21st Century Entrepreneurship

Latest Episodes:

Jay Patel: Can 11% a year fund your retirement? Jan 16, 2026

Show notes

Jay Patel is a real estate fund manager and we spoke about why he pushes people to rethink defaulting to the stock market when planning retirement. He argues many investors want a better return with less risk, yet find real estate “too intimidating” and don’t want the “headaches of managing real estate,” especially dealing with tenants—so the real question becomes whether you can access real estate returns without becoming a full-time landlord.

We also talked about what drives his approach: capital preservation first, then dependable income, then legacy. Jay framed the planning problem bluntly—“do you have enough saved and do you have a plan?”—and pointed to the risk of retirees depleting savings as living costs rise. He shared his own hard lessons from big losses (“I was 23, 24, thought I knew everything, and I lost a million bucks again…”) and the rule he now lives by: “it’s not the product, it’s the person,” meaning you should scrutinize the operators behind any investment before you commit.

From there, Jay walked through a concrete retirement math example: if someone had $500,000 and could compound at 11% for a decade, it could grow to “almost 1.5 million,” creating roughly “$12 and a half, $13,000 a month consistently” in income without drawing down principal—leaving more to pass on to family. The practical value for listeners is a simple decision framework: prioritize preservation, understand where returns actually come from, and don’t “try to fake it”—either learn the game or find the right experts before you move.

Key takeaways

Don’t default to stocks; evaluate alternatives with lower risk.
Aim for retirement plans that preserve capital and generate steady income.
If real estate intimidates you, avoid tenant headaches via managed structures.
Vet operators closely: “it’s not the product, it’s the person.”
Use compounding math: $500k at 11% can approach $1.5M in 10 years.
Don’t fake expertise—educate yourself or find an expert before investing.

Sam Miles: How do you avoid IRS audits as an entrepreneur? Jan 14, 2026

Show notes

Sam Miles is a CPA, and we spoke about how entrepreneurs can legally reduce taxes while avoiding the small, preventable mistakes that trigger IRS audits. Drawing on years of audit defense and advisory work, Sam explains why “it’s not the spending of money that makes a tax deduction, it’s the context or the story,” and why documentation—not clever tricks—is what actually protects you as the IRS gets better at AI-driven matching.

We also talked about where most entrepreneurs get into trouble: unreported 1099 income, poor documentation, and not knowing their own numbers. Sam urges business owners to actively review their IRS transcripts, reminding listeners that “nobody knows your numbers like you do,” and that missing income is “the most common, easiest way to get audited.” He shares how CPAs read tax returns as stories—and why pushing your CPA to explain that story can reveal risks early.

Sam’s approach is grounded in ethics and realism. He breaks down practical tools like reasonable compensation, entity structure decisions, and why some popular strategies backfire when abused. As he puts it, “little pigs are cute, but hogs, they get slaughtered,” a reminder that aggressive shortcuts often cost more in time, stress, and money later. The episode closes with a clear message: do it right, document it properly, and use the rules as written.

Key takeaways

Missing 1099 income is the fastest path to an IRS audit
Check your IRS transcript to verify all reported income
Deductions depend on business context, not just spending
Documentation must be done before, not after, tax filings
Reasonable compensation protects S-corp owners in audits
CPAs read tax returns as stories—ask them to explain yours

Chris Kille: How did delegation save his life and business? Jan 13, 2026

Show notes

Chris Kille is a serial entrepreneur who exited multiple companies, and we spoke about how running everything himself nearly killed him—and why delegation changed everything. At his first exit, he was earning a few million a year but doing every job himself, until “they thought I had a stroke.” That moment forced a hard reset: if the business depends on the founder, it’s fragile, stressful, and worth far less than owners believe.

We talked through the practical method he learned the hard way: replacing yourself step by step. Chris explained why founders should offload admin first, then customer support, then marketing—before sales—so revenue doesn’t collapse under its own weight. He shared how documented workflows, SOPs, and clear expectations matter more than heroics, and why “80% done by somebody else is a hundred percent awesome” when it frees the founder to lead.

Chris also unpacked the deeper reason this matters. Removing himself from daily operations didn’t just increase valuation and exit multiples; it gave him his life back. As he put it, “Systems matter more than people,” because strong systems survive churn, scale without burnout, and protect what matters most—health, family, and time.

If you’re building a company that feels stuck, exhausting, or unsellable, this conversation offers a concrete blueprint for turning effort into leverage—and a business into an asset.

