Highlights from #imakealiving San Francisco and Looking Ahead to NYC!

FreshBooks is on the road! Last month, we hosted #imakealiving in San Francisco. Next up: New York City!

With great risk comes great reward — and for small business owners everywhere, this couldn’t ring truer! Plenty of heart, soul and labor goes into the creation and day-to-day of a small business. And guess what? FreshBooks is here for you every step of that journey.

Last month, we hosted another great #imakealiving event in San Francisco, CA. Here’s how it all went down!

Highlights from #imakealiving San Francisco

Our amazing panel included Zack Chen (Co-founder of Impressions Holdings), Wendy Colson (Founder and CEO of Boobie Bar) and Jonathan Johnson (Founder of DirectGov Source and PPEKits.com). The audience and our panelists were welcomed by FreshBooks’ Events Manager Paco Arizmendi and the event was moderated by special guest, Elaine Pofeldt.


Elaine is a veteran journalist who has contributed to publications such as Fortune, Money, Inc., Entrepreneur, Fast Company and Forbes. She recently published The Million Dollar, One-Person Business, which explores the rise of the one-person/non-employee business and the strategies taken to successfully do it alone, from automation to outsourcing.

To kick things off, Elaine asked each panelist to share what was going on in their life before they started their million dollar, one-person business.

Wendy Colson explains how the idea for Boobie Bar was born at a free community breastfeeding support group. She was constantly receiving questions on how women can increase their breastmilk supply, especially when they are on the go and have little time to eat.

“I was stumped! They say there are 400 new protein bars that hit the market every year, but there wasn’t one yet for a mom, who had just had a baby abd needed extra iron, fiber and if she was lactating (like 80% of the woman in this country attempt to do) that supports lactation.”

Jonathan, founder of DirectGov Source and PPEKits.com had a bit of a different experience:

“I started the company in 2007. I was in the mortgage industry at the time and it was at the time of the biggest recessions we’ve seen in a long time. I was at the office and I came in one day and my staff [were] gone — left or got fired. I was at the cross-roads where I didn’t want to work for someone else.”

Elaine then steered the conversation toward whether or not the panel experienced an “aha moment” when starting their business or coming up with their business idea.

Zack immediately replied that he definitely did not.

“It was just sort of an evolution over time of trying things, as many things as I could, when I didn’t know what was the right answer. And over time I figured out that this idea that we tried this time, it seems to have legs.”

Wendy responded as well, stating: “It helps to have an idea that hasn’t been done in the marketplace and that you can scale, so it’s affordable for you to do or you take something that’s in the marketplace and you make it better.”

To wrap-up the discussion, Elaine asked the panelists to look back with 20/20 hindsight and share if there were any experiences that helped them get to a higher revenue level.

Jonathan reminisced on his early days of starting up.

“I approached [my company] as a job. I got every morning just as if I was going to work because I was learning — learning the processes, learning to invoice, learning purchase orders. I was learning the language of the business and learning the language of the market at that particular time. I’m very thankful now because when there are situations where I don’t have my assistant or I have to do it myself, I know every aspect of my business from a financial aspect, a production aspect, a sales aspect and a marketing aspect.”

Zack added that automation really allowed him to focus on building his business instead of being stuck in the weeds.

“For me the change in my business occurred when we really took automation on. What we ended up doing was figuring out what was taking the most time out of our day and basically automating it. How can we make this so we don’t have to do as much?”

Looking Ahead to #imakealiving NYC

For the 7th city on our #imakealiving tour, we’ll be heading back to the east coast to NYC! Each and every #imakealiving event helps to facilitate and inspire connections between small business owners — and we’re honored to be a part of it all. Ready to get the conversation going, NYC? We can’t wait to meet you!

Event: #imakealiving Powered by FreshBooks
When: Wednesday, October 24th, 6:30 PM – 10:00 PM EDT
Where: 501 Union – 501 Union Street, Brooklyn, New York 11231, United States
Details: The #imakealiving events bring together an eclectic group of small business owners for a lively, candid and often hilarious conversation. Part small business boot camp, part group therapy with a special keynote at the end, you’ll leave feeling inspired and motivated. Plus, you’ll get lots of actionable insights to take you and your business to the next level. #imakealiving will take place in the evening, which includes a networking social following the main event with drinks and food for everyone attending! We are delighted to announce that we have also partnered with The Babysitting Company to provide free on-site care for any parent that wants to use this service.
Cost: Free — seeing you thrive is all the payment we need
Moderator: Elaine Pofeldt
Panelists: Stacy Berman, Rachel Charlupski, Iris Scott

RSVP to the #imakealiving NYC here

about the author

Content Marketing Manager, FreshBooks Lisa is passionate about small business success, having managed funding programs for hundreds of start-ups and entrepreneurs while working with a Canadian startup accelerator. She is presently Content Marketing Manager at FreshBooks and in her spare time, can be found tending to her plant babies.