The Challenging Sales! Podcast is a space where we talk with other founders like yourself about what worked, what didn’t, and what challenges they foresee in the ever-changing world of B2B sales.
This is an honest, founder-to-founder conversation. The kind that happens when peers gather around a table to talk about what truly matters. No scripts. No gurus. Just real experiences, lessons learned, and beliefs challenged.
Hosted by LeO Requena, Challenging Sales! explores the emotional and tactical sides of selling through authentic stories, tested insights, and moments of self-reflection.
Hosted on Acast. See acast.com/privacy for more information.
The Challenging Sales! Podcast is a space where we talk with other founders like yourself about what worked, what didn’t, and what challenges they foresee in the ever-changing world of B2B sales.
This is an honest, founder-to-founder conversation. The kind that happens when peers gather around a table to talk about what truly matters. No scripts. No gurus. Just real experiences, lessons learned, and beliefs challenged.
Hosted by LeO Requena, Challenging Sales! explores the emotional and tactical sides of selling through authentic stories, tested insights, and moments of self-reflection.
Hosted on Acast. See acast.com/privacy for more information.
In this episode of Challenging Sales!, host LeO Requena sits down with Daniel Ponce, CEO of City Troops, to unpack how a technical founder who once hated selling became the main salesperson of his company.
We talk about the early days of walking trade fairs with a suitcase, feeling like the cliché annoying salesman, and how that discomfort pushed Daniel to rethink what sales really is. He shares how he moved from looking for step by step recipes in San Francisco to treating sales as the best social skill a founder can learn. You will hear why the CEO must be the best seller at the beginning, not to push product, but to validate, listen and find real product market fit.
We also go into how to sell when companies are risk averse and prefer big names like Salesforce just to feel safe. Daniel explains how City Troops competes through service, relationships and honest qualification. We talk about the cost of saying yes to the wrong clients, how to niche down and why sometimes the most profitable move is to walk away.
Finally we explore rejection, consistency and authenticity. Daniel shares how his team “collects nos” so rejection becomes data and muscle, why many deals need 13 or more interactions to close, and why his final advice is simple. Be natural. Be truthful. Be yourself. Do not sell smoke. People are not only buying your product. They are buying your beliefs.
Listen if you want to:
Host: LeO Requena
Guest: Daniel Ponce, CEO of City Troops
Hosted on Acast. See acast.com/privacy for more information.
In this episode of Challenging Sales!, host LeO Requena sits down with Diego González Castellanos, CEO of Galilei Learning, to uncover the raw truth behind courage, discovery, and resilience in startup sales.
From conducting 20 discovery calls before building a product to showing up in person to win corporate conversations, Diego shares how he turned insights into action and action into opportunity.
You’ll learn why showing up matters more than automation, how 60 seconds of bravery can transform your comfort zone, and what it really takes to connect with people in a noisy market. This episode is a playbook for any founder learning to sell without fear, start without a product, and move faster through uncertainty.
Listen if you want to:
Host: LeO Requena
Guest: Diego González Castellanos, CEO of Galilei Learning
Duration: 01:08:05
Hosted on Acast. See acast.com/privacy for more information.
In this episode of Challenging Sales!, host LeO Requena sits down with Juan Miguel Román Roig, COO of tuGerente, to explore how belief, boundaries, and balance shape B2B sales.
From learning who not to sell to, to mastering follow-ups in Mexico, Juan Miguel shares how tuGerente grew from Bolivia to Peru and Mexico by refining its ideal client profile and focusing on data-driven decisions. He explains how the SPIN Selling framework helped them ask better questions and stop assuming what clients really need.
You’ll learn why saying no can accelerate growth, how to run consultative sales calls that build trust, and what
works when selling in competitive markets like Mexico. Juan Miguel also shares how he handles burnout and keeps clarity through sports, discipline, and self-awareness.
Listen if you want to:
Host: LeO Requena
Guest: Juan Miguel Román Roig, CCO of tuGerente
Hosted on Acast. See acast.com/privacy for more information.
In this short teaser, host Leo Requena introduces Challenging Sales! a podcast built for founders who believe that selling is not just a skill but a personal journey. Leo shares the core beliefs driving the show: that founders can and should become their best salespeople, and that growth starts by stepping outside the comfort zone.
You’ll hear what to expect from each episode: honest conversations with other founders about what’s working, what’s not, and the challenges they face in today’s shifting B2B sales world. Expect fresh perspectives, real founder stories, and practical insights you can apply right away.
If you’re ready to challenge how you think about sales, subscribe now and join us on the journey.
Hosted on Acast. See acast.com/privacy for more information.