Surviving the Side Hustle

Rob Tracz
  • 4.8 (22)
  • ENTREPRENEURSHIP
  • UPDATED WEEKLY

Welcome to "Surviving the Side Hustle," the ultimate podcast for balancing the demands of entrepreneurship with maintaining mental, physical, and emotional well-being. Hosted by Coach Rob Tracz, an expert in helping driven professionals achieve 'personal development for professional success,' this show is more than just storytelling—it's a masterclass in thriving amidst the entrepreneurial grind. Each episode features candid conversations with leaders who are rewriting the rules of entrepreneurship, sharing their unique stories, the creative solutions they're offering, and the everyday challenges they’re overcoming. Whether you’re a side hustler looking for your big break or an established entrepreneur seeking fresh perspectives, "Surviving the Side Hustle" provides valuable insights that resonate with the movers, the shakers, and everyone in between. Feeling burnt out and sidelining your own health? This podcast empowers you to overcome stagnation, build resilience, and optimize your life and business. We dive deep into your goals, identify obstacles, and share strategies to boost your energy, improve your strength, and keep the entrepreneurial grind enjoyable. Join us for inspiring stories, expert insights, and practical advice to help you look good, feel good, and do great things at every stage of your entrepreneurial journey. Let’s not just survive the side hustle—let's master it.

  1. 15H AGO

    E163 - The Psychology Shift with Kennedy

    This week on Surviving the Side Hustle, I sat down with Kennedy — former mind-reading comedian turned email marketing strategist — to unpack one of the biggest myths in online business: Growing your list isn’t the problem.Converting it is. Kennedy’s journey from global performer to founder of Email Marketing Heroes is a masterclass in reinvention, leverage, and understanding human psychology. The Core ProblemMost skill-built entrepreneurs are great at their craft.But when it comes to business, they focus on the wrong metric. They chase followers.They chase subscribers.They chase audience growth. And they “nurture” forever. Meanwhile…Revenue stalls. Kennedy learned this the hard way — not in marketing — but on stage. When you’re performing mind-reading comedy with real jeopardy (yes, literal staple guns), you either get it right… or you lose credibility fast. High consequence creates fast skill development. And that same principle applies to business. Lesson 1: Attention Is Highest on Day OneWhen someone joins your email list, they don’t want more emails. They want relief. They joined because they have a problem. Yet most marketers are taught to nurture first… and sell later. Kennedy flips that. When someone joins your list, that’s when you have maximum attention. Every day after that, attention drops. If your open rate is 50%, you’ve already lost half your audience’s focus. So why wait to sell? Three to five percent of new subscribers are ready to buy now. But most entrepreneurs ignore them while “warming them up.” That’s like someone walking into the ER with a bleeding leg —and the surgeon saying, “Let me tell you my backstory first.” Lesson 2: Conversion Before ExpansionKennedy accidentally built the largest list in a small niche (magicians).About 8,000 people. Small market.High skepticism.No room for fluff. So he had to master conversion. That skill later allowed him to turn one offer from $27,000 into over $500,000 — simply by structuring messaging around different psychological buying triggers and extending the sales window. The insight: If you can convert, you never have a lead problem. If you spend $10K on ads and make $11K back within 30 days, you can scale confidently. But if you grow your list without a conversion engine?You burn cash. Conversion creates freedom.Growth amplifies it. Lesson 3: You See Your Offer More Than Anyone ElseThis was one of my favorite moments. Kennedy ran a survey asking subscribers why they hadn’t bought yet. The number one response? “I don’t know what it is.” After weeks of promotion. That’s not stupidity.That’s life. Your audience is juggling work, kids, stress, bills, content overload. You are the only person who sees 100% of your content. They don’t. Repetition isn’t annoying.It’s necessary. Recap1️⃣ Sell while attention is highest2️⃣ Master conversion before scaling3️⃣ Repetition builds clarity, not annoyance If this hit home, check out Kennedy’s work at emailmarketingheroes.com or search “The Email Marketing Show.” And ask yourself: Are you nurturing…or are you converting? Reflect intentionally.Build the system.Keep surviving the side hustle.

