Author: David Cummings

  • The Role of Timing in Recruiting Talent

    Last week, I was talking to an entrepreneur who excitedly shared about an amazing new hire on his team. After discussing new hire for a bit, I asked what led to being able to recruit this new person. He said that he had been building a relationship with him for three years.  When his previous…

  • Investor Reserves Didn’t Go to the Expected Companies

    One of the most common adages in the venture and growth equity world is that you should reserve a meaningful percentage of the fund to participate in follow-on rounds. This usually translates to reserving between a quarter and half of the fund to double down on companies that are winning and performing the best, as…

  • I Have All the Problems I Want to Have

    I remember meeting an entrepreneur 15 years ago, having the opportunity to ask questions, and learning about his life. He had sold his business the prior year and was working on his next thing. As the conversation progressed, he made a statement that I’ll never forget: “I have all the problems I want to have.”…

  • Unrealistic Goals Can Hurt Startup Morale

    In my early years of entrepreneurship, I was intensely focused on setting big, hairy, audacious goals and shooting for the moon. My approach involved dreaming big, working hard, and rallying the team around the exciting opportunities ahead. Over time, I’ve become more tempered, setting a big vision but adopting a more measured approach to the…

  • Simple Financial Distillation as a Mental Model

    Yesterday, I met with an entrepreneur, and we discussed a variety of ideas related to building community. Late in the conversation, he shared one of his favorite mental models and asked for one I liked. After thinking for a second, I knew my go-to: simply distilling the financial model or business down to its most…

  • In the Playbook of the Future Acquirer

    Last week, I caught up with an entrepreneur, discussing how things were going with his startup. We delved into the usual topics, sharing what we’ve learned over the years. A question arose: “What should you do to prepare for selling your business in the next couple of years?” After pondering, I shared a pivotal course…

  • Question the Repeated Advice from Experts

    Last week, I was catching up with an entrepreneur, and he shared with me that he kept receiving the same advice over and over again. However, after digging deeper and analyzing it from a first-principles perspective, it just didn’t make sense. We talked more and tried to delve deeper into it, and it became clear…

  • The First Serious Acquisition Conversation

    Late in 2012, we sold Pardot to ExactTarget and it was subsequently acquired by Salesforce.com. Only in January, the year before, we were actually in discussions to sell the business to HubSpot. At the time, HubSpot was focused on content marketing, search engine optimization, blogging, and analytics. They realized that marketing automation and using the…

  • Pleased but not Satisfied

    Last month, I was talking to the leader of a well-known organization about his approach to achieving excellence. We shared some of our own personal best practices and learnings over the years. He shared one that really resonated with me: the idea is to be pleased but not satisfied. This involves pushing the team hard…

  • Relief Valve During Stressful Periods

    Last week, I was talking to an entrepreneur, and we got to the topic of ways to relieve stress during especially difficult periods. He shared some of his past experiences, and I shared one of mine that I remember vividly.  Back in mid 2012, we were going through the process of selling our company. As…