20 VC FF 019: 500 Startups Week: Life As A 500 Startups Portfolio Company with Ashish Walia, Co-Founder @ LawTrades

Ashish Walia is the Co-Founder & COO at 500 Startups portfolio company, LawTrades. LawTrades aims to decentralise the traditional legal hiring process through providing an amazing marketplace of attorneys with domain experience in the startup world having worked with companies from the likes of YC, Techstars and 500. Ashish is also the Host of The Ashish Walia Show, a podcast dedicated to interviewing the latest and greatest world changing entrepreneurs, you can listen to Harry's interview on The Ashish Walia Show here! In Today's Episode You Will Learn: 1.) I would love to kick off today’s show by hearing a little about your background and the origins of LawTrades? What was the a-ha moment for you? 2.) Was Ashish nervous leaving the security of the legal profession for the life of a tech founder? What would Ashish advise people who want to make the leap but are not sure if it is worth risking everything? 3.) The legal space is about a century behind the rest of the consumerised world of tech, why is there this divergence between the advancement of tech and the lacking progression of the legal space? 4.) How did Ashish come to raise funds from 500? What was the process and interview like? Why did Ashish choose 500 out of all the accelerators? What were the challenging and surprising elements of the fundraising journey? 6.) What would Ashish do differently if he was founding LawTrades again? What does Ashish wish he had been told before he became an entrepreneur? Items Mentioned In Today's Episode: Ashish's Fave Book: Peter Thiel: Zero To One Ashish's Fave Entrepreneurial Resources: Gary Vaynerchuk, This Week In Startups, How To Start A Startup Ashish's Fave Blog: James Altucher, Tim Ferriss, As always you can follow Harry, The Twenty Minute VC, Ashish and LawTrades on Twitter here! If you would like to see a more colourful side to Harry with many a mojito session, you can follow him on Instagram here! We would like to say a special thank you to our partner for this very special 500 Startups Feature Week, LawTrades, the go to place for startups and VCs to get their legal work done. For all 20VC listeners LawTrades are offering a special $150 off your first piece of legal work when you mention ‘The Twenty Minute VC’. You can follow them on Twitter here!

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Harry Stebbings?

  This is the 20 Minute VC with your host, Harry Stebbings, and what a special episode we have in store for you today. To celebrate the third and final installment of this immense feature week of 500 startups, and owing to the fact that it is a Friday, we are bringing you the latest and greatest from 500's newest batch of world-changing companies. Joining us today is Ashish Walia, co-founder and COO at Lawtrades. Lawtrades helps startups and VCs get their legal work done through providing a really awesome marketplace of attorneys with domain expertise in the legal sector, having helped companies from the likes of YC, Techstars, and of course, 500. And Ashish is doing a test for all listeners today.

• 0:45Harry Stebbings?

  He's so confident in the speed and the effectiveness of the Lawtrades platform, that if you text a request to Lawtrades now, at the beginning of this episode, so right now, by the end, he guarantees that you will have a response to your request. So give it a try and text Lawtrades with your request, and all 20 Minute VC listeners can get $150 off their first job by quoting the 20 Minute VC. So head on over to www.lawtrades.com to give that a try and to check out the amazing work that Ashish and his team are doing at Lawtrades. But now it's time to continue with the show and meet the man of the moment. It is of course, Ashish Walia, co-founder at Lawtrades.

• 1:34Speaker 01

  You have now arrived at your destination.

• 1:36Harry Stebbings?

  Ashish, welcome to the 20 Minute VC. It's an absolute pleasure to have you on the show.

• 1:41Speaker 02

  Harry, thanks so much for having me, I really appreciate it.

• 1:43Harry Stebbings?

  Now, I'd love to kick off today's show by hearing a little about your background and the origins of Lawtrades. So can you give us that background?

• 1:51Speaker 02

  Yeah, absolutely. So um I went to undergrad in Queens, New York and um. After undergrad, I went to law school and halfway through law school, I sort of started thinking about a different career path. You know, after talking to a lot of different attorneys that I met while I was in law school. Reading a lot of entrepreneurial resources and listening to podcasts, I really started thinking more about entrepreneurship. As opposed to being a full-time lawyer and it was a great opportunity because. Halfway through law school is when we started thinking of the idea of Law Trades with my co-founder Rod. And um the whole idea behind it was to sort of decentralize the major corporate law firms because.

