Blog

  • Foosball and the Startup Journey

    As we’re dreaming up amenities and experiences for entrepreneurs in South Downtown Atlanta, I’m reminded of the early years, when things were much more challenging and lean.

    When I first moved to Atlanta in 2002, our big customer at the time, Noble Investment Group, was kind enough to provide office space for us in a couple of empty rooms at the end of the hall on the 14th floor of a beautiful skyscraper. As part of the arrangement, we were able to use their kitchen with foosball table. Now, while the foosball table might seem like an overdone perk for a cool office vibe, we wore that table out and played for hours and hours.

    After a little over a year working out of their office and sharing space, we needed to get our own office and went through the typical startup process at the time: looking at subleases, because facilities like the Atlanta Tech Village and co-working spaces didn’t exist. We found a great little sublease at 550 Pharr Rd. that was furnished and ready for occupancy. Only it was missing one critical element: the foosball table.

    We had just spent our last dime getting things situated, and I really wanted that foosball table. So I did something that I wouldn’t recommend: I went over to Dick’s Sporting Goods, and at the time, they had an offer where if you signed up for a Dick’s Sporting Goods–branded credit card, you would get $50 off any purchase. So I signed up for a new credit card and got $50 off the brand-new $200 foosball table. Again, not recommended, as it’s a slippery slope to sign up for lots of credit cards and go down that rabbit hole. But while the business was growing nicely, the hard truth is that the faster you grow, often the more cash you need—and we didn’t have enough cash.

    After hand-assembling that new foosball table in the sublease, the amount of foosball we played relative to the previous office went down dramatically. It wasn’t the foosball’s fault; the culture evolved, the team changed, and we spent more time doing things like going out to lunch every day as our new activity.

    Now, anytime I see a foosball table, I think of those early years and of signing up for a credit card just to save 50 bucks. I’m grateful for those memories and for being able to reflect on how the priorities, resources, and journey have evolved.

    For entrepreneurs in the hurricane of building their businesses, remember that this is one moment in time, and that as you keep pushing forward, it too will evolve and hopefully improve. What might be a fun team activity around a foosball table might not be the same vibe the following year. But holding onto those memories—even if there’s a little financial hiccup, like signing up for a credit card to try to keep the foosball vibe alive—makes it that much sweeter. Enjoy the journey today, right now.

  • KPI Definitions in Board Decks

    A question I get from entrepreneurs from time to time is to look at past board decks from other startups. Board decks are a normal part of venture-backed startups and help align the executive team, the entrepreneur, and the investors on a quarterly basis.

    Now, decks don’t have a defined standard, so they are a little bit all over the place. But the best ones capture what’s going well, what’s not going well, the strategy, plans, and, of course, metrics.

    On the metrics front, one thing I’ve seen more frequently — but never saw over the first 10 or 15 years — is KPI definitions. Board decks include a variety of performance indicators and metrics, but just because it says “recurring revenue” or “gross renewal rate” doesn’t mean it’s measured the same way everyone else measures it.

    The trend now is to include KPI definitions at the end of the deck that outline each KPI, the unit of measurement, and how it’s calculated. Here’s a list of common board metrics:

    Corporate

    • ARR
    • Net new ACV
    • Net dollar retention
    • Gross dollar retention
    • Operating margin (Op margin)
    • Burn rate
    • Days to zero cash

    Marketing

    • Signups
    • Marketing qualified leads
    • Sales qualified leads

    Sales

    • Sales new ACV
    • Sales efficiency

    Customer Success

    • Managed portfolio efficiency
    • MP NDR (Net dollar retention)
    • MP GDR (Gross dollar retention)
    • CSM carry (ARR per CSM employee)

    Customer Support

    • Cost per case
    • Cost per MAU
    • Case close via automation
    • Support CSAT

    R&D

    • Plan / Do
    • Say / Do
    • Cycle times
    • Availability

    Finance

    • Expense actual to forecast
    • Days to close books
    • Net New ACV actual to forecast
    • Revenue actual to forecast

    People

    • Voluntary attrition 
    • New hire attrition
    • New hire starts
    • Exits

    Entrepreneurs would do well to include KPI definition slides at the end of their board decks to ensure that everyone is on the same page and the metrics are calculated in a way that is readily understood and, ideally, aligned with industry standards.

