Guest Speaker: The Oracles “11 Ultra-Successful Entrepreneurs on How to Start Over If You Lose It All”

What happens when everything falls apart and you lose it all? These very successful entrepreneurs and members of The Oracles, who have all started from scratch more than once, explain what they would do next if they lost it all again.

1. Cover rent, then start another business.

I’d hop into a promising business and start selling because that’s what I’m good at. The minute my rent was covered, I would start a business. It wouldn’t make much of a difference if it were a hot dog stand on the corner or a technology startup, as long as I believed wholeheartedly in the product.

2. Build a blockchain government.

Blockchain technology speeds up transactions, reduces costs and lowers the chance of fraud. Think of it as a shared ledger and database that no one can manipulate. All data is fully transparent. If I had a mantra to rebuild after my fresh start, it would be, “Promote freedom at all costs.”

3. Read history and surround yourself with friends.

First, I would read history. Without a sense of history, you feel like what’s happening to you is a once-in-a-lifetime event that nobody’s ever dealt with. Understand the great falls others have recovered from.

There will be peaks and valleys. When in the valleys, don’t isolate yourself. Humans are social animals. No matter how bad it gets, it’s good to think about the funeral test: if you have at least 150 people who would show up at your funeral, you’re good. Your network is a great safety net; there’s a lot of science to indicate it’s the best way to recover from depression, anxiety and nastiness.

4. Spend three days mourning, then mount your comeback.

I’ve failed enough times in businesses that making a fresh start is familiar. I give myself three days to mourn the loss of a business or a major failure. After that, I’d make a plan to build the capital and infrastructure to execute my comeback. I set reminders multiple times a day to stay on top of executing my new plan.

 5. Turn disaster into opportunity.

This actually happened to me 20 years ago, so I don’t have to imagine this happening. I found myself kicked out of a company that I helped grow 300 percent. When this massive loss happened to me, I decided it was time for me to have my own business and be the master of my own fate. I never lost faith in my abilities. I focused on my ability to make things go right. I stayed positive and used a devastating event to force myself to think bigger than ever before.

6. Hit the brakes, change direction and speed back up.

If I were to start again, I would stop and get “in state” be in meditation and quiet, and just focus on my desired outcome for a new venture. I’d set my goals, strategise, build a team around it, and empower them with a “why” that is greater than money or incentives. Then, attend to marketing, operations and finance know your numbers. And remember: it’s a marathon, not a sprint.

7. Assess your sources of capital.

If you lost everything, you have two choices: quit on yourself or look in the mirror and answer a few serious questions. Start with: “What life capital (relationship, intellectual, physical, spiritual and financial) can I immediately access to start over?” Understand that life provides constant feedback: you’re required to review the outcome and modify your thoughts, words, and actions to create the desired result.

8. Share your new vision immediately.

If you are an entrepreneur, you should be starting over every year, anyway. You need to refresh systems, people, processes and financials. Start with what you like, what you’re good at and where there’s a market need. Create a compelling video. Share your vision. You can test the market before investing more deeply.

9. Cut overheads and reinvent though travel.

Studies have shown that travel improves creativity, reduces stress, and emotionally recharges you. I would pack light and start again in Thailand. Having fewer possessions and distractions would free up energy to execute my comeback. An unfamiliar environment would initiate fresh ideas.

Living expenses should only be around $1,000 per month. While doing yoga and drinking mango smoothies, I’d reflect on where I went wrong and strategize my next steps. Through the internet, I’d sell products or services to customers in wealthy countries.

10. Find your why.

I lost it all three times. From experience, your mindset is everything. Take the time to reset your attitude. Losing it all is very hard, even devastating, but lingering around with a loser’s attitude makes everything harder. No pity parties! Then, identify the reason you built it all in the first place. What was the purpose? Use that as your core motivation to rebuild. All dramatic events will pass, but we must choose our direction during the aftermath: up or down.


 11. Network like crazy.

Learn who’s in your tribe. Identify your values and have a list of questions to determine if someone shares your vision. Then, spend as little as possible to attend as many events as possible to meet a diverse group of people who could help you. Even sit in the lobby without a pass — you’ll probably get one after connecting with the right people. Be fearless and talk to everyone. Get to an event by 7 a.m. and sit at the bar until 1 a.m. — just to talk to one more person. Learn how to own a room and don’t be afraid to ask for help.

Related: 10 Books Every Leader Should Read To Be Successful

Related: 22 Qualities That Will Make a Great Leader

The Oracles is an invitation-only brain trust comprised of the world's leading entrepreneurs who share their top advice and success strategies to help others grow their business, live a better life, and achieve success faster.

The Oracles



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