Category: Entrepreneurship

Once or twice a month, I’m introduced to someone who wants to plug into the local startup community. Sometimes it’s a person new to town. Other times it’s someone who has been here for a few years, heads down in their work, and is now at a career crossroads. And occasionally, it’s someone who’s simply curious about startups.

When I meet with them, I always start by trying to understand their intentions. Why do they want to connect with other entrepreneurs? Are they looking to make money? To give back? To become an entrepreneur themselves and start building a peer group? Or do they have other motives? You can never be entirely sure, but after doing this for years, I usually get a pretty good sense of someone’s intentions.

Once I understand the why, I like to dig into their areas of interest. This could be specific industries or technologies—software, hardware, robotics, cloud, AI—or even the size and stage of startups they’re drawn to. Some people love the energy of the idea and seed stage, when things are the messiest. Most, however, prefer companies that are a little further along—likely post–product-market fit, with $1–10 million in revenue. There’s no right or wrong answer, but it’s a helpful data point in understanding where their curiosity lies.

Next, I ask about their process so far. Who have they talked to? What events have they attended? Which organizations are they curious about? What startups seem most interesting to them? Part of this is my own curiosity about how people find their way into a community, and part of it is to gauge their current progress so I can offer relevant advice or introductions.

Finally, after all the questions and conversation, I share recommendations. Usually it’s a mix of checking out the websites of local coworking spaces and incubators, attending venture conferences or meetups, and connecting with specific entrepreneurs and executives I know. I try to introduce them to people who enjoy meeting newcomers and who would be a good fit based on what I’ve learned.

Plugging into a local startup community should be relatively easy with the right amount of effort. Entrepreneurs are, by nature, glass-half-full types who enjoy paying it forward. In fact, that’s one of the things I love most about them: they see potential in the world and choose to create, build, and persist in the face of adversity. That same “can-do” attitude extends beyond their own ventures and into helping others along the way.

Last week I was talking to an entrepreneur who had built a solid business, growing modestly with plenty of room to run. During the conversation, the question came up about whether or not to raise institutional capital.

Over the past several years, the startup has raised a few angel rounds and some debt from angel investors. That capital provided the necessary resources and team to get the product to market, develop strong distribution channels, and scale to millions of dollars in revenue. However, the investor base doesn’t have the financial capacity to continue funding losses, so the business has been mostly self-sustaining.

The idea, of course, is to grow faster and enter new markets. But without more capital, growth will be limited.

Benefits of Not Raising Institutional Capital

Some of the benefits of not raising institutional capital include:

• Liquidity flexibility. If the company continues to grow and becomes highly profitable, investors would welcome dividends. The current capital is patient and has no exit timeline.
• Longer-term decision making. Without pressure from institutional investors, the entrepreneur feels freer to make decisions that benefit the company long-term, rather than hitting short-term, potentially artificial milestones.
• Strategy changes. If a new strategy or idea comes along, it’s easier to shift the business and go a different direction. Most investors, when something is working, don’t want to avoid new risk.

Benefits of Raising Institutional Capital

On the other hand, raising institutional capital offers significant advantages:

• Limitless capital. Assuming the business performs well, there’s abundant capital available for companies at scale with strong growth prospects. Despite the perception that capital is scarce, at the right stage it actually becomes plentiful.
• Fuel for growth. Additional capital allows for new hires, product development, geographic expansion, acquisitions, and more aggressive growth. While some markets pull you in naturally, many require pushing hard to build share quickly.
• Credibility and visibility. Once you’re in the system, there are conferences, summits, speaking opportunities, and broader recognition that come from having institutional investors’ stamp of approval. Even raising a small amount gets you on the radar of larger investors down the road.

The Entrepreneur’s Choice

There’s no right or wrong answer when it comes to raising institutional capital. The best approach for an entrepreneur is to be intentional and consider personal and team goals and aspirations.

Some want to swing for the fences and build the biggest company possible. Others want to balance lifestyle, flexibility, and control.

The next time an entrepreneur says they’re going to raise institutional capital, encourage them to carefully enumerate the pros and cons, and make sure the decision is thoughtful.

