Entrepreneurs

Council Post: Leadership Lessons From ‘Undercover Billionaire’: Ask Questions

By Tommy Mello, owner of A1 Garage Doors, a $100M+ home service business. Sharing what I’ve learned to help other entrepreneurs scale.

If you had $2,000 in your bank account, would you pay $1,500 just to talk with an expert?

That’s what Glenn Stearns did in the first season of Undercover Billionaire.

Undercover Billionaire is a television show that takes a billionaire, puts them in a town they’ve never been to with nothing but a car and $100, and gets them to build a $1 million business in 90 days—all without using their name or reputation.

After a week, Stearns managed to turn the $100 into $2,000, and he had a business idea. And the first thing he decided to invest in? A 15-minute call with an expert that cost him $1,500.

Is that crazy? No. Here’s why: The expert, who was a world-class lawyer, told him to forget about that idea and gave him a series of reasons why it wouldn’t work.

Most people would have taken months if not years to figure out what the lawyer already knew. And at that point, they would have invested too much time and money into the idea. With one phone call, Stearns prevented all that heartache upfront and set himself free to pursue a better business idea. How’s that for efficiency?

Here’s the thing that I keep saying to people: The “I’ll figure it out myself” mindset is what holds most people back from being successful leaders or entrepreneurs.

Rather than trial and error, billionaires like Stearns understand the value of their time. They buy time by paying people for the answers they don’t have yet—so that they avoid mistakes that destroy the business they’re building and also find proven strategies that help them grow faster.

And trust me, that’s exactly how I’ve grown my garage door business to $150M: by asking the right people the right questions.

Over the last few years, I’ve invested hundreds of thousands of dollars and spent hundreds of hours with experts all over the country and gotten them to share their knowledge with me.

With my podcast alone, I’ve interviewed over two hundred entrepreneurs and leaders—just so I can learn from them. Here are a few of my favorite questions to figure out what makes them successful:

1. What are the top three books that you would recommend to everyone?

2. Where do you find the best people to hire?

3. How do you allocate your marketing budget?

4. What are your thoughts on AI, Millennials, etc.?

This doesn’t just apply to entrepreneurs and leaders. Encourage your employees to get in the habit of asking to help bring their careers to the next level.

When I ask my best salespeople, “How on earth did you sell that!?” They often laugh and say: “All I did was ask.”

So, if you want that promotion or that dream job, you need to ask! Yes, you might get rejected. You might ask the wrong person. You might ask the wrong question. Failing isn’t fun. But hey—it’s better than not living the life of your dreams.

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