• 2:32Speaker 02

  You know, inevitably, when a entrepreneur is faced with some sort of legal issue, whether they want to start their company or. You know, just get some basic legal work done, uh there are two options. Before we existed were to either go to a bottom-of-the-barrel, do-it-yourself legal service. Which ends up costing a lot more money down the road to fix all the mistakes. Or you're stucking almost six hundred dollars an hour for some high-level law firm um for routine legal work and. That's where we really thought there was a huge opportunity because there's so many. Um boutique law firms and solo-practicing attorneys that left those big law firms. Um without the high overhead that are looking for more work and. We found that as a great opportunity to sort of connect entrepreneurs to them and.

• 3:14Speaker 02

  Um it's been going well. We're saving a lot of people money and making the process much more affordable and also. Generating a stream of income for attorneys. So, yeah, that was uh that really set it off for us.

• 3:25Harry Stebbings?

  And then having kind of spent time in the legal industry in terms of studying, you had the option of pursuing that legal profession. And let's be honest, there's a lot of security and a good salary. Uh so were you nervous to to lose that by taking the leap into the startup world by being founder or co-founder of Law Trades?

• 3:44Speaker 02

  Yeah, so that's a great question. Um, during law school, I was, you know, sort of in the top of my class. I studied with, um, you know, good people that ended up getting those high level six-figure jobs right out of law school. So it was extremely nerve-wracking to, um, sort of forego the law school route or the, the lawyer route and to jump into a startup. And the reason why I did it is because, um, you know, I really looked at what the next like five years of my life would probably look like if I became a lawyer and, um, it wasn't really appealing to me at all. And I'm sure you heard, uh, Peter Thiel say himself, it's like when you, join a law firm, it's something that, uh, everyone on the outside wants to get into it, but everyone on the inside of that law firm wants to leave.

• 4:28Harry Stebbings?

  Is dying to get out, yeah.

• 4:30Speaker 02

  Yeah, exactly. And, and I've heard that from so many people that I really looked up to and I thought that, you know, if I already know this now, um, why not just pursue entrepreneurship? It was something that was, um, always in the back of my mind and I didn't really have the right, I didn't know what problem I wanted to solve or anything like that. And then all of this sort of came right onto my lap and I thought that this was, you know, the perfect opportunity to go forward. So, um, it, it, it was cer- certainly nerve-wracking, but rewarding at the same time. And, um, yeah.

• 4:59Harry Stebbings?

  And what would you advise people then, thinking of maybe making the same leap, uh, and joining the world of entrepreneurship over a more stable career? Is there anything they should be considering or think about?

• 5:09Speaker 02

  Right. So i- it, it's sort of what you hit on before. It's you're gonna forego a comfortable salary, you're gonna forego, nice dinners all the time and, uh, you know, benefits, all this, this stuff that comes with having a full-time career. And inevitably, I don't think that this is for e- everyone, you know what I mean? I think that there, it's such a risky, it's such a risky path. There's so many ups and downs daily, so many stresses, et cetera. Um, so I think that you really just have to examine what you want out of your life, you know? Me, um, regardless of whether or not Lawtrade ends up being a powerhouse company, you know, five or six years down the road, um, I think that the path of, you know, figuring it out myself and really working my tail off and hustling, you know, like that's what I really wanna do.

• 5:53Speaker 02

  Um, so, you know, figure out what it is that you wanna do and, and just go for it. And, you know, the rest will sort of, you know, pave your own path around it.

• 6:00Harry Stebbings?

  And when did you start the Lawtrade's journey then?

• 6:03Speaker 02

  Yeah, so the idea came about halfway through being in law school. And you know, it's like right around my, uh, towards the end of my first, uh, first semester of my second year of law school. And, um, you know, Rod approached me and said, hey, you know, let's build this out. We could definitely make a really good platform for, um, businesses and lawyers. And the first version that we built out was absolutely horrendous. Um, we had, we had zero traction. It was simply a lawyer directory service. Um, no one was really using it. So around that time, like while I was in law school, it was sort of a blessing for me because, um, you know, I was living on student loans while I was figuring out everything. Um, and you know, it, it helped us really get the product right. So I graduated law school about, uh, four months ago.

