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April 24, 2017
Recognizing Opportunities - Andy Cook, Co-Founder and CEO of Tettra

The best piece of advice Andy Cook, Co-Founder and CEO of Tettra, can give to young entrepreneurs is, “Don’t start a startup.”

Launching his own company never seemed to be a question in the mind of Cook. Growing up in Hanover, Massachusetts, Cook has had an entrepreneurial spirit since the age of 10 when he started his first paper route. Being raised by his mother, a teacher, and his father, the owner of a landscaping company, Cook grew up watching his father run a successful business for 35 years. As a child, Cook dabbled in his own endeavors, everything from hawking weekend newspapers outside his local Dunkin’ Donuts to collecting cans with his brother to recycle. Recognizing opportunity has always been one of his strengths.

Learning To Be a Founder

Anyone in the startup world will tell you that starting your own company is one of the most difficult, and stressful, things a person can do with their career. It’s even harder to start a business while you are still in college.

In 2010, while at UMass Amherst, Cook and his older brother Alex built an online rental marketplace called Rentabilities. The idea originated from an online booking system Alex was building for a local rental store owner. The site ended up generating tens of thousands of dollars worth of bookings in its first year, which opened the opportunistic eyes for the two brothers.

After looking at the market some more, they realized that renting anything from a bounce house to a lawn mower was a total pain. It was an underserved market which hadn’t been disrupted by an online model yet.

“We thought we could put it online, like a GrubHub for renting lots of different items,” said Cook.

It was a clever idea, but they needed more resources to execute on it. Luckily, they heard an ad for the first ever MassChallenge competition on the radio and decided to apply. It paid off, as they ended up winning $50,000 to help fund the business.

While at MassChallenge, Cook attended a talk which was given by Dharmesh Shah of HubSpot. He took notes from Shah’s discussion which he later published as a blog post outlining all the different startup lessons he shared. This ended up starting a relationship between the two of them and as they were raising additional capital, Shah participated in their seed round of funding.

Cook and his brother worked on the business for three years, but hit the wall with the Series A funding crunch. It was difficult to attract investors for the industry they were servicing and they eventually sold the business to HubSpot as an acqui-hire.

One of Cook’s biggest takeaways from running Rentabilities, and advice he would give to other founders, is to focus on solving problems that you can relate to. Ultimately, he wasn’t the site’s demographic, as he didn’t have the need to rent anything.

“It was hard to get into the head of the user and grind it out when I couldn't really even use our own product,” said Cook. “When the going gets hard, and trust me it will, solving your own problem really helps because if everything else implodes, at least you’re making your own life slightly better.”

Don’t Start A Startup… Unless…

When a second time entrepreneur tells me his best advice to young founders is, “Don’t start a startup,” a hypocritical eyebrow raises…until he explains the idea behind solving your own problems.

“Only start a company if the idea you want to solve is so compelling to you personally that you have to make it a reality,” says Cook. Not only is this great advice from Cook, but it is also echoed by Dustin Moskovitch (Facebook co-founder) in a recent presentation at Stanford’s Startup School.

Tettra Team Photo
Tettra Team Photo

Cook is practicing what he’s preaching with his latest company, Tettra, which is creating a wiki for Slack teams. Cook and Nelson Joyce, his co-founder, discovered a pain point while trying to keep their small team at HubSpot on the same page. They were interested in using an online wiki. But to their surprise, a solution didn’t exist… at least something that was simple and designed for small teams.

Again, recognizing an opportunity, both Cook and Joyce left HubSpot to build out their own wiki solution. They had to iterate quickly on the product based on some early feedback from teams testing the product. They realized a stand-alone application wasn’t going to have the right level of user adoption. Instead, it would be better if their wiki was integrated with another commonly used product that already had widespread adoption.

The timing worked out, as it was right around the same time that Slack launched their platform for external developers. They rebuilt 100% of their entire product on Slack and started getting an impressive number of signups, which validated the market and opportunity. They went on to raise just shy of $1M in funding from Dharmesh Shah, David Cancel, Mike Volpe, BOSS Syndicate, and a who’s who list of investors.

“First time founders have it tough, especially if you are looking to raise capital, because you’re learning so much in terms of building a company from scratch, all while trying to figure out how to make something people want. They must build out their professional network and also create a successful company (and ultimately organization) in extremely difficult circumstances,” says Cook. “If I could do it over again I would have worked for a startup that was scaling right out of school to learn and build relationships, then I would have gone out to start my first company.”

Two other pieces of advice from Cook is to find great mentors and stay scrappy. Great rules to live by for any first time founder.

When discussing his entrepreneurial journey so far, Cook remains very humble and realizes he still has so much to learn.

“I've found in life that the more I learn,” says Cook. “The more I realize what I don't know and have so much more to learn.”


Necco Ceresani is a contributor to VentureFizz.  Follow him on Twitter: @Necco_C.

Hat tip to the Tech in Boston podcast interview with Andy Cook which was used as part of our research.  Listen to the full podcast here.