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. 13h ago

    E206 - Lessons from Joe Wyrwas: Tracking Means Nothing Without Change

    Four years of logging every minute of his life taught Joe Wyrwas one uncomfortable truth: the gap between the life you say you want and the life you are actually living is visible in the data, if you are willing to look. Rob recaps his conversation with leadership development coach Joe Wyrwas, tracing Joe's path from a quiet kid cracked open by a 10-day summer program to 15 years of unpaid volunteer work to finally launching his own LLC. The through-line is clarity, specifically the discipline of seeing yourself honestly before trying to lead anyone else. Rob connects Joe's four-year time audit and his skydiving approach to risk straight to the clarity principle inside the Prime Performance Process. What we cover: - Joe's origin story: a 10-day Archdiocese of Baltimore leadership camp the summer after sophomore year of high school that rewired how he saw himself - Fifteen-plus years of unpaid volunteer work in youth leadership before launching his LLC, and why he carries no regret about the timeline - The four-year daily time-tracking spreadsheet and what the data actually reveals about misalignment between stated priorities and real behavior - Joe's framework for overwhelm: write your why, write your list, connect the dots, and cut what does not serve the why - The skydiving analogy: instead of managing every second of the jump, identify the three moments where things can go wrong and focus attention there - Joe's honest stance on who he will and will not work with: if someone is not willing to grow, he is not the right fit - Rob's distinction between collecting data and using data: information without honest reflection is just noise - How the clarity principle from the six-principle Prime Performance Process applies: knowing your goal is not enough if you cannot see what is quietly pulling you away from it Chapters: 00:00 Opening: picturing the four-year time audit 00:42 Who Joe Wyrwas is and why his approach is different 01:18 Joe's origin: quiet kid, 10-day leadership camp, something cracked open 01:54 Fifteen years growing the seed through college, tech, and volunteer work 02:30 Launching the LLC and standing on the body of work 03:00 The psychological weight of giving your best energy to a side thing 03:45 What the time-tracking data really shows you 04:15 Joe's advice for the overwhelmed: write the why, connect the dots, cut what does not fit 04:40 The skydiving framework: find the critical failure points and focus there 05:10 How this maps to clarity in the Prime Performance Process 05:57 Data without honest reflection is just noise 06:30 Where to find Joe: LinkedIn and wiserwithjoe.com 07:53 Rob's closing challenge: pick one thing, connect it to your why, make a decision Connect with our guest: Joe Wyrwas on LinkedIn: https://www.linkedin.com/in/joewyrwas Wiser with Joe: https://wiserwithjoe.com More from Rob: Rob Tracz: https://robtracz.com Free momentum assessment: https://gettheprime.com Free strategy session: https://survivingthesidehustle.com/freecall

