Growing and scaling a business is challenging at the best of times, but even more so in the current economic climate. To shed light on the strategies and mindset essential for success, we had the privilege of sitting down with entrepreneur extraordinaire David Siegel, to hear his advice for entrepreneurs.

Having held leadership roles in tech businesses since the late 90’s, when he was Director at DoubleClick (acquired by Google), David is more recently known for his tenure as CEO of Investopedia and CEO of Meetup, the latter of which he sold in January. As if those accomplishments weren’t impressive enough, David is also author of Decide & Conquer and teaches entrepreneurship at Columbia University.

In this exclusive, high-energy interview, we delve into David’s insights and advice for fellow entrepreneurs striving for success.

Question: It’s fair to say you’re a serial entrepreneur, so what do you most enjoy about building and scaling businesses?

The idea of creating something from nothing is deeply meaningful because, frankly, I think we all aspire to make an impact on the world. If you’re one small cog in a giant company, it’s likely that the company would have been the same regardless of whether or not you were there. But when you’re part of a startup, and the startup is ultimately successful, you’re creating jobs, you’re creating culture and you’re creating products. You’re making a real difference, especially with a company like Meetup that changes people’s lives.  It gives you that sense of meaning that I think we all crave.

Question: Do you have any specific routines that you feel play an important role in your success?

I think we’re all servants to our habits, both good and bad, and have read a couple of books, The Power of Habits, and Atomic Habits, which look at how small changes to our habits can bring about significant transformations.

I am very habitual in terms of my day and what I do. I wake up at pretty much the same time every day, and it’s Groundhog Day. I drink a lot of water, have various supplements, eat a healthy breakfast and then most importantly, I exercise. I think exercise is one of the best investments – giving you energy throughout the day to do more, be more efficient and make more of an impact, not to mention helping you sleep well at night. So, for the last 20 plus years, I’ve exercised five days a week, almost religiously.

Some other habits I’ve formed are not bringing my phone into the bedroom, ever, because I think it’s important to have separation from work. At one point I was even able to leave my phone in the car when I came home, but that’s not really possible in a post-covid world. But I have lots of different personal and work habits if you are interested in something specific.

Question: Ok, so what are your habits for email management?

That’s an interesting one. I think one of the mistakes that people oftentimes make is reading emails, but then not doing anything with them. They leave them sitting in their Inbox which means they have to waste time going back and re-reading them. And then there becomes the compounding weight of having too many emails to respond to.

95% of the time when I read an email, I take some action. That action may be responding, it may be deleting the message, or forwarding it. But critically, I avoid having to look at the same thing multiple times. I try to take action extremely quickly and then move on to the next thing, even if that comes at the expense of good grammar, spelling, or flowing language. Occasionally, if there’s something important, I’ll flag it, which means I will follow up with it, but then I just look at my flagged messages.

Generally, I have a very clean inbox and try to have a zero-inbox approach. I would say that 98% of the time, by the time I go to bed, there are no emails in my Inbox.

Question: What do you feel is the hardest thing about being an entrepreneur?

For many people, the problem with entrepreneurship, and then leadership more broadly, is loneliness at the top. Entrepreneurs feel that no one can understand what they’re really going through. They can’t really talk to their leadership team about the challenges they’re facing as there’s a power dynamic that can disenable transparent conversations. They seek out things like YPO (Young Presidents’ Organization) or similar organizations that help CEOs connect with other leaders.

That’s a very common challenge, although honestly speaking, it’s not one of mine, as I’ve always had a very strong network of tech leaders and mentors that I keep in touch with and go to with any of my issues. I also don’t feel lonely as I share everything with my executive team. I don’t keep things to myself. If we’re looking to get acquired, I tell them. If we’re looking to acquire a company, I tell them. There’s almost nothing I won’t tell them. Or if I can’t tell the whole executive team, the CFO will know or the CTO – a small group within the executive team.

I think it’s important to share information and not just because it prevents that sense of loneliness at the top, but because I really believe in radical candor. Trust and transparency are some of Meetup’s core values that we instilled when we were starting out.

Question: What do you feel is the biggest challenge facing entrepreneurs in the current market?