• 6:47Speaker 02

  Yeah, four months ago in May.

• 6:49Harry Stebbings?

  Thank you, congratulations.

• 6:50Speaker 02

  Thank you, thank you. And by, by the time I graduated, you know, we had already raised a small seed round. Um, we had some traction and then, you know, lo and behold, now we're in an accelerator. So everything has been very, uh, it, it's just been a wild ride the last, you know, two years or so.

• 7:07Harry Stebbings?

  And how do you think then you've changed as a COO and startup employee slash co-founder in the time that you started? Have you evolved a lot as a person and as an individual? You said about the journey there personally for you.

• 7:21Speaker 02

  Yeah, absolutely. I think that there's, um, you know, when you're running a company and, and just trying to, you know, be that unicorn, be that company that really sets things off. There's so many days where, you know, you're gonna face a lot of stress. You're gonna face a lot of ups and downs and a lot of times your normal friends that have comfortable jobs can't really relate to it. Right? So, um, a lot, you know, they can't, they don't really get it, you know? And, and so there, there were certainly a lot of times of like self-reflection, um, and, and just really, you know, being alone and really thinking about, um, how I was gonna build things and, and whatnot. So, um, fortunately for us, um, and, and every other person thinking of pursuing entrepreneurship,

• 8:01Speaker 02

  the amount of resources that are out there to sort of guide you through the path and, and learn more about it and how to get through the hard times and how to grow your business, like all these resources are right there for us. And I really took that upon myself to, um, you know, pay as much attention as I could and learn from other people that were sharing such valuable knowledge, whether it was in a podcast, a blog post, a book. And I was really all about it and, uh, that really helped me out a lot.

• 8:27Harry Stebbings?

  This one isn't in the schedule, by the way, just to let you, all the listeners, but I'm too intrigued now. You said about your favorite entrepreneurial resources. I am a bit of a slut for entrepreneurial resources too. So, what would you say is the most formative entrepreneurial resource or the one that you'd most recommend?

• 8:47Speaker 02

  Oh, so tough. That's such a hard question.

• 8:49Harry Stebbings?

  What other than the twenty minute VC, obviously.

• 8:55Speaker 02

  So, for me, the person that I really started resonating with, um, halfway through law school was Gary Vaynerchuk, you know.

• 9:02Harry Stebbings?

  Amazing.

• 9:03Speaker 02

  Yeah, I, I really just resonated with his message, um, because what I tried to learn. When I was learning about entrepreneurship, because I realized I'm not a product guy, I'm not gonna code out the best website. But what I could do is, I'm really good at sales, you know, I could, I could make customers feel great, I could. Make our attorneys feel excellent and, and deliver them a great service. So I really tried to find entrepreneurs. That had that sort of background. So, you know, I've read, I watched the Ask Gary V show, I read all of his books. I also read a lot of, um, uh, you know, uh, blog posts by like Jason Calacanis, I watched This Week in Startups. Around the time where I really got started, uh, ironically, how to start a startup at, uh.

• 9:45Speaker 02

  Stanford was, you know, just really getting, uh, out there, which was the perfect timing for me because literally, it, it's just. You learn from these resources and it's like better get, it's, it's better to learn from these resources than it is to just go out and pay, you know, a hundred grand for an MBA. So much of it for free and it's so much more practical. So, a lot of, um, everything I learned so far has really been because I. You know, on my commute, I'm listening to, um, you know, the Ask Gary V show, I'm listening to Tim Ferriss interview someone like Brian Johnson and figure out how. You know, non-technical founders were able to grow massively successful businesses and, um, I loved it.

• 10:22Harry Stebbings?

  Yeah. And then let's move back to law trades now and obviously absolutely fascinating company in. Uh, a sector that is, it's really rather archaic in its structure. So.

• 10:34Speaker 02

  Absolutely.

• 10:35Harry Stebbings?

  Why, why do you think there is this divergence between the advancement of tech? And then the complete lack of progression, obviously other than law trades in, in the legal space?

