21st Century Entrepreneurship

Adam Cerra is a high-ticket sales expert who has closed more than $30 million in offers for coaches, consultants, and entrepreneurs. We spoke about how he teaches people to “sell without selling” — a process he calls inverse closing, where persuasion is replaced by empathy and guided conversation.As Adam puts it, “You’re not convincing anyone to buy anything. You’re getting your prospect to sell themselves for the offer.” His approach hinges on emotional intelligence — the ability to feel what the prospect feels — and on asking well-crafted questions that uncover the real voids, fears, and desires driving a decision. Instead of pitching, he trains entrepreneurs to listen deeply and lead with presence.In his work, he blends control with compassion: “Always be closing” meets “sales as a service.” Through his academy and agency, Adam helps others practice this method live — recording calls, reviewing tone and timing, and developing the confidence to turn authentic dialogue into high-value results. One student, a therapist once charging $200 an hour, closed her first $7,777 offer just weeks after applying his process.Listeners will walk away understanding how selling becomes effortless when it becomes human — and how emotional intelligence remains the edge AI can’t replace.Key takeawaysSelling starts with empathy, not persuasion.Let prospects “confess” their problems through guided questions.Use three core questions to bypass logic and access emotion.Emotional intelligence is what keeps sales human in the AI age.Combine control and care — authority without pressure.Record and review real calls to refine your tone and flow.

Dwan Bent-Twyford is one of America’s most recognized real estate investors and educators, known for turning a $75 setback into a multimillion-dollar career. We spoke about how losing her home and car as a single mother became the catalyst for a 35-year journey and over 2,000 completed property deals.Her approach begins with empathy, not transactions. “People before profits,” she said, describing how she focuses on homeowners in distress—those facing foreclosure, divorce, or loss—rather than chasing market trends. Dwan teaches students to “stop thinking about the deal and think about the person,” offering free options first, such as loan modifications or short sales, to build trust and long-term opportunity.She warns newcomers against “shiny object syndrome” and stresses finding mentors whose “moral compass aligns with yours.” For beginners, she suggests wholesaling—“the path of least resistance”—as the simplest way to earn while learning. Financial freedom, she reminds us, “is not just about money—it’s about being able to take time for your family.”This episode offers a grounded, no-fluff look at building lasting wealth by leading with compassion and practical action.Key takeawaysStart by helping people in distress—profits follow purpose.Ignore market panic; focus on real human circumstances.Offer free solutions first to build credibility and trust.Avoid “shiny object” shortcuts and learn proven basics.Align your values with your mentor’s moral compass.Begin with wholesaling for quick wins and lower risk.

John Frost is the Vice President of Enrollment Management and Marketing at Doane University with nearly 20 years in higher education across community colleges and private and public universities. We spoke about what it truly means to change lives through learning—and why education is not just for the gifted but for anyone curious enough to start.Frost believes that “what we do is what politicians, kings and queens promise to do—we change lives each and every day.” His approach goes beyond academics: it’s about helping students connect their personal dreams to real-world impact. From undergraduate to graduate programs and the Open Learning Academy, Frost emphasizes fundamentals, hands-on experience, and early exposure. “We don’t wait until senior year—we start career planning in freshman year,” he says, ensuring that students learn to apply knowledge through internships and community engagement.He challenges every prospective student with four questions: What is this worth? How will you do it? Are you willing to be a hero? Can you say yes every day? For Frost, success depends on understanding your why. “If you understand your why, then you can figure out the can,” he explains—a mindset that transforms education into both a personal and social mission.This episode offers a grounded reminder that education is not about status—it’s about commitment, courage, and the willingness to keep saying yes when it’s easier to say no.Key takeawaysEducation changes lives by connecting personal dreams with real-world action.Curiosity matters more than academic or athletic talent.Start internships and career planning as early as freshman year.Ask yourself four questions: worth, how, hero, yes.Understanding your “why” helps you persist when things get hard.Higher education is for everyone willing to commit and stay curious.

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.