#15 Josh Constine: Fundraising Tips for Startup Founders

Charles Hudson is the founder and managing partner of Precursor Ventures, where the focus is on backing people at the earliest stage of building a company. Before launching Precursor, he was a partner at Uncork Capital and the co-founder and CEO of Bionic Panda Games. His experience spans both building a startup and investing in founders before their companies have much to show. In this episode, Charles joins Kristina Subbotina to talk about what investors learn after the pitch is over, when founders face difficult decisions, get stuck, or have to find a way forward without an obvious answer. Kristina and Charles go deep on: Why working long hours is not the same as making progress What resourceful founders do when they get stuck The loneliness of being a solo founder and how to build a support network Why a founder’s words carry extra weight with their team What happens when a co-founder leaves with a large stake in the company Vesting, dead equity, and the conversations to have before fundraising The pressure that comes with raising at a high valuation Founder salaries, personal expenses, and how compensation affects runway Building genuine relationships and helping people without expecting something back The conversation goes beyond raising money. Charles shares why being useful to other people matters to him, while Kristina reflects on the personal side of building a company and the people who help make it possible. 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/kristinasubbotinaesq/ YouTube: https://www.youtube.com/channel/UCDtZVgvTcyUyzjvSR_r5CQw Subscribe so you don’t miss a conversation.

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/