Starting a Business With Nothing

Sean S. in Eureka CA, a house painter for 6 years, and his girlfriend, who has her own cleaning business, wrote in and asked, “Bob how do we get the painting and cleaning businesses up and going again after I am released from prison?”

Thanks for writing, Sean! 

Starting over is tough but not impossible. 

I’ve been where you’re at and can tell you that while starting over is very tough, it’s not impossible, especially when you have what you have going for you. You’ve been in business before so you know how to do the work, and what’s required to run a business and sell jobs. Plus, I’ve always said if you can survive jail or prison then you can do anything. 

I think re-starting the businesses might not be as hard as you think. Start by getting a free Gmail email account and a smartphone then put free ads on Facebook Marketplace and Craigslist. Create a free Facebook Business Page to act as your website until you can afford to get one. 

With the worker shortage, there is a huge demand for painters and cleaners. When you’re bidding on a painting job, make your bid (and downpayment) high enough for materials and to rent or buy the equipment you need. Keep using rented equipment until you can afford to look on Facebook Marketplace and Craigslist for used equipment. You won’t get every job you bid on, but you will get work and can go from there. Repeat the process until you can upgrade your equipment if needed. 

For the house cleaning business, post the same free ads to get initial customers. You can’t get down payments on cleaning jobs to buy cleaning equipment, but house cleaning tools are a lot cheaper than sprayers and ladders! 

Start small and build your way back by doing great work and making happy customers. 

When you get a job make a social media post. Also post progress pictures during the job, and completion pictures when done.  People watch those posts and when people know you do quality work they can refer business to you. Seeing pictures helps to keep your businesses on their mind. 

Don’t forget to sell cleaning services to your painting customers, and for your girlfriend to sell painting services to her cleaning customers. 

You might have to work for another company for a little bit to earn enough money to get started again. Doing that could give you some new customers right out of the gate, too. 

Starting or restarting a business is hard, but not as hard as being incarcerated!

Good luck with your business relaunch when you’re released. 

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© 2022 Pelshaw Group, Inc. Used with permission.

Ask Bob is an advice column by Bob Pelshaw, formerly incarcerated citizen, successful entrepreneur, speaker, and author of the award winning Illegal to Legal: Business Success for the (Formerly) Incarcerated. (Book and workbook available on Amazon). Bob also provides content to Edovo, GTL, PayTel, and jails and prisons nationally.

Ask Bob answers questions about life, successful re-entry, starting a business and entrepreneurship, and most anything that adds value, except the column does not cover legal issues, sentencing matters, or case issues. To ask Bob a question, write to him at:

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