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Danielle Fontanesi: “Whether you think you can or think you can’t, you’re probably right”

“Whether you think you can or think you can’t, you’re probably right.” This was a variation on a Henry Ford quote that my mom instilled in me. I live by it, and it’s turned out to be true more often than not. As a part of our series about women who are shaking things up in […]

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“Whether you think you can or think you can’t, you’re probably right.” This was a variation on a Henry Ford quote that my mom instilled in me. I live by it, and it’s turned out to be true more often than not.


As a part of our series about women who are shaking things up in their industry, I had the pleasure of interviewing Dani Fontanesi.

As a seasoned Silicon Valley attorney, Dani Fontanesi is redefining the legal industry across the tech world. Her innovative approach to navigating legal risk allows her clients to move fast and break things while protecting their interests and minimizing exposure. Dani’s portfolio of clients includes early stage and rapid growth companies backed by some of the top investors in the world — Sequoia Capital, Andreessen Horowitz, Y Combinator, Redpoint, Sound Ventures (Ashton Kutcher’s fund), Bain Capital Ventures, and Founders Fund (Peter Thiel’s fund) — the same VCs that launched Facebook, Twitter, Netflix, Instacart, Google, Apple, OfferUp, Robinhood, LinkedIn, Stripe, Oracle, Okta, WhatsApp, DoorDash, Instacart, Airbnb, Lyft, Pinterest, and Carta. Dani’s practice focuses on simplifying the legal process for her clients, creating innovative products and solutions to allow her clients to grow, scale, and thrive — strategically.


Thank you so much for doing this with us! Before we dig in, our readers would like to get to know you a bit more. Can you tell us a bit about your “backstory”? What led you to this particular career path?

Prior to founding Fontanesi Law, I was the lead in-house counsel for a tech company in Silicon Valley. When I needed external counsel, I found it very difficult to find top-quality law firms that were responsive, approachable and didn’t charge $600–1,000+ per hour. If I wanted quality legal advice, I had to sacrifice adaptability and good service. If I wanted flexible, reliable service, I had to sacrifice quality. There was a gap in the market that needed to be filled. So I left my role at an Andreessen Horowitz backed tech company and founded Fontanesi Law.

My journey to this career path was unconventional. My mom was a legal secretary when I was growing up, and I always aspired to be like her. She was the smartest and hardest working person I knew, despite various challenges she faced in life. She was a young mother — only 18 years old when I was born — and she fought to give me the best life she could. She homeschooled me for many years to give me a better education than the public schools in our area. She instilled in me that I could learn anything, do anything, and be anything I set my mind to. She taught me that life’s circumstances don’t define you — they just create opportunities to pave a path that no one’s paved before.

I went on to become the first person in my family to graduate college, and after working a few years, I mustered up the courage to apply to law school. This meant I first had to take the LSAT — a daunting test that determines the fate of would-be law students across the country, weeding out many of them. I decided to take a prep course that provided simulated exams. When I took my first practice exam, I failed terribly. I didn’t even complete half the questions in the time allotted. I mentioned to my instructor that I wanted to increase my score to the 90th percentile, and I asked what I needed to do to get there. She looked at my practice test score and shook her head. That wouldn’t be possible, she said.

I realized at that point that I would have to teach myself. I learned in my many years of homeschooling how to teach myself new things quickly. I bought a book of practice tests and took dozens of former LSATs until I learned the sequence and timing. In the end, I scored in the 98th percentile. This gave me my pick of law schools, complete with generous scholarship offers, and eventually led to my first job as a corporate attorney. I had a private office with an ocean view where I worked on mergers and acquisitions, capital raises, and financings.

It seemed like I had finally made it, but as I looked around my office, I noticed something strange. The firm was made up of many brilliant women, but very few of them were at the top. The partners were almost exclusively male. I knew if I stayed in that role, I’d eventually hit my glass ceiling. So I left. I took an in-house position at a multibillion-dollar, publicly-traded company where I had an amazing boss and endless growth potential (and still had my ocean view!).

But a year later, my world came crashing down. My husband and I were three days into our honeymoon when he was diagnosed with an aggressive form of leukemia. We suddenly found ourselves trapped 7,000 miles from home, living in a hospital, fighting for his life. We spent the next year in and out of hospitals, living in isolation to insulate him from germs that would be fatal to his delicate immune system. We lost our house, our car, our jobs, our savings, and nearly everything we owned during that year. But his bone marrow transplant was successful, and that’s all that mattered.

When I was finally able to return to work, I spent many months looking for a job that would allow me the flexibility to accommodate my husband’s medical needs while working. I finally realized the job didn’t exist — not in my field. As a successful corporate attorney, you were expected to devote almost the entirety of your existence to your job. Family and personal life were a far second.

It took a personal tragedy that threatened to take everything from me before I realized: the legal industry was broken. If I wanted to continue my career, I would have to rewrite the rules, undo the stereotypes that have plagued this industry for years, and reinvent the world of corporate lawyering.

