When Mylestone founder and CEO Dave Balter stepped aside to focus more on his new cryptocurrency investing service last November, it turns out the Boston startup only lasted for another month before calling it quits.
Balter confirmed to BostInno on Wednesday that Mylestone shut down in December. Drew Condon, who was promoted to CEO when Balter stepped aside, has been back working at HubSpot as director of product design since January, according to his LinkedIn profile.
Founded in 2015 under the name Mylestoned, the Boston startup began as an online memorial service that had big ambitions to change the way we remember those who have died. While the startup began as a chatbot, Balter told BostInno in a 2016 interview that he had a “50-year-plan for this company,” which included plans for a location-based service that could send a push notification if you walk past a house a family member grew up in. There were even potential applications for virtual and augmented reality.
The startup then ditched the “d” from its name and pivoted to become a personal memory bank for Amazon Alexa devices, broadening the original scope to include memories of everyone, both alive and dead. Then, sometime in 2017, the company pivoted again to creating custom photo books, according to Xconomy. (Mylestone had acquired a photo app in 2016.)
Mylestone had raised a total of $4.5 million from investors, including Founder Collective, Converge Venture Partners, and Boston Seed Capital, where Balter is a venture partner.
In an email to BostInno, Balter gave an overview of what led to Mylestone’s demise, and some of it is tied to Balter’s decision to start cryptocurrency investing service Flipside Crypto, which was born from Balter’s desire to find a way to properly value the hundreds of digital currencies flooding the market and making it easy to acquire and store them.
“Success would require an incredible focus on user growth and monetization and likely additional rounds of financing.”
“I spent a lot of time mulling the two operations,” Balter said.
Balter, who had started Flipside with his own capital, said Mylestone had been closing in on a product market fit and that “customers were loving our product.” But the problem for him as CEO was that the company had shifted from B2B to a consumer-oriented business, an area in which Balter didn’t have as much experience. The company had also not generated revenue at this point, Balter told Xconomy last November.
“Success would require an incredible focus on user growth and monetization and likely additional rounds of financing,” Balter said.
Flipside, on the other hand, “had the wind at its back,” and Balter’s team was “being pulled into the business at a ridiculous pace.” “It was incredibly fun, we were solving a real customer need and there was immediate revenue,” Balter added.
After much consideration, Balter said it became clear that Flipside had a higher likelihood of success, leading him to step down as CEO for Mylestone and become chairman in November while making Flipside his full-time endeavor. With that decision, Balter said he returned $2 million of the capital Mylestone raised back to investors while also giving them the ability to invest in Flipside in the event of a future funding round at a fair rate.
“A company must be wound around the CEOs specific skill. If it isn’t, no matter the hustle, no matter the willingness, drive, focus, creativity — it will always be less than enough,” Balter had written in a November 2017 post explaining why he was stepping down.
When Balter decided to step down, Drew Condon, Mylestone’s head of product, told Balter that he was interested in moving the company forward. But after Condon took on the role of CEO, things didn’t last for much longer.
“They were making ridiculously fast and substantial progress morphing the business into a standalone operation – but ultimately, for a whole variety of personal and professional reasons, they made the decision to not move forward,” Balter said.
Condon didn’t respond to a request for comment Friday afternoon.
This is far from Balter’s first rodeo. Before he started Mylestone and Flipside, Balter had founded two startups, BzzAgent and Smarter, which were later acquired by dunnhumby and Pluralsight, respectively. Balter also co-founded Intelligent.ly, a leadership program for emerging tech leaders in Boston that is shutting down this year.
“Every company is different, every team is different and every market is different; success comes from awareness that you can’t treat them all the same, and from a willingness to make tough choices to build where the greatest opportunities lie,” Balter said.