The Solo 2 Entrepreneur Show
Lorraine Chai created The Solo 2 Entrepreneur Podcast. Join us as you listen to interesting topics or interviews with celebrities or successful entrepreneurs about the World of Business from the ground up and tricks that you can implement in your business growth. If you would like to know more about me, what I do, or want to work with me, check out my web link at www.solopreneur2entrepreneur.com/link. Remember to follow, share, and leave a review. We would love to hear from you.
Episodes
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, and the counterintuitive long game ...
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 preci...
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 giv...
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 ...
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.
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.
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.
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&rsqu...
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, an...
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 continuing to lead with duty and care even as his health declines.
...
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&...
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 one-and-done exit myth, and what it really takes to build an “empire” with a clea...
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 place flags, the quiet energy of unity, and the surprising moment the sky held off the rain and delivered a rainbow. I also reflect on w...
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 asking better questions became the pivot point for my confidence and results. You’ll leave with a simple fram...
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 really like building a business as a couple: lanes, feedback, honesty, and how they’ve used AI-driven systems&...
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 protecting your potential, this is your wake-up call.
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, whether you’re in your 20s, 40s, or 60s. If you’re still listening, something here is calling you higher.
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 shifts, the story behind his gold shoes, and why communication beats charisma.
- Facebook: @mayorjacquesgilbert
- Instagram: @mayorjacquesgilb...
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, and lead your venture with unwavering purpose. Tune in to start your journey from reactive chaos to proactive control.
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 transform unpredictability into opportunity-without needing to have all the answers. Tune in and learn how to reclaim your business...
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