Sabih Siddiqi

0:00From pre-med to the lowest paid employee

ChristianneSabih, welcome. What do I need to know about your earliest context to understand the man you are today?

SabihA couple of things defined me. Being an only child, for one. That's come up more often now that I'm running the company. And when I was very young we traveled a lot. We lived in Africa, London, Abu Dhabi and eventually New York. That gave me a worldview I didn't even know I had until college, where there were a lot of international kids and I realized, I really do see the world the way they do.

I started at Boston University as a pre-med student, really gung-ho about becoming a doctor. Not from outside pressure. It was the idea of helping people, and what's the most direct way to do that if not becoming a doctor? It also meant success. There was a charted path. It was long, but if I accomplished it, it would mean something. It certainly was not the path for me. And the path I'm on now is completely uncharted. Not med school, not law school, not partner track.

Things like cancer, and the open-heart surgery I had at seven, I think of as notches on the belt. They accelerated my growth. But it was what I learned after each one that shaped me: digesting what happened and deciding who I wanted to be. Then law school, practicing law for nearly seven years, and now being a first-time founder. And a last-time founder. I'm in it for the long run.

3:28Open heart surgery at seven, cancer at eighteen

ChristianneI'd love to dive into your health journey.

SabihToday I'm very health conscious, in a balanced way. Sleep on time, sleep better, sleep longer. Health is how you show up: for the company, for your family, and for the long run. I had open-heart surgery when I was seven. I remember all of it. It was a prelude to what was to come. I always thought I was healthy, but some things are outside your control.

ChristianneTake me to the day you were diagnosed with cancer.

SabihIt was December 2011. I was a freshman at BU, living in Warren Towers, which people called the zoo: thousands of people, shared bathrooms. I'd made a ton of friends, and it was shaping up to be a great few years. Academically I wasn't doing well. I just should never have been in pre-med. I kept trying at chemistry and bio, and I kept failing. Not F's entirely, but I should have learned my lesson early.

Right before finals, a friend noticed a small bump on my neck. Being the hotshot doctor I thought I'd be, I self-diagnosed it as a thyroid thing from exam stress, and partying a little too much. I went to Tufts Medical Center at six in the morning. The doctor on call said, it's probably a thyroid thing, but maybe we can get an X-ray just in case. We were both on the fence about it. At the time, I didn't even know the symptoms of Hodgkin's lymphoma, and I was experiencing all of them. I just didn't know how to put them into words. Right before I walked out, we decided, might as well get the X-ray.

The technician ran out with my X-ray. I put my shirt back on and walked out, and there were attendings and doctors all huddled around it. I thought, great, what could it be?

They made it as easy as they could. They told me what would happen, and they even called my parents for me. I can only imagine how hard that was for my parents. That was D-Day.

Then I had a decisionstay in Boston for treatment, or go home. Anyone close to me knows I do not do well with going backward. The one dream I always count as a bad dream is being back in high school, taking a class over. So taking time off from the path I thought I was on was a big deal. But even harder was the complete destruction of my identity. I thought I was the smartest kid on the block, with great SAT scores and grades coming in. And I had to understand that I'm not infallible. I'm not impervious. It was humbling, to say the least. It also saved me from a few things. I probably would have failed chemistry that semester. I got an incomplete, and the college worked it out with me.

I went through chemo and radiation, and it was a complete destruction and rebirth of who I was. I learned what really matters: family, what success really means, not getting bogged down in the weeds, seeing the silver lining. I don't know if I'd be a different person without that diagnosis, but I'd be a younger one. It added years. And I wasn't the only one affected. My parents probably went through more than I did. I'm their only child. I learned that family matters no matter what, and that their support let me do far more anyway.

I didn't talk about it with anyone until my junior year, with my girlfriend at the time. We spent a week talking about all of it, and we realized it had been a boot camp for me. It made me a better person. And now, as a founder, so much of what I learned there goes into leading the company every day.

ChristianneWhat did being diagnosed with cancer do to your relationship with control?

SabihI've always struggled with control. I wanted control over things I didn't realize I had no control over: how I'm feeling, how something turns out. What I learned is that we control very few things. How we perceive things, how we react, and the effort we put in. After that, it's up in the air. You can't control people or outcomes. You have to be okay with that, and more importantly, okay with the effort you're putting in every day. Out of a hundred, I'm maybe at seventy-five. We live in New York. We're all type A.

