Buying a $5M AI Calendar Assistant Business for Calendly: Is It Worth It?

Have you ever wondered what it would be like to own a business that makes scheduling meetings super easy? Well, that's exactly what this $5 million deal is about. Bill D'Alessandro and Heather Endresen discussed an intriguing business opportunity on the latest episode of Acquisitions Anonymous. They looked at a company that built an AI-powered calendar assistant, similar to Calendly.

The listing:

We found this deal on Acquire but it's unlisted now.

What's the Deal?

The business in question has created an AI assistant designed to streamline scheduling. Imagine you’re trying to book a meeting, and instead of the usual back-and-forth emails, this AI assistant does all the work for you. Sounds amazing, right? This technology isn't just convenient; it has the potential to save a lot of time and hassle.

Key Takeaways

1. Price Tag: The business is up for grabs at $5 million. It’s a hefty price, but the technology behind it is quite promising.
2. Revenue and Profit: The company is generating around $1 million in annual revenue with a $400,000 EBITDA (Earnings Before Interest, Taxes, Depreciation, and Amortization).
3. Recent Changes: There was a significant price hike from $10 to $39 per user, which has caused some churn but also increased revenue.

The Challenges

One major point Bill and Heather discussed is the competition. In the world of AI and scheduling, it's easy for new players to pop up and offer similar services at lower prices. This makes it hard to stay ahead unless you have strong distribution and marketing strategies.

Additionally, moving up the market to B2B (Business-to-Business) deals can be a good strategy. Big companies like Verizon or Bank of America may want to use this technology at scale, and these deals are harder for competitors to undercut.

Financing the Deal

Heather explains that buying this business with a loan might not be easy. A 10-year SBA (Small Business Administration) loan is usually the go-to for such purchases, but it only covers about 3.75 times the earnings. This means buyers would need to come up with significant equity to cover the rest.

Is It a Good Buy?

Bill and Heather agree that while the technology is cool, the $5 million price tag might be steep, especially if you're relying on a loan. However, for the right buyer, someone with a strong understanding of the software and a vision for its future, this could be a great opportunity.

The Lender’s Perspective

It's important not to assume that getting a loan means it's a good deal. Sometimes, lenders may not fully understand the nuances of the industry. This is why having knowledgeable investors and advisors around you is crucial.

Final Thoughts

Buying a $5M AI calendar assistant business like this one could be a fantastic opportunity for the right person. But it's essential to weigh the competition, understand the financial implications, and ensure you have a solid plan for growing the business. If you're interested in SaaS deals or thinking about investing in tech businesses, this episode of Acquisitions Anonymous is definitely worth a listen!

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Thanks to this episode's sponsor:

Acquisition Lab and their team have been longtime supporters of the pod.

Acquisition Lab exists to help people buy a business and navigate all the complexities of the process, as well as provide a trusted framework, tools, and resources to support you from search to close.

If you are serious about buying a business, check out acquisitionlab.com or email the Lab's director Chelsea Wood, chelsea@buythenbuild.com and mention us ;) 

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