Yue Zhao, a former PM at Meta and Instagram and founder of The Uncommon Executive, shares her journey from feeling overlooked to mastering corporate politics. She discusses the realization that hard work alone doesn’t guarantee promotions. Instead, she emphasizes the importance of building influence and strategically framing her goals. Yue also addresses challenges in early startup roles and the significance of relationships in career advancement, revealing how understanding workplace dynamics can lead to leadership success.

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 been contorting herself to fit an environment that was never built for her.Mackenzie opens up about:- The gut feeling she ignored when stepping into a leadership role - Why corporate “professionalism” often reinforces bias and how she stopped playing the game- The hard-won lesson that success isn’t about making more money, it’s about aligning with what actually mattersThings to listen for:(00:00) Changing yourself to fit in (02:06) Why Mackenzie values vulnerability and honest conversations (08:45) Early career: Political and nonprofit campaigns (09:10) Thanks to our sponsor, Fullstory(14:30) Overcoming fear of public speaking (23:35) A career low point: Feeling disillusioned in her last role (29:19) A coach’s insight that helped Mackenzie find authenticity (32:32) Enabling the patriarchy vs. staying true to herself (36:29) The challenge of under-resourcing and lack of support (46:38) Losing herself in a money-driven mindset (51:00) Creating a vision board and defining her ideal state This episode is presented by:Fullstory: Surface User Sentiment with Behavioral Data - https://fullstory.com/valueResources:Connect with Mackenzie::LinkedIn: https://www.linkedin.com/in/mackenzierhughes/ GoldHue: https://www.goldhue.co/ Connect with Andrew:LinkedIn: https://www.linkedin.com/in/andrewcapland/ Hire Andrew as your coach: https://deliveringvalue.co/coaching

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 pressure, and embracing the uncomfortable moments that lead to real growth.Pranav opens up about:The wake-up call that forced him to rethink how he navigated internal politicsHow his first startup experience ended in heartbreak but led to an even bigger opportunityWhy founders need a “reality distortion field” to sell their visionThings to listen for: (00:00) Pranav discusses his experience with YC and an unexpected rift with his co-founder (03:39) Developing persuasive skills through debate and their benefits in tech leadership (06:29) The accidental start of an entrepreneurial journey with a student job platform (08:05) Thanks to our sponsor Fullstory (10:08) Receiving tough feedback at Dropbox and its personal impact (24:27) The highs and lows of Pranav's first venture and parting ways with his co-founder (38:21) Viewing setbacks as part of the journey to success (39:36) Handling imposter syndrome during a challenging fundraising period (49:18) The role of manifestation and goal-setting in Pranav's life and work This episode is presented by: Fullstory: Surface User Sentiment with Behavioral Data. - https://fullstory.com/valueResources: Connect with Pranav: LinkedIn: https://www.linkedin.com/in/pranavp/ Paramark: https://paramark.com/Connect with Andrew: LinkedIn: https://www.linkedin.com/in/andrewcapland/ Hire Andrew as your coach: https://deliveringvalue.co/coaching

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 clients under her belt, she opens up about her struggles, victories, and the lessons learned along the way.Tiffany opens up about:Walking out of a toxic unicorn startup and rebuilding her career from scratchThe importance of creating a “Shine Crew” for support and accountabilityHandling harsh feedback and learning to discern what’s worth changingThings to listen for: (00:00) Tiffany standing up for herself after being overlooked (04:36) Joining a unicorn startup and facing cultural clashes (10:28) Thanks to our sponsors, Navattic & Appcues (21:05) Building a “Shine Crew” to create a support network (26:47) Handling tough feedback and deciding what to change (36:20) Breaking barriers in a male-dominated industry (47:49) Aligning your business with personal values (53:22) Managing imposter syndrome and rebuilding confidence (56:55) Using mindfulness to reset after tough moments (59:07) Listening to her gut and charting her own pathThis episode is presented by: Navattic: Interactive Product Demo Software - https://navattic.com/value Appcues: User Engagement for SaaS - https://appcues.com/valueResources: Connect with Tiffany: LinkedIn: https://www.linkedin.com/in/tiffanydasilva Instagram: https://www.instagram.com/thetiffdasilva/ DaSilva Consulting: https://www.tiffanydasilva.com/Connect with Andrew: LinkedIn: https://www.linkedin.com/in/andrewcapland/ Substack: https://media.deliveringvalue.co Hire Andrew as your coach: https://deliveringvalue.co/coaching

