Alex Shahrestani of Promise Legal: “Ignore Naysayers”

Ignore Naysayers — Any time you prepare to take a leap, there are going to be a lot of people who tell you that you can’t, or shouldn’t, or won’t. Sometimes they’ll be right, but in the legal profession saying “no” is the rule. Be incredulous. Ask why not. Oftentimes the doubts are based on indigestion more […]

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Ignore Naysayers — Any time you prepare to take a leap, there are going to be a lot of people who tell you that you can’t, or shouldn’t, or won’t. Sometimes they’ll be right, but in the legal profession saying “no” is the rule. Be incredulous. Ask why not. Oftentimes the doubts are based on indigestion more than some actual problem. Criticism has its place, but scrutinize it before you accept it.

The legal field is known to be extremely competitive. Lawyers are often smart, ambitious, and highly educated. That being said, what does it take to stand out and become a “Top Lawyer” in your specific field of law? In this interview series called “5 Things You Need To Become A Top Lawyer In Your Specific Field of Law”, we are talking to top lawyers who share what it takes to excel and stand out in your industry.

As a part of this interview series, I had the pleasure of interviewing Alex Shahrestani.

Alex Shahrestani is the managing partner of Promise Legal, a Texas-based law firm focusing on technology and serving startups who want to change the world. Alex serves as Council Member for the technology section of the Texas Bar, Vice President of EFF Austin, CLE Coordinator for SXSW, and is the founder of the Journal of Law and Technology at Texas. He spends his spare time changing diapers, tinkering with new coding solutions, and being a dork with his wife and law partner, Maggie.

Thank you so much for joining us in this interview series. Before we dig in, our readers would love to get to know you a bit more. What is the “backstory” that brought you to this particular career path in Law? Did you want to be an attorney “when you grew up”?

I had always heard that I should be an attorney, and I sort of took it for granted. I was going to college during the financial crisis and suddenly found myself without the means to fund my education. I took stock of my life, and realized that being a lawyer ticked a lot of boxes for me: I’d be able to help people, I could do a lot of reading and writing, I could be a problem solver, and I could make a good living. I had a chance to refocus, and I began looking for my niche. I knew exactly what I was going to do when I read an article in Wired, or some similar publication, about a hacker who was on trial. The prosecutor said of the defendant during closing arguments, “I don’t know what he did or how he did it, but I know it was wrong.” I figured I could do better than that, so I got educated in computer programming to become the best tech lawyer I could be.

Can you tell us a bit about the nature of your practice and what you focus on?

We are a tech-focused law firm. What I mean is we are driven by our interest in technology issues. Since working with technology companies is the most reliable way to be involved in cutting-edge technology law, that’s where most of our work comes from. We do a lot of the business law work that applies to just about every company, but we also take a particular interest in cybersecurity and privacy compliance, SaaS contracts, blockchain issues, software development planning, and more.

Beyond that, I really enjoy programming, which was an added benefit of my education that I didn’t expect, so I like developing solutions for our practice. We are a sincerely technology-forward law firm. We do what we can to stay ahead of the curve when implementing technology, and we see it as a measure of our commitment to customer success. The thrill of automation is just a bonus!

You are a successful attorney. Which three character traits do you think were most instrumental to your success? What unique qualities do you have that others may not? Can you please share a story or example for each?

Creativity, enthusiasm, and curiosity in equal parts make up the engine that has driven most of my endeavors forward. I think if any of those three were missing, my approach to the law would have been very different. Creativity means you put old pieces together in new ways; curiosity means you let yourself follow and investigate a train of thought without any obvious purpose or benefit; and enthusiasm means you put your whole effort into what you’re doing. I think what allows me to be there and feel confident in my instincts comes from a bit of a rebellious streak, a stubbornness, and a willingness to fail.

All of that is a rare combination in the legal field. It’s filled with risk aversion, naysayers, traditionalism, and criticism, all coming from very smart people — it’s hard to swim against that current.