    51 min

  2. 4D AGO

    E162 - Lessons from Robin Carr: Stop Waiting to Feel Ready

    This week on Surviving the Side Hustle, I sat down with Robin Carr — speaker, mindset coach, and creator of Thrive Unapologetically — to unpack what really happens when identity collapses… and you choose to rebuild instead of retreat. If you’re a skill-built business owner navigating growth, comfort, or quiet dissatisfaction — this one’s for you. The Core ProblemSkill-built entrepreneurs don’t lack talent.They lack permission to choose themselves. You build competence.You earn income.You create stability. And then comfort creeps in. You stop pushing.You stop experimenting.You tolerate misalignment because it still “works.” Until something external shifts. A job disappears.A title vanishes.A role gets eliminated. And suddenly you’re not just losing income —you’re losing identity. That’s where Robin’s story begins. She went from promotion and six figures…to zero income in five months. Not because she failed.Because the structure collapsed. And that collapse forced a deeper question: Who am I without the title? Lesson 1: Courage Precedes ClarityRobin hit her lowest point and said,“I don’t remember the last time I smiled.” That wasn’t the end.That was the pivot. Clarity didn’t arrive first.Action did. She stopped waiting to feel ready.She started moving imperfectly. Application:What are you postponing until you feel “ready”?What small action would create feedback today? Clarity follows motion.Courage feels uncomfortable — confidence feels good.But confidence only comes after courage. Do one imperfect thing today. Lesson 2: Healing Unlocks AlignmentRobin didn’t mask pain with positivity.She integrated it. Reading The Magic by Rhonda Byrne helped her reframe adversity — not through denial, but through conscious interruption. She used the simple mental command:“Stop.” Interrupt the spiral.Choose a new thought. But here’s the deeper takeaway: Unprocessed emotion leaks into leadership.Unhealed identity caps growth.Unresolved loss limits capacity. If you’re building something bigger, internal work is non-negotiable. Application:What experience are you trying to move past instead of learn from?Sit with it. Observe it. Extract the lesson. Healing isn’t soft work.It’s foundational work. Lesson 3: Opportunity Is Created, Not GrantedRobin waited for speaking invitations. Nothing happened. So she created her own stages. In overlooked cities.For ignored audiences.Without waiting to be chosen. That’s the shift most entrepreneurs miss. They wait for validation.They wait for invitations.They wait for “their moment.” But momentum belongs to the initiators. Application:Where are you waiting to be picked?What stage could you create this week? Workshop.Zoom group.Live stream.Meetup. Don’t wait for the platform.Build it. Prime Performance ConnectionLuck favors the prepared.Missed opportunity haunts the unprepared. And alignment fuels leverage. When I transitioned from strength & conditioning into performance strategy, I had to release identity before I gained clarity. Robin’s journey mirrors that shift. Prime Performance exists for this exact season: • Rebuilding identity• Creating alignment• Moving from comfort to expansion• Growing consciously instead of reactively

