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The Solo 2 Entrepreneur Show

The Solo 2 Entrepreneur Show

Lorraine Chai 102 Episodes Oct 12, 2026

The Solo 2 Entrepreneur Show, hosted by business strategist Lorraine Chai, is a podcast for solopreneurs and small business owners. Each episode features interviews with industry experts and discussions on actionable strategies for business growth. Topics include mastering leadership, navigating digital marketing, and achieving entrepreneurial excellence. The show aims to equip listeners with the tools and knowledge to build a thriving business.

Episodes

#115 Your Business Is Growing. So Why Aren't You Getting Richer? (Ernest Smith)
#115 Your Business Is Growing. So Why Aren't You Getting Richer? (Ernest Smith) Oct 12, 2026 2419 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 like a true entrepreneur. From managing 18 employees and discovering the hidden costs of growth to expl
#114 I got Fired
#114 I got Fired Sep 28, 2026 1443 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 behind why it happens reveals more about the business, the leadership, and the opportunity in front of you
#113 Survival Mode Is Not a Strategy - Here's What Is
#113 Survival Mode Is Not a Strategy - Here's What Is Sep 21, 2026 986 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 changed, the original path was gone, and panic set in fast. Lorraine has been there too. She lost six f
#112 The Real Game Reveal "The Deal Was Never the Deal"
#112 The Real Game Reveal "The Deal Was Never the Deal" Sep 14, 2026 1811 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 this episode, John breaks down why most entrepreneurs flame out, what "911 networking" is costing you,
#111 Why the Quietest Person in the Room Is Usually Winning
#111 Why the Quietest Person in the Room Is Usually Winning Sep 7, 2026 905 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 all had in common: they listen more than they speak, and they choose their words with precision. This
#110 Nobody Warned Me About This: The Hidden Cost of Business
#110 Nobody Warned Me About This: The Hidden Cost of Business Sep 1, 2026 413 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 room - and more importantly, what happens when you choose to grow through it instead of giving up. If
#109 From $25 Million to $400: The NFL Star Who Lost It All and Built It Back
#109 From $25 Million to $400: The NFL Star Who Lost It All and Built It Back Aug 25, 2026 1870 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 redemption stories in business. Marques didn't just lose money. He lost everything-his company, his credit line
#108 Living my Plan C until I got slapped
#108 Living my Plan C until I got slapped Aug 17, 2026 917 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 when life feels heavy, and you still have to move forward. What to expect in this episode: The moment I r
#106 You’re Not Shy. You’re Strategic: The Ambivert Advantage in Business
#106 You’re Not Shy. You’re Strategic: The Ambivert Advantage in Business Aug 3, 2026 993 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, and grow without burning out.
#105 They Judged Me in Seconds: Turn It Into Power
#105 They Judged Me in Seconds: Turn It Into Power Jul 27, 2026 1054 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 underestimated, this episode gives you a simple rule you can use today.
#104 The Shift Nobody Talks About: How Diego Munoz Went From “Starting Over” to Owning the Room in Business
#104 The Shift Nobody Talks About: How Diego Munoz Went From “Starting Over” to Owning the Room in Business Jul 20, 2026 2466 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 episode is not just about money or titles. It’s about the internal shift: choosing growth on purpose, sta
#103 Comfort Zones Are a Myth
#103 Comfort Zones Are a Myth Jul 13, 2026 763 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 performers think about frugality, convenience, and priorities, and how to pivot without burning cash, losing mom

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