'I interviewed 39 times at Goldman Sachs before I got the job': Entrepreneurs share the most extreme things they did to land a dream role


job interview

  • What’s the boldest thing you’ve done to get a job?
  • Five business leaders were asked this question, and their answers (some more extreme than others) reveal daring approaches to landing that dream career.
  • For instance, CEO Sharran Srivatsaa interviewed for a position 39 times before he finally got it.
  • Visit Business Insider’s homepage for more stories. 

Applying for a competitive job? Sometimes it pays to take risks. Here are the boldest things these business leaders and advisors in The Oracles did to land a job or client.

SEE ALSO: 7 highly successful leaders share the top advice they wish they could go back and tell their younger selves

1. I wrote a $25,000 check

Years ago, I was already established and wanted to work with a famous business icon. When I learned that he occasionally offered mentoring, I decided this was my chance. I emailed his assistant, who told me it would be $25,000 to get started. I sent the money as soon as I could scrounge it together. He called the next day and said he couldn’t believe that I sent the money without meeting or speaking with him. 

I flew to meet him a week later. He told me to write a sales letter and call him the next afternoon if I finished it. I called him an hour later, and he rushed over. He reviewed my work and asked why I paid him so much when I already knew how to do the work. I explained that I just wanted to work with him on a business deal. He told me that I was crazy, and we went on to do many deals and make a lot of money together. When someone creates a paid channel to access them, seize the opportunity. You never know what might happen!

Roland Frasier, principal of 30 businesses, including War Room Mastermind and Traffic & Conversion Summit; host of the “Business Lunch” podcast; connect with Roland on Facebook, LinkedIn, and Instagram


2. I showed up at the HR office unannounced

When I graduated from college, I decided I wanted to work in New York City, Los Angeles, or Chicago. I bought three plane tickets and had 90 interviews. When I say interviews, I mean I was also interviewing the companies. Ultimately, I decided I was into journalism and Time Inc. was the place to begin my career. 

I looked up the head of human resources and showed up at his office. I now realize how crazy that sounds; but at the time, I just thought I was being proactive. His assistant asked me if I had an appointment and I politely said no, but I really had to speak with him. Against all odds, he invited me into his office, and I had my first job working at Time magazine soon after.

—Kara Goldin, founder and CEO of  Hint Inc.; creator of The Kara Network, a digital resource for entrepreneurs; and host of the “Unstoppable” podcast; follow Kara on Twitter and Instagram

3. I visualized getting the job

When I first read about visualization in the book “The Secret,” I thought it was nonsense. However, after visualizing myself drinking a cup of coffee and getting a free lunch when I was homeless, and both of my visions materialized, I became a believer in the technique. So, I aimed for a job. I visualized how good it would feel to get paid, have a bed to sleep in, and shower daily. But I didn’t just sit around and wait — I took action. I started asking around town about job openings. On the second day, I landed a job as a marketing executive.

I realized that there is a connection between what we visualize in our minds and the reality we create with our actions. Through visualization, we can strengthen our brainwaves and connect what we desire with our physical ability to achieve it. This may sound unrealistic and even a little crazy. I thought so too at first. However, once I understood the power of visualization, I couldn’t stop myself from dreaming in full color.

Andres Pira, real estate developer, founder, and CEO of Blue Horizon Developments, and author of “Homeless to Billionaire: The 18 Principles of Wealth Attraction and Creating Unlimited Opportunity” (available on Amazon and Kindle); follow Andres on Facebook, Instagram, and YouTube 

4. I interviewed for the position 39 times

After I earned my master’s degree, I wanted to work on Wall Street. Almost everyone I spoke with told me two things about getting a Wall Street gig. First, get ready for a grueling and stressful process. Second, it is nearly impossible to get a job with Goldman Sachs, so don’t even bother. 

So, naturally, I set my sights on Goldman Sachs. I had no idea what was in store. It took 39 one-on-one interviews in multiple cities to get the job. That doesn’t include phone calls, coffee meetings, lunches, dinners, and my favorite: being thrown out of a managing director’s office. There were times I thought they were doing this just to see how long I could stay in the game. That was a pivotal experience that taught me endurance and has helped me become a better entrepreneur.

Sharran Srivatsaa, CEO of Kingston Lane  and mentor to top entrepreneurs; grew Teles Properties 10x to $3.4 billion in five years; follow Sharran on Instagram

5. I gave away $20,000 of my time

Always lead with value. A few years ago, I wanted to get to know a particular real estate influencer I admired and take over his marketing. So I sent him an awkward Facebook message. My offer was simple: I would give him $20,000 of marketing and related services for free. My goal was to get results and earn an endorsement from him. 

I helped him transition to the right kind of deals and taught him how to buy directly from homeowners in a competitive market the correct way. He profited over six figures, invited me on his podcast, and emailed his followers about me. We are still friends today, and his encouragement is one of the big reasons I started mentoring. Talk about a win-win!

—Ryan Dossey, real estate broker and investor who owns more than 125 rental units across the Midwest; founder of Call Porter and Ballpoint Marketing, and partner at Stewardship Properties 

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