In this episode of Notes to My (Legal) Self®, host Olga V. Mack speaks with Rina Wang, former Assistant General Counsel at AI startup Prepared, about what it really means for lawyers to build a career inside venture-backed startups, especially during periods of uncertainty, hypergrowth, and rapid change.

Drawing from her journey across litigation, multiple venture-backed startups, and a recent acquisition by Axon, Reena offers a candid perspective on what lawyers should expect when they step into startup life.

Together, they explore:

• Why uncertainty isn’t a flaw of startups; it’s a defining feature

• How one year in a startup can feel like 10 years in a Fortune 500 company

• What it means to make career decisions with limited information

• How lawyers can shift from risk-avoidance to value creation in fast-moving environments

• Why startups force accelerated learning, leadership, and personal growth

If you’re a lawyer considering a move into a startup or questioning whether speed, ambiguity, and change are worth the tradeoff, this conversation offers an honest look at the realities behind the hype.

Explore more episodes, insights, and reflections at:

🌐 www.notestomylegalself.com

#NotesToMyLegalSelf #StartupLife #InHouseLegal #CareerGrowth #LegalLeadership #AIStartups

In this episode of Notes to My (Legal) Self®, host Olga V. Mack sits down with John Pavolotsky, technology transactions attorney, privacy and cyber expert, and co-head of the AI practice at Stoel Rives, to unpack the fast-changing world of AI contracting.

With 25 years of experience across startups, Big Tech, and private practice, John brings a grounded, practical view of how lawyers can draft, negotiate, and manage AI-related agreements when the regulatory landscape is evolving by the month.

Together, they explore:

• How to draft AI contracts amid shifting state and global regulations• What counts as “high-risk” use cases under laws like the EU AI Act and Colorado AI Act

• How AI is changing traditional risk allocation, compliance, and licensing terms

• Why lawyers must experiment with AI tools now to stay future-ready

• The unique role in-house counsel play in shaping responsible AI adoption

If you want a clear, candid look at the current and near-future state of AI contracting, and what legal teams should be doing today to prepare, this episode delivers essential insights from one of the field’s most experienced practitioners.

Explore more episodes, blogs, and insights at our official site:🌐 www.notestomylegalself.com

#AIContracting #LegalTech #LegalInnovation #FutureOfLaw #TechTransactions #AIRegulation

In this episode of Notes to My (Legal) Self, host Olga V. Mack talks with Carl Davidson, a former immigration attorney turned product leader and now co-founder of Candle AI, about one of the biggest pain points in legal practice: email overload, and why he left law to fix it.

Carl recounts his path from corporate and immigration law to Silicon Valley, where he saw firsthand how constant client messages, fragmented data, and inbox chaos slow lawyers down. He realized the real bottleneck wasn’t the law, it was the inbox.

Now building Candle AI, Carl is focused on reducing administrative drag, centralizing client context, and helping legal professionals reclaim their time by bringing structured data directly into email.

Together, Olga and Carl explore what happens when a lawyer becomes a builder, and how fixing “small” workflow problems can create outsized impact across the legal industry.

In this conversation, they explore:

• Carl’s transition from practicing attorney to product manager at Intuit

• How a lack of structured data creates chaos in legal workflows

• Why email remains the #1 source of friction, stress, and lost time for lawyers

• The “magic moment” principle in product design, and why it matters for adoption

• How Candle AI brings case context directly into Gmail/Outlook to eliminate tab-switching

• Why client communication still defaults to email despite modern tools

• The rise of founder-builders in legal tech and the role AI plays in enabling them

• Why small firms and solo practices must not be left behind in the AI revolution

Key Learning Outcomes:

• Understand why email overload is a systems problem—not a personal efficiency failure

• See how integrated AI can reduce context switching and reclaim billable time

• Learn how to follow user pain to build products lawyers actually adopt

• Explore how structured data unlocks powerful automation across the legal stack

• Gain insight into the future of legal practice—and why lawyers who build will shape it

If you’ve ever felt buried under email, frustrated by scattered information, or curious about how AI can make legal work lighter, this episode will show you how one former attorney turned that frustration into a mission, and a company.

🌐 Explore more episodes, blogs, and insights at:
http://www.notestomylegalself.com

#LegalInnovation #ProductManagement #LegalEmail #FutureOfLaw #NotesToMyLegalSelf

In this full episode of Notes to My (Legal) Self, host Olga V. Mack sits down with Dorna Moini, CEO and founder of Gavel, to explore how automation, no-code tools, and AI are empowering lawyers to scale their practice, streamline workflows, and expand access to justice, without burning out or billing more hours.

