HeyJaredThe Solo 2 Entrepreneur 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.
- Indexed episodes, last 90 days
- 10
- Latest publication
- Sep 21, 2026
- Audience
- Checking…
- Earliest in this view
- Jul 13, 2026
Latest episodes
#113 Survival Mode Is Not a Strategy - Here's What Is (opens the original)
Read excerpt
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 figures and her closest friend in the same month - during COVID - and came out the other side with a
#112 The Real Game Reveal "The Deal Was Never the Deal" (opens the original)
Read excerpt
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 that keeps his pipeline full without a single cold pitch. 🔗 Conne
#111 Why the Quietest Person in the Room Is Usually Winning (opens the original)
Read excerpt
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 episode is for every solopreneur and business owner who has ever overshared in the wrong room, felt
#110 Nobody Warned Me About This: The Hidden Cost of Business (opens the original)
Read excerpt
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 you've ever felt misread, underestimated, or completely alone on this journey, this one is for you.
#109 From $25 Million to $400: The NFL Star Who Lost It All and Built It Back (opens the original)
Read excerpt
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 lines, his home-and arrived in Raleigh, North Carolina with $400 to his name. He got fired from two jobs
Publishing over time
Last 90 days. Choose a month to open its work.
Recurring subjects
Named in the text we hold. One piece can cover several.
Audience
No verified audience measurement yet.
About this data
Counts cover the work we have indexed. Tone needs enough text and a confident classification. Excerpts and episode notes are not full articles or transcripts.
Identity or attribution wrong? Suggest a correction.