Last week I traveled, and there was a two-hour immigration line. My friends were freaking out. I checked whether there was a fast lane, and after that, that's it. I'm going to enjoy my time with my friends, in this moment. All we really have is the moment.

ChristianneIt sounds like you were choosing inner peace over controlling the outcome.

SabihAnd I don't know how I had that outlook at eighteen. Nobody told me. But when I was diagnosed, there was sadness, and I very quickly reconciled with the fact that this was happening and I couldn't do much about it. What else was I going to do, freak out every day? That wouldn't have changed anything. So I chose to deal with it, and dealing with it meant doing nothing. I was in the care of a loving family and medical practitioners doing the best they could. The harder part came after: the rebirth of identity. Who am I really, and what do I want to do?

I was home on Long Island for eight months, getting treatment at Stony Brook. I fought tooth and nail to stay in Boston. It would have been foolish. I wasn't going to be in class, and I'd have been too weak. There was a big aspect of loneliness, because my parents were dealing with their own huge ordeal while trying to be their best for me, and I'd left behind this fantastic group of friends and all that momentum.

I went back to college at the end of the summer of 2012, and it was surreal. People say the world keeps moving, and it did, but the world I'd left was still there. My friends were still there. What wasn't nice was: who am I now? Am I still the super-smart kid on the pre-med track? No. I'm not an unmovable object. You have to flow with life.

ChristianneTake me to one day when you were getting chemotherapy.

SabihSurprisingly, those are days I never think about. I used to love my hair, and in chemo you have no hair. You're weaker. Things hurt that you didn't know could hurt. Even when it became routine, I was never okay with it. We were always smiling, but there was always a sadness to it. And because it was so sad, I don't think about it. Speaking with you today might be the first time in fourteen years I've thought about those days. There's still trauma and sadness there.

ChristianneAnd back at college, your friends could sympathize, but they hadn't been through it.

SabihThey couldn't, and I couldn't expect them to feel what I felt. I wanted some leniency on the days I was down, and I couldn't explain it. There was a reacclimation curve. We were nineteen. We were kids.

16:56Why leaving medicine wasn't quitting

SabihI launched right back into pre-med. I hadn't learned my lesson yet. It took about another semester. And honestly, without cancer, I might have stuck with pre-med even longer, because that's my nature: persistence. But the whole ordeal taught me that perseverance should be targeted. It doesn't have to be blind. Letting go of pre-med, as trivial as it may sound, was a big deal, because I'd never quit anything before. Looking back, it wasn't quitting. It was a pivot I should have made earlier.

ChristianneWho were you letting down by changing your career?

SabihMe. So I thought. I thought I might be letting down my parents, who'd put so much into raising me. But all they really wanted was for me to be happy, healthy and successful. And I wasn't letting myself down either. I just had to learn not to stick with something that doesn't make sense, that I'm not good at, when there's a whole other world I was better suited for.

And once it clicked that I needed to let go, letting go became easy. What I've always been good at is building systems. So I built a scaffold to get myself off that path: picking the right classes, talking to the right people, and begging my organic chemistry professor to let me off with a C. I ended up doing better than a C. Once the decision was made, there was no grief. Once you make a decision, you keep moving forward. If I'm grieving over something, there's either unresolved trauma or unresolved learning.

18:19What big law taught him, and what he had to unlearn

ChristianneYou went from medicine, a tried-and-true path, to law, which some would say is a parallel track. Doctor, lawyer, engineer. What do you think about that?

SabihYes and no. The education and mindset are very different. I have a lot of doctors in my family, and they see problems more like engineers do, from a scientific background. I was a litigator, specifically in dispute resolution, and I was always very solution oriented. I should always have been on a pre-law track. To me, being a lawyer was about communication and how you solve problems. I got into debate, mock trial and mock mediation, and I won every mock mediation competition my first year. That's when I knew. What drew me was solving esoteric problems involving people, and turning my thoughts into conversation, not arguments. People say law school teaches you to argue. I'd say it teaches you to be coherent: step back, form your thoughts, then express them.

ChristianneWhat did working in big law teach you that you use daily as a founder?

SabihSo much. If I weren't a lawyer, I don't know how I'd start a company. Contract drafting, dealing with vendors, hiring, firing, dispute resolution, strategy. So much of litigation is strategy: building the plan for how you get to a solution. Literally everything I was good at, I use and sharpen every day now. It's still early in the journey, so I don't want to get ahead of myself.

ChristianneAnd the opposite question. What did you learn in big law that you're now unlearning?

