Lorraine D’Alessio

Building your trusted A-team requires you to understand both you and your company’s strengths and weaknesses and hiring to fill those gaps in expertise.


Founder of D’Alessio Law Group, Lorraine D’Alessio was named the 2017 Leader in Law by the Los Angeles Business Journal and is the recipient of the 2018 Enterprising Woman Award. A former Ford model turned legal powerhouse, Lorraine is a multi-award-winning, immigration expert that regularly contributes to the Los Angeles Times, The Hollywood Reporter, LA Business Journal, Playback and other leading outlets in the U.S. Lorraine serves on the board for Artists for Change and is the author of “Going Global: Investing in U.S. Immigration,” a highly anticipated guide to U.S. immigration expected to be published later this year. Lorraine has provided counsel to hundreds of prominent and award-winning entertainment agencies, unions, private companies, academic institutions, tech startups, entrepreneurs and enterprises including: Next Models, Food Network, SubPac, Pepperdine University, ACTRA, New York Film Academy, Plug and Play, Expert Dojo, and 500 Startups. In addition to these clients, Lorraine has worked on highly successful refugee and deportation cases earning awards for her work with immigrant communities across Los Angeles.

Lorraine D’Alessio earned her law degree from Southwestern Law School. She earned her master’s degree in public administration from The Senate of Queen’s University at Kingston and also attended the University of Toronto, Canada to earn her undergraduate degree with a Bachelor of Arts.

Where did the idea for your company come from?

My husband [Richard D’Alessio] and I worked in industries where there are a lot of extraordinary people across the digital, tech, and entertainment communities. When we immigrated to the United States from Canada, we learned about the extraordinary abilities visa route, also known as the O-1B visa, and realized that so many people we worked with not only were perfect candidates for this visa, but also had absolutely no idea this option even existed.

Throughout law school I kept paying attention to the U.S. immigration law community, which at the time was very small. I started interning at an immigration law firm and was introduced to the community, and soon after I realized that there was a tremendous need for a dependable immigration route for those working in entertainment and tech. Most people are only familiar with other visa options, notably the H-1B and L visas, which can be incredibly demanding for some people. Throughout law school many friends reached out to me for help because of my understanding of the visa process.

Soon after graduating I founded D’Alessio Law Group alongside veteran attorney and mentor Thomas Joy. Thomas was close to retiring at that time but helped me immensely in those early days. He helped me grow my team and my understanding of immigration law, and I will always be thankful for his insight and dedication. He didn’t need to go out on a limb for me in those early days, but I think he recognized a similar drive in me that had inspired him when he was getting his start.

D’Alessio Law Group stemmed from a need. Most people don’t know or understand the visa process, and as a result, countless international professionals miss out on the opportunity of entering the U.S. market because the process is intimidating. My hope is that my work can help break that initial barrier down for our clients, and that our team can help them with creative solutions for the challenges they face.

What does your typical day look like and how do you make it productive?

Lately I’ve been waking up earlier to fit a jog into my morning. I find that getting that energy out carries me throughout the day. I wake my children up and focus on making breakfast and lunch for them, and helping them get dressed and out the door. I might take a call or consultation over the phone with our European clients before driving the kids to school.

Throughout the day I’m usually tackling a number of things. It really depends on what is going on. I balance my work as a lawyer while also planning strategy on our immigration cases, managing the direction of the firm, and coordinating on a number of items with our operations and human resources team. I am by no means an expert on that side of the business, but I am very collaborative with my employees and listen to their insight with every piece of action required from us as a firm.

Afternoons I’m usually balancing these responsibilities alongside meetings with current and potential clients. If we are traveling for speaking events or immigration presentations to tech and entertainment groups, the days obviously run a bit differently.

I usually stay in the office pretty late. I am usually home by 9pm on most days, though if we are at an event or traveling, I am known to work into the wee hours of the morning. At home I balance my time as a mom and as a business leader and am usually still working up until I go to bed.

How do you bring ideas to life?

I’ve never done anything in my life without a team. Having an inner circle of people who I can delegate action to and trust is essential to my success.

