What does it really mean to “have it all”? In this deeply honest conversation, Olivia sits down with longtime mentor and design leader Andrei Herasimchuk to unpack the realities of career growth, motherhood, and intentional tradeoffs. They revisit advice given years earlier, reflect on how it landed differently before and after kids, and explore how modern tools, entrepreneurship, and AI are reshaping what’s possible for women today.

This episode is not about perfection or hustle. It’s about clarity, timing, and designing a life with fewer regrets and more intention.

Key Takeaways

• Why “you can do both” often ignores the real cost of doing everything at once
• The career inflection point many women hit between ages 27–34
• How unexamined choices can quietly pause career momentum
• Why being specific about what you want is an act of self-kindness
• How modern tools and entrepreneurship create new paths outside traditional corporate systems
• What the future of design work looks like in an AI-driven world

Episode Timeline
00:00 – Reconnecting after a decade
A personal reunion sets the stage for a reflective, honest conversation.

03:00 – The advice that sparked controversy
 “Have your kids before your career or after.” What was really meant and why it felt so confronting.

07:00 – The reality of doing both
 Why it’s possible, but far harder than most people admit.

12:00 – The invisible career pause
 How choosing family often comes with long-term professional tradeoffs.

18:00 – Building work around life, not the other way around
 Leaving big tech and reclaiming time, creativity, and agency.

24:00 – Parenting as people-watching
 Letting kids become themselves and why that’s the most fascinating part.

32:00 – AI, design, and the future of creative work
 Why design roles are splitting and where human judgment still matters.

45:00 – Intentionality over overwhelm
 Planning life in chapters instead of trying to win everything at once.

Call to Action

If this episode resonated, subscribe to the podcast and share it with a friend navigating career, family, or creative transitions. Leaving a review helps more people find these conversations.

In this episode of Building Iconic, Olivia sits down with designer, entrepreneur, author, and Second Harvest co-founder Richard Banfield for a deeply human conversation about identity, reinvention, and the courageous work of becoming yourself again after life-changing events.
 Richard shares how grief, community, creative expression, and design thinking shaped his newest chapter, and why he believes the second half of life can be more vibrant, collaborative, and purpose-driven than the first.
This is a conversation about self-love, rebuilding, and what happens when you create the space—literally and emotionally—for transformation.

Key Discussion Topics
1. Richard’s Origin Story and the Thread of “Making”
Richard describes growing up surrounded by entrepreneurs and artists, building businesses as a teen, and discovering the “magic” of turning an idea into something real. This maker identity becomes the throughline of his entire life.

2. Grief, Community, and the Birth of Second Harvest
After losing his wife to cancer and then losing their business to COVID, Richard’s friends created a 10-day sanctuary for him—time in nature, biking, meals together, no fixing. This became the inspiration for Second Harvest, a series of retreats and summits designed to help people navigate moments of profound life transition.

3. Why Midlife Should Be the Start of Something Bigger
Richard challenges the outdated “Golden Girls at 55” narrative and argues that modern midlife is about reinvention, not retirement. People want their second half to be richer, more intentional, and more aligned with who they’re becoming.

4. Community as Catalyst: How Retreats Spark Unexpected Alliances
He shares stories of strangers becoming collaborators—including a medium and an evangelical fund manager who now co-author a book together. The retreats are designed with ambiguity and openness so serendipity can do its work.

5. Self-Love as the Foundation for Everything Else
One of Richard’s most surprising recent learnings: self-love changed everything downstream—from how he fathers to how he leads to how he creates. You can’t serve others when your cup is empty.

6. Design Thinking as a Life Framework
Richard reframes design sprints as a method for life design, not just product design. He explains how thin-slice experiments, good questions, and iterative testing help people shape identity, purpose, and next steps—especially during personal reinvention.

7. The Importance of Silence, Space, and Boredom
Whether it’s long walks, chopping wood, or no-screen Sundays, Richard believes inspiration requires empty space. Silence is what makes the “notes” of life audible.

