David Cummings on Startups

Tag: entrepreneur

  • Investor Responsiveness as #1 Value

    Last month, I was talking to an entrepreneur about his experience with a variety of investors over multiple rounds of funding. Toward the end of the conversation, I asked which investor provided the most value and why. Without missing a beat, he said one of the investors stood out, and that the main driver of value was simply responsiveness. Anytime the entrepreneur had a question, the investor would respond immediately with an email or a phone call, regardless of the time of day or day of the week.

    At first, when an investor gets involved, there’s a period of time where the entrepreneur and investor feel out the relationship. What’s appropriate? What’s a good cadence for checking in? What areas does the investor like to work on or help with? And so on. From an investor’s perspective, they might invest in a couple of startups per year, up to dozens depending on their style. Whereas an entrepreneur might have a handful of serious investors and several casual investors on their cap table. The ratios of relationships are nowhere near the same.

    As an entrepreneur goes through an issue, or opportunity for the first time, having an investor who has been there before in a similar situation can be invaluable. Only, the investor has to want to share and spend time with the entrepreneur for it to be mutually beneficial.

    Thinking about this entrepreneur’s comment—that his most valuable investor was the one who was most responsive—makes sense. The entrepreneur is in the trenches, working hard to make progress, and having an on-demand sounding board with experience and knowledge is invaluable.

    My recommendation for entrepreneurs when talking to potential investors is to ask how they like to work with the entrepreneurs they invest in. Entrepreneurs would do well to have a go-to person they look forward to talking with, who has relevant experience and, crucially, is super responsive.

  • Market A or B for a Startup

    Last week, I spoke with an entrepreneur who shared his elevator pitch. I then asked a few questions and learned more about his business. He mentioned that they have two early adopter customers: one in Industry A with a unique use case, and another in Industry B with a completely different use case. He then asked which market I thought he should focus on. After posing more questions about the product being a must-have versus it being a nice-to-have, and trying to understand the mission-critical nature of the application, it became clear that there wasn’t enough information available yet. I explained that I couldn’t provide any recommendations on which direction to pursue. Instead, I suggested that he either sign more customers and evaluate which use cases are most valuable or spend time with the existing two customers, diving so deeply that he could make a gut decision about which market is better for his business overall.

    In this example, my recommendation is to acquire at least 10 unaffiliated customers to create a broader sample set. This would allow him to learn how, why, where, and when they use the product. From there, the best direction forward would likely become obvious. Back in our time at Pardot, we debated this for years. We initially targeted very small businesses, then small businesses, followed by small-to-medium-sized businesses, and ultimately settled on medium-sized businesses, as well as emerging-growth small businesses. Over time, we honed in on three characteristics that our most successful customers shared.

    First, they had an email newsletter sign-up box on their website. This indicated that they used email marketing in their business and likely engaged in regular communication, such as a monthly newsletter. Second, they ran Google Ads for their product. When we searched the company name or product name and found Google Ads, it showed us that they were investing in lead generation, implying a certain level of marketing presence. Third, we would search the company name on LinkedIn to see if they had any sales reps listed as employees. If they did, it suggested they had a consultative sales process, making a B2B marketing automation platform like ours a worthwhile investment.

    Naturally, we wrote some code to automate the process of finding companies that met these three criteria and used that as our prospecting mechanism for cold outbound to companies that fit our profile. While this example focuses more on identifying common criteria for an ideal customer rather than choosing a specific market, it’s instructive. The ideal customer might not be tied to a particular market or vertical. In our case at Pardot, it was a very horizontal product, and these three criteria were strong indicators of whether a company would succeed with it.

    My recommendation for entrepreneurs is to sign at least 10—if not more—unaffiliated customers and spend a tremendous amount of time with them, either in person or over a Zoom call. Talk to the customers and learn every minute detail possible about why they bought the product, how they use it, and what value they derive from it. Choosing a market, a vertical, or even criteria for the ideal customer is a critical step in an entrepreneur’s journey and should not be taken lightly.

  • Entrepreneur Updates as Leading Indicator of Success

    Last week, a fellow entrepreneur said something to me that really stuck in my mind: “I knew he’d be successful based on his updates.” In this case, we’re both angel investors in another entrepreneur’s venture, and we were talking about all the great progress this company is making. The comment about the updates got me thinking and reminded me of another entrepreneur’s regular updates that I receive, which are unbelievably good. Now, when describing the updates as “good,” it isn’t that the business is doing well—although in both cases here, they are—rather, it’s the style, tone, thoughtfulness, quality, and creativeness of the update. It’s about connecting the reader with anecdotes, stories, and emotion, and providing metrics and data in a way that’s easily consumable and approachable. Yes, there are a number of monthly update templates online, and entrepreneurs should default to those if they don’t have their own.

