Delivering Value: Vulnerable Career Stories & Startup Leadership Challenges

In this episode, Gururaj Pandurangi, three-time founder and CEO of ThriveStack, opens up about the near-death moments, pivots, and internal reckonings that shaped his entrepreneurial journey. From growing up in Mumbai with dreams of becoming a scientist to leading multi-million dollar product bets at startups backed by Microsoft and Deloitte, Guru shares what it really takes to build when the vision keeps shifting and the runway ke...

Can you be too nice to lead?

In this episode, Michael Leibovich, GM and Head of Growth at Adobe, shares the career pivots, personal awakenings, and leadership lessons that shaped his unconventional journey from touring musician to executive. Michael opens up about getting fired, receiving feedback that questioned his approach to leadership, and learning how to balance empathy with outcomes. From scaling growth teams at Vimeo, Mindbo...

What happens when your dream job starts crushing your values instead of honoring them?

In this episode, Steph Pennell—founder of The Event Critic and former marketing leader—opens up about the moments that pushed her to reevaluate everything. From getting a shocking piece of feedback about wearing red lipstick to quitting a high-profile job with no backup plan, Steph shares what it takes to walk away from misalignment and rebuild yo...

What happens when you finally land the leadership role you’ve been working toward—only to realize it’s not what you imagined?

In this episode, Shannon Curran—former VP of Marketing at MadKudu and now founder of SSC Consulting—opens up about the real moments that shaped her career. From growing up as a risk-averse high achiever to becoming a solopreneur trusted by founders, Shannon shares the feedback that shook her, the environments...

What makes someone walk away from a PhD, a career in law, and the startup that made them?

In this episode, I sit down with Else van der Berg—a former head of product turned solopreneur—to unpack the hard-earned lessons from the burnout that nearly broke her. Else shares how working 80-hour weeks and tying her identity to performance pushed her to the brink—and what changed afterward.

We talk about how startup culture, pressure to “al...

Devin Bramhall has been a VP of marketing, a CEO, a fractional CMO, and now an author, but none of that came without falling on her face multiple times.

In this episode, Devin opens up about the mistakes that got her fired (twice), the time she unknowingly helped commit financial fraud, and the zero-tolerance plagiarism incident that backfired in the worst way. Through all of it, she’s held onto her belief that everything from leade...

What makes someone leave a high-paying product marketing role just before a massive acquisition?

In this episode, I sit down with Jason Oakley—founder of Productive PMM and co-founder of Demo Dash—to unpack the bold career decisions that shaped his journey in tech. From leading product marketing at a hypergrowth startup to becoming a full-time creator and consultant, Jason shares the systems, mindset shifts, and lessons that helped ...

Erin Balsa’s journey from teaching troubled teens to becoming a solopreneur in content marketing is anything but conventional. After a rewarding but challenging career in education, Erin found herself pivoting to tech marketing, working her way up to director roles at companies like Predictive Index. But the leap from the corporate world to running her own business wasn’t without its hurdles.

In this conversation, Erin shares the un...

Ty Magnin, former marketing leader at Appcues and UiPath, now CEO at Animalz, made a mistake that could’ve ended his career.

While leading a team at UiPath, he accidentally uploaded a private doc that outlined a power shift — and the wrong person saw it. What followed was a firestorm of Slack messages, a panic spiral, and a career-defining moment of humility and growth.

In this conversation, Ty shares the leadership mistakes that alm...

Elena Luneva, VP of Product at GoFundMe, opens up about the hard-earned lessons that shaped her leadership journey—from navigating layoffs early in her career to building a business unit from scratch at Nextdoor. In this episode, Elena shares how receiving career-altering feedback about her confidence changed her trajectory, why moving from “being right” to “being effective” became a career mantra, and how she learned to lead throu...

This episode is presented by:

AppUnite: The right dev partner can make or break your product. AppUnite embeds with your team to build apps that scale. - https://bit.ly/3QOKHtT

Fullstory: Behavioral data that empowers - https://fullstory.com/value

April Dunford, author and globally recognized expert on product positioning, reflects on her unconventional journey from aspiring doctor to tech executive to in-demand consultant. In this e...

Amaan Nathoo is a former VP of Growth turned fractional growth advisor, with deep experience navigating fast-growing startups and the emotional rollercoaster of career transitions. In this episode, Amaan opens up about how a founder’s offhand remark early in a new role shook his confidence, how imposter syndrome shows up in subtle ways, and why he ultimately chose to walk away from a full-time leadership role to build a consulting ...

This episode is presented by:

• AppUnite: The right dev partner can make or break your product. AppUnite embeds with your team to build apps that scale. - https://bit.ly/3QOKHtT
• Fullstory: Behavioral data that empowers - https://fullstory.com/value

John Bonini, founder of Content Brands, opens up about his early struggles building an audience—before realizing the power of original thinking, consistency, and fully owning his v...

Maja Voje, a go-to-market consultant and bestselling author of The Go-To-Market Strategist, has worked with over 800 companies, from Google and Rocket Internet to startups and scale-ups. But even with an impressive career, she’s had to make tough calls—like recognizing when it’s time to walk away from a role.

Maja opens up about:

- The fear of overstaying vs. leaving too soon

- How she evaluates whether to stick with a role or move on

...

Yue Zhao, former PM at Meta and Instagram, and Founder of The Uncommon Executive, shares how she struggled with promotions early in her career—until she learned how to navigate corporate politics. From feeling stuck in a startup to learning how influence and perception shape career growth, Yue opens up about the pivotal lessons that changed her approach and ultimately helped her scale to leadership roles in tech.

Yue opens up about:

...

Mackenzie Hughes, Co-Founder of GoldHue and former Product Ops Leader, shares how she navigated career pivots, overcame self-doubt, and ultimately built a business rooted in purpose.

From knocking on doors as a political canvasser to leading product teams at high-growth startups.

Mackenzie reflects on the pressures of leadership, the identity shifts that come with climbing the corporate ladder, and the moment she realized she had b...

Pranav Piyush, CEO and Co-Founder of Paramark, shares the moments that shaped his journey from scaling a YC startup to facing a co-founder breakup and battling imposter syndrome while fundraising. He reflects on the tough feedback that shook his confidence at Dropbox, the mindset shifts that kept him moving forward, and why resilience isn’t just about working harder, it’s about trusting your instincts, staying clear-eyed under pres...

Tiffany DaSilva – SEO and PPC consultant, Founder of DaSilva Consulting, and educator with programs at McMaster University and Grow Class, shares the defining moments that shaped her career and personal growth.

From breaking into the male-dominated tech space to starting her own business after a near-death experience, Tiffany reflects on her journey with honesty and resilience. With 19 years of experience, over 500 websites, and 300...

Austin Hay, co-founder of Clarify, shares candid insights into his journey as a startup leader.

From navigating a messy exit to overcoming personal loss, Austin reflects on the experiences that have shaped him both professionally and personally.

Austin opens up about:

• His struggles with taking work too seriously and learning to balance ambition with self-care
• Navigating bereavement while managing a demanding role
• Building resilienc...