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Learn from my successes and mistakes: Tips from entrepreneur and Scratchpad board member Shannon Kin

Shannon Kinney, Founder and Client Success Officer of Dream Local Digital, walked into the room, wrote some numbers on a whiteboard, set the board aside, and jumped into her talk.

Shannon Kinney first made a splash in the business world with her foresight into the opportunities for online marketing in what was then a new digital world and tech. She made her mark by assisting in the development and growth of from a seven-employee operation to a 500-person well-oiled in 157 markets machine in just eight months.

Today, Shannon has 7 startups under her belt, sits on the board of advisors for several; companies (including Scratchpad), has Dream Local Digital offices and customers in 68 cities, and is mom to a personable 8 year old girl. She regularly works with brands like Google, Facebook, LinkedIn, Twitter and media companies throughout the world. She has also worked with Microsoft, eBay, CareerBuilder,,, Netscape and many more.

Scratchpad was fortunate enough to welcome Shannon to our offices last month to hear about her career and influential experiences—and how our 2017 cohort can learn from her successes and failures as she embarked upon creating scalable businesses.

Read on for six of Shannon’s most valuable lessons:

Lesson 1: Appreciate the Pivot

“How to be proud to tell your story, even if it’s not your first story.”

During her time in Silicon Valley, Shannon had the opportunity to meet a tech firm that proposed a business plan that revolved around creating a professional dating site. Their pitch did not fit their personality, and Shannon turned them down because she did not feel the story that led them to their idea fit the people that were presenting it. Though a good start, it needed to be reworked to fit their expertise. This was their company’s pivot, and they took this advice to change their original pitch, and make it fit who they were. Years later they are able to boast that they have become incredibly successful; in part thanks to the rejections they faced.

When presenting your pitch, investors need to feel your story before they can be interested in your numbers. They’re investing in you, your values, and their perception of your ability to execute your plan. To make your pitch fit your personality, your idea needs to reflect your passion, and what experiences led you to it are those that shape your company. It is your inspiration, and investors like to be inspired. Even if you are married to your original idea, always be open to the opinions of those that may turn you down. Appreciate the pivot, because the advice and rejection you get from others is how your startup shapes the story that gets others on board, even if it’s not the first story that you had.

Lesson 2: Protect Your Equity

“Especially women founders, because we tend to undervalue ourselves.”

At eBay, Shannon had the opportunity to buy the company a large share of stock from a tech firm they had been trying to acquire. This effectively gave eBay a huge share of ownership of a company whose founder had worked for eight years to build. This founder had no part in this sale and, it turned out, was against it giving away so much of his work. This happened because—despite his passion for his business—he had made the mistake of trusting his key team members with large shares with no stipulations about how or when they could trade them. Because of this lack of foresight, his businesses partner was able to go behind his back to complete the deal. The founder did not protect his equity, and that gave someone else the opportunity to take advantage.

Shannon’s advice: Protect your equity fiercely. This starts with knowing your worth to a company or cause and enlisting the help you need in order to wield your power. Negotiate terms with your stockholders and team members because, in the end, you’re the one with power. To Shannon, this lesson is especially relevant for women business owners, like Scratchpad entrepreneurs, because women generally tend to undervalue themselves. It is crucial that women do not make this mistake with their equity and set contractual stipulations that prevent others from taking advantage of them. If employees or investors with options want out, make sure you get to decide how they leave.

Lesson 3: Find People who Believe in the Dream

“Asking questions is how you find answers.”

Starting a business is no small task. It depletes your savings and energy and is a true test of will. Which means it is crucial to find the right team members who take personal stock in your dreams and goals and have the drive to help you accomplish them. When Shannon first started building her team, she met a woman with skills and abilities comparable to hers who seemed completely caught up in the dream and passionate about the same ideas. The two made great friends and shared a passion for the space, so Shannon didn’t probe any further. When they started working together, Shannon quickly learned that they disagreed on many aspects of the business, including pricing and scale, and found they were at odds with each other on a regular basis. Her team member only wanted to put in her hours, go home at five, and receive health benefits – she was looking for a job vs. creating a scalable business. That was not Dream Local. Within 28 days of realizing this, the woman was working elsewhere. As Shannon puts it, “She didn’t have the desire to build a large-scale business.” There is a difference between creating a job for yourself or a few others and creating a business, and it’s critical that you know going in what your team members are on the same page. In two subsequent situations, it was bringing in team members that didn’t share the same work ethic.

Shannon now recognizes her mistake: She letting her predisposition of attributing positive opinions of people until proven wrong affect her judgment, and by not seeking deeper alignment on vision for the future and goals. Even though there was shared passion for the business with these people, there wasn’t alignment in how to build for the future. First impressions are misleading, and even if you could see yourself working with someone, that doesn’t mean that they are a fit for your growing business. Shannon advises our female founders to dig deep to find people who are willing to put in the work and who genuinely believe in your cause by digging deep. Ask the important questions, like: “Where do you see yourself in 10 years?” Don’t just talk about the dream; learn more about the individual you are hiring. Relying on gut feelings, or how knowledgeable or personable someone seems, is not enough. When it comes to your money, there is no give and take, only the right and wrong fit for your company.


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