  • 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.

  • 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.

  • 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.

  • Ask for the Startup Office Tour

    Whenever I visit a founder at their office, I always ask for a tour. Naturally, the entrepreneur perks up, eager to show off their environment. So much time, energy, and thought go into building a cool, collaborative office that there’s a sense of pride and joy in sharing it with others. Beyond the basics—like how they organize the floor plan, conference rooms, breakout areas, and kitchens—I’m also on the lookout for ideas to bring back to our own office.

    For example, many years ago, I visited another startup’s office and noticed a giant TV mounted on the wall right by the front door. It displayed a scoreboard of their most important goals, color-coded red, yellow, green, and super green based on their progress. This was visible to everyone—employees and guests alike—making it clear where the company stood on its key metrics. Inspired, I immediately implemented this at our office, installing a massive TV in the lobby connected to a Mac Mini. It displayed a Google Sheet that automatically updated with red, yellow, green, and super green indicators based on our metrics.

    Today, depending on the startup, the office often serves as more of a way station, with employees splitting their time between a couple of days in the office and a couple of days working from home. While office usage has changed since pre-COVID, it still plays an important role for most companies. My recommendation for entrepreneurs is to always ask for a tour when visiting another entrepreneur’s office and to look for ideas they can adapt for their own environment. Constantly tinkering and improving across everything is one of the great joys of being a founder.

  • Three Quick Questions After Hearing a Founder’s Story

    Last week, I caught up with a very successful local entrepreneur. While I knew parts of his story, I hadn’t yet heard the origin of his idea. With enthusiasm, he shared the moment that sparked it all: a use case in the internet communications world that was becoming increasingly common but was incredibly cumbersome and tedious. That lightbulb moment led him to create a startup around a new human-centered process that eliminated friction and increased distribution, making the process super efficient.

    This story isn’t about the specifics of his idea but the value it delivered to customers. Too often, entrepreneurs chase shiny new technology or ideas that are only marginally better than existing alternatives. When hearing a new idea, consider these key questions:

    1. Is this solution ten times better than the alternative? Many new products offer only a 10% improvement, which the market often ignores. True success comes when a product addresses a real need and is exponentially better.
    2. Can this only be achieved with new technology? Too often, entrepreneurs build products whose output could still be produced manually or outsourced to a junior employee or AI. The best innovations are those that are impossible without specialized software, enabling what was previously unachievable.
    3. What are the growth prospects for this market? The most promising markets may be small today but are growing rapidly. Look five to seven years ahead and assess whether the market will become large and significant.

    I love hearing founders’ origin stories, and this one was exceptional. Entrepreneurs would benefit from reflecting on these three questions about product value, innovation, and market timing to guide their ventures toward success.

  • The Preemptive Funding Offer

    Last week, I caught up with an entrepreneur, and we discussed a preemptive funding offer. The startup is thriving, growing rapidly in a large market with limited competition. Currently, the entrepreneur doesn’t need to raise capital, especially as key business metrics continue to improve. As the company grows, potential investors frequently reach out to build relationships before funding becomes necessary. The entrepreneur has started taking these meetings to connect with the venture community. After a particularly promising meeting, one investor offered a substantial investment at a valuation significantly higher than the last round. So, what should the entrepreneur do?

    We weighed the pros and cons. On the pro side, accepting the offer provides time to assess the investor’s compatibility, ensuring the right chemistry and personality fit for a long-term partnership. The additional capital would support a more aggressive hiring plan, considering it takes three to six months to onboard and scale a team. This could accelerate growth and position the company for greater opportunities. Moreover, the extra funds could act as a financial cushion, offering flexibility to seize new opportunities without immediate spending pressure.

