137: Between the Trigger and the Reaction ft. Sean Kelsey

137: Between the Trigger and the Reaction ft. Sean Kelsey

In this episode, Alex sits down with Sean Kelsey — CEO of Nave Law Firm, foster care alumnus, community builder, and author of The Uneducated CEO — for a conversation about what it really costs to become who you're trying to be. Not in theory. In practice. In the space between the trigger and the reaction. Sean walked into one of the largest DWI law firms in Central New York with no law degree, no formal business training, and one real credential — his past. What he had was a kid's worth of survival instincts, a relentless drive to figure it out, and a belief that negative situations can always be turned into opportunities. Somehow, he became the CEO. But this conversation isn't really about that. It's about the version of Sean that got there — the one who led by fear, who thrived in chaos because chaos was all he'd ever known, and who sat at a kitchen table one ordinary afternoon and realized he was about to break everything around him. It's about what he found on the other side of that moment: therapy, intentionality, a Wellness Army he built for his staff, and a book he wrote not to be published — but to hold himself accountable while finally, slowly, giving himself grace. Because the same intensity that builds the thing can crack it. And Sean Kelsey knows exactly what that costs. 💬 Topics we cover: * How growing up in foster care — riding buses alone at eight, holiday dinners at 7-Eleven — became the foundation of everything he built * What he walked into at Nave Law Firm with no degree, and how he turned a defendant's perspective into a blueprint for scaling operations * The moment at the kitchen table when he realized the problem wasn't his staff, his family, or his circumstances — it was him * What leading by fear actually looks like from the inside — and what it took to change * Why he built a Wellness Army for his team, and what it means to put people before clients before everything else * How he went from feeling like he didn't belong in the room to becoming board president of the organization that gave him that very feeling * What The Uneducated CEO is really about — and why he wrote it to give himself grace while still holding himself accountable If you've ever outworked the room, outrun your own pain, and started to wonder what all of it is actually costing you — this is the episode you needed to hear. New episodes drop every Monday. Ready to Cultivate? Hit Subscribe. Connect with Sean [https://www.linkedin.com/in/sean-kelsey-leader/] Learn more about ⁠⁠Camp Collective⁠⁠ [https://www.cnywomensnetwork.com/camp-collective] Follow Cultivate with Alex Canavan on ⁠⁠Substack⁠⁠ [https://substack.com/@cultivatewithalexcanavan] Follow Cultivate with Alex Canavan on ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.instagram.com/alexcanavanpodcast/] ⁠⁠⁠⁠⁠⁠Apply⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://docs.google.com/forms/d/e/1FAIpQLSevUSBdGbpTOBGXjuGNeY8PN6uNSKHWCJwKOS2SpsCtJ1WCaw/viewform] to be a guest on Cultivate Connect with Alex Canavan, the host of Cultivate on her ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠website⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.alexcanavan.com/], ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠LinkedIn⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.linkedin.com/in/alexcanavan/] & ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.instagram.com/alexcanavan.co/] This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Diam Media Group⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.diammedia.com/]

