Barbara Napolitano, LawFuel contributor
Many lawyers have successfully left traditional practice to build standout businesses, often crediting their legal training with giving them an edge in negotiation, risk assessment and complex problem‑solving, even while warning that perfectionism and over‑caution can slow entrepreneurial progress.
This makes their stories powerful case studies for any lawyer considering a legal career pivot into business or alternative law jobs.
We took a look at former women working in law who turned their talents to entrepreneurial activities and have succeeded – but what did their legal background do to hurt, or help their business success?
9 lawyer‑turned‑business founders
Maggie (Louise) Callahan – Chocolatier (USA)
Former BigLaw mergers & acquisitions lawyer who left law to found Maggie Louise Confections, a highly branded, “Instagram‑ready” chocolate company that grew into a multi‑million‑dollar venture. Despite not having a ‘storied backstory’ about her business like many in the chocolate business, as Forbes reported, she has said that deal work and client service in M&A translated directly into building a premium consumer brand, but that she had to unlearn the billable‑hour mindset to focus on creativity and customer experience.
Callahan has said that years of M&A work taught her to move comfortably around contracts, investors and complex negotiations, which made scaling a premium food brand less intimidating. At the same time, she has acknowledged that BigLaw perfectionism initially made it harder to take creative risks in product and packaging.
Goli Kalkhoran – Course creator and podcaster (USA)
Ex‑litigator who left practice to start a photo‑booth business and later built “Lessons from a Quitter,” a podcast and education business helping professionals leave careers they dislike. She notes that legal skills in issue‑spotting and structured thinking make starting a business easier, but that lawyers’ fear of failure and sunk‑cost thinking can trap them in unhappy law jobs.
Kalkhoran credits litigation with sharpening her ability to analyse problems quickly and advocate clearly, which she now uses in coaching clients through career transitions. Yet she also talks about the identity shock of leaving a prestigious profession and how lawyers’ conditioning around “never quitting” can delay necessary changes.
Haley Altman – Legal tech founder (USA)
Former corporate lawyer who made partner before leaving to found Doxly, a deal‑management platform later sold to Litera. She highlights that understanding transactions and regulatory risk made it easier to design credible legal technology, but emphasizes that entrepreneurship required rapid decision‑making with incomplete information—very different from traditional legal practice.
Altman’s idea for Doxly came directly from late‑night deal closings, where she sat surrounded by manila folders hunting missing signatures and knew there had to be a better way. She has also spoken about the fear of leaving a secure equity‑partner role and the need to stop over‑dwelling on risks in order to grow a startup.
Jasbina Ahluwalia – Matchmaking business founder (USA)
Former practising lawyer who founded Intersections Match, a boutique relationship‑coaching and matchmaking firm. She points to client‑counselling, interviewing and confidentiality as core legal skills that translated directly into building a trusted, high‑touch personal‑services brand.
Ahluwalia has said that her legal training helps her ask probing questions, synthesise complex personal information and maintain strict confidentiality for high‑achieving clients. She also notes that leaving a conventional legal career required her to stop “getting ready to get ready” and accept the ambiguity of building a social‑impact business.
Chrissie Lightfoot – Legal AI entrepreneur (UK)
Once a practising solicitor, she became CEO and founder of Robot Lawyer LISA and a widely cited legal futurist and law‑tech entrepreneur who has won awards for her entrpreneurial endeavors. Lightfoot argues that lawyers who understand clients’ pain points are uniquely positioned to design AI‑driven products, but that traditional firm hierarchies can inhibit the experimentation needed to innovate.
She says that practising as a solicitor gave her deep insight into how clients actually experience legal advice and where traditional delivery fails them. She has criticised rigid law‑firm structures and risk culture for stifling innovation, suggesting that stepping outside practice was necessary to fully pursue AI‑driven solutions
Sarah‑Jane Butler – Working‑parents services founder (UK)
Former Magic Circle capital markets lawyer who left the partnership track to found Parental Choice, a business that supports working parents with childcare and work‑life solutions. She credits transactional experience and regulatory knowledge with helping her design compliant, scalable services, but says that running her own business finally gave her control over her time and the client journey.
She points to Magic Circle training as invaluable for handling regulation, contracts and the institutional clients that rely on Parental Choice for childcare and compliance support. She has, however, described partnership‑track hours and inflexibility as incompatible with parenthood, which is one reason she wanted a business where she could design healthier working patterns.
Reina Menezes D’costa – Legal and business consultancy owner (UK)
UK‑qualified lawyer who founded Bizlaw U.K., a holistic legal and business services consultancy for micro‑businesses and international investors. She notes that the credibility of a legal background helped win early clients, while entrepreneurship demanded resilience and a mindset shift from individual case wins to long‑term business building.
