Your Startup Lawyer

Kristina Subbotina
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Welcome to Kristina's podcast, the show where startup founders and VCs talk real. Hosted by ex–big law attorney turned legal tech startup founder Kristina Subbotina, this show brings you candid conversations with top founders, investors, and operators—plus solo episodes breaking down essential legal strategies for scaling your company. Whether you're navigating your first term sheet or dealing with co-founder drama, this is your tactical edge.

  1. JAN 27

    If You’re Starting a Company in 2026, Watch This | Amber Illig

    In this episode, we sit down with Amber Illig, General Partner at The Council, to unpack what it really takes to become a founder in the age of AI.Amber shares hard truths about why not everyone should start a company, why the first 1–2 years of founding are the most psychologically brutal, and how operators can transition into founders without romanticizing the struggle. 00:00 Why not everyone should be a startup founder01:20 Operator to founder: how Amber Illig got started02:45 Angel investing & building Council Angels05:00 Who actually makes a good first-time founder07:15 When to quit a stable job to start a company09:00 Learning startup language & fundraising basics11:20 Why the first 2 years of a startup are the hardest13:45 How founders handle failure, fear, and uncertainty16:30 Founder comparison trap (Elon Musk problem)18:00 Delegation vs perfectionism in early startups20:30 Using AI and vibe coding to move faster23:30 How founders set quality standards for teams26:30 Direct feedback, leadership, and startup culture31:30 Founder confidence and leadership growth36:00 Power dynamics in managing employees39:30 AI, consciousness, and the future of humans44:10 Finding meaning beyond money and success48:05 Final lessons for founders and operators

    51 min

  2. 07/09/2025

    #19 VC Itamar Novick on AI, Legal Tech, and the Future of Law

    In this conversation, Kristina Subbotina sits down with Itamar Novick, founder and solo GP of Recursive Ventures, a pre-seed fund focused on AI and emerging tech. Itamar has sat on every side of the startup table—founder, operator, institutional VC, and now solo capitalist. He’s helped scale companies like Life360 from seed to IPO and has backed over 100 startups, including breakout names like Deel, HoneyBook, Placer.ai, and Tile. Named a Top 100 Global Seed Investor by Business Insider, Itamar brings a rare combination of operational depth and investing clarity. Together, Kristina and Itamar explore the evolving landscape of legal tech, the growing impact of AI on legal and venture ecosystems, and the rising importance of trust in professional services. They unpack the challenges and opportunities in automating legal workflows, the power of social media in bridging founders and investors, and how venture capital is evolving in a market shifting toward capital efficiency and “seed strapping.” This episode is a must-listen for founders navigating high-stakes decisions—from building early investor relationships to understanding the human edge in an increasingly automated world. Whether you're launching your first company or scaling your next one, this conversation delivers sharp insights, fresh perspectives, and hard-earned lessons. Takeaways - The power of social media can significantly impact legal tech.- Founders often lack awareness of what they don't know.- Legal services are evolving with the integration of AI.- Building trust with clients is crucial in legal services.- The future of legal tech will involve more automation and AI.- Human oversight will remain essential in legal practices.- The venture capital landscape is shifting towards seed strapping.- Founders should focus on building relationships with investors.- Legal tech must balance automation with quality service.- The importance of personal connections in the startup ecosystem. Chapters 00:00 Navigating the Landscape of Legal Services02:43 The Power of Social Media in Legal Marketing05:41 Innovations in Legal Tech and AI Integration08:37 The Future of Law: Balancing Human and AI Roles11:34 Building Trust in Legal Services14:38 The Shift Towards Service as Software17:48 The Role of Influencers in Legal Services20:44 Challenges in Legal Automation23:33 The Human Element in Legal AI26:24 The Future of Legal Practice: A Hybrid Approach34:50 Understanding Complexity in Startups36:23 The Role of AI in Legal Practices39:26 Human-Machine Interaction in AI41:14 The Evolution of Legal Practices43:09 The Future of Venture Capital45:03 The Value of Specialized Investors49:13 Navigating Asymmetry in Fundraising50:44 The Concept of Seed Strapping54:15 The Shift in Startup Funding Dynamics01:01:23 The Importance of Founder-Investor Alignment

    1h 4m

  3. 06/30/2025

    #18 VC Martin Tobias: You have one job as a CEO: don't die. Don't run out of money.

