Startups Decoded

The fundraising hangover is real. Capital returned in 2025, but investors are now far more selective. Traction, revenue clarity, and capital efficiency matter more than vision decks. In this episode, Roei Samuel joins Andy Walsh to share how he raised $23M+ without giving up board seats, and why that decision shaped Connectd’s growth and governance. We unpack how founders retain leverage in a tighter market, where progress must be measurable and every dollar justified. This conversation explores fundraising as a system, covering negotiation, investor alignment, non-dilutive capital, and the growing role of fractional talent. After exiting RealSport, Roei launched Connectd in 2019. The platform now supports 90+ fractional hires per month, has driven 4× ARR growth for three consecutive years, and has raised $14M+. Andy Walsh 2× exited founder and host of Startups Decoded (500k downloads). A content & production studio for New York’s visionary Builders, Investors, Artists, Musicians, & Creators to amplify their voice & share bold stories. Use the code "Decoded" for 25% off your first booking.

In a world of shifting algorithms and AI noise, winners aren’t the teams with the most tools, but the ones with the best orchestration. Andy Walsh sits down with Brendan Tolleson, CEO of RevPartners and founder of Southbound. Brendan is focused on democratizing Revenue Operations (RevOps), turning it from a B2B luxury into a core growth engine for scaling companies. Aligned with Southbound 2026’s theme, Timeless Principles & Timely Tactics, Brendan explains why 2.7x revenue growth isn’t luck. It’s structured alignment across GTM teams. We unpack the “Friction Tax” slowing startups and how platforms like HubSpot and Clay are reshaping modern revenue systems. We also preview Southbound (April 16, Atlanta), featuring HubSpot CEO Yamini Rangan, Clay cofounder Varun Anand, and NYT bestselling author Donald Miller. Brendan shares why the event is designed as a high-trust environment for revenue leaders building for durability. Andy helps founders sharpen judgment and integrate brand, product, and growth into a clear path to scale. Brendan Tolleson Co-Founder and CEO of RevPartners, an Elite HubSpot Partner in Atlanta. Tolleson led RevPartners to become the fastest-tiering partner in HubSpot history and founded the Southbound conference, focused on predictable revenue growth and sustainable leadership. Access All Areas. Subscribe: Substack Connect: LinkedIn Socials: TikTok || Instagram || X Web: startupsdecoded.com Music Credit “Neptuno” – Phondupe (Album: Onykia ) https://phondupe.bandcamp.com/album/air-conditioning-vol-2 The Studio https://28thandpark.podyx.com/ ​Filmed on location at 28th&Park. A content & production studio for New York’s visionary Builders, Investors, Artists, Musicians, & Creators to amplify their voice & share bold stories. Use the code "Decoded" for 25% off your first booking.

Alisa Cohn has spent decades coaching CEOs through the moments that define their leadership: rapid growth, board pressure, and the quiet isolation of the role. Named the #1 Startup Coach in the World by Thinkers50, Alisa has advised leaders at Venmo, Etsy, and Pfizer. In this episode, we explore why reactive management no longer works and how scaling CEOs must move from firefighting to proactive “North Star” planning as complexity increases. This is a grounded, practical conversation about CEO craft, how to lead with intention when the stakes are high, and the answers aren’t obvious. Based in New York, she advises founders and Fortune 500 executives at companies like IBM, Dell, and The New York Times. A frequent contributor to HBR and Forbes, Alisa is also an angel investor and former startup CFO. A content & production studio for New York’s visionary Builders, Investors, Artists, Musicians, & Creators to amplify their voice & share bold stories. Use the code “Decoded” for 25% off your first booking.

AI is moving fast, but durable businesses aren’t built on models alone. In this episode of Startups Decoded, Andy Walsh sits down with Frank Paz (Partner, Morrison Foerster) and Craig Alberino (Founder & CEO, LangSmart) to unpack what actually makes an AI company defensible and safe, as it scales. Craig brings the operator’s perspective on turning AI experimentation into governed, measurable systems. Frank provides the legal lens, breaking down what is truly protectable and where founders quietly create structural risk around IP, data rights, and open-source models. A content & production studio for New York’s visionary Builders, Investors, Artists, Musicians, & Creators to amplify their voice & share bold stories. Use "Decoded" for 25% off your first booking.

