Bootstrapping: How I went From Almost Broke to My First $8k Day in 1 Week

I don’t know how other people go from being broke to generating larger amounts of revenue, but I remember how I did

I remember my first $8k day.

It came only a few days after I was nearly broke. I don’t recall exactly how little money I had in my bank account, but I know that it was less than $600.

Here’s the full story and the reason I know this:

It was around New Year’s and 2015 was wrapping up and 2016 just beginning.

My son was about 8 or 9 months old and my daughter was about 3.5 years old.

We had been traveling around the country teaching pickleball clinics for a couple years prior, sending out email newsletters on a monthly basis, and had published our Amazon #1 bestselling book, Smart Pickleball a little more than a year earlier.

(Note: Although our book generated as much as $1600/month in revenue during its early months, the cost of living for a family of 4 in California meant we were still pretty close to broke. Just in case you thought finally being an author would immediately solve all your problems…

::newsflash::

It doesn’t! And also, having money doesn’t = financial security. Turns out managing money is an important skill–and one that I am better at than I used to be, but still learning.)

With the arrival of our son, I had tried to find solutions to keep my husband closer to home so I had launched the concept of a VIP intensive earlier in the year, and by this point, he had done 2 or 3 already and (typical of me) I was already looking at what we could do in the business NEXT to generate more income.

I had dreamed up the concept of a “bootcamp” where people would pay a VIP intensive-level investment ($1500) for coaching in groups of about 16 participants over a week or so. (Later we honed it down to about 3-4 days, but it started out as a 5-day workshop.)

Here is the graphic we used to promote it:

The view from the pool

It was perfect!

The only problem was…

… it cost $600 to rent for the week (which was ridiculously reasonable for a venue for an event like this) buuuuuut, as you know, that was $600 we didn’t have at the time…

We did, however, have an email list…

It was somewhere around 4,000 people.

So I begged the owner not to rent the place to anyone else and got busy finalizing the sales page and writing some emails.

I remember that my strategy was to send an email, then only send follow-up emails to the people who had clicked THAT email. Then only send a second follow-up to the people who clicked THAT email, and so on, for several emails. So the only people who got 7 emails that week were the ones who had clicked on the 6 prior ones. It’s an excellent targeting strategy that I continue to use to follow up with warm prospects without annoying colder ones.

Meanwhile, you can imagine the stress of sending an email saying “Hey, come to our event on Merritt Island” and meanwhile hoping that no one who registered for the event would go to Airbnb and find the quaint little pool house and book the venue where our event was supposed to happen!!!!

The (beat up but functional) tennis court

Within a few months, we had our first $20k month after doing our first webinar selling spots in more bootcamps!

Bootcamps are what brought our annual revenue up to about $160,000 that year, and are what have generated well over half a million in sales in the years since then.

And it all started with me dreaming up an idea for a bootcamp and bootstrapping my way forward on it as best I could–even when I didn’t have the money.

So do what you need to do to get by right now–in whatever situation you find yourself.

But don’t let your current reality limit what’s possible for the future.

It’s possible to be almost broke one day and generate thousands the next day.

Keep your eye on what you want to create and keep building the things that can change your situation in time.

It doesn’t always happen overnight. But sometimes it does. And often, one payment can be the start of 5 and then 10 and then 100 payments.

But it won’t happen if you give up now or and it probably won’t happen if you wait until everything is “in order” and the circumstances are just right.