Q. Kindly give our readers an introduction to your business. Please include what your business is all about, in which city you are located and if you have offices in multiple locations/ cities.

ANSWER: ProAssisting provides remote executive assistant services to business owners, entrepreneurs, C-suite executives, non-executive board members and known personalities. We are a fully remote company with clients and remote executive assistants across the United States.

Q. Kindly give us a brief description about yourself (it should include your brief educational or entrepreneurial background and list some of your major achievements).

ANSWER:I got my degree from Bentley University located in Waltham, MA and worked in music, film, advertising and healthcare as a top-level executive assistant and Direct of Administrative Services leading teams of assistants supporting teams of executives. Through ProAssisting, we are reimaging executive assistant support for today’s business leaders.

Q. What inspired you to (start a new business venture) or (to make significant changes in an existing business)? How did the idea for your business come about?

ANSWER: ProAssisting was created in 2009 as an assistant training program aimed at teaching recent college grads how to work as an executive assistant to get a job in an industry they are passionate about as an assistant and then get promoted from within after excelling as an assistant. We decided to pivot ProAssisting to a remote executive assistant company in 2018 when we realized that technology allowed us to “do what we do” remotely for client instead of working for a single organization in an employee / boss relationship. We developed our business model based on the 3-to-1 executive to assistant ratio that worked so well for us as we managed teams of assistants support executives.

Q. What three pieces of advice would you give to budding entrepreneurs?

ANSWER: 1. A twist on a current business model may be all that you need to create a successful business instead of re-inventing the wheel. 2. A service based business surrounding something that you know a lot about is a good place to start to think about starting a business. 3. Understand that patience and persistence are both key if you truly believe in the business idea you’re pursuing.

Q. What would you say are the top three skills needed to be a successful entrepreneur?

ANSWER: EB: 1. The ability to manage stress and fear as you’re starting out. 2. An understanding of sales and how people make purchasing decisions. 3. An open mind.

Q. To what do you most attribute your success?

ANSWER: My ability to learn from past mistakes and business failures has been a positive influence on our current success. It may have been hard to see at the time and as you’re going through it but failure can make you stronger. Persistence + perseverance combined with an ability to accept that something isn’t work is kinds like holding two competing ideas in your head but if you can do that, you’ll be ahead of the game. Lastly, leverage technology so you can do more with less time.

Q. How do you go about marketing your business? What has been your most successful form of marketing?

ANSWER: We market our business on LinkedIn -in multiple ways-, Google Adwords and have used outside sales representatives when we were first getting started. Currently we’re having the most success with Google Adwords and referrals from current clients.

Q. Where did your organizations funding/capital come from and how did you go about getting it? How did you obtain investors for your venture?

ANSWER: We are fully self-funded and have been profitable from day one. We attribute this to both myself and co-founder (who is also my wife) actually doing the work ourselves to get the ball rolling and have been building from there. If you don’t have to take outside funding we suggest holding on to as much equity as possible.

Q. What is the best way to achieve long-term success?

ANSWER: We thought we were on the road to long term success and then COVID hit. While COVID is a positive for our business given how far remote work and the acceptance of remote work has come in such a short time, in the beginning and middle of COVID, it was a huge headwind. Now we feel like we’re on the road to long term success again but who knows what black swan event is around the corner.

Q. Where you see yourself and your business in 5 – 10 years?

ANSWER: Servicing 1000s of client.

Q. Excluding yours, what company or business do you admire the most?

ANSWER: Apple, The Four Seasons, Any of Danny Meyer’s restaurants, Any company that strives for a high level of hospitality.

Q. How important have good employees been to your success?
ANSWER: Our remote executive assistants are independent contractors and we are very selective about who we decide to partner with but without them, our business wouldn’t run. They are VERY important.

Q. How long do you stick with an idea before giving up?
ANSWER: If data can be gathered, I like to have enough to see a trend to make any decisions. If data can’t be gathered, it’s more of a gut feeling.

Q. How do you generate new ideas?

ANSWER: Generating ideas isn’t the problem… they come all of the time. Letting ideas go and having the wherewithal to make that decision is the key.

Q. How do you define success?

ANSWER: Being able to spend my time how I want to.

Q. How do you build a successful customer base? EB: We clearly define the service we offer and the expectations surrounding that service. Then, we make sure our remote executive assistants are aligned with those same expectations so they can meet and exceed them.

Q. What is your favorite aspect of being an entrepreneur?

ANSWER: The freedom it offers in how I focus my energy and time.

Q. What has been your most satisfying moment in business?

ANSWER: It’s always satisfying when a prospective clients totally gets what we’re all about and sells themselves on what we do… It means we’re on the right track and to keep going.

Q. If you had the chance to start your career over again, what would you do differently? ANSWER: I would have moved to LA to continue my path in the entertainment industry instead of staying in NYC to work in advertising. No regrets but if starting over…

Q. How has being an entrepreneur affected your family life?

ANSWER: Fortunately, it has been a big positive for us in that we work from home remotely and are always available for our kids, but we know we’re not the norm for fellow business owners so we’re continually grateful.

Q. What is your greatest fear, and how do you manage fear?

ANSWER: That our business stops “working” and we can’t put our finger on exactly why.

About: ProAssisting has 34 years of top level EA experience has shaped our model of providing the best comprehensive support possible in our remote executive assistants.