Last week I was catching up with an entrepreneur who was thinking about doing some angel investing, and he asked me what I look for in other entrepreneurs. Over the years, I’ve had the opportunity to work with many great people and learn from their experiences. Entrepreneurship is not a one-size-fits-all journey, but I’ve found some common characteristics that show up again and again in successful entrepreneurs.

1. A Desire to Improve

There are constant ups and downs in entrepreneurship. One moment you’re high-fiving your co-founder after signing a new customer, and the next a key employee leaves and you just want to curl up and cry. The entrepreneurs who succeed have a deep desire to improve. They want to learn, grow, figure out what works and what doesn’t, and take lessons from others who have gone before them. This thirst for learning is a key trait.

2. A Unique View on Risk

Many people see starting a new venture as too risky. Entrepreneurs, on the other hand, often have enthusiasm for calculated risk, especially risks that look uncertain or unlikely to succeed to the average person. They either have a unique angle or an unusually strong belief that they can overcome the challenges. This different perspective on what is and isn’t risky is a defining characteristic.

3. A Chip on the Shoulder

Almost every entrepreneur I’ve worked with has had some compelling drive or unusual background that pushes them to prove themselves in an extreme way. The old saying holds true: chips on shoulders equal chips in pockets. In other words, entrepreneurs with something to prove often end up creating significant value for themselves and their investors.

4. MacGyver-Level Resourcefulness

Resourcefulness is another common trait. The best entrepreneurs love to “MacGyver” their way into opportunities, finagling introductions, connecting seemingly unrelated dots, and figuring out how to make progress when others would stop. Whether it’s landing a first customer, solving a daunting problem, or raising a round of funding after many rejections, this tenacity and creativity greatly increase their chances of success.

5. A Glass-Half-Full Outlook

Finally, successful entrepreneurs tend to believe they can change the world, an industry, or even a city. This optimism, sometimes born from blissful ignorance, helps sustain them when progress is slow, opportunities are scarce, or things are going wrong. A positive outlook creates space for unexpected magic, where unexplainable good outcomes seem to come together at just the right time.

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These five characteristics—desire to improve, unique view on risk, chip on the shoulder, resourcefulness, and optimism—are some of my favorites when it comes to entrepreneurial success. There’s no guaranteed formula and no single path, but these traits consistently show up in entrepreneurs who make it.

If you’re thinking of becoming an entrepreneur, or considering partnering with or investing in one, keep these characteristics in mind. Evaluate them against the entrepreneurs you’ve met in the past. You’ll likely see these traits reflected in those who have succeeded.

Last week, I was talking to an entrepreneur who is building a new business. The company has some decent traction, and he’s deciding what to do next on the fundraising side. As part of the discussion, one important consideration that came up was how to think about a competitor recently raising a large round of funding.

Historically, in startups, funding is often used to achieve a new milestone. For example, going from $5 million of revenue to $10 million of revenue in a short period, fueled by outside capital. Once that milestone is hit, another round is raised, and the cycle continues as the business scales. But in the age of AI, scaling certain startups has become dramatically faster, and the perceived market opportunity is much larger. As a result, startups that previously would have raised amounts more in line with their run rate and growth rate are now raising many multiples of what used to be normal at valuations dramatically higher than in the past.

For entrepreneurs, especially in the context of competition, my recommendation is to always be market-aware and customer-focused. It’s easy to get distracted by competitor announcements, product launches, or flashy initiatives. But the most important thing is to listen closely to customers and build an opinionated vision of the future that you believe is right. That said, when you’re thinking about raising X dollars for the next round and you see a competitor raise 10X what you were considering, it naturally creates some consternation.

The Pros of Raising a Large Round

On the benefit side, the obvious one is having cash in the bank. A strong balance sheet enables more experiments, funds more initiatives, and gives the company breathing room. There’s a lot of advice out there about not needing to spend the money just because you raised it. But in practice, human nature pushes toward deploying that capital quickly, usually within 12 to 24 months, because it feels better to be aggressive and proactive rather than conservative and reactive.

