21st Century Entrepreneurship

• Patrick Wood: Why Every Entrepreneur Should Plan for Failure?

  Patrick Wood is a 30-year entrepreneur in finance and capital markets across Canada and the U.S., now leading an early-stage public company redefining how digital asset treasuries hedge risk. We spoke about what it really takes to endure the entrepreneurial grind — and why expecting failure can become your most powerful advantage.“Always plan on failure first,” Patrick says. “Expect it’s going to fail — then move, pivot, and adjust.” That mindset has guided his own journey, from stockbroker to CEO, through multiple pivots that turned potential collapses into breakthroughs. When his firm’s initial product for credit markets stalled, he leveraged the same structure to serve crypto treasuries — a small shift that unlocked major traction. “We accepted the fact it was looking like a failure and needed to act,” he reflects.Patrick explains that few founders win on their first try, or even their fourth. What matters is readiness — anticipating how to adapt when things break. “If it was easy to do what we do, everyone would be doing it,” he says. For him, entrepreneurship remains a strange but irresistible pursuit of freedom, responsibility, and self-governance.Listeners will come away with a pragmatic view of resilience — how to build flexibility, protect investors, and make smarter strategic pivots when the wind shifts.Key takeawaysExpect failure as part of the entrepreneurial process, not an exception.Build your plan two steps ahead — always know your pivot options.Leverage what already works instead of starting from scratch.Accept when something’s failing early to minimize damage.Freedom and self-direction outweigh comfort for true entrepreneurs.Collaboration with the right advisors accelerates smarter decisions.

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• Gail Kasper: How logic saves your business from emotion?

  Gail Kasper is an author, professional speaker, and performance coach who has spent over 15 years training entrepreneurs and executives—from solo founders to leaders in multi-billion-dollar companies—on leadership, customer service, and sales. We spoke about how few CEOs (only 15%) have ever been formally trained in sales, and why that missing skill often determines whether a business scales or stalls.Her approach centers on what she calls the Systematic Attitude Development Technique—a method to “get logical in the face of emotion.” As she put it, “When we get knocked down or face conflict, we go into emotion versus logic.” By planning ahead, setting priorities, and seeking help when stuck, entrepreneurs can shift from reaction to deliberate action. Gail outlines four core steps: make a daily list, prioritize the top three high-impact tasks, execute them, and ask for help when needed.She shares vivid stories, from a woman who escaped a car trunk by focusing on logic to her own moment of resilience the night before a major speech when her husband left. “If I stay in bed, I lose money, my client loses out—but I also let myself down,” she recalls. For Gail, logical follow-through isn’t cold—it’s confidence in motion.This conversation is a masterclass in staying rational under pressure, refining your sales message, and turning persistence into tangible progress—one logical step at a time.Key takeawaysOnly 15% of CEOs have formal sales training—yet it’s a critical growth skill.Use the Systematic Attitude Development Technique to stay logical under stress.Make a daily list, then focus on your top three high-impact actions.Ask for help—mentors and podcasts can break emotional deadlock.Strengthen your “power statement” to clearly express your unique value.“Check the fear box” weekly by doing one uncomfortable, growth-driven action.

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• Christopher Hossfeld: What can war teach us about leadership?

  Christopher Hossfeld is a 27-year U.S. Army veteran and leadership educator who translates battlefield decision-making into modern business strategy. We spoke about how lessons from military history can sharpen leaders’ thinking, reduce bias, and strengthen organizations. “Investing in your people is the best way of spending your limited resources,” he explains—because leadership, at its core, is about leaving something that transcends business.Through his Barrel Strength Leadership framework, Hossfeld helps leaders identify blind spots, challenge cognitive bias, and apply situational awareness to real-world problems. Using examples from Gettysburg to corporate boardrooms, he shows how “the military trains people not just for the job they have, but the job they’ll have next.” He teaches leaders to balance physical, emotional, mental, and spiritual “fuel tanks,” recognizing that stress in battle may mirror a year’s pressure in business.Rejecting classroom monotony, Hossfeld favors immersive experiences that create emotional connection and measurable ROI—returning 60 to 90 days later to assess what changed. His mission is simple: when leaders invest in their people, those people repay that investment many times over.Key takeawaysInvest in people as the most effective long-term organizational strategy.Translate battlefield decision-making into frameworks for business resilience.Identify and counteract cognitive bias before it shapes key decisions.Strengthen leadership by balancing physical, emotional, mental, and spiritual energy.Replace passive learning with emotionally engaging, action-driven experiences.Reassess leadership ROI through honest feedback 60–90 days after implementation.

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• Michael Jacobson: Can love and tech grow a $9M flower business?

  Michael Jacobson is the CEO who transformed a struggling flower shop into a thriving, multi-location enterprise generating over $9 million in revenue. We spoke about how he acquired a near-bankrupt business and rebuilt it by blending technology, artistry, and a mission grounded in love rather than profit. “Profit’s a great thing,” he said, “but it’s a means to our greater why.”Instead of chasing corporate slogans about being “number one,” Jacobson focused on culture, human connection, and elegant internal systems. Every designer now works from an iPad, with predictive inventory and automated logistics—yet “we don’t automate just to automate,” he explained. “We’re in the industry of love.” His team uses digital tools to remove friction, not feeling, ensuring that the client experience remains warm, fast, and deeply personal.Today, French Florist’s success has led to a growing franchise network—but its heartbeat stays human. “We send handwritten cards to first-time clients,” Jacobson shared. “Most would argue that’s not scalable. I beg to differ.” His story shows that scaling a company and scaling empathy can coexist when purpose drives the process.Listeners will walk away with a grounded playbook for growing culture, technology, and heart—together.Key takeawaysBuild profit as fuel for mission, not the mission itself.Use tech to remove admin pain, not human emotion.Automate only when it improves love-driven client experiences.Culture and team health shape customer experience from within.Handwritten gestures and empathy can still scale.Growth follows alignment of purpose, systems, and care.

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• Iñigo Rivero: How TikTok Converts Viewers Into Customers?

  Iñigo Rivero is the co-founder of House of Marketers and a former early TikTok Europe team member who helped transform the app from a lip-syncing platform into a global content powerhouse. We spoke about how he built a 50-person remote agency by turning short-form creativity into measurable results for brands.After leaving TikTok, Iñigo noticed that “brands didn’t know how to actually succeed on TikTok,” and decided to fill that gap. His journey began as a sales-driven professional who saw the potential of creator marketing before most. By pairing influencer storytelling with performance tracking—through “hybrid compensation models, coupon codes, and pixel-based attribution”—he helped brands convert curiosity into conversions.Rivero shares clear rules for success: hook viewers in the first three seconds using emotion and surprise, join trends early but adapt them to your brand voice, and treat TikTok as a search engine by using spoken and captioned keywords. As he puts it, “TikTok thrives on novelty, so keep evolving.”For entrepreneurs and marketers, his story offers a grounded blueprint: combine authenticity, agility, and analytics—and say yes when opportunity knocks.Key takeawaysHook viewers emotionally within the first three seconds.Join trends early and tailor them to your brand’s niche.Use captions and spoken cues to boost TikTok SEO visibility.Rotate influencers and formats to prevent audience fatigue.Track ROI with hybrid pay, coupon codes, and pixel attribution.Build trust by co-creating content with micro and nano influencers.

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