The Solo 2 Entrepreneur Show
by Lorraine Chai
Solo 2 Entrepreneur is the ultimate podcast for solopreneurs and small business owners seeking to thrive in business. Hosted by Lorraine Chai, a business strategist, each episode features interviews, discussions, and actionable strategies from industry experts. From mastering leadership to navigating digital marketing, ”Strategic Success” provides the tools and knowledge needed for entrepreneurial excellence. Tune in to unlock your full potential and build a thriving business.If you would like to know more about Lorraine, what she does, or want to work with her, check out her web link atwww.solopreneur2entrepreneur.com/linkRemember to follow, share, and leave a review. We would love to hear from you.
Episodes
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#118 You Don't Have to Be Elon Musk to Be an Entrepreneur (Mark Agusti)
What does it actually take to build a career that means something? Mark Agusti - Duke alumnus, former healthcare executive, and founder of Kenmore Advisors - almost became a doctor, turned down higher-paying offers at Intel and Microsoft, and built an executive career across medical technology...
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#115 Your Business Is Growing. So Why Aren't You Getting Richer? (Ernest Smith)
What happens when you're working harder than ever, growing your business, and still realizing that the business model isn't working for you? In this episode of The Solo 2 Entrepreneur Show, I sit down with Ernest Smith to unpack his journey from real estate investing and construction to thinking...
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#114 I got Fired
Most people get fired and spend months asking "what did I do wrong?" In this episode, we pull back the curtain on something most entrepreneurs and leaders are too proud to talk about - being let go, pushed out, and shown the door. More than once. But here's what nobody tells you: the pattern…
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#113 Survival Mode Is Not a Strategy - Here's What Is
You said you wanted it. The business. The life. The version of yourself that stops waiting and starts building. So why haven't you moved? We cover the one thing that kills more dreams than failure, bad timing, or lack of money ever will - and that thing is fear dressed up as logic. Circumstances...
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#112 The Real Game Reveal "The Deal Was Never the Deal" (John Matthews)
John Matthews walked away from the C-suite - 1,400 stores, a $3B company, Jimmy John's - and built something most entrepreneurs never do: a business that has generated revenue every single month for over two decades. His secret? He never waits until he needs something to build a relationship. In...
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#111 Why the Quietest Person in the Room Is Usually Winning
What if the thing you were told was your weakness is actually your greatest business asset? Strategic silence - what is it and how do you use it? From being labelled the quiet, introverted kid to sitting across from billionaire entrepreneurs and high-level coaches, Lorraine noticed one thing they...
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#110 Nobody Warned Me About This: The Hidden Cost of Business
Starting over is hard. Whether you're new to an industry, a business, a city, or a country - the feeling is universal: the self-doubt, the broken trust, the loneliness that nobody warned you about. In this episode, Lorraine Chai gets honest about what it really feels like to be the new kid in the...
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#109 From $25 Million to $400: The NFL Star Who Lost It All and Built It Back (Marques Ogden)
What happens when you build a $25 million empire-and then watch it collapse in under nine days? In this episode of the Solo to Entrepreneur Show, host Lorraine Chai sits down with Marques Ogden, retired NFL player turned transformational speaker, to unpack one of the most brutally honest…
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#108 Living my Plan C until I got slapped
Something happened to me that forced a real decision: keep living small, or finally choose my Plan A. In this episode, I tell a simple, honest story about a hard month during COVID that changed how I see fear, time, and self-worth. This is not a “perfect success” story. It’s about what you do…
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#106 You’re Not Shy. You’re Strategic: The Ambivert Advantage in Business
Think you’re an introvert but people call you an extrovert? You might be an ambivert. In this episode of the Solo 2 Entrepreneur Show with Lorraine Chai, I share what that really means, why it matters in business, and how to use your balance of confidence and quiet to build trust, lead better…
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#105 They Judged Me in Seconds: Turn It Into Power
In this episode of the Solo 2 Entrepreneur Show, Lorraine Chai shares how being misunderstood and judged became her advantage. She breaks down the “watcher” mindset: how to stay calm, read people, set boundaries, and use criticism as fuel. If you’ve ever been labeled “difficult” or…
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#104 The Shift Nobody Talks About: How Diego Munoz Went From “Starting Over” to Owning the Room in Business
What does it really take to go from “I’m figuring it out” to I’m building something that outlives me? In this interview, Diego Munoz breaks down his transition from relocating and starting fresh to becoming a business owner focused on building stability and opportunity for his family. But this...
