21st Century Entrepreneurship

Scott Abott is the founder and CEO of BOS-UP, a three-time bestselling author, and a former EY Entrepreneur of the Year finalist. He is a systems implementer and early-stage investor, and we spoke about why structure—not hustle alone—is what actually allows companies to grow. After decades in ERP, SAP, and Oracle environments, and after building (and overbuilding) his own ventures, Scott learned the hard way that speed without discipline creates fragility. As he put it, “Be quick, but don’t hurry,” a lesson earned after raising millions, scaling too fast, and realizing how much he didn’t yet know.We unpacked his core method: combining entrepreneurial energy with clear agreements, simple operating rules, and shared language. Scott explained how alignment comes from fusing systems with humanity—“agreement-based commitments” paired with grace for individual style—so teams can be confident, resilient, and adaptable. He emphasized that antifragility isn’t about control, but about clarity: vision, values, roles, metrics, and communication that keep everyone on the same page.We also talked about leadership, mentorship, and harmony over balance. Scott reframed growth as learning to “work on and in the business” using concepts, tools, and discipline—plus reflection and self-awareness. His why is practical and human: helping founders, teams, and communities avoid unnecessary pain, save time, and build something that benefits “both the company and the individual.”Listeners will walk away with a grounded way to scale—one that protects energy, improves decisions, and makes growth feel sustainable rather than chaotic.Key takeawaysScale speed with discipline, not hustle aloneUse agreement-based commitments to reduce fragilityCombine systems with grace for individual styleWork on and in the business intentionallyChoose harmony over unrealistic work-life balance

Scott Kelly is a veteran venture investor and advisor, and we spoke about what it really takes to raise capital after decades on both sides of the table. With 35 years in venture, multiple exits, and billions raised, Scott has seen where founders consistently get it wrong—and what actually moves investors to say yes.At the center of his approach is preparation and relationship-building. He explains why “running your startup is a full time job and raising capital is a full time job,” and why shortcuts don’t work. Instead of blasting pitch decks, Scott stresses building a vetted network—“a minimum of 100 to 200 people”—who invest in your industry and stage, then earning the right to pitch through real engagement.We also break down what investors expect when you finally get the meeting: a clear problem, a differentiated solution, a capable team, real competition awareness, a credible exit path, and a precise plan for how the money will be spent. Scott is blunt about resilience, reminding founders that rejection is part of the process, and that sometimes “the best raise, the way to raise capital is go sell something” before chasing investors.This conversation gives founders a grounded, no-nonsense roadmap for raising capital without wasting time, burning relationships, or fooling themselves about what investors actually look for.Key takeawaysBuild investor relationships long before you ask for moneyTarget investors by industry and company stageMaintain a network of at least 100–200 qualified investorsPitch decks must answer problem, solution, market, team, and exitExpect many no’s and keep updating investors with traction

Rob May is a serial founder (five startups) and we spoke about how he went from “I did not intend to go do a fifth” startup to building a new AI company after he “stumbled upon an AI idea” he could prove out—and couldn’t ignore. He’s been focused on AI since 2015 (after exiting his first company in December 2014) and framed the current moment simply: even “10 years later… we are still just at the beginning” of what’s coming.Rob walked through the real path to his current thesis: early bets, being “a couple years too early” pre-LLM, and a short venture-capital chapter that was “very intellectually stimulating,” but ultimately he missed “the battleground” of building and winning in-market. That experience shaped the core idea of the episode: most teams start with one big model, then hit the same wall—cost, speed, and inconsistent outputs—because models are probabilistic. As he puts it, “if you ask the same question multiple times, you might get different answers,” which is why techniques like Best-of-N (ask the same question 10 times) can reveal a distribution and help you avoid weak one-shot results while you decide what should run where.If you’re building with AI, this conversation gives you a concrete way to think about splitting work across multiple models, when you actually need a frontier model, and how small process changes (like repeated probing) can improve reliability without rewriting your whole product.Key takeawaysStop routing everything to one model; match model strength to task type.Use Best-of-N: ask 10 times, inspect outputs, choose the best.One-shot outputs can vary; plan for probabilistic behavior.Keep complex, variable tasks on frontier models; offload narrow tasks to smaller ones.Validate ideas fast; being “too early” is real in AI product timing.Optimize for accuracy, speed, and cost together by splitting workloads.

Rod Khleif is a real estate entrepreneur and educator, and we spoke about how he rebuilt after losing $50 million during the 2008–09 crash—and the mindset that allowed him to have $50 million to lose in the first place. Growing up as an immigrant with little money, Rod watched his mother quietly build wealth through real estate, which pushed him to choose that path early and scale fast.The turning point came when rapid success fed ego, followed by a brutal correction. Rod calls it “a $50 million seminar,” and explains that recovery didn’t start with tactics, but with psychology: “80 to 90% of your success in anything is just that, your mindset and psychology.” Instead of obsessing over the loss, he reset his focus, reminding himself that “whatever you focus on gets bigger,” and deliberately re-anchored on goals, decisions, and daily action.We also broke down the practical structure behind that comeback: aggressive goal setting, making a non-negotiable decision (“motivation will get you started, but… commitment is what brings you home”), taking the first imperfect step, and surrounding yourself with peers who raise your standards. Rod shared how identifying limiting beliefs as “B.S.”—belief systems with no factual basis—helped him replace fear with momentum.This conversation is a grounded playbook for anyone facing a setback and wondering how to rebuild clarity, confidence, and forward motion without waiting for perfect conditions.Key takeawaysReset focus quickly; what you focus on expands.Set goals first, then define why they matter.Make a full decision—no halfway commitment.Take the first step before seeing the whole path.Expose limiting beliefs as unfounded assumptions.Choose peers who normalize higher standards