Key takeaways

Founder-dependent businesses get lower exit multiples
Nearly burning out forced delegation and change
Hire admin first, not sales
Document SOPs for every repeatable task
Strong systems outperform individual talent
Delegation creates time, health, and freedom

Kate Assaraf: Seven-figure growth without ads? Jan 09, 2026

Show notes

Kate Assaraf is an economist and founder, and we spoke about how she built a seven-figure, mission-driven business through word of mouth—without paid ads, influencers, or marketplaces. Her turning question was simple and risky: could a modern business grow purely through trust and real customers? She decided to prioritize direct relationships, email lists, and selective distribution, arguing that when platforms reward “the cheapest, the fastest,” the best products lose control of their customers.

Her core method was choosing community over algorithms. She explains that “customers are really, really smart” and can quickly spot “fake purchased authenticity,” which is why she avoided incentivized reviews and staged content. By staying off dominant marketplaces and refusing paid social, she protected margins, kept ownership of customer relationships, and leaned into face-to-face retail and grassroots discovery. As she puts it, “I chose to build my company with communities over algorithms,” even when that path was slower and harder.

We also talked about the mindset and structure required to sustain that choice: loving the product category enough to talk about it daily, protecting the business legally, and developing thick skin. Kate stresses learning to “shut your ears off to advice” when it doesn’t align, and using capitalism intentionally—what her team calls “Operation Big Check”—to fund causes customers actually care about. The result was unexpected media attention and awards that came from building differently, not chasing coverage.

This conversation offers a grounded playbook for entrepreneurs who want growth without sacrificing trust, margins, or purpose.

Key takeaways

Word of mouth can scale to seven figures without paid ads
Keep customers off marketplaces to control relationships and margins
Avoid fake UGC; real customers build faster trust
Choose selective retail over algorithmic distribution
Love your category enough to talk about it daily
Use profits intentionally to reinforce values and loyalty

Trevor McGregor: Why busy founders can’t scale? Jan 08, 2026

Show notes

Trevor McGregor is a high-performance coach and CEO, and we spoke about why so many entrepreneurs feel burned out, misaligned, and trapped by the businesses they built. After “over 45,000 one to one coaching sessions,” Trevor has seen the same patterns repeat: founders hustling harder, short on time, and unsure what they’re even optimizing for anymore.

He breaks this down into five concrete blockers to scale: limiting beliefs, no clear strategic plan, missing systems, poor time management, and weak execution. Trevor explains why “most people spend more time planning their vacation than they do their business and their life,” and how reverse-engineering a clear short-, mid-, and long-term plan changes momentum. From there, he emphasizes building systems that support daily action, optimizing what to do, delegate, or drop, and taking “intelligent and inspired action” instead of reactive busyness.

We also talked about his core framework—the four S’s: state, story, standards, and strategy—and why mindset is the real lever behind results. Drawing from his work with Tony Robbins and clients like Joe Fairless, Trevor shows how owning your inner state and standards can unlock financial, time, and location freedom, all in service of impact and legacy. Listeners will leave with a clear picture of what actually drives scale—and what to fix first.

Key takeaways

Burnout comes from hustling without clear goals or priorities.
Identify and dismantle limiting beliefs before scaling.
Create a strategic plan, then reverse-engineer daily actions.
Systems and support make growth sustainable.
Optimize time: do, delegate, or dump tasks.
Execution requires intelligent and inspired action.

Scott Abbott: How systems turn chaos into scalable growth? Dec 30, 2025

Show notes

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 takeaways

Scale speed with discipline, not hustle alone
Use agreement-based commitments to reduce fragility
Combine systems with grace for individual style
Work on and in the business intentionally
Choose harmony over unrealistic work-life balance

Scott Kelly: What actually gets a yes from investors? Dec 27, 2025

Show notes

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 takeaways

Build investor relationships long before you ask for money
Target investors by industry and company stage
Maintain a network of at least 100–200 qualified investors
Pitch decks must answer problem, solution, market, team, and exit
Expect many no’s and keep updating investors with traction

Rob May: When should you stop using just one AI model? Dec 20, 2025

Show notes

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 takeaways

Stop 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: How did he recover after losing $50M? Dec 16, 2025

Show notes

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 takeaways

Reset 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: How do you become employer of choice? Dec 10, 2025

Show notes

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 takeaways

Culture 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.

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