How To Hire a Short-Term Lawyer (and Why You Should) feat. Dan Reilly

Dan Reilly, the co-founder of Legably, a platform that connects lawyers, paralegals, and law students with short-term freelance opportunities, joins the You Are a Lawyer Podcast this week. Dan shares the story behind Legably's creation, the challenges of introducing freelance platforms to the legal profession, and how the platform revolutionizes how attorneys and legal professionals work.

LISTEN TO LEARN

  • About the creation and purpose of Legably
  • Benefits of using Legably for solo practitioners and law firms
  • The availability of Legably and how to access it

WE ALSO DISCUSS

  • The challenges of introducing freelance platforms in the legal profession
  • Advice for new lawyers exploring different areas of law, finding their niche
  • The importance of understanding the business aspect of practicing law

Want to start a podcast?

Save time and create faster with KD Creative. KD Creative offers done-for-you podcasting services by launching podcasts for small business owners and editing podcasts for existing podcasters. 

If you’re ready to get your content in the ears of your ideal customers, start working with KD Creative. Visit skiptheboringstuff.com to hire a podcast coach.

How To Hire a Short-Term Lawyer (and Why You Should) feat. Dan Reilly

<iframe width="100%" height="180" frameborder="no" scrolling="no" seamless="" src="https://share.transistor.fm/e/17fd4d1d"></iframe>

How To Hire a Short-Term Lawyer (and Why You Should) feat. Dan ReillyHow To Hire a Short-Term Lawyer (and Why You Should) feat. Dan Reilly

About This Episode

Dan Reilly’s Background

Dan Reilly, the co-founder of Legably, has a diverse background from politics to executive search to practicing law. He started his career as a lawmaker, winning a seat in the House of Representatives at 21. This experience gave him a crash course in running an organization and provided valuable insights into the business world. His risk-taking mindset has propelled him to take on new ventures, including creating Legably.

"Once you do something like that, you say, well, if I could do that, then what's so tough about starting a business? What's so tough about starting a law practice?" reflects Dan Reilly on You Are A Lawyer.

In addition to his entrepreneurial pursuits, Dan runs a solo law practice focused on executive compensation and employment law. His experience in executive search allowed him to negotiate agreements for C-suite level executives, and he now advises executives and employees on their offer letters, employment contracts, and compensation plans. With his unique background and understanding of the business world, Dan provides valuable insights and guidance to his clients.

Why Law School

Dan came from a family of lawyers and had an early interest in law, making law school a natural choice. However, his path to law school took an unconventional turn when he ran for the state legislature and won a seat at 21. This experience sparked his interest in pursuing a legal career, and he decided law school was right for him.

"I always thought about perhaps going to law school and at that point I decided that was the right move for me,” explains Dan Reilly on Episode 118 of You Are a Lawyer.

After graduating from law school, he left the state house and began his career as a practicing attorney, specializing in executive compensation and employment law. This non-traditional path, combined with his experience in politics and business, has shaped his approach to the legal profession and has made him a versatile and innovative lawyer.

<iframe width="560" height="315" src="https://www.youtube.com/embed/vv2vY05lrvE?si=L25wWeG-N_g3BTbX" title="YouTube video player" frameborder="0" allow="accelerometer; autoplay; clipboard-write; encrypted-media; gyroscope; picture-in-picture; web-share" allowfullscreen></iframe>

What You Can Do With a Law Degree

A law degree opens possibilities and allows individuals to pursue various career paths. As Dan, the co-founder of Legably, mentioned in the podcast episode, "The true answer is you really can do anything." Whether practicing law in a firm, working in-house for a company, starting your own business, or even transitioning into a different field, the skills and knowledge gained from a law degree are precious. New lawyers must keep their options open, explore different areas of interest, and be open to new opportunities. The key is to find what aligns with your passions and strengths, and to adapt and evolve in your career journey continuously.

