Episode 404: What Makes a True Dealmaker with Sara Mostafa

From sketching fashion designs as a kid to leading complex M&A and private equity deals, Sara Mostafa shares what separates true dealmaking attorneys from ordinary transactional lawyers, why minority investment deals are like marriages with prenups, and what founders should understand before bringing in growth capital. In this episode of the DealQuest Podcast, host Corey Kupfer sits down with Sara Mostafa, the newest partner at Kupfer. Sara has spent more than two decades representing private companies and entrepreneurs across M&A, financing, private equity, governance, employment, real estate, and outside general counsel matters. Like Corey, she came out of big law and built a relationship-first practice that supports clients from inception through exit. WHAT YOU'LL LEARN: In this episode, Sara explains what separates a true dealmaking attorney from an ordinary transactional lawyer, why minority investment deals require “eyes wide open,” and how experienced attorneys balance legal risk against business upside without over-lawyering. She also discusses why AI-related transactions are dominating parts of the California M&A market, why dental and medical practices are commanding strong multiples, what the 2008 recession taught her about resilience and pivoting, and how long-term client relationships often evolve into serving the next generation of entrepreneurs. GUEST'S JOURNEY: Sara originally wanted to be a fashion designer, inspired by her aunt and her childhood love of sketching clothes. While studying at the University of Pennsylvania, she unexpectedly completed her degree requirements early and took a paralegal role at Drinker Biddle & Reath in Philadelphia, which inspired her to pursue law school. She began her legal career at Cooley in San Diego, working on biotech M&A deals before deciding big law was not the long-term fit she wanted. During the 2008 Great Recession, she pivoted to immigration law and nonprofit work in Hawaii before returning full-time to business transactions. She remains licensed in both California and Hawaii. THE DESIGNER DEALMAKER: Outside of law, Sara continues to pursue creative work. Last year she bought a sewing machine and now spends much of her free time designing and making clothes, including garments she is exhibiting at the San Diego County Fair. Like others at Kupfer, she believes building a successful legal career does not require abandoning personal passions or entrepreneurial pursuits. KEY INSIGHTS: A true dealmaking attorney focuses on helping both sides move forward rather than over-lawyering every issue. Business-mindedness, perspective, and the ability to negotiate practical middle ground matter as much as technical legal skill. Minority investment deals can dramatically change how founders operate. Investors often require approval rights over major decisions and expect a future exit, which means founders need to fully understand both the growth opportunity and the downside risk. Sara believes lawyers must balance risk against opportunity. Businesses cannot grow without taking risks, and experienced attorneys help clients evaluate likelihood and impact rather than simply redlining every possible issue. She also explains that curiosity and adaptability matter more than narrow industry specialization in most transactional work. Over her career, she has represented clients across industries ranging from restaurants and fitness centers to technology, healthcare, entertainment, and construction. Perfect for founders considering outside capital, business owners planning an exit, and entrepreneurs evaluating whether their attorney is truly helping get deals done or simply executing documents. FOR MORE ON THIS EPISODE: https://www.coreykupfer.com/blog/saramostafa FOR MORE ON SARA MOSTAFA:https://www.kupferlaw.com/ https://www.linkedin.com/in/sara-mostafa-02404211/ FOR MORE ON COREY KUPFER: https://www.linkedin.com/in/coreykupfer/ https://www.coreykupfer.com/ Corey Kupfer is an expert strategist, negotiator, and dealmaker. He has more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker. He is deeply passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast. Get deal-ready with the DealQuest Podcast with Corey Kupfer, where like-minded entrepreneurs and business leaders converge, share insights and challenges, and success stories. Equip yourself with the tools, resources, and support necessary to navigate the complex yet rewarding world of dealmaking. Dive into the world of deal-driven growth today! Episode Highlights with Timestamps:[00:00:03] Introduction: Sara Mostafa's two decades of transactional experience and her arrival as the newest partner at Kupfer [00:03:28] The sewing machine bought last September and exhibiting garments at the San Diego County Fair [00:08:12] Why transactional work appealed and the value of staying with clients through the full business life cycle [00:17:45] The 2008 Great Recession as the only real slowdown and pivoting to Hawaii [00:23:46] Minority investment deals as marriages with prenups [00:29:41] What separates a real dealmaker from a transactional attorney  [00:38:43] What client trust really means to Sara [00:43:11] The children of exited clients calling her for their own ventures [00:45:28] What freedom means: peace of mind Guest Bio:Sara Mostafa is a partner at Kupfer with over two decades of experience representing private companies and individuals across a wide range of transactional matters. Her practice encompasses contract negotiation, entity formation, corporate governance, mergers and acquisitions, private equity transactions, financing transactions, employment matters, real estate transactions, and outside general counsel services. She has represented companies in technology, wealth management, retail, entertainment, wholesale, construction, restaurants, medical practices, marketing, fitness, and nutrition, among others. Host Bio:Corey Kupfer is an expert strategist, negotiator, and dealmaker with more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker deeply passionate about deal-driven growth. He is the creator and host of the DealQuest Podcast.Related Episodes:Episode 293 - Sunny Vanderbeck: Building Relationships and Selling With Purpose Episode 350 - Tom Dillon: Understanding Business Valuation and Exit Planning Realities Episode 366 - Jodi Hume: Founder Exits and the Emotional Journey Behind Major DecisionsKeywords/Tags:M&A counsel, transactional attorney, dealmaking attorney, minority investment deals, private equity transactions, outside general counsel, California M&A market, AI valuations, dental practice multiples, medical practice multiples, Kupfer Law partner, big law transition, exit preparation, business life cycle counsel, relationship-driven dealmaking, risk versus upside, over-lawyering, corporate governance, entity formation, capital raising, next generation clients, peace of mind freedom