James Ashford on Regretting Selling a 12-Employee Company for 8 Figures

November 29, 2024 |  

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How Mike Winnet Sold His E-learning Company for Around 4-Times Revenue

In 2015 Mike Winnet started U.K.-based Learning Heroes after recognizing that most e-learning programs were long and boring. Winnet saw an opportunity to transform the industry by creating short, engaging, animated training courses. 

 

Winnet started by trying to sell his courses to job seekers, but when his efforts failed, he pivoted to selling to companies. Instead of a few hundred dollars a year from job seekers, selling to companies meant he was getting a few thousand dollars a year.

 

 

 

 

 

 

 

Why Candy Banners Sold for a Mint

In 2014 Tim Grassin founded Candy Banners, which designs ads that show up along the top, bottom, and sides of a website.

Grassin built a remote team in the Philippines to minimize his costs. Hiring inexpensive developers allowed Grassin to charge lower rates to agency owners, resulting in rapid growth.

The business had grown to over seven figures in revenue in 2020 when Grassin received an acquisition offer from one of his clients, Native Touch. The offer valued Candy Banners at around five times EBITDA, and the deal closed in 2021.

 

 

 

 

 

 

 

A Regrettable Deal

In 2013 South African entrepreneur Jason Bagley started Firing Squad, a lead generation company specializing in cold emails.

In 2020 Firing Squad signed an agreement to be acquired by Southern Web and was later rebranded to SiteCare.

The deal was something Bagley would later come to regret.

 

 

 

 

 

 

 

Bootstrapping to a $200 Million Exit

In 2012 Patrick Campbell founded ProfitWell to help SaaS companies increase revenue and reduce churn by managing their data in a single place.

After bootstrapping the business to 8-figures, Campbell decided it was time to raise money. While he was seeking a financial investor, Paddle approached him with an acquisition offer. Soon after, in 2022, Campbell sold ProfitWell to Paddle for over $200 million.

 

 

 

 

 

 

 

 

One Company, Two 8-Figure Exits

Ed Buckley started Peerfit, which allows companies to offer fitness classes as part of their employee benefits package. The company grew to more than 150 employees before receiving an acquisition offer for almost $100 million from a major fitness brand widely reported to be Peloton. Buckley retained some of the IP, which, in a strange twist, he was able to sell in another eight-figure exit months later.

 

 

 

 

 

 

 

 

Selling Your Business vs. Getting Acquired

In 2012, Ryan Coon started Rentalutions, a platform to help landlords manage and communicate with their tenants more effectively.

The business showed steady growth, but Coon wasn’t satisfied.

Five years in, Coon rebranded the company to Avail and focused his marketing to target DIY landlords with under ten rental units to manage. The changes proved successful as Coon grew the business to around $7 million in revenue before selling to Realtor.com in 2020 for approximately five times revenue.

 

 

 

 

 

 

 

 

The Surprising Reason Ryan Kulp Sold Fomo

In 2016, Ryan Kulp launched Fomo because he saw marketers using aggressive popups on their websites.

Kulp reasoned that if he could show other people were shopping and interacting with a site, it would give new visitors confidence in the company.

Fomo allows businesses to show off real-time customer interactions (purchases, opt-ins, even pageviews) with a line of code the company installs on their site.

 

 

 

 

 

 

 

 

How to Avoid Seller’s Remorse

Rory Fatt began his entrepreneurial journey running marketing seminars for restauranteurs. After several owners approached Fatt to do their marketing for them, he decided to launch Royalty Rewards in 2005.

The business was a multimedia marketing platform that helped small businesses market their products and services by rewarding loyal customers. The company took off, hitting just over $2 million in revenue in its first year.

Inspired to achieve financial freedom, Fatt began to explore selling his company. In 2022, he accepted an offer from Schianti Partners that would set his family up for life.

 

 

 

 

 

 

 

 

Selling Your Side Hustle

Jeremy Nagel started his entrepreneurial career teaching clients how to get the most out of Zoho, a popular CRM platform. Nagel began cultivating a small following on YouTube by sharing his advice for Zoho enthusiasts.

Given his status in their ecosystem, Zoho approached Nagel about creating an SMS plug-in for their application to allow users to text their clients while using Zoho. Nagel developed the application while keeping his day job. Despite only dedicating one or two days a week to its growth, the feature quickly became one of the top five applications in the Zoho marketplace.

 

 

 

 

 

 

 

 

How to Get Your Business to Run Without You

When Jodie Cook started her social media agency, nothing happened without her involvement.

Desperate to free herself up from the minutia of running her company, Cook started to systematize her business with Standard Operating Procedures (SOPs). After a few missteps, Cook mastered the art of delegation.

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