In this episode, Andy Walsh sits with Dr. Denise Bronner, a scientist-turned-strategist who has spent 15 years bridging the gap between the lab bench and the boardroom. As the founder of Empactful Ventures, Denise deconstructs the high-stakes reality of due diligence, transforming it from a “pop quiz” into a strategic mirror for operational maturity. They discuss why founders must stop hiding from their data and start using it to build a narrative that survives the scrutiny of Seed through Series A rounds. From the “Pac-Man effect” of 2026 market consolidation to the emotional toll of M&A “lock-ins,” this is a raw look at what happens when the lights come on in the data room. Chapters 00:00 Lab to Leadership: The Scientist’s Journey 02:43 Bridging Science and Business 08:23 Data Storytelling: Science Meets Strategy 14:21 Understanding Your Investor Audience 17:10 The Reality of Due Diligence 22:48 Mergers & Acquisitions: Survival of the Transparent 28:23 The Founder’s Toll: Empathy in the Exit 40:10 The Pac-Man Effect: 2026 Market Trends “Due diligence isn’t a pop quiz—it’s a mirror. If you organize your truth, pressure helps you; it doesn’t hurt you.” — Denise N. Bronner, Ph.D. Who Should Listen: Founders in regulated spaces (Healthtech/Biotech), Ops leads tasked with data rooms, and investors refining their DD checklists.

Xaver Lehmann built two AI startups, sold one for $60M, and paid the price most founders don’t talk about until it’s too late. Burnout. Identity loss. The quiet crash after the win. In this conversation, we unpack the part of the founder journey that usually gets skipped in pitch decks and podcasts. What actually happens after the exit. Why success can feel emptier than expected. And how building at full speed without designing your life first eventually catches up with you. Xaver shares what he learned the hard way, how burnout reshaped his definition of success, and why he now helps founders build companies without sacrificing their health, relationships, or sense of self. We talk about honest trade-offs, conviction-driven decisions, coaching versus content, and why “more” is rarely the answer founders think it is. This is a conversation for founders chasing big outcomes, and quietly wondering what it’s all costing them. After building and selling an AI company for $60M, he experienced founder burnout firsthand, reshaping how he thinks about success, growth, and leadership. Today, Xaver helps founders build and scale sustainably through coaching, writing, and digital frameworks rooted in lived experience rather than theory. He also invests in early-stage startups and funds with fast, conviction-led decisions. Beyond startups, Xaver supports wildlife conservation in South Africa and early childhood education initiatives in Cape Town. He has been recognised in Forbes 30 Under 30 Europe and DACH. Use the code "Decoded" for 25% off your first booking.

Casey Woo has spent over two decades inside the engine room of real companies, scaling startups as a 6x CFO and 2x COO across SaaS, marketplaces, hardware, eCommerce, and beyond. After walking away from a successful career in public markets, Casey chose the harder path: joining early-stage startups, eating glass, and learning how companies actually get built under pressure. Along the way, he founded the Operators Guild, a global community of 1,200+ elite builders, and FOG Ventures, an operator-led investment platform backing the modern operator and GTM stack. In this conversation, we unpack why generalist operators are becoming the new frontier for founders and investors. We talk about business as both physics and art, why judgment beats specialization early, what separates great operators from average ones, and why VCs increasingly back operator-led companies and platforms. This is an operator-first conversation about craft, execution, and building companies that actually work, without startup theater. Operator 15:31 The Evolution of the Operator Role 16:30 The Impact of Technology on Operators 22:34 Advice for Aspiring Operators 22:42 The Importance of Community in Business 24:23 Learning Through Experience 25:40 Fundamentals of Business Success 27:33 The Role of Human Relationships 28:45 The Operators Guild and Knowledge Sharing 34:31 Introducing Fog Ventures 40:44 Customer Feedback and Product Development Guest Bio Casey Woo is the Founder of the Operators Guild and General Partner at FOG Ventures, a leading operator-led investing platform. A former public markets investor, Casey has spent over 20 years operating inside high-growth companies as a 6x CFO and 2x COO, guiding startups from early-stage through hypergrowth, multiple funding rounds, and pre-IPO. His experience spans software, hardware, marketplaces, eCommerce, supply chain, real estate, and professional communities. Through the Operators Guild, Casey built a global network of more than 1,200 elite operators, the people responsible for scaling some of the fastest-growing companies in tech. Building on that foundation, he launched FOG Ventures, investing alongside operators in the modern operator and GTM software stack.

