Behind the Brilliance

THE SHOW In this episode of Behind the Brilliance, entrepreneur and investor Sieva Kozinsky joins the show to share his journey from first-generation immigrant beginnings to co-founding Enduring Ventures, a holding company that acquires and grows businesses for the long game. Sieva opens up about the fear that fueled his early ventures, the lessons learned from failed startups and pivots, and why fundraising can sometimes blind founders to what really matters. We dive deep into the psychology of selling a company, the art of negotiation with founders, and how legacy is built (or destroyed) in the years after an exit. Sieva also reflects on emotional discipline, meditation, and why surrounding yourself with the right five people may be the single most important factor in your growth. This conversation extends beyond building businesses to explore a useful philosophy for building a life you’ll still be proud of twenty years from now. Behind his Brilliance: His mother and grandmother  TOPICS COVERED How Sieva’s immigrant upbringing shaped his resilience Pivoting from pre-med to entrepreneurship The pivotal college class that changed everything Why early failures were his best education Lessons from building and pivoting StudySoup Bootstrapping vs. raising venture capital (and why he regrets fundraising early) The psychology of fear as a driver in entrepreneurship Emotional discipline: responding instead of reacting The role of meditation in business and life The dangers of selling to universities (and what that taught him) Negotiating with founders who are selling their life’s work Why most entrepreneurs misunderstand exits and valuations The holding company model and why it’s different from private equity How to minimize regret when selling a business Finding the right cofounder and what to look for beyond skills The importance of discomfort in building a meaningful life Why you become the average of the five people closest to you Seeking serendipity and building networks through curiosity

THE SHOW What happens when you build the company of your dreams, only to realize the dream came with tradeoffs you didn’t see coming? In this candid conversation, Rand Fishkin — cofounder of Moz and SparkToro — shares the pivotal moments that shaped his career: turning a $39 side experiment into a multimillion-dollar SaaS, raising venture capital for the wrong reasons, walking away from a $40M acquisition offer, and rebuilding his identity after leaving the company he founded. Along the way, Rand unpacks the philosophy he lives by now: designing work around the life you want, not the other way around. You’ll learn why audience-first growth changes everything, how “dark social” can reshape your marketing strategy, and why the best companies aren’t built on hustle, but on thoughtful design. If you’ve ever wrestled with status anxiety, questioned the pace you’re working at, or wondered what it would look like to run a business without burning yourself out, this episode will give you fresh perspectives and actionable ideas for building something that lasts — without losing yourself in the process. BEHIND HIS BRILLIANCE: Empathy TOPICS COVERED  ·  Status is a poor reason to raise capital – chasing external validation through VC can distort decision-making and undermine founder well-being. ·  Audience-first beats product-first – building trust and reach before launching a product creates built-in marketing and faster adoption. ·  Design trumps grind – thoughtful business and life design leads to better decisions, fewer hours, and more sustainable success than relentless hustle. ·  Identity can’t be tied to one venture – detaching self-worth from your company enables resilience when endings or pivots come. ·  Opportunity cost is real – turning down an offer (even for the “right” reasons at the time) can shape the trajectory of both the business and your personal life. ·  Measure what matters, not what’s easy – “dark social” means a lot of word-of-mouth and share-driven traffic won’t show up in analytics the way you expect. ·  Life design is part of business design – integrating personal goals, health, and relationships into work choices leads to richer, more fulfilling outcomes. And much more!  Get the Show Notes here.  

Dr. Rae Wynn-Grant is a wildlife ecologist, storyteller, and nature show host whose path to success defies every traditional metric of merit. In this candid conversation, Rae shares how she went from struggling in math and science classes to earning a PhD and becoming a leading voice in wildlife conservation. We explore the pivotal role that belief, representation, and access played in shaping her journey from her first exposure to nature through television, to a transformative study abroad trip to Kenya, to an unexpected pivot from lions to black bears. Rae also opens up about hitting emotional rock bottom in her 30s, the identity crisis that followed, and how she rebuilt her life with honesty, humility, and hope. This episode is a testament to what’s possible when we follow our passion, even when our performance or our path doesn’t fit the mold. Behind her brilliance:  Taking a non-traditional approach TOPICS COVERED:  Why passion trumps performance - How to pursue your calling even when traditional metrics suggest you're "not qualified" The representation breakthrough - Why seeing yourself reflected in expertise positions transforms what feels possible Navigating productive discomfort - How to embrace stretching experiences that feel uncomfortable but lead to growth Identity crisis as catalyst - Using rock bottom moments as launching pads for authentic reinvention The marriage blueprint trap - Why relationships fail when one person brings a pre-drawn life plan instead of co-creating Accountability without excuses - The liberation that comes from owning your choices and their consequences Nontraditional paths to traditional success - How to thrive by refusing to fit conventional molds while still achieving recognized accomplishments Environmental justice reframed - Why urban communities often care more about environmental issues than rural ones (despite stereotypes) The privilege of starting over - Understanding what safety nets make radical life changes possible Choosing authenticity over expectations - The courage required to disappoint others in service of being true to yourself

