💡 Founder Spotlight: Darby Wong

And it looks like we're live! So hey everyone, my name is Matthew and I'm one of the Customer Success Managers here at Cloudflare and today I'm with a really special guest that I'm extremely excited to introduce you guys to.

It's the one and only Darby Wong who comes to us from his legal startup Clerky.

Darby, how you doing?

Hey, pretty good. Thanks for having me. Yeah, absolutely. Thank you so much for being here.

I'm supposed to kick things off. Would you mind telling us a little bit more about your legal startup Clerky?

Yeah, yeah, definitely. So we basically build software and products to help companies and attorneys get legal paperwork done.

Our most popular products are for a company formation and fundraising.

Yeah, just thousands and thousands of startups have used us over the years.

And yeah, that's pretty much what we do. I love that. I love that. And I kind of want to double click on the first part that you mentioned that not only are you guys a service for attorneys, but also for startup founders as well, then, right?

So if I start a company, I can go to Clerky.com and get help with starting, become incorporated, for example.

Yeah, yeah, that's exactly right. So our current products are all self -serve.

So you can use Clerky to incorporate your startup, issue stock to the founders.

You can raise seed financing from investors.

You can hire employees, consultants. You can issue equity compensation, like stock options to your employees.

Basically, all the routine day -to-day legal needs that an early stage startup has.

I love that. And so once I register with Clerky and let's say I'm collaborating with my attorney, making sure that all the I's are dotted, all the T's are crossed and everything, I assume, will I have a dashboard that I can see?

Or how will I be able to visualize that journey, if you will, that I'm going through with all the paperwork?

Yeah, yeah.

That's one of the cool things about using Clerky is that we have the products to help you get the paperwork done correctly.

But then after you do it, you get a dashboard that shows a summary of everything you've done.

So you can access the documents that you've completed.

But you can also get a summary in terms of how much money you've raised, how many employees you've hired, who's on the board of directors.

It's just a visual overview of your corporation. I love that. A view of a corporation all in one place, in a single pane of glass.

That's fantastic. Yeah, yeah.

It's super cool. Perfect. And tell me a little about, I mean, I haven't attempted to start multiple companies in the past, where oftentimes I feel like the barrier to entry is just that first step of incorporating or getting that LLC.

And then once you get the LLC, it's the stress of, oh my goodness, is it strong enough to withhold if something happens?

I'm curious, I mean, how did you come up with a vision to start Clerky?

Yeah. So I used to be a startup attorney. I worked at a law firm called Auric, which is one of the major startup law firms out here in Silicon Valley.

And my co-founder, Chris, was an attorney there as well. And we both had engineering backgrounds.

So, I mean, basically, we were just helping startups, helping our clients.

And what happens is every time a company raises venture capital, or they get acquired, or even IPO, you've got to basically review all their legal documents and make sure that there's no issues there.

And what we were seeing was that a lot of early stage companies were trying to save money.

I mean, our legal fees were really high, so they were trying to save money doing stuff on their own, using other online services, or even a cheaper lawyer sometimes.

And a lot of times it was just causing this huge mess that we would have to clean up later.

It would delay their financing or acquisition and cost them a whole bunch of money.

It would have been a lot more efficient if they had just come to us in the first place.

But at the same time, we knew why they didn't come to us, because we were expensive.

So we really, with our engineering backgrounds, we just sort of, we thought like, hey, we could really automate just getting this paperwork done correctly.

It's not rocket science. You just have to know how to do it. And so that's really sort of what led us to start Clerky.

And so we started with a convertible note financing product, which just became really popular within the Y Combinator community.

And after a couple of years, we launched our company formation product, which just quickly became the most popular way for startups to form.

And the whole idea is that if you use Clerky, whether it's with or without a lawyer, you're using forms that have been vetted by us.

We work very closely with just some really, really good startup lawyers in various law firms.

And as long as you sort of stay on the rails and use our products, you shouldn't really have to redo anything when it comes to, when it's time to raise money from an investor or even get acquired.

