers in three parts, let’s do that now.

1. Hybrid workplaces are the future. The days of employees working in the office five days a week (unless it is preferred by an employee) are dead. Most companies, and tech companies and startups in particular are going to be hiring a majority of their workers outside of their main headquarters’ metro areas. This is a huge win for remote workers. Remote employees used to have greater difficulty being a part of the company culture, getting promoted and recognized. That will forever change as more people work only one to three days a week in an office.

2. The workplace is going to be more about meetings, conference space, and collaboration and far less about set desks. We have gone from offices to cubicles to small six-foot spaces. I predict the norm will be to have flexible, non-dedicated workspaces for most employees. People will work where they want, when they want, and often on what they want. Because of the great resignation, there are a plethora of open jobs and too few people to fill them. Workers have far more power than they have had in decades.

3. The last trend is transparency. Employees are expecting their leaders to be far more transparent than ever before. That means sharing company financials, company strategy, and in some cases, greater compensation and benefits transparency. That greater transparency drives trust. Trust is the foundation for the employee-leadership relationship.

Adam: How can leaders build winning cultures in remote and hybrid settings?

David: This is a great question, it is one so many companies are struggling with, including Meetup. We didn’t renew our office space in 2020 and although we are about to move into a new space this spring, for the last two years we have had no office. At the same time, Meetup is all about building community. So we needed to find ways to build community outside of a traditional office. We launched an event called Meetupdate. Once a month we ask our NY-based employees to attend an in-person half-day gathering. The first portion of the gathering is an all-hands hybrid meeting, followed by a lunch, with the rest of the day dedicated to collaborating. There is room for everyone and plenty of space for holding meetings either outside (weather permitting) or indoors. 

While getting together IRL (in real life) once a month isn’t a substitute for daily or weekly in-person interaction, it helps a ton. We also gave a budget to every leader in the company and asked—and in some cases actually told—leaders that they needed to use the budget for team meetings, team offsites, and fun activities. We have had many teams organize some creative Zoom events, but generally, we are pushing our teams to organize as much as they can in person, at times when it has felt safe to do so, as there is nothing like in-person collaboration.

Adam: What do you believe are the defining qualities of an effective leader? How can leaders and aspiring leaders take their leadership skills to the next level? 

David: I’ll highlight two qualities, just to get out of that paradigm of always giving three examples.

First, what makes a great leader is the exact same thing that makes a strong person: being unselfish and empathetic. You simply can’t lead if you are unable to appreciate what challenges individuals have gone through, what their motivations are, and how they became the person they are. Being a great leader isn’t any different than being a great spouse, parent, friend. Empathy and selflessness are both as critical to leadership as they are to all aspects of one's life.

But—and this is a big but—being empathetic and selfless is necessary but not sufficient for being a strong leader. What separates great leaders from others is being a great decision-maker. Leaders literally make hundreds of decisions every day. Even not making a decision when presented with information is a decision. The core of my book, Decide & Conquer, is a framework for helping leaders to make smarter decisions in their personal and professional lives. I cover decisions that remove biases like the status quo bias, hindsight bias, recency bias, and others. The book also describes decisions where you recognize your personal incentives and biases and work to remove them from the equation. Great leaders lead by making smart decisions that impact the lives of their people.

Adam: What are your three best tips applicable to entrepreneurs, executives and civic leaders? 

David: Well, we are back to three again. No problem!

One. Be kind. When making decisions, understand that your reputation will follow you everywhere you go. The nature of being a leader is that many people won’t be able to fully understand the rationale (although you should still try!) for making a decision. But there is also a huge difference between being nice and being kind. Being nice, so as not to upset anyone, may not be kind. Sometimes the kindest thing you can do can be painful for someone. Strong leaders can’t always be nice, but they can be kind. This is a mistake I have made too often in the past.

Two. Speaking of mistakes, own your mistakes. The days when leaders need to seem superhuman are over. People expect to know about the failures that leaders make and the learnings that follow. I’m personally looking to hire leaders who are fully accountable for their mistakes. Leaders who are defensive and blame others instead of themselves will never be able to grow nor will they engender the trust and respect that is critical for leadership today.

Three. Your job as a leader is to eliminate surprises. Your employees shouldn’t be surprised, nor should your board. That takes a significant amount of communication about sensitive topics that often can lead to heated dialogues. I’ve personally been surprised many times in my professional life. Once, I was a CEO of a company and our parent company sold the company without telling me. Another time, I was surprised at being asked to cut my team by 50%. I’ve been fired and completely surprised. As a leader, your job is to ensure that no one around you is ever surprised. Provide clear goals, status updates, and honesty to all those you trust. And if you can’t trust someone, they shouldn't be on your team.

Adam: What is your best advice on building, leading and managing teams?

David: Work for your employees. Think about an organizational chart as upside-down. As CEO, you are at the bottom of the chart and your job is to enable everyone above you to succeed. If every one of your executives is successful and each leader enables the managers to succeed, and managers help individual contributors to win, then as CEO, you’re killing it. Find the right balance between empowering and driving to support the team. You can’t solely empower teams, or they will be going in opposite directions. The best support you can give is often very clear direction. Focus that direction on the what and the why but not on the how. Leave the how up to the team.

Adam: What are your best tips on the topics of sales, marketing and branding? 

David: Anyone that tells you they know the secrets of sales or marketing is full of it. There really are no tips. Greatness in sales and marketing is a tremendous amount of work. It means truly understanding your customers’ needs, developing a very catered pitch to those specific goals, and being able to show clear alignment between your product or service offering and a client’s goals. Sounds easy. It isn't. Too often great sellers close deals, but there is misalignment between what the client was looking for and the solution provided. Ultimately, the client leaves and now you have to make up the next year for that lost revenue. Great sellers are great communicators and great listeners. Not great convincers.

Adam: What is the single best piece of advice you have ever received?

David: The best advice I think just goes back to a philosopher named Hillel from the Talmud. Treat others the way you would want to be treated. Like I’ve talked about earlier: focus on being a transparent leader, be kind, understand your decision-making biases, try to eliminate surprises for those around you, and know when you need to be directive not just empowering. Look back to those early years out of college, think about that person, and treat your employees in a way that you would have wanted back in the day.

Adam: Is there anything else you would like to share?

David: I really enjoyed the opportunity to share my thoughts. You can reach me at david@meetup.com and I would be happy to hear from you! Be sure to check out Meetup.com or download our app on The App Store or Google Play. There are incredible communities there for everyone and you can find your people and build meaningful friendships.


Adam Mendler is the CEO of The Veloz Group, where he co-founded and oversees ventures across a wide variety of industries. Adam is also the creator and host of the business and leadership podcast Thirty Minute Mentors, where he goes one on one with America's most successful people - Fortune 500 CEOs, founders of household name companies, Hall of Fame and Olympic gold medal winning athletes, political and military leaders - for intimate half-hour conversations each week. Adam has written extensively on leadership, management, entrepreneurship, marketing and sales, having authored over 70 articles published in major media outlets including Forbes, Inc. and HuffPost, and has conducted more than 500 one on one interviews with America’s top leaders through his collective media projects. A top leadership speaker, Adam draws upon his insights building and leading businesses and interviewing hundreds of America's top leaders as a top keynote speaker to businesses, universities and non-profit organizations.

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