SabihThe main thing, and lawyers everywhere will relate, is risk aversion. You're working for your clients and you have to hedge risk. Trusting your gut isn't really a thing. It's all analysis, line by line, to make the most informed decision. Becoming a business owner is the opposite. You open yourself up to so much more risk. Would a lawyer advise it? No. But a lot of where we are today has come from gut feelings, and those gut feelings are informed by all my experience as a lawyer. It would have been crazy to tell my younger self, trust your gut in litigation. So I'm unlearning risk aversion and turning it into a weapon instead of a weak point.

ChristianneWhat if you had built Irys as a junior attorney?

SabihIt wouldn't work. With one, two or three years as a big law associate, you know nothing. You're still doing menial work. Law school doesn't teach you to practice law. You get the keys to the room and spend years learning to navigate it.

And even as a senior attorney, if I ran a company exactly like a lawyer, it wouldn't go well. Lawyers are service providers. As a service provider, you're at arm's length from the problem. I'm never at arm's length from the problem. The problems are mine. Even managing partners of law firms are very different people from associates, because they take on different levels of risk.

One of our advisors, Eric Friedman, was the chair of Skadden, one of the top law firms in the world. Every conversation I've had with him, he listens intently, and only when I'm done does he give feedback. As a lawyer, your feedback is the solution, because clients pay thousands of dollars an hour for a solution. But as a leader, you guide people toward the solution that's best for them, because they know their own situation best. I've seen the same with one of our senior investors, who I think is a sage as far as Silicon Valley goes. It's all about guidance.

28:25We didn't build a startup, we built a company

ChristianneThat resonates so much. Building a media business, there's so much unsolicited advice that isn't helpful, and asking to be told what to do can work against building your own instincts. In banking, I never built those instincts. You're always told what to do.

SabihThere are two ways to understand something. You learn it by doing, which is the best way to internalize it. Or you're told. But in company life, it's not A, B, C. There's so much in between. Reaching a conclusion through your own learning is so important, which is why real guidance matters, not being told what to do. I can only speak from my perspective of your situation. I'm not you. You can only lead the horse to water.

And it relates to our product. We're taking everything I learned as an attorney and combining it with AI and machine learning. It's Palantir meets Bloomberg. Intelligence meets execution. That needs experience behind it, something deeper than the surface. It doesn't come from wrapping an LLM and calling it a day. It comes from building infrastructure, which is what we're building. So the daily decisions, technical or talent, aren't black and white.

I don't consider us a startup. I consider us a true company, like the companies and CEOs I dealt with as a lawyer. To me, startup life is a young, naive journey of figuring out what will work. We didn't start from zero. We started from a deep understanding of the problem, because we'd lived it. And even as a junior attorney, my firm put me out there on business development, so I got a lot of exposure to the business of law. I was already learning to be an operator.

35:43The waterless car wash, and moonlighting a company

ChristianneSome people listening are first-time founders who think their first business will be a blowout success. Tell me about the waterless car wash, why it didn't come to fruition, and why it didn't end your career as a founder.

SabihIt had a short life cycle, because I realized early that it could be fruitful, but only from a cash perspective. Going through the motions of ordering the machine from overseas, planning to deploy it in parking lots and hire people, I realized it would take years, it would be capital intensive up front, and the outcome wasn't what I wanted. What we're doing with Irys isn't for the money. If it were, it wouldn't motivate me or my co-founder.

A more recent oneI bought a property in Miami, intending to rent it short term when I needed to be in New York full time. I did every bit of diligence I could. I'd have gotten an A-plus-plus from PwC. At first I was making double or triple the carrying cost. But there are always intangibles, and anyone who says otherwise doesn't have enough experience in business. Even though the building allowed it and it was properly zoned, there was so much opposition to short-term rentals in Miami that the window closed. The business turned on its head.

Two lessons. There will always be things out of left field, no matter how much diligence you do, and the only way to prepare is to brace yourself mentally. Every day I get emails about Irys I didn't see coming. And more important: whatever you're doing better be worth it. Was it worth my time for so little outcome on that rental, even if things went smoothly? Absolutely not. Understand your motivations and align them with your business.

With Irys we got lucky with timing, and with the kind of business it is. There's a cash component: it's been a year since we launched our paid product, and we're doing really well. But there's also a larger goal that keeps us going no matter what: changing the practice and business of law, and making legal services more accessible. I'd say we're about 25% of the way there.