    In this conversation, venture investor Martin Tobias shares his insights on the startup journey, emphasizing the importance of resilience, understanding investor motivations, and the necessity of hiring the right team. He discusses the challenges founders face, the significance of mindset, and how AI is transforming the startup landscape. We also touch on the legal aspects of starting a business and the traits that make a successful founder. Martin Tobias is not just an investor—he’s an operator, a futurist, a biohacker, and someone who deeply understands what it takes to build enduring companies. He has seen it all—from being a 3x venture-backed CEO and raising over $500 million to leading two IPOs, to now backing some of the most friction-killing startups around the globe. He was an early investor in many unicorns, such as Google, DocuSign, OpenSea and Deel. As the Managing Partner at Incisive Ventures, Martin invests in early-stage B2B software companies that reduce friction at scale. His unique lens combines hard-earned founder wisdom with a global investment thesis. takeaways The startup journey is filled with challenges that require resilience.Understanding investor motivations can help founders navigate funding.Defensive founders are often a red flag for investors.Hiring the right team is crucial for scaling a startup.Curiosity and a positive mindset are essential for success.Founders should be prepared to face adversity and learn from it.AI tools can significantly enhance startup efficiency and innovation.It's important to choose co-founders wisely and ensure alignment.Legal considerations are vital in the early stages of a startup.Successful founders often have a unique insight into their market. Chapters 00:00 The Startup Journey: Embracing Challenges 02:58 Understanding VC Motivations and Founder Dynamics 05:48 The Importance of Fit: VCs and Founders 08:59 The Role of Operators in Evaluating Founders 11:47 Red Flags in Founders: Defensive Traits 14:55 Mindset Matters: Curiosity vs. Defensiveness 17:51 Finding Opportunity in Adversity 21:10 The Poker Analogy: Risk and Decision Making 30:43 Strategic Risk-Taking in Startups and Poker 32:33 Disrupting Incumbents: The Startup Advantage 34:05 The Power of Going All In 36:30 Living in the Present: Overcoming Fear and Anxiety 38:58 Learning from Mistakes: The Importance of Investor Dynamics 42:47 Navigating the Funding Landscape: Lessons Learned 45:31 The Changing Landscape of Startup Funding 48:01 Innovative AI Tools for Founders 50:48 Rapid Fire Founder Insights

    1 hr

  4. 05/28/2025

    #17 Shamak: This Indian kid came to the U.S. to study computer science and became a famous influencer

    How Shamak and Kristina grew from 0 to 40k followers on Instagram while being introverts Follow ‪@shamakinusa‬ and ‪@KristinaSubbotinaEsq‬

    31 min

  5. 04/07/2025

    #16 Megan Lightcap of Slow Ventures: How Content Creators Become Unicorns

    Content creators are no longer just influencers—they're building high-growth startups, securing venture funding, and scaling into billion-dollar businesses. In this session with Megan Lightcap (investor at Slow Ventures), and Kristina Subbotina (ex-Cooley startup lawyer and founder of Lexsy) you will learn what separates those who succeed at scale from the rest. What you’ll learn: ✅ How content creators can evolve into founders & build billion-dollar companies ✅ What investors look for when backing creator-led startups ✅ The playbook for scaling from audience to enterprise Links mentioned: Startup Launch Checklist: https://stan.store/Lexsy/p/my-free-startup-launch-checklist Investor Due Diligence Checklist: https://stan.store/Lexsy/p/get-my-free-investor-due-diligence-checklist Startup Launch Package: https://stan.store/Lexsy/p/startuplaunch Startup Due Diligence Package: https://stan.store/Lexsy/p/legal-prep-for-fundraising Follow us for more startup content: 📍 Megan Lightcap: https://www.linkedin.com/in/megan-lightcap-513ab96b/ 📍 Kristina Subbotina: https://www.linkedin.com/in/kristinasubbotinaesq/

    34 min

  6. 03/31/2025

    #15 Josh Constine: Fundraising Tips for Startup Founders

    In this session, Josh Constine (Venture Partner at SignalFire, former TechCrunch Editor-At-Large) joins Kristina Subbotina (ex-Cooley startup lawyer and founder of Lawlace & Lexsy) to walk you through what really matters in early-stage fundraising—how to get investor attention and tell a compelling story. You’ll learn: How to build a targeted investor funnelWhat makes a pitch deck effective (with real examples)The legal foundation you actually need before you raiseCommon founder mistakes that turn off VCsWe didn’t go deep into due diligence, but here are the links I promised: 🔗 https://stan.store/Lexsy/p/get-my-free-investor-due-diligence-checklist🔗 https://stan.store/Lexsy/p/pitchdeck🔗 https://stan.store/Lexsy/p/legal-prep-for-fundraising Follow us for more startup content:📍 Josh Constine: https://x.com/JoshConstine📍 Kristina Subbotina: https://www.instagram.com/kristinasubbotina.esq/

