Taking the Leap: Cauzly.com Founder Jonah Lupton on the Secrets to Becoming a Successful Entrepreneur

Josh Z by

Long before his 30th birthday, Jonah Lupton was living the kind of life many young professionals dream of.

becoming an entrepreneur

His career had already included stops at prestigious financial firms like Morgan Stanley and Smith Barney, and he was making good money for a young professional in his early 20s.

But Lupton, who at his professional peak worked for a private trust company in Boston, was also miserable. He didn’t love his work in the financial services industry and was tired of working for someone else.

So, in April of 2011, Lupton made a decision that many would consider crazy. He walked into his boss’s office, placed a resignation letter on his desk, and officially walked away from a lucrative corporate career. All without a definitive backup plan in place (except, of course, knowing that he wanted to become an entrepreneur).

Lupton understands that his decision was risky, but it’s not one that he regrets. Before leaving his full-time job in 2011, Lupton had founded three Internet startups, and his newest venture, Cauzly.com, a social fundraising website for nonprofits, went live earlier this month. He is also an advisor and consultant for numerous Boston area organizations, all of which Lupton says teach him new things every day and hone his vision for Cauzly.com.

Lupton recently sat down with OpenView to discuss the challenging lifestyle of a serial entrepreneur, the lessons his own experience can teach aspiring startup founders, and where he hopes to take Cauzly.com in the future.

Did you have an entrepreneurial epiphany one day and just decide to quit your job on the spot, or have you always been an entrepreneur at heart?

I think that entrepreneurial fire has always been there, even if it wasn’t always obvious to me.

For example, when I worked at Smith Barney, I helped one of my clients uncover a $400,000 insurance policy that she didn’t know existed. That netted me a pretty significant bonus, which a lot of people would have used to buy a nice car or a house. I went to a local radio station in Cape Cod and bought six months of radio ads to grow my personal book of business. I wanted to reinvest in myself and my future rather than in a Porsche or a flashy new condo.

About two months before I quit my job, the light bulb went off and I knew I wanted to found a startup full-time. I didn’t have a specific idea in mind yet, let alone a formal business plan, but I knew that everything about being an entrepreneur — even the potentially negative stuff like having to surrender yourself to the business — excited me.

A little more than a year after quitting your job, do you have any regrets? And are there any specific byproducts of becoming an entrepreneur that you haven’t enjoyed?

I’m not married, I don’t have any kids, and my social life is basically nonexistent. Outside of that, entrepreneurship is a blast!

All kidding aside, I have no regrets because I’m happy and I feel like I’ve finally found my calling. That being said, becoming an entrepreneur isn’t for everyone. It’s not this glamorous lifestyle where you sit on a beach with a laptop and squeeze work in between surfing sessions.

Entrepreneurs have to be willing to put their own financial stability on the line, stop taking vacations, and work their tails off. If aspiring startup founders believe they can do that, then they might have a chance. If, however, startup founders aren’t willing to risk their financial future and sacrifice their personal lives for their business, then they should probably try to find another line of work.

It’s easy to look at super successful entrepreneurs and assume that their paths to wealth and success were relatively easy. In reality, most of those entrepreneurs are workaholics who sacrificed many years of fun and freedom, and worked relentlessly to see their vision through. They never knew for certain that their companies would survive, but that never stopped them. Their businesses could have crashed and burned like so many startups do, and today we wouldn’t be talking about them as successful entrepreneurs.

What’s the most important piece of advice that you would give young entrepreneurs or aspiring startup founders?

I think you have to be willing to learn something new every day and adapt to that information. In some circumstances, that might mean accepting information that indicates your inevitable failure. The old adage “fail fast” holds a lot of truth. Ultimately, the faster you admit defeat, the quicker you can pick yourself up and either start a new business or pivot your current one in a direction that will be more lucrative.

I also believe that it’s critical to surround yourself with good advisors who have been entrepreneurs before. I’ve been doing this for four years now, but I recognize that I still have plenty left to learn. I send emails or texts every day asking for advice and I constantly collect feedback, not all of which is positive.

The bottom line is that if you’re going to do a startup, then you have to be willing to expose yourself a bit and accept everything that comes your way. So, I always tell young entrepreneurs that they need to get a minimum viable product out there, collect feedback, listen to criticism, and iterate from there. By doing that, you’ll know what your customers really want and you can go build it for them.

What inspired you to create Cauzly.com, and what do you hope it will become?

When I was in the financial services industry, I worked with a lot of people in the nonprofit space. For the most part, they were great people doing great things, but they were so far behind the eight ball when it came to modern marketing and social media. I recognized that there was an opportunity to help that industry innovate, so I founded Cauzly.com in January. My goal is to help nonprofits more efficiently execute a task that’s so critical to their business — fundraising.

Entrepreneurship, Web 2.0, social media, and nonprofits are all passions of mine. By combining all of them into one business, I get to do something that I love and learn a lot from the experience at the same time.


Jonah LuptonJonah Lupton is an entrepreneur, advisor, investor, blogger, speaker, sports lover, philanthropist, and fitness junkie. In addition to being the founder and CEO of Cauzly.com, Lupton is the founder and president of the NextGen Leaders Council and the Inspired Futures Foundation, and an advisor to 10 other startups. He is an avid social media user and you can find him on Facebook and Twitter.