    15 min

  3. FEB 17

    E161 - From Breakdown to Breakthrough: Turning Pain into Purpose with Robin Carr

    This week on Surviving the Side Hustle, I sat down with Robin Carr — award-winning motivational speaker, author, and mindset coach — whose journey from corporate security to full-time speaking and trauma-informed coaching is a masterclass in choosing growth over fear. Robin’s momentum didn’t start from confidence.It started from collapse. And what she built from that place is powerful. The Problem High Performers FaceMany skill-built professionals live in a quiet identity trap: • You follow the rules.• You chase stability.• You build competence.• You look successful on paper. But when something gets taken away — a role eliminated, income lost, status stripped — your identity collapses with it. Robin went from six figures and a promotion… to zero income in five months. And what hit hardest wasn’t the money. It was the question: “Who am I without the title?” That spiral into depression is more common than we admit.High achievers don’t fail loudly — they unravel quietly. The Solution Robin DiscoveredRobin didn’t “bounce back.”She rebuilt intentionally. Her shift started with awareness:• Catching negative self-talk• Replacing spirals with intentional thought interruption (“Stop.”)• Practicing gratitude — even for painful moments• Choosing responsibility instead of victimhood But the real breakthrough came when she stopped waiting. Instead of waiting for speaking invitations…She created her own stages. Instead of waiting for validation…She trusted her voice. Instead of memorizing speeches…She trusted intuition and energy in the room. That alignment changed everything. Momentum didn’t come from hype.It came from congruence. Here’s the catch: Mindset work alone isn’t enough. You can learn to be positive.You can learn gratitude.You can even perform confidence. But unhealed trauma will quietly sabotage growth. Robin realized she couldn’t help others deeply until she healed deeply herself.Now she’s stepping into trauma-certified coaching — not just inspiring people for an hour, but helping them rewire long-term patterns. Because positivity without healing is just a temporary bandage. Action to Become a Prime Performer – Clarity & AlignmentIf your identity is tied only to performance, titles, or income — you’re fragile. Inside Prime Performance Coaching and the Momentum Mastermind, we work on: • Separating identity from output• Rewriting internal narratives• Aligning work with who you are becoming• Building emotional resilience before scaling success If you’ve built competence but feel disconnected —Clarity is your next step. Connect with RobinWebsite: thriveunapologetically.comSocial: @TheRobinCarr She offers:• 1:1 coaching• Drop-in group coaching• Speaking engagements• Trauma-informed transformation work If you need the bridge from breakdown to empowerment — she’s building it. Final ThoughtYou don’t need permission to evolve. You don’t need to wait for someone to choose you. And you don’t have to wait until you’re “fully ready” to step forward. Robin’s story proves something simple: The moment you stop waiting…and start choosing… Momentum begins. Reflect honestly.Choose intentionally.Keep surviving the side hustle.

    38 min

  4. FEB 13

    E160 - Lessons from Jordan DePuy: Slow Wealth, Smart Systems, and Ethical Growth

    If you’re a skill-built business owner — someone with real expertise, strong work ethic, and a desire to build security without blowing your life up — this episode was built for you. Because here’s the trap most high-performers fall into: We know how to work hard.We don’t always know how to build wealth responsibly. We trade time for money.We add side hustles without systems.We chase upside without protecting the downside. And eventually, we look successful on paper… but feel stretched thin underneath. This week’s conversation with Jordan DePuy offers a different model — one rooted in patience, preparation, and principle. Who Is Jordan?Jordan is a longtime banking professional in New York’s Hudson Valley who understands risk, lending, and financial structure from the inside out. He didn’t grow up wealthy. Money was scarce. That shaped his mindset early. While working full-time in banking, he began quietly building: • An ATM business (grown from 7 machines to 80+)• Real estate investments• Multiple income streams• All while keeping family at the center No hype.No reckless risk.Just steady, ethical growth. The 3 Big Lessons1️⃣ Preparation Beats PressureJordan shared how August 2019 felt like a breakthrough month. Cash flow was strong. Confidence was high. Then March 2020 hit. COVID exposed a critical truth: Wealth isn’t built in peak months.It’s built in preparation before the peak. Ask yourself:If revenue stopped for 90 days, what breaks? Quiet wealth is built on reserves, buffers, and discipline — not momentum spending. 2️⃣ Pattern Recognition Beats OptimismAs a banker, Jordan reviews financials daily. He’s developed the ability to spot: • Real income vs paper income• Sustainable growth vs fragile growth• Signal vs noise That skill didn’t come from motivation.It came from reps and exposure. Ask yourself:Do you know your numbers cold?Are decisions data-driven or emotional? Hope isn’t a strategy.Clarity is. 3️⃣ Purpose Sustains GrowthDuring COVID, Jordan lost his mother. At the same time, the world shut down and business slowed. Life hit hard. But he didn’t build recklessly.He built purposefully. Because purpose sustains effort when motivation disappears. Ask yourself:Why am I building this?Who is this for?What kind of life am I protecting? If your “why” is clear, endurance follows. Why This Matters for Skill-Built OwnersSkill-built entrepreneurs often confuse effort with leverage. You can grind endlessly…Or you can build systems that protect you when life hits. Jordan’s approach mirrors what we teach inside Prime Performance: • Slow down• Structure smarter• Align effort with leverage• Build without burnout You’re not behind.You’re not late.You’re building something real. And when you build patiently, prepare intentionally, and lead ethically — wealth compounds far beyond money. As always:Reflect honestly.Choose intentionally.Keep surviving the side hustle.