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#103 Comfort Zones Are a Myth
You’ve heard “get out of your comfort zone” a thousand times. But most people misunderstand it and that’s why they stay stuck. In this episode of The Solo 2 Entrepreneur Show, Lorraine reframes comfort as something you build and upgrade, not something you “escape.” You’ll learn how high…
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#102 A Father's lesson to his daughter
Here's a relationship that isn’t picture-perfect. I’m not close with my dad, but I’m still his daughter and I’ve learnt powerful lessons from who he is and what he’s lived through: growing up as the oldest son of nine kids on a chicken farm, becoming a medical doctor, building a clinic, and...
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#100 Buggy Landlord, No Pause Button
I walk you through how I handled a real-life disruption that could have derailed my business - and the exact decision-making framework I used to stay calm, protect my environment, and keep executing anyway. What you’ll learn in this recording: How to switch from panic to fast, clean decisions…
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#99 Rethinking the Business Exit - The First Rest Stop, Not the Finish Line with Adam Coffey
Private equity legend Adam Coffey joins Lorraine Chai to break down how he went from Army discipline to CEO exits, completing 58 acquisitions and helping drive $2.5B in exits. You will learn why the best operators buy great companies (not fixer-uppers), how multiple liquidity events can beat the...
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#98 The Quietest Crowd I’ve Ever Heard
I didn’t grow up with Memorial Day, so I walked into my first one with one goal: learn. In this episode, I share what it felt like attending Flags for Heroes hosted by Rotary in Clayton: the presence of police, fire, military, residents, Rotarians, and families of all ages moving together to…
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#97 “I Don’t Know” Was My Comfort Zone
I used to hide behind the phrase “I don’t know” because being wrong felt unsafe. In this episode of The Solo 2 Entrepreneur Show, I share how my upbringing in a strict entrepreneurial family shaped that fear, what I learned from my vocal teacher Kerrie Biddell about focusing on progress, and how...
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#96 Stop Selling “What You Do”: Sell the “Why” With Story
Most marketing fails because it skips the part buyers actually need: the story behind the offer. Paige Stapleton and Brian Stark join Lorraine to unpack why storytelling is not fluff. It is the bridge between emotion (why people buy) and logic (how they justify it). They also share what it is...
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#95 The 3AM Decision: How the Right Room Changes Your Life
I met a young entrepreneur in Cambodia showing up at 3AM on the same coaching call. What level of commitment really means, why the right mentors and rooms can accelerate your growth, and how to move even when you feel scared, behind, or “not ready.” If you’ve been protecting comfort instead of...
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#94 Investing in Yourself Until Your Last Breath
Growth is not a season. It’s a lifestyle. Let's unpack why every human is wired for development and why the best investment is the one where you bet on yourself on purpose. This episode ties self-investment to legacy: the desire to evolve, build, give back, and bring others along for the journey,...
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#93 The Gold Shoes Mayor: Growth, Business Density, and Community Trust
What does it take to lead when the room is loud and the stakes are public? Lorraine Chai talks with Jacques Gilbert, Mayor of Apex, on leadership, identity, and building community. From a historic Black neighborhood to 29 years in law enforcement (retired Captain) to Mayor, he shares mindset...
