In this episode of Clover, I get to catch up with my longtime friend and powerhouse media executive, Tracy Kaplan, and her “hodgepodge” career that turned out to be a masterclass in building a bold, non-linear path in media, tech, and podcasts.

Tracy walks us through her journey from WGBH and ABC News to CBS Interactive, SnappyTV, Twitter, TuneIn, Patreon, Tenderfoot TV, and now Courier Newsroom, all while launching her own company, Small But Mighty Media, and creating The 10 News, an award-winning news podcast for kids. Along the way, she shares how she spots the real inflection points in media (from mobile video to podcast subscriptions to now AI), builds durable partnerships with platforms like Apple and Spotify, and refuses to let imposter syndrome keep her from jumping into the next big thing.

We also dig into the business side: subscription models, monetization beyond ads, what actually grows a podcast audience, and how to lead high-pressure teams through constant change without burning everyone out.

In this episode, you’ll learn:

• How to turn a “hodgepodge” career into a strategic advantage and deliberately collect the skills and experiences you’re missing instead of chasing a straight line.
• How to spot the next wave in media and tech by staying curious, observing real people’s behavior (hello, commuters watching video in Japan), and forcing yourself to experiment with new tools like AI before you feel “ready.”
• Practical ways to move into a new lane—before you’re an expert, including how Tracy taps her network, asks smart questions, and leverages subject-matter experts to fill her own gaps.
• A clear breakdown of podcast monetization today—ads, Apple/Spotify subscription channels, Patreon-style membership, and even donations and fiscal sponsorship—and how to think about diversifying your revenue so you’re not at the mercy of one market.
• How Tracy built and scaled The 10 News for kids, including the real origin story (NPR in the school pickup line + political ads on YouTube) and the tactics she used to secure high-caliber guests like Dr. Fauci.
• What makes a partnership last in a fickle industry, from being radically responsive and direct, to making every deal a “win-win” instead of a zero-sum transaction.
• Tracy’s leadership philosophy in high-pressure environments—how she pushes her team to grow while still rolling up her sleeves, taking on grunt work when needed, and making sure no one is left to fail alone.
• Hard-won career advice for women in media and podcasting, including why allies inside and outside your company matter, how to recognize when it’s time to leave a role you once loved, and why tearing other women down is a long-term losing strategy.
• Her big blue-sky vision for helping kids and families better understand the world—and why she dreams of a “domestic Peace Corps” style program that gets people outside their bubbles and into each other’s communities.

If you’ve ever worried that your career looks “messy” on paper, or felt behind on the latest shifts in media, this conversation will give you both a roadmap and a serious permission slip to build something beautifully non-traditional.

In this episode, I sit down with mortgage industry veteran and coach Carrie Guarrero to trace a three-decade career built on service, community, and relentless growth. Carrie shares how an 11-year-old’s flyer route in her mom’s mortgage office became a billion-dollar origination career—and why the trophies eventually mattered less than the names and stories behind each loan. She opens up about a career “pause” that didn’t go as planned, the humbling return that led her to Fairway, and how that detour became the on-ramp to launching Fairway Ignite, an internal coaching organization now serving 600+ teammates with 80 coaches.

We also get into how Carrie is building a multigenerational legacy; handing portions of her book of business to her daughter and longtime partner, and what “effective coaching” really looks like inside a high-performance culture: individualized matches, data-driven accountability, and an always-on community. Beyond business, Carrie reflects on being an Army mom (and former Army spouse), holding pride and fear at the same time, and the leadership lessons that come from service, ambiguity, and letting go. She previews her forthcoming guided journal Discovering WISE: Women in Search of Excellence—a 52-week journey designed to help women define success on their own terms—and shares the daily non-negotiables that keep her grounded in faith, family, gratitude, sweat, and stillness.

Discussion Highlights:

• How a “failed” pivot can become the exact path you need next
• The core ingredients of coaching that actually moves numbers (and people)
• Why legacy leadership means empowering others, even before you feel ready to let go
• Navigating male-dominated rooms without dimming your light or your voice
• The power of holding two truths (proud and scared) and leading through uncertainty
• A simple morning framework: gratitude, sweat, and reflective thinking

Links & Mentions:

• Connect with Carrie Guarrero:  Instagram • LinkedIn 
• Book: Discovering WISE: Women in Search of Excellence — 52-week guided journey - grab your copy here!

