ILG On-Demand: Privacy & Ad Law in the Trenches

Rob Chesnut helped prosecute CIA spy Aldrich Ames, then became the "sheriff of the internet" at eBay. Rob Chesnut explains how to catch bad actors at scale and why trust may be the most valuable thing a platform has.

In this episode, Jamie and Robert discuss:

• Fraud, counterfeits, and trust on eBay's global marketplace
• Proactive trademark enforcement and the Tiffany case
• Online dispute resolution and data-driven fraud detection at scale
• Trust, speed, and self-regulation in the AI era
• Navigating regulators and why everyone in a company should own ethics

"Do it yourself, demonstrate goodwill, demonstrate that you want to be a good player. That wards off unreasonable regulation, and I think it also helps build trust.” - Robert Chesnut

About Robert Chesnut: Rob Chesnut is the former General Counsel and Chief Ethics Officer at Airbnb, where he grew the legal team globally and led efforts on regulatory and trust matters. A Harvard Law and University of Virginia graduate, Rob previously spent 14 years with the U.S. Justice Department before joining eBay as its third attorney and founding its Trust and Safety department, where his team significantly reduced fraud and counterfeiting. He later served as General Counsel at Chegg and has spent over two decades advising internet companies on ethics, trust, and safety. Rob is also the bestselling author of Intentional Integrity: How Smart Companies Can Lead an Ethical Revolution, published in 2020 and named one of Inc. Magazine’s top 10 business books of the year.

Connect with Robert Chesnut:

LinkedIn - https://www.linkedin.com/in/robchesnut/ 

Book: Intentional Integrity - https://www.intentionalintegrity.com/ 

Connect with Jamie Rubin and ILG:

Host - https://www.infolawgroup.com/jamie-rubin 

Website - https://www.infolawgroup.com/

LinkedIn - https://www.linkedin.com/company/infolawgroup-llp/

Email - [email protected]

What does it take for marketers to actually trust their lawyers? In this episode, you’ll hear how in‑house marketing legal builds credibility, gets “in the room” early, and still lets campaigns stay bold and exciting. 

Jamie Rubin talks with PayPal’s Senior Counsel, Andra Dallas, about guiding high-impact marketing in a complex, global business. They explore music licensing and rights splits, creative promotions (including a cash-stuffed pizza stunt), prize fulfillment and risk checks, and the challenge of coordinating across multiple stakeholders. Andra also explains why deep product knowledge is essential for marketing lawyers, reflects on her nontraditional career path, from conferences to CARU to L’Oréal and financial services, and shares why she still genuinely loves the work and the community around it.

In this episode, Jamie and Andra discuss:

• Building trust between marketing and legal
• Getting “hands dirty” and involved early in campaigns
• Music licensing, copyright splits, and usage rights
• Creative promotions, prize fulfillment, and risk mitigation
• Life and career path as an in‑house marketing counsel in a global company

"You can push the envelope, but you can't rip open the envelope.” - Andra Dallas

Connect with Andra Dallas:

LinkedIn -  https://www.linkedin.com/in/andra-dallas-18ab2b11/ 

Email - [email protected] 

Connect with Jamie Rubin and ILG:

Host - https://www.infolawgroup.com/jamie-rubin 

Website - https://www.infolawgroup.com/

LinkedIn - https://www.linkedin.com/company/infolawgroup-llp/

Email - [email protected]

In this episode, Heather Nolan and the ILG marketing law team break down the top marketing compliance priorities for 2026. As regulators intensify enforcement and plaintiff’s attorneys grow more aggressive, brands are being judged not only by what they promise, but by how their marketing systems function in practice.

From influencer disclosure failures and deceptive review practices to subscription compliance crackdowns and evolving FDA food labeling standards, the message is clear: marketing compliance must be proactive, documented, and continuously monitored. The team also highlights rising scrutiny around environmental claims and donation-based marketing programs, offering practical steps companies can take now to reduce exposure before enforcement actions or litigation hit.  

In this episode, Heather and the ILG team (Jamie, Mindy, Ben, Sophia) discuss:

• Influencer compliance risks and the increasing liability brands face for influencer misconduct
• FTC enforcement under the Consumer Review Rule, including fake reviews and review suppression
• FDA efforts to modernize food labeling and extend packaging rules to online product listings
• Subscription and auto-renewal compliance, including state law developments and ongoing FTC rulemaking
• Green marketing claims, including aspirational sustainability promises and recyclability representations
• Donation-based marketing programs and new state registration requirements

"Keeping tabs on influencers, monitoring influencer activity, and enforcing influencer contracts is now more important than ever to help stem the increasing legal exposure in connection with engaging influencers.” - Jamie Rubin

"Now's a good time to review your labels, assess your online listings, prepare for enforcement, and just really get your ducks in a row before you know these changes come.” - Mindy Abern

"If I'm a business that sells subscriptions, I would want to take a look and make sure our processes are fully compliant, and to remember that this one's not set in, forget it.” - Ben Stein

"Take some time to reflect on and refresh your green claims that you're currently making.” - Sophia Allen

Connect with InfoLaw Group:

Jamie Rubin - https://www.infolawgroup.com/jamie-rubin 

Mindy Abern - https://www.infolawgroup.com/mindy-abern 

Ben Stein - https://www.infolawgroup.com/benjamin-stein 

Sophia Allen - http://www.infolawgroup.com/sophia-allen 

Connect with Heather, Brian, and ILG:

Heather Nolan - https://www.infolawgroup.com/heather-nolan

Brian Schaller - https://www.infolawgroup.com/brian-schaller   

Website - https://www.infolawgroup.com/

LinkedIn - https://www.linkedin.com/company/infolawgroup-llp/

Email - [email protected]

In this episode, Heather Nolan and the ILG privacy law team break down the top privacy, AI, and consumer protection priorities organizations should focus on in 2026.

