Business

Sean Frank of Cloud Equity Group Shares Tips on Scaling a Small Business

Published

4 years ago

February 3, 2022

Scaling a small business can be a challenge for entrepreneurs. Most businesses reach a plateau and their growth rates diminish and revenue begins to flatten. In this article, Sean Frank, a serial entrepreneur and founder of New York City-based Cloud Equity Group, offers insight on how entrepreneurs can successfully grow their business.

Cloud Equity Group is a strategic capital partner for tech-enabled business service providers. The firm has operational experience in cloud hosting, managed service, and digital marketing. Cloud Equity Group is a hands-on investor with a long history of scaling businesses with decelerating or negative growth rates.

Motivated and Competent Teams

People are the single most valuable asset of any business, especially when it comes to scaling. As Sean Frank puts it, “It’s impossible to do everything yourself. Working with a group of individuals who are as motivated as you are to see the business succeed improves the likelihood of success tremendously.”

It’s natural for an entrepreneur to have the mentality that they can do everything, or that they are needed to do everything. While this can work for a small company, it’s not a productive mindset and it inevitably leads to a bottleneck in a company’s growth trajectory. It can be difficult at first for an entrepreneur to rationalize paying a competitive salary to offload some of their work, and it can be tempting to try to leverage “cheap labor;” however, hiring strong individuals who add value to the business, and align their interests with those of the founder, is an integral part of growing any business. The CEO of a company doing $1M in revenue is likely running and managing most of the daily operations of the business. In order to grow to $10M+ in revenue, the CEO needs to effectively delegate much of the day-to-day management to managers so that they can focus on strategic planning and growth initiatives. It’s a matter of the best use of the entrepreneur’s time. If something can be handled by someone else, particularly if it does not directly translate into growth or value creation, then it should be delegated.

Constantly Adapt the Produce or Service

Businesses are ever-adapting in response to changes in technology, economics, and politics. It’s imperative to be mindful of these changes and to adapt accordingly. As Sean explains, “stale businesses that don’t adapt inevitably die.”

Cloud Equity Group aggressively seeks and incorporates feedback both from customers and employees on how to improve its service offerings. “In my experience,” shares Sean, “company-loyalty improves tremendously when employees or customers recognize that you care. In competitive industries, where customers can easily switch to other providers, it’s vital to show that their feedback is not only welcomed but also acted upon. These two steps go a long way to keep customers happy and for business growth.”

Partnering with Strategic Capital

It can be very tempting for entrepreneurs to accept capital into their business as soon as it becomes available. On one hand, a liquidity event could be seen as diminishing the success available to the entrepreneur. On the other, it may advance short-term funding needs that will, ideally, project the company forward. Accepting capital from an investor is a long-term commitment and it’s important to nurture a strategic capital partner as opposed to accepting any capital that’s available.

For example, a capital partner that’s willing to offer what seems like a lot of money for 50% of your business may be appealing in the short term, however, if the partner can’t help a business double in size, it’s a net loss. Choosing a capital partner that believes in your business, helps solve inefficiencies, and adds value is key. Sean Frank proposes that “it’s always better to have a small piece of a large pie than a large piece of a small pie — especially if that large pie continues to grow.”

Business

Click for Counsel: YesLawyer Wants to Make Lawyers as Accessible as Wi-Fi

Published

7 days ago

April 1, 2026

Matthew Wiles

Photo Courtesy of: YesLawyer

Byline: Andi Stark

For many people facing a legal problem, the most difficult part is not understanding their rights but finding a lawyer willing to speak with them in the first place. Long wait times, unclear pricing, and administrative hurdles often delay even the most basic consultations. YesLawyer, an AI-enabled plaintiff firm operating across all 50 states, is testing whether technology can shorten that gap.

Founded in 2024 by 25-year-old entrepreneur Rob Epstein, the platform offers free intake, automated screening, and, in many cases, same-day conversations with licensed attorneys. The idea is simple: reduce the friction between a client’s first request for help and an actual legal discussion. In this interview, Epstein explains how the system works, where artificial intelligence fits into the process, and what problems the company is trying to address in the broader legal system

Q: When you say you want lawyers to be “as accessible as Wi-Fi,” what does that mean in practical terms?

A: It’s a way of describing speed and availability. Someone dealing with a workplace dispute, a serious injury, or an immigration issue should be able to move from an online form or phone call to a real conversation with counsel in hours, not weeks. YesLawyer is structured so that a client begins with a free case evaluation, goes through automated conflict checks and basic screening, and, in many instances, speaks with a lawyer the same day.

Q: How does the process work once someone contacts the platform?

A: We use a structured workflow. It starts with a short questionnaire and an initial conversation to capture basic facts. That information feeds into conflict checks and internal review. The system then proposes a match with a licensed attorney and provides a calendar link for a virtual consultation, often within 24 hours. After the meeting, the client receives a written legal plan outlining next steps, deadlines, and estimated fees.

Q: Where does artificial intelligence fit into that process, and where does it stop?

A: AI is used for organizing and routing information, not for giving legal advice. It helps with conflict checks at scale, case categorization, and structured summaries so attorneys can focus on the substance of the matter. Every consultation is conducted by a licensed lawyer, and all decisions about strategy or next steps are made by humans.

Q: What problem is this model trying to solve in the current legal system?

A: Delay and cost are still major barriers. Many civil plaintiffs face long waits just to get a first appointment, along with high retainers and hourly billing that make early legal advice risky. We try to respond with faster consultations, flat-fee options, and financing. The idea is to remove administrative friction so lawyers spend less time on logistics and more time speaking with clients.

Q: Some critics say platforms like this blur the line between a technology company and a law firm. How do you describe YesLawyer?

A: We describe ourselves as a national, AI-enabled plaintiff firm that connects clients with independent attorneys. That structure does raise regulatory questions, especially around responsibility and oversight. We focus on licensing verification, attorney-written case plans, and clear communication about fees and services.

Q: You’ve said the main bottleneck is “systems” rather than people. What do you mean by that?

A: The issue isn’t that lawyers don’t want to help more people. It’s that the systems around them make it hard to scale their time. Intake, scheduling, and document handling take hours. Automating those parts means attorneys can handle more matters without being overwhelmed by repetitive tasks.

Q: Does this model risk favoring only the most profitable cases?

A: That’s a real concern in legal technology. Automation often works best for repeatable, high-volume disputes. Our view is that lowering administrative cost can actually make it easier to take on smaller or more complex cases that might otherwise be turned away. Whether that holds over time depends on the data.

Measuring Impact Over Time

YesLawyer’s attempt to compress the timeline between inquiry and consultation reflects broader changes in how legal services are being delivered. As artificial intelligence becomes more common in administrative work, firms are experimenting with new ways to reduce wait times and clarify costs.

The company’s early growth suggests that many clients value faster access to an initial conversation, even before considering long-term representation. Whether this platform-based model becomes widely adopted or remains one of several emerging approaches will depend on regulatory developments, lawyer participation, and measurable outcomes for clients. For now, YesLawyer’s experiment highlights a central question in modern legal practice: how quickly can help realistically be made available to the people who need it.