If this conversation resonates, I’d love for you to subscribe, rate, and share. Tag me with your takeaways and the line that hit you hardest.

In this conversation, I catch up with longtime friend and operator, Stephanie Quay—a five-time acquisition veteran who recently launched Five Experts, a platform matching early-stage companies with proven operators to drive value creation in the first five years. We trace her zig-zag path from film school and TV.com (hi, CNET days!) to growth-stage leadership across PE- and VC-backed companies, and the playbooks she now packages for founders, investors, and fractional experts.

Stephanie opens the hood on the 5×5×5 framework—from the first 90 days through year five—and how to pull the right levers (margin, operations, capital efficiency, customer success, revenue) without losing your culture or your North Star. We also get into what makes someone an expert (outcomes + the ability to teach), why “warm demander” leadership works, and how to protect your focus by controlling what you can (sprinters, we see you).

What you’ll learn

• How to diagnose growth inflection points in the first five years—and what to do in each phase
• The 5 value levers that move EBITDA (with real examples from PE-backed turnarounds)
• Why breaking apart sales vs. customer success can unlock outsized growth
• The difference between experience and expertise (hint: repeatable outcomes + coaching)
• How to set a clear mission/ICP so teams row in the same direction
• “Warm demander” management: high standards + high support
• Mindset for founders: doubt is normal—return to your mission fast

Who this is for:

Founders, operators, and investors navigating resource-constrained growth; women in leadership building high-performing teams; and anyone curious about turning career zigzags into a superpower.

Connect with Stephanie:

• LinkedIn
• Five Experts
• Email: [email protected]
  
  

Favorite lines

• “An expert has proven the outcome—and can teach the path back.”
• “Culture and mission aren’t posters; they’re the daily operating system.”
• “Control the controllables. Ignore the rest.”

For years, women in leadership have been told to “find balance” — as if the secret to thriving careers, healthy families, and full lives could fit neatly into a color-coded planner. But what if balance isn’t the goal at all? What if it’s the trap?

In this solo episode of Clover, I unpack the myth of balance — how it was sold to women as a shiny standard we could never meet, and why it’s time to let it go for good.

From early-morning Zoom calls in yesterday’s t-shirt to late-night Slack pings and school newsletters, I take you inside the messy, over-caffeinated reality of leadership and the impossible expectations women face to do it all.

We’ll dig into:

•  Why “balance” is often just code for “don’t let anything slip.”
• The difference between balance and clarity — and why clarity wins every time.
• How real women leaders decide what to protect, what to let go of, and what truly matters.
• Five practical strategies to ditch the balance myth and lead with intention instead.

This episode is for every woman who’s ever felt like she’s failing at balance — when in reality, she’s succeeding at prioritizing what matters most.

Because the truth is, you’re not here to do it all. You’re here to lead — clearly, powerfully, and unapologetically.

In this episode of Clover, I’m rethinking one of the biggest myths about career growth — the idea that success is about climbing a ladder.

For many of us, especially women, that ladder was never built for the way our careers actually unfold. So let’s talk about a better metaphor: the jungle gym. It’s flexible, unpredictable, and a whole lot more real.

I share lessons from my own path — from film school to marketing, from startups to enterprise leadership — and how every pivot, pause, and sideways move became part of the story I was meant to build.

We’ll dig into:

• Why lateral moves can be the smartest play
• How to recognize what season you’re in — growth, rest, or healing
• The importance of building your network before you need it
• How to own and narrate your unique career story
• Letting go of timelines that tell you where you “should” be by now

If your path doesn’t look like a straight line, good. That means you’re learning, adapting, and leading in your own way — and that’s where the good stuff happens.

What’s one non-linear move you’ve made that taught you something you couldn’t have learned any other way? Write it down, share it, or simply own it — that’s your jungle gym résumé, and it’s powerful.