Nearly ten years later, I now own a thriving law practice that’s changing the legal landscape in Silicon Valley. Tech companies from San Francisco to New York are finding a new way to approach legal. The staunch, white-shoe law firms that dominated the market to date are no longer fit for their purpose. Startups and entrepreneurs want a legal team that’s quick, nimble, innovative, and adaptable. They want easy and affordable access to the tools and legal expertise needed to help their businesses grow, scale, and thrive. That’s where Fontanesi Law stepped in to rewrite the script.

Can you tell our readers what it is about the work you’re doing that’s disruptive?

The legal industry has historically been dominated by large, inflexible law firms charging rates that most businesses can’t afford, for advice that’s often confusing, impractical, or generally unhelpful. At Fontanesi Law, we seek to simplify the legal process for our clients, empowering them to take control and make decisions that are right for their business.

We are redefining how startups, founders, entrepreneurs, and businesses gain access to the tools and legal expertise needed to help their businesses grow, scale, and thrive strategically. We do this by shifting the focus to products and solutions rather than billable hours. We offer various solutions-based packages designed to cover everything from employee & HR needs to capital raises. Unlike traditional law firms, we have no billable hour requirements for our attorneys, which removes the pressure to work around-the-clock racking up fees. By redefining success for our attorneys, we provide better, more cost-effective solutions to our clients.

We view each of our clients as a partner, and we help them grow in a way that’s best for their unique circumstances. We understand that sometimes businesses need to move fast and break things, and that’s okay. We help them find innovative ways to achieve their goals while minimizing their legal risk.

Another thing that sets up apart is that our workforce is distributed — meaning our attorneys and support staff work from home or wherever is most convenient for them. This flexibility allowed us to ramp up quickly and seamlessly when the COVID pandemic hit — we were already equipped to operate in the “new normal”, and we helped our clients navigate the new legal hurdles with ease. Unlike the traditional law firms that move slowly, charge heavily, and are slow to adapt, we are at the front — leading and innovating alongside our clients.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

One of my first bosses had a thick accent from New Zealand and tended to mumble his words. I had the hardest time understanding him, but I was hesitant to ask him to repeat himself. One time he asked me to draft a contract for a client, but I misunderstood him and drafted the entirely wrong contract. During my performance review a few months later, he commented that I was “getting better at understanding [him]”. I was mortified, but it taught me that it’s okay to ask questions when you don’t understand something. It’s much better to clarify things on the front end rather than wasting time and energy fixing something on the back end.

We all need a little help along the journey. Who have been some of your mentors? Can you share a story about how they made an impact?

My former boss, Jason Stein, was the best mentor I’ve had in my professional career. He was General Counsel of a multinational company and was incredibly brilliant, but was always humble and self-deprecating. He was people-focused in his leadership style, and he inspired each person in his team to achieve their best because he led by example. He challenged me to push my boundaries and to take on projects I didn’t think I was capable of. He never micromanaged, and it never felt like he was looking over my shoulder, but I always knew he was in the background, like a safety net, to catch me if I stumbled. I try to model my own leadership style after him, but it’s a work in progress!

In today’s parlance, being disruptive is usually a positive adjective. But is disrupting always good? When do we say the converse, that a system or structure has ‘withstood the test of time’? Can you articulate to our readers when disrupting an industry is positive, and when disrupting an industry is ‘not so positive’? Can you share some examples of what you mean?

Disruption is needed when a system is broken. When something is no longer fit for its purpose — or is failing at its essential purpose — it needs to be fixed. Often, to fix something, you have to take it apart and then rebuild it entirely.

As a real-life example, my 20-month-old son recently broke one of the wooden shutters on our windows and it no longer closes properly. My husband looked at various ways of fixing it — gluing it back together or replacing one of the pieces — but ultimately trying to piece it back together wouldn’t fix it. We’d have to replace the entire thing — meaning, we’d have to take it apart and rebuild it. The same thing is true for systems, processes, institutions, and ways of thinking. If it no longer works the way it should — given changing circumstances, priorities, and objectives — it should be taken apart and rebuilt.

Unfortunately, as a society, we often try to fix things in a way that requires the least amount of effort. We try to glue it together rather than rebuilding it. Rebuilding something means tearing it apart first, and tearing something down is naturally disruptive. It inconveniences people. It challenges them to do things differently. It forces them to question the status quo. It forces change, and change makes people uncomfortable. But change is the only constant that keeps us driving forward.

Disruption is necessary for progress, but that’s not to say that disruption is always a good thing. In the legal industry, we frequently say that litigation is very disruptive to a business. It’s distracting to the owners, managers, and employees involved. It’s emotionally taxing. It’s time-consuming without pushing the business forward. It’s a negative disruption. However, even litigation is necessary sometimes. Although the process can be taxing, the outcome is often necessary.

Can you share 3 of the best words of advice you’ve gotten along your journey? Please give a story or example for each.