Another major benefit of raising at a high valuation is the perceived value of equity for recruiting. For example, if you have an employee option pool of 10% and your last round valued the company at $50 million, that pool is worth $5 million on paper. If instead the last round valued the business at $200 million, even with identical metrics, that same pool is now worth $20 million. That makes it far easier to recruit top talent when you can offer an engineer $500,000 in paper equity value instead of $125,000, while giving up the same ownership percentage. The last round’s valuation acts as a powerful marker in the recruiting process.

The Cons of Raising a Large Round

On the downside, the higher the valuation, the higher the expectations. Growth investors typically want 3–5x their money, and elite VCs are often looking for 100x outcomes. Raising at an inflated valuation means the eventual exit or IPO must be correspondingly larger for everyone to be satisfied.

Another challenge is that the bar for the next round is dramatically higher. If you raise at an unusually high valuation and then need more money in 12–24 months, it can be demoralizing to face a down round. Down rounds often trigger negative side effects such as pay-to-play provisions or liquidation preferences, which can cause real pain inside the business.

Final Thoughts

When competitors raise large rounds, entrepreneurs should take the time to do some soul-searching about their own level of ambition. Do you want to “go big or go home,” or are you comfortable being the number two or three player in the market? Many markets are not true winner-take-all environments. More often, they resemble oligopolies or are divided into valuable niches where multiple players can thrive.

Just because a competitor raises a massive round doesn’t mean you need to. But it is prudent to carefully weigh the pros and cons instead of reacting impulsively. There are many paths to building a successful business, and not all of them require raising huge sums of money.

Last week I was talking with an entrepreneur about financing options and the current fundraising climate. One of the topics that came up was customer value financing, an idea I first explored a couple of years ago.

Customer value financing works like this: an investment company provides capital for sales and marketing efforts to acquire new customers. In exchange, the company receives a percentage of that new revenue until they are paid back, plus an equivalent of an interest rate. It is a form of non-dilutive financing that is not debt. Instead, it is essentially buying the right to a percentage of new revenue generated until a formula representing the desired return on investment is reached. Unlike traditional revenue financing, it is not a loan against the entire business and it does not claim existing revenue.

General Catalyst first popularized the idea a few years ago and has since raised and deployed capital using this model.

When I shared the concept with the entrepreneur, he had never heard of it. That prompted me to do some research, and what I found was surprising: the industry around customer value financing is basically nonexistent. I could be using the wrong terminology, and there may be capital providers offering similar structures under different names, but I was not able to find them.

That led me to ask why a market has not emerged to meet this need. After thinking about it, my conclusion is that startups already have access to traditional venture debt from banks and private credit providers like Conductor Capital. For entrepreneurs who qualify, venture debt works well. It is also much simpler to explain: “Here is a loan for X million dollars, and here are the terms.” You take the money and run your business.

By contrast, customer value financing, while arguably more aligned with growth-stage entrepreneurs’ goals, requires additional overhead. Defining, negotiating, auditing, and tracking incremental customer acquisition costs and resulting revenue adds a layer of complexity that does not necessarily change what entrepreneurs want to accomplish.

That said, seeing General Catalyst continue to announce new customers for its customer value financing program shows that at the high end of the market, with larger deal sizes, the model does fill a gap and attract demand.

Hopefully, over time, more providers will enter the space with variations of customer value financing. Entrepreneurs deserve more options and potentially better-aligned solutions for their growth. For now, there are still plenty of venture debt opportunities available, and entrepreneurs should evaluate them carefully in the context of their financing goals.

It’s that time of year again. The new 2025 Inc. 5000 awards list is out, and once more, a number of great Atlanta companies are represented. I always enjoy digging through the list, both to see the local standouts and to explore companies from across the country. It’s a great way to spot trends, spark new ideas, and understand what’s gaining momentum. The Inc. 5000 offers a broad perspective on where the economy is headed and what’s hot right now. Every entrepreneur looking for their next idea should pore over it.

Here are the Atlanta tech companies on the 2025 Inc. 5000 list.

