One of the reasons I moved from New York City to Madison, WI is that I knew I would start another company. I wasn’t sure what it would be, but I had already launched two startups, and I could feel another one coming. It’s a sort of itch I get when I have too many ideas piling up in my head: I think to myself, “One of these must be good for something.”

People ask me how I picked Wisconsin. The bottom line is that I wanted to be able to support my family and take the wild risks that come with having a startup. Supporting a family in NYC or Silicon Valley is insanely expensive especially for someone who has no cushion to fall back on during the months when funding is tight. (Which is a major reason you see lots of Silicon Valley startups from twentysomething men with no expenses and few startups from women with kids, and heated discussion on TechCrunch about salaries for founders who can’t make ends meet.)

So, here are some things to think about when you know you are going to do a startup, and you know you are going to move.

1. The first stage of a startup is constipation, which can happen anywhere.
The beginning of a company is slow and meandering. You have pretty much no idea what the company is or what you are doing with it, or if you even picked the right partner to do it with. You sit in a room and argue for a while. And you throw in the towel ten times. And then go get it and try again. You develop a bunch of revenue models that are either so lackluster that they are not worth your time, or so outstandingly huge that they are not believable.

During this time, it does not matter where you live. You are not hiring. You are not pitching your business because you don’t have a pitch. And you are probably not spending much money because you know the near future does not include a lot of money coming in. Read more

Brian Wiegand is a very low-profile guy who has sold three companies, most recently to Microsoft. He is big enough that TechCrunch writes about him as a good bet for anyone betting. But the bane of Brian's existence is that his exits have all been for under $50 million.

This is enough for him to have a private jet and be King of Madison (Wisconsin), but not enough for him to get a lot of respect in Silicon Valley. A quote from my advisory board member who lives in Silicon Valley: “For big VCs, $50 million is a rounding error.”

So Brian is not looking for people to mentor or boards to sit on because he is consumed with running his fourth company, Alice.com, which will compete with Wal-Mart and Target.

I do not tell Brian that I will have a hard time ever missing a trip to Target to shop at Alice because Target has such great clothes that are so cheap they are almost free.

Well, actually I did tell him that. And I told him a bunch of other stuff, because I decided that I need him as a mentor. Eventually, I got him to agree to be on the board of my company. Here's the process I took to convince him to help me. And these are good steps for anytime you have someone you'd like to ask to be your mentor: Read more

We finally locked up funding for my company. There are some catches, though, and one of them is that we can't use the funding to pay back debt.

This is a problem because our company has been out of money, pretty much, since November. We have revenue, but not enough to cover operating expenses. So we've all given up a portion of our salary for a while now. And we stopped paying rent. And we didn't pay freelancers, (which meant that for the past months, any time something broke, it was very high stakes because we couldn’t hire someone to fix it.)

The lack of money got so bad that one day I was driving to Chicago to meet an investor but the company credit card (which is really Ryan Healy's credit card) was declined. And I didn't have money for gas. So I had to drive back to the Brazen Careerist office and get money from Ryan Paugh, who is the only person in the company who has any sort of financial cushion in his life. But he only had $20, which is not enough to get to Chicago, so the investor had to meet me in Milwaukee. And buy me lunch.

The no-money thing has also been stressful at home. At first I cut back on stuff that was not a good idea. Like, cut back on the vet for our two new kittens, and then it turns out they are not that new, at least to the world, because one got the other pregnant. And now it's really expensive because we have to have a cat abortion. Read more

People ask me all the time, “What blogs do you read?” The answer is that I read different ones at different times. It’s a mood thing, I think. I could give you my favorite blogs for finding cool research, or my favorite blogs from my friends, or my favorite fashion blogs for when I don’t know how to wear a pair of shoes I love. But the list I’m going to do today is the list of blogs I read when I get frustrated that running a company is so hard.

ValleyWag
Oh, I love Owen Thomas. He has a knack for making anything in Silicon Valley look totally stupid. And he is so sharp, that when I am feeling totally stupid, he can actually make me believe that I’m not alone. Art Spiegelman elevated the comic book format by using it to talk about the Holocaust. Owen Thomas elevates the gossip rag format by using it to tell people how to run a business.

