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

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

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

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/

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:

1. How to build a targeted investor funnel
2. What makes a pitch deck effective (with real examples)
3. The legal foundation you actually need before you raise
4. Common founder mistakes that turn off VCs

We 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/

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

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

In this episode of Kristina's podcast, Andre Gharakhanian, founder and partner of Silicon Legal Strategy, shares his inspirational journey from working in Big Law to building one of the most successful law firms in the U.S. Andre and Kristina discuss the importance of mentorship, the legacy of impactful work, the challenges of managing and hiring people, and the significance of authenticity in distinguishing yourself from the competition. Listen in to learn valuable lessons and insights from Andre's extensive experience in startup law and entrepreneurship.

In this episode, I interview Vaik Mugunthan, a co-founder and CEO of DynamoAI. He raised $19.4M from top-tier venture investors to enable large enterprises to deploy generative AI models in a compliant manner. We discuss his founder journey, the role of San Francisco in building a successful startup, the meaning of life, how to live a happy life, and the impact of AI on various aspects of life and business.

00:00 - intro

Everything you need to know about taxes: capital gains tax, QSBS, 83(b), and other gibberish that really matters. We sat down with Alex Roytenberg, a CPA for startups and venture investors.