No.166 Anaptyss 

Enabling financial institutions worldwide through full life cycle evolution of tasks and processes.

https://www.anaptyss.com/

No.293 Centegix 

Provider of incident response solutions, creating safer public spaces to protect people.

http://centegix.com

No.375 Financial Cents 

Company offering a practice management software built for accounting and bookkeeping firms.

http://financial-cents.com

No.424 Viva Finance 

Lending platform providing overlooked consumers credit based on metrics beyond their FICO scores.

http://viva-finance.com

No.474 ElastiFlow 

Network performance and security company developing open data platforms with monitoring tools.

https://www.elastiflow.com/

No.488 Flock Safety 

Hardware and software suite helping communities with crime prevention and security.

http://flocksafety.com

No.490 Ratings MD 

A platform helping patients find doctors by making verified ratings and reviews easy to find.

http://ratings.md

No.808 Cognosos 

A cloud-based real-time location systems company offering effective and inexpensive solutions in the health care, automotive, logistics, and manufacturing industries.

http://cognosos.com

No.851 adtechnacity 

Offers a fully managed native advertising platform that runs campaigns across the native advertising space to maximize both reach and ROI without being beholden to a single publisher network and limitations.

https://www.adtechnacity.com/

No.1,045 PadSplit 

A creator of a co-living market platform enabling workers to live in the communities they serve.

http://padsplit.com

No.1,163 SmartPM Technologies 

Provides data management and analytics software to construction stakeholders to help them interpret their data, improve performance, and minimize risks.

https://smartpm.com/

No.1334 Katalon 

Provides a comprehensive quality management platform, enabling teams to deliver world-class customer experiences faster.

https://katalon.com/

No.1,501 Mile Auto 

A B2B2C pay-per-mile insurance provider that provides lower mileage drivers with insurance based miles driven.

http://mileauto.com

No.1,579 Verusen 

An MRO intelligence provider helping manufacturers streamline their supply and materials management strategy to reduce risk, optimize capital, and ensure uptime.

http://verusen.com

No.1,590 Brightwell Payments 

A financial technology company solving payroll challenges in the cruise industry and enabling embedded cross-border payments.

http://brightwell.com

No.1,795 Polygon.io 

Develops a real-time financial data platform that displays stocks, forex, and cryptocurrency data, enabling clients to build APIs efficiently.

http://polygon.io

No.1,802 SingleOps 

Offers business management software for outdoor services from landscaping to tree care that grows revenue, increases profitability, and improves customer satisfaction.

http://singleops.com

No.2,033 SafelyStay 

Protects short-term home rentals with rigorous guest screening and comprehensive commercial insurance coverage embedded directly into the booking process.

http://safely.com

No.2,155 Voxie 

Offers an SMS platform purpose-built for franchises, empowering brands to connect directly with their customers and drive meaningful, measurable growth.

No.2,316 Wick 

A technology company whose mission is to accelerate the transition to AI-powered solutions in the B2C marketing ecosystem.

http://wick.io

No.2,449 Cogitate 

A software company that digitizes insurance processes, helping carriers and program administrators transition to cloud-native core policy, billing, and claim applications.

http://cogitate.com

No.2,540 RoadSync 

Offers payment products for warehouses, carriers, brokers, repair/tow merchants, and drivers, integrating and automating the financial systems fueling the logistics industry.

http://roadsync.com

No.2,681 IRONSCALES 

An email security solutions provider integrating AI and human insights to address phishing threats and advanced attacks like impersonation.

http://ironscales.com

No.2,965 Groundfloor 

A wealthtech company making real estate investing easy, known for its regulatory prowess and developing new financial products for retail investors.

http://groundfloor.com

No.3,276 Trella Health 

A data analytics software company focused on performance visibility, enabling health care organizations to improve outcomes and reduce costs.

http://trellahealth.com

No.3,615 Gain Servicing

Offers an AI-enhanced LOP servicing platform, integrating financial solutions for health care providers, personal injury attorneys, and plaintiffs.

http://gainservicing.com

No.3,819 FullStory 

A digital experience intelligence platform that enables businesses to improve their digital products and experiences across sites and apps.

http://fullstory.com

No.3,955 FinQuery 

Empowers experts with tools for smarter fiscal decisions on leases, software subscriptions, and financial contracts.

http://finquery.com

No.4,011 OncoLens 

A clinical decision support company connecting data and care teams for better cancer treatment plans.

http://oncolens.com

And many more Atlanta tech companies.