“Don’t have a plan. Have a general direction and take advantage of opportunity as it arises.” This was a quote from Andy Puzder, the former CEO of CKE Restaurants (e.g., Carl’s Jr. and Hardee’s). He’s an attorney, and he guest lectured one of my corporate law classes in law school. At the time, everyone around me seemed to have a plan. They seemed to have been born into the plan: Get straight A’s, go to a good college, intern at a reputable organization, volunteer overseas for something, go to a good law school, get on law review, get a high-paying job, get married, have two kids… The absence of a plan in my life made me feel like a failure — as if not having a plan meant I was lost. The reality was that my life circumstances didn’t afford me the luxury of having a plan. But I always had a general direction, and that flexibility allowed me to pivot when needed. It allowed me to create opportunity from whatever resources I had at my disposal, and ultimately, it led me to where I am today.

“If you bend, you will not break.” This was a quote I learned from a yoga instructor, but it applies to so many aspects of life. Being pliable and adaptable will allow you to pull through any storm, no matter how big it is.

“Whether you think you can or think you can’t, you’re probably right.” This was a variation on a Henry Ford quote that my mom instilled in me. I live by it, and it’s turned out to be true more often than not.

We are sure you aren’t done. How are you going to shake things up next?

My goal is to continue innovating in the business and legal space — making quality legal products, solutions, and resources available to every founder, startup, entrepreneur, and business out there. Legal expertise shouldn’t be a luxury reserved for wealthy entrepreneurs and heavily funded startups. We help our clients position their companies to attract top tier investors and raise the capital they need to grow, scale, and thrive.

Our clients are backed by some of the biggest names in the industry: Sequoia Capital, Andreessen Horowitz, Y Combinator, Redpoint, and Founders Fund, to name a few. These VCs are the same investors that launched Facebook, Twitter, Airbnb, Instacart, Netflix, and just about every other Silicon Valley company you’ve heard of. My goal is to continue increasing access to critical legal services to enable people from all walks of life to found and grow a successful business.

In your opinion, what are the biggest challenges faced by ‘women disruptors’ that aren’t typically faced by their male counterparts?

I think the stereotypes that have plagued women over the years continue to tarnish the accomplishments of even the most powerful and influential of women. We see it even as high up the ranks as our incoming Vice President and First Lady who have both been slandered by those claiming they reached their positions based on their association with a man — or anything other than merit. The same stereotypes apply to women disruptors. People have preconceived notions of the roles women should play, and disrupting an industry is generally not one of them.

Disrupting the legal space in Silicon Valley has been especially challenging as a woman. Both the legal and tech industry have been heavily dominated by men for years, and it’s difficult to establish a position of authority when people pigeon-hole you before you speak. I was at a mediation a couple of years ago with the CFO of my company (a male), and the mediator directed all questions to him and the external lawyer (also a male) who was attending the mediation with us. It was only after I interjected on a legal issue that the mediator turned and asked if I was an attorney and confessed to assuming I was the CFO’s assistant.

The challenges faced by women won’t go away overnight, but it’s critical to keep plowing ahead, pushing boundaries, and redefining the landscape. Fortunately, I’ve had the opportunity to work with some inspirational and influential men and women in Silicon Valley who have helped me tear down barriers and overcome hurdles typically faced by women in my position.

Do you have a book/podcast/talk that’s had a deep impact on your thinking? Can you share a story with us?

Grit to Great: How Perseverance, Passion, and Pluck Take You from Ordinary to Extraordinary by Linda Kaplan Thaler and Robin Koval. This book resonated with me because it illustrates so well what my mother instilled in me: that you don’t have to be born into privilege to make a profound impact on the world, in your community, in your industry, or in your profession. The authors are two women who grew up in the Bronx, with no special advantages or privileges, and they carved a path in life that was all their own — and led to exceptional professional successes.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

If all of us donated just 1% of our income to those in need, it would have a profound impact on the planet. A friend of mine in New Zealand started an organization called One Percent Collective that’s based on this exact theory (https://www.onepercentcollective.org/).

My husband and I took a slightly different approach to giving this year during the holidays. We were looking for a way to help a family in need. We looked into Salvation Army’s “Adopt a Family” program, but couldn’t find one in our area. We found an organization called family-service.org, but they received so much support this year, they had no more families to adopt. I called and emailed churches, but received no response. We were hitting wall after wall.

So I sat and thought about what I would do if I couldn’t afford a Christmas for my family this year. I figured I would probably look on OfferUp for free toys. So we created a posting for free toys, and within hours, we had over a dozen messages — many of them just asking for winter clothes or shoes for their kids. One mom had planned on wrapping whatever snacks she could find in the cupboard as gifts for her kids this year.

We couldn’t turn any family away, so we drove around delivering gifts to about a dozen different families. We met moms at public places near their homes for safety (Target or Walmart shopping centers) and handed them bags full of clothes and toys. They cried. They laughed. They wrote notes of gratitude. There’s no better feeling than giving, and so many people in the world are hurting. If we all gave a little, we could make a huge change in the world.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

“She believed she could, so she did.” I saw this quote one day, and it resonated with me. I’ve always believed in myself in circumstances that seemed impossible. Time and time again I’ve had to prove to myself and the world that I can do it — whatever it may be. I now have this quote above my desk and read it every day.

How can our readers follow you online?

You can follow me on LinkedIn for inspirational stories, tips, and legal resources for business. https://www.linkedin.com/in/dani-fontanesi-esq-26509a8/

This was very inspiring. Thank you so much for joining us!

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