It should just all sort of fall into place. So that's sort of a little bit about why we started Clerky.

Amazing, amazing. And talk a little more about your background.

I know you hinted at it earlier, but did you say that you have not only an engineering degree, which is an incredible accomplishment in and of itself, but also you are a practicing attorney as well?

Yeah, yeah, that's right.

So yeah, I went to the University of Washington, got my bachelor's in computer science there.

For a very brief period of time, I was actually at Redfin, which was, at that point in time, it was like, I don't know, 10 people or less.

It was a very, very small company.

But then went to law school after that. I just went to Harvard for law school and then came out here to work at ORIC.

Actually, for a long time, I didn't really want to be a lawyer.

I had always wanted to start a company.

But it was just a really good opportunity to sort of see how everything worked behind the scenes, learn about all the legal aspects behind startups.

So it was a little bit of a surprise in that I never imagined I would start a legal tech company.

But while I was working at ORIC, the problem was just so large and obvious that it was just kind of a difficult opportunity to pass up.

Absolutely.

And tell me a little bit more about, you mentioned that you went to Harvard, which is incredible.

So I got to ask, how was Harvard, first of all? It was great.

It was great. I think of it as like an intellectual playground. So yeah, I mean, just like a huge variety of courses.

And I think everybody that goes there has a different objective.

So if you're looking to get the best grades in the class, then maybe it's not as fun, because you've got to stress out a little bit more.

But if you're looking to get by like I was, it was just really nice to be able to take a variety of different courses.

You can cross-register at the business school.

I took a lot of negotiation classes. It was just really nice to be able to explore whatever was interesting.

That's incredible. And you also touched upon a point that I've always been curious about myself, right?

Which is where, if you are able to get into the amazing Harvard Law School, you're also able to take courses at the business school as well.

Would you mind talking briefly about what that means?

And for anyone that perhaps is listening and aspires to go to Harvard one day and is entrepreneurial and also maybe legally minded as well.

Yeah, yeah, definitely.

I mean, it's been a long time since I was a student there, so I don't know if anything's changed.

But roughly the way it works is the first year, there's not a whole lot of discretion.

There's the mandatory classes that are pretty much standard across all law schools.

But then the second and third years, you have a lot of discretion.

You can cross-register in classes, basically any school at Harvard.

But there were classes that were more closely related to business law, which I was interested in.

So I got to take some classes around basically deal-making and negotiations, which seemed interesting to me, both in terms of the area of law I was thinking of practicing in, but also it just seemed useful for anything else that would come up after being a lawyer, like starting your own company.

So yeah, I highly recommend it for anyone that has the opportunity.

It's a great, great experience. Incredible, incredible. And I love how you referenced business law too.

Through my undergrad, business law was by far one of my favorite classes.

Yeah, and Ms. Novak, if you're listening, thank you so much.

Nice. So I absolutely love that class. And it's something that in today's world, I think it's just so applicable in everything that we do.

And so I love how you were able to not only take legal coursework, but also take negotiation classes in business law.

That is wonderful. And I know you mentioned that you weren't too sure if you wanted to go into law, but you did know that you were interested in maybe one day starting a company.

What do you mind telling me a little bit about the moment that you decided, I think I'm an entrepreneur and this is something that I want to do?

Yeah, I mean, I think that must've been in college.

So I was in computer science and this was sort of right after the dot-com bust.

And so there was a lot of innovation going on in Internet technology, sort of like web 2.0 was sort of just coming into reality.

And yeah, I mean, it's just one of those things where you're sitting around with your friends, other computer science students, and you're looking at sort of like the skills you have, like what's possible.

And you're looking at what's out there in the market.

And it just seemed like you could totally build something that was useful and better than whatever else was out there.

So yeah, I think that was a huge part of it.

I think I would say one factor for me was I started working part-time jobs when I was like 14 or 15.

