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 launched a website very recently for women starting over in mid-life. My tagline is, “Be Your Own Rescuer”. I want to create a community of support and information for women starting over at a point in their lives when they thought they would be settled. I will offer entrepreneurial opportunities, feature other women who’ve been through it, a blog, private Facebook community, etc..

When I was in that situation, I was in despair. After my divorce I thought all the good in life was behind me. But I started cleaning houses and then I realized I could grow the business by hiring people. So I quadrupled my sales and I have ten employees. Now I want to do more. I want to show women to know they don’t have to settle for the crumbs of the life they lost.

A few things I’m working on:

I am creating a course on how to start a cleaning business, with support from me through the process.

I am also creating an 8 week group coaching course for these same women. At the end of the 8 weeks, I want them to have a plan and know what next steps they will take toward creating the life they want….

My first step is putting a bunch of irons in the fire to build a mailing list, direct them to my site, by offering freebies online through Facebook ads and instagram. Possible example: Offer the overview module to the courses for free, save the meat for the paying. Create freebies my target would be interested in: controlling negative thoughts, overcoming fear and worry, 7 days of radical self-care, the number one thing I did that changed everything, how I went from homeless single mom to successful business owner with healthy, happy, grown sons, “Be Your Own Rescuer” – how I rebuilt my life in midlife, etc….

I could also join online groups catering to my target market, get face-to-face with divorce recovery groups, addiction recovery (addiction and single mom can go hand in hand at times…), single moms groups. Write blog posts relevant to my target, share them online..

My question for you is: Do you sense that I am on track with all of this? Is there anything that jumps out at you that I’m veering off-track with?

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 spent a year working on my app but have nothing to show for it since it’s not ready. What should I do about my resume? Do I  1) leave the app off completely and have a gap there, 2) tell the truth about running out of money (which sounds like a lame excuse to me), 3) say I dropped the app because I realized it wasn’t going to work out, 4) forget changing jobs?

I know how to talk about the business. My concern is, there’s a difference between getting something off the ground and failing, and not even finishing the thing in the first place. It sounds like I don’t have the grit to get something done. Or that the idea was stupid and I’m not qualified to run their business because I’ll just come up with more stupid ideas.

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’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!

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.

I moved to Spain with my parents when I was 11.

I have severe ADHD and dyslexia.

I didn’t finish high-school.

I opened a bar when I was 22 years old, and lost a ridiculous amount of money before it closed a year later.

I started a software company with a friend of mine. I got tired of the friend and soon got tired of the company.

I started doing freelance work in “online marketing” very generally. Did some work with some local fashion boutiques to get them online. I learned a lot, but I felt I was being dishonest with my clients and not delivering the results they needed.

I decided I ought to go back to work, that I still lack a lot of experience and discipline and might be able to get this by working with more seasoned startupeers.

I joined a start-up that dealt with online fashion sales. I was fired after one month. They said they couldn’t afford me, and that I’d oversold myself.

I joined another start-up and got fired.

I find myself losing faith in myself, not sure what I’m doing wrong. I’ve often times when reading your blog feel like your brutal honesty and ability to cut through the bullshit is something that would help me out. I feel that I am very strong at some things (thinking outside the box, risk taking, sales, schmoozing) but really bad at other things (planning, “sticking with it”, networking with people I don’t automatically like).

In my heart what I want to do and be is an entrepreneur. I enjoy the thrill of creating something from nothing. But I don’t really have an “idea” now. My family urges me to keep looking for a job, even if it is one I’m not too excited about.

I feel like I’m at a crossroads, and that if I compromise now I’ll lose something intangible.

I haven’t felt this lost and directionless in probably at least a decade, and I think I’m at the point where I could benefit from your advice.

I have an idea for a yoga studio in LA, but I don’t have much cash. I was thinking of escorting on the side to pay my bills while doing this. I was wondering should I do this? I’ve always been open minded. Have you ever participated in the sex industry, or tempted to?

I’m about to found a business that gives users full control over their personal data. We just need some 200k to start.

We don’t have the funds to bridge the 4 months to the launch. If we don’t get the funding by the end of the year, we will have to work in our day jobs again. And watch as someone else puts something similar on
the market. Are we doing something wrong? How can we get funding?