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From Uncertainty to Leadership: David Siegel’s Journey Through Tech and Beyond
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DoubleClick was just—wow. You know how people talk about the famous PayPal Mafia, with Elon Musk, Peter Thiel, and others? Well, in the New York tech scene, DoubleClick had its own version of that. Over 200 CEOs and presidents of tech companies came out of the early days of DoubleClick. (David Siegel)
(00:00-04:44)
David reflects on a pivotal moment during his college years when he attended a conference at Princeton and sought career advice. A mentor suggested that if he had no idea what he wanted to do, consulting would be the best option. The reasoning? Consultants get to explore different industries without needing deep expertise upfront. Intrigued, David decided to follow this advice and landed an internship with the management consulting firm William Mercer while still in school.
After graduating from the University of Pennsylvania, he continued in consulting, specifically in merger and acquisition (M&A) integration. His work involved helping companies decide what to keep and what to cut post-acquisition—a role that offered him a front-row seat to major corporate transformations.
During his time in consulting, David worked closely with DoubleClick, a dominant player in online advertising at the time. The company was later acquired by Google, but in its early days, it was a powerhouse in the New York tech scene—akin to what OpenAI represents today in AI.
His career took a sharp turn when DoubleClick’s CEO, Kevin Ryan, approached him with a direct question:
"How much are you making as a consultant?"
At the time, David’s salary was $40,000 per year—a solid starting wage for a recent graduate. However, Ryan revealed that DoubleClick was paying six times that amount for his consulting services. To cut costs while benefiting both sides, he offered to double David’s salary if he joined the company directly. The deal was too good to pass up, and just like that, David left consulting and stepped into the fast-paced world of tech.
David describes DoubleClick as a hub of future tech executives. Much like the famous "PayPal Mafia," which produced leaders like Elon Musk and Peter Thiel, DoubleClick became a breeding ground for high-level tech talent. Many of its early employees went on to become CEOs and presidents of major companies.
Among them was Neal Mohan, who is now the CEO of YouTube. David and Neal not only worked together but also formed a personal connection—one that extended beyond the workplace. In a humorous anecdote, David reveals that he played matchmaker for Neal, introducing him to his future wife. At their wedding, David and a friend even received a standing ovation for making the introduction, cementing his reputation as a successful matchmaker—or, as Alex jokingly puts it, an "Indian auntie."
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From Tech Titans to Financial Wisdom: David Siegel’s Take on Leadership and Community
If you're interested in equity research but don't want to pay tens of thousands of dollars for Bloomberg or FactSet, Seeking Alpha offers an impressive level of research in its articles. But what’s even more impressive is the thoughtful comments, debates, and disagreements in the discussion sections. I always encourage people to read the comments—it’s almost like a Talmudic debate playing out in real time. (David Siegel)
(04:44-10:59)
Alex kicks off the conversation by joking that if any listeners are single, they should connect with David Siegel—who has successfully set up three marriages and is working on a fourth. But beyond matchmaking, David shares how professional relationships have shaped his career.
One key figure in his journey is Kevin Ryan, the legendary entrepreneur behind companies like MongoDB, Business Insider, and Zola. David first met Ryan during his time at DoubleClick, where he got an inside look at New York’s growing tech ecosystem. Years later, when David led a management buyout of Meetup from WeWork, Kevin Ryan was the first person he called—proof that strong connections can come full circle.
The conversation then shifts to David’s time at Seeking Alpha and Investopedia, two platforms that revolutionized how people access financial insights.
Seeking Alpha, in particular, stood out because of its comments section—something David calls the platform’s “secret sauce.” Instead of the usual internet snark, Seeking Alpha fostered deep discussions about stock analysis, attracting professionals and serious investors who debated investment strategies in a way that felt almost scholarly. Alex even jokes that it’s “the Torah of finance.”
David explains how Seeking Alpha built this high-quality community:
- It relied on a network of 5,000-10,000 contributors, not traditional journalists.
- Writers were often professionals or passionate investors rather than media insiders.
- The best discussions happened between the contributors themselves, raising the level of conversation.
- A paywall helped filter out less serious participants, ensuring that those who remained were truly invested in the discussions.
This approach made Seeking Alpha more than just a financial news site—it became a trusted hub for investors looking for well-researched insights without paying thousands for Bloomberg or FactSet.
Playing Hard to Get—The Art of Deals, Leadership, and Lessons from WeWork
I said, "We’re not for sale." Then we met a second time, and I said, "We’re not for sale." Then the IAC head of M&A, a guy named Mark Stein, calls me up and says, "Okay, I get it, I get it. Seeking Alpha isn’t for sale. But, David, are you for sale?"