It was mostly just a way to kill time to be honest.

But a lot of the jobs I had were, they were interesting at the beginning, but they very quickly sort of became a little boring.

And so I just had this thought, it's just like, I'd much rather work really, really hard for a shorter period of time and compress everything there and then basically retire early.

And yeah, I think there's really sort of roughly two ways to do that. Like one's through investing and then one's through entrepreneurship.

And I think maybe just because of my background with computer science and everything, it just seemed a lot more natural to build things.

Hey, that is incredible. And talk to me a little bit more about your experience at Redfin too.

I always wonder, there you were when the company was less than 10 people.

I mean, you could fill a room with the entire company.

And nowadays, out here in the Bay Area, you see Redfin signs everywhere.

Yeah, it's crazy. I mean, do you think that had any influence on you as you began to think about, hey, maybe I'll become a founder one day myself, especially working on Redfin when it was so small?

Yeah, well, it definitely, to me, it's just sort of an illustration of the importance of perseverance.

Because when I was there, yeah, I mean, it was super small.

They hadn't raised the Series A yet.

I think they just raised the small seed round. And I was actually only there for less than a month, really.

And what happened was they had failed to raise the Series A term sheet, fell through, basically.

And basically, the entire engineering team left.

And I was sort of the newest member of that team. So I just sort of left with them because I didn't be the only one left behind.

And so honestly, going into law school, even, I didn't really have any expectations around Redfin.

So it's really just sort of incredible that they were able to survive all that and eventually become a public company.

It's sort of like they went from nothing to a little something and then almost died.

And then I'm sure there were other ups and downs along the way, but now they're obviously very successful.

Right. Absolutely.

And bringing it quickly back to Clerkey as well. So I am curious, so given your background in law and when you yourself were starting a company and you yourself were going through the formation paperwork and the hiring paperwork and even documenting your funding as well, what would you say were some of the challenges that you, even though you're an attorney, have experienced yourself since you weren't able to use Clerkey since you were Clerkey?

Yeah. No, that's one of our regrets is not being able to have used our own product to start Clerkey.

Yeah. I mean, for us, luckily, we didn't have sort of the challenge of having to figure everything out because we were very, very familiar with that process.

But it's still, you know, there's a lot of clerical work, which is basically, you know, what our software helps remove, you know, around just making sure that everybody signs everything, everything's dated properly.

It sounds super simple, but, you know, it's one of those things where in practice if you had a thousand people do it, like one person would get it right.

Maybe, you know, you'd be lucky. So, yeah, it's really just sort of, you know, making sure all the numbers are right, everything was dated correctly.

We got the 83 bill actions filed, which is a huge thing. And, yeah, keeping everything organized after that.

Right on. And I'm curious, too, you know, I think what a lot of founders struggle with is, you know, they might be super entrepreneurial, they might have an incredible idea, they might have the team behind them, you know, but they may have a job that they love or a job that is able to pay the bills.

And, I mean, very much like you, you had a fantastic job before going out on your own.

If you don't mind me asking, at what point did you decide that, or I guess what allowed you the confidence to say, you know what, I'm going to do this and, you know, jump off the deep end and build what you built today?

Yeah, yeah. I mean, you know, honestly, it was, you know, probably less about confidence and more, you know, sort of frustration, you know, it's just, it's sort of like, you know, I guess, like, I really view starting a company as, you know, in many ways, sort of like an exercise and just pushing yourself as far as you can go and, you know, as far as you can grow professionally and personally.

And I just, you know, I just felt this immense frustration, or I guess like impatience about sort of like not being able to do that.

So it was really sort of that impatience, you know, slash frustration that really just, you know, pushed me to, you know, to let the law firm know that I wanted to leave and do my own thing.

And they were really great about it, actually. I mean, I think a lot of times people have, you know, reservations around, you know, giving notice to their employers, you know, to go start their own thing, which I think is, you know, it's fair sometimes, but I was lucky, you know, they were totally understanding and they actually, you know, let me work part time while I sort of like nailed down the specifics of what exactly I wanted to do.

