A popular Gen Y blogger talks about exactly what it took to transition from freelancer to small business owner.

So there’s this awesome job, the sort of job you’d just die to land (and tell your friends about)! But the awesome job isn’t nearly like the job you have now. So how do you make it from current job to awesome job?

In our new podcast series, we’re hoping to provide insights and answers to that very question. We talk to young people who have amazing jobs or are doing something really cool and interesting and ask them how they did it. So listen along for good information and some inspiration, too.

This week’s guest has done something a lot of people dream about — start a business. But it wasn’t really planned.

Matt Cheuvront decided to become an entrepreneur “a couple of hours” after suddenly getting the boot from his Internet marketing job in 2010. Losing the job provided Matt with an opportunity to explore his side web design business and see where he could take it.

After working on his own projects for a couple of months, Matt connected with Sam Davidson, and Proof was born. Now, just over a year after they started the company, Proof is generating between $20,000 and $30,000 per month.

In the interview, Matt talks about exactly what it took to get there and where he’d like to see things go. All in all, there’s a ton of tactical information in the interview for anyone thinking about self-employment and entrepreneurship.

Here are some snippets from our conversation, which have been slightly edited for context.

On making the leap to being an entrepreneur:

“The one thing that separates those who want to be doing their own thing  and those who are is action. I decided I wanted to be an entrepreneur a couple hours after I lost my job. That’s a little bit dramatic, but what I did initially when I decided I was going to do my own thing …   I told myself i was just going to sustain myself to the point where I could take a job I actually wanted. Up until that point, I had graduated college, got a job, I moved to Chicago. I just had to get a job to make money … I wasn’t able to hold out for something I really wanted.”

On the skills needed to start a company:

“I didn’t want to be and I don’t want to be a web designer or a web developer. I picked up those skills sort of on the fly over the past few years. What I tell folks who are starting a business of their own is you have to have something tangible. It’s very difficult to say I’m a consultant, especially at 25 years old with very little experience …  it’s sort of wishy-washy and there are so many folks out there who are consultants. … I picked up web design because it’s tangible, it’s a product you can sell and market.”

On working a lot to get the business of the ground:

“What separates people who are successful from people who aren’t is the hustle. It is the hard work, it is putting in the time that other people may not be willing to.”

Matt Cheuvront

Download the podcast here or listen now:

Check out Matt’s blog or say hi to him on Twitter. Additional questions or comments? Leave ’em in the comments!

Jaclyn Schiff, a journalist/media consultant, is managing editor of Brazen Life. To learn more visit her website or follow her on Twitter.


  1. Natalie

    Really nice article, lol my brother tried to start a business but unfortunately didn’t do to well… then again its not really a shame since 90% of all new businesses fail.

    • Jaclyn Schiff

      Thanks Natalie! I’ve heard lots of different statistics on the number of new businesses that fail… not sure which one is really accurate, but it sure is tough to get something off the ground! So it’s super helpful to hear from people who have actually done it.

  2. Alexis Grant

    Great interview! Awesome to get the inside scoop from Matt after following his blog. Nice work, Jacci.

  3. Anonymous

    A good business Idea self confidence market research and above all a handsome amount to start a business.

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  4. Jrandom42

    So what about those of us who have no enterprenuerial bent or inclination? No amount of freedom and rewards is worth dealing with the hassles of marketing, selling, finances, taxes and other bull. Just let me concentrate on the technology I know best and do that part.

    I guess, at this late stage in my career evolution, I ( and millions like me) are just screwed.

  5. Anonymous

    After starting several businesses I concur it ain’t no walk in the park. But it’s totally worth it! Here’s a special Colbert tip of the hat to every entrepreneur out there.

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