Introducing the Executive Insights Series

Entrepreneurs are trend setters, risk takers and those with enough conviction to pursue a new solution to a tireless problem.

They come from all corners of the world, and we are fortunate to work with dozens of the most exciting entrepreneurs across the most disruptive in technology. In an effort to share best practices, lessons learned, trials and tribulations and stories about the entrepreneurial journey, we are launching the Executive Insights Series. Here, we'll feature insights and stories from CEOs, founders and executives to help other entrepreneurs learn from first-hand experience about sales, marketing, culture, hiring, acquisitions, fundraising and much more.

Revisit this blog post to find new articles from leaders across our global portfolio.

5 Tips on When, Why and How Much to Raise

Ryan Holmes, CEO, Hootsuite

With capital comes responsibility. The startup graveyard, in fact, is littered with promising companies that came undone after getting too much money too fast. My own company has grown from 7 to 700 employees in about six years and learned some important lessons on funding along the way. Each startup’s circumstances are different, of course, but I think these ideas on when, why and how much to raise may be worth bearing in mind.

What the CEO of a $1B+ Company Learned From His Biggest Mistake

Ryan Smith, CEO, Qualtrics

If you’re not making mistakes, it means you’re not trying hard enough. At Qualtrics, I make sure all of our employees know it’s acceptable (and encouraged) to make mistakes. This is hard because being wrong sucks. But making mistakes means that you’re being creative, pushing the limits, and experimenting with new processes. The key is to learn from our mistakes — and learn fast.

Creating Culture: An Imperfect Recipe

Andy Dunn, CEO, Bonobos

I – like most entrepreneurs – was not handed a recipe for a great and lasting culture when I co-founded Bonobos. However, I have been lucky to piece together the wisdom of many who have come before me. So, I came up with my own framework by distilling personal cultural successes and failures while building Bonobos into the brand it is today. Let's dive in.

Re-Aggregating the Web

John Milinovich, CEO, URX

The key ingredient is to implement deep links across any and all platforms that make sense for your company. Fortunately, the methodology for each is similar and the benefits of discovery via Google search or social sharing is to great to pass up. The reality is that a unified standard is unlikely to appear anytime soon, so it’s most important to pick at least one so partners can link directly into your app.

HotelTonight's CEO on How to Avoid Defensiveness When Getting Feedback

Sam Shank, CEO, HotelTonight

Successful companies communicate and collaborate consistently, and honestly. With rapidly-growing companies, this can be a challenge. Hear how HotelTonight improved communication and fostered a spirit of collaboration and openness by investing in leadership and feedback coaching.