I almost sold Late Checkout for 8 figures…

The story of how it went down

New episode of my podcast is now live! I chatted with Josh Dorkin to learn how he went from knowing nothing about real estate and community to building BiggerPockets.com the top real estate community to 2m members.

You can listen on Spotify, Apple and watch on YouTube

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Late Checkout is my thing.

It’s my main focus. It’s the agency/studio I wake up every day and look to push forward, bringing products that foster community to as many people as possible. We’ve worked with some of the biggest and most exciting companies you can think of. 

…and I almost sold it.

To Twitter.

This is at least a year and a half ago — before Elon bought the platform and kept it in the news cycle, before Spaces, before the Views feature and whatever is next.

I received an email from a high-ranking Twitter executive looking to make the connection. Actually, let me rephrase to clarify how direct they were: Twitter was looking to make an acquisition.

To paraphrase: 

-> “Hey Greg, 

We’ve heard about a lot of the work you’re doing with Late Checkout, how you’re partnering with different companies and making their products more social and community based.  We believe if Twitter was more community-based, good things would happen.

From what we’ve heard, we think you guys are probably one of the best at doing it.

We want to have a conversation regarding a potential acquisition. Oh, and we’re serious about this and won’t waste your time. We have buy-in from the leadership team on specifically this deal with your company”

Twitter is one of my favorite platforms. I use it all the time, and I can’t lie — seeing this email come across my screen gave me the goosebumps and that warm and fuzzy feeling.

I hopped on a call with members of Twitter’s executive team. They were looking for Late Checkout to propose what Twitter would look like with more community features. My team and I worked through a quick two-day hackathon and came up with a potential solution:

Twitter Nests. Here’s the cover slide of the 12 slide deck where we outlined a more fun, more community-centric Twitter.

A few days later, Twitter got back to us with a healthy eight-figure offer. I guess they liked the designs.

This was life-changing money. We’ve never taken any outside capital, so we own 100% of our business. But throughout this process, I realized I constantly was asking myself questions to build a framework for “How do you decide when to sell?”

Do I wanna work for this person? 

Do I wanna work for this company?

Do I believe in this company long term?

Does that extra X amount of dollars really change my life?

If given the opportunity, would I be excited to run this company?

The questions became increasingly specific. Twitter is based in San Francisco — would I enjoy spending a lot of time there? Am I willing to travel to their offices across the world? I love my life in Miami.

Soon, I became self-reflective about the present-day work.

Am I stable in my current role?

Am I having fun?

Do I get excited to work every day?

Think about it — why do we do the things we do? Oftentimes it’s routine. We do the tasks we’re used to doing, not because we particularly enjoy them. As my friend Antonio Neves says, we are living on auto-pilot.

I turned down Twitter’s offer.

I came to the conclusion that building Late Checkout is the most fun I’d ever had in my career, and the most creative I’d ever been in my life. It was difficult to turn down that number, but it taught me what I wanted.

And what I (still) want is Late Checkout.

The question for you is… are you doing what you want to be doing?

Be well,

Greg Isenberg

BTW - A couple ways to get involved in Late Checkout

1. We set up a FREE community called Late Checkout Land. It’s for people who want to become idea generation machines with community based products.

   Applications are here. People are loving it

2. We just launched a design subscription called Dispatch. Imagine unlimited designs for apps, websites, icons, decks, you name it. All for $4995/month, way cheaper than a designer in NYC. Check Dispatch here, it’s blowing up. Spots limited.

   

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