8. Risk, Courage, and Creating Something New
Richard encourages listeners to take risks, ignore the pull toward “average,” and embrace a bit of healthy delusion. Everything meaningful requires courage, and comfort is “a slow death.”


Memorable Quote
“Comfort is slow death. If you want to feel alive, you have to take risks, be willing to be disliked, and create something meaningful—even if it feels a little crazy.” – Richard Banfield

🎧 Tune in now and dive deeper into Richard’s story, Second Harvest, and the art of designing your next chapter.

In this episode, Olivia sits down with Gabriella Hachem, co-founder of Dessn, the platform redefining how product teams build by anchoring design directly inside production. They explore what it really means to build something iconic-and why solving foundational problems requires deep conviction, thoughtful craft, and the willingness to be a little delusional.

Gabriella explains how Dessn eliminates the decades-long gap between design intent and engineering output by connecting directly to the codebase and creating a design environment that operates inside it. Rather than bringing production into design (like most tools attempt), Dessn starts at the code and builds upward, allowing designers and PMs to contribute meaningfully without needing to code.

They discuss collapsing roles, avoiding decision fatigue, democratizing access to higher-leverage work, and why future teams will operate as “builders” rather than siloed specialists. Gabriella also speaks candidly about the emotional side of scaling a company, choosing to work only with truly exceptional people, and how to maintain joy and humanity while solving brutally hard problems.

🔑 KEY TAKEAWAYS
Dessn starts from your codebase, creating a design environment inside production rather than abstracting away from it.

Most competitors start outside and work backward - Dessn reverses that.

AI removes low-leverage work, leaving craft, taste, and originality as competitive edges.

Great design isn’t decoration - it’s how humans experience trust.

Conviction is non-negotiable. You sometimes have to be “delusionally certain” before anyone else sees it.

Roles will begin to collapse as access to product environments expands - future teams are “builders.”

True innovation requires not just big vision, but consistent delivery.

Subscribe to Building Iconic for more candid conversations with founders who are redefining what it means to build things that last.

Alison Rand has shaped some of the most respected design cultures in tech—from Frog and Hot Studio to SAP—before turning her focus to the intersection of design, humanity, and midlife. Her new book, Finding Sense and Purpose in Design Leadership (MIT Press), explores how personal history, emotion, and cultural systems shape the way we build and lead. She’s also the co-founder of 40|50, a platform and community that brings women together through story, health, and shared experience.

In this episode, Olivia and Alison discuss the invisible systems behind good design and what happens when those systems fail. They examine how leaders can rebuild culture from the inside out and how women can reclaim power in spaces that were never designed for them.

Key Topics

• The evolution of design from visual polish to organizational transformation
  
  
• How to listen, lead, and identify the “signal amid the noise”
  
  
• Why women in midlife need new models of community and belonging
  
  
• The danger of “culture fit” and what inclusion really requires
  
  
• Lessons from Alison’s book on organic intelligence and lived experience
  
  
• How nature and somatic practice inform her work and creativity
  
  

It’s a deeply human conversation about leadership, identity, and finding purpose beyond performance. Alison’s clarity and warmth cut through the noise, offering a grounded view of what it means to build something iconic—without losing yourself in the process.

In this powerful conversation, Olivia sits down with Olympian and coach Mechelle Freeman—three-time Olympic gold medalist and founder of MF 100—to unpack the mindset, faith, and systems that have defined her journey from athlete to visionary leader. Mechelle shares how she turned moments of setback into full-circle triumphs, from dropping the baton in Beijing to leading Team USA’s women’s relays to gold in Tokyo and Paris.

Listeners will hear how Mechelle applies her 100% intensity philosophy not only to sport but to parenting, entrepreneurship, and personal growth. She opens up about faith, family, grief, resilience, and what it means to “keep moving” when the path ahead isn’t certain.

