5 Key Steps To Being a Successful Small Business Owner

Editor’s Note: Last month, the New Leaders Council named this year’s “40 under 40” — a group exemplifying “the spirit of political entrepreneurship.” Below is a piece from Dr. Amy Gershkoff, co-founder and CEO of Changing Targets Media, a Washington, DC–based consulting firm. Amy shares with us the five key pieces of advice she received about how to start and run a successful small business.

By Dr. Amy Gershkoff

Nearly two years ago, my boss asked me if I would like to start a small business together.  His idea was to take some media buying software I had developed and market it to political campaigns.  He would provide some of the start-up capital and I would run the business day-to-day.  

It was pretty much any person’s dream career scenario: full-scale leap from Senior Data Geek to CEO all in one day.  I couldn’t wait to get started.

Today, our firm, Changing Targets Media, boasts half a dozen full-time, smart, dedicated staff, and more than 50 clients, representing some of the most high-profile campaigns in the nation.  We have received numerous accolades and words of praise, including more than a dozen endorsements from prominent leaders in the Democratic political community.  We’ve been featured in several major news outlets including a profile in the Washington Post and a segment on ABC News.  And to cap it all off, I was recently honored with the New Leaders Council’s “40 Under 40 Progressive Leadership Award.”

But the road there was not easy.  My background was in statistics, but it soon became apparent that my days of developing interesting math algorithms had largely passed and had prepared me very little for the challenges of running a business.  My day-to-day problems began to revolve around budgets, contracts, lawyers, IT, insurance, human resources, marketing, sales, staffing — most of which were areas in which I had little or no experience.

As I navigated this difficult terrain during the last two years, I have often turned to other smart, talented women to seek advice.  Below I share with you the five most valuable pieces of advice I received about starting and running a successful small business:

1.  “Don’t be afraid to ask for help.”  
Starting and running a business is hard, and doubly (or triply) so for women.  But resources abound, and lots of help is available if you’re willing to ask.  During my first six months running Changing Targets Media, I took several successful business owners out to lunch and asked them for advice on a wide range of business topics. I joined numerous associations and networking groups for business owners, including several email listserves, as well as LinkedIn and Facebook groups for entrepreneurs.  Each of these forums has provided me with opportunities to learn from other business owners.

2.  “Don’t walk in looking like you’re waiting for your first big break – walk in like you’ve already had your first big break.”  
Confidence is everything.  If you don’t feel confident about what you’re selling, why should anyone buy your product?  On the other hand, if you appear confident, and as though the sale would be nice but not necessary, you become more appealing.  (It’s the business equivalent of the oft-repeated “playing hard to get” mantra in dating.)  

3.  “Buy lunch.” 
Sales and marketing are critical to making a start-up business successful.  When it comes to pitching, office meetings are all well and good, but when you take a prospective client to lunch, you have their undivided attention for at least an hour.  They are away from their computer, their phone, their email, their colleagues and their staff — and that means you have a better chance of getting your message across.  

4.  “Find a good lawyer; put him or her on speed dial.” 
For any small business owner, a good lawyer is mission-critical.  Since most lawyers are expensive, especially if they are good, many small business owners decide to save money by triaging some early legal work themselves.  But this is a dangerous way to be penny wise and pound foolish, especially if the person or organization you’re negotiating with has an actual attorney doing the legal work on their end.  As my lawyer is so fond of reminding me, you can either pay your lawyer on the front end to provide good advice, or you can pay him five or ten times that amount to dig you out of a mess you got yourself into because you were too cheap to pay him on the front end.

5.  And last but not least, a valuable piece of advice I was taught back in preschool that still very much applies in my life today: “Treat people the way you want to be treated.”  
Whether it’s your staff, your vendors, your colleagues, or your clients, you can never go wrong if you observe the Golden Rule.   

Dr. Amy Gershkoff is co-founder and CEO of Changing Targets Media, a Washington, DC – based consulting firm.

More 40 Under 40 Winners:

Amanda Terkel

Erin Switalski

Tracy Van Slyke

Stephanie Schriock



Tom S.
Past Member 2 years ago

Your blog is extremely brilliant especially the quality content is really appreciable.
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Merna S.
Merna S7 years ago

This gives me hope that you started a business without a business background. I'm in the same boat and it feels like a steep learning curve so relieved to hear that business owners are willing to share their expertise (with the incentive of lunch!). I like the personal learning and having like a team of "mentors" around. Thanks for the tips!

Beng Kiat Low
low beng kiat7 years ago


steve g.
steve graci7 years ago

Nice tips but you forgot to mention any tips on finding a financial backer with enough cash to get you started (Like you had) or a bank willing to loan you enough, or venture capitalists willing to listen. Hire a lawyer? Buy everyone lunch? You must be kidding. You apparently were lucky enough to get a free ride allowing you to become a generous tipper.

Beng Kiat Low
low beng kiat7 years ago


gail d.
gail dair7 years ago

thanks for post

jill bukovnik
jill Campbell7 years ago

I'm an artist who has had successful shows with my art. I'm a painter and carver. This year my partner and I would like to move to Vancouver Island where I plan on starting my own business. Thank you very much for the tips that you gave me. I'll remember them as my dream keeps developing.

Pam K.
Pam K.7 years ago

I am in the process of getting my business off the ground.Thanks for the tips!

Jessica H.
Jessica H7 years ago

thanks for the tips!

Petra Luna
Petra Luna7 years ago


and the sister company....