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How to Learn From High-Quality Failures
21st May 2015 • Hack the Entrepreneur • Jon Nastor
00:00:00 00:28:36

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My guest for today is the founder and Client Success Officer of Dream Local Digital, a startup helping small-medium sized businesses market themselves online.

She has over 15 years of experience in digital marketing, sales, and product development. She has worked with media companies focusing on internet product development and digital revenue growth.

She is considered an expert in the field of digital marketing and social media.

My guest is a sought-after speaker and speaks across the country about social media and online marketing.

Now, let s hack …

Shannon Kinney

In this 28-minute episode Shannon Kinney and I discuss:

  • How being open to meeting a lot of people helped grow her business
  • Always staying in touch with people in her network
  • Why you can’t work in your business and on your business
  • Dreaming big and creating a scalable solution
  • Having a team that’s strong, where she’s not

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The Show Notes

The Transcript

How to Learn From High-Quality Failures

Jonny Nastor: This is Rainmaker.FM, the digital marketing podcast network. It’s built on the Rainmaker Platform, which empowers you to build your own digital marketing and sales platform. Start your free 14-day trial at

Voiceover: Welcome to Hack the Entrepreneur, the show which reveals the fears, habits, and inner battles behind big-name entrepreneurs and those on their way to joining them. Now here is your host, Jon Nastor.

Jonny Nastor: We are back with another episode of Hack the Entrepreneur. Thank you so much for joining me. I’m your host, Jon Nastor, but you can call me Jonny.

My guest for today is the founder and Client Success Officer of Dream Local Digital, a startup helping small to medium-sized businesses market themselves online.

She has over 15 years of experience in Internet marketing, sales, and products.

My guest speaks all across the country about social media and online marketing. Now she’s here.

Now, let’s hack Shannon Kinney.

Let’s thank our sponsor FreshBooks. FreshBooks is the easy-to-use invoicing software designed to help small business owners get organized, save time invoicing, and get paid faster — expense tracking, time tracking, estimates, quotes, reports. When you can’t figure something out, they have absolutely phenomenal, award-winning customer support. You can actually call them and get somebody on the phone to help you.

Stay on top of your business with a clear picture of its financial health. Try FreshBooks for free today. Go to and enter ‘Hack the Entrepreneur’ in the ‘How did you hear about us?’ section.

Welcome back to Hack the Entrepreneur. We have another very awesome guest.

Shannon, thank you so much for joining me today.

Shannon Kinney: Thank you for having me.

Jonny Nastor: It is my pleasure. Let’s jump straight into this, shall we?

Shannon Kinney: Sure.

Jonny Nastor: Shannon, can you tell me, as an entrepreneur, what is the one thing that you do that you feel has been the biggest contributor to your successes so far?

How Being Open to Meeting a Lot of People Helped Grow Her Business

Shannon Kinney: Staying in touch with your network and being open to meeting a lot of people helps you in every role in every company that you’re in, particularly when you’re an entrepreneur. This business, Dream Local Digital, I found the thing that’s made me the most successful is that you can’t work ‘on’ the business and work ‘in’ the business at the same time.

My best practice here is to hire a strong leadership team, and allow them to do just that — allow them to lead. I empower them to run their departments and shape the company. That way I can focus on growing the business. Then because of that, it’s grown.

Jonny Nastor: Smart. I like it. There are two things there. Staying in touch with your network — I’m going to be a bit selfish because this is something that I feel that I definitely don’t do very well, especially now. I reach out to and I get to talk so many smart people, like yourself, and I feel I should be nourishing that in some way. How do you go about nourishing a network and staying in touch with them?

Always Staying in Touch With People in Her Network

Shannon Kinney: It’s much easier now with social media. My first startup was We had a team and clients and people all over the US, and I used to send cards and notes and emails and calls. Now, I do it largely through social media. On my entrepreneur side, a lot of it is Twitter, a lot of it’s LinkedIn.

It’s a disciplined approach to staying in touch with a lot of people, monitoring what’s going on with them so that, when and if you do get to talk, you’ve got a good sense of where they’re at. For me, I dedicate a certain amount of time to that every single day in terms of staying in touch with people.

The other key thing is I try to give more than I take. If anybody asks me for help and I’m capable of giving it, I try to jump in and do that because it always pays benefits.

The last part is I really think long range when it comes to my network. If somebody upsets me or a deal doesn’t go the way I want or something like that, you’ve got to just let it go because you’ll be surprised throughout your life how people come back into it. I find that giving more than you take always provides the best win in the long run.

Jonny Nastor: Yeah. Give more than you take definitely. I agree with that. The next part was you said that you can’t work ‘on’ your business as well work ‘in’ it. Did you know this? Did you bring experience from past places and know this going into Dream Local Digital?