Together we conceptualize strategy and ideas. I offer my insight and listen to my team’s feedback. I’ve learned throughout the past decade to be humble with your ideas, to be ready to receive criticism, and to be prepared to make a change when someone sees a more effective way of doing something.

You have to be ready for change. Given that the state of immigration is changing as rapidly as it is in 2019, you have to be ready to adapt to the changing policies and national and international mindsets. If you aren’t ready to adapt then you are not serving your clients to the best of your abilities. You are setting them up for failure.

What’s one trend that excites you?

I love seeing strong women in leadership roles and I think we’re at the beginning of a sea change across industries when it comes to women leading the charge. I think that law has historically been very much a male-dominated area, and to be able to lead a team of incredible women decision makers adds another layer of meaning to my work. D’Alessio Law Group has more women leaders in executive and management positions per-capita than any other law firm in the country, and helping women find their power and voice through their work, while supporting talent from all around the world is a personal calling that resonates both within and outside of the office.

The future is female! It’s time to embrace it.

What is one habit of yours that makes you more productive as an entrepreneur?

Besides loading up on coffee at the beginning of the day, I try to check in with my team on a regular basis. Checking in really fuels my ability to get things done throughout the day. I have always been a long-distance runner, and I approach my work as a marathon, not a sprint.

Speaking with my team of experts, many are immigrants themselves, and staying updated not only with their workflow but also on other aspects of their life, helps me understand how to approach our goals with a consistent timetable and awareness for all of the wheels that are in motion. My ability to deliver results to our clients hinges on how supported our staff feels and being able to confer with my team regularly is not only a luxury, but also a necessity when it comes to providing the best service possible for our clients.

I’ve surrounded myself with an incredible team and their energy and professionalism fuels me throughout the day.

What advice would you give your younger self?

I would give myself a pep talk on confidence. I would tell myself that I have a lot to give the world, and that overcoming insecurities will not only open doors down the road but will also make it easier to serve those who count on my expertise.

Half of the entrepreneurial game feels like a stare down contest. The sooner you can conquer any lingering anxieties, the better off you and your company will be.

Tell us something that’s true that almost nobody agrees with you on.

I don’t think that trust has to be earned.

I think I’m a very trusting person. Some people think I’m trusting to a fault. When I meet someone, there isn’t a period where I need them to earn my trust. I tend to give everyone the benefit of the doubt and give everyone a chance before they give me reason to think otherwise.

I choose to see the good in people because kindness builds loyalty, and loyalty fuels growth. If you lead with kindness, it’s easier to attract like-minded people who share your values.

As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?

Delegate, delegate, delegate. Being able to quickly identify tasks or responsibilities you don’t need to involve yourself in is vital when you are running a business. When there are so many ongoing projects and countless clients that need your attention, I can’t be everywhere at once. If I tried to tackle everything, I wouldn’t be able to do anything to the best of my abilities.

As a result I’m constantly assessing my strengths and weaknesses. The team of experts I have built around me fill the voids I myself am not able to handle on my own.

What is one strategy that has helped you grow your business?

Running D’Alessio Law Group like a company, rather than like a traditional law firm, has been our secret to growing our business. It allows us to focus on substantive customer service, while staying on top of the changing shape of immigration. Other firms within our field focus on creating systems that outsources the lawyer-client relationship, while our focus on building that trust between our team and client base has allowed us to make significant growth in the last few years.

Having a preexisting network helps reach more potential clients. Our background in entertainment, and as immigrants, helps us better understand the challenges that face our clients on a daily basis. Having gone through the visa process myself, I’m able to connect with our clients and their anxieties in a tangible way. Being part of the community that you serve creates more potential to better serve the people who look to you for guidance, expertise, and assistance throughout the challenges of the visa process.

What is one failure you had as an entrepreneur, and how did you overcome it?

When I first started DLG I definitely struggled with public speaking opportunities. We frequently attend industry events that allow us to speak to large audiences wanting to learn more about their visa options. In those early days I struggled to really voice my insight and expertise on these subjects. As a result, we found that we had trouble really capitalizing on these events meant to help us grow and reach new corners of the market.

