Meetup CEO David Siegel: Five Things You Need To Be A Highly Effective Leader During Turbulent Times

An Interview With Charlie Katz

…The key was that we made a plan and made fast decisions, whether it was taking an MVP approach and iterating, listening to and communicating with our customers, or supporting our teams. This was all in an effort to enable amazing community experiences and keep people connected during this particularly challenging time. So far, it’s worked out exceptionally well with more than 1.5 million online Meetup events in nine months, which have connected more than 10 million people.

As part of my series about the “Five Things You Need To Be A Highly Effective Leader During Turbulent Times”, I had the pleasure of interviewing David Siegel, CEO of Meetup.

David was selected by both WeWork and Meetup’s founder to succeed him as CEO in 2018. He has quickly become a sought-after expert on community building. Prior to his role as CEO of Meetup, he was the CEO of Investopedia. He has more than 20 years of experience in growing revenue and profit in digital media, subscriptions, and e-commerce. He is a motivational leader with experience in mergers and acquisitions, turnarounds, scaling operations, and growing businesses in the post-startup phase. He is also an Adjunct Associate Professor of International and Public Affairs at Columbia University, and he earned his M.B.A. from The Wharton School.

Thank you so much for your time! I know that you are a very busy person. Our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’ and how you got started?

I value the power of community because I have lived it. Growing up in an Orthodox Jewish and religious household, community was a way of life. When there was a death, the entire Orthodox community gathered, bringing food to the bereaved family for many weeks, and visiting, what we refer to as sitting Shiva at their home. Community also meant joyous celebrations of marriages and births. These religious traditions date back thousands of years. As an adult, I have also found community through my children’s schools, through my career, and other avenues of life. Community has played an integral role throughout my life, and that is why Meetup speaks to my soul.

Meetup is a company focused on building community. Meetup understands that we become better people when we’re around other people and meeting in person.

Everything I’ve done and every job I’ve held has led me to this moment as CEO of Meetup. After business school, my first job was in technology as an early employee at DoubleClick, an adtech company that was eventually acquired by Google. I kept on that path working for a series of tech companies, and increasingly moved into larger leadership roles. At 1–800 Flowers, I ran mergers and acquisitions, strategic planning, and business development. I progressed to become the general manager and ran a number of different businesses for Everyday Health, a start-up digital health publisher that grew to have an IPO on the NYSE. I went on to become president of Seeking Alpha, a technology company focused on startups seeking financing. It was a natural progression to Investopedia, where I held my first CEO role. That was a fun ride where the company tripled its revenue over a three-year time period, and shareholders were happy for its sale to another company at a significantly higher valuation. It was around that time when I was approached by WeWork to lead Meetup and become their first outside CEO and take over for their founder, who led for 16 years. I consider myself incredibly fortunate to have this role and the opportunity to continue Meetup’s mission of building community.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lessons or ‘take aways’ you learned from that?

I’m not sure if I would use the word funniest, but when I started out I had no idea what “I wanted to be when I grew up.” In college, I was a liberal arts major. I studied philosophy, political science, and economics — hardly a directed future career. So, I decided to continue my education in hopes it would help me figure out what I wanted to do. Perhaps that was a mistake, perhaps not. I was still undecided so I thought consulting was the best path forward for me: it would be an opportunity to gain exposure to different fields and disciplines, and I thought that it could ultimately help me to make my career path decision. So I worked in consulting for two years and I guess it was a mistake in that I learned that I absolutely hated consulting.

I learned that I needed to be involved, to roll up my sleeves, and to not create binders or PowerPoint decks that never went anywhere. I learned the hard way that I enjoy the process of building. I like to actually help companies, help people, and build great products. Those actions can change people’s lives, similar to what has been done with Investopedia, Meetup, and 1–800 Flowers, and others. So perhaps it was a funny mistake to have chosen consulting because I realized how much I hated it, but mistakes can be great things because they also provide incredible life lessons and key takeaways.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story?

