Thread by @iamwillcannon

My SaaS just broke $8 Million in sales this year,

And I'm incredibly grateful to be in this position.

But it wasn't always this way...

Here’s the 6 (and a half) business I've failed at:

#1 Real estate

I didn't have any money and I wanted to build a real estate empire at the time.

At one point,

I slept in my real estate office.

I was leasing an office (800 sq feet) for my own business and lived in it because I didn't have enough money for an apartment.

I slept there and woke up and showered in a bucket.

(there was no shower)

Yes, I had a small bucket in a little bathroom.

This was just me and my girlfriend at the time (now my wife).

We lived in our office until we hustled enough to finally buy an apartment.

#2 Foreclosed on four properties during the 2008 Real Estate Crash

I did really well in real estate and bought a lot of properties...

Then the huge crash came.

All my properties lost half their value overnight.

There were four properties and I had to foreclose on each one.

#3 Filed bankruptcy

Soon after the market crash,

My real estate income went to nothing.

I still had all my expenses every single month...

And on top of that, I had all those properties upside down.

I was in crazy debt.

It was a choice of figuring out or filing out bankruptcy and make it go away...

So I filed for bankruptcy.

#4 Ran out of business

My real estate and mortgage company went out of business completely.

We were crushing it with my little empire of real estate (mortgage, escrow, loan processing) and overnight,

Our income went from 6 figures to basically negative.

#5 Merchant services company

This was my way to get recurring revenue after my failed real estate business.

I thought:

"Hey, I sell a business - they get their merchant credit card processing machine. Every time they run a transaction, I get a small % of that - it's recurring"

It turns out at the time I wasn't able to acquire customers profitably.

We lost a lot of money and it eventually failed.

#6 Insurance company

I still wanted recurring revenue...

So I got my insurance license.

My wife did too.

We took all these tests, courses, etc

I thought I could acquire customers and make bank...

But it didn't work.

This was like finding customers B2C (not B2B),

Which I'm horrible at.

Dealing with consumers was a nightmare business.

#6.5 Spent $300k building a SaaS that failed

This was after Uplead but before Signaturely.

I started a SaaS in a different industry than the one I'm in right now.

It was a very complex business - we spent a lot of money until I got burned out.

It's on pause right now.

I love starting new businesses,

But I have a limited amount of time.

(haven’t given up on this one though!)

Now I have two very successful businesses:

1. UpLead (B2B Prospecting, valued at around $75 Million)
2. Signaturely (E-Signatures)

But it wasn't always that way.

Sometimes you just need to keep trying until something sticks.

I'm now documenting my journey on Twitter,

And sharing ALL the lessons I've learned about SaaS, cold email, customer acquisition, marketing, client work, and more.

I have tons of threads coming very soon - follow me if you don't want to miss 'em!

-Will

I share threads weekly on SaaS, Startups, Cold Email and Entrepreneurship

Follow me if you'd like to see more of those ;)