Congratulations to all the Inc. 5000 award winners!

Last week, I was reminded of the importance and value of being around other founders who believe the impossible is possible.

When I was first starting out, I would read the local paper and business journals, looking for any articles about startups in the area. If I saw that an entrepreneur had launched a new business or raised money, I would reach out and ask them to lunch. Most of the time, I never heard back, but occasionally, an entrepreneur would respond and agree to meet. I wanted to understand how they did it. I wanted to know what they had learned, what they knew now that they didn’t know before. In hindsight, I also realize I wanted to be around someone who believed so strongly in their vision that they were willing it into reality.

When we first opened the Atlanta Tech Village over a decade ago, we knew there was value in entrepreneurs helping other entrepreneurs—from casual hallway conversations to more formal programs with mentors and speakers. By bringing like-minded entrepreneurs under the same roof, they naturally help one another and increase everyone’s chances of success.

But even with that, there’s another element that’s easily overlooked: the belief that you can create something from nothing, even when everyone is telling you otherwise. Doing it alone is possible, and it’s been done many times. But building your company alongside others who are building theirs, in a community that’s striving to do the impossible, is incredibly valuable.

The more you talk with the entrepreneur down the hall who believes in her business and her ability to make it work, the more your own mind starts saying, “I can do it too.” It’s like a phenomenon where you might never have considered it if you hadn’t been exposed to it—whether it’s entrepreneurship in general, the concept of venture capital, or taking a company public. When you see and hear someone actually doing it, especially in person, your brain lights up and says, “Wait a second… they’re just like me. We breathe the same air. We live in the same city. I can do it too.”

My recommendation for entrepreneurs: be around other entrepreneurs. Find the big dreamers. Find the ones with the deepest belief in what they’re building. Being an entrepreneur is hard; being an entrepreneur without a community is ten times harder. Belief is contagious, and surrounding yourself with entrepreneurs who believe will help unlock a greater level of belief in yourself.

Last week, I was talking to a would-be entrepreneur, and the usual questions came up about my personal experiences, background, and philosophy. As I thought about how to emphasize a key point, I shared that my favorite word when it comes to entrepreneurship is permissionless.

Permissionless—while not a word used often in everyday conversation—captures the ethos of entrepreneurship so well. The term comes from the Web3/blockchain world and refers to a protocol that is accessible to everyone without restriction, meaning no prior permission is required.

Entrepreneurship is the science and art of creating something from nothing that someone else wants. The key aspect is that “something from nothing” moment. Think about the great entrepreneurs of our time: they didn’t ask permission to create a new search engine, to invent a new way to connect with friends, or to set up an online bookstore. Permissionless captures the idea that you can simply act. You can create new products. You can launch new services. While it’s true that someone must eventually want to buy or use what you make, you don’t need their permission to prototype, test, and refine it.

There’s another element of permissionless thinking that resonates with me: risk-taking. My favorite way to describe it is this—most people overestimate risk and underestimate opportunity. If you’re constantly seeking permission to try new things or explore new opportunities, you’ll inevitably encounter resistance from decision-makers who are focused on the path they’re already on.

When taking risks—especially those most people consider “too risky”—you need even more permissionless thinking. Human nature drives us to seek approval from others: peers, colleagues, mentors. But when you step outside the bounds of generally accepted risk tolerance, you have to be willing to proceed without that approval. It’s not that people don’t want you to take risks; rather, they want you to be successful and to follow a path that has worked for them and the people they know. The problem is that the biggest opportunities often lie outside those well-worn paths.

So the next time you think about startups and innovation, I hope one of the first words that comes to mind is permissionless. No permission required to invent the future. No permission required to start a business. Build a permissionless mindset—and create something from nothing.

Last week, I spoke with an entrepreneur whose company is growing at a pace that goes beyond even traditional hypergrowth standards. I’ve read about companies like Replit and Lovable going from $0 to $100 million in revenue in under a year, and coming from a more traditional SaaS background, that level of growth seems almost unfathomable.

