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Success By The Numbers: An Interview With Investopedia CEO David Siegel

This article is more than 8 years old.

David Siegel is a nice CEO. Like, almost unsettlingly winsome. Appointed last year to run Investopedia, you'd expect this Wharton grad who held senior roles at 1800Flowers and Duane Reade in his twenties, became President of a financial media company in his thirties and now runs a premium brand within IAC to be a lot more, well, ruthless. Instead he is one of the most charming and unpretentious CEOs I've had the pleasure to sit down with.

I was fortunate enough to spend the day with David and discuss a range of topics, from his thoughts on entrepreneurship, to the changing financial media landscape, to what he means by "nice aggressiveness".

Dan Simon: You're a youthful CEO and you were an even more youthful President at your last firm, Seeking Alpha. When most people think youthful CEO they think first-time company founder, not professional CEO.  What's enabled you to get to such senior roles so quickly?

David Siegel: More than anything - luck! I was blessed to have started working at DoubleClick in the late 90's. The digital media industry was nascent and DoubleClick was growing dramatically. They made some fast promotions, including making me a Director at 25, when most other Directors were in their mid-30's. My career has been more "normal" after that quick jump. VP at 30, SVP at 34, President at 38 and CEO at 40. Speaking of DoubleClick, there are now over 50 CEOs who have come from the company's early days. It is a great club to be a part of and was critical to my career.

Simon: Ok, but I think readers want to know what they can do to go further faster. Luck is great but not easy to replicate. Would you say there is some kind of attitude or trait that particularly helped you along the way?

Siegel: Well, the character trait I often talk about with my employees is “Nice aggressiveness”. I always just started taking on more responsibility very quickly. I never asked for more work, I just started doing it. Oftentimes employees ask me, “How can I get promoted?” The answer is, start doing the role you want to be promoted into and the promotion will be inevitable. Don’t ask for permission, just start doing it. But, do it in a way that supports others’ efforts and demonstrates a real partnership.

Simon: You've led two big brands in finance but which are both, headcount wise, relatively small, scrappy firms. Do you approach the business with the mindset of a professional CEO or more as an underdog entrepreneur?

Siegel: Definitely entrepreneur. Both companies have about 80-100 employees. This is the critical stage when you either stay "hungry and entrepreneurial" or you start building out processes, layers and bureaucracy. Entrepreneurship is key. Making decisions quickly, implementing minimum viable products, iterating, making mistakes, fixing them - rinse, wash and repeat. I once worked for a $2 Billion Revenue company. Very professional CEO. I was miserable. The best professional CEO is someone who makes his employees feel like underdog entrepreneurs.

Simon: What appealed to you about the financial industry and the financial news and information industry in particular?

Siegel: Our personal finance and investing decisions dramatically change our lives - for good and bad. Fights related to money are the 2nd most common cause of divorce. Millennials who want to start families are pushing them off for many years under the stress of massive student loan debt. Poor investing decisions are making retirement difficult for millions. Sadly, the U.S. is one of the lowest financially literate nations of major world economies. If we can change the industry at Investopedia and make people smarter savers and investors, we'll change people's lives. I can't think of anything more exciting than that. So, for me, it is all about having an impact on people’s lives.

Simon:  There's a lot of changes taking place inside the media industry right now and Investopedia and Seeking Alpha seem both to be part of that change. Any (concise) predictions about how the future of financial data and information will be consumed in the future?

Siegel:  The future is already here. People want to hear more from individuals who have true "skin in the game" and are experts in their field vs. the traditional journalism model. Social media has proven the power of the distributed content creation and users' preferences for it. In Seeking Alpha's case, that means content written by their thousands of buy-side experts. At Investopedia, it is our growing network of Financial Advisors and revamped editorial strategy. Financial data and information will be about helping to build a bridge between these true experts and users. Finance is simply following the path of Ebay, Shutterstock, Uber, Yelp, Twitter and countless others, where a "curated" crowd-driven platform is of greatest value to consumers.

Simon: Having talked to people who've worked with you, you seem to place a lot of emphasis on company culture and HR. To an outsider - given you're in the data-driven world of finance - this focus on the 'soft stuff' might seem strange. Why does it matter?

Siegel: Most people don't know this, but I started my career in Human Resources. It is pretty uncommon to go from HR to CEO, and that is unfortunate - since the function most related to the day-to-day work of a CEO is HR. Hiring the right people. Developing talent. Ensuring an optimal organizational structure. Interviewing. Persuading. Motivating. Building a great culture. Business isn't about an idea. It isn't even about the product. Both can become irrelevant quickly. It is about the people with those ideas who build those products. Without the right people who love what they are doing, you are dead. Dead. With great people, you attract other great people and keep on winning.

Simon: Any best practices on building strong and distinct corporate cultures?

Siegel: It must start with the CEO and the management team. If an employee says that a company's culture is terrible, that is just another way of saying that the CEO and management are terrible. There is no difference between culture and leadership. So, start at the top. I have fired leaders who are very capable, but are not focused on building the right culture. It isn't about IQ, it is about EQ. Employees spend more of their time with each other than with their spouses or children. If a CEO is not focused on building a distinct culture then they will build a very undistinct company. We currently have an all-hands "7 Minutes in Investopedia Heaven" weekly meetings, a Kegorator, weekly employee relay race tournaments and an arcade game with over 500 games. The details however matter a lot less than keeping an unwavering focus on culture.

Simon: Millennials are the most entrepreneurial generation in history. I think many are turning away from what they see as the corporate life and towards entrepreneurship or they're conflicted about which path to choose. Care to make a case for the business school and corporate route, the 'intrapreneurial' route you exemplify?

Siegel: Sure. I'm teaching an Entrepreneurship & Venture Initiation class at Pace University this Spring. I've had many conversations with my millennial students about the value of working first and becoming an entrepreneur later. There are 3 key arguments:

  • One, make mistakes on someone else's dime before you're on your own.
  • Two, there is huge value to networking and building relationships with colleagues who can be entrepreneurial partners in the future.
  • Three, if working allows an individual to save dollars and be less beholden to outside investors, then the entrepreneur will maintain greater autonomy - which is at the core of nearly every entrepreneur's motivations. The best path for an Entrepreneur is to work as an Intrapeneur, within a company, with the right culture that is aligned with his or her priorities.

Simon: If you could offer your younger (say 22 year old) self three pieces of advice what would you say?

Siegel:

  • I'd first say - "Surprise! You still have most of your hair"...Ok, first, although I went to the University of Pennsylvania for undergrad and Wharton for business school, I really didn't focus on learning. They were "stepping stones”. I wish I prioritized learning over grades by taking the classes I was really interested in instead of those that were easiest.
  • Secondly, I was always worried about making enough salary to support my wife and our 3 kids. I would have advised not putting such massive emphasis on salary. I remember when I was 23, I turned down my dream job because the salary was $3,000 lower than what I was making.
  • Lastly, friends are nice, but family is eternal.
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