David Cummings on Startups

Tag: success

  • The Entrepreneur’s Passion

    Last week, I was talking to an entrepreneur, and one of the things that stood out was the passion in his voice. You could tell he was fired up and committed to building a business with a strong sense of customer empathy.

    When talking to entrepreneurs, I always enjoy asking questions like: Why did you start this business? Why is now the right time to create this company? What makes you uniquely suited to succeed? While these are important questions, a key nuance is the passion exuded by the entrepreneur. Does he really care? Does he truly want to make this happen? What sacrifices is he willing to make?

    The challenge with discussing passion is that it can be subjective. Different personality styles express passion in different ways. Some people get excited, talking fast and with high energy. Others become serious, showing a deep conviction. While passion comes in different forms, it’s ultimately one of those things you recognize when you see it.

    One final note is about the intersection of entrepreneurs searching for a great idea versus being passionate about that idea. This can be a tough balance. Great ideas are hard to find, and while some entrepreneurs are passionate about anything and everything, others struggle to get excited even when they find a strong idea. For many, that lack of excitement is a dealbreaker.

    From my experience, most things that move society forward, help others, or solve meaningful problems provide a foundation for passion. Of course, it’s ideal to find a need in an area you’re already passionate about, but I wouldn’t limit the search for a great idea to things that are immediately exciting.

    The next time you talk to an entrepreneur, listen to his voice. Pay attention to the excitement around the idea. After the conversation, do a mental analysis of his level of passion. Some of the most successful entrepreneurs I know are also the most passionate about their mission.

  • Daily Check-in Amongst Entrepreneurs

    Back in 2011 and 2012, Pardot was experiencing rapid growth, generating millions of dollars in recurring revenue. As an entrepreneur who enjoyed starting new ventures and identifying potential business ideas, I regularly engaged with other aspiring entrepreneurs. By that point, I was collaborating with several excellent entrepreneurs, including Craig Hyde on Rigor, a web performance monitoring platform, and Kyle Porter on Salesloft, a sales engagement software platform.

    One of our early initiatives was a daily check-in among all of us. This simple yet effective practice involved gathering for 10 minutes each morning to answer three straightforward questions: What did you accomplish yesterday? What are you going to do today? Are there any roadblocks?

    This approach resonated with us as it should for any team or business stage. However, it was particularly valuable to our group of entrepreneurs working on their own ventures. Entrepreneurship is a rollercoaster of ups and downs, with highs and lows that are best shared with people we trust. But by having a small group of like-minded individuals check in with each other daily, we created an accountability network.

    We shared ideas faster, identifying what was working and what wasn’t. We calibrated the different components of our businesses, exploring how they could complement each other. There’s a lot of talk about remote and hybrid work when the goal is to grow as quickly as possible, both for the business and for the individual. While navigating the challenges of starting from scratch, entrepreneurs would benefit from finding a cohort of other entrepreneurs, preferably a small group of those who genuinely enjoy helping each other.

    At that stage of our careers and entrepreneurial journeys, maintaining a standing daily check-in proved invaluable. It allowed us to meet, share our experiences, and grow together as a group. Entrepreneurs should find a peer group and look for ways to grow faster with activities like a daily check-in.

  • Highlight an Employee Failure at the Town Hall

    Last week, I attended an entrepreneur event where the speaker shared some of his best practices for growing a successful startup. One thing he said really stuck with me: if you want to promote a culture where failure is accepted and independent thinking is encouraged, you must work to share stories internally in a public context that reinforce this message. 

    In this context, it’s not failure for the sake of failure, but failure in the pursuit of thoughtful risk-taking. At this particular startup, during their regular all-hands town halls, they would feature a team member as one of the speakers. That team member would be interviewed about a specific failure. The conversation would cover what the goals were, what the expectations were, why the initiative was pursued, why it didn’t work, and most importantly, what was learned from the experience.

    At the end of the conversation, they would emphasize that this type of scenario—failure through thoughtful risk-taking—is encouraged at the company. The message was clear: failure for the sake of failure is not good, but failure in the context of thoughtful risk-taking is valuable. 

    Most companies and most people, by default, avoid admitting failure. As entrepreneurs and leaders, it’s important to acknowledge when things don’t work out and to set a standard that encourages thoughtful risk-taking, rather than discouraging it, as is common in many businesses.

    For entrepreneurs, I recommend incorporating a failure segment into your regular all-hands meetings. This way, employees consistently hear the message that thoughtful risk-taking is encouraged. Celebrate the fact that the more you experiment and learn, the faster you grow, both as an individual and as a business.