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#92 Become the Fearless Leader
In this episode, discover the truth behind fearlessness in entrepreneurship - it’s not about absence of fear, but mastering it to make confident decisions amid uncertainty. Whether you’re facing business upheaval or life’s unexpected twists, learn how to reclaim control, prioritize with clarity,...
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#91 Mastering Chaos: The Entrepreneur’s Guide to Staying Calm and Winning
When everything feels like it’s falling apart, how do top entrepreneurs stay calm, focused, and in control? In this episode, Lorraine Chai shares real stories and proven strategies to help you move from reactive chaos to proactive leadership. Discover how small mindset shifts and daily habits can...
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#90 Be the Shepherd and not the sheep
In this episode, Lorraine gets personal about a turning point every entrepreneur must face: deciding to stop outsourcing your leadership and start owning your business decisions. She shares how she recognized her “sheep behavior” - constantly waiting on others’ opinions and market noise - and…
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#89 From PhD Dropout to Real Estate Innovator: The Power of Pivoting and Perseverance
Garret Wong shares his unconventional journey from nearly completing a PhD in molecular biology to building a thriving real estate empire with over 75 rental properties. Facing cultural expectations, parental pressure, and the fear of failure, Garret reveals how he broke free from traditional…
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#88 Grieve but bounce back strong
Loss is inevitable. Leadership is a choice. In this episode, Lorraine shares a personal reflection on loss — and why moving forward with clarity, discipline, and purpose is what defines true entrepreneurial leadership. If you’ve ever had to build while grieving, this conversation is for you.
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#87 What Filmmaking Teaches Us About Business Grit
In this episode, I have with me actor, director, and producer Michael Manasseri to explore the highs and lows of his multifaceted film career. Michael shares candid insights on transitioning from acting to producing, drawing striking parallels between filmmaking and entrepreneurship. From...
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#86 Your Comfort Zone Is the Most Dangerous Place for a Business Owners
In today’s episode, we tackle a subtle but critical risk for any business owner: the comfort zone. It doesn’t feel like danger, but staying comfortable in your business can silently stall growth, dull leadership, and leave you vulnerable to disruption. I share insights from a recent talk with a...
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#85 From Dishwashing to Multi-business Empire
In this episode, Zsolt shares how he Scaled 40+ Companies Across 14 Sectors - uncover the real journey behind building and scaling multiple successful businesses globally. Starting from washing dishes and working his way up in hospitality, Zsolt shares the grit, failures, and relentless focus…
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#84 Don’t Build a Business That Shuts Down at the First Sign of Disruption
In this episode, Lorraine draws a powerful parallel between a recent state-wide lockdown triggered by just a light dusting of snow and how businesses react to disruption. While some places weather feet of snow and keep moving, others pause at the slightest challenge - and so do many businesses…
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#83 No Excuses, No Limits: Commit to a New Standard
Let's level up.
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#82 Branding Beyond Logos: Unlock Your Personal Power Through Color
Today’s episode goes beyond traditional branding - it’s about the power of color and personal presentation in building your authentic brand and presence. Lorraine sits down with Gretchen, a color expert and founder of Color Me Beautiful, to reveal how the right colors can: Make you look…
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#81 A Strong New Year means so much more
Happy New Year 2026. As we review our previous years, this year is the year to double down and moving forward and upward. Listen to this episode to hear what else will be in place for the rest of the year...
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#80 AI: Fear, Future, and Opportunity - A Deep Dive with Damon Davis
Is AI really a threat to jobs or just the next evolution in technology? How has AI quietly been part of our lives for decades? What should entrepreneurs and business owners know to embrace AI for growth instead of fear? In this episode, Damon shares expert insights on the practical applications…
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#79 Merry Christmas and thank you
Merry Christmas and thank you for all the love. You all are amazing for being a part of this journey with me. I'm looking forward to more....