    Regular updates, as well as past board decks and strategy documents, are some of the most informative resources when doing due diligence on a startup, whether you’re a potential investor or a potential mentor. One of my favorite pieces of advice is to ask for these historical documents and use them to look for trends, thoughtfulness, and how an entrepreneur thinks. The goal isn’t to find perfect updates from the last three years; rather, it’s to look for evolution and maturation of thought. It’s to see if the entrepreneur articulates both what has gone well and what hasn’t. Too often, entrepreneurs gloss over the hard times when communicating, but those who do address them often show a greater level of experience and understand that by sharing the challenges, they also share the opportunity for others to help. Past updates and other regular corporate communications are the first place I like to start when understanding an entrepreneur and a startup.

    Entrepreneurs should always provide regular updates. The alternative—not doing any updates—is strongly discouraged. Rather, the big idea is that updates are one of the best ways to connect with all constituents, from employees to partners to mentors to investors. For some entrepreneurs, this can be a calling card that helps differentiate them from others in the market.

  • Double Revenue With No Additional Employees

    For the first 10+ years of my entrepreneurial journey, I was too focused on the number of employees as a key measure of success. When meeting other entrepreneurs, one of the first questions I asked to gauge the size and scale of their business was, So, how many employees do you have now? While that question is still relevant today, it is much less so than in the past.

    Productivity per employee has increased tremendously. The ability to leverage software and other systems for scaling has improved dramatically. The nature of work has also evolved, with more remote and hybrid work arrangements and a greater reliance on contractors and freelancers. My previous belief that W-2 employees were a key proxy for success no longer holds. In fact, many predict that we will see more billion-dollar companies in the future with only a small handful of employees.

    Last week, I heard an entrepreneur say he wants to double the size of his business without increasing headcount. This doesn’t mean keeping the exact same team but rather using AI to boost productivity, outsourcing more functions, and recruiting higher-skilled employees when attrition occurs. The key idea is that as teams grow, management and leadership demands increase, and the organization tends to move more slowly. In this case, the entrepreneur operates at considerable scale, and there is also a focus on increasing annual recurring revenue per employee as a key metric for business health. The goal isn’t to build the largest team possible—it’s to build the most efficient and successful one.

    Entrepreneurs in the growth stage would benefit from considering how they could double their revenue without adding new headcount. What positions would remain? Which ones would be outsourced? Which roles would need to be filled by more experienced hires? What would be the advantages and drawbacks? Entrepreneurs should evaluate the relationship between in-house employees and scale earlier than they might have in the past.

  • 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.

  • Incredibly Narrow to Start

    Last week, I was catching up with some entrepreneurs who are off to a fast start. They’ve cobbled together a solution using a mix of off-the-shelf technology, proprietary technology, and human-in-the-loop services. However, the leads coming in have been for a variety of different use cases and ideas.

    It’s a high-class problem to have—clearly, the market wants what they’re offering. But as entrepreneurs with limited resources, it’s critical to focus on the most acute pain in the market. There’s an old adage in startup land: more startups die from indigestion than starvation. This means that startups often fail not from a lack of opportunity but from trying to do too many different things for too many different customers, ultimately taking on more than they can handle.

    So, how do you figure out where to focus when you’ve found an unmet need in the market? Here are a few ideas:

    • Quantify the value. How much are prospects willing to pay? Which ones have the most urgent need?
    • Timeline. Who can roll out the technology the fastest? This can also serve as a proxy for urgency and value.
    • Size of market segment. Looking beyond these initial leads, which market opportunity has the most long-term potential? Getting a wedge into a small but fast-growing market that will eventually be large is one of the best ways to build a business.
    • Customer-funded development. Is a potential customer willing to fund new features and solutions to address their needs? In an ideal scenario, customer pain aligns with the entrepreneur’s vision, and development is funded by the customer.
    • Willingness to partner. Is the prospect interested in joining a customer advisory board and influencing future development? Some people enjoy being influencers, even for B2B products. These individuals are incredibly valuable to startups as they provide testimonials and answer reference calls—don’t underestimate the importance of having a customer who cares.

    Ultimately, it benefits the entrepreneur to zoom in and focus on the use case that both fits their vision and has the potential to build the foundation of a business that matches their ambition. Entrepreneurs would do well to start unbelievably narrow, nail it, and then expand. Starting small is the way to go big.

  • 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.