Mike Adams has spent 30 years doing what most founders underestimate and then desperately need. Connecting people. Lead generation From HP to Apple to Zoom, and across 1,000+ events, Mike has built his career by understanding how trust, reputation, and introductions actually move deals forward. Now, as the founder of introstars, he’s turning referrals into the ultimate scalable lead-gen paradigm and opening up the intro economy to be measurable, trackable, and valuable. In this conversation, we unpack why the best growth no longer comes from cold outreach, why super connectors think differently about value, and how founders can build real leverage by investing in relationships long before they need them. We talk about the “intro economy,” the ethics of monetising connections, what kind of intros make the biggest difference, and why focusing your time on sending referrals to others will actually help your own business. This is a conversation for founders tired of shouting into the void and curious about building growth through trust instead of hacks. Chapters 00:00 Introduction to Networking in the Age of AI 02:02 Mike’s Journey: From Sales to Super Connector 06:10 The Importance of Trust and Vulnerability 11:56 Givers vs. Takers in Networking 17:35 The Role of Introductions in Business Success 24:01 Building Your Personal Brand Through Connections 24:33 Building Trust and Reputation 29:26 The Shift from Cold Outreach to Warm Introductions 37:23 The Role of AI in Networking 44:33 introstars: Connecting People for Mutual Benefit 47:06 Closing Thoughts on Human Connection Mike Adams The founder of introstars, an investor in 20+ startups, and the host of The Super Connectors Podcast. With over three decades in sales and marketing at companies including HP, Apple, and Zoom, Mike has built a reputation as a high-trust connector who understands how relationships really drive business. Through introstars, Mike is building the first platform designed to reward introducers for successful outcomes, turning introductions into a measurable and sustainable growth channel. He’s passionate about helping founders, operators, and investors unlock value through genuine connection rather than transactional networking.

Mike Ma doesn’t invest in decks. He invests in people. As Managing Partner and Head Coach at Sidecut Ventures, Mike works with what he calls “coachable superheroes”, early-stage, mission-driven founders tackling real problems in economic mobility, healthcare, climate, and education. In this conversation, we unpack what it actually means to be coachable as a founder, why most advice fails in practice, and how real progress happens when coaching, capital, and execution collide. Mike shares lessons from the trenches — blending Fortune 500 experience with venture-backed CXO roles, and explains why the best founders don’t just seek answers, they build judgement. We also explore Sidecut’s hands-on approach to venture building, the parallels between adaptive sports coaching and startup leadership, and why helping founders unlock potential often means meeting them exactly where they are, not where the pitch says they should be. This episode is for founders who want fewer platitudes, better questions, and support that actually shows up. Chapters 00:00 Introduction to Impact Investing 02:42 The Thesis of Sidecut Ventures 04:59 Understanding Impact and Returns 07:49 The Case for Climate Investments 10:41 The Duality of Capitalism 13:06 The Role of Ethics in Business 15:47 The Importance of Mission-Driven Founders 18:33 Evaluating Founders Beyond the Surface 23:54 The Foxhole: Partnering with Founders 27:19 The Impact of Investment Models 32:01 The Reality of Foundership 36:50 Understanding the Founder’s Journey 39:43 Evaluating Impact and Market Risks Mike Ma Managing Partner and Head Coach at Sidecut Ventures, where he invests in and coaches early-stage, mission-driven founders working on some of society’s hardest problems. He brings a rare blend of Fortune 500 experience (Bank of America, Vanguard) and venture-backed CXO leadership(including Betterment and Own Up), rolling up his sleeves across product, strategy, and fundraising. Mike believes the best venture outcomes are built through proximity, trust, and real coaching, not performative advice.