  2. 3d ago

    E205 - Tracking Every Minute and What It Taught About Leadership with Joe Wyrwas

    Joe Wyrwas spent four years building a custom app to log his life down to the minute, and what he learned had almost nothing to do with the data. Joe Wyrwas, leadership development coach and 600-plus-jump skydiver, walks Rob through the framework he uses to help individuals and organizations build stronger cultures, starting with self-awareness and ending with purposeful action. The conversation covers how leaders can communicate through uncertainty, why tracking data without making changes is just noise, and how skydiving taught Joe to find the three key failure points in any plan. Rob and Joe also get into the emotional side of leadership, including how naming a feeling out loud is often the first step to moving through it. What we cover: - How a 10-day faith-based leadership program in high school set Joe on a lifelong path of developing others - The three-part foundation Joe uses with every client: know yourself, communicate with others, anchor to your purpose - Why uncertainty, especially around AI, is the single biggest challenge he sees leaders facing right now - The four-year experiment of tracking his life to the minute and the three hard lessons it revealed - Why most people already know their misalignments and do not need more data to confirm them - How leaders can balance transparency with stability when communicating difficult news to their teams - Daily practices Joe uses to move from uncertainty and doubt into grounded, purposeful action Chapters: 00:01 Welcome and guest intro 01:04 Where Joe's leadership journey began: the 10-day high school program 02:31 Learning through real failure as a team of high schoolers 03:36 Joe's coaching framework: self, others, and purpose 06:33 Handling clients who think they already have it figured out 08:34 The power of listening to the words people choose 09:25 From nonprofit volunteer work to launching an LLC 12:12 Who Joe works with now: nonprofits and tech companies 14:20 The number one challenge leaders face right now: uncertainty 17:01 Joe's daily practice for processing doubt and fear 20:20 The four-year experiment tracking every minute of his life 22:46 Three lessons the data revealed, and why he finally stopped 24:52 Are leaders tracking too much or not enough? 27:49 Decision-making, risk tolerance, and the 70 percent rule 29:21 600-plus skydives and what they teach about calculated risk 31:10 The three key failure points: how to reduce risk without controlling everything 32:10 What Joe is building in 2026 If this conversation got you thinking about how you lead, follow Surviving the Side Hustle so you never miss an episode. Find us and every guest resource at SurvivingtheSideHustle.com. Connect with Joe: LinkedIn WyserWithJoe.com More from Rob: Website: https://robtracz.com Free momentum assessment: https://gettheprime.com Free strategy session: https://survivingthesidehustle.com/freecall

  3. Jul 17

    E204 - Lessons from Holly Porter: When a Near Death Experience Rewrites Everything

    You don't have to almost die to truly live. Holly Porter said it in her guest interview, and Rob hasn't stopped thinking about it since. Rob breaks down the biggest lessons from his conversation with Holly Porter, a 15-time international best-selling author who spent 70 days on a ventilator in 2021 and came out the other side with two new companies, a finished book, and a clarity she says most people never find. He walks through the unglamorous stretch that followed, two years of long COVID fog, a shelved manuscript, and a missed opportunity with a billionaire-backed company, before landing on the single question that kept Holly moving forward. Rob then connects her daily practice to the Prime Performance Process, making the case that clarity starts with an honest internal check-in, not a five-year plan. What we cover: - Holly's 70-day hospitalization, her near-death experience, and what she describes as the Stadium of Light - The slow, unglamorous recovery: going from 20 percent function to 70, and the two years she called hell - The book Near Death Shift, the year it sat untouched, and why she eventually took it back - The better is better motto and how a single morning question replaced the need for a big strategy - Gratitude as an active discipline, not a feeling to wait for, and serving others as an energy reset - Why Holly walked away from a deal backed by a billionaire based on what she was told in her near-death experience - Rob connecting Holly's daily self-check to the clarity principle inside the Prime Performance Process - Holly's Linktree, her nonprofit the Adventure Bucket Wish Foundation, and the International Retreat Association she is building Chapters: 00:01 Opening quote and introducing Holly 00:50 Who Holly is: author, founder, nonprofit builder 01:45 The 70-day hospitalization and the Stadium of Light 02:24 What happened after the hospital: new companies and the book 02:55 The honest low points: long COVID, fog, and two years of hell 04:14 The better is better motto 04:49 Gratitude as practice and serving others to shift energy 05:30 Connecting Holly's approach to the Prime Performance Process 06:20 Clarity as the core principle: internal calibration before action 07:10 Where to find Holly and her book Near Death Shift 07:55 Closing reflection and the one question to sit with Links: Holly Porter Linktree (book, website, social, retreat association, nonprofit): https://linktr.ee/hollyporter Hear the full conversation with Holly on episode 203, and catch every guest interview and Friday recap at SurvivingtheSideHustle.com. If you are not following the show yet, now is a good time.

