David Cummings on Startups

Tag: Entrepreneurship

  • When It’s Time to Move on From a Successful Startup

    One of the harder conversations I have on an infrequent but recurring basis is meeting with entrepreneurs who are gung-ho, motivated, and excited about their stalled startup. Of course, they don’t want it to be a stalled startup. They want to keep growing and expanding, but for whatever reason, it’s not in the cards.

    Last month, I had one such conversation with an entrepreneur who had built a small business with many customers. Yet, no matter what he tried, the growth wasn’t there. Over the course of many years, he had willed the business to a sustainable size with a dozen employees, but the ceiling had been reached. Unfortunately for entrepreneurs, this is one of the most challenging situations. After years of blood, sweat, and tears to build a business with paying customers who love the product, and a strong desire to grow, it becomes clear that, at this moment in time, with this product and this team, further growth isn’t going to happen.

    For this particular entrepreneur, I asked a series of questions:

    • If you weren’t working on this business, what would you do?
    • If you stepped away from the company, what percentage of your growth plans for next year would be achieved?
    • If you found a buyer and sold the business, what would the acquirer do with it?
    • If you could wave a magic wand, what would you change about the business?

    Knowing I will never know as much about the startup as the entrepreneur does, my goal is to get them thinking from a first-principles perspective about where the company is headed, what’s best for the business, and what’s best for them at this stage of the journey.

    As expected, this is often a difficult and awkward conversation for the entrepreneur. Everyone—rightfully so—tries to be supportive, encouraging, and focused on helping them continue to grow the business. However, sometimes the entrepreneur has done everything in their power, and it no longer makes sense to continue down the same path.

    As an entrepreneur, operating in these gray areas, where there’s no perfect information and judgment calls must be made, is part of the journey. Sometimes, the call that needs to be made is to move on and find a home for the startup so the entrepreneur can make things right by the employees, partners, and investors. Then, the entrepreneur can start their next journey.

    When further growth and new milestones are no longer achievable, it may be time to evaluate all opportunities and consider whether it’s time to move on from a successful startup. 

  • 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.

  • The Unknown Entrepreneur Arc

    Last week, I met an entrepreneur for the first time and asked one of my favorite questions: why did you start your company? He shared his journey, which began with participating in a college engineering organization that exposed him to an industry. From there, he became heavily involved and achieved some success among the school competitions. This led to job in the field, which quickly revealed an emerging gap in the market. Recognizing this, he decided to start a business to solve the problem. Now, he has millions of dollars in revenue and a tremendous market opportunity ahead of him.

    Hearing his story reminded me of my own journey. I started by building small PC apps followed by websites. Over time, I identified an opportunity for a new class of software that made it easier to update and manage websites. This led to the idea of creating software to make B2B marketing more productive, which eventually inspired a whole host of other ideas.

    Reflecting on both his journey and my own, my biggest takeaway—beyond the clear influence of luck and timing—is that the best thing a potential entrepreneur can do is to put themselves out there. Observe trends, find ways to get involved, and do interesting work. You never know where it might lead.

    Potential entrepreneurs would benefit from studying the stories of others. It quickly becomes clear that much of entrepreneurship involves trying new things, experimenting, failing, and maintaining a mindset that opportunities are abundant. The world is always changing, with new trends and tailwinds constantly emerging.

    While it’s popular to say, “Follow your passion,” it’s better for potential entrepreneurs to develop an eye for how the world is evolving. Becoming a student of what’s changing and why will lead to opportunities.

  • The Quality of Entrepreneur Interactions

    Last week, I was talking to an investor about an entrepreneur he really enjoyed working with. Hearing the joy in his voice, I inquired about what made the experience so delightful. He said it was the quality of the entrepreneur’s interactions.

    This idea has been on my mind ever since: the quality of interactions. After asking more questions and exploring the idea myself, here are a few examples of quality interactions between an entrepreneur and an investor:

    1. Timeliness of Response

    Whether it’s a phone call, email, or text, responsiveness matters. Of course, there’s always a lot going on, but some people manage their responsiveness better. Even if they don’t have time for a full conversation, a quick message like, “I’m tied up for the next few hours (or the day), but here are some good times to catch up,” or “I’ll get back to you by [specific time],” goes a long way. Quick, clear communication builds trust.