Austin Hay, co-founder of Clarify, dives into his provocative journey through the hectic startup world and personal loss. He discusses the importance of not taking work too seriously while maintaining ambition and self-care. Hay candidly reflects on navigating grief and how it influences resilience in high-pressure roles. He emphasizes the need for vulnerability and shares valuable lessons from his challenging career transitions. This conversation is a heartfelt blend of professional wisdom and personal insight, perfect for any aspiring founder.

Ciara Peter, SVP of Product at Robin, opens up about the career highs and lows that shaped her leadership journey.From navigating imposter syndrome to overcoming burnout in Silicon Valley startups, Ciara shares the pivotal lessons that helped her find confidence and clarity. She takes us behind the scenes of her time at Salesforce, the mistakes that taught her the most, and how prioritizing trust and alignment transformed her career. Ciara opens up about:Facing imposter syndrome as a new managerHer viral LinkedIn post showcasing 15 years of struggle behind her successAlmost crashing a live demo in front of 10,000 peopleHow working at an early-stage startup impacted her mental healthBuilding trust as a leader and balancing strategic conviction with collaborationThings to listen for: (00:00) Ciara’s early career struggles and viral LinkedIn post (04:09) The turning point that led to her role at Salesforce (12:05) Breaking the code at Dreamforce and the lessons learned (24:26) Why early-stage startups took a toll on her mental health (30:44) How imposter syndrome shaped her leadership style (39:57) Navigating trust and alignment as an SVP Connect with Ciara: LinkedIn: https://www.linkedin.com/in/ciarapeter/Connect with Andrew: LinkedIn: https://www.linkedin.com/in/andrewcapland/ Substack: media.deliveringvalue.co Hire Andrew as your coach: https://deliveringvalue.co/coaching

Annie Katrina Lee, Co-Founder and Principal of Penknife Collective, opens up about the moments that challenged her identity and reshaped her perspective on success. From bold career moves at Microsoft to walking away from high-profile CMO roles, Annie shares how she navigated rejection, imposter syndrome, and the evolving priorities of motherhood.Annie opens up about:Landing her first tech role at Microsoft by taking a bold riskFacing rejection and rebuilding confidenceHow becoming a mother at the height of her career reshaped her identity and prioritiesThe tough feedback that taught her the importance of balanceThings to listen for:(00:00) Annie’s first CMO role and feeling incomplete(08:43) Landing a job at Microsoft through boldness(13:10) Facing rejection during the 2009 recession(14:03) Thanks to our sponsor for this episode, Navattic & Appcues(17:36) The challenges of being a working mom and its impact on identity(20:44) Reevaluating priorities after losing your love for the craft(27:49) The impact of tough feedback: “You care too much”(39:57) Overcoming imposter syndrome in techThis episode is presented by:Navattic: Interactive Product Demo Software - https://navattic.com/value Appcues: User Engagement for SaaS - https://appcues.com/value Connect with Annie:LinkedIn: https://www.linkedin.com/in/anniekatrina/ Penknife Collective: https://www.penknifecollective.com/ Connect with Andrew:LinkedIn: https://www.linkedin.com/in/andrewcapland/ Substack: https://media.deliveringvalue.coHire Andrew as your coach: https://deliveringvalue.co/coaching