  4. Jul 14

    E203 - Building an Industry From Scratch After a Near Death Shift with Holly Porter

    In this episode, Holly Porter returns for part two of her conversation with Rob. A 15-time best-selling author and founder of more than a dozen businesses, Holly shares what has happened since her near death experience and how that experience continues to shape every decision she makes. Holly walks through the writing of her book Near Death Shift, from a working title she sat on for two years to the moment the chapters clicked into place. She then explains how, mid-manuscript, she received the idea for the International Retreat Association, an organization she is now building from nothing in an industry that has never had one. The conversation covers imposter syndrome, the habit of comparing yourself to who you were yesterday, and why gratitude starts to change what you notice. What we cover: - How a COVID hospitalization of 70 days produced out of body and near death experiences that redirected her business decisions - Why she walked away from a billionaire-backed partnership based on what she was told during the near death experience - The stop-and-start process of writing Near Death Shift, including handing the project off and then taking it back - How the acronym SHIFT emerged after the title change and how it connected to a personal development program she had built five years earlier - The gap she found in the retreat industry: an estimated two to three million retreat leaders with no association to belong to - How she incorporated the International Retreat Association in December, set founding member pricing at 111 dollars per year, and filled half the leadership council before the landing page was even live - Why she told her attorney they did not need everything figured out before launch, drawing a parallel to how Apple and PayPal update their terms over time - The difference between imposter syndrome before her experience and the absence of it now with the association - Her recovery motto, better is better, and how asking what you can do today to be better than yesterday applies beyond health Chapters: 00:01 Welcome back and guest introduction 01:31 Holly reacts to the intro 02:20 The near death experience and what changed 04:45 Two years of illness after the hospital and finding resilience 05:32 Why she listened to the calling over the billionaire deal 07:25 The gift of all knowing in the stadium of light 08:02 How the idea for Near Death Shift arrived 10:06 Taking the manuscript back and finishing it 11:58 Finding the title and the SHIFT acronym 13:54 Connecting the book to a five-year-old program 14:20 The idea for the International Retreat Association arrives 16:36 Building an industry structure from a blank canvas 18:29 Professional standards, values, and the founding member model 19:25 Why she told her attorney they do not need all the answers first 20:35 Pricing at 111 dollars and the 11-11 connection 21:17 Imposter syndrome before versus the absence of it now 22:12 Questions she asked herself while dying in the hospital 23:18 Comparing yourself to who you were yesterday 25:46 Attracting negativity versus noticing the good, and the better is better motto Links: Holly Porter link tree (book, website, social, email): https://linktr.ee If something in this episode moved you, share it with someone who needs to hear it. Follow Surviving the Side Hustle and find every episode at SurvivingtheSideHustle.com.

  5. Jul 10

    E202 - Lessons from Adam Torres: Starting Before You Are Ready and Shipping Ugly

    In this Friday recap episode, Rob revisits his conversation with Adam Torres, founder of Mission Matters and host of nearly 7,000 interviews, to pull out the lessons that matter most. Adam went from managing over 200 million dollars in finance to building one of the most prolific media companies in podcasting, and he did almost none of it on purpose. Rob breaks down how Adam Torres built Mission Matters through a series of reluctant starts, hidden identities, and unpolished outputs, including a self-published book handed out like a business card and a podcast recorded as unedited phone calls. The recap connects Adam's story to three core principles Rob returns to repeatedly: clarity, resilience, and opportunity. The central takeaway is that the gap between knowing and doing is where most people get stuck, and Adam's career is a case study in refusing to live there. What we cover: - Adam spent nearly 14 years in finance managing over 200 million dollars before any of his media work began - A mentor pushed him to write a book he did not want to write, which he called his ugly duckling and handed out like a business card - That imperfect, self-published book led to speaking tours in China and real business from cold LinkedIn connections - His first podcast was unedited phone recordings uploaded directly from his phone, no production, no polish - He hid behind an early show called The Gratitude Show and shut it down when the audience growth scared him - Adam's pattern of acting before conditions are perfect is strategic underneath, not reckless - He compares today's podcasting landscape to YouTube when it had roughly one million channels, arguing the opportunity is early and the data says move now - Rob maps Adam's story onto three prime performance principles: clarity, resilience, and opportunity - The episode closes on one idea: your version one does not have to be good, it has to exist Chapters: 00:00 Introduction and who Adam Torres is 02:24 First 300 episodes as unedited phone recordings 02:44 Fighting his own resistance at every stage 03:10 The Gratitude Show, hiding, and shutting it down 03:40 Shameless rough audio and deflecting feedback 04:10 Starting before ready as a trained habit 04:43 The podcasting opportunity compared to early YouTube 05:10 Clarity as the first prime performance principle 05:40 Resilience as the second prime performance principle 06:00 Opportunity as the third prime performance principle 06:20 Awareness before action creates momentum 06:35 Where to get Adam's book and follow his work 07:11 Closing thought: version one has to exist, not be good Links: One Billion Podcasts (free book): https://1billionpodcasts.com Adam Torres on Instagram: https://www.instagram.com/askadamtorres Hear the full conversation with Adam Torres at SurvivingtheSideHustle.com. If the show is adding value to your journey, follow us so you never miss another episode.