I remember this one particular moment where all of those thoughts clicked for me. I was serving as the president of a nonprofit in the legal sector. We did a lot of fundraising and sponsored legal fellowships at other nonprofits and government offices. Every year we did the same two fundraisers, and there was this stagnant sort of sentiment that the job of the nonprofit was to simply hold those two fundraisers, whereas I was driven by the goal of raising more money for the fellowships. I suggested a simple idea, to reach out to the organizations who were benefiting from the fellowships, and ask them to seek donations from their own circles. The reaction was pretty strong, “you can’t do that,” “that’s bad for the fellows,” and more like that. I asked why everyone had such a strong reaction, expecting a reasoned, clear response, but there was none. It was a knee-jerk reaction against a new idea, simply because it had never been done that way before. We moved forward with that idea (and some other new ideas) and more than doubled our fundraising in that year alone, and the organization has sustained that level of success since then.

This dynamic has played out for me many times — from starting an academic journal on technology law, to launching a legal tech startup, to starting my own firm. Every step of the way there have been serious critics of those efforts, and they tend to be in the majority in the law, but all of those things happened for me despite the critics.

Do you think you have had luck in your success? Can you explain what you mean?

Oh, absolutely. I think luck is having access to an opportunity not under your control, and success requires other people. But luck isn’t passive. For every successful project or push that I’ve had, I’ve probably had five failed or abandoned projects for one reason or another. Sometimes, those failures create opportunities for other successes. The more irons I have in the fire, the more opportunities I create for serendipity to strike, but I am grateful for every stroke of luck along the journey of success.

Do you think where you went to school has any bearing on your success? How important is it for a lawyer to go to a top-tier school?

Yes and no. I went to a top-tier school, and I think it was right for me, but it’s not a requirement. I applied to UT Law because I was interested in being in Austin. I wanted to be in a tech center so I could pursue work with tech companies. I attended UT because it provided the right environment for me to pursue my interests. My classmates were accomplished and smart, I was plugged into a solid alumni network, and the professors were top-notch.

However, I’m pretty sure that my experience at law school was very different from that of my classmates because I was determined to make my education serve me. I didn’t want to go through the motions; I knew what I wanted and I took advantage of the resources available to me to make it happen. You can do that anywhere.

Besides, I’ve met lawyers from institutions of all calibers, and I don’t think any flaws or distinctions I’ve seen have been a result of the school. Excellent attorneys can come from unremarkable schools, and excellent schools can produce terrible attorneys, it’s largely what you make of it. Although a better school will make it easier for you to find those opportunities.

Based on the lessons you have learned from your experience, if you could go back in time and speak to your twenty-year-old self, what would you say? Would you do anything differently?

Planning things out is great, but nothing beats momentum. Taking steps forward is better than making a perfect plan, and don’t worry about things going wrong, you’ll be able to deal with it. Don’t look to other people for direction, they can help you with steps along the way, but only you can find your source of inspiration.

This is not easy work. What is your primary motivation and drive behind the work that you do?

The desire to help people accomplish their dreams is a big part of it. I get excited when my clients are excited about their business goals. I love working with startups because they have the drive to change the world one step at a time, and I get to be a part of that. I also get a sense of accomplishment that I’m building something bigger than myself. My goal is not to just have a law practice, I also want to bring meaningful, positive change to the legal industry. If one of those two motivators is not present, there’s a good chance that we won’t take on the work — we make efforts to live our values within the firm.

What are some of the most interesting or exciting projects you are working on now?

I went to law school to become a technology lawyer, but some of the most exciting stuff is using technology to improve the practice of law. Some big ideas that were never possible before are now within reach with the aid of technology. Some side projects I’m working on include standardized privacy policies for laypeople, automated document review, and predictive analytics for legal drafting.

Beyond the technical side of things, we’re making a push internally to develop space commercialization, AI governance, and corporate social responsibility services.

Where do you go from here? Where do you aim to be in the next chapter of your career?

We’ve taken a creative approach with the structure of the firm, and we’re looking forward to pushing that forward. We’re looking to create tiered services that can be efficiently administered in-house, from pro bono services all the way up to our large corporate clients, we want to provide services that are tailored to their specific situation. That’s more of a long-term goal, but it’s one that we’re eagerly working towards through various technical and personnel measures.