Sure, I am happy to do so. When I was first starting my post-consulting career, I went to work at my largest client, which was a company called DoubleClick. David Rosenblatt was the general manager of a business unit, and I was a human resources partner at that time. We worked together on figuring out different people-related strategies for the business. We met 20 years ago, and I still speak to him multiple times a year and even multiple times a week when I have a major career decision to make.

When I was back at DoubleClick I was making a tough career decision. I knew I wanted to move out of human resources. But I wasn’t sure whether to move to a business development opportunity I was offered at DoubleClick, which would succeed in getting me out of HR and into sales and business development, or to leave my job to pursue an MBA? At that time, my wife was pregnant with our first child. If I chose to pursue my MBA, we were going to go without income for three people for two years and would have to rely on our meager savings. In contrast to that, the business development role would have more than doubled my salary at the time.

Following David’s advice, I took the long-term approach. He had gone to business school and advised me that the education I would get from business school would be more valuable long-term than the increased short-term compensation. He was absolutely right. I look back very fondly on that decision.

There have been at least ten decisions throughout my career where he was the first person I called for advice. He’s currently on the board of Twitter and IAC and also the CEO of 1stDibs. More importantly, he remains an exceptional mentor, person, and friend.

Extensive research suggests that “purpose driven businesses” are more successful in many areas. When your company started, what was its vision, what was its purpose?

Meetup is the ultimate mission and purpose-driven company.

Meetup was founded in 2002, and was inspired by the tragedy of 9/11. The events of that day brought the community, and the country, together. Meetup founder, Scott Heiferman, lived in NYC during that time, and he saw strangers saying hello to each other and coming together to support each other. The response of his neighbors was his spark of inspiration for Meetup. He set out to build a platform that would introduce and connect people together over a common denominator — a shared interest, activity or goal.

Eighteen years later, Meetup remains steadfast to its mission of fostering human connections. Prior to the pandemic, nearly all Meetup events were held in person. In March of 2020 we began to encourage online Meetup events as a way to keep people connected while they needed it most. Already, over 10 million people have participated in more than 1.5 million online Meetup events.

Scott’s vision continues to guide our strategy. We measure key decisions based on how much we’re actually able to drive community connections for our 52 million members and our 200,000 organizers.

We know — and see — how great things happen when people come together over a common interest or activity. Human connections are vital to our happiness. We help people grow and achieve their goals through real-life, human connections. From professional networking, to online yoga and meditation, to coding workshops and more, people use Meetup to meet new people who share those same passions or professional aspirations.

Thank you for all that. Let’s now turn to the main focus of our discussion. Can you share with our readers a story from your own experience about how you lead your team during uncertain or difficult times?

When COVID-19 hit in March, our company evaluated our mission. Is our mission to get together in person? Or, is our mission to ensure that we keep communities and people connected to each other?

We realized that Meetup is about keeping people and communities connected. That was the moment that we said we have to build an online experience for Meetup — and we did, quickly.

Like most CEOs, founders and leaders, I sometimes struggle with when to direct and when to empower. The ideal scenario is to be as empowering as possible so other people make their own decisions. The risk is, empowering takes longer, and in a crisis situation, you need to be directive.

In the COVID-19 crisis, I was probably uncomfortably direct. We got the leadership team together and made a decision in a day. We had to make this pivot and do it quickly. This required taking people off their current projects to enable online events as quickly as we could. No engineers are happy in that situation. We had to be comfortable producing a minimal viable product (MVP), not an amazing experience but good enough, and then improve from there. We were quite direct but also apologetic about being direct. We explained the context and reason we were doing it.

Online events were up and running in four days. From there, it was another month, month-and-a-half of improvements. In nine months, we’ve had more than 1.5 million online Meetup events, and more than 10 million people have benefitted from those online Meetup events. We built it, and people came.

Did you ever consider giving up? Where did you get the motivation to continue through your challenges? What sustains your drive?

