Business Mentoring Series – Setting Yourself Up for Success


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By the time Jesse Maddox quit his corporate job he had the idea for what would eventually become TripLingo close to finalized, but success wasn’t a foregone conclusion. Now, the question was how would he fund it? Jesse says, “I had about $200 to my name.” His friends set him up with a potential investor and Jesse flew to the meeting, expecting to come home with a check in his hand. Jesse relates his feeling to Fran, “This was my chance… so I went and printed out this 50-page business plan in full color — which cost me about a third of my net worth at the time.”

At the meeting, the potential investor asked Jesse, “so who’s working on this with you?” When he found out it was just him he pushed Jesse’s business plan aside and ended the meeting. “It was kind of a chicken and egg problem,” Jesse says. “I needed money so I could hire a team. No, I needed a team so I could get money. That was the lesson I took out of that meeting.”

Related: Business Mentoring Series – From Corporate Job to Small Business Ownership

So Jesse started looking for people to join his team and launch his business. Eventually, Jesse’s hard work led and persistence to a lucky break and his business took off.

In this lesson you will learn:

  • How to pitch an idea to investors
  • The value of preparation
  • Why you need a leadership team when looking for investment
  • How hard work leads to lucky breaks

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Harry Kierbow

Harry Kierbow

Harry Kierbow is the Director of Social Media for Commissions Inc (CINC), a real estate technology and marketing company. He's played professionally on Facebook (and other social networks) for more than 7 years now, managing campaigns for brands (both big and small) and individuals (also both big and small). Universally regarded as the greatest ice hockey goalie to ever come from Griffin, GA (by his mom at least), you can find Harry between the pipes on the ice rinks of Georgia (yes, there is more than one) or playing with his 2 kids when he's not perfecting social media ads or binging true crime documentaries on Netflix. Connect with Harry on LinkedIn @HarryKierbow.