What is one legal or regulatory hurdle you had to overcome when starting your business, and what advice would you give to others navigating similar challenges? We asked 19 entrepreneurs and small business leaders, and they shared valuable lessons and practical guidance.
- Navigating Licensing and Compliance Requirements
- Getting the Founder’s Agreement Right
- Transitioning from Mortgage Lending to Staffing
- Obtaining Environmental Compliance Certification
- Securing Government Authorization for Immigration Consultancy
- Complying with Data Privacy Regulations
- Ensuring Compliance with Export Control Laws
- Navigating Client Confidentiality Regulations
- Navigating International Shipping Regulations
- Dealing with Copyright Law for AI Content
- Securing FCA Authorization for Mortgage Brokerage
- Navigating Import Regulations for Furniture
- Securing Malpractice Insurance for Personal Injury Law
- Navigating Trademark Laws for International Expansion
- Dealing with SEC Registration Process in Pakistan
- Building Compliance into Investment Management Software
- Navigating Legal and Regulatory Requirements
- Obtaining Necessary Permits and Licenses
- Defining Your Business as a Commercial Entity
How to Overcome Legal Hurdles as a New Business Owner
Navigating Licensing and Compliance Requirements
When I started my business, one of the most critical challenges was ensuring compliance with the legal and regulatory requirements specific to the legal profession. Unlike many other businesses, law firms operate under strict rules governing advertising, confidentiality, and professional conduct. For instance, we had to meticulously review our marketing strategies to ensure they adhered to the ethical advertising rules set by the Washington State Bar Association. Additionally, obtaining the necessary business licenses and setting up trust accounts for client funds required a deep understanding of both state and federal regulations. These processes were time-consuming and required careful attention to detail, but they also reinforced the importance of building a foundation rooted in integrity.
My advice to others facing similar hurdles is to treat compliance as a priority, not an afterthought. Begin by thoroughly researching the regulatory requirements in your industry and jurisdiction, and don’t hesitate to consult with professionals—whether they’re lawyers, accountants, or industry-specific consultants. I also recommend setting up systems early to ensure ongoing compliance. For example, we created a checklist to periodically review marketing materials, client communications, and financial practices to ensure we consistently meet legal standards. While these steps may seem tedious, they save you from costly mistakes down the road and build trust with your clients and stakeholders.
Ed Hones
Attorney at Law, Hones Law Employment Lawyers PLLC
Getting the Founder’s Agreement Right
One of my biggest challenges was getting our founder’s agreement right—I actually messed up by using a template without proper legal review, which nearly caused issues when we brought on our third partner. I worked with a small business attorney who helped us rewrite everything clearly, especially the vesting schedules and exit terms, which cost about $2,000 but was totally worth avoiding future headaches. My advice is to spend the money upfront on proper legal documentation, even if it feels expensive—I’ve seen too many partnerships fall apart over poorly written agreements.
Patrick Carver
CEO, Constellation Marketing
Transitioning from Mortgage Lending to Staffing
Transitioning from mortgage lending to founding my company taught me the importance of robust regulatory compliance in the staffing industry. One significant hurdle was navigating employment classifications and documentation requirements while scaling from local events to multi-state operations serving clients like Ferrari and Louis Vuitton. We invested in AI-powered verification systems that reduced hiring costs from $150 to $50 while ensuring complete compliance.
Our approach to overcoming this challenge focused on three key elements: implementing automated document verification, developing clear standard operating procedures, and maintaining detailed records of all staffing arrangements. This systematic approach proved crucial when expanding our services to include security staffing, requiring additional licensing and certifications.
For others facing similar challenges, I recommend investing in compliance infrastructure early. Our experience shows that building strong foundations—like our AI-powered onboarding system—enables rapid scaling while maintaining legal compliance. This investment has protected our growth from $4,000 to seven-figure revenue while serving high-profile clients across multiple jurisdictions.
Daniel Meursing
Founder/CEO/CFO, Premier Staff
Obtaining Environmental Compliance Certification
When I started my car detailing business, one significant regulatory challenge was obtaining environmental compliance certification. Proper disposal of wastewater and eco-friendly chemical use were required to meet local regulations. Navigating this process was initially overwhelming due to unclear guidelines and the costs involved.
