Smash Notes
Bootstrapping a B2C Startup to +$20k/Month with Buster Benson
Buster Benson (@buster) is the founder of 750 Words, a $5/mo journaling tool. He kept it alive for more than a decade while working at Twitter, Slack, Patreon and running and shutting down Health Month, a startup leveraging social gamification to get its users healthy. Learn about his impressive entrepreneurial journey, how he went from liberal arts to…
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Notes
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Buster Benson has recently published his first book which goes all about "productive disagreement" and conflict resolution. He has collected a series of researches in the field and has made them more approachable and easier to understand, particularly through drawings.
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Buster has gone through Amazon, Twitter, Slack and Patreon throughout the previous decade while working on side-projects like 750 Words.
Prior to getting into tech, he had also started some startups.
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Buster Benson says Amazon would hire liberal-arts people and train them as engineers. A coworker asked if he knew Perl. He did not. He bought a Perl book and spent a weekend cramming, copying scripts from the internet and building forms. That was enough to make him think he could do the job. He emailed an engineering team about an opening and heard nothing, so he told HR they were not answering. They let him interview even though the role was closed. He said he could learn and that he cared, and they hired him. The site he walked into was old: Perl, plus C and makefiles that generated the HTML.
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Many founders identify clicks on their lives when they realize they will become founders. That happened to Buster while working at Amazon and feeling disillusioned of doing the same things over and over again.
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Buster Benson does not offer a technique. He offers a sequence. After about five years at Amazon he started 43 Things with coworkers from Amazon, in a group called Robot Co-op. The mission was to make something interesting on the internet and then try to make money from it. Tagging, early SEO, and blogging were all still new, so they invented the working rules too. One he remembers is four days a week at ten hours a day. The ideas, as he tells it, came from that freedom to try a product and a way of working together. They were not a list he had stored up while he was still inside Amazon.
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Buster shares the story behind his project Health Month, an online game that helped people motivate one another to lose weight, exercise or achieve other goals.
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Health Lab came from the merge between Buster's project "Health Month" and Y Combinator-funded Contagion Health.
A few years later, it would shut down after running out of money.
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Buster Benson says he is a fan of Peloton and that the company has mastered the pieces of game design that still matter. He does not call it gamification anymore. He likes the count of days a rider has shown up, the sense of being in a class while at home, the shout-outs, and the high-fives with people on the bike at the same time. A rider can compete with herself or with friends, even on a different schedule. Asked whether social, game-like products still have room, he points at that mix. It is the lesson he took out of Health Month, used by a company that is not his.
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In 2009, Buster started 750 Words as a side project. It currently makes +$25,000/month.
He shares how it all started and the journey towards where the platform is today.
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The lesson Buster Benson carried from Habit Labs to 750 Words is to stay small. He does not want to raise money, hire a cofounder, or scale because a startup is supposed to scale. The mistakes he regrets began when he listened to venture investors. A round of a couple of hundred thousand dollars let strangers in, and then the company was supposed to install a business person as chief executive, hire marketers, and follow a plan that pulled him off the product. He does not call that model always wrong. He says it is no longer for him. 750 Words stays independent so the product does not have to please an investor.
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The hardest thing about starting a company is the fact that you are going to be highly motivated to ignore the problems. Fake it till you make it, move fast, break things, that kind of thinking gives permission to ignore the obvious problems, and it's never worked out well for Buster. He say the problems are eventually going to become unavoidable and they will destroy you. Instead, it is important to understand the simplest path that can take your business to being sustainable.
Start by figuring out why someone would use your product, why would they pay for it, why is it better than alternatives, what would make them switch...etc. Be realistic about your assumptions and expectations. Look for the thing you don't want to see.
p.s. Buster has just finished a book called Why Are We Yelling? . It's a good read!
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