Startups Decoded - Presented by Morrison Foerster - mofo.com. Luke Tobin has built seven businesses across hospitality, e-commerce, and agencies. Three exits. One of them: an eight-figure agency sale that started with £100, no funding, and a healthy dose of imposter syndrome. Today, Luke sits at the messy intersection of founders, capital, and exits, backing businesses, fixing broken agency models, and coaching operators to turn self-doubt into fuel instead of friction. In this episode, we get brutally practical on what actually drives profitable growth, why most agencies never become exit-ready, how to price for margin (not ego), and why thinking like a buyer early changes everything. This is an operator conversation, not “founder vibes”. If you want a business that works without you sweating through every Monday, press play. He scaled his most recent agency from £100 to an eight-figure exit in five years with no external funding. Today, he’s the founder of Unusual Group, owner of Tobin Capital, partner at A-Frame Venture Studio, and author of The Success Method newsletter read by 100,000+ founders weekly. Luke advises founders on pricing, operations, hiring, and exits with a relentless focus on building businesses that actually work.

Niluka Kavanagh left Big 4 consulting with a simple question: Can I work for myself, and can I do it from anywhere? That question turned into an experiment, then a business, then ImagineThat, a global club for first-time founders who are trying to build something without losing themselves in the process. We talk about the unsexy realities people don’t plan for: uncertainty, isolation, confidence dips, and the weird moment where you realise “being your own boss” can still mean being owned by customers. Niluka shares the framework she uses with founders to go from “I’ve got skills” to “I’ve got a business,” why you should design your life before you design your model, and why your personal brand is the only asset that survives pivots. This is a conversation for anyone in corporate with a pull toward independence, and anyone early-stage who wants fewer vibes and more clarity. She is the Founder of ImagineThat, the global club for new founders, and the creator of The Modern CEO, a leadership program helping companies evolve into next-generation workplaces. Previously, she worked as a consultant at KPMG with clients like Mastercard, Tesco, and London Stock Exchange, co-founded KPMG FutureThinkers, and led communications for KPMG SheCan. Niluka has spoken at leading universities, including Oxford, Trinity College Dublin, and Edinburgh University, and her work has been featured in The World Financial Review and Cambridge University Press.

Women, BIPOC, and LGBTQIA+ founders still get boxed out of capital, but Katie Dunn has built her angel investing thesis to do the opposite, and she’s doing it with actual reps (29 investments) and serious financial scar tissue (25+ years in banking with $10B financed). Subscribe now In this episode, Katie breaks down what early-stage angels really look for when they say they’re “betting on the founder”, why most cold outreach fails (hint: nobody reads the investor’s thesis), and how underrepresented founders can cut through the noise with clarity, credibility, and a simple story that lands. We also get into the underrated part: investor relationships. Katie explains why your first investors should be your easiest next-round capital, why founders go dark when things get hard (and how that backfires), and how angels often deliver more value than VCs because they actually have time, context, and intent to help. If you’re raising pre-seed/seed, building community, or trying to stop fundraising from eating your soul, this one’s a practical reset. Chapters 00:00 Introduction to Angel Investing 04:18 Katie’s Journey in Finance 06:55 The Importance of Diversity in Funding 10:04 The Role of Immigrants in Startups 12:43 Building Community and Networks 15:30 The Value of Collaboration 18:23 The Role of Angels vs. VCs 21:07 The Importance of Communication 23:45 Finding the Right Investors 26:45 Using Technology to Connect 29:32 Assessing Founders and Their Pitches 32:20 The Art of the Pitch Deck 35:01 Final Thoughts and Resources Katie Dunn An experienced angel investor, board director, and startup advisor investing in underrepresented U.S. founders at the pre-seed and seed stages, primarily in CPG and technology. Through Masthead Strategies, she’s helped founders raise over $30M by combining investor psychology, storytelling, and AI-powered tools. Her portfolio includes Outcast Brands (Blood Monkey Gin, Two Shores Rum), Another Tomorrow, Juliet Wine, WTHN, Forecastr, and Goodword. Katie also serves on the boards of Outcast Brands and the Enthuse Foundation, and advises Fierce Foundry, a femtech venture studio. To receive new posts and support my work, consider becoming a free or paid subscriber.