In This Episode

• How Mechelle transformed Olympic heartbreak into coaching redemption.
• The story behind MF 100 and its philosophy of living at full intensity.
• Her FAST framework: Focus, Action, Systems, and Trust.
• How to feed your faith and starve your distractions.
• Building world-class teams—on the track and in business.
• Parenting with purpose and instilling high-performance values in your kids.
• The power of doing it afraid, and why progress means moving even when you’re tired.
• What it takes to go from athlete to architect of legacy.

Key Quotes

Mechelle Freeman is an Olympic gold medalist turned national team coach who led Team USA’s women’s relays to record-breaking victories. Today, she’s the founder of MF 100, a human performance brand built on faith, focus, and 100% commitment. Her upcoming book and programs help athletes, entrepreneurs, and high performers build resilience, discipline, and purpose-driven success.

Thank you for listening to Building Iconic. If today’s conversation with Olympian Mechelle Freeman inspired you, share the episode with a friend, leave a review, and subscribe wherever you get your podcasts.

Special thanks to Wayfare Recording for their work on this episode.

Follow us for more conversations with leaders, creators, and visionaries who are building what lasts.

In this episode of Building Iconic, Olivia sits down with Josh Lowman, founder and CEO of Gold Front, a San Francisco–based category design studio behind some of the world’s most forward-thinking brands.

Josh shares how he turned fear into action—launching Gold Front in his forties after years of hesitation—and why the agency’s hybrid approach to strategy and creativity has made it one of the most respected in the tech world.

This conversation explores the tension between ambition and authenticity, the discipline behind creative success, and the evolving role of AI in the agency landscape.

You’ll hear:

• How Josh overcame fear and finally started his company
• The sneaky strategy that helped him transition from freelance to founder
• How category design differs from traditional branding
• Why “love and money” are the two forces every entrepreneur must balance
• How AI is transforming creative work—and how to stay ahead of it
• The mindset that turns transparency into a competitive advantage

Josh also reveals the pivotal books that shaped his business thinking: Win Without Pitching by Blair Enns and The E-Myth Revisited by Michael E. Gerber.

Key Quotes:

• “You’re going to die someday. Not starting your dream because you’re afraid of what people will think is a ridiculous reason.”
•  “Positioning isn’t about being better—it’s about being different.”
•  “The agencies that will win in the AI era are the ones that move fluidly between human and artificial intelligence.”

Resources Mentioned:

• Win Without Pitching by Blair Enns
• The E-Myth Revisited by Michael E. Gerber
• Gold Front – Category Design Studio

Connect with Josh Lowman:
Follow Josh on LinkedIn for insights on category design, creativity, and leadership.

Connect with Olivia & Building Iconic:

Follow Olivia on LinkedIn and stay tuned for more candid conversations with founders, creatives, and industry builders shaping what’s next.

Olivia sits down with Ahana, founder and CEO of Clear, a YC-backed beauty tech company that tells you which skincare products actually do something instead of just draining your wallet. Ahana went from physics student to accidental entrepreneur after years of acne, useless prescriptions, and too many doctors who didn’t talk to each other. Armed with spreadsheets, photos of her own face, and a healthy disregard for industry nonsense, she built Clear to track products like a science experiment and crowdsource real results.

They talk about raising money when investors think “skincare app” is a cute hobby, why she refuses to hire a giant team, and how running a startup can wreck your health if you let it. Ahana is refreshingly honest about the grind, the late-night YC pitches, and the reality of building a company with just two full-time humans and a lot of stubborn focus.

Key Takeaways

• Data beats marketing: Clear uses real user results to recommend products, not influencer hype.
• Talk to users first: Ahana did months of interviews before writing a single line of code.
• Small team, big output: Two people, plenty of discipline, no excuses.
• Health isn’t optional: Burnout is real, and founders don’t get an HR department to save them.
• Transparency matters: Inside the app and inside the company, clarity wins.