When I came up with this in late 2023 and 2024, I was an associate becoming a senior associate, potentially on partner track. How am I going to do this? Nobody talks about the how. There are YC videos every aspiring founder should watch. I watched a playlist of about twenty-one, a couple of times over. But the how is persistence. If you keep having conversations and taking tangible steps, like registering an LLC and getting insurance, the micro steps make the macro picture. Within a few months, we had a company, engineers, lawyers and customers. You get up every day, no matter how you feel, and execute.

ChristianneSo you were taking steps to build the business while you were still in big law.

SabihAbsolutely, and I did it in a professional and responsible way, because we were working with clients. It was a big juggling act, and I did it correctly, and I'm thankful for the support from my firm. By the time I quit, I'd taken so many steps that it made sense. I remember the conversation with my senior partner. It was a natural conversation for both of us. It wasn't, Sabih's leaving. It was, okay, this makes sense.

He knew I was business oriented. We'd come up with a lot of solutions together. We rewrote the entire technical terms and conditions for a large cruise company dealing with a tech vendor. Someone actually writes those, and I wrote pages of them. He said, that's a really good business solution. The firm probably hated me, because I didn't bill that much. I'd built systems to handle the work, and I was always looking for the fastest route to where my clients needed to go. That's much better applied in business than as a lawyer.

45:25One week of runway and a demo that crashed

ChristianneIf someone listening is a founder and starting to see the writing on the wall, with that little voice saying this might not be the right path, what would you say to them?

SabihMind my language, but: fucking listen. Whether you're in a career and see you should pivot, the way I saw how AI could change legal practice and the incumbents were dropping the ball, or you're in a business. I've seen founders like me where 90% of it stays aspirational. All talk. When you get that gut feeling, act as soon as possible. That doesn't mean burn every bridge tomorrow. It means start taking real steps. Whether it's to start something or end something, listen, and set up a system to get there.

I've talked to friends who missed the boat. They would have been first, and they didn't act. They listened, but not deeply enough. And vibe coding something today isn't enough. There's a big difference between building an app and selling it, being compliant, having a sales team, having insurance. If you do all of those things, you'll have created a company, and a new life for yourself.

When I started, I didn't even know the difference between an AI engineer and an ML engineer. I was getting quotes and talking to people, and there were plenty of teams I could have signed with that would have led me completely astray. There would be no company. You have to sift through the bullshit fast. We started with zero engineers. Now we have a whole team.

ChristianneYou mentioned there was a moment when Irys could have died.

SabihOnly recently did we cross the line where we know we're going to be something, and we're humble enough to know things can change. There were times we had about a week of runway, in cash and in human capital. We started under a name that was my last name spelled backwards. Law firms have named partners, so we thought it was clever. Clients didn't know how to pronounce it. We do business as Irys now, which is a better name.

All we had was a chat window that didn't really work. We demoed to a top ten law firm, and they brought about twelve people: partners, the innovation team. Five days before that demo, we didn't have anything to demo. This was before Claude Code, before Lovable. You actually needed engineers to build it. One of our founding engineers was building the first version on the side, at a lower price, because he was intrigued. It kind of worked. Mostly it didn't. I was bootstrapping it, we were running out of money, and we had to pay engineers.

ChristianneTake me into the room where it failed.

SabihThe whole thing failed. Our pitch, and the product. There was an inverse relationship between how much we prepared and what we needed to do. I prepared for a week. But because we've lived the problem, we don't need to prepare to have a conversation. That was a pitch. Every sales call since has been a conversation. For fifteen minutes, something came up on the screen. Did it work? No. It was a chat window that gave a few answers, and then I think the database crashed, and it was the black screen of death. We talked our way out of it, and we still have a very good relationship with that firm. We're going to be doing more work with them.

It wasn't negative. We've been lucky that nobody has told us, you suck. They've all been constructive. Maybe because I came from where they came from, and the mission and the effort were obvious. We knew we'd wasted their time, and I think that came across. That demo set the trajectory for every demo after it. There was a time I was leading product, sales, admin and fundraising with my co-founder. I don't know how we did it.

ChristianneAny words for someone who's had a dead demo or a public bust?

SabihMy internal monologue isn't exactly PC. It's: fuck it. Something happens. Fuck it. Keep going.

51:07Radical transparency and deciding without full information

ChristianneWhat are you learning about delegation?

SabihAt a law firm, a legal project can be delegated precisely, because you know what to delegate and who you're working with. At a company there are so many moving parts: product, engineering, go-to-market, all their flavors, what we need today and what we might need tomorrow. And this is my baby. When you've done everything yourself, you wonder whether anyone can do it as well. What we've learned is that if you hire the right people and set the right expectations, they do the job better than you. It's been beautiful to see.