TechCrunch
You know what? I hate reading this blog because it’s like a frat party but they forgot the beer and the girls. Still, I know that part of feeling like a competent entrepreneur is knowing what’s going on in the community. Plus, who can begrudge Michael Arrington kudos for making the most boring topic in the world — big egos taking down big egos — funny and interesting? Read more

My company is out of money, which you are never supposed let happen. And definitely never supposed to confess to. Because then investors can give you any terms they want. Rape. Carnage. Pillage. Everything. And in our case, it’s coming from the angels who invested in our first round of funding, which means that the people who are supposed to be on our side are killing us.

So two days before Christmas, I am going nuts, trying to close a bridge financing from the angel investors who funded us initially. Which means that these guys are very rich, and traveling for Christmas, and totally not interested in being bothered with the minutia of our depleted finances.

I’m desperate. We’ve already skipped one payroll, and it’s hard to think of a worse time to do that than the week before Christmas.

When 70% of young people say they want to run their own business, they are probably not thinking they will fund their business themselves. Since they probably have no money. So they are looking at taking in investors. But I’m not sure that 70% of young people want to take in angel investors, because here’s what it looks like:

1. You are on the phone all the time.
Tuesday before Christmas: I am glued to my phone: Investors don’t work on a schedule. They are millionaires. They are trying to sail their boat in Bermuda but they live in Wisconsin which means they have to make ten connecting flights from snowbound airports, and my chances of catching them between flights are slim. So I spend my day waiting for someone to call in with another clever idea for taking more equity from the company and redistributing it to the investors.

2. You’re always sick, but not take-a-day-off-work sick
And I have pinkeye. It started on Monday, when 20/20 was in our office to do a story on salary. Yep. That’s right. The company that is not paying salaries right now is featured on 20/20 as the poster child for transparent salaries.

The camera is right in my face while I’m talking about how the only people who benefit from hidden salaries are managers who made hiring mistakes and don’t want to fix them. “Management should not hide behind their weaknesses,” I say. And then I say, “Do you have something in that camera that can fix my pink eye?” Read more

I can always tell when things are really falling apart for me by how many days in a row I wear the same outfit. Last week, I wore my I’m-a-successful-CEO outfit four days in a row. In case you need a visual, it is black all over with ruffle near the neck — a little bit girly and hides dirt well.

You will be interested to know that four days included one plane trip, meetings with six investors, and one date (I smelled the shirt right beforehand and it seemed okay. I didn’t think he’d be getting that close anyway.)

The last day was when I was really sure I was going to change outfits. I had an interview with Elizabeth Vargas for 20/20. I packed a huge suitcase full of everything that might look good on TV and I told myself that I’d figure out what to wear the morning of the interview. But the morning of the interview I was actually crying to my attorney about how complicated our second round of funding is becoming, and I told him that I was going to quit the company and get a job writing for a local newspaper. I really said that.

Forget the fact that local newspapers really are not hiring writers. Really. I think I was just saying it to him so he could understand how totally stressful it is raising money in this financial environment. Plus, it’s totally not cool to be admitting to such huge stress levels when you are the CEO. I mean, who wants to fund a company when the CEO is having a mental breakdown? But really, every CEO who is raising money right now is staying up all night worrying. And not telling anyone.

Well, except me. I am telling my attorney. And now you. Read more

It’s a season of joy, right? You are probably thinking that you can count on my blog posts to be a respite from seasonal joy. But still, I’m susceptible to peer pressure. Mostly because I think it’s an obligation of a friend to be sort of cheery. Because cheeriness is contagious. And on some level, I want to be your friend.

I have always thought a good mood is contagious, but now there’s more proof, in a study published last week in the British Medical Journal, (and in the Los Angeles Times, for those of us who like our research sliced in candy-sized bites.) The researchers followed 5000 people for decades and found that if you hang out with people who say they are happy then you are more likely to report that you are happy, too.

This might be a peer pressure thing, except it’s really a moot point. Because if you say you are happy, you get all the health benefits of being happy (image hosting). And, of course, those benefits are huge. It doesn’t really matter that it is irrational to be happy—you will mentally and physically in better shape if you go down that irrational path.

