Explore every episode of the podcast The Kristina Subbotina Show

This episode of the Kristina Subbotina show is for the builders. Jody Glidden started coding at 7, launched his first business at 9, and bought a car at 14 (two years before he could actually drive it.) Now on his fifth company, Jody has raised close to $200M across his career, built and exited multiple startups (including IntroHive at $400M+), and is currently running Postalize, a legal tech company valued at nearly $100M with just 20 employees. In this episode, Kristina and Jody go deep on: Why raising less money leads to bigger exits and how he built a $100M company on just $7.7M raised The real math of dilution: how he owned under 10% by the time he left his biggest company The all-stock deal that crashed 16x during the dot-com bust and the lockup that trapped him How BlackBerry acquired his company on the drive home from a fundraising meeting — during the 2008 crash Running a 20-person team with the output of 150 by using AI to actually do work, not just answer questions Building automated code reviews with a "model council" that doubled developer productivity Why he has no assistant — and how AI skills for travel, CRM, and sales pipeline replaced the need for one Board dynamics, voting control, and what happens when investors vote against you The COVID playbook: CEO takes 50% pay cut, lowest-paid employees take zero — and Glassdoor ratings hit all-time highs Why "I don't know how to code" is no longer an excuse to raise money before building a product His take on AI adoption: we're at 1998-level internet adoption — only 2% of the world is using AI to actually do work Jody is one of those founders who doesn’t prioritize delegation. He still codes, still sells, still does post-sale himself. This conversation will change how you think about building, raising, and scaling. Follow Kristina Subbotina for more conversations with founders, investors, and operators building extraordinary companies and extraordinary lives. Instagram: https://www.instagram.com/kristinasubbotina.esq LinkedIn: https://www.linkedin.com/in/kristinasubbotina/ YouTube: https://www.youtube.com/@kristinasubbotina Subscribe for new conversations every week.

Yosef Martin is the founder of BoxyCharm, the beauty subscription company he bootstrapped from scratch into a business generating more than $500 million in annual revenue before selling it to Ipsy in a deal worth over $500 million. Without raising venture capital or having any experience in the beauty industry, Yosef built one of the fastest-growing direct-to-consumer brands by mastering organic growth, influencer marketing, and community-driven customer acquisition. Today, he's building PepNow, a longevity company focused on peptide-based health products, where he's applying the same founder playbook to an entirely new industry. In this conversation, Yosef shares why he believes founders should stop following their passion and start chasing opportunity, how he built a business that reached hundreds of millions in revenue almost entirely through organic marketing, why he never raised venture capital, and the lessons he learned from selling his company. They also discuss what Yosef believes is the meaning of his life. Beyond the businesses he’s built and the money he’s mad—because why bother striving for longevity if you’re living a meaningless life? Follow Kristina Subbotina for more conversations with founders, investors, and operators building extraordinary companies and extraordinary lives. Instagram: https://www.instagram.com/kristinasubbotina.esq LinkedIn: https://www.linkedin.com/in/kristinasubbotina/ YouTube: https://www.youtube.com/@kristinasubbotina Subscribe so you don’t miss a conversation.

What does it really mean to build an extraordinary life? There isn’t one definition of success—or one meaning of life. We create both through the choices we make. Each month, I sit down with founders, creators, investors, artists, and other remarkable people to look beyond what they’ve built and understand who they choose to become, what drives them, and what gives their life meaning. You’ll leave each episode feeling like you’ve genuinely met another human being, expanded your view of what’s possible, and become your own greatest inspiration.

In this episode, Kristina Subbotina sits down with Kate McAndrew, founder of Baukunst, to talk about what really separates great founders from the rest. From the hiring decisions that make or break a startup, to what VCs actually think about founder salaries—this one doesn't hold back. What you'll learn: → How your first hires reveal everything about you as a founder → Why the best investors see potential before the world catches on → What's a reasonable founder salary at pre-seed and seed? ($120K–$225K range breakdown) → The traits that make Kate write a check when no one else will. About Kate McAndrew: Kate is the founder of Baukunst, a pre-seed fund that backs exceptional founders at the earliest stage. She's invested in 100+ companies and is known for betting on people before anyone else sees what she sees. Follow Kristina: https://lexsy.ai Instagram: @kristinasubbotinaesq Linkedin: https://www.linkedin.com/in/kristinasubbotinaesq/ Follow Kate: Instagram: @kate__mcandrew Linkedin: https://www.linkedin.com/in/kateprestonmcandrew/ #startupstory #founders #venturecapital #preseed #hiring #foundersalary #podcast #lexsy

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

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: How to build a targeted investor funnel What makes a pitch deck effective (with real examples) The legal foundation you actually need before you raise 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. 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.

When it comes to raising venture funding, startups have several popular instruments at their disposal: SAFEs, convertible notes, and NVCA documents for priced equity rounds. In this episode, we will focus on SAFEs.

This decision hinges on whether you plan to raise venture funds, how well you understand common legal pitfalls, and how much time you’re willing to invest in the process. In this episode, I compare the options you might consider, to help you decide which one suits your situation best.

Embarking on a startup journey is exhilarating. With numerous critical decisions to make, selecting the right legal structure from the outset is paramount. A Delaware C-Corp is a popular choice for venture-backed startups, and there are several compelling reasons why.

In this episode, you will learn a step-by-step guide to help you come up with a startup name that is legally available for use.

In this episode, I'll be sharing valuable tips on how to create an engaging and well-structured pitch deck for your startup. A great pitch deck is the key to capturing the attention of potential investors and getting the funding you need.

Starting a startup is an exciting journey that must be done correctly from the beginning. Early-stage startups often make legal mistakes that can be costly in the long run. It's crucial for startup founders to be aware of these mistakes and take the necessary steps to avoid them. In this episode, you will learn about five common legal mistakes that startups should avoid.