136: Freeze, Donate, and Change the System ft. Lauren Makler

In this episode, host Alex sits down with Lauren Makler — Co-Founder and CEO of Cofertility, a human-first fertility ecosystem that allows women to freeze their eggs for free when they donate half — for a conversation about turning personal pain into public purpose, building something counterintuitive in an industry that needed disruption, and what it really means to show up for women at one of the most vulnerable moments of their lives. Before Cofertility, Lauren was an early Uber employee who founded Uber Health — a business that leveraged Uber's driver network to help millions of patients access the care they needed. She's been named to Inc.'s 2025 Female Founder 500, Fast Company's Most Creative People in Business, and has been featured everywhere from Vogue to Forbes to Entrepreneur. But behind all of that is a deeply personal story — a rare disease diagnosis, a fertility journey that brought her to her knees, and a sister whose experience with egg donation showed her exactly what was broken about the system and what was possible if someone was brave enough to build something better. She didn't pitch a trend. She didn't chase a market. She took the hardest chapter of her life and built something that didn't exist — because she knew firsthand what it cost women when it didn't. 💬 Topics we cover: * How she turned her most painful personal experience into a company built for millions of women * The model behind Cofertility — and why something this simple took this long for someone to build * What it actually took to build Uber Health inside one of the fastest growing companies in the world * Why the biggest barrier to egg freezing isn't awareness — it's access — and how Cofertility is changing that * What it felt like to sign her Series A term sheet with both of her kids on her lap * How she leads a fully remote team of 32 people with high vibes, high trust, and a Slack channel called the Hype Room * What she tells herself on the days imposter syndrome shows up — and it still does If you've ever wondered whether the thing you've been through could be the thing you were meant to build — this is the episode for you. New episodes drop every Monday. Ready to Cultivate? Hit Subscribe. Learn more about Lauren and Cofertility [https://www.cofertility.com/learn/author/lauren-makler] Learn more about ⁠Camp Collective⁠ [https://www.cnywomensnetwork.com/camp-collective] Follow Cultivate with Alex Canavan on ⁠Substack⁠ [https://substack.com/@cultivatewithalexcanavan] Follow Cultivate with Alex Canavan on ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.instagram.com/alexcanavanpodcast/] ⁠⁠⁠⁠⁠Apply⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://docs.google.com/forms/d/e/1FAIpQLSevUSBdGbpTOBGXjuGNeY8PN6uNSKHWCJwKOS2SpsCtJ1WCaw/viewform] to be a guest on Cultivate Connect with Alex Canavan, the host of Cultivate on her ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠website⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.alexcanavan.com/], ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠LinkedIn⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.linkedin.com/in/alexcanavan/] & ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.instagram.com/alexcanavan.co/] This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Diam Media Group⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.diammedia.com/]

How to Network with Intention (And Actually Build Relationships That Go Somewhere)

Alex is back solo, and this time she's tackling the topic every woman in this community asks her about: networking. Not the awkward, business-card-collecting kind. The intentional kind, the kind that actually turns conversations into community. This episode is the best of a recent Collective call, expanded and made even more tactical. Alex breaks down why most networking advice leaves people feeling like they're just going through the motions, and what to do instead if you actually want your relationships to go somewhere. She gets specific: how to set real, measurable networking goals instead of vague intentions. How to build a personal rolodex so you stop relying on memory and luck. How to introduce yourself in a way that sparks curiosity instead of ending the conversation. How to walk into a room and insert yourself with ease, even when every instinct says to hang back. And how to follow up in a way that feels generous, not awkward. She also gets honest about what nobody tells you: that quality beats quantity every time, that some of your best networking moves are sitting in relationships you already have, and that you don't need to do more, you need to do it better. In this episode: * Why transactional networking doesn't work, and what intentional networking looks like instead * How to set quantitative networking goals and actually stick to them * Building your own networking rolodex (and why a spreadsheet is more powerful than it sounds) * The three things every strong networker does: intro, approach, follow-up * The follow-up formula that removes all the guesswork * Why nurturing the relationships you already have is still networking * How community, done right, becomes the most sustainable networking strategy there is If you've ever left an event with a stack of cards and zero real connections, this episode is your reset. New episodes drop every Monday. Ready to Cultivate? Hit subscribe. Learn more about Camp Collective [https://www.cnywomensnetwork.com/camp-collective] Follow Cultivate with Alex Canavan on Substack [https://substack.com/@cultivatewithalexcanavan] Follow Cultivate with Alex Canavan on ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.instagram.com/alexcanavanpodcast/] ⁠⁠⁠⁠Apply⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://docs.google.com/forms/d/e/1FAIpQLSevUSBdGbpTOBGXjuGNeY8PN6uNSKHWCJwKOS2SpsCtJ1WCaw/viewform] to be a guest on Cultivate Connect with Alex Canavan, the host of Cultivate on her ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠website⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.alexcanavan.com/], ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠LinkedIn⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.linkedin.com/in/alexcanavan/] & ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.instagram.com/alexcanavan.co/] This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Diam Media Group⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.diammedia.com/]