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#78 Give More Builds Reputation and Unlock Long-Term Success
Join Lorraine Chai on The Solo Entrepreneur Show as she sits down with Gates, a Canadian general contractor who has successfully expanded his luxury home development business across the US. In this episode, Gates shares his entrepreneurial journey, from starting door-to-door sales at age 18 to...
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#77 From Kindness to Credibility
No matter how poorly people can treat you, here is the secret to being a better person.
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#76 The Grinch journey into Elite Circles
What is the goal that you have for yourself? How do we become and be in those elite networks or groups of people?
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#75 IT to Sahara Adventures: Building a Global Experience Brand with Sven Sperling
Today's episode is with Sven Sperling, a German adventurist entrepreneur who turned his childhood passion for off-roading into a thriving international business. Discover how Sven transitioned from IT and software training to creating once-in-a-lifetime, 4-wheel drive experiences across deserts…
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#73 Growth through Feedback
All feedback is good for growth. It may not be the feedback you want to hear, but it's what you do with the feedback you receive to your advantage.
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#72 Homeless to Success: Ivan Presquito’s Journey of Resilience and Reinvention
On this episode of The Solo 2 Entrepreneur Show, my guest, Ivan Presquito shares his extraordinary journey from migrating across three countries to overcoming homelessness in New Zealand. Once a highly qualified CPA and MBA, Ivan faced unexpected challenges finding work, leading him to start from...
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#71 Women in Business - Raw Truth No One Says
Being a woman in business isn’t easy — and it’s time we talk about it honestly. In this episode, Lorraine Chai shares the raw truth about the challenges women face in business: the unspoken “bro code,” the constant need to prove ourselves, and the reality of working harder just to be taken...
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#70 Scrubs to Steaks: The Bold Pivot No One Saw Coming
Meet Lucinda Harris — once a small-town nurse, now running a profitable farm-flipping and direct-to-consumer beef business. In this episode, Lorraine uncovers how Lucinda turned rural struggles into consistent profits, pivoted at the right time, and even transformed her personal brand to own the...
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#69 The Habit That Separates the Winners From Everyone Else
If you're chasing success, it's already running from you. In this raw and unfiltered episode where we unpack the one habit that high performers practice daily — and why most people overlook it. You’ll learn: Why motivation doesn’t matter as much as your standard How to stop spiraling when your…
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#68 Engineer to Millionaire: Breaking Traditions, Taking Risks & Building an Empire
Ever felt trapped by traditions, family expectations, or the fear of leaving your ‘safe’ job? In this episode, Lorraine Chai sits down with Eng Ho, a Malaysian entrepreneur who migrated to Australia, walked away from an engineering career, and built a thriving laundry business empire. You’ll...
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#67 The Walls We Build: The Real Struggles Every Entrepreneur Faces
Being a business owner isn’t easy. Fear, doubt, mistakes, and failures are part of the journey. But too often, entrepreneurs build walls that hold them back from their full potential. In this episode, host Lorraine Chai reveals the raw truth about entrepreneurship: Why so many entrepreneurs fear...
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#65 The Inner Game of Business
Babies are fearless, curious, and absorb everything — because they’re built to evolve. But somewhere along the way, life conditions us to trade that growth mindset for comfort zones, doubt, and survival mode. In this powerful solo episode, Lorraine Chai unpacks her own recent growth challenges —...
About this show
Solo 2 Entrepreneur is the ultimate podcast for solopreneurs and small business owners seeking to thrive in business. Hosted by Lorraine Chai, a business strategist, each episode features interviews, discussions, and actionable strategies from industry experts. From mastering leadership to navigating digital marketing, ”Strategic Success” provides the tools and knowledge needed for entrepreneurial excellence. Tune in to unlock your full potential and build a thriving business.If you would like to know more about Lorraine, what she does, or want to work with her, check out her web link atwww.solopreneur2entrepreneur.com/linkRemember to follow, share, and leave a review. We would love to hear from you.
Hosted by
Lorraine Chai
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