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Oct 30, 2015 · 23m · 20vc

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

Ashish Walia · 15m spoken Harry Stebbings · 5m spoken
0:00 / 0:00

gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions

In this episode of The 20 Minute VC, host Harry Stebbings interviews Ashish Walia, co-founder and COO of LawTrades, about disrupting the traditional legal sector with an on-demand attorney marketplace. Walia discusses transitioning from law school to startup leadership, navigating the 500 Startups accelerator, and scaling a virtual law firm.

How this conversation actually went

Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Harry holds 25.9% of the talking time here. How this is scored →

Harry as informed peer 2.8 Guest teaching 4.2 Guest disagreement 1.0 Harry pushing back 1.4
05100:0010:0020:001:29–6:00 · Harry as informed peer 3/10 Ashish's Background and the Founding of LawTrades Harry guides the conversation smoothly and quotes Peter Thiel regarding the law firm dynamic. Ashish explains the structural problems with high-fee corporate firms versus do-it-yourself legal platforms.6:00–10:22 · Harry as informed peer 3/10 LawTrades Early Traction and Growth Journey Harry departs from his script to ask Ashish about his favorite entrepreneurial resources. Ashish educates listeners on Gary Vaynerchuk, Stanford's How to Start a Startup, and other media.10:22–13:15 · Harry as informed peer 2/10 The Archaic Legal Industry and Lawyer Marketplace Harry asks why the legal industry remains so archaic. Ashish details how traditional legal education suppresses entrepreneurial mindsets and shares a anecdote about laptops being banned in class.13:16–19:33 · Harry as informed peer 4/10 Getting into 500 Startups and Fundraising Lessons Ashish shares LawTrades' experience applying to and joining 500 Startups. Harry gently interjects to correct the total number of 500 Startups investments to 1,200 based on a prior interview.19:34–21:50 · Harry as informed peer 2/10 Quickfire Round with Ashish Walia A quickfire round covering favorite books, apps, and founder inspirations. Harry acknowledges Ashish for introducing him to Braintree founder Brian Johnson for an upcoming interview.1:29–6:00 · Guest teaching 4/10 Ashish's Background and the Founding of LawTrades Harry guides the conversation smoothly and quotes Peter Thiel regarding the law firm dynamic. Ashish explains the structural problems with high-fee corporate firms versus do-it-yourself legal platforms.6:00–10:22 · Guest teaching 4/10 LawTrades Early Traction and Growth Journey Harry departs from his script to ask Ashish about his favorite entrepreneurial resources. Ashish educates listeners on Gary Vaynerchuk, Stanford's How to Start a Startup, and other media.10:22–13:15 · Guest teaching 5/10 The Archaic Legal Industry and Lawyer Marketplace Harry asks why the legal industry remains so archaic. Ashish details how traditional legal education suppresses entrepreneurial mindsets and shares a anecdote about laptops being banned in class.13:16–19:33 · Guest teaching 5/10 Getting into 500 Startups and Fundraising Lessons Ashish shares LawTrades' experience applying to and joining 500 Startups. Harry gently interjects to correct the total number of 500 Startups investments to 1,200 based on a prior interview.19:34–21:50 · Guest teaching 3/10 Quickfire Round with Ashish Walia A quickfire round covering favorite books, apps, and founder inspirations. Harry acknowledges Ashish for introducing him to Braintree founder Brian Johnson for an upcoming interview.1:29–6:00 · Guest disagreement 1/10 Ashish's Background and the Founding of LawTrades Harry guides the conversation smoothly and quotes Peter Thiel regarding the law firm dynamic. Ashish explains the structural problems with high-fee corporate firms versus do-it-yourself legal platforms.6:00–10:22 · Guest disagreement 1/10 LawTrades Early Traction and Growth Journey Harry departs from his script to ask Ashish about his favorite entrepreneurial resources. Ashish educates listeners on Gary Vaynerchuk, Stanford's How to Start a Startup, and other media.10:22–13:15 · Guest disagreement 1/10 The Archaic Legal Industry and Lawyer Marketplace Harry asks why the legal industry remains so archaic. Ashish details how traditional legal education suppresses entrepreneurial mindsets and shares a anecdote about laptops being banned in class.13:16–19:33 · Guest disagreement 1/10 Getting into 500 Startups and Fundraising Lessons Ashish shares LawTrades' experience applying to and joining 500 Startups. Harry gently interjects to correct the total number of 500 Startups investments to 1,200 based on a prior interview.19:34–21:50 · Guest disagreement 1/10 Quickfire Round with Ashish Walia A quickfire round covering favorite books, apps, and founder inspirations. Harry acknowledges Ashish for introducing him to Braintree founder Brian Johnson for an upcoming interview.1:29–6:00 · Harry pushing back 1/10 Ashish's Background and the Founding of LawTrades Harry guides the conversation smoothly and quotes Peter Thiel regarding the law firm dynamic. Ashish explains the structural problems with high-fee corporate firms versus do-it-yourself legal platforms.6:00–10:22 · Harry pushing back 2/10 LawTrades Early Traction and Growth Journey Harry departs from his script to ask Ashish about his favorite entrepreneurial resources. Ashish educates listeners on Gary Vaynerchuk, Stanford's How to Start a Startup, and other media.10:22–13:15 · Harry pushing back 1/10 The Archaic Legal Industry and Lawyer Marketplace Harry asks why the legal industry remains so archaic. Ashish details how traditional legal education suppresses entrepreneurial mindsets and shares a anecdote about laptops being banned in class.13:16–19:33 · Harry pushing back 2/10 Getting into 500 Startups and Fundraising Lessons Ashish shares LawTrades' experience applying to and joining 500 Startups. Harry gently interjects to correct the total number of 500 Startups investments to 1,200 based on a prior interview.19:34–21:50 · Harry pushing back 1/10 Quickfire Round with Ashish Walia A quickfire round covering favorite books, apps, and founder inspirations. Harry acknowledges Ashish for introducing him to Braintree founder Brian Johnson for an upcoming interview.