I tackled this by consulting an environmental compliance expert and investing in a water recycling system for my workshop. While the upfront cost was high, it not only ensured I met regulatory requirements but also became a selling point for environmentally conscious customers. Many clients now choose my services because of my eco-friendly approach.
My advice for others is to view regulatory hurdles as opportunities. By complying and exceeding standards, you can turn what feels like a burden into a competitive advantage that builds trust and attracts customers.
Ryan Farook
Owner, Ryans Mobile Car Detailing
Securing Government Authorization for Immigration Consultancy
One of the primary challenges we faced when starting our immigration consultancy in Halifax, NS, Canada, was securing the necessary government authorization. As a regulated industry, immigration consultancy requires a Registered Canadian Immigration Consultant (RCIC) to provide services. Finding a suitable RCIC who aligned with our vision was crucial.
Additionally, staying updated with the ever-evolving Canadian immigration landscape is essential. Government policies and programs can change frequently, impacting the services we offer. For instance, in 2024, there was a surge in invitations for various immigration pathways, while in 2025, the focus shifted towards Canadian Experience Class (CEC) candidates. Adapting to these changes and ensuring compliance with government regulations is paramount.
For those navigating similar challenges, we recommend the following:
- Prioritize Licensing and Certifications: Ensure you have the necessary licenses and certifications to operate legally and ethically.
- Stay Informed: Keep abreast of the latest immigration policies, regulations, and trends through reliable sources like the Immigration, Refugees and Citizenship Canada (IRCC) website and industry news.
- Utilize Data-Driven Insights: Employ tools like Google Trends to analyze search trends and identify emerging opportunities and potential challenges.
- Build Strong Relationships: Cultivate relationships with industry experts, government officials, and other stakeholders to stay informed and seek guidance.
- Adapt to Change: Be flexible and adaptable to changes in government policies and market dynamics.
Following these steps, you can effectively navigate the regulatory landscape and position your business for long-term success.
Paul Abraham
Immigration Consultant, Paul Abraham Immigration Consulting
Complying with Data Privacy Regulations
One main obstacle that every SaaS company faces, especially now that the discussions about it are getting heated, is complying with all the data privacy regulations. They’re fairly new and for most companies, it means they have to adjust their practices mid-way or rethink their launch. It was particularly relevant for us as well since we need quite some user data to provide our service.
So, with the introduction of GDPR, we needed to establish better policies and practices to protect user data. This included multiple adjustments. We had to update our terms of service, introduce user consent forms, and train our team on compliance standards. We were lucky that we had to implement it early on instead of having to completely transform our ways mid-game. That’s why I also advise all companies to take data privacy regulations into account at the very start. This will not only save you unnecessary stress later on, but also create a good reputation and trust amongst your audience.
Oleksii Kratko
CEO at Snov.Io, Snov.io
Ensuring Compliance with Export Control Laws
One significant regulatory hurdle we faced was ensuring compliance with export control laws when expanding into international markets. Navigating the complexities of varying regulations across countries required us to establish a robust compliance framework, including thorough documentation and training for our team on export requirements. Early on, we also sought legal counsel to avoid costly delays or penalties.
This experience taught us the value of proactivity—research regulations specific to your industry and markets well in advance, and don’t hesitate to consult with experts. My advice: treat compliance as a strategic priority, not just an administrative task. Doing so will protect your business and lay the groundwork for sustainable growth.
Elia Guidorzi
Marketing Executive, Techni Waterjet
Navigating Client Confidentiality Regulations
Navigating the stringent client confidentiality regulations was a significant hurdle when starting our practice. We had to implement sophisticated IT systems and internal protocols to ensure that all client information was stored and accessed in compliance with the Law Society of Alberta’s guidelines. This required a substantial upfront investment in secure technology and training to protect client data effectively.
For those dealing with client confidentiality regulations, I advise investing in top-tier IT infrastructure and ongoing staff training. Ensuring that everyone in your firm understands the importance of data security and is equipped to maintain it is crucial for compliance and client trust. Regular audits and updates of these systems can help mitigate risks associated with data breaches.