    14 min

  5. FEB 10

    E159 - Building Wealth Quietly & Consistently with Jordan DePuy

    What if real success isn’t loud, flashy, or viral — but patient, disciplined, and built with family at the center? That’s exactly what this week’s conversation with Jordan DePuy reveals. Jordan is a longtime banking professional in the Hudson Valley who has quietly built an impressive portfolio of side businesses while maintaining a full-time career, raising a family, and staying grounded in values that too often get lost in entrepreneurship. Jordan’s story is a reminder that wealth doesn’t have to be rushed — and freedom doesn’t have to come from burning everything down. A Banker by Accident — An Entrepreneur by ObservationJordan didn’t grow up with money. In fact, he grew up hearing “we can’t afford that” more times than he can count. That experience sparked two lifelong interests: helping people and understanding money. After realizing medicine wasn’t his path, Jordan studied finance and entered banking — learning the business from the inside out. Over the years, he noticed a pattern: the people who built real wealth weren’t just earning salaries… they owned businesses. That realization planted the seed. Growing a Side Hustle the Smart WayJordan and his brother started an ATM business with just a handful of machines and a modest investment. They didn’t chase hype. They reinvested profits, built reserves, and planned for growth. Today, that business has grown to over 80 machines, alongside real estate investments and other ventures — all while Jordan continues working full-time in banking. The key wasn’t speed.It was systems, patience, and preparation. And when COVID hit, that preparation mattered. The downturn exposed gaps, reinforced the importance of reserves, and reshaped how Jordan thinks about risk — lessons he now brings into every business decision. Seeing Opportunity Through Patterns, Not HypeBecause Jordan reviews business financials daily, he’s developed an eye for opportunity most people don’t have. He looks past surface-level excitement and focuses on fundamentals: cash flow, sustainability, risk, and margin. That perspective also makes him a better advisor. Whether he’s underwriting loans, mentoring entrepreneurs, or helping a personal trainer land their first clients, Jordan approaches growth practically — not emotionally. One powerful theme throughout the episode: opportunity favors preparation. Empty machines, poor systems, or lack of planning aren’t just mistakes — they’re missed chances. Life, Loss, and Leading With EmpathyThe conversation takes a deeper turn when Jordan shares the loss of his mother during COVID. That experience reshaped his priorities and reinforced why he builds the way he does — not just for profit, but for people. It also made him a more empathetic leader and banker. Jordan understands that numbers don’t always tell the full story — and that sometimes belief, integrity, and timing matter just as much as spreadsheets. Lessons for Side Hustlers & BuildersJordan’s advice for anyone building something on the side is simple but powerful: • Know why you’re building• Plan for both failure and success• Build reserves before you need them• Learn business fundamentals early• Find mentors who’ve lived it• Don’t sacrifice integrity for speed When asked what he hopes people say about the way he built his businesses, his answer was immediate: Ethical.Integrity.