  6. Jul 7

    E201 - How Podcasting Became a Media Business Built Like a Factory with Adam Torres

    In this episode, Adam Torres shares how a career in finance, a reluctant first book, and a co-founder who wouldn't take no for an answer led him to accidentally build one of the largest podcasting operations in the world. He has conducted nearly 7,000 interviews, launched over 250 shows, and written a book on why podcasting is still in its early stages. Adam walks through the unlikely path from financial advisor to media company founder, including why he ignored every good idea until he couldn't anymore. The conversation covers how he built the production infrastructure before he ever focused on becoming a better host, and why he believes the host's genuine engagement matters far more than format, gear, or trends. He also gets into the systems thinking that allowed him to scale to over 1,500 interviews a year without losing his mind. What we cover: - How handing out a self-published book as a business card led to speaking tours and eventually a media company - The early Periscope streaming show called the Gratitude Show, and why growing an audience scared him into stopping - Why his first 300 podcast episodes were unedited phone call recordings and still built an audience - Building the production side like a factory, tracking cost per episode down to the quarter, before ever focusing on being a better host - How systems and obligations to guests, rather than personal discipline, are what keep him showing up consistently - The difference between quantity-first and quality-guest podcast strategies, and how to choose the right model - Why format, AI tools, and production trends matter far less than whether the host genuinely enjoys what they are doing - Reading nearly 10,000 pages of entertainment biographies to study the patterns behind great hosts - What his book One Billion Podcasts argues about where podcasting is headed and why the window is still open Chapters: 00:00 Introducing Adam Torres 01:20 Starting in finance at 16 and managing $200 million 02:30 Writing a book he did not want to write 03:49 Handing out the book as a business card and landing speaking tours in China 04:26 The shift toward publishing and the anthology book model 06:49 Publishing Barry Sanders and building a full book company 07:03 How the co-founder pushed him into podcasting against his will 07:33 First 300 episodes: unedited phone call recordings 09:03 The Gratitude Show on Periscope and the moment that scared him 11:47 What kept him going through the early episodes 12:26 Systems over discipline: designing a company around the host 15:56 Building the production factory with a finance mindset 17:20 Posting episodes within two hours of recording 18:46 Spending 95 percent of early time on production, 5 percent on hosting 20:03 Reading 10,000 pages of entertainment biographies to study great hosts 22:05 Interviewing anyone with a pulse: the quantity-first strategy 23:11 What actually matters in podcasting, regardless of trends 24:07 Why the host's genuine engagement is the only thing that never changes 25:27 Choosing audio only for the right audience and niche Links: One Billion Podcasts book and website: https://onebillionpodcasts.com If this episode got you thinking about your own story and how to use it, follow Surviving the Side Hustle and catch every new episode at SurvivingtheSideHustle.com.