    2. Thoughtfulness on Unknown Questions

    Investors frequently ask entrepreneurs questions they might not immediately know the answers to:

    • What does this customer cohort look like?
    • How has this spend changed over time?
    • Where is the market headed in this sub-segment?

    It’s normal not to have all the answers. However, some entrepreneurs try to answer everything, even when it’s clear they don’t know. It’s much better and more thoughtful to respond with something like, “Great question. I don’t know the answer to that, but I’ll research it and get back to you.” Acknowledging what you don’t know and committing to follow up shows maturity and professionalism.

    3. Enthusiasm and Passion

    While entrepreneurs are generally optimistic—sometimes to a fault—those who demonstrate genuine passion and excitement are more enjoyable to interact with. That said, entrepreneurs shouldn’t fake enthusiasm, but ramping up energy and excitement within a natural spectrum of authenticity can make a big difference.

    4. Effort in Materials

    Investors often request board decks, data room access, financial models, etc. Everything an entrepreneur sends to an investor reflects their leadership, even if they didn’t create the document themselves. Typos, grammar mistakes, or low-quality work can reflect poorly on the business. With today’s AI tools, it’s easier than ever to ensure high-quality output. Taking the time to deliver polished, accurate materials builds credibility.

    5. Rhythm of Communication

    Investors value reliability and consistency in communication. Regular updates, such as a weekly email or monthly snapshot, can keep investors informed and confident in the business’s progress. Unfortunately, most entrepreneurs don’t take this proactive approach, leaving investors to request updates. Entrepreneurs who develop a consistent communication rhythm—showing transparency and reliability—provide peace of mind and demonstrate that these habits will continue as the business grows.

    People like to work with others who are thoughtful, conscientious, and care about the quality of interactions. This dynamic is especially important in relationships between entrepreneurs and investors, which often span many years or even decades.

    Recognizing the importance of timeliness, thoughtfulness, enthusiasm, effort, and consistent communication can significantly strengthen these relationships. Entrepreneurs would do well to evaluate their current level of interaction and look for opportunities to enhance or improve it.

  • Thiel’s Seven Questions Every Business Must Answer

    I always enjoy when entrepreneurs share their favorite books. Personally, I gravitate toward entrepreneur biographies, books about startup ideas, and general human interest. When Peter Thiel’s book Zero to One came out 10 years ago, I devoured it and recommended it to all my friends. Since then, I hadn’t re-read it, as I believed it was better to focus on books I hadn’t read before. However, I’m changing that approach and starting to revisit books I haven’t read in many years.

    Among the lists of popular startup books I regularly see, Zero to One is consistently included, so I decided to give it another read. It’s incredible and remains highly recommended. For all entrepreneurs, the section on the seven questions every business must answer is invaluable (pg 153):

    1. The Engineering Question
      Can you create breakthrough technology instead of incremental improvements?
    2. The Timing Question
      Is now the right time to start your particular business?
    3. The Monopoly Question
      Are you starting with a big share of a small market?
    4. The People Question
      Do you have the right team?
    5. The Distribution Question
      Do you have a way to not just create but deliver your product?
    6. The Durability Question
      Will your market position be defensible 10 and 20 years in the future?
    7. The Secret Question
      Have you identified a unique opportunity that others don’t see?

    Entrepreneurs would do well to answer these questions not only before starting a business but to revisit them on a regular basis in the context of their current direction and initiatives. Products and business models are dynamic, just like most things, and it’s easy to get in a rut without zooming out and asking the big questions consistently. Every business must answer these seven questions both for today and tomorrow.

  • Event Attendance Yields and Quality Product Feedback

    Last week, I spoke with an entrepreneur who volunteers for a local tech nonprofit, helping with event planning and securing speakers. We discussed events in general and shared best practices we’ve learned over the years. He pointed out something I’ve also observed: events that require payment, even a nominal fee like $10, tend to have a significantly different attendance yield compared to free events.

