How To Start A Business Broke: Hat Secrets | Jennifer Magley

The ground shook under my feet as he dropped the atomic truth bomb on me: he had been cheating since day one. 

Two days before my dream business was slated to open this confession rocked my world. Unexpectedly and instantly I became a single mother of two children (ages 1 and 3) with precisely ZERO income. There were no investors in my business or VC guys lining up to write checks. My small business was built through shear hustle, cold calls, and the grace of God. I had transformed a $1,500 tax return into an actual business in less than four months leading up to the surprise of my life.

While my personal life was incinerated that Friday, there was no way I could back out of opening my business, a full page piece in The Indianapolis Star was to print that Sunday. “Onward,” I whispered as I watched my future ex-husband drive away.

Picture that evening as the dust settled and the aftershocks began.

I was splayed on the ground of the shower like road kill. Devastated. Eyes swollen and face buzzing post anxiety attack. Oddly I had temporarily lost the ability to form words. Every time I tried to speak the words came out as though I was partially deaf. The edges of a mental break began tugging at the front of my mind. So much pain, so broken.

While my reality had been shattered nothing stung more than realizing I fact…literally…and totally…actually now: BROKE.

If this is you or one of your greatest fears, alas I am here with good news: you too can start a business with zero dollars.

The many hats entrepreneurs had to wear to get where they are today are often left backstage. Since they have “arrived” there is no Instagram Live or Facebook Live to capture their younger selves doing their side gig while giving guru advice. Unfortunately, no one seeks out the fry guy for insight.

Yet behind all the glitz, glamour, and glory is a sometimes neglected story of grit. If you plan on being an entrepreneur or going for your greatest dream here is a little discussed secret: you must wear many hats.

Hat #1: Hustler

Colonel Sanders (KFC) was a steam engine stoker, insurance salesman, and filling station operator.

Meghan Markle wrote calligraphy for wedding invitations.

Dwayne “The Rock” Johnson slept on a used mattress he found from the garbage behind an hourly sex motel.

Tyler Perry lived out of his car.

Do what you need to do to make ends meet. 

For me it has meant an array of things from GoodWill flipper to working on trade for food. That’s right. “Will work for food” is a real thing. I once consulted with a food service company in return for meals. If you want something bad enough you will become creative. The word creative can also be swapped for humble when you have a need. Be open to odd work and more work to supplement your dreams.

Hat #2: Lobbyist (Stalker)

In order to connect with the person, place, or thing that will help take one to the next level, one must implore their eh hmm “strategic thinking.” As a high performance coach and speaker I still use the techniques I developed cold calling for donation diapers as a teenager. I refer to it as “High, Low, Circular.” In essence, attempt to contact your main target (the highest level.) If they do not respond or their contact information is not available then go to the lowest person (power wise) within the organization. Typically there is as a figurative “open door” within the lower ranks. Finally IF, this does not yield the desired connection, go circular.

Going circular means drawing a circle around your target and seeing where the connecting points are. Then meet these second level connections until the circle is complete. At some point the target in the middle will hear about your business from their connections and want to meet you, often feeling out of the loop. Hence, meeting you became their idea.

Jesse Itzler, NY Times best selling author, co-founder of Marquis Jet, a partner in Zico Coconut Water, AND owner of the NBA’s Atlanta Hawks is a master at this. He most famously wore a bottle of Zico Tetra Pack during the 2013 NYC Marathon. For those non-active readers that is 26.2 Miles dressed as a bottle.

Do what you need to do, authentically, to get to the next level.

Hat #3: Salesman

ABC Baby. Always Be Closing. Here are some phrases to get comfortable with:

What are you looking for in x?

Is there any reason why this does not work?

Can you see the benefit of?

And one of my all time favorites:

I hear you saying you do not know, if you did know, what would you say?

Ask, ask, and ask again as though your life depends on it. In truth it does. Ask and ye shall receive or ask until you do. Famed sports agent and entrepreneur David Meltzer has a practice of asking until he gets told “No” three times. After the second no he typically receives a yes. Furthermore, you will be remembered by the giver.

This is often referred to as “The Benjamin Franklin Effect.” In Wikipedia language, “a person who has already performed a favor for another is more likely to do another favor for the other than if they had received a favor from that person.” For those who love inflated diction think “cognitive dissonance.”

Starting a business with little to no outside capital is frankly the only way for some. Mark Cuban boldly proclaimed in 2013 “Only morons start a business on a loan…with so many uncertainties in starting your business the only certainty is paying back your loan.” When taking the leap of entrepreneurship get that head ready because the hats will keep coming. Most often the success of your venture has more to do with your willingness to wear odd hats than having money.

Jennifer Magley is a former professional athlete, speaker, author, and High Performance Coach. Article originally appeared on More information can be found at and videos on YouTube.