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4
Lisa Kipps Brown
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Why This Episode Matters
Lisa Kipps Brown has been an entrepreneur since 1990, has built and sold multiple businesses, created one of the first subscription-based online platforms in the late 90s, and now advises a NASCAR team using B2B consulting rather than traditional sponsorship. In this conversation, she reveals the three questions that unlock any business problem, why her blind father taught her that obstacles are just detours, and how giving away what you're best at always comes back to you. For entrepreneurs seeking unconventional paths and anyone ready to disrupt their own status quo, this is a masterclass in asking "what if?"
Key Takeaways
The three magic questions: Why? Why not? What if?
These questions unlock everything. Why are you doing it this way? Why not try something different? What if you did the craziest thing imaginable? These questions opened doors Lisa never expected.
Her blind father was a human Roomba
If he bumped into something, he backed up and found another way. He never said "I can't." He used power tools, rode horses, played basketball. Growing up with that 24/7 made Lisa believe anything is possible.
Build a business that fits the life you want
Most entrepreneurs model their business after others without asking what they want their daily life to look like. Start with lifestyle—then build the business around it.
One of the first subscription businesses online
In the late 90s, Lisa helped a client on the verge of bankruptcy pivot from print books to an online subscription model. Two years later, they sold for 20x the investment—right before the dot-com bubble burst.
NASCAR without traditional sponsors
Lisa advises a NASCAR team that doesn't chase sponsors. Instead, they provide B2B consulting to solve specific business problems. The racing is incidental—profits fund nonprofits on the car.
Conversation Outline
00:00 — "If you can figure out a way to use your gifts to help people, it always comes back"
01:00 — Entrepreneur since 1990, current business since 1996
03:00 — Growing up with a blind father who did everything
05:00 — The human Roomba: backing up and finding another way
08:00 — The three questions: Why? Why not? What if?
12:00 — Creating one of the first subscription-based online businesses (late 90s)
15:00 — 20x return in under two years—right before dot-com bust
18:00 — Build a business that fits the life you want to live
22:00 — NASCAR team without traditional sponsors: B2B consulting model
28:00 — First braille paint scheme in NASCAR history
32:00 — Parents who welcomed Mexican migrant workers—curiosity over fear
38:00 — Crowdfunding for stem cell treatments for a veteran
42:00 — Leading with giving: it always comes back
45:00 — Disrupt Your Now (book) and Boomer Cash Out
Lisa Kipps Brown
→ Entrepreneur since 1990 — built and sold multiple businesses
→ Author of "Disrupt Your Now" and "Boomer Cash Out"
→ Created one of the first subscription-based online businesses (late 1990s)
→ NASCAR team advisor — pioneered B2B consulting model for racing
→ First braille paint scheme in NASCAR history (with blind-owned sponsor)
→ Former CPA and controller for an international software company
Show Notes & Links
Mentioned In This Episode
→ Disrupt Your Now — Lisa's book on disrupting the status quo
→ Boomer Cash Out — book on using web to make business sellable
→ NASCAR / Colin Garrett — racing team Lisa advises
→ Hobie — Lisa's blind friend, first blind-owned NASCAR sponsor
→ Daytona 500 — race Lisa has worked with drivers on
→ BJ Fog — behavioral designer, referenced for habit research
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