Without sharing anything confidential, can you please share your most successful “war story”? Can you share the funniest?

I have a pretty good one I like to share from when I first became an attorney. I met with a potential client to discuss his issue. It was a complicated set of facts, was dependent on a lot of external factors, and required more digging to say anything definitive.

The potential client kept trying to reexplain his position to me as if he was trying to convince me to be “on his side,” perhaps thinking that would change my initial analysis. I told him I couldn’t be any more definitive until he was a client and I did some more research on his behalf. He reached in his pocket and threw a 5 bill dollars on the table, and said, “there, now I’m your client, can you help me?!”

While dramatic, I told him that he’s still not a client, and I still didn’t have any clear answers for him. I later declined to represent him.

Ok, fantastic. Let’s now shift to discussing some advice for aspiring lawyers. Do you work remotely? Onsite? Or Hybrid? What do you think will be the future of how law offices operate? What do you prefer? Can you please explain what you mean?

We are 100% remote. We initially had an office space because “it’s what attorneys do,” but even before the pandemic we gave up our office space. We realized that almost all of our clients didn’t care whether we met in person or not, and the ones who insisted on meeting in person tended to not be great fits for our firm culture.

We’ve been much happier ever since. We can accomplish this since we are largely a transactional practice — if we were trying criminal defense on complex cases you’d almost have to meet in person. I think the requirements of having an office are somewhat a function of our time. As the younger generations become more dominant demographics in the client population, I think the need for office space will continue to diminish. Depending on how the courts go with remote trials, I could see even some litigators being able to avoid having office space (if they aren’t already out there), but time will tell.

One of the biggest challenges with litigation offices going fully remote is the inability to read body language. People forget that lawyers are solving human problems, with human players. The answer isn’t always just about the law, and whether that’s a good thing or a bad thing will determine how welcome virtual law practices are.

How has the legal world changed since COVID? How do you think it might change in the near future? Can you explain what you mean?

I think that Covid has created opportunities for lawyers who are willing to take advantage of them. With the whole economy going virtual, people have been forgiving of new practices within a workplace — it’s a chance to try new things without the same risks that may have been present in the past. Hiccups in creating new CRM processes are better understood, being completely remote has made people accept the use and frustrations that come with technology, and it’s a chance for an archaic industry to blast forward.

We often hear about the importance of networking and getting referrals. Is this still true today? Has the nature of networking changed or has its importance changed? Can you explain what you mean?

I think networking is and should be enjoyable. If it’s not, you’re doing it wrong. Networking is about making connections with other people. Sure, it’s helpful to your business, but that’s because people gravitate towards people and businesses that they feel a connection to. Networking with an eye towards the bottom line is putting the cart before the horse; plus, it’s boring!

The same thing holds true for networking today. Networking today features technology much more prominently, but it’s still easy to see who is seeing you as a money-making opportunity. Connect with people and engage with them about what excites you. There’s always something to be found in common with the other person, so there’s no need to fake it, and there’s no need to hold your enthusiasm back either. Share your business successes and struggles with another person from a place of sincerity and you’ll be much more likely to see your referral network blossom.

Based on your experience, how can attorneys effectively leverage social media to build their practice?

As I mentioned before, reach out to people who you admire for one of their accomplishments, or who sparks your curiosity, and be genuine about it. Use your firm’s social media to speak with a voice — this isn’t LRW! Be thoughtful about your brand identity, and recognize that it’s distinct from your personal identity. It takes some trial and error to figure out who you are, the same is true for your brand — don’t be afraid to try new things with social media!

Excellent. Here is the main question of our interview. What are your “5 Things You Need To Become A Top Lawyer In Your Specific Field of Law?” Please share a story or an example for each.

1.Make Mistakes — I’m not talking about your clients or cases. I mean try new approaches to practicing and understanding the law. If you’re not making mistakes, you’re not trying hard enough.

