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 have an idea for a company, and I have basic skills for writing code. Can you recommend good books or guides for how to take a startup idea and get funding and launch it?

I can’t stop thinking about a potential investor who is trying to get me to sleep with him. I live in Silicon Valley and he’s an active angel investor with a great reputation. So, to say I was excited when I got my first meeting with him would be an understatement. He’s personable and immediately seemed interested in my company’s vision.

Our first couple of meetings were all business. Then he started sending me flirty texts. Then he tried to kiss me.

The truth is I want to work with him but I have no interest in sleeping with him. I’m now worried that we’ll never be able to have an exclusively platonic business arrangement because he’s crossed the line with me. I’m also worried that he’ll back out of funding my company or worse yet, potentially poison the well with other investors by saying negative things about me if I don’t go along with it. People around here are so fickle that all it takes is for one “popular” investor to say an entrepreneur is incompetent for that to become accepted in the echo chamber.

So, I feel torn. I either shut him down completely and risk his wrath, or literally “take one for the team” and start sleeping with him in order to get continued access to his contacts and money.