21st Century Entrepreneurship

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.

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.

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.

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.

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.

Brennan Haelig is a digital marketer turned agency owner, and we spoke about going from sleeping in a 10×10 studio to leading a multi–seven-figure team of 18. “Back in 2018, I was homeless, sleeping in my recording studio,” he recalls, adding, “I remember having 50 cents in my bank account.” The early aim wasn’t millions—it was simply to support himself without “a full time corporate job.”His turning point came when he was let go from a part-time day job and had to go all-in. Growth followed once he built dependable deal flow—first by mining Upwork for steady, qualified leads—and focused on what matters: deals closed, ROI, and CAC, not clicks. As he puts it, “lead gen and deal flow pretty much solves all of the problems.” Practically, that means one scalable channel (then more), paid ads (Meta/Google/LinkedIn) feeding a CRM, and an integrated dashboard (APIs/Zapier) tracking cost per appointment, pipeline stages, and payback—aiming for month-one revenue to exceed 2× acquisition cost.We also unpacked the messy shift from freelancer to owner: hiring fulfillment before sales replacement, keeping standards high, and learning to delegate. A mentor taught him “knowing when to drop the ball” so the team picks it up, while Brennan admits entrepreneurship often requires “manufactured self confidence.” The why stayed constant: prove he could stand on his own and build something that lasts.In short, this conversation gives a concrete system—lead flow first, metrics that matter, and staged delegation—to move from $20k months toward $200k and beyond.Key takeawaysBuild one scalable channel; Upwork drove ~100 leads/month.Replace vanity metrics with deals closed and ROI dashboards.Ask first: “How many clients do you want?”Ensure month-one revenue exceeds 2× customer acquisition cost.Practice delegation: occasionally “drop the ball” so teams learn.Lead flow and hiring are twin levers from $20k to $200k.

Kyle Whitehill is a former Vodafone executive who spent three decades inside global giants like L’Oréal, Diageo, and PepsiCo before asking himself, “Am I not entrepreneurial?” Seven years ago, he found out—leaving the corporate world to lead a smaller, founder-built company and test whether discipline and responsiveness could thrive in an entrepreneurial environment.He explained that his leadership philosophy rests on four pillars: responsiveness, authentic purpose, governance, and accountability. “To engage customers effectively, you have to be responsive,” he said, adding that purpose must be “authentic, not just charity.” In practice, that meant creating initiatives like Project Heart, connecting 300,000 schoolgirls in rural Kenya to digital education and refugees in East Africa to vital communication tools.Whitehill’s stories reveal what happens when founders don’t know when to let go—or when corporate leaders forget to sell. “There comes a moment when the founder must yield leadership,” he noted, “so the company can professionalize and grow.” His insights bridge both worlds: how to keep the agility of a startup with the discipline of a corporation.For listeners, this episode offers a real-world roadmap for scaling responsibly—balancing entrepreneurial spirit with the systems that sustain it.Key takeawaysFounders must know when to hand leadership to experienced operators.Responsiveness builds trust faster than perfection or hierarchy.Authentic purpose drives engagement more than profit goals.Governance enables agility when aligned with a clear mission.Large companies can’t fake entrepreneurship—they must empower it.Passion without monetization risks the survival of great ideas.

Alex Mehr is a scientist-turned-entrepreneur who built and sold companies generating over a billion dollars in revenue. We spoke about how the speed and accessibility of AI have fundamentally changed what it means to be an entrepreneur today. “The best thing you can do is to become an idea machine,” he says — because execution cycles are now so fast that markets reward creativity and adaptability over long-term focus on a single idea.He calls this new model the “one-two punch”: first, turn an idea into an MVP as fast as possible; second, go to market just as rapidly. His own journey — from NASA scientist to co-founder of one of the world’s top-grossing dating apps — illustrates this principle. “Every time I played the mad scientist, I made progress,” Mehr explains. “Every time I deviated because the world told me otherwise, I lost.” That pattern, he adds, has only intensified with AI.Mehr urges founders to embrace experimentation, even chaos, as a strength. “The greatest conquerors could hold two opposing thoughts at once,” he notes, linking adaptability to tenacity — the ability to switch strategies fluidly. He now channels this mindset into empowering new entrepreneurs to transform blurry ideas into tangible products, fast.Listeners will leave with a concrete framework for thriving in the AI-driven startup era — where creativity, speed, and continuous experimentation matter more than ever.Key takeawaysAI erased traditional moats — speed and creativity now win.Write ten ideas daily to train your “idea muscle.”Build MVPs fast, then test them in the market immediately.Treat entrepreneurship like science: hypothesize, experiment, adjust.Adapt strategy constantly — “be like water, my friend.”Luck favors motion: keep building, iterating, and learning.

Zylo Marshall is a disability advocate and former real estate professional who built a life beyond government support. We spoke about how people with disabilities can pursue commission-based careers—like real estate or public speaking—without losing crucial benefits such as SSI. Zylo explains that “just because someone says no does not mean you stop trying,” emphasizing persistence and structured planning over dependence.After years of navigating complex disability and employment rules, Zylo developed a model based on gradual, legal income transitions. “If I get paid $3,000 on a house, they’d give me $1,000 a month, allowing me to stay within SSI rules,” he explains. His insight comes from personal experience—passing his real estate exam after four tries, relying on paratransit for mobility, and creating a website listing code-violation properties to connect investors and communities.For Zylo, the message is clear: success for disabled professionals requires mentorship, legal awareness, and collective advocacy. “If the disabled get together and want to become independent, they’ve got to go to legislation,” he says. This conversation shows how independence can be built one ethical, structured step at a time.Key takeawaysRejection is part of progress—persistence matters more than approval.Commission-based work offers flexible income paths for disabled individuals.Gradual payment structures can protect SSI eligibility.Mentorship from lawyer-brokers helps navigate legal and financial risks.Real estate with code-violation listings can be an accessible business model.Advocacy is key to reforming outdated disability income laws.

Mark Lee Fox is a former Space Shuttle chief engineer who spent over 16 years at NASA before an unexpected event set him on a new trajectory. “My dog couldn’t come up the stairs one day,” he recalls, describing the moment that led him to explore energy-based healing technologies. Initially skeptical—“I’m a rocket scientist, so I thought that can’t be true”—Fox discovered that NASA had used pulsed electromagnetic fields (PEMF) since the 1970s to counter bone loss in space.Driven by both scientific curiosity and compassion, he spent years learning how energy transfer can recharge the body’s cells. As he explains, “When your cell voltage gets low, you get sick. This recharges your cell’s batteries.” His mission became to make this technology portable and affordable, transforming bulky clinical machines into pocket-sized devices that deliver therapy through low-frequency electromagnetic pulses.Fox’s work has expanded beyond pets to people, veterans, and first responders. “We’ve donated a lot of these to the military for PTSD,” he says, citing a 98% independent success rate. His broader goal is accessibility—whether through wearable devices, smart light bulbs, or someday, even smartphones that can deliver healing energy.Listeners will gain a rare perspective on how aerospace principles can inspire new healthcare frontiers—and how compassion, science, and persistence can turn skepticism into global impact.Key takeawaysHow NASA’s PEMF research inspired portable healing technologyWhy energy transfer and cell voltage are keys to recoveryWhat makes portable therapy easier than traditional treatmentsHow trauma and PTSD patients respond to noninvasive energy therapyThe real challenge of scaling health tech: marketing costs, not scienceWhy Fox dreams of turning every smartphone into a healing device