David Cummings on Startups

Tag: technology

  • Use Advanced Prompts for More AI Value

    Last week I was at dinner with a group of executives, and of course, the topic of ChatGPT and AI came up. We went around and shared some of our favorite use cases for the technology, as well as ways we are experimenting with AI in our respective companies. Then I asked if anyone used existing prompts or more advanced context engineering. Not a single person did.

    On the one hand, it is so powerful that you can ask questions, give it scenarios, upload documents, have it search the web, and with very little context, it quickly provides valuable answers and insights. So if you can do that with limited instructions, imagine what it can do with much longer, more detailed instructions.

    That’s where prompt engineering templates come in. These are simply text—nothing more, nothing less—but by using these more comprehensive directions, you can get even more value from the AI.

    Let’s look at a shared prompt example from Josh Kopelman for comparing board meeting decks. The prompt asks for two PDFs and does the following, with the output as a PDF document formatted and ready to go:

    1 Snag the Numbers

    Search every slide for hard metrics (ARR, revenue, burn, hires, NPS, runway, churn…).

    Always show Prev (Actual) ➜ Curr (Target) ➜ Curr (Actual) ➜ variance.

    2 What They Said vs. What They Did

    List each commitment from the earlier deck (note slide). Under each, add status & note from the later deck,

    3 Goal-Drift Radar

    Call out any KPI whose name, definition, or cadence changed. List metrics that existed in the earlier deck but vanished in the later one.

    4 Overall Verdict

    • One-liner verdict with a traffic-light word (RED / YELLOW / GREEN).

    • Follow with a breezy 4-to-6-bullet executive summary (≤ 150 words).

    5 Rays of Sunshine & Storm Clouds

    • Top 3 positives (good surprises, momentum).

    • Top 3 concerns (lags, risks).

    Cite slide numbers in parentheses.

    6 Eight Smart Questions for the Team

    Short, pointed follow-ups to close any info gaps.

    Here’s the shared prompt board deck comparison prompt with the text for ChatGPT.

    The overall idea is producing an experienced analyst report that might take a few hours and doing it nearly instantly with AI.

    For entrepreneurs, the recommendation is to search for shared prompts online in the context of the work being done. If you’re analyzing term sheets, go online and find example prompts that do a much more detailed analysis than just a basic prompt. If you’re analyzing a partnership agreement, use the shared prompt that will give you more valuable insights. The AI results are great, and with a more advanced prompt, they’ll be even better.

  • Starting Over as an Entrepreneur

    Recently, I was asked what I would do if I could start over as an entrepreneur. This question prompted me to reflect on my journey, particularly the early years when I tried numerous ideas that didn’t succeed. Looking back to my earliest beginnings in the late 1990s, when the Internet was taking off, I started as a freelance web developer during high school and college, building websites for small businesses and nonprofits.

    After several years of freelancing, I listened to client feedback and requests, which led to my first real software product idea: a web content management system delivered as Software as a Service (SaaS). This concept didn’t exist at the time. The key lesson was that the Internet’s rapid growth created opportunities for businesses and organizations eager to establish an online presence but lacking the expertise or desire to do it themselves. They were happy to pay for someone to handle the work and act as their consultant.

    How does this tie back to the question of starting over as an entrepreneur today? The current excitement and energy around artificial intelligence (AI), which feels reminiscent of the Internet boom in the late 1990s. The enthusiasm for AI and its potential to transform the world mirrors that earlier era. Just as I helped companies navigate the shift to the Internet, I would now position myself as an AI consultant. I would cold-call and network with businesses and organizations to help them integrate AI tools and consult on optimizing their processes with AI.

    However, the ultimate goal isn’t to remain an AI consultant. Instead, it’s to build relationships with a variety of businesses to identify unmet market needs. From there, I would develop AI-powered business software to help companies operate more efficiently and build a startup around that idea. Rather than searching for a software idea directly from the market, I propose an intermediate step: becoming a general AI problem-solver for companies. This involves doing real work, adding tangible value, and listening to authentic feedback for as long as it takes to discover a compelling AI-related software idea.

    My recommendation to aspiring entrepreneurs interested in B2B software is to work with various companies, assisting them with AI-related change management. This approach mirrors my efforts decades ago, helping organizations derive value from the Internet. While the future is uncertain, I firmly believe AI is the next major technological wave. A tremendous amount of technology implementation and change management will be required, particularly in helping businesses unlock AI’s potential. This work will uncover countless opportunities for new software products, paving the way for thousands of new startups.

  • From Speed Alone to Speed + Quality

    Most beginning entrepreneurs suffer from the same problem: chasing too many shiny objects. With a clean slate or in the early stages of a new venture, there’s no shortage of ideas to pursue. When a prospect asks for something, the response is often, “Let’s do it.” If a different prospect requests something completely unrelated, the answer is, “Sure, why not?” The goal is to build a business, so responding to customer requests seems logical, right? However, this approach quickly breaks down due to finite resources and limited time. I often say that more startups have died from indigestion rather than starvation.

    In the early days of Pardot, we were building what is now known as marketing automation software, but it didn’t have a term back then. At one point, we called it lead generation software, then lead management software, and eventually, the term that stuck was marketing automation. The fact that we called it lead management software was indicative of what we started doing at the beginning. However, I made the rookie mistake of trying to do too much too fast. While we needed to offer forms, lead routing, lead scoring, and basically an intake system for leads generated on the website that could then be connected to a CRM, we kept building and building. We wanted to have the most feature-rich system, but we lost sight of maintaining a level of quality control at the same time. Being small and nimble, we had to move fast and build out our system, but the lack of quality was driven home one day when I came into the office and customers started reporting that they were seeing leads in their system that they didn’t generate themselves. That’s right; we were cross-contaminating data. Leads generated from one customer were being put into other customers’ systems. Uh-oh, we had moved fast and broken things. It’s one thing to have little bugs that affect the user experience or annoy a customer for a bit; it’s an entirely different thing to corrupt one customer’s data with another’s.

    After quite a bit of work, we had cleaned up the data and addressed the issues in the system. Thankfully, we had learned our lesson: speed creates an early advantage, but speed plus quality is the sustainable advantage.

    Entrepreneurs should use speed to their advantage and iterate as quickly as possible for the customer. Yet, within this context, it’s critical to maintain a strong opinion of where the market is headed and regularly say no to requests that are outside of the vision. Over time, pure speed gets replaced with speed and quality. Pay attention to the signs and be ready to add more efforts around quality as the customer count grows.