THE SHOW Most of us are running on autopilot, checking boxes, chasing goals, and pushing toward some imagined finish line without stopping to ask if this is how we really want to spend our lives. In this conversation, Jodi Wellman, author of You Only Die Once and founder of the 4,000 Mondays framework, makes the case for using mortality as a tool, not a threat. She shares why contemplating the end of life can snap us out of numb routines and guide us toward choices that create more vitality, meaning, and joy right now. We talk about why achievement can feel hollow, how to spot the “dead zones” in your life, and the surprising power of small changes to make life feel bigger. Whether you have been wondering if there is more to life than your to do list or you just want to feel more alive in your everyday routines, this conversation is a reminder that your Mondays are numbered so make them count. Behind her brilliance: Love and the Grim Reaper    TOPICS COVERED ·  Mortality as Motivation: Facing the reality of death as a way to live more fully, not morbidly. ·  4,000 Mondays Concept: Using your finite number of Mondays as a framing device to clarify what matters. ·  Vitality + Meaning = Fulfillment: Living wider (fun, novelty, aliveness) and deeper (purpose, connection). ·  The Hedonic Treadmill: The idea that high achievers constantly move the goalpost and lose perspective on satisfaction. ·  Experimentation as a Way of Life: “You don’t have to detonate, you can dabble.” ·  Regret Minimization Framework: Inspired by Jeff Bezos and reframed here as: “What would you regret not doing?” ·  Role of Rituals and Values: Structuring life around recurring rituals and clearly defined personal values. ·  Self-Compassion and Inner Talk: The importance of being kind to yourself in the pursuit of growth. ·  Redefining Success and Retirement: Moving from performance-based identities to interest-based living. ·  Comparison and Individual Journeys: Why your life design has to be uniquely yours, and how social media distorts that.  

Elaine Pofeldt, former Fortune Small Business editor, uncovered a hidden economy of one-person businesses quietly earning 7 figures and spent years interviewing the entrepreneurs behind them. In this conversation, she reveals the surprising industries dominating this space, why professional services often outperform tech, and the frameworks that actually work for building sustainable solo wealth. From starting smart while keeping your day job to using AI as your secret weapon, Elaine breaks down the real strategies behind million-dollar one-person businesses. No hype, no hustle culture required. Plus: why health and boundaries aren’t “extras” but essential business infrastructure, and how to design a career that serves your life instead of consuming it. Essential listening for anyone who wants financial freedom without chasing passive income or playing the venture capital game. Behind Her Brilliance: Family   TOPICS COVERED Elaine’s journey from fiction writing to journalism   The evolution of business journalism and rise of entrepreneurship in the public imagination   How AI and automation empower solo business owners   The origin story of The Million Dollar, One Person Business   Why peer learning and relatable case studies matter   Common traits among successful solo entrepreneurs   The emotional and mental stamina required to succeed independently   The role of physical health, boundaries, and self-awareness in entrepreneurial success   How older professionals and people with disabilities are reshaping the business landscape   Flexible business models that support life design   Building walk-away money and choosing clients wisely   The underestimated power of tools like planners, automation apps, and AI assistants   Lifestyle design, digital nomadism, and work-from-anywhere strategies  

Tal Ben-Shahar, a Harvard-trained psychologist and bestselling author, shares insights on navigating the often-misunderstood journey to happiness. He discusses the pitfalls of achievement addiction and how embracing one's negative emotions can lead to genuine fulfillment. The impact of social media on perfectionism is explored, along with the significance of curiosity in emotional well-being. Ben-Shahar also offers practical advice for parenting and leadership in a post-pandemic world, emphasizing the importance of self-compassion and real connections.