Jeffrey A. Preszler
Partner, Preszler Law Alberta
Navigating International Shipping Regulations
Launching an online retail business threw a unique challenge our way: international shipping regulations. Navigating through varying customs laws can be overwhelming. Each country has its own set of rules regarding the import of textiles, which isn’t something everyone anticipates. Understanding these differences and ensuring compliance is crucial. Ignoring them can lead to delays, fines, or even seizure of goods.
A lesser-known, yet effective, approach is partnering with logistics experts who specialize in your industry. These partners often have insider knowledge of international customs laws and can help ensure your products move smoothly across borders. Beyond that, investing in a reliable customs broker can save you from these shipping headaches. They manage the necessary documents, tariffs, and can offer advice on the best practices for reducing duties legally. This allows you to focus on other areas of your business, confident that the shipping aspect is in good hands.
Jean Chen
COO & CHRO, Mondressy
Dealing with Copyright Law for AI Content
One of the major legal hurdles that we faced concerns the copyright law for the contents that AI will create. Many academic books are totally copyrighted, which would mean applying AI to make it audio format was an impossibility, at least related to derivative works and fair use. The legal terrain was very ambiguous in that context, particularly about any precedent on how the transformation via AI may work with respect to current copyright principles.
This, however, was overcome by hiring intellectual property attorneys who looked into our approach, ensured explicit permissions and licenses from publishers and authors, and developed a compliance protocol wherein every piece of content that passed through our platform had to do so under the requirements of the law.
Always suggest that people be proactive when dealing with legal ambiguity of emerging technologies. Do not assume that the innovation is going to exempt you from regulation. Consult your lawyer early, secure necessary permission, and stay informed about legislative developments in your industry to protect your business and build trust with stakeholders.
Derek Pankaew
CEO & Founder, Listening.com
Securing FCA Authorization for Mortgage Brokerage
As the founder of a mortgage brokerage, we needed to be directly authoriaed by the FCA (the UK regulator). To do this, you need significant capital to justify your longevity as a business for the customers you’ll be helping—so, we needed to turn to investors to raise funds.
However, another option is to become part of an authorization network—this means you don’t require the capital, but you’ll pay for the privilege, and you’ll need to play with their rulebook.
My advice is to have the bravery to fully commit to your ambitions. Sometimes the more difficult option is worth it in the long run, even though it’s hard to see past the convenience of a shortcut.
Being able to act with autonomy through our own independence has been beyond worth it, and taking the easier option could have held us back more than we’ve grown. Do it your way, and do it the right way.
Luther Yeates
Co-Founder, UK Expat Mortgage
Navigating Import Regulations for Furniture
When I started my business, one of the biggest hurdles was navigating the complex regulations around importing furniture. Understanding tariffs, customs duties, and product safety standards was a steep learning curve. I had to confirm that all our products met U.S. safety regulations, which involved a lot of paperwork and compliance checks.
I advise anyone facing the same challenges to do your homework and seek expert advice early on. Work with a good customs broker or legal advisor specializing in international trade. They’ll help you avoid costly mistakes and ensure everything is in order. It can be overwhelming, but it is vital to break down the process step by step and stay organized. Your effort to get the legal side right will pay off in the long run.
Chris Putrimas
CEO, Teak Warehouse
Securing Malpractice Insurance for Personal Injury Law
Securing malpractice insurance at a feasible cost was a hurdle, given the high-risk nature of personal injury law. We had to navigate the complex insurance landscape to find a policy that would provide ample coverage without constraining our financial resources, which was crucial for safeguarding our practice and our clients’ interests.
In securing malpractice insurance, it’s beneficial to shop around and negotiate terms that meet your specific needs without overpaying. Consider factors beyond the premium, such as the extent of coverage, the reputation of the insurer, and the support services they offer, which can be invaluable in times of need.
Jason B. Javaheri
Co-Founder & Co-CEO, J&Y Law
Navigating Trademark Laws for International Expansion
In Estonia, starting a business is fairly straightforward, but expanding internationally exposed us to a maze of trademark laws. Protecting our brand name “Toggl” across regions meant spending time and money we hadn’t planned for early on. It was a lesson in being proactive about intellectual property from day one.
Think long-term when it comes to legal protections like trademarks and IP, even if it seems overkill in the early days. As your business grows, these will become assets that save you from endless headaches. Protecting your brand now is much easier than fighting for it later.