Personally, I have either an unhealthy or a healthy (I’m not exactly sure) perspective on one’s mortality. I am in tune with how fleeting, short, and how fast life is, and that we only live this one life. And, I’d like to have as great a positive impact on the world around us as I can. That perspective is one of my greatest motivators. To give up means that I’m giving up on the one life that I have. And, to give up on a business when you’re the CEO means you might as well leave being the CEO.

The CEO’s job is to lead and motivate teams, and to ensure the players on your team are focused and optimistic. That’s not something I could fake. So the moment that I would feel like giving up being a CEO is the moment that I would need to look for another job. In my past, I have decided to look for other jobs because I no longer had the same energy and motivation for it. Personally? I would quit before I would consider giving up because that’s kind of the same exact thing. You cannot fake being motivated, and you cannot fake being energized about the future of a company. And, thank God, I am both motivated and energized by the future of Meetup.

What would you say is the most critical role of a leader during challenging times?

My immediate instinct says that it’s optimism. To have and communicate optimism is an incredibly important role for a leader, especially during challenging times. However, if one is overly optimistic, which is a trait I struggle with because I am an overly optimistic person, then it doesn’t necessarily provide great leadership to an organization that is more dubious of its company’s future.

So I have come to learn that in business, optimism balanced with realism is the most critical characteristic for a leader to portray during challenging times. A leader has to be realistic, and acknowledge the business challenges that lie ahead. It’s about facing those challenges, and then discussing and coming up with creative solutions to then exceed those challenges.

Leaders need to provide the context of why something is challenging, and the optimism to know that every problem holds a solution. Leaders need to then identify all mitigating actions against those challenges. If you’re overly optimistic, that’s not healthy for an organization, and if you’re overly pessimistic that’s not healthy either. It’s finding the right balance between optimism and realism to acknowledge the challenges and find ways to move forward.

When the future seems so uncertain, what is the best way to boost morale? What can a leader do to inspire, motivate and engage their team?

The most important thing a leader can do in order to understand, inspire, motivate, and engage their teams, is to communicate. It requires communication in all of its forms. Often, people associate communication with oral communication, and it is that plus much more.

When I say communication, I mean that it’s important to document a strategy and lay it out for the company, and do so in a way that engages team members and employees in that company’s strategy by having them react to the documentation. That is a form of two-way communication. That’s critical. It’s not one-way; it’s got to be two-way communication realized through written communication.

Then, there’s oral communication. When you think about oral communication, it’s really thinking about every single 360 degree component. It’s making sure that you’re diligent about one-on-one meetings and having agendas with each person on the executive team, so that there are high levels of alignment on strategy. It’s making sure that you have skip-level meetings to gain input from those holding manager and director level roles, and having periodic check-ins with each individual at those levels because they’re the people whom most of your employees are looking to.

The most important form of communication, in terms of morale, is the relationship between a manager and their employees. People stay in companies because of the depth of their relationship to their manager. People leave when there’s a break in trust with their manager. The best thing a company can do for morale is to ensure that managers are that glue. They need to be highly informed about company strategy, and at the same time can effectively listen to the people on their teams and understand their challenges and transmit that information.

What is the best way to communicate difficult news to one’s team and customers?

The only way for a good leader to communicate difficult news is to be as honest and transparent as possible. I’d recommend providing the information in context. It requires acknowledging where faults may have been, taking ownership, sharing the difficult news, and checking back a few days later to make sure clarity and context around the difficult news are still understood.

Difficult conversations require multiple touchpoints. After the initial conversation, check back to take stock of the staff’s thoughts and feelings, and ensure that they understand the reason behind a decision. That check-in is underutilized and yet probably the most important thing a leader could do.

How can a leader make plans when the future is so unpredictable?

Because the future is so unpredictable, it is that much more important to have a plan. Our goal as leaders is to put a plan in place no matter what the future may hold. Wayne Gretzky, one of the best NHL players of all time, would identify where the puck is going and go. Similarly, a leader must make plans based on an understanding of where an organization and one’s customers are and figure out where you need to go, and how to get there.

