What startup life is really like

Brazen Careerist is my third startup. People ask me all the time why I gave up my position as CEO. If you knew what startup life was really like, you would ask me why I was CEO for as long as I was.

When I started building the brand of Brazen Careerist around the year 2000, I talked about ideas like job hopping as a way to build a solid career, and I warned that generation Y’s entry into the workforce would be a total shock to employers. I was labeled a heretic and a moron.

But pretty quickly, people started thinking I was right. And I started making $15,000 a speech to discuss these ideas.

The intoxication of being on a trend, and knowing how to monetize it and being excited about being right, that’s what makes someone do a startup. So I picked up two partners, I launched Brazen Careerist, and quickly, Mashable called us the number-one social networking site for Gen Y. We were on a roll.

We raised money. We launched products, we pivoted 20 times. We were due to raise more money right after the markets crashed. So of course we couldn’t raise money. And of course I did what all startup founders do when they run out of money: I had a shit fit. And then I had a nervous breakdown.

But the thing is, in a startup, everything moves at warp speed, even a nervous breakdown. So I recovered fast, convinced investors to put in more money. And we kept going. Read more

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Finance tips for the self-employed

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This is probably what you think self-employed looks like:

I’m at an amusement park with my kids, in the middle of the week, and I’m on a conference call while I watch my son try to get on a ride.

Being self-employed looks so nice at an amusement park. The self-employed are always free to go on a vacation. They pick up their friends at the airport in the middle of the day, they show up for poker night because they can stay out late, and they can plan their wedding without having to pretend they are working.

Close up, though, most self-employed people are completely stressed about money.

That money part is what I hate about being self-employed. Anyone who says they don’t love a steady paycheck is lying. A paycheck is so nice. It’s reliable like a friend, it makes you safe, it gives you a way to organize your life.

Here’s how I deal with the worrying: Read more

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Techniques for looking normal

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Last week was a board meeting for my company, Brazen Careerist. I used to hate the board meetings because there is so much to prepare beforehand, and if everything is not going great, then you have to really face that.

1. Hide your feelings if they are going to be trouble for someone.
I am still a major shareholder in my company, but I do not work at the company day to day. I would like to say that my neediness issues and fear of abandonment do not follow me to my workplace, but in fact, they are huge there. And I spend a lot of time worrying whether people listen to my opinions because they care or because it’s easier to listen than to try to get me to shut up.

When the board meeting rolls around, I get nervous. I don’t know if I should go or not.

I like to go because I like knowing what’s going on. Well, and of course, I like giving my opinion. I also like hanging out with the board. I really like Ryan Healy now that I don’t have to work with him. And everyone on my board is someone who did a huge amount for me at one of the (many) very tough times in my life. (Like this time.) So I just really like everyone. Read more

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Do this for your career right now: Start a company and sell it for a dollar.

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This is the column I wrote for BNET. Usually I keep my best ideas for my blog, but after I posted this on BNET I thought: Hold it! This is a great idea! Everyone should be doing this to make their career great. So here’s the post.

If you want to make yourself stand out as a top candidate for almost any job, try this approach: start a company and then sell it for nothing. This is a lot easier to do than you may realize, especially if you think of entrepreneurship as a career-building tool— instead of a bank-account building tool.

Are you thinking this sell-for-a-dollar thing is a waste of time and effort?

It’s not. Here are five reasons why it's a smart career move: Read more

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On Sunday my son sold his pig

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When the pig litters came in January, the Farmer helped my son pick out pigs for his 4H project. They picked four, because you never know, really, how a pig will grow. So you start with four and pick two after a few months.

My son woke up every morning and fed his pigs, for six months. And after three months, he walked with the pigs, around in a circle, twice a day, to train the pig for the show.

There is huge variety in the amount of help parents give their kids in these projects. Some kids’ parents buy show pigs from out of state and the kids take very little care of them until the fair. Some kids do everything themselves.

I think it’s a lot like an allowance for a city kid. Each family manages the potential pitfalls of an allowance themselves. Read more

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You can reframe anything

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Melissa is driving through Darlington trying to avoid the police. If they see me they'll arrest me, and we know they know my car. I put the front seat back all the way so I'm out of view. I keep my seatbelt on because in case they see us, I don't want to be breaking any extra laws.

I have to start this story when I was getting a divorce. People told me the cleanest, easiest divorces are when there are two good lawyers. So I asked around for the two best lawyers in Madison. They knew each other, of course. And negotiations went smoothly, except for my lawyer quitting first when I started blogging about the divorce and then when I agreed to talk about the divorce with the New York Times.

