Many people just know you as the awesome blogger and power woman behind Brazen Careerist, can you let us a little into the world of Miss Trunk?

I like to think that each of us working on the same stuff – figuring out who we are and what we want and how to get it. Those questions get progressively easier, but I’m not sure we ever get off the first one. That’s where I am, too.

Many young bloggers and Entrepreneurs say they draw inspiration from you, for example Monica O’Brien who is one of my favorite bloggers. Is there anyone you draw your own inspiration from?

Oh, I like Monica’s blog. She’s great at writing about gender. And, actually, I think that tons of bloggers are good at something. The trick is to find what you’re good at so you can inspire other people. Sometimes I find that watching someone figure out what they are good at is as inspiring as seeing someone be great.

Bloggers who I like:

Rebecca Thorman at Modite

Holly Hoffman – at WorkLoveLife

Lance, at Honey and Lance

Sam Davidson at Cool People Care

You put yourself out there on your blog posts and in a recent one, you explained why. Do you ever get people who give you bad feedback, send you emails criticizing you e.t.c? If you do, how do you deal with them personally?

I get emails criticizing me every day. I read them all. I like direct feedback, and sometimes, in person, people are hesitant to be direct. So I sort of like that people will just say anything on my blog — they spare no feelings there. Sometimes I think they are off base, and sometimes I think they’re right. In either case, I think about it. Because the way to get better is to be open to criticism.

A lot of young Gen Y entrepreneurs tend to get stuck after the idea is conceived and they’ve written their business plan. Can you tell us briefly how you started your first company? From the idea conception, through seeking funds, marketing and launching?

My first company was one I thought about for a year before I started. I knew I had intellectual property — math software from my investor’s company. I realized that I could buy math.com pretty cheaply, and then I looked around for what else could go on the site. I found out that Swarthmore College had a huge grant from the NSF to build math teaching tools, but Swarthmore had no idea what to do with them. So I put them on my site. And I decided that with that stuff, I needed to market to teachers. That’s how I figured out what my business was. It was incremental and I was very flexible. It’s important when you think of a business idea to know that a business is a bunch of very small, always changing ideas. It’s not one, big, stagnant idea.

You talk a lot about your constant quest for more funds for Brazen Careerist. Can you shed light on the effect of the sad state of the economy on securing funds for already established companies like Brazen Careerist? What about new start-ups run by novice entrepreneurs looking for seed funds?

There is plenty of money for companies that have a good idea. Really. The reason we ran into trouble is that we did not time everything well. But even when we were in really really bad shape, there was funding for us. You need to have all your ducks in a row to get funding. There is sort of a checklist of stuff you need. If you have that, you’ll get money. If you don’t have that, it is probably not the right time for you to get funding.

I have been told several times by many C.E.Os I have had the privilege of sitting down with that in business, it’s more about who you know than what you know. Do you agree?

Yes. Definitely. You need to be able to surround yourself with people who can fill in your own gaps in skills. I am constantly calling people for help and advice. I think young people don’t realize how often — each day! — very experienced people ask for help with an email or something like that. You need a network of people you can ask for help.

This is actually why Brazen Careerist works so well for entrepreneurs. Because for an entrepreneur their network is everything. And you need to be part of a community of people who can collaborate with you. That means you need to be talking with people to find out their ideas.

Also, entrepreneurs typically do not have useful resumes. They work for themselves and they change jobs a lot. Most people who are entrepreneurs also have been fired a few times: Not good for the Resume. Brazen Careerist’s ideas-based resume is perfect for the entrepreneur who is full of ideas and short on linear, corporate experience.

What are your views on the continuous rise and rise of social media as it pertains to company and personal branding?

My views? I don’t know. Is this controversial? It seems good for everyone. People telling more about themselves means that people can make better decisions about who to work with.

How did you start out as an entrepreneur? Most if not all entrepreneurs experience failure at some point, how did/do you deal with them? And how well do you handle rejection?

I keep trying. I have had a lot of failure in my life that I keep plugging away at so that it is not actually a failure. Most of how we approach life’s hardships is hard-wired — how optimistic we are. And you can test yourself to see the optimism you were born with. A friend once told me that entrepreneurs are optimists and VCs are pessimists.

The biggest thing about facing failure is to just get out of bed in the morning and try something else. Keep trying. Brazen Careerist ran out of money a few times. And we all just refused to give up.

What is the best advice you’ve ever got?

The more you know yourself the better you’ll be at getting what you want — in all aspects of life. You can know yourself faster by going to therapy.

When Penelope Trunk isn’t working, speaking e.t.c. what does she do for fun?

I think there is time in life to only do three things well. We spend a lot of our lives denying this, and trying to make it not true for us. But it’s true. So, like most people my age, I have time for work, kids and a significant other. That’s pretty much it. I mean, I work out a lot, but it’s not nearly as high a priority as the other stuff. The faster you can admit that you only have time to do three things well, the faster you can stop making yourself crazy trying to do more.

Thank you so much for taking time out of your busy schedule to do this! On a final note, give me and other gen Y entrepreneurs reading this one advice.

Be open to criticism. If someone thinks you can’t take it, you won’t get feedback, and you won’t grow.

