(Part 1) Events that changed my business

Hey Reader,

Here's a question I get a lot:

“If you had to start over again,
how would you grow your business?”

OK, OK, I get it. Not every business owner starts out with a huge email list or a profitable idea. But before you come down too hard on yourself, remember, I originally tried to develop an e-book on HEALTH INSURANCE! ZzZzzzzZZz...

I’ve been there and I can share what I actually did as a struggling, newbie, clueless entrepreneur.

Years ago, I’d moved to San Francisco so I could hang out with friends more. I would hit Tequila Tuesday on Union Street, then go to work at my startup the next morning. IWT was just something I did on the side.

The good news was I’d built up a few followers. People liked what I was writing because I told it to them straight. Whenever I’d post something, I’d get a bunch of comments.

The bad news was — I didn't really understand how to turn my audience into real revenue.

I had tried some ads and affiliate offers. Those brought in a little bit of money, but not a ton. I've always been very picky about who I promoted on my site and I didn't want to turn my site into a clickfarm (which is how those businesses work).

I did some consulting and made decent money but I knew that wouldn't scale as high as I wanted it to. I wanted more freedom and more impact. That's why I started IWT in the first place.

So what next?

I had heard about online products and dabbled with an e-book. I sold a few — more than I thought — which showed me that people would buy stuff online … and even ignore the most outlandish names on earth (“Ramit’s 2007 Guide to Kicking Ass").

That $4.95 e-book gave me an idea: I was already writing about saving money … what if I put together my best savings advice into a product? Would people buy that?

I decided to try, so I created a product: Scrooge Strategy.

Now, I knew it was a good product because I’d used the tips myself. 

Here's how it worked:

• It would be a subscription product at $8/month
• It would be 1 email/week
• The big promise was that each month, you’d save far more than the cost of the program (I estimated that over the course of a year, you’d save 50x - 100x the cost of the product) 

But how was I supposed to launch this product? I’d previously sold my e-book via a single blog post. That was fine as a baby step, but I didn’t think that strategy would work for a bigger product like this — I needed something bigger to get their attention.

This proved to be a lot tougher than I’d expected. Suddenly, I was worried about...

• Sending too many emails and having people unsubscribe
• Being too “sales-y” (people started to email me and accuse me of only doing this to make money)
• Doing all this work and ending up with crickets — no sales, no response, nothing

("OMG, this was supposed to be a fun side project..." was what I kept thinking.)

Here's what I decided: I was going to go all-in. I decided to throw everything I had into it. I built a “Save $1,000 in 30 Days” challenge — a full MONTH-LONG series of free tips. At the end, that's when I would tell them about my new product.

This strategy had a lot of upsides:

• Lots of great new material every day — including some of my best tips
• Readers could test the material out for themselves and see that it works
• No sleazy sales tricks. Just helpful content

And a few downsides:

• Uh, 30 days of new content to produce is a lot. Especially on top of everything else … and getting the new product ready to launch … and my day job … and actually having time to have a social life (or sleep)
• What if people hated the series … or got bored? What was I going to do? Keep sharing or stop halfway?
• I didn't know how to add sales webinars or upsells or calendar reminders or any of the other fancy tricks some other businesses used. I just had email and blog posts.

OK, now it's your turn to be the CEO…

What would you have done?

You have an audience that's listening. You have a good product that will help them. You have a little bit of time, but not enough. You need to get people's attention and get them excited to buy. Is this the best way to do it?

What would you do?

Reply to this email and tell me what you’d do (and most importantly, WHY). I read every response.

Tomorrow, I’ll tell you what I did and how it turned out.