NEXT with Michael Sonnenfeldt

Host Michael Sonnenfeldt sits down with national security entrepreneur and investor Peggy Steyer, Co-Founder and Managing Partner of Razor’s Edge Ventures. A pioneer in defense, cyber, space, and AI investing, Peggy previously built Blackbird Technologies into a premier provider of mission-critical solutions for intelligence, defense, and law enforcement customers before its record-setting acquisition by Raytheon. She later co-founded Raven Wing, which was acquired by Boeing, and went on to launch Razor’s Edge, generating more than $1 billion in shareholder returns over the past five years.Peggy shares candid insights on building companies where lives are on the line, transitioning from operator to investor, and creating high-performance teams drawn from both special operations and elite technologists. Key topics include scaling in national security markets, Blue Ocean strategy vs. crowded competition, the proper role of boards and investors, asymmetric warfare and emerging threats, AI and geopolitical risk, founder resilience, partnership dynamics, and balancing mission critical leadership with family life and long-term purpose.Giving Moment:Join this season's philanthropic giving moment where every donation made in Q1 2026 will be matched dollar-for-dollar up to $100 per gift ($10,000 per organization). Donate at www.muus.com/giving.Topics:00:01:48 – Childhood, Navy upbringing, and early influences00:03:38 – The layoff that sparked her entrepreneurial path00:05:18 – Motivations beyond money00:06:04 – Founding Blackbird & solving national security tech problems00:09:10 – Women in national security & leadership advice00:14:56 – The role of spouses and support systems00:18:27 – Building, scaling, and exiting Blackbird & Raven Wing00:23:33 – Transition from CEO to venture investor00:26:41 – The proper role of a board vs. CEO00:30:52 – Razor’s Edge strategy & Blue Ocean investing00:35:33 – Responsibility in national security work00:38:14 – Geopolitics, deterrence & asymmetric threats00:42:19 – AI, China, and the future of technology00:45:22 – Investment mistakes & lessons learned00:46:52 – Advice for young entrepreneurs00:49:20 – Books, leadership insights & closingMentioned:TIGER 21 is the premier peer membership organization for ultra-successful entrepreneurs, investors, and executives. Through confidential forums and shared experience, members gain perspective on wealth, leadership, and life beyond success.Peggy’s book recommendation - Team of Rivals: The Political Genius of Abraham Lincoln by Doris Kearns GoodwinFollow and Connect:Peggy Styer | WebsiteMichael Sonnenfeldt |  Website | next@muus.com

On this episode of NEXT, Alex Bean—Co-founder of Divvy and Managing Partner of Tandem Ventures—reflects on what comes after entrepreneurial success. Drawing on his experience building a category-defining fintech company and exiting for $2.5B, Alex shares candid insights on founder identity, co-founder dynamics, and the emotional and relational challenges that often follow a liquidity event. He breaks down what product-market fit really feels like, how successful founder partnerships are structured, and why understanding your role—can be decisive in scaling a company quickly and sustainably.The conversation then shifts to wealth, family, and legacy. Alex explores how money reshapes relationships, why shared assets and minority ownership can quietly introduce long-term risk, and how families can unintentionally trade closeness for complexity. He also introduces Factory for Good, his framework and new social enterprise for helping families build intentional giving practices by applying clarity, discipline, and measurement to philanthropy. This episode is essential listening for founders, investors, and families navigating life after success—especially those thinking deeply about purpose, stewardship, and how to turn financial outcomes into lasting, positive impact.Giving Moment:Join this season's philanthropic giving moment where every donation made in Q1 2026 will be matched dollar-for-dollar up to $100 per gift ($10,000 per organization). Donate at ⁠⁠www.muus.com/giving.Topics:(02:00) – Growing up in Redmond during Microsoft’s rise(03:30) – Early startups, failure, and learning to take risks(05:30) – Are entrepreneurs born or made? The mindset of failure(07:30) – Lessons from three generations of family business(09:30) – Wealth, loneliness, and identity after success(11:30) – Why money doesn’t solve purpose(13:00) – The origin of Divvy and taking an 80% pay cut(15:00) – Product-market fit and hypergrowth(17:00) – Founder roles, trust, and partnership dynamics(19:00) – The pressure and toll of scaling fast(20:00) – Giving break: Understood.org(21:00) – Life after exit: loss of structure and identity(23:00) – The Factory for Good concept explained(26:00) – Builders vs. operators and finding what gives energy(28:30) – Knowing when it’s time to leave a business(30:30) – Raising independent children after success(33:30) – Stewardship, inheritance, and shared-asset risks(37:30) – Minority discounts and loss of control(40:00) – Teaching children the purpose of wealth(42:30) – Microsoft vs. Gates Foundation: value vs. impact(46:00) – Giving at scale and impacting lives meaningfully(49:00) – $5,000 miracles and tactical philanthropy(51:30) – Advice for Alex’s kids and family values(52:30) – Tip jar: Open by Andre Agassi + Paladin app(53:30) – Where to find Alex and closingMentioned: ⁠TIGER 21 ⁠⁠ is the premier peer membership organization for ultra-successful entrepreneurs, investors, and executives. Through confidential forums and shared experience, members gain perspective on wealth, leadership, and life beyond success.Alex's book recommendation: Open by Andre AgassiAlex's app recommendation: PaladinFactory For Good: WebsiteFollow and Connect:Alex Bean | ⁠⁠Website⁠Michael Sonnenfeldt | ⁠⁠LinkedIn⁠⁠ | Email: michael@muus.comNEXT with Michael Sonnenfeldt Podcast | ⁠⁠YouTube⁠⁠ | ⁠⁠Website