We used to look at the “triple-triple-double-double-double” model as the blueprint for companies that reached escape velocity, went public, and had strong outcomes. But now, we’re seeing businesses grow so rapidly that they break all the previous paradigms.

When speaking with this entrepreneur, I asked the usual questions:

• What’s your renewal rate?
• What’s your upsell and cross-sell rate?
• What are your gross and net dollar retention numbers?
• How do you segment your cohorts—are some just kicking the tires while others are serious adopters?
• What’s the meta-analysis of your customer base?

The answer, unsurprisingly, was: “We don’t really know yet.”

The growth has been so fast, and customers have been onboard for such a short time, that it’s hard to gather meaningful data. While the goal is to eventually apply all the traditional best practices and quantitative frameworks, it’s nearly impossible to do so in the early stages of this kind of explosive growth.

We also talked about valuation and funding needs, and another fascinating insight emerged: the company doesn’t really need more capital—at least not in the traditional sense. The growth primarily demands more foundational AI model and hosting capacity. Thanks to AI in other parts of the business, many functions like customer success, support, and sales are handled with an incredibly lean team. Because of that, and the fact that the business is already highly profitable, there’s no urgent need for outside funding.

Never having personally experienced this level of warp-speed growth, my advice was simple: stay as close to the customer as possible. Get on the phone. Do the Zooms. Meet in person. Listen to their feedback—not just through support tickets and customer success notes, but by actively engaging with them directly.

One of the biggest questions in situations like this is about the durability of the revenue. If tens of thousands of customers can sign up out of nowhere and get immediate value, they could also just as easily churn and move to the next shiny tool. There’s a massive amount of work to be done to ensure that customers receive unique value that can only be delivered by your product. That means building deep integrations into the rest of the customer’s ecosystem so the product becomes a critical, embedded part of their workflow—not just a standalone app.

Overall, this kind of growth isn’t just hypergrowth—it’s something even more dramatic. But regardless of the growth rate, the core principles remain the same:

• Stay close to the customer.
• Build opinionated functionality for your ideal user.
• Deliver something they couldn’t do before your product existed.

Growth of this kind is rare, but I hope more entrepreneurs get the opportunity to experience it. And no matter how fast the business grows, the ultimate goal stays the same: to deliver real, lasting value to your customers—not just today, but well into the future as they continue to evolve alongside your product.

As I look out my window this morning, I can’t help but smile watching my robotic lawnmower carve pictures and words into the backyard. Of course, the artwork is silly and there for fun, but the aha moment for me—as a kid who grew up in the Deep South mowing grass for hundreds of hours in 90°-plus temperatures—is that I can’t help but be thankful and optimistic for the impending wave of robots coming into our lives. Now, we’ve had simple robots for a couple of decades doing productive tasks. The Husqvarna could bounce between a buried low-voltage wire and mow the grass. The Roomba could bounce around the house doing basic vacuuming. Now, the big unlock is a combination of processing power, computer vision, GPS + RTK, ubiquitous internet, battery capacity, and miniaturization of electronics, all combined with a supercomputer in our pockets. Now that the robots can see, think, and act in a more human-like manner, the new possibilities are endless. Robots will soon be everywhere.

Last week, we did a road trip of a couple hundred miles. I simply put the destination in my Tesla, and Full Self-Driving took us the entire way—from stoplights to interstates to navigating tight downtown roads. The entire experience was flawless. The robot—in this case, my car—did all the heavy lifting, and I was merrily along for the ride. With an experience that good, I can’t see ever buying a car again without that functionality. Just like pushing that lawnmower, doing a repetitive task was a poor use of time; driving a car feels antiquated and a waste of effort. The robot drivers are more alert, monitoring all 360°, and never get distracted. It’s both safer and more efficient. The next time you have an opportunity to experience a Waymo or Tesla, try it out and experience it for yourself.

For entrepreneurs thinking about their next idea, my recommendation is to research the robotics space. Talk to companies and ask how they might use robots in their business. When researching, consider both the creation of new robots and all the businesses that will be built to install, manage, service, and finance them. Robots will soon be ubiquitous, and thousands of new startups will be created in the process.