So even though I tend to choose rational discourse over cheery conversation, today we can have both. Here are three places where I found happiness and work intersecting.

Read more

I will be on a live call today with Guy Kawasaki and John Jantsch. You can sign up to be on the call here.

John is the force behind the Duct Tape Marketing blog, which is a great example of how to use a blog to grow a whole business. Today, his blog looks like an empire.

Guy Kawasaki has a very popular blog that I link to a lot, and he’s author of a bunch of books about entrepreneurship, one of which we are talking about on this call: Reality Check: The Irreverent Guide to Outsmarting, Outmanaging, and Outmarketing Your Competition.

Here’s what happens in every meeting I have with investors: They ask about my divorce.

Many people ask about my divorce. Usually it’s because the person cares about me. But with the investors, there is no pretense. They just want to know if Nino is going to get a large percentage of my stock in the settlement. The risk to them is that at some point, Nino would have so much stock in my company that it wouldn’t be worth my time to continue doing the company. The investors want to make sure they don’t get involved in a situation like this.

So I assure the investors it won’t happen, but honestly, I have to work hard to make that true.

For the most part, divorce is a divide-down-the-middle thing. For an entrepreneur with a venture backed start-up, the trick is finding the middle. Because there’s no perfect way to figure out the value of the company. I try to make the company look valuable enough that I can pay off our debt and support the kids, but not so valuable that Nino thinks it’s his ticket to divorce heaven.

My lawyer, Allan, sees it as his job to put the fear of God in me: If I cash out big and it turns out I mislead people in the divorce proceeding, then Nino can come after me for everything. “Just be honest” is what Allan tells me. For $400 an hour.

I refer him to the blog post where I say that lying on one’s resume is an art form and honesty is not black and white.

He tells me that divorce law is different from career advice.

I say I think the difference is that career advice has more than a one-time use.

Allan thinks this is not true because he thinks that one day I will divorce the farmer. He says, “Your farmer has land in the middle of nowhere. If you like farmers, I have a farmer for you. He owns the land at the end of [sworn to secrecy — major road in Wisconsin]. And he just sold a bunch.”

I remind Allan about how pissed off he was when I wrote a post about the last guy he set me up with.

Allan concurs: I am a nightmare to set up on a date.

This conversation takes place on the short walk to the building to meet Nino and his lawyer.

Allan asks me how I’m feeling about custody.

This is why I like Allan. He cares about me. He is thinking of the flurry of phone calls I made to him after I read that women who make a lot of money are losing custody to their husbands who make no money.

“Where did you read that?” Allan asked.

“In the London Mail.”

Allan said, “Forget it. This is Madison. Don’t worry about it. If you want to know what to worry about, worry about the company.”

I didn’t know if I should believe Allan. I didn’t know if I should worry. I have so many mentors who help me with my start-up: almost all of them are men, and all are extremely generous with their time and ideas. But none has experience losing custody as a mom.

So I asked Nino one day, when it was our three-year-old’s birthday and I was premenstrual and I forgot half of the goodie bags, “Do you think we parent equally or do you think you do more?”

He said, “I think you do way more than I do.”

I said, “Really?” I should have recorded it or something. But instead, I cried.

He said, “Could we just have a normal birthday party? No crying?”

Okay. So, flash forward, to the meeting with our lawyers. And in our ongoing quest to be normal, Nino and I sit in the room and we try to do niceties. But niceties are difficult for me and Nino. Not because we are not nice to each other, but because we are bad with small talk. I feel an affinity to him when both of us are befuddled during lawyer small talk about the weather and the Badgers.

We get down to business. Which is the business of figuring out how much my business is worth.

Nino’s lawyer, Steve, is worried that my business is stupid and I’ll never be able to pay off our debt. He says, “So much of the business is you. What if people start saying bad things about you?”

I say, “Haven’t you been reading my blog?”

Nino says, “No. I told him not to. I thought it would be too expensive.”

Steve says, “I’ve looked at it.”

I say, “Did you like it?”

Steve smiles. Or maybe he says yes. I can’t remember. But I remember getting the distinct feeling that he would let me use his name in my blog posts even though Allan told me to never use Steve’s name.

Me: Didn’t you see the comments? People tell me I’m an idiot all the time.

