It’s been 15 months since Blake Smith sold his first startup. In his newly found free time, the former Cladwell founder has taken some much-needed time off, consulted more than a hundred others on their early entrepreneurial journeys and helped raise more than $1 million in VC money for businesses that are not his own.
Now, the Ludlow resident has his eyes on what’s next.
Boilerplate.legal, which helps startups navigate all the documents and legalese they need to begin, recently publicly launched – and although it may undergo a name change soon, Smith sees plenty of potential with his second act.
Smith came up with the idea for Boilerplate shortly after he sold Cladwell, a platform that helps people select the best clothing to wear each day, to employee, Erin Flynn, and her husband, Colin, in August 2019. The company had had a crazy seven-year run. The following month, he posted an article on Medium titled, “We Sold Our Startup! 70 Lessons From 7 Years as a Venture-Backed Startup CEO,” lessons that he felt “he earned with blood.” At the end of that piece, Smith offered to chat with anyone looking for advice.
The response was strong. Smith took over 180 meetings over the past year with startups based all around the globe, which led to consultancy work and more.
The process was “really enjoyable,” he said. But he kept running into the same problem. Tons of early founders were making huge – and often very costly – legal errors, in an attempt to save money or go DIY. That opened the door for Boilerplate.
“It was really frustrating. (These founders) were all making the same mistakes I made literally a decade ago,” he said. “I just felt like it was this whole broken system.”
Smith said good legal representation is necessary for startup success. Boilerplate helps lower that hurdle by reducing the overall cost. The platform, he said, offers a simple and streamlined way to get a company set up for venture capital from the very beginning.
Boilerplate initially collaborated with downtown Cincinnati’s Thompson Hine and is now partnering with other law firms that provide its software. So far, its clients are largely U.S. “non-coastal” based, he said.
"All these docs that you really need to have in order, we automated,” he said. “We do Delaware incorporation, handing out all the shares to founders as well as to investors and advisors. We do employee IP transfer assignments, all the docs you really need to have in order.”
Smith has looped in his wife, Chandler; former Cladwell CFO Chris Ridenour; and Ridenour's wife, Nikki, in the business. The four of them are now bootstrapping the company. So far, the startup is cash-flow positive, and Smith said they’ve turned down about $1.8 million in venture funding.
That is something else he wants to do differently this time around. He said it’s one of the bigger lessons he’s learned. Had he had a tool like Boilerplate, he said Cladwell could have saved over $100,00 “fixing previous legal errors.”
“We dug a big hole at my last startup. I will say, the second time around, or the third or fourth time around, there’s a lot less ego and a lot more focus on the things that really matter – like revenue and actually getting customers and learning from those customers,” he said. “I feel like it’s been good progress so far.”
