How to Get Your First Big Win in Business

Six entrepreneurs look back on how they earned that pivotal first "Yes!"
How to Get Your First Big Win in Business
Image credit: Michele Marconi
Magazine Contributor
4 min read

This story appears in the March 2019 issue of Entrepreneur. Subscribe »

1Bait the hook.

“When my cofounder, Hari Karunanidni, and I started HackerRank -- a platform to help companies hire developers -- we created a fake résumé with perfect credentials and posted it on job boards. We got a slew of inbound calls from recruiters looking for this amazing candidate. Once we had them on the phone, we’d say, ‘Hey, I’m not that person, but people like this are all over the world, and you don’t need a résumé to find them.’ It was a risky strategy, but it worked: That’s how we landed one of our first enterprise customers.” -- Vivek Ravisankar, cofounder and CEO, HackerRank

2Follow up.

“The year I launched Splendid Spoon, I spoke on a startup panel at Brooklyn Brewery and met two buyers from FreshDirect, who were in the audience. Their headquarters was across the street from my incubator kitchen, so I followed up by dropping off samples. A few weeks later, they asked me to develop some local soup flavors for them. I am always knocking on doors -- you get lots of noes, but that one yes makes all the difference.” -- Nicole Centeno, founder and CEO, Splendid Spoon

Related: 3 Myths About Success That You Need to Stop Believing This Year

3. Tell the truth.

“At Smart Furniture’s first presentation to venture capitalists, one candid slide got us funded. It had these words in bold: HERE’S EVERYTHING WE SCREWED UP. I thought that leveling with investors at the outset would be key, and it was -- it helped build instant trust.” -- Stephen Culp, founder, Smart Furniture, and cofounder and CEO, PriceWaiter and Delegator

4. Overprepare. 

“I cold-called the national buyer at Kroger -- the largest grocery chain in the U.S. -- for several weeks straight. One day he picked up, and I dove right into my pitch. He tried to get rid of me by asking me to send him some materials later, but I had already emailed him that very information, so while I had him on the phone, I asked him to check his inbox! After about five minutes, he agreed to test our product in 100 stores. Today, we sell our entire line across 2,000 locations.” -- Neel Premkumar, founder and CEO, Forto Coffee

Related: Want Startup Success? Keep It Simple, Stupid!

5Get real.

“Breather’s challenge was getting landlords on board with a crazy idea: that anyone with a mobile phone could book workspace in their building, on demand. We finally found one who agreed to give us a shot -- and then she quickly changed her mind. I walked to her office and literally got on my knees and begged. I told her that if we didn’t do the deal, I was going to be fired. Nearly five years later, that space is still on the Breather network. Sometimes you can’t be too proud to beg.” -- Packy McCormick, VP of experience, Breather

Related: 8 of the Biggest Mistakes Entrepreneurs Make When Presenting to Investors

6. Take a risk.

“I launched Supergoop! in 2007, and by 2009, we needed a strategic retail partner to scale. I’d been in touch with a merchant at Sephora years earlier, but she felt we needed to grow first. Now the timing was right, so I left her a voicemail saying I’d be in San Francisco the next week and wanted to meet. She never returned my call, but I flew out anyway -- with no other plans -- and hoped she would call back. I checked into a tiny hotel room with no windows, and my cellphone lit up. My future buyer said, ‘Holly, can you come in tomorrow morning at 10 a.m.?’” -- Holly Thaggard, founder and CEO, Supergoop!

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