Planning is crucial, along with a really thorough process to iterate on that plan. Never just set it and forget it. The magic is in putting together a series of hypotheses that may or may not be proven true, that then influence the ultimate plan. Then, to continually evaluate whether or not you have the right plan and be nimble to shift the plan as needed.

Over-communicate and share context with your team about why the plan shifted, otherwise you risk chaos and concern about ever-shifting priorities. Too often, I see organizations stay the course on a plan that should have been corrected. Leaders are afraid of the perception of changing a plan from their employees or board members. And then they dig themselves in deeper and deeper due to a reluctance to iterate.

To lead effectively you need to create a plan, iterate on it, and then over-communicate. Be upfront, and explain to all parties why that plan needed to change and provide context on how it is going to change. In uncertain times, the team needs to be told that the plan is flexible and to expect change. The only mistake is to keep a plan for plan’s sake, and not accept change where and when it is necessary.

Is there a “number one principle” that can help guide a company through the ups and downs of turbulent times?

Yeah, it’s never as bad as you think. And, it’s never as good as you think either. This is true from a company’s perspective, and it’s also true in life. There’s a thing that I like to say: there’s a reason why the words ‘organization’ and ‘organism’ have the same root. It’s because many of the principles that apply to understanding human psychology and human emotions apply directly to understanding organizational psychology and organizational emotions. Human organisms are complex and we tend to get overjoyed by the good and over-stressed by bad. Organizations do the same. Employees often see positive momentum as a sign that a business could be unstoppable and a downward trend as a need to potentially jump ship. It’s important to never get too excited about the good nor depressed by the bad. And the reality is, when people think they’re riding high because of enormous success, they may become egotistical — and, the same is true for organizations.

My guiding principle is to be humble during the good times, and optimistic during the challenging times. Maintain that balance. This may require actions that are contrary to natural instincts. Naturally, humans and organizations have an instinct to go to extremes. To say, ‘Wow, we’re killing it, now we’re unbeatable,’ and then to find out later how beatable they actually are. Or they think, ‘we have challenges and there’s no hope for the future,’ when in reality that approach will result in there being no future when the solution that will provide the solution will never be realized.

So, my number one principle is to remember that it is never as bad and never as good as one thinks. Maintain that healthy equilibrium. Stay away from extremes personally, professionally, and organizationally.

Can you share 3 or 4 of the most common mistakes you have seen other businesses make during difficult times? What should one keep in mind to avoid that?

Well, I guess I’ve been involved in so many challenging situations with different organizations, I’m going to give you five different mistakes that I have seen organizations make when they’re going through difficult times.

Number one: I’ve often seen organizations, and entrepreneur organizations are most egregiously at risk of doing this, scaling a business or a product before there’s product-market fit. Meaning, they start hiring lots of people and investing significant resources before they know that there are customers who actually want the product. Before bringing on overhead, make sure that there’s a deep product-market fit. What that means is that the market — meaning your customers — and the product solution are highly aligned. The product must solve a problem that customers actually face. Only scale after that happens. I think in difficult times, businesses jump to scaling, building, and changing too quickly, which gets us to challenge number two: People go to extremes in challenging times.

Business leaders may experience a lack of patience during challenging times. A common response, if it’s not working is to quickly give up and move to something else. In reality, they probably only needed to iterate on their plan and give it more time. When leaders go to extremes the perception by the employees is that leadership is just jumping from one thing to another. So number two mistake is to go too extreme in bad times and give up instead of understanding when more incrementality is actually required.

Number three, in bad times people will forget what a brand truly represents and where a business can move. They will say, “Oh my, look at this, we’re going through a challenging time, look at that company, look at the success they have, we should create a product just like that, and then we’ll have lots of success.” But if you’ve been doing something like Meetup has for 18 years, it’s not about saying, “Oh, we need to completely change what we do right now because other companies are having more success.” Instead, it’s understanding what your brand represents, and not losing sight of that. It’s thinking about what businesses and adjacencies you can go into, and what businesses may not be appropriate for a business to go into.