On Episode 2 of NEXT, Omar Simmons—Managing Partner of Exaltare Capital Partners and former ECP CEO of Planet Fitness—dives deep into the realities of hiring, leadership, and risk in the franchising business. Drawing on his experience scaling Planet Fitness from 15 to over 100 locations and exiting via selling majority share to an institutional partner. He shares practical insights on interviewing for resilience, onboarding employees, reducing turnover, and building operating systems that work at scale across decentralized teams.The conversation also explores how experienced operators think about risk—not as volatility on a spreadsheet, but as something shaped by judgment, pattern recognition, and execution. Omar breaks down what makes franchising a uniquely powerful business model, how centralized learning and local ownership combine to drive performance, and how leaders de-risk growth through planning, diversification, and discipline. This episode is essential listening for founders, operators, investors, and franchise executives focused on scaling businesses, building durable teams, and making better decisions under uncertainty.Giving Moment:Join this season's philanthropic giving moment where every donation made in Q1 2026 will be matched dollar-for-dollar up to $100 per gift ($10,000 per organization). Donate at ⁠www.muus.com/giving.Topics:(01:55) — Growing up in inner-city Boston: family, housing, and early lessons(03:55) — The role of love, community, and sports in shaping resilience(04:46) — Cold-calling Princeton: betting on yourself early(06:55) — Mentorship, peer groups, and learning without a traditional playbook(09:45) — Paying mentorship forward: coaching, leadership, and legacy(12:05) — What makes franchising such a powerful business model(15:00) — Centralized learning vs. decentralized ownership in franchises(16:10) — Can grit be taught? How Omar evaluates drive and adversity(18:40) — Hiring, leadership limits, and knowing when people won’t change(19:05) — Spotlight on Understood.org and supporting learning differences(20:55) — The “gold standard” franchisors and why fit matters more than brand(24:00) — Risk in the eye of the beholder: investing, intuition, and expertise(27:10) — COVID, concentration risk, and surviving extreme uncertainty(28:30) — Employee engagement, retention, and why caring actually scales(31:00) — Scaling Planet Fitness from 15 to 100+ locations(33:00) — Selling the business: timing, COVID shock, and liquidity decisions(35:30) — Life after the exit: identity, rhythm, and redefining purpose(38:00) — The Ascension Franchise Initiative: expanding ownership access(41:30) — Measuring success through ownership and wealth creation(44:00) — Racism, progress, and hope in America today(47:00) — Profit vs. purpose: why it’s a false choice(49:00) — Gratitude, giving back, and generational responsibility(50:20) — What’s next for Omar in this stage of life(51:30) — Advice to his younger self(52:30) — Tip jar: spiritual practice, history, and recommended readsMentioned:⁠TIGER 21 ⁠ is the premier peer membership organization for ultra-successful entrepreneurs, investors, and executives. Through confidential forums and shared experience, members gain perspective on wealth, leadership, and life beyond success.Omar's podcast recommendation: The Rest is HistoryFranchise Ascension Initiative: WebsiteFollow and Connect:Omar Simmons | ⁠WebsiteMichael Sonnenfeldt | ⁠LinkedIn⁠ | Email: michael@muus.comNEXT with Michael Sonnenfeldt Podcast | ⁠YouTube⁠ | ⁠Website