So I said, "I’m for sale."
And he goes, "Okay, this is what we’d like to pay to have you become the CEO of Investopedia and take over the company." That’s how I ended up at IAC and Investopedia. (David Siegel)
(10:59-15:03)
David shares the behind-the-scenes story of how he went from President of Seeking Alpha to CEO of Investopedia. It all started when IAC, a media giant owning brands like Match.com and HomeAdvisor, wanted to acquire Seeking Alpha. But David and his team played it smart.
His strategy? Always say, "We’re not for sale."
- This approach makes a company more desirable.
- It gives the seller more negotiating power.
- It can even lead to unexpected opportunities.
IAC eventually gave up on buying Seeking Alpha, but they had another idea. Their head of M&A called David and asked, "Okay, Seeking Alpha isn’t for sale. But are you?"
David’s answer? "I’m for sale."
That’s how he became CEO of Investopedia. Under his leadership, the company grew from about $10 million in revenue to nearly $40 million, making it a major success before it was sold.
Next, the conversation shifts to WeWork. Alex jokes about having a WeWork mug, and David recalls his time there—before the company’s infamous collapse.
Despite WeWork’s high-profile troubles, David believes it’s unfair to dismiss everything they built:
- They created a billion-dollar business (even if it wasn’t the $47 billion valuation they once claimed).
- They understood the power of community and in-person collaboration.
- They made flexible office spaces mainstream.
Of course, there were big mistakes, too—like setting unrealistic expectations and chasing growth at all costs. But even from failure, there are valuable lessons.
Building Connections: The Power of Community and the Lessons from WeWork and Meetup
For most people—especially millennials and Gen Zers—they’re not just looking to work and get a paycheck; they want to feel like they’re having a positive impact on the world. Finding a way to show how your company is truly improving the quality of life for others is something WeWork did exceptionally well, and I think a lot of CEOs can learn from that. (David Siegel)
(15:03-21:20)
David Siegel reflects on his time at WeWork, a company that became known for its bold goals and unique culture. He shares how WeWork’s leadership was exceptional in its ability to attract top-tier talent, both at the executive level and throughout the organization. The company’s ambition and drive pushed its employees to rethink what was possible and aim for bigger goals than they might have considered on their own.
One of the key elements of WeWork’s success was its culture of pushing for higher goals. This ambition was not just about growing numbers or revenue; it was about creating an environment where everyone felt empowered to reach beyond their initial expectations. For David, this cultural influence even affected his leadership approach at Meetup, where he was the CEO. The WeWork culture taught him the importance of setting big, bold goals that stretched what seemed possible. This constant push to aim higher became a defining characteristic of his leadership style, and it influenced the culture at Meetup as well.
David points out that WeWork’s cultural influence didn’t just make companies more ambitious. It also encouraged an “all-in” mentality where employees were not just looking for a paycheck—they were motivated by a sense of purpose and the idea that they were contributing to something much bigger than themselves. This mission-driven culture was something that David admired about WeWork and worked to bring to his own company, Meetup.
David highlights another key element of WeWork’s success: its ability to make employees feel like they were part of something bigger than themselves. At WeWork, employees weren’t just focused on the next big project or milestone—they were driven by the company’s mission to change the way people work and live. This sense of purpose was incredibly motivating for staff, particularly those from younger generations like Millennials and Gen Z, who crave meaningful work that positively impacts the world.
David also emphasizes that WeWork’s mission-oriented approach wasn’t just about lofty goals or grand speeches; it had practical, day-to-day applications. Employees were encouraged to see how their work contributed to a larger societal change, which helped them feel a deeper connection to the company's purpose.
Shifting gears, the conversation moves to Meetup, a platform David led with a mission to combat loneliness by fostering in-person connections. David talks about the startling statistics around loneliness, sharing that the U.S. Surgeon General recently pointed out that loneliness is now a public health epidemic that can be more dangerous than smoking two packs of cigarettes a day. With more than 40% of people regularly feeling lonely, and the situation being especially acute among young people in larger cities, David stresses the need to address this issue.
The core mission of Meetup was to get people off of technology and back into real, face-to-face interactions, which David believes is essential for mental and emotional well-being. The company’s goal was to use technology to encourage human connection in a world that is becoming more digitally driven. For young people, in particular, developing meaningful in-person relationships was crucial for brain development and overall health.