• 10:46Speaker 02

  So there's, there's, I, I think it really stems from two core issues and it's insanely, like you said, it's very archaic. And you're learning essentially the same cases, uh, the same statutes that, uh, you know, attorneys or law school students learned, you know, ten to twenty years ago. Um, inherently, law school does not teach you to be entrepreneurial at all. You know, it's, it's looked down upon to, you know, come out of law school and, um, be an apprentice with an attorney and get an attorney mentor and practice by yourself. You know, you're encouraged to go out and find a job and work under a partner and be an associate. So I think that, you know, most of the, most of, most people in law school end up going that route. They end up, you know, finding a job and working under someone. And, you know, when you sort of do that for a couple of years,

• 11:29Speaker 02

  I think it really negates, um, becoming entrepreneurial. So I, I, I, you know, hopefully, um, I think that law schools now are sort of catching on to, you know, integrating more legal technology into, um, you know, the profession. And there's certainly, like, my law school was, um, you know, they're, they're starting like incubators for attorneys that wanna become solo practicing attorneys right out of law school, which is, you know, something that should have been done ten, ten, fifteen years ago. So, um, you know, it's funny, it, I, to show you how archaic it is, um, I had a property class, which is, you know, a mandatory class in law school. And I would, you would literally get penalized if you were to bring your laptop into class. So you couldn't even take notes on a laptop.

• 12:12Speaker 02

  They literally wanted you to, uh, sit down and write all your notes out. And in my mind, I'm thinking, for crying out loud, it's two thousand, at that time, it's two thousand fourteen. You tell me I can't bring a laptop to class?

• 12:21Harry Stebbings?

  In terms of then the lawyers that you provide on your platform, are most of them solo practitioners? Are they kind of large corporates who are looking to do extra hours?

• 12:31Speaker 02

  Right. So we have pretty thick, strict standards for the lawyers that, uh, come onto our platform. So generally, what we look for is attorneys that have big law experience, um, that, you know, are sort of tired of like the work-life balance. And inevitably, a lot of people will work in big law and leave after, you know, three or four years, um, to start their own firm. Because, you know, you have a family, um, you sort of wanna not work a hundred hours a week and, and sort of, you know, operate your own way. So those are the attorneys we go after, you know, essentially a lot of small boutique firms and a lot of solo practitioners. And, you know, they have a lot of flexibility. They could, uh, essentially work from a beach and get clients on law trades, you know, and make a living. So it's great.

• 13:15Harry Stebbings?

  In term then in terms of you mentioned earlier that you'd raised the seed fat, the seed round. So jumping a few stages here and moving to the funding side of Law Trades. You've raised investment from our dear friends and of course it is five hundred feature week, so you've raised it uh investment from five hundred. So how did that come about?

• 13:34Speaker 02

  Great question. So um as you know, as a guest of my podcast, um I started a podcast to drive traffic to. My my website Law Trades and one of the guests I had on my podcast was a good friend of mine, his name is Rob Cucci. And he has a company called Pigeon, um where they sell, you know, care packages to college students. And he actually went through five hundred. Um so it just so happened that, you know, I told him about our business and like. We've always been very revenue focused since day one, um. And, you know, told him about our numbers and whatnot. And he was like, hey, you know, you should apply to five hundred. The deadline's gonna come up in literally about a week or two. And um you know, it was sort of out on the whim. We ended up applying um a couple of days before the deadline.

• 14:15Speaker 02

  The next day we got an interview from Brian Wang, who just happened to be in New York City that day. And told us to come into an interview, have, so we have the interview. The next day later, we have another interview um via Skype with Elizabeth Yin. Um she loved what we were doing, the the the traction we had so far. And then uh she invited us in and then literally. Four days after that, we picked up everything from New York and just moved to California. So it was a wild ride the last couple of weeks.

• 14:45Harry Stebbings?

  And then what was the interview questioning and process like? What what are they looking at? Are they looking for the very much, why see the? Deep analysis of the market and just your thoughts on it, or do they really hone in on the business itself?