Host Michael Sonnenfeldt kicks off Season 2 with creator economy pioneer Mae Karwowski Founder and CEO of Obviously, a leading influencer marketing agency working with global brands including Amazon, Ford, Ulta Beauty, and Coca-Cola. Mae built Obviously before influencer marketing became mainstream, helping define how brands partner with creators at scale across platforms like Instagram, TikTok, and YouTube.In 2023, Mae led Obviously through a successful acquisition by WPP, one of the world’s largest advertising and marketing companies, and continues to serve as CEO today. She shares practical insights on entrepreneurship, scaling a founder-led business, and knowing when to sell a company. Key topics include influencer marketing strategy, pricing in emerging industries, founder partnerships, mentorship, leadership after acquisition, and balancing high-growth leadership with family, motherhood, and long-term purpose.Giving Moment:Join this season's philanthropic giving moment where every donation made in Q1 2026 will be matched dollar-for-dollar up to $100 per gift ($10,000 per organization). Donate at www.muus.com/giving.Topics:(00:00) Season 2 introduction of Next(00:31) Introduction to Mae and Obviously(01:00) Building an influencer marketing company before the category existed(02:27) What influencer marketing really is—and why it matters(03:13) Industry rankings, scale, and market evolution(03:30) Early life, entrepreneurship, and risk-taking(04:28) Lessons from childhood sports and being the underdog(05:30) Choosing yourself and building grit as a daily practice(07:00) Raising children to challenge convention(08:00) The “nausea test” for personal and professional growth(09:30) Delayed gratification and surviving near-quitting moments(11:30) Family influence: lessons from Mae’s parents(13:30) Opportunity, timing, and seeing what others miss(15:30) Rare books, pricing power, and creating value from nothing(18:00) Liberal arts, philosophy, and the future of human intelligence(20:30) Avoiding comparison and building community(23:00) Mentorship—both receiving and giving it back(25:30) Advising women preparing to sell their companies(26:30) Building trust with a remote co-founder(28:30) Choosing the right business partner(30:30) When founder relationships fracture(32:00) Leadership, motherhood, and building real support systems(34:30) Balancing family, business, and long-term priorities(37:00) Marriage, entrepreneurship, and intentional communication(40:30) From startup CEO to WPP leadership(42:00) Growth vs. profitability after acquisition(44:00) Letting go after selling: the bank account moment(46:00) Pressing forward with new resources and perspectives(48:00) Influencer marketing and politics(49:30) The first TikTok election and cultural shifts(51:00) Why influencer marketing is fundamentally different(52:30) The moment Mae knew it was time to sell(54:00) What she wishes she’d known at the beginning(55:00) Advice she hopes her children will take(56:00) Tip JarMentioned:TIGER 21 is the premier peer membership organization for ultra-successful entrepreneurs, investors, and executives. Through confidential forums and shared experience, members gain perspective on wealth, leadership, and life beyond success.The Hard Thing About Hard Things — Ben HorowitzMae's favorite perfume —1969 by Histoire de Parfums and Issara by DusitaFollow and Connect:Mae Karwowski | WebsiteMichael Sonnenfeldt | LinkedIn | michael@muus.comNEXT with Michael Sonnenfeldt Podcast | YouTube | Website

Season 2 of NEXT with Michael Sonnenfeldt invites you ringside to conversations exploring life after major success – the prism where wealth, purpose, and legacy converge. Through intimate discussions with leading entrepreneurs and investors , uncover the playbooks for navigating life’s next phase. From managing wealth and identity to creating impact that endures. Learn from real stories of reinvention, purpose, and legacy from leaders who’ve been there.Disclaimer: This podcast is for informational and entertainment purposes only and does not constitute financial advice, investment guidance, or recommendations to buy or sell any asset. Neither the host, team, TIGER 21, nor their affiliates guarantee financial outcomes or the accuracy of any information provided by guests or hosts. Listeners are responsible for their own research and decisions regarding any financialmatters. Additionally, companies mentioned on this podcast may be owned in whole or in part by hosts, guests or team members.NEXT podcast website: www.muus.com/podcastTIGER 21 website: www.tiger21.comNEXT YouTube channel: www.youtube.com/@nextwithmws