Drew Rogers built My Language Lab from scratch as a solo founder — no co-founder, no safety net, just grit and an idea she refused to let go of. Over seven years, she grew it into a company trusted by names like Amazon, Disney and Sky, navigating everything that comes with building something from nothing: the early days when nobody's watching, the pressure of every decision resting on your shoulders, the moments of doubt that never really go away even when things are working. It's a story about resilience as much as it is about strategy — about what it actually takes, day after day, to keep a business alive when you're the only one holding it up.
Then she sold it. And that's where this conversation gets even more interesting — because nobody really talks about what happens after. Drew opens up about the identity shift that comes with letting go of something you built with your own hands, what a typical week actually looked like once it was no longer hers, and whether the "founder's remorse" people talk about is real.
We also get into the quiet sixteen years she spent building a property portfolio alongside the business, what she's learned about mentoring others trying to find their own path, and the honest realities of talking to the next generation about entrepreneurship — the parts that are inspiring, and the parts that are genuinely hard.
This one goes beyond the usual "how I sold my business" story. It's about the grit it takes to build, the strength it takes to let go, and what's left of you once the thing you built is no longer yours. Money Made Simple — real conversations on business, leadership, and the decisions that shape long-term growth.