speaking balance: gold is Harry, purple is the guest (3 minute bins)

0:00 · Harry 56.2% · guest 43.8%0:00 · Harry 56.2% · guest 43.8%3:00 · Harry 16% · guest 84%3:00 · Harry 16% · guest 84%6:00 · Harry 22.3% · guest 77.7%6:00 · Harry 22.3% · guest 77.7%9:00 · Harry 13.1% · guest 86.9%9:00 · Harry 13.1% · guest 86.9%12:00 · Harry 21.8% · guest 78.2%12:00 · Harry 21.8% · guest 78.2%15:00 · Harry 21.5% · guest 78.5%15:00 · Harry 21.5% · guest 78.5%18:00 · Harry 17.1% · guest 82.9%18:00 · Harry 17.1% · guest 82.9%21:00 · Harry 44.3% · guest 55.7%21:00 · Harry 44.3% · guest 55.7%
Sharpest disagreement ▶ 11:55 Frustration with legal education archaic rules

Ashish passionately criticizes the antiquated legal education system, calling out the ridiculousness of getting penalized for bringing a laptop to class in 2014.

 Hardest push from Harry ▶ 16:05 Harry corrects the 500 Startups portfolio stat

When Ashish mentions 500 Startups has invested in over a thousand companies, Harry politely interrupts to specify the exact figure of 1,200 from a recent interview.

 Biggest teaching moment ▶ 11:00 Explaining why law school negates entrepreneurship

Ashish breaks down for Harry how law schools actively discourage entrepreneurial risk and socialize graduates to work as associates under law firm partners.