And they even let me work out their office afterwards.

So yeah, I had a pretty good experience there. That is wonderful.

You wouldn't be able to work out of their office. That is, that is literally the best case scenario right there.

Yeah. Yeah. Yeah. No, they were super, super accommodating.

And so, so yeah. Yeah. I think it was honestly just this drive really.

So less about, you know, sort of like confidence that like, yeah, I can do, I mean, I guess you have to have that to have that drive, maybe.

But it was really just, you know, sort of like every day that you're not sort of pushing yourself, you know, just feeling frustrated that you're not sort of living up to your potential.

Right, right, right. And your co-founders as well, were they also working at the law firm with you then and you guys together created Clerky?

Yeah.

Yeah. So Chris, he actually sat, you know, right next to me, our offices were right next to each other.

And yeah, we worked on a lot of deals together. The last deal we worked on was actually Heroku's acquisition by Salesforce, which was at the time the largest exit for Y Combinator.

So that was kind of cool. And yeah, you know, it was really, I mean, that's really how Clerky was born was, you know, we were just like working on deals and it was, I think it was like 2am one night, we were just like, this is crazy.

Like, why does the same, you know, the same problems keep popping up, right?

Like someone should really automate this. And it just so happened that both of us were looking, you know, we had sort of decided that we knew that we weren't sort of like going to go on a partner track for, you know, the law firm.

And so we were looking at sort of like, what else can we be doing here?

And so yeah, it was just a good opportunity to work together. That was great.

And I would love to learn more about, you know, Clerky now, right? You referenced how, you know, you guys are at two in the morning, you guys are like, there's got to be a better way here.

If you could, I would love to learn more about, you know, Clerky's, you know, startup culture and just culture as a whole when it comes to working for Clerky.

Yeah, yeah. So yeah, we're, I would say like, almost like polar opposite from a law firm, you know, where I would say, you know, there's just a lot of inflexibility around scheduling and not, I don't blame that on the firm culture.

It's really just sort of the nature of, you know, client driven work.

But yeah, we're sort of like, we have a lot of, you know, just sort of like philosophy around giving people a lot of flexibility, you know, just sort of with the idea that, you know, I think, you know, with a more rigid, you know, work environment and schedule, there's a lot of inefficiencies that come out of that.

So, you know, I always just think about even just like, you know, getting a haircut, for example, you know, if you, you know, if you have a popular barber on the weekends, the line is like super long, right?

And on the weekdays, the line is really short.

So it always made sense to me, and I was, you know, just thinking like, it'd be really nice if I could just, you know, go to the barber on the weekday, and then just work a little on the weekend, and, you know, sort of like eventually, ultimately save time.

So that's, that's one thing we really try to foster here is just, just a lot of flexibility.

Obviously, there are business needs, you know, that that sort of do add some constraints.

So like, for example, like you're doing this show, it has to be at this particular time, right?

So there's not much we can do about that.

But, but the idea is to sort of like not introduce sort of unnecessary restrictions and inflexibility.

Yeah, you know, culture wise, I would say everybody at the company is, you know, just like really earnest, down to earth, hardworking.

You know, the phrase that always comes to mind is, is, you know, from from the South Park theme.

So I don't know if you've watched South Park, but there's this part of the theme song where they say humble folk without temptation.

And that, that to me, like almost like epitomizes the people that work at Clerky.

You know, we're all just, I would say, really passionate about, you know, what we do.

You know, both, both, you know, what we do as a company, but also the craft that each person has.

So, you know, like, we have engineers that really just love the art of software engineering, design, designers, customer ops, you know, like, like, just to really make a craft out of helping people.

That's one thing that we really look for in everyone.

Just, just really just like a strong passion for, for what you do.

And I think what's behind that is just sort of, you know, this belief that, you know, if people are really passionate about what they do, that ultimately comes through their work, like no matter what.