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I first connected with Alain on Twitter some weeks back and his blogs (both french and english) are a constant source of ideas and advice for entrepreneurs of any age looking to build a start-up. Alain Theriault is based in Montreal and has been involved with teaching entrepreneurs and coaching start-up builders for many years. He holds an MBA from the University of Montreal and started the Entrepreneurship center there. With several years of Start-up coaching behind him, I thought many budding entrepreneurs like myself could learn from him, so I reached out with a few questions and he was kind enough to answer them for us.

P.s. If you are having problems with the streaming, try turning the HD off and it should work perfectly then.

Answering @Genystartup questions from Alain Theriault a.k.a Startupcoa on Vimeo.

Alain Theriault blogs here

Alain Theriault is on Twitter

Yu-kai’s Interview with Gen-Y Startup from Yu-kai Chou on Vimeo.

If you are really into looking for and following start-ups by Gen Y-ers, you probably would have heard of Viralogy. It’s a social media rank for blogs and the guys on that team have done a fantastic job so far. I first met the Yu-kai and his co-founder Jun Loayza on Twitter and have exchanged e-mails and so forth. Personally they are really good guys so I encourage you to reach out to them.

The point of these kind of interviews is to get the ideas of fellow gen y entrepreneurs already building a brand and making things happen. Learn what they did right, what their mistakes were and so forth. Hopefully these sort of interviews will help inspire many young entrepreneurs starting out.

Yu-kai is on Twitter

Yu-kai blogs at yukaichou.com

I wouldn’t consider myself a start-up professional, why would I? I have launched two companies that are still very young and growing and yes I only just started work last week on my biggest start-up so far. Still, this doesn’t make me a ’startup pro’. I will define a start-up professional as someone who has been in the business for a long time (atleast 15 years as far as I am concerned), started several ventures, been on several boards, dined and wined with the notable names in start-up and a mentor! These are people who have “been there and done that”, they have a whole wealth of knowledge to share.

I have never met Martin Zwilling but I have been reading his blog for a while now and I would be lying if I said the man hasn’t inspired me and taught me a few things. I was able to tweet with him and then email with him. Fortunately, I succeeded in getting an interview out of him. The point of this blog when I started out was the help young entrepreneurs like myself see the light, share my mistakes with them, how I fixed them and the lessons I have learned in the process. But I don’t have all the answers, I can’t single handedly direct you to start-up success, hence my interviews with well rounded, successful entrepreneurs like Martin.

1.) Hi Martin, thanks again for doing this. I know you founded and run Startup professionals which is doing great supplying tips constantly to people in the start-up biz, have you been involved in any other start-ups?

MZ: Yes, I’ve held operational positions in several startups, including VP Development for software, SVP Web Applications in another, CIO in a manufacturing startup. I’m now on the board of a medical services start-up and on the Advisory board of five other start-ups in early stage (software, green services, alternative energy, consulting, jobs website).

2.) How would you describe your experience with starting companies?

MZ: Startups are always a huge learning experience for me, and even more so for founders trying it for the first time. It takes perseverance,  adaptability, real hands-on work, and good problem solving skills. But the satisfaction of real progress and even small successes is tremendous.

3.) A lot of Gen Y guys are involved with most startups now, what is your take on this influx? is it a good thing in your opinion?

MZ: Definitely a good thing, due to their boundless energy and idealism. Yet I find many who haven’t learned to balance idealism and realism – everyone loves green, but most consumers won’t pay five times the price. Gen Y teamed with success boomers the first time around make a great balance, and provides credentials that investors love. The current recession is making Gen Y face business realities quickly, so it’s good for them in the long run.

4.) What is the most important lesson you’ve learned as a start-up guru?

MZ: I’ve learned that you can’t help everyone, especially people who won’t listen. Some people have such big egos, or are so naive that they believe they are bullet-proof. Rather than waste alot of their time and mine, I tell them early on that I can’t help them,  if the chemistry isn’t right. I’ve found I can accomplish more by coaching five founders who are willing to listen thoughtfully, versus one who wants to argue every step of the way, and then does his own thing anyway.

5.) What would you say are the features or characteristics that a successful start-up usually have compared to those that fail?

MZ: Every advisor and investor will probably agree on this one, that the difference is the quality and experience of the team. When I get a business plan, I look at the executive credentials and experience first, before I look at the product and the opportunity. A bad team will usually fail even with a good product, whereas a good team can often make a bad product work.

6.) What is the most imporatant advice you can give a new entrepreneur starting out now?

MZ: I recommend that you team the first time out with someone who has “been there and done that.” That could be a co-founder, or atleast an advisor/mentor who has domain knowledge, connections to other executives, and potential investors.

7.) Finally, what is the most effective way to market/promote a new venture in your opinion? (In a case where there isn’t a lot of money to be spent)

MZ: Social networks, like Twitter and Facebook, are an invaluable new tool, and don’t cost much. Equally valuable for Internet business sites is doing the basics of Search Engine Optimization (SEO), then a bit of Search Engine Marketing (SEM). My informal assessment is that only about a quarter of the start-ups really use thses resources today.

Martin Zwilling is on twitter (@StartupPro)