 Harry holds his own ▶ 16:00 Harry cites Marvin's portfolio data point

Harry demonstrates deep knowledge of 500 Startups by citing factual data from his earlier conversation with Marvin that week.
the scores for every segment, with the reasoning behind each
ChapterTopicHarry as informed peerGuest teachingGuest disagreementHarry pushing backWhy
Ashish's Background and the Founding of LawTrades 3411 Harry guides the conversation smoothly and quotes Peter Thiel regarding the law firm dynamic. Ashish explains the structural problems with high-fee corporate firms versus do-it-yourself legal platforms.
LawTrades Early Traction and Growth Journey 3412 Harry departs from his script to ask Ashish about his favorite entrepreneurial resources. Ashish educates listeners on Gary Vaynerchuk, Stanford's How to Start a Startup, and other media.
The Archaic Legal Industry and Lawyer Marketplace 2511 Harry asks why the legal industry remains so archaic. Ashish details how traditional legal education suppresses entrepreneurial mindsets and shares a anecdote about laptops being banned in class.
Getting into 500 Startups and Fundraising Lessons 4512 Ashish shares LawTrades' experience applying to and joining 500 Startups. Harry gently interjects to correct the total number of 500 Startups investments to 1,200 based on a prior interview.
Quickfire Round with Ashish Walia 2311 A quickfire round covering favorite books, apps, and founder inspirations. Harry acknowledges Ashish for introducing him to Braintree founder Brian Johnson for an upcoming interview.

Statements from this episode (11)

Assertion Not checkable as stated
DIY legal services cost founders more long-term due to mistakes
“Do it yourself legal service, which ends up costing a lot more money down the road to fix all the mistakes”
Ashish Walia Oct 30, 2015 ▶ 2:30
Assertion Partly supported
High-level corporate law firms charge $600 an hour for routine work
“You're stuck paying almost 600 dollars an hour for some high level law firm for routine legal work”
Ashish Walia Oct 30, 2015 ▶ 2:30
Insight
Everyone inside a traditional law firm wants to leave
“When you Join a law firm. It's something that everyone on the outside wants to get into it, but everyone on the inside of that law firm wants to leave.”
Ashish Walia Oct 30, 2015 ▶ 4:16
Assertion Not checkable as stated
LawTrades' initial product was a lawyer directory with zero traction
“And the first version that we built out was absolutely horrendous. We had zero traction. It was simply a lawyer directory service. No one was really using it.”
Ashish Walia Oct 30, 2015 ▶ 6:22
Insight
Free online startup resources are more valuable than a $100,000 MBA
“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.”
Ashish Walia Oct 30, 2015 ▶ 9:42
Opinion
Law school inherently fails to teach students how to be entrepreneurial
“Inherently, law school does not teach you to be entrepreneurial at all.”
Ashish Walia Oct 30, 2015 ▶ 11:03
Disclosure
LawTrades targets former Big Law attorneys running solo or boutique practices
“So we have pretty strict standards for the lawyers that come onto our platform. So generally what we look for is attorneys that have big law experience that, you know, are sort of tired of like the work-life balance. And inevitably a lot of people will work in…”
Ashish Walia Oct 30, 2015 ▶ 12:32
Insight
500 Startups selection hinges on early validation and network recommendations
“So 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 v…”
Ashish Walia Oct 30, 2015 ▶ 15:49
Opinion
Y Combinator seeks product engineers while 500 Startups prefers community hustlers
“I think it seems like YC tends to have more product focused engineers, you know, that they're looking for, and 500, you know, 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 th…”
Ashish Walia Oct 30, 2015 ▶ 16:48
Assertion Supported
Bryan Johnson built Braintree as a non-technical solo founder
“I would definitely say Brian Johnson, the founder of Braintree. 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 then, you know, later doing what he's doing…”
Ashish Walia Oct 30, 2015 ▶ 20:00
Prediction Not checkable as stated
LawTrades aims to become the world's largest virtual law firm
“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 scalable and efficient solution for people that are looking to handle their legal work.”
Ashish Walia Oct 30, 2015 ▶ 22:00
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