Mistake number four in challenging times happens when companies look to reduce costs. It is always a difficult decision to reduce costs. And oftentimes, that difficult decision results in not reducing enough costs. The mistake that I have made at times is in potentially being overly optimistic about figuring out how to cut expenses. And oftentimes, it is better to cut more expenses than you think in order to ensure that you don’t keep having to do so. There’s a real fear of reducing costs. But the greater fear is that the challenging times could end up lasting significantly longer and you’d have to do something that’s difficult again.

Lastly, it’s very easy for leaders to listen to the specific suggestions of what their teams might be saying to them, however, it is most important to understand what someone is trying to achieve with the suggestion rather than to take immediate action. This means, as a leader, it’s important not to provide teams with exactly what they want, but to ask, “what are you trying to accomplish with what you’re asking for?” Learn what they need most, and then discuss the right solution. Oftentimes, during difficult times, there may be a knee-jerk reaction to do whatever people want, and not be an island in decision making. I caution leaders to trust their gut and do what they think is absolutely in the best interest of the organization, always.

Generating new business, increasing your profits, or at least maintaining your financial stability can be challenging during good times, even more so during turbulent times. Can you share some of the strategies you use to keep forging ahead and not lose growth traction during a difficult economy?

The number one strategy is to focus. All too often, companies, leaders, and especially CEOs, have pet projects. They have people that they know want to work on specific projects. And it’s very hard to disappoint people who are working on projects that they’re excited about. But many times those projects are not the most important things to be working on during difficult times. And during difficult times the need for focus is much more important. This focus will allow people to get out of those difficult times sooner. It could be very popular to focus on a certain project, but not actually helpful to the company’s number one priority.

Secondly, make sure there’s a data-driven approach to decision making during difficult times. It’s very easy during great times to have qualitative feedback, and ask “what’s your opinion about this? What’s your opinion about that?” Letting data drive the decision-making during difficult times is critical because you may have fewer people on the team during that time. The need for focus is greater and therefore data is your number one ally.

Number three: Difficult times usually are riskier times. It’s okay to take on greater risk than one might be willing to do during more positive times. In positive times, when everything’s going great, you may be more risk-averse, and think, “I don’t want to make this big change, everything’s going great.” But I think you’d have a different assessment of how risk-averse you need to be during difficult times. A leader should be willing to take an action that might have really big positive consequences or some negative consequences, because that could enable the company to get out of that difficult time faster.

And lastly, it’s okay to say, “this is the right decision, and let me explain why it’s the right decision,” even if it means being a little bit more direct. Sometimes that’s more important than not being able to make decisions because too many people have differing opinions about what to do. During difficult times CEOs should not make decisions by democracy with full alignment on every decision. Being direct and offering directives at those tough times prevents inertia from setting into the organization.

To summarize, focus, take a data-driven approach, take more risks, and be willing to make quick decisions. Leadership skills during difficult times are critical to a company’s financial stability and business success.

Here is the primary question of our discussion. Based on your experience and success, what are the five most important things a business leader should do to lead effectively during uncertain and turbulent times? Please share a story or an example for each.

The most challenging time for Meetup has been due to the pandemic. We are a business built on in-person events. We quickly had to decide whether or not we were going to do something the company had never done before. Since 2002, Meetup was all about getting together in person. If Meetup organizers wanted to organize events that were only online, we used to suggest that they find another platform. It was that draconian. In March of 2020, Meetup made the decision that the company’s purpose was in keeping people connected and building community, while also being as safe as possible.

So we set our plan in place:

In early March, we made the decision to move Meetup events online within 48 hours of COVID-19 meaningfully hitting the US. We said we need to build an integrated online solution for our business. We didn’t have significant debates — we moved fast — and it paid off. We have had phenomenal results in terms of keeping our communities connected during this time.

Number two is taking an MVP (minimum viable product) approach to product planning. We accepted that we did not need to initially build the absolute best online events product out there, but we need to build a good enough product to allow our organizers to move their events online. We rolled out an online Meetup experience knowing that there were four to six different features we would have to iterate on, but we knew it would be better to get it out immediately than to aim for perfection.

