Highlights from #imakealiving NYC and Looking Ahead to Austin and Portland!

FreshBooks is on the road! Last month, we hosted #imakealiving in NYC. Next up we have two stops: Austin, Texas and Portland, Oregon!

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 #imakealiving event in New York City. Here’s how it all went down!

Highlights from #imakealiving NYC

We had one of our largest panels yet, which included a mix of both product and service-based small businesses:

  • Stacy Berman – NYC fitness icon and Founder of The System
  • Rachel Charlupski – Founder and CEO of The Babysitting Company
  • Steve Ferreira – CEO of Ocean Audit
  • Kelly Lester – Founder of EasyLunchboxes
  • Angie and Colin Raja – Founders of RIMSports
  • Iris Scott – oil finger painter

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 the panel, to share what compelled them to make the leap to entrepreneurship.

Colin Raja, co-founder of RIMSports, explained how the structure of the standard, corporate job didn’t really work for him. He eventually convinced his wife, Angie to join him in his entrepreneurial pursuit. But that decision wasn’t easy for Angie, who was successfully working in a marketing role, making over six figures a year. Her advice:

“Ask yourself, are you really secure in your job? What does that mean to you. It took me a long time to overcome that.”

Angie later added: “If you are desiring to do something other than corporate America, you need to go for it and you need to be smart about it. You need to plan and make your exit after that.”

Elaine then steered the conversation toward what the panelists did to differentiate themselves from other players in their industry.

Finger-painter, Iris Scott explained that her pricing strategy was a big differentiator for her when she started selling her paintings on Facebook in 2009. She priced very low around $60-$80 a piece, but slowly raised her prices over time.

“The key is to raise the prices so slowly that nobody notices you are raising the prices. And if a painting isn’t selling, discount it aggressively behind closed doors and announce it as sold.”

Iris added this great tidbit of advice for other fellow artists: “Inventory is not your friend. It’s just not sustainable. You’d be much better off selling ten $100 paintings and creating a feeding frenzy online than having one $1,000 painting getting sold and nine in inventory forever.”


Steve Ferreira, CEO of Ocean Audit and two-time entrepreneur, added that he differentiated his business by specializing in ocean transportation, which is a very unique area in freight-bill auditing. With over 30,000 hours of experience in this niche, he understands this vertical better than anyone.

“My manta is that if you are going to start a B2B business, use your skill sets that you have learned within your companies. Do an experiment within your company and save your company some money. Use that exercise as a test case.”

Founder of The Babysitting Company, Rachel Charlupski found that her network of 2,500 babysitters was a huge factor in keeping her business organized. It meant Rachel could stay out of the weeds and focus on scaling her business.

“We hired people that were already in our network. We have many babysitters that are good with technology; babysitters that are good with marketing and Instagram; babysitters that are great with answering phones or client relations. So we use our own network to help us out in the office.”


To wrap-up the evening, Elaine asked the panelists to look back at their “dog food moment” and share a time that they really struggled.

Kelly Lester of EasyLunchboxes shared a time when the factory making her product in China had to halt production due to electricity issues:

“[Even though] you work so hard as an entrepreneur and you do everything right and everything you could do, [there are still] forces that are outside of your control.”

Fitness icon, Stacey Berman added that she keeps moving forward by acknowledging that failure is going to happen:

“When you have your own business, you’re doing a lot of stuff, so you might be a success here and a failure there. I think one of the things that really got me to stay motivated was to build in those setbacks.”

Looking Ahead to #imakealiving Austin and Portland

We’ll be making two stops this November on our #imakealiving tour: Austin, Texas and Portland, Oregon. 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? We can’t wait to meet you!

Austin, Texas

Event: #imakealiving Powered by FreshBooks

When: Wednesday, November 14, 6:30 PM – 10:00 PM CST
Where: Fair Market, 1100 E 5th Street, Austin, Texas 78702, 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!

Cost: Free — seeing you thrive is all the payment we need
Moderator: Elaine Pofeldt
Panelists: Ben and Camille Arneberg, Hal Elrod, Benedict Dohmen, Santiago Nestares Lampo and Allen Walton

RSVP to the #imakealiving Austin here

Portland, Oregon

Event: #imakealiving Powered by FreshBooks
When: Wednesday, November 14, 6:00 PM – 10:00 PM PST
Where: The Leftbank Annex, 101 North Weidler Street, Portland, OR, 97227, United States
Details: A keynote speaker will give education, insights and inspiration to small business owners, entrepreneurs and creatives. After the keynote, the event opens up to the audience for the opportunity to ask the speaker questions directly related to their business. FreshBooks is offering food, drinks, swag, free headshots and networking with like-minded individuals. A networking social will be closing the event.

Cost: Free — seeing you thrive is all the payment we need
Keynote Speaker: Emma McIlroy

RSVP to the #imakealiving PDX here

about the author

Senior Content Marketing Manager, FreshBooks Lisa is passionate about small business success, having managed funding programs for hundreds of Canadian start-ups and entrepreneurs. She is presently Senior Content Marketing Manager at FreshBooks.