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