Prior to launching Weiss Law, Ashli Weiss worked with Fortune 500 companies, including Benefit Cosmetics, Western Digital, Tory Burch, and Louis Vuitton. Ashli, committed to supporting the tech industry, is advising as an attorney for several businesses that bring innovative products and services to the market. She spends her free time working with early-stage technology companies through 500 Startups and advises as the Chief Legal Officer for WomenTech Network. Ashli’s regularly featured in globally recognized publications. Ashli is a California barred attorney, and a member of both the American Bar Association and Bar Association of San Francisco.
What does “entrepreneurship” mean to you?
Ashli Weiss: Entrepreneurship is all about this relentless drive someone has to provide value in a way that contributes to something and fills a void in their chosen niche. You have to be flexible, motivated, and determined to make it work, and you have to be willing to wear a lot of different hats – but it’s that creativity that makes all the hours of building something new pay off.
Tell us about your first experience with entrepreneurship.
AW: While I was in grade school, I sold beef jerky sticks as part of sports team fundraisers – seriously! I was so good at selling those products because I put together pitches that weren’t questions and were more like advertisements. I remember my classmates would approach teachers or their parents or whoever and just ask if they’d like to purchase a beef jerky stick, but I’d time my sales pitches to lunchtime or other mealtimes so that hunger was there and people were more inclined to make a purchase. And then I made the sales!”
I think the internal element of that whole experience was my inability to accept “no” as an answer. It was this weird innate thing that I learned to display on demand because I was taught by my dad from a young age to stand up for myself despite my shyness. He encouraged me to push myself and ask for what I wanted, and that worked together with my beef jerky sales experience to mold me into the entrepreneur I would turn out to be.
What is your company’s origin story? What is the biggest reason you started your business? What did those early days look like and teach you?
AW: Prior to launching Weiss Law LLP, I worked with Fortune 500 companies. It was a great career and I’m incredibly proud of my work. Then, I took time off to raise a child – my now two-year-old daughter – and when I thought about going back to working in my former capacity, I decided I wanted work that would continuously challenge me but also give me the flexibility I wanted as a new mother.
At the end of 2020, I started my own law firm. That was rough on many levels; not only did I come up against the challenges many business owners encountered during the COVID-19 pandemic, but I also had to teach myself a lot of skills that I needed to build a business: marketing and networking tactics, brand-building skills, a lot of elements of business establishment that weren’t on the legal side of things.
The first six months were incredibly challenging because of those challenges, but at that eight-month mark, I started to see a return on my efforts. Clients started coming in, I was able to build a regular routine, and I’ve had a steady stream of great clients to support ever since.
What do you wish you knew when you started? Is there anything you would do differently?
AW: I wish I had more patience – and was also able to be kinder to myself in that regard. Especially when I first founded my firm, I put a lot of pressure on myself to perform. Putting that pressure on myself, in the end, kept me from enjoying the process of building a business, and I wasn’t appreciating the success I was experiencing. If I could go back and do things differently, I would be kinder to myself so I could enjoy the journey more.
What does “success” look like for you? We’d love to hear your biggest, boldest dream? What do you think will help you achieve it?
AW: Success is being comfortable financially, as well as satisfied with my personal life. Balance isn’t always possible, but satisfaction is. I’m definitely there now, but I definitely still am working on not putting that pressure on myself to perform well.
What is your superpower as an entrepreneur? What is your proudest and darkest moment so far? Share a key high and a key low from your journey if you can.
AW: Flexibility and versatility – I can go from staring at legal agreements for four hours to speaking at a virtual conference for people who found startups. Being able to switch from a legal expert to a business advocate and honing in on relationships with my partners is a superpower I love wielding.
My proudest moments are easier to think of than my darkest moments. I know I’m very lucky in that regard. My darkest moments came about in those early days when I was just trying to get clients. I think my proudest moment was the first time I realized I was consistently meeting my billable hour goals every month. It was amazing to see that I was doing something right.
