A man who went from delivering pizza to earning 6 figures shares the best insights he gained from years of taking successful people to lunch

Dan henry radioCourtesy of Dan Henry, via FacebookDan Henry gives a radio interview.

Dan Henry started working as a pizza delivery boy in the Chicago area at age 16.

Fed up with “trudging through six feet of snow, up six flights of stairs to get a $2 tip,” he set his sights on something more, and spent two years learning everything he could about running an online business.

“I would read these stories, like ’18-year-old kid started an office chair site and makes $1 million,’ and I was just like, ‘I want to be one of those guys.’ I just decided,” he told Business Insider.

As part of his research, Henry made a habit of cold-calling successful people and offering to take them to lunch.

“I decided to actively seek people out who were doing good, maybe not great, but people on their way who were more attainable, and talk to them personally,” he said. “I saved up money from delivering pizza and offered to take these business people and millionaires out to lunch and asked them questions. I was just trying to listen to a lot of people, start connecting the dots, and see where patterns emerged.”

He ended up having one or two lunch dates each month and was able to pinpoint a few common threads that helped him create his own success. A little over a year after launching his first entrepreneurial venture, an e-cigarette blog, he was earning $30,000 a month in profit.

When Google changed its algorithms and his earnings started to slow, he switched paths to brick-and-mortar businesses, reviving two local bars through Facebook ads and flipping them for a profit.

Today, having secured six-figure annual profits, he’s turned his attention to helping others achieve their own entrepreneurial success through private coaching and courses.

Those initial conversations with successful people taught him:

The little stuff doesn’t matter

“Most of the things that entrepreneurs worry and care about don’t matter. Like your logo: No one cares. How fancy your site looks: No one cares. Whether or not you use proper English: No one cares. I’ve had people say, ‘I don’t like how you use that slang,’ and two days later their credit card comes through for $997. I learned it just doesn’t matter. I have a site, but it’s just, ‘Hey, this is who I am.’ All my sales go through funnels, not my site.”

You have to get personal

“Another thing I learned, especially for online entrepreneurs, is that when you’re online, you have to break through that impersonal disconnect. It’s not a big challenge when you’re live, but when you’re not, you have to make yourself seem human. If you have to use profanity, if you have to wear funny clothes, that’s fine.

“To sum it up: Don’t be professional, ever. Don’t ever be professional because it’s boring. Everyone is professional. Be a real person. The last time I was interviewed on CBS, I wore a Batman t-shirt. If people see you’re comfortable in your own skin, they say to themselves, ‘I want to be comfortable in my own skin.’ It may not be the same skin, but you’re still comfortable.”

Outsourcing is invaluable

“Another thing: outsourcing. They all outsource the menial things.”

The more successful you are, the more you have at stake

“One more thing I learned is that once you start making money and start having a lot, it’s a lot easier to lose than when you don’t have money. That happened to me — I was making $30,000 a month and I was doing really great for a long time, but that was mostly SEO because that’s what I’d learned. When that train came to a stop, I lost that entire income. It was gone. I still had money in the bank, but I got angry at the whole internet thing. I opened some nightclubs, flipped some businesses, but then I missed that sitting on my butt lifestyle. When I sold the club, I started taking on Facebook ad clients and got back on my feet financially. I thought, ‘I can teach other people to do this because I’ve done this so many times.'”

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