The police are not actually chasing us. But we feel like we're on the run. I told my lawyer — not my divorce lawyer but my new lawyer, who deals with about-to-be-arrested types — that the police have been to my house three times to arrest me. The Farmer is so stressed he's not even coming back from the hayfield for lunch. The lawyer says, “You'll have to stay away from the house til I can get the papers signed by a judge.”

I was thinking of staying at Jeanenne's house for a few days but I feel bad asking her to harbor a fugitive. So Melissa and I are on our way to Madison.

As we pass the turnoff for our house I worry that we don't have our computers. Read more

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This is the new, reliable me

Welcome to the world-famous board meeting for Brazen Careerist.

For those of you who have not been to a board meeting since I had a miscarriage in the board meeting, let me tell you, this one will not be so interesting. At least at a biological level.

What's interesting, maybe, is that there is always tension in the board meeting because who knows what I'll do next?

But I am trying to be on good behavior. I am trying to be a more reliable person. Not so much of a wild card. I just read this study that the five most career-limiting habits of smart people are:

1. Unreliable

2. “It’s not my job”

3. Procrastination

4. Resistance to change

5. Negative attitude

I think we each must know what ours is, because I knew right away that mine is unreliability. I have been sort of telling myself that I am so clever, bright, and witty that unreliable doesn't matter. But it does. I feel bad that so many people are reliably there for me and I'm a wild card. So I decide I'm starting to be reliable today. I am going to be dependable and well behaved in the meeting.

I can't sit still. Some people have to rock back and forth or use a squeeze thing. I have to think about something else and write it.

We review how our ideas at Brazen Careerist were too early and now the world is catching up. I think about how I am too far ahead about goats. Goat will be the new beef. Forget cheese. The melting pot of America will be filled with goat meat. Read more

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What it looks like to start a new business

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Since Melissa is living on the farm full time, she has farm jobs. Her job is to get my younger son to take care of his lambs. Technically raising and selling two lambs is his business. He wanted to earn money like his brother, and his eggs selling is no longer high enough stakes for him.

But if the lambs are a small business, Melissa is a co-founder.

Imagine my five-year-old with his two front teeth missing and his blond curls still flat from the last night’s bath.

Imagine Melissa sitting next to him. Each with dark black lamb in their lap, each lamb the size of a kitten and each is drinking out of a bottle.

Cute, right?

But here’s what it is, really. My son is swinging a bat, threatening every living thing with accidental decapitation as he walks sort of to the lamb house and sort of not, as I shout, “Get your butt to those lambs!” Read more

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I’m starting a new company!

In case you don't remember, I really got exhausted doing Brazen Careerist. The pressure was insane and it made me nearly lose my mind multiple times. Now Ryan Healy is running the company in DC, and I sort of miss the startup life — sort of like women endure labor and then a year later they are pregnant again.

So I have been sort of bored and lost all winter, trying to think of what to do next. And then, one night when I was visiting my neighbor, her son propped himself up in his TV-watching chair and told me that he wants me to help him do a company this summer. For his summer job.

I said, “OK, but what do you want to do?”

He said he wants to pave driveways. Like, put tar on them.

So I asked, “How will you get customers?”

“I don't know. That's what I need help with.”

“I think you should start out with a list of ways you can get customers and then see which way is conducive to starting a business. So, if you could get customers for dancing on your head, then you should dance on your head rather than pave driveways. The customers are the hard part.”

“So what should I do then?” Read more

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How to know if you’re an entrepreneur

Here’s an interview of me in Inc. magazine. John Warrilow did the interview. The topic was how to know if you’re an entrepreneur. I basically said that you know you’re an entrepreneur if you are crazy, in a manic way, and you are willing to risk the health of your family and have no chance of a stable income, ever.

Then John sent his book to me. It’s called Built to Sell. It turns out that John did a startup and he sold it, and his book is, basically, how to be so smart about doing a startup that you are aiming for a reasonable, not-pie-in-the-sky exit from day one.

I spend a lot of time talking about how startup life is completely crazy, and the founders are crazy for choosing it. But in fact, the lower-stakes, lower-risk entrepreneurship, where, instead of having investors, you use your own time and energy to make money on the side while you are doing other things – that’s a great way to structure a life.

Ramit Sethi has great advice on how to do this. Its called Earn $1K On the Side. And now I bet a ton of you are going to sign up for his program, and I should have negotiated beforehand to get a cut of whatever he earns from this post. But I am stuck thinking about insanely risky businesses with high reward and so I forget to do things like earn $300 when it’s just sitting there. Read more

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