Killer Interview Question: If You Won The Lottery, What Business Would You Open?

Killer Interview Question: If You Won The Lottery, What Business Would You Open?

In this week’s KIQ,we want you to picture yourself rolling around in cash and then think about what business you would start with that money.

Rich man with some ladies image from Shutterstock

Dottie Mattison is the CEO of Gracious Home New York, a furnishings company, and she’s not someone who likes to grill job candidates in an interview. Instead, she likes to build rapport with them by asking fun questions. The more comfortable an applicant is, the better she can see what kind of person they really are.

One of these questions is “If you won the lottery, what business would you open?

Speaking with The New York Times, Matthison explains:

“Sometimes that turns out to be a product category they know a lot about, or a certain customer they understand really well”.

Many of us have great ideas for a product or business but are held back by lack of funding. By removing the money barrier, Mattison hopes to encourage creative thinking that is not constrained by reality.

How would you answer this question? Let us know in the comments.


  • Money no object, I would open a racetrack and driver training park to get young drivers off the street.
    If it made the streets safer and gave young people a chance to test their skills at a very low price and learn new techniques then that would increase the safety on public roads from dangerous drivers and riders.
    There would be all types of racing from drifting, rally, motorcycles and skidpan sessions.
    There are already places like this but motorsport parks are expensive and are domiated by people with a lot of money to pour into their own cars and racing hobbies.
    I would approach the government for subsidies, local law enforcement and ambulance services for support and do talks at high schools about driver training so all see that it can be enjoyable and affordable.
    Of course there would be a profit generating racetrack for full fledged racers and hobbyists. There would be sponsorship opportunities for local businesses.
    The key is easy and cheap access for young drivers. Somewhere people wont be daunted to go to because they don’t have money or they feel they aren’t in with the ‘track crowd’. I would have programs through schools and also memberships that encourage being safe on the road. Eg. Discounted or free years for drivers with clean records.
    If they just want to thrash their car (must be registered in their name or consented to) then they can have a skidpan session or drag session in a controlled environment with medical support on standby.
    Ideally it would create jobs and generate enough cash to sustain itself. If it saves any lives on the road then it is a good business.

  • If money wasnt a problem, I’d do a range of things. First thing would be to set up a process where money was guaranteed. Wouldnt need to be much, just enough to cover the day to day costs of living, so a handful of rental properties would do the job.

    Next, I’d do something that let me get to know the local community. Something like a mobile coffee van, where you really get to talk to people. Thats as close as I’d get to retail though, and really as something just to mix things up a little. But that wouldnt be about money, it would be about connecting to people and possibly building networks.

    Mostly though, I’d want to be setting up some sort of development playground for technology. Use programming, engineering, even music in ways that come together. Luckily I’m in a University city, and my sister lectures there, so it wouldnt be too hard to set something up, but that would be my idea.

    Create a development playground for that next generation to turn their theory into practice as they go along.

    Outside of that, I have some ideas for property development I’d really like to try to see if they work. A couple of ideas that could deliver reasonably affordable housing without too much change. One in particular that, if it worked, would pretty much work anywhere.

  • A Vulture Fund, there’s plenty of opportunity on a continual basis……..

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