SUMMARY Anne-Laure Le Cunff, founder of Ness Labs and author of Tiny Experiments: How to Live Freely in a Goal-Obsessed World, joins Lisa to reveal her unconventional career journey from Google engineer to startup founder to neuroscience student to successful entrepreneur with Ness Labs. Growing up outside Paris with parents who prioritized financial security, she landed a dream job at Google with the status and paycheck that signaled success. But she soon realized that the ladder she was climbing was leaning against the wrong wall. This conversation explores cognitive scripts that keep us stuck, the importance of experimentation over rigid goal-setting, navigating uncertainty, and designing a life aligned with internal rather than just external metrics of success. Anne-Laure shares insights on managing different types of burnout, the psychology of major transitions, and how she uses tools like journaling and AI to support her work and decision-making. Behind her brilliance: Curiosity Say hi to Anne-Laure on X/Twitter: @neuranne TOPICS COVERED Breaking free from cognitive scripts The problem with traditional goal-setting Building an experimental mindset Why “feeling lost” is the price we pay for having freedom Career transitions and identity beyond job titles Navigating impostor syndrome Burnout (including when you love your work!) Redefining success using internal vs. external criteria Managing time and energy without a corporate structure Redefining the relationship between time, money, and personal values Building a business organically and leveraging momentum Using AI as a creative thinking partner Growing up with multicultural influences Examining default coping mechanisms like alcohol (and Anne-Laure’s journey to sobriety) Letting curiosity lead personal and professional decisions And much more!

THE SHOW Ahad Khan, CEO of Kajabi, shares how his Midwestern roots shaped his approach to building software for "regular people," his experiences navigating investment banking, startup acquisitions, and the creator economy. Ahad reveals his philosophy on people-first decision making, the power of work-life integration over balance, and why choosing character over compensation has been the thread connecting every major career move. The conversation explores the evolution of the creator economy, the challenges of remote leadership, and practical strategies for staying present as both a CEO and father of three. Behind His Brilliance: Immigrant parents who modeled hard work, presence, and the courage to build a life around what matters most Get the show notes here.  TOPICS COVERED ·       Why pivoting early (or late) is worth it ·       Growing up in Northeast Ohio and the "regular people" advantage in tech ·       Why his father said "you can be any kind of engineer you want" ·       Investment banking culture in Chicago vs. New York stereotypes ·       The power of choosing people over compensation in career decisions ·       Early startup lessons and the importance of founder character ·       MileIQ: solving real problems for people who drive for work ·       Navigating Microsoft's acquisition and cultural transformation under Satya Nadella ·       The bootstrap advantage: how 9 years without funding built Kajabi differently ·       Creator economy vs. entertainment: building sustainable businesses ·       The $6 billion paid out to Kajabi creators and the subscription vs. take-rate model ·       Transitioning from CFO to CEO and the weight of leadership ·       Work-life integration: taking kids to school as non-negotiable priority ·       Remote leadership strategies and building a documentation culture ·       Why human customer support beats automation every time ·       The hardest part of being CEO: communicating the "why" behind decisions ·       Redefining success: involved parent, good husband, teammates who like you   Behind Your Brilliance: What's one decision you could make this week to better align your work life with your core values?

THE SHOW In this episode of Behind the Brilliance, Dr. Ellen Hendriksen, clinical psychologist and author of How to Be Enough, joins the show to explore the nuances of perfectionism—from its seductive productivity perks to its hidden emotional costs. She shares her own journey from high-achieving student to recovering perfectionist, breaks down the psychology of procrastination and emotional suppression, and offers practical strategies for redefining self-worth, navigating achievement hangovers, and aligning with intrinsic values. The conversation also touches on the loneliness epidemic, community building, and how shifting from "have to" to "choose to" can transform how we show up in our lives.   Behind her Brilliance: Investing in what connects us to others instead of what sets us apart   TOPICS COVERED Why pivoting early (or late) is worth it A new definition of perfectionism—and why it’s a trap The two pillars of maladaptive perfectionism: overvaluation and rigid standards The myth of emotional perfectionism Rules vs. values (and how rules often masquerade as values) Demand sensitivity and the burden of internal expectations The achievement hangover: chasing the next milestone without fulfillment The difference between goals and values Procrastination as anxiety in disguise Visualizing your future self to beat avoidance Practical tools to embrace imperfection and act anyway Community, connection, and healing the loneliness epidemic The value of empathy in creative and professional work

Lisa summarizes Season 14, Defying the Odds, with reflections on the strategies shared and helpful recaps. 240 – Dr. Andrew Newberg 241 – Cin Fabre 242 – Tyler Denk 243 – Jim Fielding 244 – Dr. Valerie Daniels-Carter 245 – Simone Stolzoff 246 – Thomas Wedell-Wedellsborg 247 – Andrew Barnes 248 – Jamila Souffrant 249 – Kevin Kelly   Subscribe to CUE at BehindtheBrilliance.com to be the first to know when the new season streams.