D’costa notes that coming from a respected legal background meant small‑business owners and international investors trusted her judgment from day one. At the same time, she has spoken about needing to move beyond a narrow “case‑by‑case” mentality and instead think like a founder about marketing, systems and recurring revenue.
Laura Keily – Legal tech and dispute‑resolution founder (Australia)
A barrister who founded Immediation, an online dispute‑resolution and justice‑tech platform, after becoming frustrated with inefficiencies in the court system. She has argued that deep courtroom experience gave her insight into where the system fails users, while launching a startup forced her to move away from adversarial thinking toward product‑led collaboration.
Laura Keily’s years as a barrister gave her a granular understanding of litigation bottlenecks, allowing her to design Immediation around speed, access and procedural fairness. She has also suggested that adversarial training can be a handicap in startup life, where collaboration with technologists, investors and even competitors is essential to progress.
Andrea Jewell’s move from barrister to peanut butter
Andrea Jewell is the co‑founder of Fix & Fogg, the New Zealand-based nut‑butter brand that has gone from small‑batch experiments to shelves in thousands of stores, including across the United States. Originally from the UK, she trained and practised as a criminal barrister before moving to New Zealand, later working in‑house roles for ACC and the NZ Qualifications Authority.
Together with her husband Roman, also a former lawyer, she left the corporate track to build a business focused on meaningful, sustainable, high‑quality peanut butter. Jewell’s legal background helped with contracts, regulation and methodical problem‑solving, but she has also spoken about the challenge of leaving a predictable legal career path for the uncertainty and constant hustle of entrepreneurship.
So what lessons can these nine, former lawyers teach those women seeking to enter business life on their own?
How a legal background propels entrepreneurship
Structured problem‑solving and risk management
Former practitioners consistently point to their ability to deconstruct complex challenges—whether designing a product, closing a deal or pitching investors—as a decisive edge over peers without legal training. That same analytical rigour helps entrepreneur‑lawyers evaluate market risk and sidestep the contractual landmines that sink early‑stage ventures.
Client insight and persuasive communication
Advising demanding clients teaches lawyers to surface unstated concerns, ask incisive questions and distil complexity into actionable advice—capabilities that translate directly into effective sales, brand storytelling and customer retention. Founders working in B2B or legal‑adjacent markets report that this background accelerates trust‑building with enterprise buyers and institutional backers.
Commercial nous in contracts and regulation
Entrepreneur‑lawyers cite contract literacy—knowing what to draft in‑house and when to brief specialists—as a source of both speed and savings during a venture’s formative months. A working grasp of regulatory frameworks also confers a material advantage in tightly governed sectors such as fintech, food, childcare and justice technology.
How legal training can impede the entrepreneurial shift
Perfectionism and an aversion to uncertainty
Many of these founders observe that the profession rewards error avoidance, a habit at odds with the lean‑startup ethos of rapid testing and iteration. Over‑researching, waiting for complete information and polishing before launch can delay market entry and make ex‑lawyers reluctant to ship minimum viable products or abandon unworkable hypotheses.
Professional identity and sunk‑cost psychology
Several interviewees describe the acute difficulty of stepping away from an elite credential and years of accumulated expertise, even when their legal role no longer aligns with their ambitions or well‑being. That inertia can trap talented practitioners in ill‑suited positions long past the point of rational departure.
The billable‑hour paradigm
Founders who left large firms say that equating value with time recorded hindered their ability to think in terms of scalable products, brand equity and recurring revenue streams. Moving from hours sold to outcomes delivered, systems built and intellectual property created represents a foundational mindset shift for lawyers entering business.
Practical guidance for lawyers contemplating a pivot
Deploy your skills, but adopt new scorecards
Bring drafting precision, negotiation acumen and issue‑spotting discipline to your venture, but measure progress in experiments launched, customers served and value generated—not time sheets. Revenue, retention and tangible impact are the benchmarks that matter in an entrepreneurial career.
Launch early and iterate in public
Goli Kalkhoran, Haley Altman and fellow founders urge colleagues to ship before every variable is controlled, then refine based on live user feedback. Treat your first offering as a working prototype, not a finished opinion, to escape analysis paralysis.
Build around pain points you witnessed first‑hand
Many of the most successful lawyer‑founders identified their ventures by observing inefficiencies in practice – cumbersome transactions, time‑starved parents, underserved small‑business clients or access‑to‑justice failures. Starting with a problem you know intimately yields a clear niche, strong product‑market fit and credible messaging to other professionals weighing a career change.
Prepare for a steep commercial learning curve
Former lawyers often underestimate how much of their time will go to selling, recruiting and managing rather than substantive work. Those who treat business development as a discipline in its own right—rather than a distraction from “serious” tasks—tend to scale faster and with greater confidence.
Have an inspiring change-of-career pivot to report? Let us know at LawFuel. Email: lawfuel@gmail.com