The next action that we took is we had our research team and all of our product teams understand and listen to what customers were telling us around online Meetup events, and which features were most important. Listening to our customers (our members and to our organizers) on how we could best enable their success is the next item. We planned to support that rollout with significant amounts of communication and best practices sharing. To do that, we created templates on how to conduct online events, whether it’s a book club, yoga, or tech event.

We created a Meetup group called Meetup Live, where we shared advice for organizers and hosted workshops on how to transition the energy of an in-person Meetup event to online environments. 4,000 people attended our Meetup Live chat with an expert in Zoom. It was a great way to set up two-way communication between Meetup’s product team and our organizers and members. Meetup Live, produced by Meetup HQ, hosts two online Meetup events every single week helping organizers succeed in this transition due to COVID-19. We also launched a company blog called Community Matters. It educates our members and our organizers to succeed during this unique and special time when its more difficult to meet together in person.

The key was that we made a plan and made fast decisions, whether it was taking an MVP approach and iterating, listening to and communicating with our customers, or supporting our teams. This was all in an effort to enable amazing community experiences and keep people connected during this particularly challenging time. So far, it’s worked out exceptionally well with more than 1.5 million online Meetup events in nine months, which have connected more than 10 million people.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

Thomas Jefferson said, “I’m a great believer in luck, I find the harder I work, the more I have of it.”

I love that quote because there are many different ways someone can end up becoming fortunate or lucky, both professionally and personally. There are actions that you take, whether it’s getting out there and meeting interesting people, or making decisions to open up opportunities for yourself or your company. Then, there are people that frequently bemoan, at times, not being as fortunate. Perhaps your wiring as a pessimist or optimist leans into these ways of thinking. However, it’s important for each of us to realize that if we work really hard and seek out opportunities great things can happen. If you are presented with an opportunity and if you have the ability to do it, you should say yes. My recommendation is to not overthink things. That “yes” can turn into a life-changing opportunity that might never have happened. I can’t count the number of times I’ve said yes to things from meeting a certain person, to speaking at an event, or trying a new product, that have led to something that was enormously impactful to my life. I think by acknowledging that we create our own luck, armed with the knowledge that if you work really hard, you will end up having more of it, is something that’s incredibly empowering for me.

How can our readers further follow your work?

So nice of you to ask! I will be launching Meetup’s first podcast in January 2021 called “Keep Connected.” I will be speaking with the Meetup community of organizers and members, and perhaps we will have some superfans and special guests join us. We plan to dive into the treasure trove of real Meetup stories, and talk of the power of keeping and building human connections.

I’m particularly excited about this podcast because we will be interviewing some of the amazing organizers who have changed people’s lives. Spoiler alert: it’s going to be incredibly inspirational, but also very practical and real. It’s going to help people to figure out whether they want to be leaders in their communities, and how they can go about doing so. It will provide the motivation, and potentially the inspiration on how to be a community leader in the way that you can be the best you that you can be, and get the most out of your life.

I encourage your readers to follow me on Twitter @Davidmeirsiegel and to follow Meetup on Twitter, Facebook, Instagram, and LinkedIn. Guaranteed your readers will learn more about our company, the power of community, and about themselves.

Thank you so much for sharing these important insights. We wish you continued success and good health!

About The Interviewer: As Exec. Creative Director, Charlie Katz spearheads the full gamut of creative marketing for Bitbean Software Development in Lakewood, NJ. Charlie has over 20 years experience in major NY and west coast agencies, including Dancer-Fitzgerald-Sample, now Saatchi & Saatchi, D’Arcy-MacManus & Masius, and Wells, Rich Greene. Starting as a junior copywriter and moving up to Exec. Creative Director, he developed creative strategies and campaigns for such clients as Colgate, R.J. Reynolds, KFC, and Home Depot. Along the way he won numerous national and international awards including the NY Advertising Club ‘Andy’.