Overcoming my confidence issues has been a steady process. Getting past my insecurities in front of a crowd did not happen overnight. It happened by booking more and more speaking engagements, meeting more people from all over the world, and honing in on my ability to connect with people from different backgrounds with a common goal. In this journey I discovered more about myself, and how to really understand the issues our clients face on a daily basis.

What is one business idea that you’re willing to give away to our readers?

I think a business that focuses on creating training programs and educational manuals for rising companies would be pretty valuable. Business leaders want a streamlined way to educate new employees. Equipping new hires with the tools and resources needed to do their jobs effectively is something that every organization wishes they could do better.
Every facet of every organization requires a clear training program, and having an established program would allow for greater potential growth within a company. People want these programs at every level of a company, whether that be for new hires or even leaders within a company. Reference manuals, coaching materials, and education tools can help business leaders grow along with their organization.

What is the best $100 you recently spent? What and why?

I recently took one of our paralegals out to lunch at a delicious little French restaurant in West Hollywood. She’s an incredibly talented paralegal who has been with the company from the beginning, through thick and thin, as is about to join us in the ranks of motherhood! It’s an exciting time that definitely calls for a celebration. We’re so thrilled for her and I am honored to call her my friend.

What is one piece of software or a web service that helps you be productive?

Serum Systems allows us to customize our communication with our clients. As we have grown, we have realized that, at our size, being a completely manual law firm is unworkable. We have too many clients to rely on manual systems to keep track of our progress. Serum Systems is a life saver in terms of addressing these issues and being able to use the system’s comprehensive data to better plan our timetables when servicing clients has been life changing. Serum Systems has allowed us to hit new milestones and make significant growth within our organization, and I recommend it to any firm that has a heavy work flow.

What is the one book that you recommend our community should read and why?

From Lawyer to Law Firm: How to Manage a Successful Law Business by Elizabeth Miller and Joryn Jenkins has been a huge help to me. One of the important topics in the book has to do with the best ways lawyers can approach billing their clients. Within the law community I know this is a recurring challenge, and for any other attorneys out there having this problem I cannot recommend this book enough.

I’m part of a national coaching group that features a number of other attorneys who lead law firms similar in size to D’Alessio Law Group. Client billing is frequently a topic of discussion, and it’s certainly an issue that isn’t reserved for the law community. When you’re accepting people’s payments, you have to approach it in an organized, thoughtful, and ethical way. This book goes into detail about how to best plan those transactions.

Another great read is 3 Vital Questions: Transforming Workplace Drama by David Emerald is helpful. There are a number great tips for avoiding workplace drama, and knowing when to involve yourself to ensure that your business is growing in a healthy manner.

What is your favorite quote?

I have a couple go-to inspirational quotes for when I’m feeling uninspired, but lately I’ve been appreciating a great bit from former U.S. President Ronald Reagan that has to do with what it means to be an immigrant in America. It was also part of his final speech as President, which only adds to the significance of it all.

“America represents something universal in the human spirit. I received a letter not long ago from a man who said, ‘You can go to Japan to live, but you cannot become Japanese. You can go to France to live and not become a Frenchman. You can go to live in Germany or Turkey, and you won’t become a German or a Turk.’ But then he added, ‘Anybody from any corner of the world can come to America to live and become an American.’

This really gets to the heart of the immigrant experience as well as what it means to be American. The U.S. truly is an aggregate of every type of person who lives and makes the hard trek of coming into the country. The quote goes on to mention that immigrants and their unique perspectives bring strength to the U.S., and that the country can only benefit from a diversity of perspective and opinion. As a Canadian myself, I’m more than inclined to agree with President Reagan.

Key Learnings:

• Building your trusted A-team requires you to understand both you and your company’s strengths and weaknesses and hiring to fill those gaps in expertise.
• Be humble with your ideas and be prepared to change. If you are rigid in your understanding of your business, you cannot expect to grow.
• The best way to serve your clients is by being part of their community. Understanding the needs and anxieties of your clients is crucial to serving them in the long-run.
• Be confident in the work you are doing, and in the value of your expertise. Your clients rely on your confidence, not only to get the job done, but also to address their concerns.
• Utilize systems that encourage better communication with your clients. More communication will guarantee a smoother process no matter the business.