• 14:57Speaker 02

  Right. So I mean, for us in particular, like I don't know if they do this for every company. For us, what they seem to really care about that I think helped us get in was. You know, one, we had um about two or three people recommend us after they learned about their business. So. Um what I did was I found, you know, I literally would just, was, once I had one recommendation. Um I tried to get connected to other uh five hundred mentors or founders, you know, Stelly F D. Um I'm sure you know Stelly. He's a mentor at five hundred. He was also on my podcast. He knew what we were doing. And I said, hey, you know, here's here's my numbers. Here's the business. Let me talk to you about it. And if you think if it's a good fit for five hundred, you know, I'd really appreciate a recommendation. So I did that with a few other people.

• 15:40Speaker 02

  And I think that combined with our traction and and our unit economics behind the business was enough for them to give us a shot. So I I would really say for anyone that wants to get in, I, you know, focus on just getting some early validation and show that there is some opportunity with your business. And then also try to just get connected with people within the network, because if they vouch for you, I think five hundred is invested in over like a thousand companies.

• 16:07Harry Stebbings?

  Twelve hundred, apparently.

• 16:08Speaker 02

  Twelve hundred.

• 16:08Harry Stebbings?

  According to Marvin from Wednesday, twelve hundred.

• 16:11Speaker 02

  Yeah, right. And I'm sure that a lot of those companies come from recommendations from existing founders. So, you know, definitely, definitely try to get your foot in the door with them.

• 16:20Harry Stebbings?

  And why did you choose five hundred? And obviously, they're fantastic. But for you personally, why did you choose five hundred out of the plethora now of accelerators that exist in the US system?

• 16:30Speaker 02

  Yeah, so five hundred, we really wanted to go to five hundred is because they're so focused on distribution. And I think that that was, you know, the one thing we really wanted to nail was, you know, how can we get more distribution? What kind of experiments could we run to even get more customers? And I think that, you know, we're, obviously, we're product focused, but I think it seems like Y C tends to have more product focused engineers, you know, that they're looking for. And five hundred, you know, there's a, there's an interesting thing that I'd love for you to link up to is there's a core question where Dave McClure really writes about the cultures that, you know, tech stars, Y C and five hundred all have.

• 17:13Speaker 02

  And if you look at it, it's funny. It's like five hundred founders tend to be geeky hustlers. They tend to be very social, community driven, etc. And like, I looked at that and I was like, that is literally us. And I I just think the overall message and culture really resonates with what we want to do.

• 17:29Harry Stebbings?

  And then, sorry, the link for that core article will be in the show notes and the iTunes description, just for anyone who wants to read it like I do now.

• 17:37Speaker 02

  Yeah.

• 17:38Harry Stebbings?

  But but again, and then in terms of the fundraising process, what was the surprising or challenging elements for you? You said, obviously, you'd raised the seed round before five hundred. And then looking at the five hundred experience too, what were the surprising and challenging elements for you?

• 17:54Speaker 02

  Um, you know, the most challenging thing I think is just sort of uh finding those people that understand your vision, right? Like, so we raised the seed round initially, it was like a very small pre-seed round when we had zero traction. Um, you know, these were just a bunch of angels, a small micro VC that came in on the round. So obviously that was very challenging because we didn't have much to show for other than a vision. So that was our big challenge um at first. And then through five hundred, you know, the big, the biggest challenge for five hundred was literally just picking up everything in three days and leaving. You know, and just sort of putting everything on the back burner for a while and moving to California for the next four months. That was sort of, that caught me by surprise, you know, I wasn't expecting us to even get in at that point.

• 18:38Harry Stebbings?

  It's quite a, it's quite a big move to be a fash, don't worry, you wanna loan it in.

• 18:43Harry Stebbings?

  Yeah, uprooting your life, but I, anyone would uproot their life for five hundred, to be.

• 18:47Speaker 02

  Oh, absolutely, absolutely. And, um, you know, I think the challenge at the end of the day, it's not so much about the raise. It's more or less about building a good business, you know, Gary Vaynerchuk told me when I, I went on his show, the Ask Gary V show, I think it was, you know, one of the early episodes to ask him a question. And he said, you know, all you should focus on right now is just not even worry about raising money. Just focus on making a really good business and everything else will come. And that's sort of like the, that's sort of what I tell myself every time. So, um, I, I would really just stick to that message and then that's how it happened, you know, we really put our heads down to build out Law Trades. Um, in those four months after I graduated law school and even while I was in law school and then lo and behold,

• 19:29Speaker 02

  you know, we, we had the introduction to five hundred and then, you know, here we are today.