    On the con side, raising money now at a higher valuation, when it’s not needed, reduces optionality. It sets a higher exit bar, which could complicate a future sale. Additional capital also brings increased pressure to grow and expand, which can be beneficial but may sometimes hinder the business. Finally, if growth continues and funds aren’t immediately necessary, the entrepreneur could raise capital later at an even higher valuation, minimizing dilution.

    There’s no right or wrong answer—only an opportunity to reflect on priorities and goals. Entrepreneurs should build relationships with a select group of investors before their next funding round. Occasionally, these connections lead to preemptive offers, as in this case. When this happens, it’s an ideal time to evaluate the next round by listing the pros and cons of acting now versus sticking to the existing financing timeline.

  • Matching Funding with Entrepreneur Ambitions

    Last week, I caught up with an entrepreneur who shared an update on his company’s progress. The business has been growing steadily, boasting a critical mass of over 1,000 customers. Now, they’re contemplating their next round of financing. From a business perspective, the company checks many boxes that investors look for: high gross margin software, a solid growth rate that’s fast but not hyper-growth, and a large market with low single-digit overall growth.

    However, the challenge lies in potential scale. In its current form, the company is unlikely to grow large enough to become a standalone, publicly traded entity. To attract analyst coverage and interest from broader markets, a publicly traded company typically needs around $500 million in annual recurring revenue (ARR) and a growth rate exceeding 30%. For this business, that target feels unattainable under current circumstances.

    The startup has already raised some capital and has been relatively efficient, burning roughly $1 for every dollar of recurring revenue. Now, the entrepreneur faces a crossroads in the financing market. Growth equity investors might offer a modest valuation, aiming for a three- to fivefold return in three to five years. On the venture capital side, high-profile VCs seek moonshots with the potential for a hundredfold return—something this company doesn’t currently fit. Yet, the entrepreneur is highly ambitious and determined to build a large, standalone business.

    So, what’s the next step? Should he explore new product lines to transform the company into a multi-product business, despite its modest scale and limited resources? Or should he consider finding a home for the business now, allowing him to pursue his next idea in a year or two? This is a high-class problem, as the entrepreneur has already achieved a notable level of success but aspires to do more.

    My recommendation was to align the next round of funding with the business’s current potential and evaluate whether a smaller amount of capital could maintain optionality. Too often, entrepreneurs raise as much money as the market allows, which isn’t always best for the business. Here, raising capital requires careful consideration, especially since the entrepreneur aims to build a larger business than the current market supports. He’ll need to either expand the product line, adding complexity, or temper his ambitions and consider building another company in the future.

  • Find the Community Super Connector

    Last week, I attended a startup event and met with various entrepreneurs. One of my favorite questions to ask is, “What’s going well, and what are your latest challenges?” During one conversation, an entrepreneur shared that their company had pivoted to a new product direction and was experiencing tremendous success.

    Curious, I asked what prompted this shift and what customer discovery and feedback had informed it. As we delved deeper, the entrepreneur revealed that the change stemmed from an introduction made by a local startup community leader—a “community super connector.”

    A community super connector is someone who loves people and excels at making thoughtful, value-adding introductions. These individuals are rare and incredibly valuable for nurturing and growing startup ecosystems. They might be venture capitalists, marketing or sales consultants, accountants, or lawyers. Regardless of their industry, they derive value from helping the community and are genuinely passionate about fostering connections.

    These connectors are extraordinarily talented at building relationships and are critical for pollinating new opportunities through introductions. Entrepreneurs would benefit greatly from identifying the community super connector in their city or region. A simple way to find them is to ask a friend, “Who’s the most connected person in the startup community?” Because of their natural inclination to engage, super connectors are eager to meet new people.

    Every startup community has a super connector, and their role is vital in sparking new relationships that drive innovation and growth.