It's, it's often difficult to quantify or measure, but, but it, it does matter, I think, in the end.

I completely agree. And, and, you know, just going to Clerky .com, for example, you can see, you know, the work that they've done.

It's incredible. I mean, your, your designers are wonderful, by the way.

Awesome. Awesome. Thank you. They'll be happy to hear that.

Yeah. Like the design team props to them. They do an excellent job and the entire flow of your website.

It's beautiful from a UI and UX perspective. And, you know, I think that passion, just like, you know, if they're passionate about the work that they do, it shows on, on your website.

And so I'm really, really glad to hear you say that.

That's really great to hear. Thanks for that. Yeah. I think it's, you know, it's one of those things, I think, you know, when you are really passionate about, about your work like that, it can often be, it can often feel like nothing is ever perfect.

You know, all you can ever see, you know, are the, are the problems.

So it's, it's definitely good to get an outside perspective on that and definitely share it with them.

Absolutely. Well, I'm a very big fan of, you know, clean, beautiful design and your team has really nailed it.

So excellent work.

Please do extend my feedback to them. Thanks. Thanks. I'll do. For sure, Darby.

And as we wrap up, wrap up here, I know, I know we were coming in at the five minute mark here.

I would love to hear from you, you know, what are some things that you'd like, you know, the viewers to know about Clerky?

Yeah, I think, I think the biggest thing is, you know, I, you know, it's, it's one of those things where, you know, I, there's no way for me to prove it really, but, but just for people to know that we're really, really obsessed with the quality of the legal documents that are produced, you know, from our products.

And the reason why that's important is because, you know, it's actually, I would say, you know, like we're, we're the exception in our industry.

So, you know, the thing with legal paperwork is that it's, it's what economists call a credence good.

So, so basically there's, there's, you know, after you've consumed the product, there's no way to really tell what the quality of the good is.

It's kind of like a vitamin, like you take a vitamin, like you don't really know what was in there.

You're just kind of hoping that, you know, does something.

So with legal paperwork, you know, there's, there's not really a good way for regular people to know how, you know, if it's, if it's doing what it purports to do unless, you know, it's sort of, you know, somebody sues you and then you got to take it to court or you have a lawyer review it.

But anyways, as a result, you know, I'd say a lot of services and even lawyers, you know, the, the bad lawyers, not, not the good lawyers, but the bad lawyers, you know, there's just the quality of the work is just not really there.

And a lot of times it doesn't matter because, you know, the startup maybe dies.

And so nobody ever looks at the paperwork. But, you know, if you want your sharp to go somewhere and you want to get what you're paying for, you know, I think it definitely behooves you to, to look for a service that that's higher quality.

And so that's something that we really pride ourselves on. And we spent, we just invest a lot in it because, you know, for us, there's, there's just like no point to even existing if we're not getting the legal paperwork.

Right. Okay.

And if I'm a founder and I want to get started with Clerky, how can I get started and, you know, work with you guys and, you know, look at the awesome dashboard and start collaborating with my attorney on, you know, for example, incorporation paper, how can I get started?

Yeah. All you have to do is go to clerky.com, sign up, verify your email address, and you're ready to go.

I love it.

I love it. Thank you so very much for your time. It's absolutely lovely, you know, to meet you.

And, you know, I sincerely appreciate you taking the time to tell us, you know, not only about your background, which is super impressive for one, but also, you know, telling us about how you're really changing lives out here, you know, with Clerky, you know, I was telling, I know we were talking before we hopped on here about just how important it is to have solid legal paperwork, right.

And for so many startup founders, you know, around, you know, the country and quite frankly, the world, you know, it can be challenging to, you know, have a group, you know, contracts or paperwork in place.

And, you know, so the work that you're doing is definitely recognized and super important.

So thank you so much. Awesome. Well, yeah, thank you for having me.

I really appreciate the opportunity to answer your questions and share more about Clerky.

Rendering to streaming.

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