• 19:34Harry Stebbings?

  And if it's okay with you now, we're gonna move into a quickfire round.

• 19:37Speaker 02

  Yeah, absolutely.

• 19:39Harry Stebbings?

  So your favorite book and why?

• 19:41Speaker 02

  So the, the, it's definitely Zero to One by Peter Thiel. I read that during law school. That's really what changed my whole outlook.

• 19:48Harry Stebbings?

  Yeah.

• 19:49Speaker 02

  Uh, being, becoming a lawyer and just doing something much bigger. So definitely Zero to One.

• 19:54Harry Stebbings?

  Which founder do you most look to emulate?

• 19:57Speaker 02

  Um, that's a tough one. I would definitely say Brian Johnson, the founder of Braintree.

• 20:03Harry Stebbings?

  Yeah.

• 20:04Speaker 02

  But you know, just being a single founder with no technical background, building a massive company that customers love. That was very tech focused and and then, you know, later doing what he's doing now. It's it's it's a fascinating story.

• 20:17Harry Stebbings?

  And actually, Ashish was kind enough to introduce us to Brian and we have actually recorded an amazing show with Brian.

• 20:22Speaker 02

  I can't wait to.

• 20:23Harry Stebbings?

  That is coming out soon, but Ashish, thank you again so much for that one.

• 20:26Speaker 02

  No problem.

• 20:27Harry Stebbings?

  And then what's your most read blog or newsletter?

• 20:30Speaker 02

  Oh, I definitely, my favorite thing to read is definitely James Altucher's blog.

• 20:35Harry Stebbings?

  Oh, brilliant.

• 20:37Speaker 02

  He's so self-deprecating that, you know, on the worst day, you know, you could have a terrible day, you read his blog and you will just feel totally fine. So I love hearing his stories.

• 20:48Harry Stebbings?

  And then what are your must-have apps or software?

• 20:52Speaker 02

  Um, so I use, uh, I'm sure everyone tells you Slack, you know, Slack is what we really use a lot. Um, I really use, I read a lot on Medium, I'm I'm really big on Quora. Um, so you know, those three apps are definitely, um, what I use a lot, aside from like Twitter, you know.

• 21:11Harry Stebbings?

  What's the best thing about being a founder and not a lawyer?

• 21:15Speaker 02

  The best thing about being a founder is that you have your own opportunity to create your own path. Whereas, you know, being in the, being a lawyer, you really don't, you know, you come out of law school, you have to sort of work for someone else. Get accustomed to working as an associate and then, you know, sort of hope that one day you can make partner. Um, or, you know, inevitably start your own firm where you start the whole cycle over again. I very much enjoy the unpredict, the unpredictability of entrepreneurship and the the total grind that it encompasses. So that that, you know, that's the best part about it. I love it.

• 21:50Harry Stebbings?

  And then we've spoken a lot about how, uh, Law Trades was formed. What are the next five years for you and Law Trades hold?

• 22:00Speaker 02

  The the biggest thing that I hope to accomplish with this is to sort of be the biggest virtual law firm that decentralizes the existing model and creates the most affordable, um, scalable and efficient solution for people that are looking to handle their legal work. And um, you know, we're we're s- we're getting there and it's going to be interesting to see how the next couple of years fold out.

• 22:23Harry Stebbings?

  Well, Ashish, thank you so much for coming on the show today. It's been absolutely fantastic to have you join us and I'm so pleased that we could hear the Lawtrades journey.

• 22:32Speaker 02

  I really appreciate it. Thanks so much for having me on.

• 22:35Harry Stebbings?

  And again, a huge thank you to Ashish for sharing his amazing journey with Lawtrades on the show today. And have you received the text from Lawtrades in response to your request? Yep, pretty amazing. And that's Lawtrades for you, replying five to 10 minutes to all requests. Absolutely phenomenal service and a must use for all startups and VCs looking to get their legal work done in an affordable way. Uh, and as always, thank you so much for your continued support in listening to today's episode. And I'd like to say a special thank you again to Ashish for joining us. And I look so forward to seeing you all in the next episode of the 20 Minute VC. Thank you so much.