I’m tired of working two jobs, but my tutoring business is still not making enough to support me. My dream is to be able to help any family, regardless of how much they can pay me. I know you’ll tell me that’s not feasible. Right now I tutor lots of kids and I don’t turn away anyone, no matter how much they can pay. How can I keep helping families who need me and still make enough money to pay my mortgage?

I always thought I’d have my own business by now, but life hasn’t worked that way. Specifically my wife and I had a baby and I wanted a proper job.

Now my wife wants me to start a business that will let me leave my job. She has a point, because I’m not one for sitting at a desk from  9-5. Yes, I hate it. But I would need to get a good deal of cash into that business at the beginning, and we don’t have much savings.  I have a few friends who said they could help me get investors, but I’ve seen all the trouble my friends had getting investors and I don’t know if I could do that.

 So I think I should go with a business idea that my wife and I could do together, for fun. I wouldn’t need to put money into the business. Well, we would have to have a little money, but we could use some savings. It’s just that I don’t know if I like that because the business would not let me quit my job. And my wife is pretty busy, but she likes projects.

You’ve had a lot of businesses yourself, Penelope. Do you know which business would be best for me?

Answer from Penelope:

Your goal for starting a business is to enable you to get out of going to an office from 9-5. That’s a good goal. And the smaller business idea will not meet that goal.

It seems that the only benefits to the smaller business is that you and your wife have fun. But you don’t need to invest your savings in order to have fun. And I’m sure your wife can find a project for herself without you starting a business for her.

So I think your real question is how can you gather enough funds to get the bigger business off the ground.

You are right to think that doing that is difficult, but starting a business that needs funding is often the most low-risk option on the table, and I think that may be true for you.

You have friends who understand the investment community, so it’s not outrageous to think they could guide you. And don’t underestimate the need for a guide – the startup funding community is relatively conservative with stringent rules. 

The game of launching a business is doing as much as you can to mitigate risk. So, for example, its risky to start a business to get out of your office job, but it’s riskier to plan to spend your life in a job you hate. Here’s a blog post about mitigating risk as you start a business. 

You’ll have an easier time beating out the competition if you stick to something you have expertise in. So your business should be at the intersection of the idea you like and the expertise you have. You can find practical examples of leveraging your expertise in the book The Business of Expertise, by David Baker. 

Don’t shy away from borrowing money. There’s a reason that most entrepreneurs have bad credit— you have to use anything you can get to keep your business from going under during those early, fragile months. That said,  business owners who have a plan to be profitable often qualify for fast business loans.

If this is all making you sick with stress, try a career change. Just because you hate one job doesn’t mean you’ll hate them all. I would not recommend going back to school for a graduate degree — way too large an investment for something you’re not sure of. But going to a career development site that provides you with a mentor in your field is a good way to make the career change less difficult by helping you to create a network to pave the way.  NYICD does a good job of providing that service. 

And remember that there is no way to live a life without taking some risk. When you ask people at the end of their life what they would have done differently, they almost always say they would have taken more risks. So instead of avoiding the risks of doing the business that meets your goals, try thinking in terms of intelligent risk-taking and then you’re not likely to regret the outcome, no matter what it is. 

I am launching a new online marketing platform that will allow brands to connect with (potential) customers globally in a completely new way. The biggest component of the business is partnering with various large and medium size brands that are willing to experiment with their marketing approach and product offerings.

Until now, I was working on devising the business plan and the operational aspects of it but now is the time when I have to penetrate the C-Suite, specifically the Chief Marketing Officer suite at those brands with my partnership proposal. I am not sure how to go about it.

Do I sent emails, pick up the phone, send letters? Do I prepare a “pitch deck” that I email the brands or send them or a top view summary page? I am totally unconnected to those brands and they span across various industries. Any ideas or insights would be appreciated!

I’m launching an online marketing platform to connect brands with potential customers in a completely new way. The biggest component of the business is partnering with various large and medium size brands that are willing to experiment with their marketing approach and product offerings. Until now, I was working on devising the business plan and the operational aspects of it but now is the time when I have to penetrate the C-Suite, specifically the Chief Marketing Officer suite at those brands I want to sell to. I am not sure how to go about it. Do I sent emails, pick up the phone, send letters? Do I prepare a “pitch deck” that I email the brands or send them or a top view summary page? I am totally unconnected to those brands and they span across various industries. Any ideas or insights would be appreciated!