Brian Balfour, Founder & CEO of Reforge, shares raw insights from his entrepreneurial journey. From navigating burnout and sleep disorders to rebuilding trust after tough feedback, Brian reflects on the challenges that shaped his leadership philosophy and personal growth.Brian opens up about:Feeling “broken” during a burnout moment that forced him to step back and resetStruggling with imposter syndrome and comparing himself to peers like Mark ZuckerbergLessons learned from career lows, including a product shutdown and a legal battleThings to listen for:(00:00) Brian Balfour: burnout and feeling broken(02:33) Building deeper connections through vulnerability(07:27) Launching Reforge Insight Analytics(12:28) Lessons from Brian’s first startup vs. Facebook(19:12) Overcoming feeling stuck by taking action(29:31) Thanks to our sponsors for this episode, Navattic & Appcues(27:09) Career lows and lessons in resilience(33:34) Managing burnout and physical health(41:10) Handling direct feedback and rebuilding trust(50:43) Creating boundaries between work and familyThis episode is presented by:Navattic: Interactive Product Demo Software - https://navattic.com/value Appcues: User Engagement for SaaS - https://appcues.com/value Resources:Connect with Brian:LinkedIn: https://www.linkedin.com/in/bbalfour/ Website: https://brianbalfour.com/ Reforge: https://www.reforge.com/ Connect with Andrew:LinkedIn: https://www.linkedin.com/in/andrewcapland/ Substack: https://media.deliveringvalue.coHire Andrew as your coach: https://deliveringvalue.co/coaching

Erika Warren, Co-Founder & CEO of Insightful, reflects on the pivotal moments that tested her confidence and redefined her career. From being blindsided by a job change at Grubhub to walking away from a role she couldn’t fix, Erika shares how she navigated self-doubt, burnout, and the pressure of being the primary earner for her family.Erika opens up about:Crying in a meeting after being handed a new role she didn’t understandLeaving Change.org without another job lined up, despite the financial risksNavigating a crisis of confidence and learning to separate her identity from professional outcomesThings to listen for:(00:00) Erika’s lowest point: giving up on the job(06:02) Frustrations with corporate life in her first marketing role(08:21) Bursting into tears after being handed a product role at Grubhub(15:22) Advice for handling unexpected job changes(17:46) Quitting without a safety net as the primary earner(19:58) Thanks to our sponsor for this episode, Churnkey(25:50) Losing confidence and dealing with a crisis of identity(31:56) Why success comes from the environment, not the individual(41:47) Balancing imposter syndrome and a growth mindsetResources:Connect with Erika:LinkedIn: https://www.linkedin.com/in/erika-warren/ Inciteful: https://inciteful.xyz Connect with Andrew:LinkedIn: https://www.linkedin.com/in/andrewcapland/ Hire Andrew as your coach: https://deliveringvalue.co/coachingThanks to our amazing sponsor!Learn more about Churney: https://churnkey.co/

Anthony Scarpaci - Former VP of Growth at Acorns and Founder of TUNOMATIC, shares the toughest moments in his career that shaped his leadership philosophy. From navigating high-stakes mistakes to balancing empathy with assertiveness, Anthony opens up about the defining experiences that molded him into the leader he is today. He reflects on his journey across growth roles at companies like Betterment, NerdWallet, and Blue Apron, while offering candid advice for leaders facing their own career challenges.Anthony opens up about:1. Making a massive mistake early in his career and being told it could cost him his job2. Getting feedback in a formal 360 review that he was “too nice” as a leader3. Returning from his wedding in Italy to perform layoffs at 8 AM the next morningThings to listen for:(00:00) Owning up to an early career mistake(08:38) Transitioning from music to tech & marketing(13:37) The scariest moment of Anthony’s career(19:46) Learning from a crisis: Building trust and accountability as a young leader(25:57) Feedback that Anthony was “too nice” and learning to assert himself(28:21) Thanks to our sponsors for this episode, Navattic and Appcues(31:20) Managing across and up: How to navigate organizational dynamics(36:08) Conducting layoffs and the emotional toll of tough decisions(47:55) Key lessons from handling high-pressure situations(50:46) Giving yourself grace and focusing on what’s in your controlResources:Connect with Anthony:LinkedIn: https://www.linkedin.com/in/anthonyscarpaci/ TUNOMATIC: https://www.tunomatic.com/ Connect with Andrew:LinkedIn: https://www.linkedin.com/in/andrewcapland/ Hire Andrew as your coach: https://deliveringvalue.co/coachingThanks to our amazing sponsors!Learn more about Navattic: https://navattic.com/value Learn more about Appcues: https://appcues.com/value