    In some cases, an organization includes events as part of its annual dues, but many groups choose to charge for events individually. What I’ve noticed on the attendance side is that when you charge for an event, the attendance rate (the percentage of people who actually show up) is often over 90%. In contrast, for free events—especially larger ones or those without a special draw—the attendance rate is typically around 60%. So, while people sign up for events in both cases, charging even a small fee increases the commitment and effort to attend.

    In this unscientific example, the attendance yield for paid events is roughly 50% higher than for free ones. How does this relate to startups? In the startup world, entrepreneurs are eager to get new products into the hands of potential customers. The most common approach is to give products away for free in the early stages to encourage usage and gather feedback. While this might work for a small subset of premium products, in most cases, entrepreneurs are better off charging something, even if it’s less than the eventual market price.

    By charging for the product, the bar for customer commitment is raised. When customers pay, they are more likely to use the product, and the quality and quantity of feedback improve significantly. The relationship becomes a true vendor/customer. 

    Entrepreneurs should consider the example of event attendance yields when comparing free versus paid events. Paid events, as expected, have a higher yield, which implies a greater level of commitment—even if the amount paid is minimal. Similarly, when entrepreneurs charge for a product, the customer’s seriousness is much greater, resulting in higher-quality feedback. Feedback is the lifeblood of products, and the most valuable feedback comes from customers who are invested, even if minimally.

  • 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.

  • Think RAGS for Startup Team Members

    10+ years ago I read Joel Spolsky’s seminal blog post The Guerrilla Guide to Interviewing. His theories on what to look for when hiring developers have been imprinted on my mind ever since: hire people who are smart and get things done. This applies to all hiring for all startup team members, not just developers, but misses two important ingredients — attitude and grit.

    Attitude permeates everything about a person. At Pardot, our values were positive, self-starting, and supportive. Each one of these values were embodied in the type of attitude we looked for in every person on our team. Of course, while values and attitude are different, attitude as a way to capture the desired personality traits works well.

    Continuing with attitude, the other missing characteristic that smart and gets things done doesn’t account for is grit. Grit is the idea of resilience and not giving up in the face of adversity. Angela Duckworth popularized it as passionate persistence, which captures it well. Startups are inherently challenging, so while this might be less important in a company not focused on high growth, in the startup world grit is invaluable.

    Combining these all together produces the RAGS acronym:

    • Results – Gets things done and continually makes progress
    • Attitude – Personality traits and view of the world that aligns with the core values
    • Grit – Passionate persistence, especially in challenging situations
    • Smarts – Ability to synthesize information and make quality decisions

    Defining results, attitude, grit, and smarts is up to each entrepreneur and their view of the world. Overall, the big idea is that this needs to be done intentionally, not haphazardly, and everyone must be held to the RAGS standards defined by the leaders.

  • SaaS/Web is Ideal for ADHD Entrepreneurs

    A common trait you’ll find among entrepreneurs is that they have tons of ideas and routinely can be described as ADHD. Due to this phenomenon, SaaS products, and the web in general, make for an ideal medium as it affords an elegant manner with which to constantly tinker. In many cases, you can have an idea, see it live in production, and get customer feedback in a matter of days or weeks (with strong automated testing, of course!). What other types of products allow you to do that? Physical goods? No. Services? Rarely.

    Constant iteration and innovation really is adrenaline for enterpreneurs. It doesn’t get much better than SaaS/Web for products.

  • Debt is Your Friend

    This one is for entrepreneurs and not consumers: debt is your friend. Too often, first time entrepreneurs think the first step to starting a business is raising money from other people or venture capitalists. My recommendation is to get the business off the ground doing whatever it takes — including using your credit cards. I used credit cards for my business eight years ago and even played the game of applying for new cards that had no interest for the first X months and transferring balances between cards in an effort to minimize the interest rate. Having tens of thousands of dollars of credit card debt, like I had, isn’t for the faint of heart, and is not recommended for most people, but it is often times the only way to get access to money.

    As for banks, the truth is that most entrepreneurs will never get a loan from a traditional bank unless you have collateral for 80% of the value (e.g. stocks, bonds, real estate, accounts receivables, etc). People think banks are in the market of loaning money but they are really in the market of buying physical goods on your behalf and letting you pay them back for it. They aren’t there to fund your dreams that involve intangible assets.

    My advice is to seriously consider debt whenever possible.