Surviving the Side Hustle

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.

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.

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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.

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.

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.com
• Seven 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.

In this Friday recap episode, Rob revisits his conversation with Anthony Cutno, a marine veteran, speaker, publisher, and branding coach who built a business while navigating homelessness, health crises, and circumstances that would stop most people cold.

Rob breaks down what made Anthony's story land so hard, tracing the through-line from a late-night conversation with God and an unexpected phone call to an unplanned stage moment that started a business.

The recap connects Anthony's experience to two core principles in the prime performance process: resilience in its rawest form, and clarity about identity before anything else gets built. The common thread in Anthony's story was never his conditions. It was his character.

What we cover:

- How Anthony's business was born from a single unplanned stage moment, not a business plan

- Building Divine Warriors Dimension organically by showing up for each need that found him

- Navigating homelessness, being shot and stabbed, seizures, and brain damage while keeping the business moving

- Why Anthony's authenticity is not a branding strategy but the only way he knows how to survive

- The role of faith and self-honesty as the two things he refused to let go when everything else was stripped away

- How clarity about identity, not perfect conditions, created momentum in the prime performance process

- The distinction between the motivational poster version of resilience and the real version Anthony lives

Chapters:

00:01 Introduction and who Anthony Cutno is

00:45 Anthony did not plan to build a business

01:10 The night outside his dad's house and the call from his sergeant major

01:40 The He-Man speaking event and the stage moment that started everything

02:14 How the business grew organically through each person who found him

02:30 The reality: building while homeless, shot, stabbed, and having seizures

03:20 Anthony's secret: radical authenticity anchored in faith

04:00 Performing vs. actually being yourself everywhere you go

04:41 Resilience in the prime performance process, the real version

05:00 Clarity as the principle people miss in a story like Anthony's

05:30 Awareness before action as the through-line of the prime performance process

06:05 How to find Anthony and follow what he is building

06:45 The one thing to sit with going into the weekend

07:02 Where to hear the full conversation and how to follow the show

Links:

Anthony Cutno on Facebook: https://www.facebook.com/search/top?q=Anthony%20Cutno

Anthony Cutno on Instagram: https://www.instagram.com/anthonycutno

Anthony Cutno on TikTok: https://www.tiktok.com/@anthonycutno

Hear the full conversation with Anthony at SurvivingtheSideHustle.com, and hit follow while you're there so you never miss an episode.

In this episode, Anthony Cutnow shares his powerful story of overcoming homelessness, embracing faith, and building a multifaceted business rooted in authenticity, purpose, and community. His journey illustrates how resilience, faith, and staying true to oneself can lead to impactful success, especially for veterans and purpose-driven entrepreneurs.

• Anthony's transition from homelessness to entrepreneurship and leadership
• The role of faith and divine purpose in his journey
• Building a diversified business in coaching, publishing, and community development
• The importance of authenticity and integrity in business practices
• Lessons learned from living in different cities: New Orleans, Dallas, California
• The significance of mentorship and community support
• The whole-person approach: spiritual, mental, and physical resilience
• Challenges in structuring and scaling a purpose-driven business
• The collective vision of Divine Warrior's Dimension: impacting next-generation entrepreneurs
• How authenticity influences marketing, branding, and client relationships

00:00 - Introduction and episode overview
00:30 - Anthony’s background: from homelessness to community leader
01:40 - Key turning points and divine interventions
03:00 - The role of mentorship, especially Jose Escobar
04:30 - How the business evolved from casual research to a multifaceted enterprise
06:00 - Living in New Orleans, Dallas, and California — lessons learned
07:50 - Faith, purpose, and overcoming health challenges
09:00 - The importance of authenticity in business
10:36 - Why Anthony is motivated to serve and share his story
11:50 - The significance of spiritual purpose in his work
13:10 - Challenges in pricing and business expansion
15:43 - Balancing humility with business growth
17:41 - Impact of authenticity on marketing and personal branding
20:03 - Building community through mentorship and shared values
23:46 - The importance of structured mentorship vs. trial-and-error learning
26:34 - Connecting the various facets of his business: publishing, coaching, and community
30:42 - The vision behind Divine Warrior’s Dimension and the collective
33:09 - How to connect with Anthony and future plans
34:00 - Final message: authenticity as a core value

• Divine Warrior's Dimension - Official website (future launch)
• Anthony’s Facebook - Social media profile
• Anthony’s Instagram - Social media profile
• Anthony’s TikTok - Social media profile

This episode highlights the power of perseverance, faith, and authenticity in transforming adversity into impactful leadership. Whether you're a veteran, entrepreneur, or someone seeking purpose, Anthony’s story offers inspiration and practical insights for your own journey.

Discover actionable strategies to create a self-sustaining business, even when you're completely off the grid. In this episode, we explore leadership, systems, and how to scale without burning out, all grounded in real-world examples from entrepreneur Eric Dingler's journey.