If this episode resonates, share it with another woman who needs the reminder: she’s not behind — she’s building her own structure. 

In this episode of Clover, I sit down with the incredible Erin Rich, VP of Trade Marketing & Communications at Paramount, for a conversation that feels like a time capsule of the tech, media, and entertainment worlds over the last three decades — and a masterclass in reinvention.

Erin takes us through her journey from the early Bay Area startup scene and the heyday of Yahoo and CNET, through mergers at CBS Interactive and ViacomCBS, to her current leadership role at Paramount. She shares how putting the user at the center has been her guiding thread, what it really means to “reinvent yourself” through industry shifts, and how she’s built influence in rooms where authority isn’t always guaranteed.

We also talk about:

•  The iconic Yahoo billboard and what it symbolized for an entire era of innovation
• The early debates about mobile adoption (and why we were all wrong!)
• How Erin helped her teams “zag” during reorganizations by identifying unmet needs
• What it takes to lead through influence, not hierarchy
• Why mentoring across multi-generational teams matters more than ever
• Three myths women in leadership should stop believing
• The importance of learning to get comfortable being uncomfortable

Erin’s story is one of resilience, curiosity, and purpose — and her advice for women navigating leadership, change, and growth is refreshingly real.

You can connect with Erin on LinkedIn.

I sit down with Conni Francini, CEO of Soro Publishing, to explore how she’s building a more author-friendly path to publishing. Conni traces her unconventional route—from journalism/PR into education, then a 15-year run in educational publishing where she rose to editor-in-chief and developed award-winning products with partners like the Smithsonian and TIME for Kids.

After dozens of candid chats with writers—frustrated by low royalties, limited marketing, slow timelines, and losing creative control—Conni launched Soro Publishing. The model blends the best of traditional and self-publishing: professional editorial and design, months-not-years timelines, authors keeping their rights, creative control, and most royalties, plus a true partnership to grow their platforms.

We dig into Soro’s three focus lanes—education, business/leadership, and children’s books—and what’s surprised Conni most about entrepreneurship: the sheer build-from-scratch workload, the importance of loving sales/BD as much as “making the book,” and staying adaptable when the market pulls you into new genres. Conni also shares hard-won lessons for leading creatives (define outcomes, not pixel-perfect solutions) and encouragement for first-time founders and execs: ask for help early and often—you’ll be surprised how many people say yes.

• Why many authors feel stuck between traditional and self-publishing—and how a hybrid model can be a win-win.
• The specific ways Soro helps authors retain rights, voice, and royalties while leveling up quality and speed.
• How to lead multidisciplinary creative teams: set audience outcomes, invite expertise, and critique by problem, not by prescription.
• The underestimated realities of starting a company (and how to balance making the product with marketing/business development).
• How to stay adaptable when real-world feedback nudges your strategy into new lanes.
• Practical networking advice for new execs/founders: how (and why) to ask for guidance from leaders you don’t even know yet.

• Conni Francini on LinkedIn
• Soro Publishing
• Instagram — @soropublishing
• Past partnerships referenced: Smithsonian, TIME for Kids

In this heartfelt, high-energy conversation, Stephanie Bohn—entertainment veteran turned startup founder—traces her journey from American Express to 13 years at Warner Bros., scaling Rotten Tomatoes, a pivotal stint at Netflix, and ultimately to purpose-built entrepreneurship. Stephanie shares how “raising your hand before you feel 100% ready” opened doors to building new business lines (hello, early App Store days) and leading through ambiguity. We dig into her time as CMO at Chief, the power of peer boards for executive women, and what servant leadership looks like in practice. The episode turns deeply personal as Stephanie opens up about her daughter’s Rett syndrome diagnosis, the broken systems families navigate, and how that sparked Truly Care—a mission-driven platform connecting families with specialized caregivers and guiding them to underused respite resources. It’s a masterclass in turning obsession into action, finding champions, and designing a life that sustains both ambition and wellbeing.

