In this episode, Kelly Gillease, two-time CMO, daily meditator, and former search marketer turned executive leader, talks candidly about the inner game behind durable leadership. She traces her path from debating podiums to performance marketing at Hotwire, through scale-up chaos at NerdWallet and post-acquisition life at TripAdvisor/Viator—sharing how mindfulness, therapy, and a “true, kind, necessary” feedback filter helped her steady teams when everything felt on fire.

Kelly opens up about a tough DEI misstep, how she took the feedback without getting defensive, and why she chose to “run toward” hard conversations instead of retreat. She gets tactical about cross-functional influence (and why debate training still matters), building reputations through appreciation rituals, and choosing environments that actually fit you, even when the shinier title says otherwise.

In this conversation, you’ll learn:

- How to use “true, kind, necessary” to deliver (and receive) feedback that lands, and what to do when it doesn’t

- Practical rituals for team resilience: appreciations, mindful pacing, and calmly problem-solving without losing speed

- How to pick the right work environment for your wiring. and navigate the politics, pacing, and trade-offs of big-co vs. startup life

Things to listen for:

(00:00) Intro

(01:47) Kelly’s roots, early influences, and formative values

(03:51) Where creativity meets ROI: loving both art and math

(09:05) Thank you to our sponsor, Navattic

(13:50) Scripts and mindsets for hard feedback and conflict

(24:23) Owning a DEI misstep, pausing, and moving forward

(29:22) Gratitude rituals at work and at home that build morale

(39:58) Why big-company bureaucracy wasn’t the right fit

(44:20) Radical honesty, necessary conversations, real growth

A huge thanks to this episode’s sponsor:

Navattic: Interactive Product Demo Software - https://navattic.com/value

Resources:

Connect with Kelly: https://www.linkedin.com/in/kellythepea/

Connect with Andrew:

LinkedIn: https://www.linkedin.com/in/andrewcapland/

Substack: https://media.deliveringvalue.co

Hire Andrew as your coach: https://deliveringvalue.co/coaching

Join Growth OS: https://deliveringvalue.co/growth-operating-system

In this episode, Ryan McCready, content leader turned Principal Content Engineer at Demostack, opens up about the moments that shaped his path: hacking distribution in the early “monoculture SEO” days, sharpening his voice through roles at Foundation, Reforge, and Whimsical, and facing his first layoff. He shares candid stories about creator burnout after viral teardowns, being the last marketer standing after cuts, and the gut punch of being told he hadn’t delivered on a role that had completely changed. When the market went quiet, Ryan turned the setback into a story on LinkedIn, igniting a thousand DMs, weeks of interviews, and a fresh sense of momentum.

Now, as a builder and editor who treats vulnerability like a career asset, Ryan talks about measuring success in relationships, not just metrics, documenting your receipts, keeping your voice, and sending that DM. He breaks down the unglamorous parts of leadership: giving and receiving hard feedback, guarding against plagiarism, and aligning work with products that actually have staying power, while showing how practical AI and automation can clear the busywork so you can create with intention.

In this conversation, you’ll learn:

• How vulnerability, done thoughtfully, can unlock opportunity, community, and your next role

• Practical ways to productize your “receipts” with AI or automation so your wins market themselves

• How to deliver and absorb tough editorial feedback while protecting quality and your own voice

Things to listen for:

(00:00) Intro

(01:34) Ryan’s early career and content creation journey

(04:19) Navigating career challenges and feedback

(09:37) Thank you to our sponsor, Navattic

(11:04) Giving and receiving feedback

(14:58) On being a team player

(17:41) The importance of adaptability

(31:18) The power of vulnerability in job hunting

(35:39) Creating a strong online presence

(41:57) Difficult conversations in leadership

(51:16) Building professional relationships

A huge thanks to this episode’s sponsor:

Navattic: Interactive Product Demo Software - https://navattic.com/value

Resources:

Connect with Ryan:

LinkedIn: https://www.linkedin.com/in/ryan-mccready

Demostack: https://www.demostack.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

Join Growth OS: https://deliveringvalue.co/growth-operating-system

In this episode, Kirk Reynolds, seasoned founder and now the creator of Wilder Retreats, opens up about the hardest conversations of his career. From telling his 55-person team that he was selling the company without sharing the real reason, to navigating the identity crisis that came when the acquirer shut it down, Kirk reflects on what it means to lead with honesty, even when fear and burnout make it tempting to hide.

He also shares how blunt feedback about being a “people pleaser” reshaped the way he manages, and why processing failure and loss is just as important as chasing growth. This is a conversation about leadership, identity, and the courage it takes to be fully yourself when the stakes are high.

In this conversation, you’ll learn:

• Why trusting your team with the truth builds deeper loyalty and respect

• How to process the emotional toll of selling, losing, or reinventing a business

• Why intention and self-awareness can turn difficult feedback into lasting growth

Things to listen for:

(00:00) Intro

(01:51) Kirk’s first steps into entrepreneurship

(06:26) Building and scaling Discover Outdoors

(08:31) Joining Abercrombie & Kent after exit

(11:02) Tough feedback and personal growth

(20:48) Balancing leadership with family life

(25:26) Lessons from difficult conversations

(26:04) Deciding to sell Discover Outdoors

(28:14) Telling the team about the sale

(30:31) Reflecting on honesty in leadership

(34:27) The emotional weight of selling

(37:48) Finding gratitude in new beginnings

(40:03) Preparing mind and body for conversations

(45:32) Setting bold, ambitious goals

Resources:

Connect with Kirk:

LinkedIn: https://www.linkedin.com/in/kirk-reynolds/

Wilder Retreats: https://discoverwilder.com/

Connect with Andrew:

LinkedIn: https://www.linkedin.com/in/andrewcapland/

Substack: https://media.deliveringvalue.co

Join Growth OS: https://deliveringvalue.co/growth-operating-system

Hire Andrew as your coach: https://deliveringvalue.co/coaching