6 Millennial CEOs Share How They Closed Their First Six-Figure Deal

Early success requires a surprising amount of persistence.

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By Serenity Gibbons

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No entrepreneur ever forgets the rush from that first deal or the first sale you closed. If nothing else, it was the milestone when you realized that your idea, product, or startup was viable and that there was a customer -- and demand -- for what you created.

For millennial entrepreneurs who achieved that milestone while still under the age of 30 (or even 20) that milestone may be even more momentous. That's because you are defying the odds of what is considered to be an acceptable age for an entrepreneur who can bring a legitimate service to the marketplace.

I asked six millennial CEOs who have founded successful companies about what that first deal was like for them and what lessons we could learn.

1. Richard Lorenzen, Founder & CEO of Fifth Avenue Brands

"My first large client (although I didn't know it yet) came from a connection I made on an online forum for entrepreneurs (this was before the days of Facebook!). He was seeking a digital agency for help marketing his consulting firm. I was a small, one-man agency at the time and he took a chance on me with a small deal. I proved myself by getting results consistently. Within six months that small deal turned into a six-figure contract!"

Lesson: You never know which lead, no matter how small, could quickly become your largest client (and best source of referrals). That's why you must look at every lead as the deal of a lifetime no matter how it turns out.

Pro Tip: Leverage all channels to mine for leads and don't assume one will be more useful than another. That means creating a marketing strategy that combines offline and online platforms to reach out to your target audience.

Related: 5 Unique Traits of Millennial Entrepreneurs

2. Erik Huberman, Founder & CEO of Hawke Media

"I made my first sale with my company, Swag of the Month. We had hit a point where we needed to either raise money to scale it or we needed to sell it and fortuitously. During this time, we had caught a local holding company's eye. They called me, asked a few questions, and made a cash offer. I accepted and picked up a check two days later."

Lesson: Don't give up on getting that deal because it will come and at the most unexpected time.

Pro Tip: Continue to market across all channels even when you are not sure what the future will hold. Be proactive in seeking out those potential customers with messages that show why you are different and what adds value related to their specific need or desire.

3. Shama Hyder, Founder & CEO of The Marketing Zen Group

"I closed our first sale the same way we close all our business now: via social media. It has always been important to me that we walk our talk at Marketing Zen, which is why we've never done any outbound marketing. Our clients find us now, just like our first client found us then! I had been blogging, creating content, and sending out our newsletter when our first client found us and called. I remember being thrilled because we closed the deal after just that first initial call."

Lesson: Your ongoing conversations with your target audience are building credibility and trust that will eventually convince them to buy from you. Have patience and keep talking to them.

Pro Tip: During these social media conversations, take the time to catalogue the main topics that get the most responses or feedback among all your social media content. Use these for future content ideas to continue emphasizing what your audience seems to be the most interested in.

Related: Looking for a New Payment Company? You're 'Due' for Some Good News.

4. Chalmers Brown, Co-Founder & CTO of Due

"I snagged our first large client during a conference the co-founders and I were attending. We had a chance to demo our solution in front of the entire audience there and it caught the attention of a company that had been struggling with their legacy systems for invoicing and payments. It was a great environment to make the sale in because it led to other sales in the coming weeks. This approach has worked time and time again since then at other conference demos."

Lesson: Being able to get in front of your targets and show them a live example of how you solve their problem makes selling so much easier.

Pro Tip: Spend time developing and practicing your demo in front of other people before presenting it at a conference. This gives you the time and ability to determine what messaging will be the most engaging and will resonate with your audience. Those you practice with can give you tips on what would be the most convincing.

5. Chirag Kulkarni, Founder & CEO of Taco

"My first deal was with a local business in Kansas City. I convinced the future customer that he could get more business if he outsourced his online marketing to me, and that's how I got my first deal. Essentially, I proved to him that if he paid me a certain amount, he could double it (and he did!)."

Lesson: The key to closing your first deal oftentimes is being bold and putting your money where your mouth is. If you're going to do that, you better have the performance to back it up. Don't make an offer if you can't deliver!

Pro Tip: Have quantitative evidence that you can deliver on these promises by illustrating how your solution can solve a particular need and then quantify that need in terms of benefits it will offer. It could be cost and/or savings, revenue increases, etc. In essence, you will need to show, not tell.

Related: From $0 to Millionaire: How 6 Entrepreneurs Went Broke, Then Became Successful

6. Nate Robertson, Co-Founder of Square Ship

"When you're first starting out, you need to do a lot of things that are uncomfortable. Cold calling or other forms of outbound sales is one of them. I hated sales calls because they always felt so painful. However, as an entrepreneur with a startup, these sales calls were very necessary. I persisted until it became another habit. The moment that happened was when I landed my first deal."

Lesson: Keep doing it until it gets easier. The more calls you make, the less scary it becomes. Your confidence will also grow as you close deals and get accustomed to the process.

Pro Tip: Working with a mentor can help you get over the fear of making sales calls and can provide a plan of attack and script to guide you through the process. A mentor can also offer constructive criticism and the necessary pep talks to get you through these difficult tasks.

Serenity Gibbons

Equal Rights Advocate, Promoting Amazing Companies Across the Globe

Serenity Gibbons is a former assistant editor at the Wall Street Journal and a New York University alumna living in California. She is the local unit lead for NAACP in Northern California with a mission is to ensure the political, educational, social and economic equality of rights of all persons and to eliminate race-based discrimination. She enjoys writing and interviewing people who are making a difference in the world. 

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