We cover:

• Spotting and pitching opportunities before you’re “ready”
• Intrapreneurship at scale: apps, IP, and the Rotten Tomatoes playbook
• Inside Chief: “who mentors the mentors?” and changing the face of leadership
• Caregiving as infrastructure: access, affordability, and dignity
• Defining servant leadership and leading by removing obstacles
• Founder fuel: memoirs, The Pitch podcast, and mindset rituals that stick

Guest links:

• LinkedIn
• Website
• Instagram

Mic-drop moment: “If you’re obsessed with the idea, break it into nano-steps, find your champions, and build the scaffolding until it exists.”

This week on Clover, I sit down with Emily Gupton—a technology leader, community builder, and soon-to-be President of Austin Women in Technology. Emily’s career path has been anything but linear: from studying neuroscience and working in radiology, to project management in commercial furniture, to building a SaaS platform from the ground up, and now serving as CTO at SKG.

In this conversation, Emily shares how curiosity, resilience, and community have shaped her many pivots. She opens up about navigating male-dominated spaces in tech, the power of asking questions (even the “silly” ones), and how investing in education—from her MBA to an MIT certificate—helped her bridge career transitions.

We also dive into Emily’s passion for building inclusive communities, her leadership journey with Austin Women in Technology, and her past work with the League of Women Voters of Texas. Whether you’re considering a career pivot, looking for inspiration to step into leadership, or craving stories of women making big impacts in Austin and beyond—this episode will leave you energized.

What you’ll learn in this episode:

• How to embrace career pivots with curiosity and courage
• Why community and mentorship are essential in tech (and beyond)
• Emily’s approach to leadership, equity, and empowering diverse voices
• Practical tips for choosing the right further education or certification
• How Austin Women in Technology fosters growth, connection, and opportunity

Connect with Emily:

• LinkedIn: linkedin.com/in/emily-gupton
• Website: emilykgupton.com
• Austin Women in Technology: https://www.awtaustin.org/ 

Communities & Organizations

• League of Women Voters of Texas: lwvtexas.org
• Innotech Women in Tech Summit — partnered event with AWT
• Capital Factory / Austin Tech Week — collaborative events with AWT
• Austin Forum on Technology & Society — partner org for technical topics like quantum computing

Books & Authors

• Smart Brevity — by the Axios team; recommended by her CEO and used as a communication framework
• Neil Gaiman — mentioned as a favorite author for personal, whimsical, and fantastical reading

In this episode of Clover, I sit down with Cherie Werner, the force behind Fiesta, the largest community for founders and investors in Austin, and FoundHERs, a dedicated space for women entrepreneurs. Cherie shares her journey from startup life to building Fiesta almost by accident, and how “leading with welcome” has become her guiding principle.

We talk about what it really takes to turn a crowded room into genuine connections, why consistency and inclusivity matter, and how women founders can push past the urge to be “perfect” before showing up. Cherie also offers simple conversation starters and follow-up practices you can use to walk into any networking event with more confidence.

If you’ve ever felt intimidated walking into a room full of strangers—or if you’re looking for a better way to grow community around your own work—this conversation will give you both inspiration and practical tools.

You’ll learn:

• How Fiesta grew into Austin’s largest founder–investor community
• Practical ways to break the ice beyond “What do you do?”
• Why consistency and inclusivity fuel stronger communities
• A mindset reset for women founders: show up before it’s “perfect”
• Follow-up strategies that turn quick chats into lasting relationships
• How to design events and spaces that make people feel truly welcome

RESOURCES MENTIONED

🌐 Websites & Communities

• FIESTA → https://www.fiesta.community
• Grow.FIESTA (global platform) → https://grow.fiesta.community

📨 Newsletters

• The HERald → Women-focused newsletter Cherie publishes (first Friday after FIESTA events).
• FIESTA Focus → Founder/community newsletter (week before and after each FIESTA).

📱 Social Media

• Cherie’s LinkedIn → https://www.linkedin.com/in/cheriewerner
  (LinkedIn is her most active platform).

📚 Books Mentioned

• Let Them by Mel Robbins
• Believe It by Jamie Kern Lima
• Worthy - Jamie Kern Lima’s second book 

🎙️ Podcasts Mentioned

• All-In Podcast
• On Purpose with Jay Shetty