  7. Jul 3

    E200 - Lessons from Ohan Kayikchyan: Stop Waiting for Someday to Live Your Life

    In this solo recap, Rob revisits his conversation with Ohan Kayikchyan, Ph.D., founder of Alohana Financial and returning guest on the show. Rob unpacks the lessons that hit hardest, including a personal story about his father that shapes everything he believes about time, money, and what it means to actually live. The episode centers on a deceptively simple idea: money is a tool, not a destination. Rob walks through the psychology behind financial behavior, the trap of lifestyle creep, and why high earners so often stay stuck. He also shares a deeply personal loss that turned the abstract danger of deferring life into something concrete and urgent. What we cover: - Why Ohan argues financial planning is 80% behavior and psychology and only 20% math, and what that ratio means for entrepreneurs - The want versus need distinction: how confusing the two drives financial stress and blurs business decision-making - Lifestyle creep and the Henry trap: why earning more without widening the gap between income and spending changes nothing - How Ohan shifted from handing clients answers to listening without judgment, and why the insight people discover themselves is far more powerful than advice - The honeymoon effect in retirement and why waiting until 67 to live your dream life carries real physical and logistical costs - Mini-retirements as an intentional, planned alternative to the grind-now, live-later model - Rob's story of his father, who died before collecting his first retirement check after a lifetime of building toward someday - The midlife awakening reframe: choosing to live on purpose now rather than waiting for a crisis to force the shift Links: Alohana Financial: https://www.alohanafinancial.com If this episode made you think twice about what you are waiting for, follow Surviving the Side Hustle so you never miss a conversation. Find every episode and more at SurvivingtheSideHustle.com.

  8. Jun 30

    E199 - Why Financial Planning Should Help You Live Now with Ohan Kayikchyan

    In this episode, Ohan Kayikchyan returns to share how nearly two decades in finance taught him that the numbers are only 20 percent of the work. The other 80 percent is behavior, belief, and knowing what you actually want from life. Ohan walks through the shift in his practice from pure financial optimization to life planning, explaining why listening to clients matters more than presenting solutions. The conversation covers his EVOKE process, the psychology behind wants versus needs, and the case for experiencing life before retirement rather than after. Rob also shares a personal story about his father that puts the cost of waiting in sharp relief. What we cover: - How Ohan immigrated through the Diversity Visa Lottery and built a financial career from bank teller upward - Why he says AI will soon handle the optimization side of finance, and what that leaves for human advisors - The distinction between wants and needs, and why even native English speakers confuse the two when managing money - His EVOKE process: Exploration, Vision, Obstacles, Knowledge, and Execution across five client meetings - Why the first three meetings with clients involve no numbers at all, and what that reveals - The concept of mini-retirements and sabbaticals as an alternative to waiting until 67 - The honeymoon effect in retirement and why deferred living often leads to regret - Who benefits most from life planning: immigrants, and high earners who are not rich yet (HENRYs) - The difference between YOLO spending and intentional early enjoyment backed by a real financial plan Chapters: 00:01 Welcome back and Ohan's background 01:49 Growing up in a post-Soviet country and learning English 04:05 Starting as a bank teller and breaking through the language barrier 06:22 Realizing financial planning is 80 percent psychology 07:57 From CFP to registered life planner, and the book that changed everything 10:47 Listening without judgment and creating a guilt-free space for clients 13:45 The EVOKE process explained 15:36 Tackling obstacles and when money is not actually the problem 17:51 Why the first meetings have no numbers 18:25 The honeymoon effect and the cost of waiting until retirement 20:25 Mini-retirements and the case for living sooner 22:46 Rob's story about his father and the real risk of deferring life 24:09 Inheritance, permission, and enjoying money while alive 26:58 How society embeds the nine-to-five mindset and how to challenge it 28:28 Who Ohan works with: immigrants and HENRYs 30:27 Lifestyle creep, student loans, and the HENRY trap Links: Alohana Financial: https://www.alohanafinancial.comSeven Stages of Money Maturity by George Kinder: https://www.georgekinderbooks.com If this conversation made you think differently about money and time, share it with someone who needs to hear it. Follow Surviving the Side Hustle and find every episode at SurvivingtheSideHustle.com.

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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
    207
  • Rating
    Clean
  • Copyright
    © 2025 Rob Tracz
  • Show Website
    Surviving the Side Hustle