Alari Aho
CEO and Founder, Toggl Inc
Dealing with SEC Registration Process in Pakistan
The major legal barrier I met at the very step of launching my venture was to deal with the registration process related to the Securities and Exchange Commission of Pakistan, which imposed a quite complex procedure upon the applicant. This included determining which form of legal structure would be the most suitable, such as an LLC or a private limited company. Among other requirements for documentation, I had to submit proof of my identity, a memorandum of association, and articles of association.
It was quite daunting, considering the intricacies involved in navigating the regulations and the need for precise documentation. I consulted with professional legal advice early, and this guidance proved indispensable in guiding me towards the appropriate business structure and ensuring compliance with all required regulations from the very beginning.
My advice to others facing similar circumstances is that they would first like to understand the legal framework that refers to their business. Work with a qualified attorney or consultant that handles business law in your area. This will help you through the registration process and ensure compliance. These steps will save time and potential problems later on. Most importantly, know that regulatory changes have to be updated; thus, staying abreast of current issues is essential to industry newsletters, attending local business groups, and getting ongoing support and insight. By taking these steps before the occurrence, you will lay down solid groundwork for your business and prevent future legal risks.
Sheraz Ali
Founder & CEO, HARO Links Builder
Building Compliance into Investment Management Software
Our investment management software and investor portal are designed to help Commercial Real Estate Private Equity firms stay in compliance with complex regulatory requirements. Given the critical nature of compliance for our clients, we faced the challenge of building a product that not only met our clients’ needs but also adhered to industry-specific regulatory standards.
Advice for others navigating similar challenges:
- Seek expert legal counsel: Partner with top-tier attorneys who specialize in your industry. Regulatory landscapes can be nuanced and require specialized expertise. Don’t rely on a single counsel—having multiple experts can provide a broader perspective.
- Invest in compliance early: Avoid shortcuts. Taking the time to build a product or service that meets all legal requirements will save you from costly revisions, penalties, or reputational damage later on.
- Prioritize education and alignment: Ensure your team understands the regulatory requirements and how they impact the product. This alignment minimizes missteps and helps create a compliant product from the start.
- Regularly review and adapt: Regulatory environments evolve. Build processes to regularly review your compliance measures and adapt your product to meet new standards.
By addressing compliance proactively, we turned a potential obstacle into a competitive advantage, building trust and credibility from day one.
Ameet Mehta
Co-Founder, SponsorCloud
Navigating Legal and Regulatory Requirements
One major hurdle I faced when starting my business was navigating the legal and regulatory requirements. Despite having extensive experience in business strategy and management, I realized quickly that the legal side was a whole different ballgame. From choosing the right business structure to understanding tax obligations, it was an entirely new area for me, and I found it overwhelming.
My advice is: don’t try to figure it all out on your own. Lean on experts like attorneys or tax professionals who specialize in small businesses. They can guide you through these processes efficiently and help you avoid costly mistakes. It’s okay not to know everything-sometimes the best strategy is knowing when to call in the right help.
Inbar Madar
CEO and Business Consultant, M.I. Business Consulting
Obtaining Necessary Permits and Licenses
One legal or regulatory hurdle that many entrepreneurs encounter when starting their own business is obtaining the necessary permits and licenses to operate. This can be a daunting and time-consuming process, but it is crucial to ensure that your business is operating within legal boundaries.
In my experience, one of the biggest challenges was understanding which permits and licenses were required for my specific type of business. Each industry and location may have different regulations and requirements, so it’s important to do thorough research or consult with a legal professional to ensure compliance.
My advice as a business lawyer would be to start early in the process of obtaining permits and licenses. It’s important to factor in potential delays or complications, so giving yourself ample time will help avoid any setbacks in getting your business up and running. Additionally, make sure to keep thorough records of all the applications and approvals you receive, as well as any fees or payments made. This will help in case of any future audits or inquiries.
Amira Irfan
Founder and CEO, A Self Guru
Defining Your Business as a Commercial Entity
One of the more important legal or regulatory hurdles to overcome when starting a business is to clearly define your business as a commercial entity and a personal one. So many of us start businesses in our home with a cell phone as our primary service. However, regulators, who are on the lookout for fraud, flag that as suspicions. A land line and a commercial address goes a long way.
B Randall Willis
Founder, Right Angle