My style is hands-off. We set the goals, and I don't care how you get there. I won't micromanage. When I talk to sales, the question isn't, what are you doing today? It's, what are we doing today? We have two all-hands meetings every day, a dev meeting and a go-to-market meeting, and nothing is hidden. Everyone knows the sales, what's working and what's breaking, so we all hold each other accountable. Our engineers who build the product often provide support too, so there's no distance between them and the problem. Our senior engineers say they've never seen it done this way, but it works. I'm clear with everyone about our cash position, too. There's nothing to hide.

Now that we've run these cycles so many times, fallen down and gotten back up, there's no real way for us to fail. Nobody is breathing down our neck. We're raising a round with people we actually want to partner with. We've been so disciplined and honest internally that the only question now is whether we become a two-hundred-million-dollar company or a multi-billion-dollar company.

ChristianneWhat does decision-making feel like when you don't have perfect information and the stakes are high?

SabihThat's been a thing to overcome. In big law, and in banking, there are expectations of perfection. A legal opinion or a transaction can be perfect. I've written perfect emails. There's no such thing as perfection in a company. You have to execute. I learned that pretty quickly, because I'm older and I have all this experience behind me. And because the people we work with are so experienced, what we put out is often seen as perfect. I look at competitors and think, I can't believe they put that out, when we were questioning whether to release our own version. Thinking can be endless. Doing is planting a flag, putting your pick in the side of the mountain and moving forward. If you're static, that's dangerous.

ChristianneEvery CEO I've interviewed who came from banking or big law has said letting go of perfection was the hardest thing.

SabihI completely agree. And for me, the gut aspect has been liberating. Every time in the life of this company that we've trusted our gut, it's worked out. Our salesperson is a seasoned lawyer, our success lead is a seasoned lawyer, our COO is a lawyer, and our engineers have built and sold companies. So a gut feeling isn't just a gut feeling. It's the instant synapse of years of experience, trials and tribulations, bottled up. That's why we trust it.

ChristianneWhat would you recommend for someone who hasn't developed that gut feeling, especially in corporate?

SabihGo through the motions. Do your best on that vendor contract, that employment contract, and listen closely to what fails. Our independent contractor agreement is a great example. It started in one place and it's somewhere very different now, because we kept learning what worked and what didn't and went back and improved it. If you're not improving your systems, that's where you're failing. And if you don't have the business experience yet, just fucking do it. You'll learn along the way, as long as you keep iterating.

56:33Legal access, and what it means to trust yourself

ChristianneWhat do you hope your team or your audience understands about you that the public might miss?

SabihThat Irys is so much more than an AI company or a startup. The idea is to provide a huge benefit to society. Step one is lawyers working better, faster and smarter, with more time for their families and better work for their clients. Our clients already tell us how much time they're saving and how much more they can do. Step two is giving the general public better access to legal services. What we're doing over the next year, our board and investors have called revolutionary. And we're not listening to Silicon Valley. We're listening to the people using it.

I could have stayed at the firm with the golden handcuffs and become a partner. It would have been a perfectly fine life. My co-founder would probably be at NVIDIA making more than I would have as a partner. But we're here because of the larger goal. My co-founder and CTO and I are the lowest-paid employees in the company, by orders of magnitude, even now that we're close to profitable. If I can put another ten or twenty thousand dollars into other resources, that makes a difference. In the beginning, I was paying our team out of my own savings. I believed in the idea enough to put my neck entirely on the line. And when I made that decision, I jumped in with both feet.

ChristianneWhat regret are you trying to avoid?

SabihI don't live with regret. I try to make the best decision I can every day with what I know. The biggest regret I would have had is not starting this company. If we'd started even three or four months later, I don't think we'd be here. Timing is everything. I'd have regretted it for the rest of my life, and I've avoided that.

ChristianneWhat do you trust now that you didn't trust when you were younger?

SabihMyself. I have to trust myself to provide for myself entirely, not depending on family or a job. To make the right decisions every day, and to execute, because no matter what happens, I have to get up and do. I didn't have that trust in pre-med, or through the medical issues, because you didn't know. As Steve Jobs said, you can only connect the dots looking backwards. And time and time again, it's been shown to me that what we're doing is right. So I trust myself now.

ChristianneSabih, thank you so much for coming on.

SabihThank you so much for having me. We'll do the follow-up in a year.