Businesses Come and Go. I'm Always an Entrepreneur is the fifth post in a five-part series about my roots as an entrepreneur. The other parts are:
- One: Early Life Experiences with Leadership and Teamwork
- Two: From a Hobby to a Real Business
- Three: Scaling the Business, and Me
- Four: From Standing on Peaks to Battling Cancer
iContact eventually got acquired in February 2012. But it’d been a roller coaster of a year leading up to the exit—with competitors forcing up our customer acquisition cost and all the prep for an IPO, that we abandoned in favor of being purchased by a public company.
After all I’d been through in the previous few years, I probably should have taken a break at that point. But I’d already planted the seeds for a new company. In fact, I’d won a grant, which validated the new product with investors and pretty much committed us to take it to market. The goal was to launch that Spring.
BoostSuite came from the recognition that a lot of our customers at iContact didn’t know how to grow or get a list of email subscribers. We thought we’d write an algorithm that could analyze successful websites and then tell these small business owners what to put on their sites to drive email signups and new customers.
Different from iContact, we kept the team small and lean. We bootstrapped the business rather than raising outside funds. And we pivoted, a lot.
Our original algorithm told a lot of small businesses they needed a blog. But the owners didn’t have the time to create or source the content. So one iteration matched small businesses with similar interests or values so they could share blog content with each other. But while many customers loved the tool and loved to support each other, few paid to do it.
So after a year, we went looking for another way for these small businesses to share with each other. We landed on advertising. They could remarket to each other’s website visitors via online ads. We could charge them per ad, giving us a business model we could finally scale.
Data was key this time around. We didn’t let ourselves get too emotional. The numbers—which I personally updated every Monday for 4.5 years—told us whether it was working or not. And we adjusted our strategy as soon as we had enough data to prove something.
We did that one last time in 2017. Though we had 43,000 small businesses on the platform, it became obvious we needed larger customers to make the business model work. We’d done everything we could with our skill sets and interest. It was time for someone else to run our baby.
This story might make me sound more calm and calculating than I was building my previous businesses. But even with a smaller team, tighter belt, and a laser focus on numbers, I still struggled with the stress of building a new startup.
My highest highs and lowest lows came from the things individual customers said or didn’t say. I loved them for the great feedback they’d provide, and hated them for their irrational behavior. My mental state on any given day was often dictated by a positive review or a terrible phone call.
When we sold BoostSuite in September 2017, I decided to honor myself and my experience in two ways. I needed a break. And I needed to help other entrepreneurs.
After 20 years in entrepreneurship, I’m finally comfortable saying that stress comes with the job. Even though I learned to check my passion and ideas with knowledge, teams and facts, it’s still emotionally challenging to run a company. In fact, I’m pretty certain the struggle between passion and pain is universal among entrepreneurs.
I’ve learned (and am still learning) the only way to counterbalance the mania is to put healthy disciplines in place. My passion now is to share the ones that have worked for me and some of my peers. My goal is to meet with 100 entrepreneurs over the next 12 months, as well as publish a book about how entrepreneurs experience and manage stress. Stick with me here to see how that’s going.
I know I’ll start another company some day too.
But my hope is that time off, and time helping others, will offer the best prep for whatever’s next along my entrepreneurial journey.