"The law degree is a great credential to have in the business world if you never practice," emphasizes Dan Reilly on Episode 118 of You Are A Lawyer.

This highlights the versatility of a law degree and its applicability beyond traditional legal practice. The critical thinking, analytical skills, and attention to detail developed through legal education can be valuable assets in various industries and professions. So, whether you choose to practice law or venture into other fields, a law degree provides a solid foundation and opens doors to many opportunities.

Lawyer Side Hustles

Legably is a platform that connects attorneys, paralegals, and law students with short-term freelance opportunities in the legal field. Founded by Dan Reilly, a practicing lawyer, Legably was born out of needing a more efficient and streamlined way to hire local counsel in different states. The platform allows attorneys and legal staffing firms to post projects, hire freelancers, share documents, and communicate in one place. With nearly 7000 users nationwide, Legably provides a valuable resource for lawyers looking to expand their practice, handle overflow work, or find specialized expertise. 

"Legably is a platform that connects attorneys, paralegals, and law students with short-term freelance opportunities in the legal field," explains Dan Reilly in Episode 118 of You Are A Lawyer.

Whether you're a solo practitioner, a large firm, or in-house counsel, Legably offers a flexible and cost-effective solution to handle overflow work, find specialized expertise, and enhance productivity. With its growing user base and commitment to innovation, Legably is shaping the future of legal work and empowering legal professionals to thrive in a rapidly changing industry.

Join the FREE mailing list!

Get behind-the-scenes content from You Are A Lawyer. 

1) Visit www.youarealawyer.com

2) Add your email address to the Subscribe pop-up box OR

3) Enter your email address on the right side of the screen

4) Get emails from me (I won't fill your inbox with junk)!

Contact Dan Reilly

Dan Reilly is licensed to practice law in both Rhode Island and Massachusetts.

Learn more about Dan:

Reilly Legal

Legably

Interact with You Are A Lawyer

Kyla Denanyoh hosts the You Are A Lawyer podcast. 

Follow the podcast:

YouTube: youtube.com/@youarealawyer

Instagram: instagram.com/youarealawyer

Twitter:  twitter.com/YouAreA_Lawyer

Website: youarealawyer.com

<iframe width="560" height="315" src="https://www.youtube.com/embed/Jr7Lm08nOQg" title="YouTube video player" frameborder="0" allow="accelerometer; autoplay; clipboard-write; encrypted-media; gyroscope; picture-in-picture; web-share" allowfullscreen></iframe>

Recent Episodes

Redefining Success and Alignment in Law

Arivee Vargas is a first-generation Latina lawyer who went from Big Law litigation to in-house corporate leadership, all before pivoting to become an author, executive coach, and speaker. She shares the raw story of her identity crisis after having her first child and how that led her to develop the framework for her book, Your Time to Rise, focusing on aligning your career with your deepest values. This conversation is essential for any high-achieving lawyer ready to stop checking boxes and start building a life of true purpose.
Read and listen here

Solo Firm Autonomy: Escaping the Partnership Trap

Yladrea Drummond went from being “team no care about the law" to becoming a highly successful trial attorney and solo firm owner in Maryland and DC. She openly shares the grit required to get barred after a seven-year journey, how she transitioned her practice from family law to dominating criminal defense, and the non-negotiable value of complete autonomy that running her own firm provides. This conversation is a raw, honest look at the transition from legal disappointment to becoming a respected "big dog in court" who is truly building a legacy
Read and listen here

How Hiring a Case Manager Will Transform Your Law Practice

Rob Levine is the founder of a multi-state law firm and an advocate for operational efficiency in legal practices. In this episode, he breaks down the vital role of case managers in improving law firm operations, building better client relationships, and increasing profitability. Whether you're a solo attorney or managing a growing team, this conversation will change how you think about delegation and workflow.
Read and listen here