David talks about a lesson he learned throughout his years at Meetup: Humans are social creatures by nature, and we are hardwired for community. He explains that our survival as a species in prehistoric times relied on being part of a group, whether it was for hunting, gathering, or mutual protection. Over time, humans have maintained a deep-seated need for connection and belonging. When that connection is lost or diminished, it leads to serious consequences, such as depression, anxiety, and even self-harm. David shares that one of his biggest takeaways from working at Meetup was realizing how essential it is for people to feel connected to others.
David reflects on the personal impact of community and how he has seen Meetup change people's lives for the better. He shares stories of people who found support groups, friends, or even lifelong partners through Meetup. One particularly moving example was of an individual in the LGBTQ+ community who struggled with coming out but found a supportive group through Meetup that helped them navigate the process. This is just one example of how Meetup’s platform has been a lifeline for many people, helping them find their “people”, deal with life challenges, and build meaningful relationships.
David recalls hearing dozens of stories from Meetup users who claimed that the platform literally saved their lives. The impact was particularly profound for people in marginalized communities or those going through difficult life events. One story that stands out is of a person who, after being diagnosed with breast cancer, found a support group through Meetup where they could connect with others facing the same challenges. David also emphasizes how the Meetup community has supported people through mental health struggles, providing them with a sense of belonging and the resources they needed to cope.
One of the most surprising aspects of Meetup’s impact was the number of marriages that resulted from people meeting through the platform. David laughs as Alex jokes about how many people David could be credited with bringing together, but it’s clear that Meetup’s ability to facilitate real, human connections is one of its most significant successes.
The Power of Connection: How Authenticity Drives Community and Success
They’re afraid to be vulnerable. They’re afraid to be themselves. They think, “If 100 people say it and one person is upset, it’s not worth it.” But forget the one person. The 99 others will find it much more interesting. You’ve got to be yourself. If you try to satisfy everyone, the content will suck. (David Siegel)
(21:20-26:58)
David kicks things off by discussing the vital role of community in our lives. He recalls the countless instances where people walked up to him during his travels for Meetup events, sharing how the platform helped them find spouses, secure jobs, or meet lifelong friends. For David, these stories reinforce how powerful it is to bring people together in real-life experiences, despite the rise of digital communication.
He passionately talks about how Meetup’s mission was centered around combating loneliness—a global epidemic that affects millions, especially among young people. With studies showing that loneliness is more dangerous than smoking, David emphasizes how vital it is for people to feel part of a group or community. In fact, one of the most impactful aspects of Meetup was its ability to create support groups, from LGBTQ+ communities to health-related meetups, helping people find others who understood their struggles.
He also touches on how technology, which is often blamed for isolating people, can be a tool for fostering community when used correctly. Meetup, through its platform, enabled people to connect with others offline, allowing them to feel a sense of belonging—a critical part of human existence. David believes the DNA of humanity is built for community, dating back to the days of our Paleolithic ancestors who survived through cooperation within groups. Disconnecting from this natural state of togetherness leads to negative mental health outcomes, like depression and anxiety.
Another central theme David discusses is the importance of being authentic when connecting with others. He explains that often, people separate their personal and professional lives, thinking they have to act differently in each domain. However, he stresses that authenticity is what truly builds successful connections in both spaces. People who show up as their true selves, whether in a career networking group or a social meetup, create the strongest and most meaningful relationships.
David shares a personal example of a Meetup organizer who ran two very different groups—a bowling group and a career networking group. Despite their different purposes, the organizer ended up getting two jobs through the bowling group and even made a best friend in the professional networking group. This highlights the overlap between personal and professional lives and how authenticity leads to unexpected, positive outcomes in both areas.
For David, this underscores the point that genuine connections are more valuable than any superficial interaction. Whether looking for a job, a romantic partner, or simply new friends, being yourself is what drives success.
The conversation also touches on the importance of human-centered communication, particularly in the B2B world. Alex points out that, despite the rise of AI and automation, business is still human-to-human (H2H). Yet, in B2B environments, people often forget this simple truth. The content in this space tends to become sterile and lifeless, making it harder for people to connect with the message. Alex explains that businesses often focus on facts and figures, but fail to infuse personality and real human stories, which makes the content more engaging and relatable.
David agrees, noting that people often hesitate to be vulnerable or authentic, especially in business contexts. The fear of offending one person can prevent the majority from benefiting from the message. But David believes that authentic content, even if it’s bold or risky, will always resonate with the right audience. The key is to stay true to who you are—whether you’re writing a business proposal, giving a presentation, or even posting on social media.