    42 min

  6. FEB 6

    E158 - Lessons from Caroline Sangal: Realizing When Success Isn't Yours to Carry

    What if the version of success you’ve been chasing your entire life was never actually yours? That’s the question at the heart of this week’s conversation with Caroline Sangel, and it’s one every driven, capable, high-performing listener needs to sit with. On paper, Caroline was the definition of success: high school valedictorian, PhD in polymer science, fellowship recipient, elite performer in both science and recruiting, and a top 2% pace-setter in a global firm. She did everything “right.” But behind the titles was a familiar pattern — relentless pressure, external validation, and the quiet belief: “I’m only worthy if I achieve.” That belief came at a cost. Caroline’s story starts early. Growing up in a household where education and advancement were the language of love, she learned quickly how to hit targets. If an A was required, she got it. If the bar moved, she moved with it. That pattern followed her into STEM, advanced chemistry, polymers, and PhD-level research. She could do the work — and did it well — but felt deeply misaligned. Still, she stayed. Because when achievement becomes identity, walking away feels like failure. She described the early warning signs as “whispers.”Ignored whispers eventually turn into wake-up calls. Despite objective success — commercializing multimillion-dollar products and rising fast — her body began keeping receipts her mind tried to ignore. Obesity. Multiple blood pressure medications. Resting heart rates over 200 BPM. A diagnosis of supraventricular tachycardia. A cardiac ablation. Then the sentence that changed everything: “You’re holding the match. Either you make serious changes, or everything burns down.” She kept pushing anyway — until her husband said the words that finally cut through: “I’m afraid we won’t have another anniversary. Not because I’ll leave — but because you’re killing yourself.” That moment forced the real question: Who am I if I’m not what I do? Caroline didn’t quit impulsively. She planned. She waited. She built skills. She intentionally put herself in uncomfortable growth situations. And when the time was right, she left. Instead of just pivoting, she studied the problem like a scientist: Why are so many people externally successful but internally unfulfilled? Why do only 20% of people reach their potential? That work became the Next Success Method — a framework rooted in data-backed assessments, mental fitness, career alignment, values, and identity clarity. The results were real: after eight weeks of mental fitness work, her blood pressure dropped 20 points — and stayed there. Caroline now works with professionals who are questioning their careers (a natural process every 7–10 years), high achievers considering pivots, and organizations trying to unlock real potential. Her message is clear — and it aligns perfectly with Surviving the Side Hustle and Prime Performance: • Achievement without alignment drains you faster• Speed without direction becomes distraction• Questioning your path isn’t failure — it’s development• You’re not broken — you’re often just misaligned When asked what kind of world we’d live in if people designed success aligned with who they are, her answer was simple: An inspired world. A healthier world. A more connected world. 🎧 Listen to the full episode🌐 Learn more at nextsuccesscareers.com🎙️ Check out Caroline’s podcast, Your Next Success

    14 min

  7. FEB 3

    E157 - Redefining Success Before It Costs You Everything with Caroline Sangal

    What if the version of success you’re chasing isn’t wrong — but it isn’t yours? In this episode of Surviving the Side Hustle, I sit down with Caroline Sangal, a former high-achieving scientist turned career coach, to unpack what happens when traditional success starts quietly draining your health, relationships, and sense of self. Caroline checked every box: valedictorian, PhD in polymer science, elite performance, industry recognition, and financial wins. On paper, she was doing everything “right.” But behind the scenes, she was burned out, disconnected, and slowly breaking down — physically, emotionally, and relationally. This conversation is a powerful reminder that achievement without alignment eventually comes at a cost. From High Achievement to Hidden BurnoutCaroline shares how her identity became deeply tied to performance — grades, titles, accolades, and external validation. Even when she succeeded, it never felt like enough. That pattern followed her from academia into industry, and later into recruiting, where she became a top performer chasing the next milestone… even as her health deteriorated. High blood pressure. Chronic stress. Emotional reactivity. A heart condition that forced a serious medical intervention. The wake-up call wasn’t just professional — it was personal. A moment with her husband made it clear: success wasn’t just exhausting her… it was risking everything she cared about most. The Danger of Borrowed Definitions of SuccessOne of the core themes of this episode is how many of us unconsciously adopt definitions of success handed to us by parents, schools, industries, or culture — without ever asking if they actually fit who we are. Caroline explains that career questioning isn’t failure — it’s development. In fact, it’s normal to reassess your direction every 7–10 years. The problem isn’t questioning… it’s ignoring the signals. Burnout doesn’t usually arrive all at once.It starts as whispers. Ignored long enough, it becomes a breakdown. Designing Success That Fuels Your LifeAfter leaving corporate recruiting, Caroline built Next Success Careers to help people stop chasing status and start building authentic success — careers that align with how they’re wired, what they value, and the life they actually want to live. Her work blends data-driven assessments, mindset training, career strategy, and mental fitness — helping people shift from externally successful but internally unfulfilled to energized, aligned, and intentional. The takeaway is simple but powerful: You don’t need to burn your life down to build something better —but you do need the courage to question what you’re building and why. Final ReflectionIf more people stopped chasing success they were handed — and started designing success aligned with who they actually are — we wouldn’t just have better careers. We’d have healthier people.Stronger families.More meaningful work. And a lot less burnout. 🎧 Listen to the full episode🌐 Learn more about Caroline’s work at nextsuccesscareers.com🎙️ Check out her podcast, Your Next Success And as always — reflect honestly, choose intentionally, and keep surviving the side hustle.

