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April 4, 2017

Taking Risks with Jonah Lopin, Crayon's Co-Founder and CEO

​Whether it’s dropping a successful career to travel across the world or take a chance on a risky new startup, Jonah Lopin is one CEO who is not averse to risk.

Jonah Lopin, co-founder and CEO of Crayon

Son of an electrical engineer and teacher, self-admitted nerd and now co-founder & CEO of Boston-based startup Crayon, Lopin is not what you might expect after reading his LinkedIn profile. Using words like flirt and play when talking about his first experiences with computers at the age of six, it’s not so hard to see why Lopin found his place amongst the software elite from a young age. After leaving his job at Deloitte to volunteer with UNICEF in Beijing, and then finally receiving his MBA from MIT,  Lopin found himself not taking a job in international investments, but risking everything as the 6th employee at a startup with unbounded potential.  

The HubSpot School of Hard Knocks

No matter what education or background you come from, taking a “senior” position at an early stage startup is extremely risky. But for Lopin, padding a resume with middle management jobs was never in the cards. His personal business philosophy comes in two forms, “I want to build something big that changes the world,” and “I was to use my time on planet earth not to avoid risk but to create new things.” It’s this philosophy that lead a young Lopin to taking a job, at one-third the salary other companies were offering, and building an enterprise that would change the software world forever.

“I think any good executive can learn as she goes and make up for inexperience with tenacity, good coaching, luck, etc. Relevant experience just makes things easier,” says Jonah Lopin in an interview earlier this week. His experience just so happens to be ‘the HubSpot School of Hard Knocks’, as I like to refer to it. Six years of hard-won lessons building a crazy vision from the ground up has given Lopin three business lessons he takes everywhere he goes.

1. Every new hire should be better than the average of the people already at your company.  If you can’t keep that up, your average declines over time, by definition.

2. Many mistakes will be forgiven as long as revenue grows. We got lots of things wrong in the early HubSpot days, but one thing we got right, really right, was we cracked the code on a repeatable sales & marketing process that enabled us to grow quickly.

3. Whenever possible, use data to make decisions.

It was these three lessons that set up the foundation for Crayon, Lopins latest software adventure. Crayon solves the problem of prioritizing, organizing and analyzing new data coming from your competitors.

The Makings of a Great CEO

If experience makes life easier, it’s hiring that makes Lopin successful. “The number one thing is that I’m a good recruiter,” Lopin says. “I’ve hired over a hundred really good people in my career and the team I’ve recruited for Crayon is top notch. It’s not easy recruiting top talent to an early stage company. It’s all about being able to explain your vision. The other part of it is having a good instinct and a process for finding the stars. If the 5th person you hire isn’t the right person, 20 percent of your company sucks for at least a year.”

At the end of the day, starting and running a successful company isn’t about being a great recruiter or having the most experience. The CEO of a company must possess an innate drive to create their own vision. Jonah Lopin is the type of person who succeeds because he, even after being a founding member at HubSpot and creating the immense visions of Dharmesh Shah and Brian Halligan, decided to put his career on the line again to build his own vision. This, at the end of the day, is what separates so many from so few.


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