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The If Then Podcast
"The way you earn the trust of the Product people . . . You have to learn the shit out of the product. You have to learn their jobs inside and out." - Shahab Asghar, on the If Then Podcast.
We’re back with another installment of IF:Then, the hottest newsletter podcast about strategy at the intersection of law and technology. To stay up to date with interviews and news recaps on career intentionality and product strategy, hit that subscribe below.

Welcome back everyone! Where’ve you been!? Ok fine. You may have noticed (hopefully you noticed) that If Then took a few months off the content-creation grind, and its probably left a meme-shaped hole in your heart. But just because the takes haven’t been flying to your inbox doesn’t mean that IF:Then has stopped thinking intently about legal careers, a growth mindset, and product and regulatory strategy.
That’s why we’re pivoting to podcasts.
Written internet content is tough business when you’re fully absorbed in a startup, but I’m happy to practice what I preach and turn the obstacle into an opportunity. Thankfully, the If Then Community has a deep bench of Legal Wayfinders applying a strategic mindset not only to the products and projects they work on, but to their own careers as attorneys shaping technology. It’s time to learn more about them and what they do.
Ultimately, every If Then Podcast should cover two high level topics:
Product Strategy - using legal skills and regulatory acumen to build a product, create the best user experience, grow a business, and add the most value to company. This goes for and applies to anyone in legal, policy, or simply building in a regulated space.
Career Intentionality - like many professions, a legal career can be navigated or it can navigate you. IF:Then is particularly interested in the choices Legal Wayfinders made along the way to do interesting work they are interested in, and actively seek to be their best professional selves.
Beyond that, we will always try to have a good time and have a conversation that is both entertaining and informative. Personally, one of my favorite things about writing the newsletter was how much I myself learned about the topic from doing research, refining ideas, and distilling thoughts onto the internet. I’m equally excited to chat with attorneys and builders, learn how really smart people have navigated their own journeys, and dig in to the topics that have interested them enough to make careers out of.
The Innovation Game
Behind every code . . . is a developer. But somewhere nearby that developer, hopefully, is a really good attorney.

As with all things IF:Then, the focus here is on community. That is why this week’s guest on the podcast is my good friend Shahab Asghar. When it comes career intentionality, Shahab has consistently been an early adopter. Shahab did something very unique early in his career - he took time off to reflect on his experiences along the typical BigLaw path in order to figure out exactly how to align his work and his interests. Not his hobbies, but work that made him eager and willing to continuously learn.
The way you earn the trust of the Product people . . . You have to learn the shit out of the product. You have to learn their jobs inside and out.
The Innovation Game charts Shahab’s path to joining Coinbase as their third lawyer in early 2015, and carving out a practice in privacy and security law years before Equifax, Cambridge Analytica, the general existence of Mark Zuckerberg, and GDPR brought those conversations to the forefront and made “Privacy Counsel” a huge market.
Shahab walks us through how, in his over six years at Coinbase, he learned to work collaboratively with product and engineering teams as a thought partner rather than as a check and/or balance, and his pitch on how to make Privacy a competitive advantage for the company.
We also touch on the inherent tension in blockchain/crypto between privacy (particularly anonymity and pseudonymity) and transparency (an immutable public ledger), and how that informs as we think about digital identity and how we interact with institutions and each other over the internet going forward. We don’t even mention the word metaverse, because if you say metaverse three times, a creepy VR avatar of Zuckerberg tries to get you to play Wordle with him or something, but I’ll just write it here. Metaverse!
Lastly, he takes us through his new role with Scale LLP, a sort of “decentralized law firm” that aims to reduce the costs of top-tier legal services by building an elite community attorneys with an entrepreneurial spirit. Scale attorneys are able to pool and share resources allowing them to give high-quality advice to clients while maintaining a lifestyle with a different incentive structure than the standard law firm affords.
Bonus Content!
We’ll try to put out one of these a week, and if I’m feeling spicy will find a way to put out an additional more news / current event oriented episode from time to time as well. I would love any feedback on the podcast or anything else - hopefully every episode going forward will be simultaneously the best one yet, and the worst it will ever be from that point forward.
As a bonus: below is the very first episode recorded with my good friend Ryan Taggett, building technology products at PricewaterhouseCoopers. Ryan takes us through what it’s like to be a technology company at a Big Four accounting firm, gives us some details on PwC’s role in that whole Moonlight/LaLa Land screwup, and pitches us an updated version of Tom Cruise’s The Firm.
Make sure you subscribe on Apple Podcasts or Spotify, give us a 5-star review, smash that like button (ok that one doesn’t apply), you know the drill. Hurry, before I pivot this into a TikTok. But most of all, do work that is interesting and that you are interested in. You have the skills to take control. And if you need some strategic help, a sounding board, or just generally a community, IF:Then is here to help.
Until next time, friends - David Ikenna Adams
Twitter | LinkedIn | Email | ifthen.vc
If you liked this content and want to see more, please subscribe. If you’d like to join the IF:Then community, please reach out to me david@ifthen.vc