Fundraising. It’s a different world to a few years ago, pre-COVID. And in the last two years it’s deteriorated even more. Previously, companies that were losing money were funded. Companies that were just an idea were funded. Now, not only do companies need to demonstrate a pathway to profit, some need to show that they’re already profitable. All except AI-based or cyber-security companies, which seem to have a magic wand making the rules around profit inapplicable – probably because of the potential upside.

But outside of those two areas, it’s really hard to fundraise at the moment. There are so many companies that have gone out of business that the expectations for profit, for product-market fit, and maturation of business are greater now than they were in the past.

Question: Do you have any specific advice for entrepreneurs embarking on a fundraising round?

Yes, I would say be really thoughtful about whether now is the right time to raise money. If you’re able to demonstrate greater momentum in 6-12 months, the market will be in a better position. The amount that you’ll have to give up for your company, and the valuation you’re going to get, will be less than you’re expecting in the current climate. If you’re able to build more runway, do it. If you’re able to decrease your cash burn, do it. Think really carefully about timing and enable yourself to have more of a runway than you may have needed in the past, so you can choose the right time for fundraising.

You also need to think about how you approach investors. I see a lot of ‘spray and pray’ philosophies, where startup founders are simply contacting every single VC or angel investor they know. I think it’s important to be thoughtful about the strategies that different funds have and to cater your message towards their specific strategy. If their fund strategy is to write lots of small checks for companies at certain stages, understand that. If it’s focused on specific sectors, understand that. The more you can understand, the more you can cater your pitch and the higher the likelihood of conversion and success.

Lastly, it’s key to mention that the time to start relationships with potential investors is not when you need the money. It’s when you don’t need the money. It’s never too early to start building those types of relationships. Really think through how you start building the relationships you’ll need later, so that they’ll already be established when you need them.

Question: What is the single-most important thing you feel you’ve learnt about running a business, that you wouldn’t learn in business school?

I think the answer for me is that EQ, emotional intelligence, is more important than IQ. In business school, you learn analytical skills. I went to Wharton Business School. It has a highly analytically finance-driven, marketing-driven pedagogy. Soft skills were kind of laughed at. But when you get into the real world, one’s ability to influence, one’s ability to build relationships, one’s ability to communicate effectively, to read the room, to have empathy for others and to understand how to manage people are all much more important than just pure brain power.

Question: What do you look for in your team and what team culture do you feel is most conducive to success?

I try to build teams of people with complementary skillsets and build a culture of healthy tension. For example, I’m a very extroverted person. I’m very optimistic. I tend to focus on the big picture rather than getting into ‘the weeds’. That means I have to surround myself with people who are different to me – who are more introspective, more detailed, or more tech-oriented, as I’m more business-oriented.

And the ultimate executive team will have some tension – where people are willing to, respectfully, disagree. Because if there’s no tension, bad decisions will ultimately be made. You certainly want to avoid a situation in which the CEO dictates a strategy that everyone mindlessly follows. I don’t want to hire ‘yes people’ but those with the ability to constructively challenge a specific direction, and clearly articulate any potential shortcomings.

Finally, what is your current focus?

I sold Meetup a few months ago, after running the company for about five and a half years. It was a very bittersweet experience because Meetup is all about ending the loneliness epidemic, building friendships and connections between people – something that is so important in this world. So, I decided I wanted to focus on a new type of connection and relationship, specifically one where there’s a lot of pain and challenge, which is in the Middle East, or more specifically Israel.

I organized a group of about 120 tech leaders over two different missions to spend time with venture capitalists and startup founders in Israel. People (including Qodeo’s CEO, Simon Glass) came from the US, the UK and other countries to share a very deeply meaningful and impactful experience called the Israel Tech Mission.

We’re now turning that into a nonprofit organization, hiring an executive director and looking to connect the Israeli tech ecosystem with the global tech ecosystem in ways that are more important today than they’ve ever been. 26% of Israel’s economy is dependent on tech, which is higher than any other country in the world, and supporting the Israeli economy, indirectly supports their political and social systems. There is no organization that brings the largest and most important tech businesses and investors to Israel. We are going to be that organization, and it’s incredibly exciting to me.

A huge thank you to David Siegel for sharing his invaluable experiences with our readership. For more tips for entrepreneurs, check out the first in our series of articles debunking fundraising myths, where we explore whether the most prestigious investors are the best fit for your business.