Steve: Well. I didn’t see that. But I saw the letter to the editor in the Wisconsin State Journal.

Allan: I have it right here.

Me: What? What is that? A scrapbook?

Allan: Yeah. Sort of. Here is where you were covered in the New York Times. Steve, did you see this?

Steve: Oh. What is this?

Me: Let me see the letter to the editor. Oh, this is just some over-educated person from Madison whining about how her graduate degree mattered.

[I look up. The lawyers are lost in the clips. Nino is shaking his head incredulously. Then everyone looks up.]

Me: I get hundreds of comments each week saying how stupid I am.

Steven: Really? I think I don’t understand how the business works. I thought you were an authority.

Me: It’s a fine line, stupidity and authority.

Nino: [giddy at the line of questioning] Oh, do you think so?

Steven: Can you explain the company again? How do you tell investors that you are going to make money from this thing?

Me: Well, I think the way I explained it last time probably didn’t work for you. So, I have an idea. Would you like me to give you the pitch I give to investors?

Steve: Sure.

Me: Should I stand? I usually stand.

Steve: Okay.

Me: Well, I usually have a PowerPoint presentation as well.

Allan: We can imagine it.

Allan is excited that I’m going to do the pitch. He thinks our best-case scenario is if Nino and his lawyer understand the company very clearly. Allan says they’ll leave all the stock to me if they see it’s in everyone’s best interest.

So it turns out that the key to a good divorce is good communication. Hilarious. For people who are not us.

I look over at Nino. He’s never even asked me what my company does. I am secretly happy to finally tell him. I think he should be more curious.

I do the pitch. At first I sort of tone it down, but then I get rolling. I realize that I don’t need the PowerPoint. I say, “We aggregate people who blog about their careers.” Then I talk about how great the bloggers on our network are: “Super-engaged employees that employers are looking for.” I toss around some financial estimates and explain, “We encourage employers to recruit by having a conversation in the blogosphere.”

Steve says he thinks that companies don’t know what blogs are.

Steve says he doesn’t see an employee shortage in Madison law firms.

These are not good observations. I worry that I have not explained things well.

But then Nino says, “That stuff is not going to be a problem. The problem is that the PR people won’t want to let everyone talk to bloggers.”

I say, “Nino’s right. That’s the weak link in the plan. He’s so smart. That’s why I married him.”

People are always asking me what our business model is for Brazen Careerist. Now that we have a network of 150 great bloggers, we are focusing on companies. A lot of companies come to us asking for access to the bloggers. Not surprisingly, companies want to recruit from the bloggers and their friends. But we think what the bloggers want is good conversation.

We think that offering someone a job without conversation is like walking up to a stranger in a bar and asking for sex. It doesn’t work. You need to establish some sort of rapport first. People want that from a job offer as well. People today want to work for a company that they feel some sort of connection to—a connection probably from branding and conversation.

So we want to help companies establish their brand as an employer, and create a conversation with people they’d like to hire, now or in the future. That’s our next step. And we have to sell the companies on this idea.

So we had one of my mentors, who is also an outstanding salesperson—Kathleen Kurke—give us a little coaching session on how to sell.

All of us at Brazen Careerist were in the training (there are eight employees now). And all of us were struck by how Kathleen’s advice applies to so much of life, not only to trying to get companies to engage the Brazen Careerist community. Here’s what Kathleen said:

1. Ask a good question.
You probably want a yes or no answer: “Are you gonna buy my product, yes or no?” But yes or no is short-term and opportunity limiting, because anything but a definite yes will be a showstopper. So ask instead a question like: What are the challenges you are facing?

This sort of open-ended question helps you to understand the challenges, solutions, or opportunities you are trying to capture. And the more you can align yourself with your client and their concerns, the more likely you will be to capture their business.

The better you get at asking these questions, the better answers you’ll get; and the best answers get you closer to the person who is accountable for solving the problem. And that’s the person who will be most likely to give you that yes answer that you are looking for.

2. Solve a problem.
People will buy stuff from you because you are solving a problem or capitalizing on an opportunity. In other words, people only buy stuff if it helps them make money or save money.

If you cannot trace your solution to either making money or saving money, then you have a problem.