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Losing Millions, Making Millions, and Why Reinvention Is a Skill
Entrepreneur and sales strategist Doug Brown joins me to unpack what really happens when success collapses—and why the ability to rebuild matters more than avoiding failure.
Most business conversations glamorize wins and sanitize losses. This episode does neither. Doug Brown and I walk through the uncomfortable reality of losing millions, starting over with almost nothing, and repeatedly reinventing yourself when the old path no longer works. From early failures in telecom and software to rebuilding after financial wipeouts, Doug shares what persistence actually looks like beyond motivational slogans.
We explore why “safe careers” are an illusion, how low burn rates create optionality, and why scrimping alone won’t build a meaningful life. This is a candid conversation about volatility, personal identity, money, family, regret, and why wisdom often comes from getting knocked down—then learning how to get up faster the next time.
The lesson isn’t masochism or chaos. It’s designing a life and business resilient enough to absorb hits without losing yourself in the process.
TL;DR
* Reinvention isn’t a phase—it’s a permanent skill in modern life.
* Failure isn’t the problem; slow recovery time is.
* Low burn rates create flexibility and asymmetric upside.
* “Safe” careers can disappear faster than risky ones.
* Wealth without alignment creates loneliness, not freedom.
* Cash flow matters more than cash hoarding.
* Regret comes more from inaction than from failed attempts.
Memorable Lines
* “It’s not the setback—it’s how fast you recover.”
* “Live modestly so your life becomes a call option.”
* “Money lets you arrive at your problems in style.”
* “You only have to get it right once to set yourself free.”
* “All the chips get pushed back to the middle eventually.”
Guest
Doug Brown — Entrepreneur, sales strategist, and founder of CEO Sales StrategiesFormer president of Tony Robbins’ companies, advisor to global organizations, and veteran of 37 businesses across multiple industries.
🔗 https://www.ceosalesstrategies.com🔗 LinkedIn: Doug Brown 123
Why This Matters
The future doesn’t reward stability—it rewards adaptability. Careers reset. Industries vanish. Businesses fail. Understanding how to rebuild after loss isn’t pessimism; it’s realism.
For founders, operators, and executives navigating volatility, this episode reframes failure not as an identity—but as data. The real edge isn’t never falling. It’s learning how to stand back up without losing clarity, relationships, or purpose.
This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.dougutberg.com
View all episodes
By Doug Utberg
4.9
3434 ratings
Entrepreneur and sales strategist Doug Brown joins me to unpack what really happens when success collapses—and why the ability to rebuild matters more than avoiding failure.
Most business conversations glamorize wins and sanitize losses. This episode does neither. Doug Brown and I walk through the uncomfortable reality of losing millions, starting over with almost nothing, and repeatedly reinventing yourself when the old path no longer works. From early failures in telecom and software to rebuilding after financial wipeouts, Doug shares what persistence actually looks like beyond motivational slogans.
We explore why “safe careers” are an illusion, how low burn rates create optionality, and why scrimping alone won’t build a meaningful life. This is a candid conversation about volatility, personal identity, money, family, regret, and why wisdom often comes from getting knocked down—then learning how to get up faster the next time.
The lesson isn’t masochism or chaos. It’s designing a life and business resilient enough to absorb hits without losing yourself in the process.
TL;DR
* Reinvention isn’t a phase—it’s a permanent skill in modern life.
* Failure isn’t the problem; slow recovery time is.
* Low burn rates create flexibility and asymmetric upside.
* “Safe” careers can disappear faster than risky ones.
* Wealth without alignment creates loneliness, not freedom.
* Cash flow matters more than cash hoarding.
* Regret comes more from inaction than from failed attempts.
Memorable Lines
* “It’s not the setback—it’s how fast you recover.”
* “Live modestly so your life becomes a call option.”
* “Money lets you arrive at your problems in style.”
* “You only have to get it right once to set yourself free.”
* “All the chips get pushed back to the middle eventually.”
Guest
Doug Brown — Entrepreneur, sales strategist, and founder of CEO Sales StrategiesFormer president of Tony Robbins’ companies, advisor to global organizations, and veteran of 37 businesses across multiple industries.
🔗 https://www.ceosalesstrategies.com🔗 LinkedIn: Doug Brown 123
Why This Matters
The future doesn’t reward stability—it rewards adaptability. Careers reset. Industries vanish. Businesses fail. Understanding how to rebuild after loss isn’t pessimism; it’s realism.
For founders, operators, and executives navigating volatility, this episode reframes failure not as an identity—but as data. The real edge isn’t never falling. It’s learning how to stand back up without losing clarity, relationships, or purpose.
This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.dougutberg.com