David Deane-Spread is a former military and law-enforcement leader who built a decades-long career helping organizations turn cultural dysfunction into alignment, resilience, and performance. We spoke about how he applies the same persistence that kept him “fully booked without marketing for 20 years” to transform leadership teams and entire companies.His approach centers on what he calls the ABC practice of leadership—attitudes, behaviors, and conversations—which he says are responsible for every persistent workplace problem: “The right leader failed to have the right conversation with the right person at the right time.” By training leaders to choose better attitudes, replace unhelpful habits, and learn through difficult moments, he shifts companies from blame and avoidance to cohesion and adaptability. He describes the cultural inflection point as the moment leaders realize “followers are equally important,” which unlocks collaboration and removes fear-based behaviors.David also shared concrete stories, including helping a struggling company become a finalist for employer of choice and then secure a $100M equity injection after aligning its top three leaders. His work extends to individuals in crisis as well—when doctors send him suicidal veterans, he reframes their value by asking them to “pay it forward,” a step he believes restores purpose and agency.This conversation offers a practical blueprint for transforming leadership culture in months, not years, grounded in simple human behavior rather than complex systems.Key takeawaysCulture shifts when leaders value followers equally to themselves.Persistent problems reflect missing or mistimed leadership conversations.Attitudes, behaviors, and conversations form a repeatable leadership system.Fear, habits, and ignorance drive most workplace conflict and errors.Culture change can happen in months with full-team alignment.Paying value forward restores purpose in individuals facing crisis.

Jake Stahl is a psychology-trained communication strategist, NLP master practitioner, and global trainer who has coached over 10,000 people across six countries—and we spoke about how people actually make decisions. His core premise is simple: every person has two profiles, the polished public one and the internal one “that responds to fear and biases and happiness,” and only that second profile makes decisions. Jake teaches leaders, founders, and sales teams how to communicate directly to that internal profile by learning to recognize the caption someone is “saying without saying.”A turning point in his work came from moments like a Zoom call where a prospect outwardly showed interest but subconsciously signaled discomfort by twisting her wedding ring. Jake noted that “her voice was saying we want to do business, her caption was saying you touched a scar,” which forced him to reframe on the spot. His method is a structured process—recognize the signal, identify the trigger, and reframe the moment—to regain trust and “own the room.” He applies the same lens to CEOs who look away, tap their pen, or turn their feet toward the door; every signal is data, and his rule is clear: call it out, never ignore it.Practically, Jake breaks communication into micro-behaviors that shape presence long before words do. He explains why “confidence is the precedent to results,” not the reward, and why people fail when they wait to feel ready. He also offers concrete tools—like the three elements of a trustworthy headshot: a genuine smile, upright or forward posture, and a slight head tilt that subtly signals trust.For anyone who wants to become unforgettable instead of overlooked, Jake’s approach provides a step-by-step way to read signals, control presence, and communicate to the part of people that actually decides.Key takeawaysSpeak to the internal profile that makes real decisions.Read subtle signals: gaze shifts, pen tapping, foot direction.Call out signals directly to regain attention and trust.Recognize triggers and reframe quickly to save the interaction.Build confidence through micro-behaviors, not results.Use headshot cues—smile, posture, head tilt—to pre-signal trust.

Peter Maher is the U.S. expansion lead for Ovanti—recently rebranded as Flote—and we spoke about why he left a stable, well-paid role in fintech leadership to build an alternative to what he calls a “very, very broken” credit system. With 12+ years in payments, partnerships, and market launches, he brought a career’s worth of operational and commercial experience to a problem he personally lived through.Maher’s motivation is rooted in his early setbacks. A single poor decision at 19 “cost me the better part of the next 10 years,” teaching him that a traditional credit score can deny people opportunities even when their real financial behavior is healthy. He argues that “credit score is not an indicator of affordability,” especially for the half of U.S. adults—gig workers, young earners, and credit-averse consumers—locked out of conventional financing.That belief underpins Flote’s model: instead of backward-looking credit data, they use linked bank accounts, real-time cash-in/cash-out analysis, and account-age patterns to understand someone’s actual financial stability. As Maher puts it, they assess consumers based on “the financial health or situation that they’re in now, not a snapshot of the past 10 years of their life.”He also detailed the realities of building a responsible lending infrastructure from scratch—earning trust in a market full of failed promises, making daily build-versus-partner tradeoffs, and convincing institutions to back a new underwriting model. Maher relies on endurance principles: don’t “boil the ocean,” focus on the next milestone, and keep the mission front and center for a small team wearing multiple hats. For him, the ethical imperative is clear: “Innovation does not have to mean exploitation.”Listeners will walk away with a concrete understanding of why affordability-based underwriting matters, how Flote’s model works in practice, and what it truly takes to build credibility in modern financial services.Key takeawaysReal-time cash flow often predicts affordability better than credit scores.Many gig workers are excluded due to inconsistent employment data.One financial mistake can suppress traditional credit scores for years.Building trust requires transparency after years of false industry promises.Focus on the next milestone instead of the entire long journey.Strong past relationships accelerate early-stage partnerships.