Reinventing Your Legal Career Through Coaching

Elise Holtzman left Big Law to raise her children, without a clear roadmap for what came next. Now she’s a leadership coach and founder of The Lawyer’s Edge, helping lawyers build confidence, develop business skills, and grow professionally. In this episode, Elise shares the mindset shifts that led her from practicing law to coaching those still in the field.
Read and listen here

Building a Legal Tech Startup from Law School

Lamia Rahman is a Forbes 30 Under 30 honoree, TEDx speaker, and co-founder of SEEKR, a tech startup creating wearable AI devices for the blind. In this inspiring episode, Lamia shares her journey from law school in Hong Kong to the front lines of legal tech, accessibility, and advocacy.
Read and listen here

How To Grow a Thriving Multi-Practice Law Firm feat. Daniel Rosenberg

Daniel Rosenberg is a seasoned trial lawyer and the co-founder of a thriving civil litigation firm. With roots in criminal defense and a career built in courtrooms, Daniel shares how he went from retail entrepreneur to legal leader and why flexibility, grit, and courtroom instinct are the skills that drive his success. This episode is all about staying ready, even when your office is your car.
Read and listen here

How to Find New Purpose After a Legal Career feat. A.X. Foster

A.X. Foster is a former prosecutor and defense attorney turned novelist who’s turning real-life courtroom experience into gripping legal thrillers. In this episode, he shares how his background in acting and law helped him build a successful writing career, why COVID was the creative catalyst he needed, and how his novels teach readers about the legal system, without getting lost in legalese.
Read and listen here

How to Take the Leap from Big Law to Solo Practice feat. Gary Martoccio

Gary Martoccio is an employment lawyer and solo practitioner who left a large firm after 12 years to build his own plaintiffs-side practice. In this episode, Gary shares what it’s like to advocate for employees, run your own firm, and earn multiple state licenses through bar exams and reciprocity. If you’re curious about employment law or considering going solo, this episode gives a real-world perspective you won’t find in law school.
Read and listen here

How to Balance Law, Life, and Leadership feat. Rhonda Coleman Wandel

Rhonda Coleman Wandel is a commercial attorney, podcast host, and founder of RCW Strategies LLC, a legal consulting firm serving visionary companies and legal teams. In this episode, she shares her bold transition from education to law, her path through in-house legal roles, and why she recently stepped into entrepreneurship after years at companies like Accenture and Google. From Memphis to Chicago, single motherhood to legal leadership, Rhonda’s story is about clarity, courage, and walking your own path.
Read and listen here

How To Blend Legal Teaching With Theater and Parenting feat. Keith Shannon and Kara Shannon

Keith Shannon is a former lawyer, legal educator, and lifelong theater fan. Kara Shannon is his daughter and creative collaborator. In this episode, Kyla speaks with the father-daughter duo about their journey from legal careers and musical soundtracks to launching Fourth Row Center, a podcast celebrating Broadway and family bonds. Their story is a heartfelt reminder that success can look like connection, creativity, and choosing joy on your own terms.
Read and listen here

How to Combine Law and AI Without Losing Your Mind feat. Austin Brittenham

Austin Brittenham is a first-generation lawyer, legal tech founder, and the creator of 2nd Chair, an AI-powered tool designed to help solo and small firm lawyers work faster and smarter. In this episode, Austin and Kyla talk about space law, law school culture, and what it really means to use your legal education creatively. From debating in high school to launching two startups, Austin proves that you don’t have to follow the traditional legal path to make a meaningful impact.
Read and listen here

How to Turn a Dream Job Into a Lifelong Mission feat. Dr. Rhonda Glover Reese

Dr. Rhonda Glover Reese is a certified career and leadership coach with 34 years of FBI experience under her belt. From counterintelligence to white collar crime, her federal career was vast and dynamic. In this powerful episode, Dr. Rhonda shares how her dream of working for the FBI led to a fulfilling career in public service and how her new chapter as a coach helps others step into their purpose with confidence.
Read and listen here

©2025 You Are A Lawyer LLC.
All rights reserved.