One of my earliest mistakes was trying to provide legal services as cheaply as possible. This wasn’t about racing to the bottom, I wanted to help people as an attorney. I calculated the minimum dollar amount I would need to make per hour to make an okay living, and focused on automating as much of the process as possible to improve efficiency. The only problem was that no one trusts the cheap attorney! It’s a problem I’m still trying to figure out, but I’ve learned to not focus on that side of the practice as a way to make money.

That idea didn’t pan out, but that mentality has allowed me to innovate in other ways. For example, I was involved in the drafting and development of one of Texas’ major cybersecurity bills, not because I’m the smartest person, or know the most people. I was able to participate in that because I know that making mistakes is not fatal to a person’s career, it’s just part of the deal when you’re trying to make big things happen.

2. Ignore Naysayers — Any time you prepare to take a leap, there are going to be a lot of people who tell you that you can’t, or shouldn’t, or won’t. Sometimes they’ll be right, but in the legal profession saying “no” is the rule. Be incredulous. Ask why not. Oftentimes the doubts are based on indigestion more than some actual problem. Criticism has its place, but scrutinize it before you accept it.

When I was first planning to start my practice, I told anyone and everyone about my plan. 90% of people I spoke to said it was a bad idea. They said I should go work for a big firm first, get some experience under my belt with someone else, save up some money at another job, and then go for it. When I dug into the issue, the rationale wasn’t that they had seen other people fail, or that they had failed, or that there was any particular reason, it just wasn’t how they had done it. The 10% who said go for it? They had started out doing something nontraditional and loved it.

It’s human nature to extract value from our experiences whether they were good or bad, which is why it’s hard to look back and say you would trade that time away to do something else. That’s great, awesome, but it’s not a reason to fear other paths.

3. Have Fun — Loving what you do makes you want to do it well. The more compromises you make the less fun you’ll have, and before you know it, you’ll be stuck in a rut instead of embracing new challenges.

I’ve floundered before. I’ve felt like I had to be a trial attorney, or write legal briefs, or do other traditional lawyerly tasks to be a “real” lawyer, but I spent so much energy trying to meet those expectations that I didn’t have the energy to do what I’m good at. I’m good at strategic thinking, I’m good at executing big-picture ideas, I’m good at thinking through legal issues from beginning to end. Those are valuable skills, and not everyone has them. Freeing up my time to do those things I excel at lets me better serve my clients and my community.

4. Surround Yourself with the Right People — They say that you become a mix of the five people you spend the most time with. Make sure at least one of those people is pushing themselves forward as much as you are.

I had to join several professional groups before I found the right mix for me. A lot of the traditional organizations that lawyers join just did not suit me. Once I found my crowd, I was able to start making bigger strides. I connected with a group of attorneys who are really into technology; I surround myself with entrepreneurs who are trying to manage big dreams; I host events where people are at the cutting edge of the law and technology. All of these networks feed my drive and my creativity, which is different from what I might find elsewhere.

5. Learn to Put the Work Down! — If you never take a break, you’re going to wear yourself out and be unable to find motivation. I have the most trouble with this. It’s easy to make the excuse that you should be working at all times of the day, “I need more money,” “I actually enjoy this so it’s not work,” “it’s only temporary,” you have to take care of yourself or your output will suffer.

The worst burnout I’ve ever had, I had probably taken on too much responsibility. I was constantly on the hook to make decisions, coordinate projects, and attend events. At the end of that period, I remember feeling taken for granted by the people around me, and it damaged my relationship with them. I was less inclined to pick up responsibilities or projects, and I fell into a short period of inactivity where I basically recovered from the burnout.

Now, I try to take at least one day a week where I go and do something for myself or my family where I’m unplugged and can disconnect from responsibility for a while. Whenever I do, my motivation seems to get recharged.

We are very blessed that some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch, and why? He or she might see this. 🙂

I tend to get excited about the projects other people are working on, and there are so many people who I would love to chat with about their experiences. One of my most recent projects ( is about regulation to improve competition and address free speech concerns with social media companies. I’d love to talk it through with Senators who have recently been active in the space, such as Senator Warren or Senator Klobuchar.

This was very inspiring. Thank you so much for the time you spent with this. We wish you continued success and good health!

Thanks for having me, and looking forward to our next chat!

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