May 3, 2013 · 5 minutes

I am not a humble person by nature. If you have read more than four of my articles, then you know that I have strong opinions and strong ideas.

But part of being an entrepreneur is knowing when to be humble.

And if you are a second-time entrepreneur, even one who had a great deal of success the first time around, then the rule applies doubly. A few observations thus far from the second go around:

1. If you are entering a new industry, then nobody really gives a crap about what you did last time. They probably haven’t heard of you.

This one is kind of painful, but it’s the reality.

I’m not entering a new industry per se. I am launching another content website. But the last one was for one audience (sports dudes), and the new site is for a totally different audience (young women).

And, so, I cannot go charging into this with the assumption that all of these women will fall over themselves to come join my editorial team.

In fact, most of them have had limited interaction with Bleacher Report, if any, and aren’t going to go onto Crunchbase to learn more. So, when I send them an unsolicited LinkedIn invite, I have to be humble.

It doesn’t matter that I just sold my company for hundreds of millions of dollars. I’m still going to act humble when requesting to interview a 24-year old woman who edits articles at Vanity Fair. I’m going to kindly request a chance to buy her coffee at a time and place that is convenient for her.

Because all of my prior success doesn’t mean jack shit in the eyes of some woman who recently graduated from Columbia Journalism and views the world through the prism of Conde Nast. That’s who I need to hire, and most people like that don’t read TechCrunch or PandoDaily.

Most women like that have spent their entire lives dreaming about being the next Anna Wintour or Maureen Dowd. To them, Times Square is Mount Olympus. And before I can convince them about my new startup’s merits, I have to break into a world where I have no connections, no past experience, and little credibility.

Two years from now, every young editor in New York will want to work for my company — that’s the ambition. But, as for today... I don’t mean shit.

2. Yeah, you can raise money with ease. That doesn’t mean that you should.

Over the course of the last three years, there were two industries that sprang up that I felt were saturated and unimaginative: Daily Deals and AdTech.

Why were there so many of them?

Well, part of my theory is that there were too many entrepreneurs who (a) raised a boatload of capital, (b) tried to do something that didn’t work, or (c) pivoted into an Ad Network or Daily Deals site.

There are innumerable examples, so it’s not worth calling them all out.

The worst thing that you can do, in my opinion, is go raise $12 million based upon your strong reputation, then realize — about $600,000 into the project — that it isn’t going to work.

In some cases, an entrepreneur will return the capital to investors and close up shop. But usually they “pivot” into something entirely different. Something entirely unoriginal. Like an Ad Network...

And so one of the keys to being an entrepreneur is to humbly raise less than you otherwise could.

Because, despite all of your past success, you still have to prove yourself once again. And if you can’t prove anything with a million dollars, then you are off to a lousy start. No, you don’t need to have the next Instagram after nine months and a million dollars spent. But you should at least have a viable product, a great team assembled, and something to show for your time and effort.

Not only that, but raising less money will put your back against the wall — and, believe me, you want your back against the wall! That is one of the few things that a second-time entrepreneur cannot replicate now matter how hard he or she tries. To reconstruct the fear and anxiety of a first time startup founder... that is a tall order. But you can easily put yourself into a crucible now and then. You can easily make yourself sweat. Watching your budget like a hawk feels great, even if $50,000 is no longer an awe-inspiring sum.

Being nobody again feels nice. And hopefully it is only temporary.

3. Stealth mode is hard. But it is necessary.

Stealth mode is an important part of a startup’s infancy. If you are not ready for the world to know about you, then you absolutely should keep your mouth shut.

This has been particularly hard for me, because I have a huge mouth, and I write two columns per week for a tech startup that a bunch of media and venture professionals read daily.

But just because you can get attention does not mean you should. In fact, too much attention can kill a startup before it is ready for primetime.

Whenever I see a startup with a star-studded launch party, I always ask myself this simple question: “Which startups in the past have succeeded after a star-studded launch party?”

When you think about debuts like Airtime, which was launched by some of the most successful and respected entrepreneurs in the world, and backed by some of the biggest name celebrities and investors, it gets you thinking. Maybe their launch could have been a more humble affair.

Associations are important, and I don’t want my new site to be associated with my old one...for better or worse. To say that is not to abandon the achievement that came before, but rather to embrace it. It’s the power of saying, “I love what I did last time, but I am big enough to do something new without feeling aimless.”

My last startup was a success, and this one will be better, even if that means launching quietly and growing slower. That is the goal. I want to have a soft launch in the near future, and I want to keep my mouth shut about it for a while.

Nothing I launch will be good enough in the first month or two. And if I make a big launch announcement and get everyone talking about my product, then I am doing that because my own hubris has exceeded my sincere desire to win. It’s an example of doing something because I can, not because I should.

So I look forward to launching my new site later this Summer, and I look forward to telling none of you about it.

[Image via oldgoldandblack]