As regulatory scrutiny intensifies, companies are no longer being judged solely on their written policies, but on how their systems operate in practice. From children’s data protection and evolving AI governance requirements to comprehensive state privacy law amendments and increased auditing expectations, regulators are signaling clear expectations: rigor, documentation, and accountability are non-negotiable.

The team offers practical guidance on where legal departments should invest time and budget now to avoid costly enforcement actions later, emphasizing cross-functional coordination across HR, marketing, product, and IT.

In this episode, Heather and the ILG team (Tatyana, Joyce, Mark, Rosie) discuss:

• The surge in children’s privacy enforcement, including COPPA amendments taking effect in April 2026
• Age verification and age assurance challenges, including biometric and digital ID considerations
• The intersection of AI regulation and HR practices, particularly automated decision-making in hiring
• New and amended comprehensive state privacy laws in Indiana, Kentucky, Rhode Island, California, Connecticut, and Oregon
• The growing emphasis on auditing, opt-out mechanisms, cybersecurity, and regulatory reporting
• Consumer protection risks tied to AI-generated outputs and interactive systems

"We can no longer turn a blind eye and just say we're a general audience service, and we really don't intend to have anyone younger than 18, if that's not really the actuality.” - Tatyana Ruderman

"2026 businesses should be keeping an eye out for the new and amended comprehensive privacy laws taking effect this year.” - Joyce Kim

"The regulators have largely reached the conclusion that they don't trust businesses to just write policies and actually follow them.” - Mark Paulding

"Internal AI governance will be very key to mitigating businesses' risks of liability for inaccurate output.” - Rosanne Yang

Connect with InfoLaw Group:

Tatyana Ruderman - https://www.infolawgroup.com/tatyana-ruderman 

Joyce Kim - https://www.infolawgroup.com/joyce-kim 

Mark Paulding - https://www.infolawgroup.com/mark-paulding 

Rosanne Yang - https://www.infolawgroup.com/rosanne-yang 

Connect with Heather, Brian, and ILG:

Heather Nolan - https://www.infolawgroup.com/heather-nolan

Brian Schaller - https://www.infolawgroup.com/brian-schaller   

Website - https://www.infolawgroup.com/

LinkedIn - https://www.linkedin.com/company/infolawgroup-llp/

Email - [email protected]

Where law meets launch.

ILG On-Demand: Privacy & Ad Law in the Trenches is your front-row seat to candid conversations between seasoned attorneys and in-house counsel facing the legal complexities of business today. From data-driven marketing to cutting-edge AI, product development to global privacy compliance—our episodes tackle the real-time legal dilemmas shaping tech, media, and consumer experience.

Hosted by lawyers from InfoLawGroup®—a boutique firm built at the crossroads of privacy, advertising, technology, and IP—each episode dives into the legal strategy connected with the business decisions.

Whether you’re in-house legal, C-suite, product, marketing, or compliance, this podcast is for you.

Connect with Heather, Brian, and ILG:

Website- https://www.infolawgroup.com/

LinkedIn- https://www.linkedin.com/company/infolawgroup-llp/

Email- [email protected]

Heather Nolan- https://www.infolawgroup.com/heather-nolan

LinkedIn- https://www.linkedin.com/in/heatherenolan/

Email-  [email protected]

Brian Schaller- https://www.infolawgroup.com/brian-schaller

LinkedIn- https://www.linkedin.com/in/brianschaller/

Email-  [email protected]

In the inaugural episode of the ILG on demand podcast, Sara Chubb discusses the launch of Chicago Sports Network (CHSN) with General Counsel Karen Klein. CHSN, which covers the Chicago Blackhawks, Chicago Bulls, and Chicago White Sox, launched in six months instead of the usual 18 or more it takes to launch a network of this size. Key early priorities included securing talent agreements, engaging the production crew, and setting up advertising terms. Klein emphasized the importance of understanding the league's policies and building relationships with stakeholders. The network also launched a direct-to-consumer app, requiring close collaboration with the product team to ensure compliance and a seamless user experience.  

In this episode, Sara and Karen discuss:

• How in-house counsel effectively balance the needs of internal stakeholders and external partners when launching new products
• Ensuring transparency and respect for consumer privacy when building new products and features
• The importance of building trust and strong relationships with key stakeholders, and understanding what’s most important to them.
• When you are on a tight timeline, sometimes you have to 

"The key thing was, on October one, the games had to be shown on the air, and the actual production quality had to be excellent. So that really helped me prioritize things, the talent agreements and engaging production crews, that had to come first. " 

—  Karen Klein

Connect with Sara and ILG:

Sara Chubb- https://www.infolawgroup.com/sara-skinner-chubb

Email-  [email protected]

Website- https://www.infolawgroup.com/

LinkedIn- https://www.linkedin.com/company/infolawgroup-llp/

Email- [email protected]

Connect with Karen and CHSN:

Website- https://www.chsn.com/

LinkedIn- https://www.linkedin.com/in/karen-klein-6180a52/

Instagram- https://www.instagram.com/chsn/?hl=en

X- https://x.com/CHSN__

Facebook- https://www.facebook.com/chsn