Startup investing used to be gated, exclusive networks, complex diligence, and full-time fund managers. But what if anyone could build a startup portfolio the same way they’d shop online? In this episode, Cheryl Kellond, serial founder and CEO of Play Money, shares how her platform is democratizing early-stage investing by pairing curated deals from new fund managers with an experience that feels more like shopping than finance. We dive into her journey from launching Bia Sport and Apostrophe (acquired by Centivo) to building Play Money, the new “fantasy league” for startup investing. Expect a candid lesson on why making startup capital more inclusive can reshape who gets funded and who gets to build wealth. She previously founded Apostrophe (Techstars ’17, acquired by Centivo) and Bia Sport (Lemnos ’12), and has launched major products at Adobe, Yahoo, and E*TRADE. Voted Denver’s Most Admired CEO and a 40 Over 40 honoree, she’s passionate about disrupting legacy industries and building founder-friendly ecosystems.

As AI moves from clever tool to “virtual teammate,” nowhere is the shift more real than in finance. In this episode of Startups Decoded, Invoice Butler founder & CEO Mihir Deo joins Andy Walsh to explore what happens when AI agents start doing the unglamorous work humans have always done—chasing invoices, managing cash flow, and acting like your accounts team. We unpack how Invoice Butler is quietly replacing manual accounts receivable workflows with an AI-powered, human-backed agent, what that means for trust, brand, and relationships, and why the future of finance teams is smaller, sharper, and heavily automated, not human-free. With a background in software and product development, Mihir is focused on building AI tools that solve real problems, blending automation with human-first design. Invoice Butler: Invoice Butler blends AI efficiency with human oversight to deliver automated financial processes businesses can actually trust — reducing admin, improving cash flow, and giving founders more time to focus on growth. To receive new posts and support my work, consider becoming a f ree or paid subscriber on Substack.

In this episode, Andy Walsh sits down with Jennifer Lewis, former Founder CEO of queer social app Lex, to unpack the full arc from first fundraise to exit. Jennifer shares what really happens behind the scenes when you’re raising as a queer female founder, how she navigated a co-founder departure mid-fundraise, and why “perfect data rooms” don’t close rounds, relationships, and conviction do. They walk through how she scaled Lex into a beloved LGBTQ+ community, decided to sell to 9count, and protected the mission and culture through the acquisition. If you’re a founder wrestling with fundraising, leadership, or whether to sell, this is a candid, hard-won playbook from someone who’s actually done it. With global experience across Nike, Universal Music, Unilever, and Pepsi, she brings a bold, creative mindset to growth. She’s known for her work in women’s health, LGBTQ+ tech, and community-driven brands, and has led Lex through a major rebrand and exit. Jennifer has won 3 marketing effectiveness awards and over 40 creative awards. Chapters 00:00 Introduction to the Journey of a Founder 01:28 From Advertising to Startups: Jennifer’s Background 04:47 Building Lex: A Personal Mission 09:57 The Importance of Fast Decision-Making 17:19 Navigating Co-Founder Dynamics and Fundraising 21:53 Navigating Leadership and Team Dynamics 25:34 Lessons from Fundraising Challenges 29:12 The Reality of Fundraising for Female Founders 33:16 The Importance of Culture in Acquisitions 36:41 Reflections on the Acquisition Decision 39:59 Exploring New Ventures and Personal Growth About Lex Lex is a social app for LGBTQ+ connection, inspired by vintage personal ads. Originally launched in 2019, it grew into a vibrant digital community for queer expression, with over 1 million downloads and millions of messages sent monthly. In 2024, Lex was acquired by 9count, home to other social platforms like Wink and Summer.