• Why most entrepreneurs are trapped in their own jobs and how to break free
• The importance of developing your leadership capacity before building a team
• How to buy back your time through strategic hiring and what Eric calls the "101080" rule
• Transitioning from technician to leader — avoiding the bottleneck of doing all the work
• Building systems and SOPs to transfer knowledge and delegate effectively
• Practical steps for turning knowledge into systems and automating your operations
• The significance of leading yourself first to lead others effectively

01:38 - Why entrepreneurs are often imprisoned by their own business
02:06 - Building a business that operates without you — Eric Dingler’s story
03:00 - Eric’s background: Leading a mobile family life while running a digital agency

04:20 - The core framework: “Your leadership capacity is the capacity of your business”
04:48 - How personal development lifts business ceilings
05:16 - Leading yourself first—why leadership isn’t a title, but a capacity
06:13 - The importance of developing leadership skills before building a team
07:07 - Leadership as the most transferable skill across all areas of life
08:01 - Buying back your time and guarding it fiercely
08:26 - The "CEO time" concept and the 101080 rule
09:01 - How to allocate the freed-up hours for maximum leverage
09:29 - The real cost of hiring: What you gain from investing in team members
10:20 - Small hires for big impact: reinvesting time into income-generating activities
11:08 - Getting out of the technician’s seat to scale your business
11:33 - Why staying in technical work caps your growth — Eric’s experience
13:06 - Building a system, not just training people — Eric’s SOP approach
13:32 - It’s never a people problem, but a systems problem
14:02 - Transfer knowledge into systems, not just people
14:36 - SOPs as the backbone of scalable, autonomous operations
15:02 - Documenting repeatable tasks to empower delegation
16:24 - Connect with Eric at ericdingler.com for resources and coaching
16:48 - Download resources: First hire checklist and diagnostics call
17:15 - Final wisdom: Lead yourself first, then lead others — unlock your full potential
17:55 - Take action today: Grow your leadership capacity to scale and live better

• Eric Dingler’s Website
• First Hire Readiness Checklist
• Free 25-Minute Diagnostics Call
• Example SOPs: How to Make Eric a Cup of Coffee, How to Create SOPs

In this episode, Eric Dingler shares his inspiring journey from running a summer camp and local church ministry to building a successful online marketing agency while traveling the world. He emphasizes the importance of leadership, systems, and intentional hiring for scaling a business without burnout.

• How Eric turned his web design skills into a fundraiser for international adoption and built a nonprofit.
• The evolution from side hustle to full-time business, highlighting key moments and mindset shifts.
• Strategies for creating scalable systems in your business: leadership, lead generation, lead conversion, project management, and money management.
• How to build effective remote teams using SOPs, gap hiring, and systems thinking.
• Practical advice on delegation mindset, including transferring knowledge into systems and SOPs to free up your time.
• The importance of leadership development for entrepreneurs and their teams.
• Future goals: scaling his coaching business and building a team to support remote entrepreneurs.

00:00 - Introduction to Eric Dingler's journey from summer camp to global entrepreneur

01:26 - Origin story of Eric’s web design agency as a fundraiser for adoption

02:34 - Building a nonprofit organization to fund international adoption

03:52 - Transition to traveling with family and how systems enable remote lifestyle

05:20 - Developing core business systems for scalability

09:07 - Leadership as the foundation of business systems

11:53 - The five core systems: leadership, lead gen, conversion, cash flow, project management

12:19 - Managing multiple systems simultaneously

13:41 - How Eric defines true leadership

15:29 - From side hustle to a full-time coaching business

16:25 - Transition from working in the business to working on the business

17:38 - Managing family life while traveling and working remotely

19:47 - The importance of hiring and systems in scaling

22:09 - Creating shared success through team building and hiring

23:37 - How to approach hiring for the right fit and culture

24:39 - Differentiating gap hires and team hires

26:22 - The importance of taking up to 80% of new hires' time to maximize productivity

28:48 - The cost of not hiring and focusing on revenue-generating activities

30:57 - Overcoming mindset hurdles around delegation

31:24 - Systems approach to delegation and SOPs

33:20 - Documenting systems with SOPs and creating a culture of continuous improvement

35:31 - Eric’s future goals: coaching full-time and building a larger impact

36:36 - Launching programs and scaling coaching services

38:28 - How to connect with Eric and take the first step in hiring

40:46 - Practical tools: first hire readiness checklist and diagnostics calls

42:31 - Final advice for entrepreneurs feeling stuck: lead yourself first

• Eric Dingler’s Website
• First Hire Readiness Guide
• First Hire Readiness Checklist

In this episode, Rob Tracz chats with Cindy Van Eckhout about redefining success beyond financial metrics. They explore how high achievers can feel empty despite outward success, and how to build a life aligned with inner joy and purpose.

• The distinction between being rich (money) and wealthy (fulfillment) and why it matters
• Recognizing the signals of misalignment before burnout using body awareness and mindfulness
• The importance of listening to your inner "feeling" and how nature can reconnect you with your truth
• Adopting a growth mindset: "You either win or you learn," especially during challenges
• Joy as a way of being, not a goal to achieve at the end of the journey
• The four joy blockers: misalignment, overload, emotional suppression, and physical depletion
• Building an aligned, sustainable path where happiness is part of the process—not the reward
• Practical advice: Start small, ask what brings you joy, and take consistent steps toward it

00:00 - Introduction: Rethinking success beyond appearances
02:19 - Would you have the courage to shut down a thriving business?
03:00 - The trap of being rich on paper but poor inside
03:56 - Cindy's bold move to France and building authentic success
04:53 - Difference between being rich and truly wealthy
05:16 - Personal reflection: chasing societal success vs authentic fulfillment
06:11 - Listening to the body's signals of misalignment
07:00 - How nature and silence help reconnect with inner guidance
08:12 - Your internal state as a dashboard for life alignment
09:01 - The growth mindset: challenges are lessons, not losses
09:48 - Embracing difficulty as a catalyst for growth
10:41 - Challenges as opportunities for learning, not failure
11:11 - Resilience as a foundation for sustainable growth
12:33 - Joy is the journey, not the destination
13:32 - The four joy blockers and how to identify them
14:30 - Misalignment is common, but fixable
15:00 - The fallacy of suffering now and happiness later
15:59 - Joy is created on the way up, not at the top
16:50 - The risks of building success based on others’ definitions
17:19 - Connect with Cindy and her resources
18:47 - Small steps toward joy and success, inspired by Denzel Washington

• Website: allegracoaching.eu
• LinkedIn: Cindy Van Eckhout