It’s been quite a while since we’ve heard from GladlyDo, the site that matches local students in need of money with people looking to have odd jobs done. But the startup has been making strides since the last time we spoke in January.
When I caught up with GladlyDo’s CEO Woody Klemmer, he shared how much the company has been expanding recently and how there’s no end to that in sight. In fact, he’s deemed 2016 “the Year of the Grow.”
Although all of the updates were impressive, I was more struck by what Klemmer had to say about the life of a young CEO at an early-stage startup. He was inspiringly earnest.
What's going on with GladlyDo
This fall, GladlyDo physically entered the Boston startup world, leaving their Needham dwellings behind to set up shop in Fort Point. With now more than 400 college kids finding small jobs through the site, Klemmer and his team decided to make the move.
Office space isn’t the only thing getting revamped for GladlyDo. As it continues to grow, the site itself and its features are in need of an update, which is exactly what the team is working on. To up security and make for an even more positive, comfortable experience, GladlyDo is adding profile features, such as pictures and more sophisticated review capabilities.
At the same time, to assure people posting on the site are being helped with the highest quality workers available, the startup will be integrating filters. Soon, doers will be able to receive posts pertaining only to certain types of work, areas of town or even people. Hopefully, this feature will allow doers to find jobs that are a better fit for them.
Stumbling into startup-dom
During my conversation with Klemmer, our talking points seemed to deviate from GladlyDo updates, and he started to share what it’s like to be heading up a scrappy startup trying to establish itself. Basically, Klemmer said that everyday is a whirlwind of joy, frustration and confusion - and he wouldn’t have it any way.
“I never wanted to do this,” Klemmer started to say. “I was never that person who had this amazing idea that I had to create. I was almost talked into it. But I’m so glad I’m doing what I’m doing. I can’t imagine not doing it.”
“I had no idea what I was doing,” he continued. “I googled ‘how to start a legal business’ and went through steps one through 10. A year later, I’d look back and say, ‘Holy shit, I’m a lot further than I thought I would be.’ It’s now another year later, and I can’t believe what else we’ve accomplished. If I keep doing that, I can’t imagine where we’ll be in five years.”
A frank account of entrepreneur life
Social decorum dictates that money is a no-go topic of conversation. But Klemmer went there. He’s not selling out, especially while he’s still young and has few responsibilities - an enviable attitude in some regards.
“I have no mortgage, no kids to support, no pressure. If this just turns into a big flaming pile of crap, at least I’ll have a cool story.”
“I could be working in finance like I thought I was going to do, or be in sales making a ton of money,” explained Klemmer.
“I’m only 25,” he went on. “I have no mortgage, no kids to support, no pressure. If this just turns into a big flaming pile of crap, at least I’ll have a cool story.”
GladlyDo is still making progress, and Klemmer confessed he’s not living a ritzy lifestyle. However, when you hear how, at one point, he was paying office rent by cleaning bathrooms, moving to the new digs on Congress Street is a big step in the right direction. And he maintains there’s more to come.
“It’s not glitz and glamour - at least not yet,” Klemmer told me. “I know we’ll make it eventually.”
“Everyday, I’m on the bus, which is how I get to work,” he added. “There are all these 20-somethings from Southie, and I think about how we’re all around same age, but not one of these kids is happier to go to work than I am.”
Image via Woody Klemmer.
