Work-At-Home Success Profile: Milo Shapiro


Milo Shapiro left his I.T. career in 2000 to start IMPROVentures, which offers team-building and motivational speech programs using improvisation games.  In 2004, at the request of numerous attendees, Milo began offering coaching in public speaking skills (in person and via Skype).  That originally-secondary program has become more than half of his business today.

1) How did you get started working from home?

Because I was looking to do events hosted by clients, which would be held at their facilities or hotels, it just didn’t make sense to run the business from a store front, paying rent there, when my second bedroom could easily serve as an office.

2) How did you choose the work-at-home career you do?

I had grown bored with my cubicle job and the office politics game.  I wanted to be more in control of my success without the limitations of a boss telling me what was expected in their corporate culture.  Specifically why I chose to bring improv to business people was because of my passion for the fun of improv and because I’d already seen so many people who’d taken improv classes flourish in other areas of their life; improv teaches us to listen better, build upon the ideas of others, creatively problem-solve, and more.

3) How did you get started (basic initial steps)?

A website, a brochure, and letting everyone I knew know.  Then I began contact HR departments and offering my services at ridiculously low rates in order to build a loyal following.

4) How did you get your first client or customer or job?

I wrote to several companies whom I wanted a foot in the door of and said that I’d do my first team-building for free to the first company to get back to me, committed to booking.  It actually only took about two weeks before Computer Sciences Corporation said, “Really?  For free?”

5) How do you market your business?

SEO is huge.  Yelp helps a lot.  Speaking yields audience members who want to bring me into their companies, especially if I can speak at professional associations.  I love when I get referrals from past clients who know someone who wishes they spoke better or who runs events at their own companies.  Asking for those referrals instead of hoping for them really makes a difference.

6) What does your usual day look like?

What’s a usual day?  Some days are booked with clients wanting me to help them be better at speaking.  Some days I’m customizing a speech for another client.  Some days I’m working on proposals for conferences I’d like to speak at.  Some are all about networking or attending conferences to let more people know about me.  Others are just about website development, working on a newsletter, or actually trying to data enter the piles that build up.  No two days are similar.

7) What do you know now that you wish you knew when you started?

Start building your mailing list from Day 1.  You’ll always put it off thinking you don’t have enough interest yet, but if you start from the outset, it’ll slowly build.

8) What advice would you give someone who wants to work from home?

Brace yourself: You’ve just merged your personal life and business life.  Unless you have the stomach to not resist answering the phone and email at both 6:30am and 10:30pm (and I haven’t got that defense yet), you are ALWAYS on.  So feel no guilt if you want to do a little Facebook or go for a walk in the middle of your workday because you will likely be doing way more than 40 hours a week anyway.  And prepare your family for these realities.  You aren’t “home” just because you’re home anymore.  Sound awful?  Then don’t do it.  Personally, and maybe because I love what I do, I wouldn’t consider going back to a cubicle just so that I could feel done at 5pm again.  And my commute is about 12 feet from my bed! 

Website: IMPROVentures

Twitter: @miloshapiro

Facebook Page: IMPROVentures

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