What Makes a Real Dealmaking Attorney with Sara Mostafa

When Sara Mostafa joined our firm as Kupfer's newest partner, she hit the ground running. There was no warm up period, no easing in. She arrived with a strong client base that followed her over, and within days she was sprinting alongside Brian Meegan and me on active deals across multiple industries. That alone tells you something about her, but what I really wanted listeners to hear in this episode is how she thinks about deals, attorneys, and the long arc of client relationships.

Sara is a seasoned attorney with over two decades of experience representing private companies and individuals across a wide range of transactional matters. Her work spans contract negotiation, entity formation, corporate governance, mergers and acquisitions, private equity transactions, financing, employment matters, real estate, and outside general counsel services. She has represented companies in technology, wealth management, retail, entertainment, wholesale, construction, restaurants, medical practices, marketing, fitness, and nutrition. Like me, she came out of big law. Unlike many transactional attorneys, she has the mindset of an actual dealmaker. Whether you are an entrepreneur preparing for your first capital raise, a founder weighing whether to take on a minority investor, or a business owner thinking about an eventual exit, this conversation surfaces a lot of what I look for when I bring someone into the firm.

The Fashion Designer Who Became A Dealmaker

Sara did not grow up wanting to be a corporate lawyer. She wanted to be a fashion designer. Her aunt, one of her dad's sisters, was a fashion designer, and Sara spent hours with her sketch pad drawing designs as a kid. The legal career came almost by accident. She was at UPenn and learned from her dad that she had completed both her major and general requirements as a junior. He told her she was done and to find a job. She landed a paralegal position at Drinker Biddle and Reath, a large regional firm in Philadelphia, and that experience pushed her toward law school.

What I appreciate is that she has never abandoned that creative side. Last September she bought a sewing machine, and she now spends much of her free time designing and making clothes. She is exhibiting garments at the San Diego County Fair this year. Our firm is built on the premise that lawyers are also entrepreneurs with full lives outside the practice. Brian Meegan runs a separate company that provides administrative and paralegal bookkeeping services to about 70 law firms. I have built a speaking business and real estate investment funds alongside the law practice. Sara fits right in.

From Paralegal To Partner

Sara's first deal memory is from her time at Cooley in the San Diego office. She and another junior associate were sent to a biotech client's offices for an M&A transaction. They spent days digging through boxes of files for due diligence, well before virtual data rooms existed. I had a similar early experience in an air conditioned warehouse going through physical files for what felt like a week and a half. We both also remember sitting at financial printers waiting for prospectus pages on public offering deals, watching pages come off the press, marking them up, going back and forth through the night.

Those nights at the printer sealed something for Sara. She knew she did not want to stay at a large firm long-term. After Cooley she moved to Hawaii for a stretch, where she practiced immigration law during the Great Recession and worked at a nonprofit domestic violence agency. She remains licensed in both California and Hawaii. For the last 18 years she has done just business transactions.

Learning The Business Behind Every Industry

One of the most important traits a dealmaking attorney needs is intellectual curiosity about the business. Sara has it. So do I. So does Brian. Sara has represented restaurants, fitness centers, contractors, a Miss America contestant, entertainers, medical practices, wealth management firms, technology companies, and many others. Her view, which lines up with mine, is that most of the underlying transactional work is similar across industries. Operating agreements, contracts, employment matters, M&A documents. What changes is the business model, the regulatory overlay where it exists, and the texture of how the industry actually operates.

We do bring in specialists where it matters. Health care is a regulated area where I always bring in a health care expert. Same with certain export regulations or other niche regulatory areas. For the bulk of corporate work, though, knowing how to learn a business model quickly is more valuable than narrow industry specialization. As Sara put it, you always go in and you are learning something new when it is a different industry.

AI, Dental Practices, And The California Deal Market

I asked Sara what she is seeing in the market right now, and her answer matched what I am seeing across our firm. Deals have not slowed down, even in light of macroeconomic noise and global events. Things continue to pick up. In California, AI transactions are dominating the M&A landscape, particularly in Northern California and Silicon Valley. Businesses that have integrated AI into their model are commanding significantly higher valuations.

Outside of AI, she pointed to dental practices and medical practices in general as showing strong multiples. Some of those numbers are striking. In wealth management, which is a big part of our practice, we are seeing similar multiple expansion driven largely by private equity. I have clients who told me a year or two ago that they had a five to ten year runway left before considering an exit, and now they are calling because they have received offers or want introductions to bankers. When valuations are three times what they were seven years ago, taking some chips off the table becomes hard to ignore.

This connects to my conversation with Sunny Vanderbeck about the discipline of when and how to sell. Founders who plan for an exit while building the business tend to capture much better outcomes than those who scramble when the offer arrives.

The Reality Of Minority Investment Deals

Many founders look at minority investment deals as the perfect compromise. You take some chips off the table, you bring in growth capital, you keep control. Sara's framing of these deals is one of the most accurate I have heard. As she put it, you are entering a marriage with somebody, and it is as if you are entering the marriage with a prenup that comes with a lot of obligations. Owners who are used to operating independently and making decisions on their own suddenly find themselves needing consent for what an investor considers material decisions. The scope of materiality with an institutional investor tends to be wide.