    53 min

  8. JAN 30

    E156 - Lessons from Michael Cobb: Patience Is the Ultimate Competitive Advantage

    What if the biggest advantage you could give yourself as an entrepreneur wasn’t speed — but patience? This week’s conversation with Michael K. Cobb was a powerful reminder that real success is rarely fast. In a world obsessed with overnight wins and viral moments, Mike represents the opposite: long-term vision, deep preparation, and the willingness to do work that doesn’t pay off for years — sometimes decades. With over 30 years of experience building businesses across Central and South America, Mike has turned curiosity-driven side projects into enduring enterprises in international mortgage financing, real estate development, banking, and sustainable forestry. The Problem High Performers HaveMost side hustlers and high performers fall into short-term thinking. They feel pressure to move fast, go all-in early, and chase the next hot opportunity. If results don’t show up quickly, doubt creeps in — and projects get abandoned before they ever have a chance to mature. Speed feels productive. But it often comes at the cost of mastery, patience, and compounding returns. Mike’s success didn’t come from a master plan — it came from prepared observation. In the early 1990s, while visiting Belize, he noticed something strange: beautiful condos were being built, but construction had stalled. The reason? There was no financing. U.S. banks wouldn’t finance property in Belize, and local banks wouldn’t lend to foreigners. That gap — that friction — was the opportunity. One simple question sparked a business: “Would you sell your paper at a discount?” And just like that, a mortgage company was born. Not because Mike was searching for an opportunity — but because he was ready to recognize one. Here’s what most people miss: this didn’t replace Mike’s career overnight. For years, the business stayed a side hustle. Mike continued working in the computer industry, traveling overseas periodically, learning remotely, and letting the business grow quietly in the background. This is the part most entrepreneurs rush past. Sometimes the smartest move isn’t quitting and burning the boats — it’s patient overlap. Mike is the author of How to Buy Your Home Overseas and Get It Right the First Time — originally created to help people avoid costly mistakes when purchasing property abroad. 🎁 Free for listeners📩 Email: podcast@ecidevelopment.com📝 Subject line: Mike’s Book When asked what mistake he hopes listeners avoid, Mike’s answer was immediate: hubris. Assuming you know what you don’t.Letting excitement override diligence.Believing speed matters more than preparation. The antidote is humility, curiosity, and patience. Success doesn’t need to be fast to be meaningful.Side hustles don’t need to be rushed to be real. Build slowly. Prepare deeply. Stay ready. Because luck favors the prepared — and missed opportunity haunts the unprepared. Reflect honestly. Choose intentionally. And keep surviving the side hustle.

    15 min
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4.8
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About

Welcome to "Surviving the Side Hustle," the ultimate podcast for balancing the demands of entrepreneurship with maintaining mental, physical, and emotional well-being. Hosted by Coach Rob Tracz, an expert in helping driven professionals achieve 'personal development for professional success,' this show is more than just storytelling—it's a masterclass in thriving amidst the entrepreneurial grind. Each episode features candid conversations with leaders who are rewriting the rules of entrepreneurship, sharing their unique stories, the creative solutions they're offering, and the everyday challenges they’re overcoming. Whether you’re a side hustler looking for your big break or an established entrepreneur seeking fresh perspectives, "Surviving the Side Hustle" provides valuable insights that resonate with the movers, the shakers, and everyone in between. Feeling burnt out and sidelining your own health? This podcast empowers you to overcome stagnation, build resilience, and optimize your life and business. We dive deep into your goals, identify obstacles, and share strategies to boost your energy, improve your strength, and keep the entrepreneurial grind enjoyable. Join us for inspiring stories, expert insights, and practical advice to help you look good, feel good, and do great things at every stage of your entrepreneurial journey. Let’s not just survive the side hustle—let's master it.

Information

  • Creator
    Rob Tracz
  • Years Active
    2023 - 2026
  • Episodes
    164
  • Rating
    Explicit
  • Copyright
    © 2025 Rob Tracz
  • Show Website
    Surviving the Side Hustle