What are your personal driving principals, your top values?
AW: The principle that drives me is my resolve to love the job. I truly love what I do. It never feels like a chore to go to work – I always look forward to it. I value that above almost everything when it comes to my day-to-day life.
For me, I don’t constrain myself to “normal” working hours. While my team is encouraged to put up those boundaries as they need to, I don’t check out of my email because I’m truly invested in my clients, and if there’s any way for me to support my clients, I want to do that because I genuinely love what I do. It doesn’t feel like work. It’s more like a passion project.
What’s it like to work alone or with your partners?
AW: The collaborative element of the work I do with my team is amazing. My support staff is super flexible, which is really fun because they’re as flexible and passionate as I am, and that start-up feeling is so nice. Going from being a solopreneur to bringing team members on board who are excited about what we’re building is an absolute rush!
Do you have a mentor? Tell us about what makes them valuable to you and your business?
AW: I have several mentors; there are a few people I like to keep in contact with on a semi-regular basis. But in addition, I’ve made a habit of making everyone in my orbit a mentor of sorts.
One of the things I learned as a kid – in addition to how to sell a lot of beef jerky sticks – is that it pays off to look up to and learn a little something from everyone around me. As a young person, I was always taking ideas from people around me and taking it into myself as a learning opportunity, and that’s something I definitely still do today.
What role does mentorship play in your world (as a mentor or mentee)?
AW: I’m a mentor and advisor for a few networks and digital NFT companies, and I love it! They ask me questions and I’m just there to provide support. The way I find I’m most able to support other companies and networks is by being open to every opportunity to support other people with the things I know and can do.
Many entrepreneurs continue to perfect their daily routines to support their work and greater vision; would you mind sharing your morning routine or a regular ritual that grounds your work each day?
AW: I have every minute accounted for in my daily routine – which sounds crazy but I have to! In order to be a mother, entrepreneur and wife, I need to have a schedule that allows me to be all three without dropping any of the many balls I juggle every day. Having every minute scheduled keeps me sane and happy, and that helps me know that everything will be accomplished that needs to be accomplished.
What are you reading or have read?
AW: I just read a law article on decentralized autonomous organizations – a type of entity for companies within digital assets on the blockchain. It’s a little bit nerdy, but I was just curious about the domain, so I started to read about it!
Where do you go for inspiration?
AW: A workout; sometimes during my work day, I get to a point where I just need to get my mind clear and focused, and that always happens during that hour-long workout.
Do you have a favorite quote, mantra, or words of wisdom to get through the tough days?
AW: My favorite thing to tell myself is to be comfortable with the word “no.” Especially when it comes to building my own client base and team: If I don’t try or don’t ask, how would I know if it’s possible or not? Better to ask the question than to just assume I know the answer.
What is a problem that keeps you up at night?
AW: I’m really lucky that there aren’t any on my mind right now. I think the only thing I’m thinking about all the time right now is making sure my team members are happy. I put a lot of time and energy into making sure they feel as fulfilled and happy in their daily work as I do, and I always keep that at the top of my mind as we go about our workdays.
How do you think about helping others through your work?
AW: I make myself available for communication. I think that’s absolutely critical. From one-on-one meetings with my team to being open to helping clients or the organizations I mentor any time they need me, I want to make myself available to people. My time is one of the best resources I have, and that’s also how I give back and offer support.
What advice do you have for fellow (and aspiring) entrepreneurs building and leading teams?
AW: Keep on top of technology and continue to build your network. Be the type of person you want to be surrounded by, because that’s the kind of people you’ll eventually be able to attract to your team. As an entrepreneur, the ethos with which you approach your work will trickle down to whoever is on your team.
What kind of an entrepreneur do you want to be known as – as in, what do you want your legacy to be?
AW: I want to be known as an attorney people come to because they’re looking for help and an authentic approach. It can be intimidating to approach an attorney for guidance, but I don’t want to be intimidating – I want to be a wealth of knowledge and resources!
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