Sara also pointed out the temporary nature of these arrangements. The investor is going to want out after a few years. You are going into the deal knowing there will be a divorce. That means accepting the risk that if your growth does not track the way the deal modeled it, you may need to buy the investor out at a predetermined amount, or face liquidation. Sara, Brian, and I are currently working on a deal where the client is sophisticated and growing rapidly. They have made a conscious decision to take meaningful downside risk in exchange for very large upside if they hit their growth targets. That can be the right call, but it requires the client to fully understand both sides of the equation.

Balancing Risk And Upside In Client Counsel

Lawyers are trained to identify risk. As Sara pointed out, you do not read cases in law school about deals that went well. You only read about the bad outcomes that ended up in court. That trains a generation of attorneys to over-index on risk. The problem is that businesses do not grow without taking risks. An attorney who only focuses on eliminating risk will either kill good deals or push clients into ignoring counsel.

Sara's view is that you cannot lose the forest for the trees. You have to lay out the risks, then assess the likelihood of each one materializing, and weigh that against the upside. More tenured attorneys tend to be better at this than junior associates who come out guns blazing trying to redline every clause to eliminate any whiff of risk. Part of the work is understanding the client's risk tolerance and helping them make an informed decision.

What Separates A Dealmaker From A Transactional Attorney

This is the part of the conversation I find most useful for business owners trying to choose counsel. Every transactional lawyer now claims to be a dealmaker because of the reputation some attorneys have built for killing deals. Not every transactional lawyer is actually a dealmaker. Sara's view is that you have to avoid over-lawyering. You need some business-mindedness alongside the legal work. You need to keep grasp of the bigger picture.

She also emphasized that there is almost always room to negotiate. Terms that one side or the other calls a non-starter can usually be reworked into something both parties can accept. The mindset of finding the place where both parties are willing to move forward is what separates a dealmaker from someone who simply executes documents. Jodi Hume's episode on the emotional side of founder exits touches on a related point. The psychology of all parties at the table matters as much as the legal mechanics.

The Outside General Counsel Role

Sara handles much more than M&A. She does commercial leases, real property purchase agreements, employment matters, customer contracts, separation agreements, entity formation, operating agreements, and buy-sell arrangements. She is the go-to attorney for clients in all things business transactions. For a client, that is the value of an outside general counsel relationship. They have one person they can call for most legal questions related to their business, and when something falls outside our wheelhouse, we route them to a trusted referral.

Our philosophy at the firm is that we want to be a resource even when we cannot directly handle a matter. If your kid gets in trouble and you do not know who to call, you can call me. We do not handle criminal work, but I probably know someone good who does. Between Brian's membership in IR Global, my involvement with the Entrepreneurs Organization attorneys group, and the decades of practice across all three partners, our referral network covers most situations.

The Bittersweet Side Of Long-Term Client Relationships

Sara articulated something I have felt many times over the years but rarely heard expressed so clearly. When you have walked alongside a client from inception through growth, contracts, employee matters, deals, leases, and finally an exit, the moment of monetization is exciting and bittersweet at the same time. You have heard about their kids from T-ball to college. You know what their success has meant for their family. And then the active engagement winds down.

Sara has noticed something else I love about long client relationships. The children of business owners she helped exit often call her years later for help with their own ventures. She is now supporting that next generation. In my book, getting referred to a client's kids who actually retain you is one of the ultimate compliments in this work. The other is being referred by someone who sat across from you at the negotiating table on a prior deal. Both have happened to us, and both speak to the kind of relationship-based practice we have always tried to build.

Peace Of Mind As The Highest Freedom

I close every episode by asking guests what freedom means to them, because freedom is my highest value. Sara's answer was simple. For her, ultimate freedom is peace of mind. The ability to find contentment and security regardless of circumstances. That answer ties back to everything we talked about. The ability to pivot during a recession. The resilience to keep designing clothes on the side while running a full transactional practice. The capacity to negotiate complex deals without losing sight of the human relationships underneath them. Peace of mind comes from knowing who you are and what you value, and Sara has clearly built her career on that foundation.

Conclusion

Tune in to this episode to hear Sara Mostafa share what she is seeing in the deal market, how she thinks about counseling clients through risk, and what separates a real dealmaker from an ordinary transactional attorney. From the realities of minority investment deals to the bittersweet arc of a long-term client relationship, this conversation offers business owners and aspiring dealmakers a clear window into how an experienced dealmaking lawyer actually operates. For more on the relationship-driven approach to deals, check out my conversation with Sunny Vanderbeck. For the emotional dimension of founder exits, Jodi Hume's episode is a strong complement.

Listen to the full episode of DealQuest Podcast with Sara Mostafa: Available on all major podcast platforms

FOR MORE ON SARA MOSTAFA 
 https://www.kupferlaw.com/ 

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!