Robert Harary found his first venture deal while in high school detention, and hasn’t looked back since. Today, he sits at the center of the venture ecosystem as both an investor and founder, with a decade-plus obsession for making access to capital more transparent, efficient, and equitable. Robert is the #2 at Evolution VC Partners, where he’s been part of 300+ Culture Tech investments. He runs Timeless Ventures as GP, and has investments in companies like Colossal, Figure AI, and Sindarin. On the founder side, he co-founded DECKO (helping 300+ startups and funds raise $1.2B+) and Raisi (bringing founders in front of 2,000+ investors monthly). Startups Decoded is brought to you by Decko. Contact Decko and use the code word " Decoded " for 20% off. HQ@GetDECKO.com In this conversation, we break down: Why access to capital, not ideas, is the biggest bottleneck for founders How Robert evaluates moonshots (and why he backed OpenAI early) Lessons learned from co-founding DECKO and Weraise Where the venture ecosystem is failing—and what needs to change His belief that democratizing capital will unlock the next wave of transformative companies Chapters 00:00 The Utopian World of Fundraising 06:40 The Evolution of Pitch Decks 13:16 Crafting the Perfect Pitch Deck 20:12 Understanding Investor Psychology 21:59 Cold Outreach and Investor Engagement 23:50 The Three Pillars of Startup Success 26:08 Effective Cold Email Strategies 28:29 The Art of Storytelling in Fundraising 32:40 Investor Marketing as a Relationship Game 39:14 Building Long-Term Investor Relationships Guest Bio Robert Harary is an investor, founder, and venture capitalist obsessed with making capital access more equitable. He is a GP at Timeless Ventures, #2 at Evolution VC Partners (300+ Culture Tech investments), and an angel investor in moonshots, including OpenAI and Colossal. He has co-founded DECKO and Weraise, platforms that have helped 300+ startups and funds raise $1.2B+ from Sequoia, a16z, Accel, YC, and others.

Attorney, entrepreneur, and policy leader Ashley D. Bell is building Redemption Bank, a modern Minority Depository Institution designed to give founders something Silicon Valley rarely does: non-dilutive capital that preserves ownership. With experience spanning the SBA, the White House, and co-founding the National Black Bank Foundation with Dr. Bernice A. King (daughter of Dr. Martin Luther King Jr.), Ashley is fusing community banking, MDI syndication, and fintech infrastructure into a new model of founder finance. In this episode, we break down how to use banks—not just VCs—to extend runway, stabilize cash cycles, and raise without giving up equity. What We Cover Why Redemption Bank: the market gaps MDIs can uniquely fill—credit where venture dollars don’t reach Debt > Dilution (sometimes): picking the right facility (LOC, equipment, AR, revenue-based) for your stage Underwriting that sees your business: when ARR, AR aging, and cohorts matter more than FICO Syndication & Scale: how MDIs partner to increase check sizes without predatory terms Treasury as RevOps: banking tools that speed collections, reduce working-capital drag Signals & Stakeholders: why banking with a mission brand opens doors (enterprise, municipal, talent) Playbook: the 30-day path to “bank-ready” for early-stage companies Chapters 00:00 Introduction to Modern Banking and Treasury 05:42 Ashley Bell's Journey to Redemption Bank 11:08 The Legacy of Dr. Martin Luther King Jr. 16:11 Redemption Bank's Unique Approach to Banking 20:15 The Importance of Role Models in Entrepreneurship 26:36 Reimagining Banking for Modern Founders 34:25 Building Community and Trust in Banking Ashley D. Bell Co-Founder, Chairman & CEO of Redemption Bank. A former SBA Regional Administrator and White House policy advisor, he co-founded the National Black Bank Foundation with Dr. Bernice A. King to channel capital into underserved communities. As an attorney and entrepreneur, he’s focused on building a scalable, tech-forward MDI that expands access to responsible credit for founders and small businesses.

94 percent of sports-science research excludes female physiology. The result? A $10 billion fitness industry that burns women out, leads to injury, and disrupts hormonal health. Lizzy Palmer, Founder and CEO of SyncN, is changing that. SyncN is the first cycle-aware fitness and nutrition platform that personalizes training and nourishment around women’s hormonal rhythms — used by athletes, creators, and founders who want performance without burnout. Sponsored by Cherub In this conversation, Lizzy unpacks: How SyncN helps founders align health with high performance — designing systems for consistency, not guilt. The hidden toll of fundraising — what chronic stress does to founders’ energy, hormones, and focus, and how to lead without self-erasure. Scaling through partnerships — how SyncN’s growth strategy ties mission to distribution through gyms, coaches, and women’s health platforms. What a free 6-month trial on SyncN?* Visit the SyncN Linktree and use the word Decoded” to unlock a Startups Decoded exclusive trial today. (Conditions apply) Disclosure: Andy Walsh serves as an advisor to SyncN. The views expressed here are my own and not influenced by my advisory role. Chapters 00:00 Introduction to Health and Wellness for Founders 01:21 Lizzy’s Journey: From Dance to FemTech 04:37 The Gap in Female Health Research 09:10 Understanding Female Physiology and Hormones 13:16 Training Female Athletes: The Importance of Cycle Awareness 17:57 Self-Compassion and Acceptance in Fitness 22:15 Normalizing Conversations Around Menstruation 25:53 Partnerships and Collaboration in FemTech 28:15 Building Partnerships for Growth 31:20 The Importance of Action in Partnerships 32:52 Leveraging Professional Relationships 36:10 Storytelling and Education in Fitness 39:34 Mental Health and Founder Life 43:50 Navigating Fundraising Challenges 49:45 Introducing Sync In: A New Approach to Women’s Health Guest Bio Lizzy Palmer is the Founder and CEO of SyncN, a cycle-aware fitness and nutrition platform helping women train and fuel in sync with their physiology. A former UX researcher at Meta and Roblox and a professional dancer and fitness coach, Lizzy founded SyncN to close the research gap in women’s health and empower female founders to optimize performance without burnout.