Dorna shares her journey from Big Law litigator at Sidley Austin to legal tech entrepreneur. Her pro bono work with domestic violence survivors inspired her to create an online tool that evolved into Gavel, a leading legal automation suite that helps lawyers build repeatable, rules-based systems for client intake, document drafting, and negotiation.

Together, they unpack what it means to build, not bill, and how forward-thinking legal professionals can use technology to serve more clients with less effort.

In this conversation, they explore:

• What it means to productize your legal services and turn expertise into scalable offerings

• How automation and AI can increase revenue without increasing billable hours• The difference between rules-based automation and generative AI, and when to use each

• How Gavel helps lawyers build “TurboTax for law” solutions without writing a line of code
• Real-world examples of scalable legal services that expand access to justice
• Why legal education is shifting to teach lawyers how to build systems, not just spot issues

Key Learning Outcomes:

• Learn how to scale your legal practice through automation and no-code tools

• Understand how to combine rules-based logic and AI to improve speed and quality

• Discover how automation frees up time for strategy, empathy, and client relationships
• Explore practical ways to package your expertise into repeatable, revenue-generating systems
• Gain insight into the future of legal practice, one built by lawyers who build

If you’ve ever wondered how lawyers can scale with automation and move beyond the billable hour, this episode will show you how to start building smarter, not harder.

🌐 Explore more episodes, blogs, and insights at:⁠ http://www.notestomylegalself.com

#LegalTech #Automation #LegalAutomation #AccessToJustice #LegalInnovation

In this full episode of Notes to My (Legal) Self, Karl Seelbach, litigation attorney and founder of Skribe.ai, explores how technology and AI are reshaping courtroom practice, legal testimony, and the very fabric of the litigation process.

Karl shares his journey from a traditional courtroom litigator defending Fortune 500 companies to building a software platform that makes capturing legal testimony faster, smarter, and more accessible. He unpacks the challenges of bridging law and technology, the ethics of AI in litigation, and what it takes to go from practicing lawyer to legal tech founder.

Karl explores:

• Why the traditional deposition process is costly, outdated, and ready for disruption

• How Skribe.ai leverages software and AI to modernize testimony capture

• The nationwide shortage of stenographers, and what “non-stenographic depositions” mean for the future

• How remote technology can improve efficiency, access to justice, and judicial transparency
• The ethical and practical implications of generative AI in law
• Lessons from Karl’s entrepreneurial journey, from overbuilding MVPs to finding product-market fit

Key Learning Outcomes:
• Understand how AI is transforming depositions, hearings, and transcript creation

• Learn how to navigate resistance to innovation in traditional legal practices

•Gain insights into balancing ethics, technology, and client stewardship
• Explore how GenAI can improve speed, accuracy, and access to justice
• Discover what it takes to transition from litigator to legal tech innovator

If you’re a litigator, in-house counsel, or legal tech enthusiast curious about how generative AI and software are transforming the legal landscape, Karl’s story offers a powerful look into the next chapter of modern law.

🌐 Explore more episodes, blogs, and insights at:
http://www.notestomylegalself.com

#LegalTech #Litigation #AIinLaw #LegalInnovation #SkribeAI #NotesToMyLegalSelf

In this episode of Notes to My (Legal) Self®, Olga V. Mack sits down with Senne Mennes, former Big Law lawyer turned Co-Founder of ClauseBase, a company revolutionizing how legal professionals draft documents using automation and AI-powered tools.

Together, they explore how Senne transitioned from traditional legal practice to entrepreneurship—and what every lawyer can learn from his journey.

Here’s what you’ll explore: • How Senne went from drafting contracts at DLA Piper Brussels to co-founding a legal tech company

• The skills that truly transfer from law to entrepreneurship (and the ones you’ll have to learn fast)

• Why redefining your relationship with risk is crucial for innovation and growth • Emerging trends shaping the future of legal careers, from Gen AI to new hybrid roles like legal engineers.

If you’ve ever wondered what life beyond the traditional legal path could look like, this conversation will inspire you to chart your own route.

🌐 Explore more episodes, blogs, and insights at:

http://www.notestomylegalself.com

#LegalInnovation #Entrepreneurship #InHouseCounsel #CareerPivot

Season 13, Episode 3: Legal Tech Disruptors, New Minds Innovating for Good (ft. Kara Peterson)

In this episode of Notes to My (Legal) Self®, host Olga V. Mack sits down with Kara Peterson, a marketing communications leader and co-founder of descrybe.ai, a legal tech startup democratizing access to legal information through AI.