135: Timing is Never Going to be Perfect ft. Sarah Pelligrini

In this episode, host Alex sits down with Sarah Pellegrini — Syracuse native, real estate veteran, entrepreneur, and co-founder of Noble Cellar — for a conversation about what it really means to bet on yourself, bet on your community, and build something that didn't exist before you showed up. Sarah has spent over 20 years executing across real estate, sales, business development, and hospitality. She guided more than 600 families to achieve their real estate goals. She spent five years as Vice President of a national real estate coaching organization, mentoring hundreds of agents and business owners across the country. And then — in the middle of all of it — she co-founded Noble Cellar, a fine-dining restaurant inside a historic downtown Syracuse church that went on to earn Wine Spectator Awards, DiRōNA recognition, and Best Restaurant honors in its first two years. She didn't wait for the perfect moment. She didn't wait for the perfect space, the perfect plan, or the perfect time to come back home. She found a building that made her feel something — and she built the rest from there. Because timing is never going to be perfect. And Sarah Pellegrini is proof of that. 💬 Topics we cover: * What it takes to lead across industries — from real estate to fine dining — and the thread that ties it all together * Why she came back to Syracuse and what community investment really looks like in practice * What she learned coaching hundreds of business owners that most people never figure out * How she and her co-founder built Noble Cellar without investors — just vision, grit, and each other * What it felt like to be told fine dining would never work in Syracuse — and then prove them wrong * What she wants builders and leaders who are in the thick of it right now to hear If you've ever talked yourself out of something because the timing wasn't right — this is the episode you needed to hear. New episodes drop every Monday. Ready to Cultivate? Hit Subscribe. Connect with Sarah [https://www.linkedin.com/in/sarah-pelligrini-syracuse/] Learn more about Noble Cellar [https://www.noble-cellar.com/] ⁠⁠⁠Apply⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://docs.google.com/forms/d/e/1FAIpQLSevUSBdGbpTOBGXjuGNeY8PN6uNSKHWCJwKOS2SpsCtJ1WCaw/viewform] to be a guest on Cultivate Connect with Alex Canavan, the host of Cultivate on her ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠website⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.alexcanavan.com/], ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠LinkedIn⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.linkedin.com/in/alexcanavan/] & ⁠⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.instagram.com/alexcanavan.co/] Follow Cultivate with Alex Canavan on ⁠⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.instagram.com/alexcanavanpodcast/] This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Diam Media Group⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.diammedia.com/]

134: Whose Definition of Success Are You Living? ft. Barb Stone

In this episode, host Alex sits down with Barbara Stone — entrepreneur, author, TEDx speaker, leadership development coach, and founder of Build Your Path LLC — for a conversation about what it really costs to spend 25 years chasing someone else's version of success. And what it takes to finally walk away from it. Barb did everything right. She earned her MBA, climbed the ladder in manufacturing — one of the most male-dominated industries out there — and reached the top. Executive Vice President. CFO. Impressive by every measure. And then one day, she stopped and asked herself a question that changed everything: Whose definition of success am I actually living? What followed wasn't a clean, Instagram-worthy pivot. It was a reckoning. With identity. With worthiness. With the version of herself she had been performing for decades. Through the loss of her first husband, a kidney cancer scare, and living with alopecia — a condition that took her nearly eight years to stop hiding — Barb kept doing the inner work. Studying resiliency. Getting certified as a coach. And eventually, building a life that actually looks like her. In April 2025, she released her first book — So Much to Drool About: Lessons for Living Large — inspired by the Great Danes who taught her more about presence, courage, and showing up fully than any boardroom ever did. 💬 Topics we cover: * What it was like being a woman in manufacturing and learning to lead without losing herself * The moment she realized looking good and getting it right was killing her soul * What resilience actually means — and why it's about building forward, not bouncing back * How her Great Danes became the unexpected teachers behind her first book * The daily practices that keep her grounded, intentional, and moving forward * What she wants every quietly unfulfilled high-achiever to hear right now * Why the antidote to being stuck is simpler than you think If you've ever built a life that looks great on paper but doesn't feel like yours — this is the episode you needed to hear. New episodes drop every Monday. Ready to Cultivate? Hit Subscribe. Learn more about Barb Stone [https://barbstone.me/] ⁠⁠⁠Apply⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://docs.google.com/forms/d/e/1FAIpQLSevUSBdGbpTOBGXjuGNeY8PN6uNSKHWCJwKOS2SpsCtJ1WCaw/viewform] to be a guest on Cultivate Connect with Alex Canavan, the host of Cultivate on her ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠website⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.alexcanavan.com/], ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠LinkedIn⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.linkedin.com/in/alexcanavan/] & ⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.instagram.com/alexcanavan.co/] Follow Cultivate with Alex Canavan on ⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.instagram.com/alexcanavanpodcast/] This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Diam Media Group⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.diammedia.com/]