Forget Ivy League. Build Your Own Startup Empire. From Peter Thiel’s Fellowship revolution to building the 1517 Fund, Michael Gibson has made a career out of betting on outsiders. In this episode, he reveals how Thiel’s philosophy, back people, not pedigrees, shaped his mission to fund dropouts, renegades, and deep-tech builders rewriting the future. We unpack how to spot unconventional talent before the world does, why early bets on unproven founders can outperform safe money, and how the next wave of transformative startups won’t emerge from Ivy League halls, but from the edges of the system. Chapters 00:00 From Journalism to Venture Capital: A Unique Journey 07:05 The Dynamics of Founders and VCs 12:50 The Role of Experience in Venture Capital 17:32 Investing in Young Founders: The 1517 Fund 22:56 Backing Renegades: A New Approach to Investment 24:36 The Democratization of Innovation 25:36 Identifying the Renegade Mindset 28:10 The Impact of Educational Systems on Creativity 32:25 Curiosity as a Key Trait 36:20 The Role of Unorthodox Thinking 38:40 Challenging the 10,000 Hour Rule 42:16 The Importance of Unique Perspectives 45:48 Managing Investor Expectations Guest Bio Michael Gibson is the co-founder and general partner of 1517 Fund, a venture firm dedicated to backing dropouts, renegade students, and deep tech scientists who challenge the traditional path. Before starting 1517, he was Vice President of Grants at the Thiel Foundation, where he helped launch and run the Thiel Fellowship, and worked at Thiel Capital. With an academic background in philosophy from Oxford and early editorial roles at places like MIT Technology Review, Michael brings both intellectual depth and contrarian edge to venture capital. At 1517, he’s leading a reformation of how innovation is funded, betting on people with the courage to break from convention.

J aclyn Johnson is a powerhouse entrepreneur, investor, and advocate for women in business. By 35, she had already launched and sold two multimillion-dollar companies, including Create & Cultivate, a first-of-its-kind platform for female entrepreneurs that scaled to eight-figure revenue and partnered with Fortune 500 brands like Amazon, Mastercard, and Microsoft. Now, she’s back with Cherub, a double-sided marketplace designed to bridge the gap between underrepresented founders and democratizing access to category-defining companies. As both an angel investor and advisor, Jaclyn has backed businesses like Away, Live Tinted, and Chillhouse, bringing hard-won experience from her own journey into the founder–funding relationship. Venture Capitalists 08:28 The Role of Angel Advisors 11:23 Building Relationships with Angels 14:15 The Power of Brand Fame 17:25 Cherub’s Mission and Deal Flow 20:07 Educating Angels and Standardizing Investments 23:13 Creating Effective Fundraising Pages 26:12 The Role of Analytics in Fundraising 29:04 Onboarding Founders to Cherub 32:01 Connecting with Angels: Best Practices 35:03 Diversifying the Investment Landscape 37:58 The Future of Angel Investing 40:35 Special Offers for Founders on Cherub Guest Bio Jaclyn Johnson is the founder of Cherub and creator of Create & Cultivate, which she scaled to an eight-figure exit while reshaping how brands and communities support female entrepreneurs. Named a Forbes 30 Under 30 and an Adweek Disruptor, Jaclyn is an angel investor and advisor to companies including Away, Live Tinted, and Chillhouse. She’s dedicated to making capital and community more accessible for underrepresented founders while equipping the next generation of women entrepreneurs to scale.