Jeff Abraham is an entrepreneur who retired after selling a semiconductor engineering company, and we spoke about how he later built a sexual wellness brand by using medical credibility instead of hype. He explained that “even in healthy couples, the average man finishes in 5 minutes and 40 seconds” while “the average female takes 18 minutes,” a difference he called “the arousal gap.” Rather than compete with “197 products online—shark fin, deer antler extract,” he chose to power statistically significant clinical trials and have board-certified experts speak for the results.He said that the turning point came from listening to customers, educating doctors, and refusing to rely on embarrassment or gimmicks. As he put it, “people said, is that an educational site or are you trying to sell product? I said both,” because correct dosing and informed use drive repeat outcomes. He also shared how leadership means joining employees “changing these labels” and spending hours in live chat to hear exactly how buyers discover solutions and what obstacles they face.For listeners, his story shows how data, humility, and customer understanding can outperform shortcuts and noise—especially in markets filled with stigma and misinformation.Key takeawaysUse clinical proof to differentiate in crowded, distrustful marketsEducate customers so correct use drives repeat resultsListen to buyers to shape products and messagingEarn credibility through real experts, not stock imageryLead by working alongside employees and customersPlan exit strategy early: joint venture or acquisition

AJ Cassata is an entrepreneur who has spent more than a decade building companies using one core mechanism—outbound lead generation. We spoke about why so many founders struggle with lead flow and how, as he says, “leads are the lifeblood of your business,” yet most assume they need ads, a large audience, or influencer status to grow.His turning point was realizing that targeted outbound—“starting conversations with your target market at scale”—can outperform paid channels when done with precision. AJ walked through his three-step Repeatable Revenue Method: identify the exact ICP, message them directly, and follow up fast. Throughout our conversation he stressed specificity, noting that if you aim broadly, “you’re going to be so generic that you’re not really going to speak to anyone.” He also broke down why cold email must be treated as a one-to-one conversation, not a broadcast, and why the goal is simply to “pique their interest… and move them to the next step.”AJ shared the practical side too: how tools like Instantly can build lists, verify emails, and automate simple 2–3 step sequences so that outreach runs in the background. He emphasized that outbound works because it’s low cost, targeted, and quick to activate, saying you don’t need to be a tech expert—“within half a day” you can have a list, write templates, and have campaigns sending.For anyone looking to fill their pipeline without ads or a big audience, this episode offers a simple, proven structure you can begin using immediately.Key takeawaysLeads grow fastest when outreach is targeted to one clear ICP.Cold email works best as a short, conversational opener.Avoid selling in the first email; invite interest instead.Fast follow-up dramatically increases response likelihood.Build lists using proper databases, not generic purchased lists.Use cold-email-specific tools to protect deliverability.

Paul Cecil is the VP of Strategy at realpha and we spoke about how a young founder-minded strategist thinks through scale, pressure, and the role of AI in real business results. He began as a pre-med student, switched into business after realizing he “liked trading stocks a lot more,” and later worked for years without pay to learn capital formation. Joining realpha as employee number ten, he helped drive seven acquisitions, eight capital raises, and a NASDAQ listing in under three years.A key turning point for him was understanding what it really means to consider going public. As he put it, you must be “ready to figuratively get naked in front of the public,” with every detail, from lawsuits to losses, made visible. And once public, you “live and die by the quarter,” with pressure coming from every direction—yet that transparency unlocks credibility, national exposure, and new capital options such as ATM offerings that can provide next-day liquidity.We also discussed strategy in an era where AI acts as both leverage and potential customer. Internally, his team reduced week-long research cycles to “20 to 30 minutes,” allowing faster iteration and clearer decisions. He contrasted this lived experience with reports claiming AI yields no results, calling them “noise” compared to the signal he sees daily. He also argued founders must prepare for a future where AI agents—not humans—will evaluate products, make requests, and perform consumer tasks.Paul’s approach is shaped by a philosophy he learned from the book There Is No How: people chase prescriptions instead of clarity. By removing the “how” question and drawing insight from unexpected experiences—from guitar to skydiving to a six-day phone-free hike—he found sharper intuition about what to build, with whom, and when.Listeners will walk away with a grounded view of public markets, AI leverage, and strategic clarity in a world moving faster than ever.Key takeawaysGoing public demands full transparency and constant quarter-to-quarter pressure.ATM offerings give public companies flexible, immediate capital access.AI compresses research work from a week to under 30 minutes.Founders must design products for both humans and future AI agents.Strategy improves when you stop seeking prescriptions and focus on clarity.Non-work experiences can sharpen strategic thinking.