As the conversation moves into the topic of decision-making and leadership, David talks about his book, Decide and Conquer. He explains that the key to making successful decisions lies in understanding that failure is part of the process. It’s not about making perfect choices every time but about learning and growing from each decision, even when things don’t go as planned. He humorously refers to himself as more of a “decide and fail” type of person, emphasizing that it’s all about trying, learning, and then conquering.
Alex and David also touch on the fact that, in today’s rapidly evolving world, particularly with the rise of AI, communication and business experiences are changing. Despite these technological shifts, David argues that certain things remain the same—like the importance of genuine connection and authenticity in all forms of communication, both personal and professional.
The Risks of Inaction and How Decisiveness Drives Success
I started a tech mission to Israel, thinking I’d bring five, six, or seven people. We ended up bringing 65, with a huge number of tech executives—Reed Raymond from Apollo, the CFO of Warby Parker, and big names from venture capital firms, millions of dollars in investment from firms, investing in Israeli companies. (David Siegel)
(26:58-34:37)
David kicks things off by discussing the vital role of community in our lives. He recalls the countless instances where people walked up to him during his travels for Meetup events, sharing how the platform helped them find spouses, secure jobs, or meet lifelong friends. For David, these stories reinforce how powerful it is to bring people together in real-life experiences, despite the rise of digital communication.
He passionately talks about how Meetup’s mission was centered around combating loneliness—a global epidemic that affects millions, especially among young people. With studies showing that loneliness is more dangerous than smoking, David emphasizes how vital it is for people to feel part of a group or community. In fact, one of the most impactful aspects of Meetup was its ability to create support groups, from LGBTQ+ communities to health-related meetups, helping people find others who understood their struggles.
He also touches on how technology, which is often blamed for isolating people, can be a tool for fostering community when used correctly. Meetup, through its platform, enabled people to connect with others offline, allowing them to feel a sense of belonging—a critical part of human existence. David believes the DNA of humanity is built for community, dating back to the days of our Paleolithic ancestors who survived through cooperation within groups. Disconnecting from this natural state of togetherness leads to negative mental health outcomes, like depression and anxiety.
Another central theme David discusses is the importance of being authentic when connecting with others. He explains that often, people separate their personal and professional lives, thinking they have to act differently in each domain. However, he stresses that authenticity is what truly builds successful connections in both spaces. People who show up as their true selves, whether in a career networking group or a social meetup, create the strongest and most meaningful relationships.
David shares a personal example of a Meetup organizer who ran two very different groups—a bowling group and a career networking group. Despite their different purposes, the organizer ended up getting two jobs through the bowling group and even made a best friend in the professional networking group. This highlights the overlap between personal and professional lives and how authenticity leads to unexpected, positive outcomes in both areas.
For David, this underscores the point that genuine connections are more valuable than any superficial interaction. Whether looking for a job, a romantic partner, or simply new friends, being yourself is what drives success.
The conversation also touches on the importance of human-centered communication, particularly in the B2B world. Alex points out that, despite the rise of AI and automation, business is still human-to-human (H2H). Yet, in B2B environments, people often forget this simple truth. The content in this space tends to become sterile and lifeless, making it harder for people to connect with the message. Alex explains that businesses often focus on facts and figures, but fail to infuse personality and real human stories, which makes the content more engaging and relatable.
David agrees, noting that people often hesitate to be vulnerable or authentic, especially in business contexts. The fear of offending one person can prevent the majority from benefiting from the message. But David believes that authentic content, even if it’s bold or risky, will always resonate with the right audience. The key is to stay true to who you are—whether you’re writing a business proposal, giving a presentation, or even posting on social media.
As the conversation moves into the topic of decision-making and leadership, David talks about his book, Decide and Conquer. He explains that the key to making successful decisions lies in understanding that failure is part of the process. It’s not about making perfect choices every time but about learning and growing from each decision, even when things don’t go as planned. He humorously refers to himself as more of a “decide and fail” type of person, emphasizing that it’s all about trying, learning, and then conquering.
Alex and David also touch on the fact that, in today’s rapidly evolving world, particularly with the rise of AI, communication and business experiences are changing. Despite these technological shifts, David argues that certain things remain the same—like the importance of genuine connection and authenticity in all forms of communication, both personal and professional.
Check the episode's Transcript (AI-generated) HERE.
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Author
Experience-focused Leaders is the #1 Multimedia Podcast! We talk to senior business & tech leaders about the experiences that move forward organizations, customers and society at large. True to form, we mix audio, video, web and eBook formats to turn these authentic conversations into personalized nuggets you'll remember & use.
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