    47 min

  7. 10/18/2024

    #14: Ankur Nagpal, Personal Finances and Dating for Startup Founders 101

    In this episode of Kristina's podcast, Kristina sits down with Ankur Nagpal, who is in his early thirties with a net worth north of nine figures. He started making money in college with his Facebook App business, but his real life-changing moment was when he sold his company Teachable for a quarter billion dollars. Now, he's the founder of the fintech company Carry. Ankur shared what it was like growing up as a third culture kid, being born in India, moving to Oman, and then pursuing higher education in the US. He talks about maintaining happiness while pursuing wealth, and the financial strategies and tax efficiencies that have shaped his success. Ankur emphasizes the critical aspects of founder finances, such as setting personal salary limits, properly handling taxes with tools like the 83(B) election and QSBS, and the necessity of maintaining a business emergency fund. Kristina and Ankur also discussed if it’s possible to be happy as a founder and in your personal life, why Ankur doesn’t believe in splitting things 50/50 in a relationship and why he would never dare to send a Venmo request after a date. Timestamps: 00:00 Introduction 02:20 Achieving Financial Freedom in College 03:11 Lessons on Taxes & Early Financial Mistakes 04:20 Scaling Teachable to $60M ARR 06:55 Investing in Startups: Ankur’s $20M Strategy 10:25 Starting Carry & Simplifying Founder Finances 11:40 Selling a Company for $250M: What Comes Next? 13:35 Lessons as a Second-Time Founder 17:50 Rethinking Legacy and Personal Impact 19:18 Walking Away from $10M in Equity 20:10 Framework for Personal Happiness 26:00 Balancing Financial Success and Personal Happiness 28:00 Who Should Pay on Dates? 30:01 Quality Time with Loved Ones 30:50 Can Exes Stay Friends? 32:40 Should Men Be Providers? 39:45 Planning Personal Finances as a Founder 40:44 How to Set Your Founder Salary 42:53 Investor Due Diligence Red Flags 45:30 Building Long-Term Investor Relationships 48:20 Why Debt is Dangerous for Founders 49:40 Building Your Budgeting Plan 51:20 Optimizing Taxes: 83(b) and QSBS Essentials 52:00 Tax-Saving Strategies for Founders 55:50 Founders’ #1 Priority 56:30 Advice to First-Time Founders

    58 min

  8. 09/13/2024

    #13: Adam Spector, Your startup will scale faster if you stop doing too much

    In this episode, Kristina talks with Adam Spector, founder and CEO of Levy, about the game-changing benefits of outsourcing back-office tasks for startups. Adam shares his 14-year journey in Silicon Valley, where he learned the value of focusing on core competencies while outsourcing everything else, a strategy he calls “startup plumbing.” They dive into the inefficiencies of traditional business operations and how poor time management can be a costly mistake for founders. Adam highlights how leveraging AI and remote work capabilities is reshaping the future of business, making it easier for startups to scale and stay agile. Throughout the conversation, Adam emphasizes the importance of staying hungry, curious, and adaptable in today’s fast-paced, tech-driven world. This episode is packed with actionable insights on streamlining operations and future-proofing your startup! Timestamps: 00:00 Introduction: Maximizing Time Value 00:13 Meet Adam Spector: Startup Plumber 00:29 The Role of Levy in Startups 01:47 Challenges in Back Office Operations 02:31 When to Outsource: A Founder's Dilemma 05:44 The Importance of Delegation 19:02 The Future of Work: AI and Outsourcing 21:34 Bootstrapping vs. Venture Capital 27:58 Empowering Entrepreneurs Globally 29:01 Challenges and Vision for the Future 29:37 Affordable Back Office Solutions 31:20 Personal Anecdotes and Outsourcing 32:55 The Importance of Outsourcing 39:37 Remote Work and Company Culture 39:47 Vulnerability and Imposter Syndrome 46:14 The Future of Work and AI 50:41 Staying Curious and Embracing Change 51:49 Adam’s Final Thoughts and his Advice to his Younger Self

    55 min
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About

Welcome to Kristina's podcast, the show where startup founders and VCs talk real. Hosted by ex–big law attorney turned legal tech startup founder Kristina Subbotina, this show brings you candid conversations with top founders, investors, and operators—plus solo episodes breaking down essential legal strategies for scaling your company. Whether you're navigating your first term sheet or dealing with co-founder drama, this is your tactical edge.

Information

  • Creator
    Kristina Subbotina
  • Years Active
    2023 - 2026
  • Episodes
    19
  • Rating
    Explicit
  • Copyright
    © Kristina Subbotina
  • Show Website
    Your Startup Lawyer