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
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:
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. Timestamps: 00:00 - How Andre's Journey Started 02:01 - What Legacy Do You Want to Leave Behind? 07:29 - How to Be a Good Manager and Mentor 11:20 - Building Your Team: Why You Shouldn’t Hire Partners 22:37 - The Power of Authenticity and Being Yourself Through It All 30:05 - Using Criticism to Grow 31:16 - Building Your Network as a Founder 31:52 - How to Handle Negative Feedback and Complex Client Dynamics 33:11 - The Two Essential Components to Build Strong Client Relationships 34:15 - One Quality That Makes Good Founders Great 37:42 - Sticking to Your Vision While Ensuring Your Firm Grows and Develops 51:19 - Andre’s Worst Mistake and What He Learned
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 00:26 - about DynamoAI 00:50 - the American dream of Vaik 02:00 - founder journey 03:00 - Vaik about his founder journey 05:14 - what it’s like studying at MIT 07:00 - the role of San Francisco in building a successful startup 10:00 - New York vs San Francisco; when founders can move out of San Francisco 10:47 - do money make you happy? meaning of life 11:50 - humans vs AI, what species should survive? 13:56 - what is success in life? 15:10 - what’s comfortable life? 16:30 - vision for DynamoAI 18:12 - what helps you to succeed in life? 21:04 - how to use AI in legal services? 21:17 - advice to your younger self 22:30 - exercise to ensure you live a happy life 24:50 - Mark Zuckerberg as a founder’s example 25:33 - the role of religion in life 29:18 - what investors should you take money from? 33:05 - advice to entrepreneurs
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.
In this episode, I'm interviewing my client and friend Aris Yeager aka the european kid.
Besides bootstrapping, selling the company, or declaring bankruptcy, you've got two options: a down round or a cram down, aka "pay-to-play" or a recap. In this episode, I'll explore how to initiate and carry out this process without landing in legal hot water.