Kara’s story is as inspiring as it is unexpected. Coming from a background in public health and social justice, she never imagined she’d one day help build a legal AI company, let alone one that has summarized millions of judicial opinions across the U.S. for free.

Together, Olga and Kara explore:

• How AI can bridge the justice gap by making law more understandable and accessible

• Why passion for justice isn’t limited to lawyers

• The power of cross-disciplinary collaboration (and yes, the advantages of “marrying an engineer”)

• What legal tech can learn from public health about tackling systemic inequities

If you’ve ever wondered how innovation, empathy, and a touch of humor can reshape access to justice, this conversation will leave you both informed and inspired.

Explore more episodes, blogs, and insights at our official site:

🌐 www.notestomylegalself.com

#LegalPodcast #InHouseCounsel #LegalTech #LegalInnovation #FutureOfLaw #AIinLaw #AccessToJustice #Leadership #LegalCareer

Season 13, Episode 2: The Gig Economy for Lawyers is Coming (ft. Otto Hanson)

In this episode of Notes to My (Legal) Self, host Olga V. Mack sits down with Otto Hanson, Co-Founder and CEO of TermScout and Screens, for a forward-looking conversation about innovation, productization, and trust in legal technology.

Otto shares how TermScout became the first platform to certify fairness in B2B contracts, how Screens enables lawyers to build and share AI-powered contract playbooks, and why the next evolution of legal work will combine human expertise with technology, not replace it.

Together, Olga and Otto explore:

• How AI is unlocking new business models in law

• What “productized legal services” mean for practitioners and clients

• Why a trust gap still exists between lawyers and AI

• How certification and transparency can reduce sales friction

• The steps every lawyer can take to start experimenting with AI safely and effectively.

If you’re curious about the intersection of AI, contracts, and the future of legal work, this episode will inspire you to think like a builder and have fun doing it.

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#GigEconomy #InHouseCounsel #ScreensAI #OlgaVMack #TermScout

In this full episode of Notes to My (Legal) Self, Olga V. Mack sits down with Basha Rubin, CEO and Co-Founder of Priori to explore how legal marketplaces are transforming the way in-house teams find, hire, and manage outside counsel.Basha shares her journey from Yale Law School during the 2008 recession to co-founding Priori in 2013, and how the company evolved from serving individuals and small businesses to partnering with Fortune 10 enterprises.

Together, Olga and Basha dive into the rise of legal marketplaces, the role of data and AI in decision-making, and why alternative providers are reshaping the future of legal services.

Together, Basha and Olga explore:

• Why the traditional big law model underserves many clients

• How in-house teams can categorize legal work by risk and complexity

• Practical benefits of marketplaces for efficiency, cost savings, and expertise

• The growing importance of data-driven, defensible legal decisions

• How AI and technology are shaping the future of outside counsel management

Key Learning Outcomes:

• Understand how legal marketplaces provide alternatives to big law firms

• Learn strategies for smarter allocation of legal work across risk levels

• Discover how data and scorecarding can improve outside counsel selection

• Gain insight into the impact of AI on in-house counsel decision-making

• Explore the future of legal services through Priori’s marketplace model.

If you’re an in-house lawyer, legal ops professional, or legal leader seeking innovative ways to manage outside counsel, Basha’s insights offer a roadmap for embracing efficiency, transparency, and strategic value.

In this episode of Notes to My (Legal) Self, Olga Mack sits down with Adriana Dulic, Chief Compliance Officer at a leading fintech company, to explore the powerful intersection of legal compliance, leadership, and service.

Adriana shares her journey from private practice to a long-term in-house and compliance career, shaped by the dynamic world of financial technologies and regulatory change. But beyond her corporate role, Adriana offers a compelling case for why lawyers should make pro bono and community engagement a core part of their professional lives.

In this conversation, you'll learn:

• What a day in the life of a CCO in fintech really looks like

• How compliance careers evolve with tech innovation and global oversight

• Why pro bono work builds leadership skills and business acumen

• How community service can ground legal careers in purpose and perspective

• What lawyers need to thrive in highly regulated, fast-paced industries

Whether you're charting a path in compliance, looking to make a meaningful career pivot, or seeking ways to serve beyond billable hours, this episode offers practical strategies and heartfelt insights on leading with integrity and impact.