Why You Can’t Work in Your Business and on Your Business

Shannon Kinney: That’s a good question. I did. In past jobs that I’ve had, I tried to, in businesses that I’ve started, I’m the kind of person who loves to jump in to the weeds. I have a lot of skills in the ops area. I love that part of the business, but I recognize that my business will stay small if it relies on me in those roles. It was a real lesson for me for this startup, which is my own money — or it was until 2013 — it’s no longer all my own money.

When I started that way, I recognized that it was really critical for me to build the future and build the legacy, not something that was just a job for myself. I’m fortunate that — if I look back at all my decisions that I made — that one decision was probably the one that was the real foundation to us getting as far as we have so far.

Jonny Nastor: Nice. I love it. Shannon, there’s a time in every entrepreneur’s life when they realize one of two things — either they have a calling to make something big in the world or they simply can’t work for somebody else. Can you tell us which one of those two you are?

Dreaming Big and Creating a Scalable Solution

Shannon Kinney: That’s an interesting point. I am definitely somebody who wants to make something bigger. I experienced that in this company where, initially, I had somebody working with me at a partner level. It was clear that really what she was looking for was a job she loved. We came to a crossroads really early in the relationship where I was like, “This isn’t about a job you love unless I’m going to go take the business in a direction and you’re going to work here.” That’s not how you grow a business.

For me, it’s always been about dreaming bigger and creating a scalable solution that can create a lot of jobs and tremendous value for our customers. I think there’s a real difference between people who do that and create a job. People who create a job, that’s important work, too. It’s just very different than trying to create something that’s bigger.

Jonny Nastor: Nice. Have you been as the leader and as an entrepreneur previously, though? Was this something that you’ve grown up in, or did your family come from that? Or is this something that you worked in like and did these other startups and then were ready to take the plunge yourself?

Shannon Kinney: I’ve been in the Internet space since the mid ’90s. I was lucky enough to be on the ground level of several startups — was one — as a key leader or person building it and making it happen. For me, I learned something new at every one of those experiences.

This one’s the first one that was something I started myself on my own. We’re now funded and have a terrific team of people who dream the same dream that I dream. It’s a very different thing when the company gives you a lot of money and says, “Build this.” That’s still a startup, but it’s an entirely different thing than, “Wow, build this or eat. Build this or buy something.”

It takes a fortitude that you don’t anticipate. Any time you think, “Well I can go two years without making money.” Whatever your estimate is, triple it, and recognize it’s going to require strength that you never thought you had — but to make it happen, it’s so gratifying. It’s so gratifying.

Jonny Nastor: Excellent. OK, Shannon, we’re going to move on to work. You have quite a team behind you now working with you. You haven’t created a job but you’ve created a business that isn’t all remote workers. It’s all located in Maine where you are, right?

Shannon Kinney: That’s right. About 80 percent of our employees are using one of our offices. They’re disparate, but the majority of them are in Maine.

Jonny Nastor: Excellent. I want to know now how you work. Today’s a work day. You started out, say, the first 30 or 60 minutes with probably some sort of a routine to set yourself up to get the things done that you need to get done today in your business. Could you walk us through that routine?

Her ‘Secret Sauce’ to Getting Things Done

Shannon Kinney: Sure. The first 30 minutes of my day are pretty critical. I also have a young daughter. I get up at 5 am and start working for two hours before she’s up and before I go into the office. My first 30 minutes, I do two key things. One is I try to use that time for creative work — anything that requires strategic thinking, a creative idea, planning, or anything I’m going to be doing. If I’m presenting to a team and trying to inspire them, I try to do that in the first 30 minutes.

The biggest enemy is that desire that wants to check all your notifications and check your email. Every time I start the day doing that, it’s a worm hole that all of a sudden my daughter’s awake. It’s time to go, and I’m running out of the house. So my first 30 minutes, I really try to think bigger about something creative and leverage the fact that I’m fresh and it’s the beginning of the day.

I used to be a really avid to-do-list person. I still have to-do lists — my team will be laughing when they listen to this — but I really practice the thought about what is your next action and really thinking the next action and focusing on that. Rather than this big to-do list like, “Conquer the world,” it will be, “OK. Here’s what I’m doing to do that today.” If I need any assistance in getting my next action list together for the day, that will probably happen in the first 30 minutes.

Jonny Nastor: Oh wow, nice. You do set it up in the morning, sort of assess what needs to be done. I know lots of people are telling me the night before they have to set up that, “what I’m going to do tomorrow,” or else it just falls apart on them.

Shannon Kinney: It’s so true, but if I find that at the end of the day or the night before, I’m not very fresh. I may look at my calendar or a list of things in a more negative light and be daunted, whereas first thing in the morning I’m like, “Oh I got this. This isn’t so bad.”

The one thing I will look at is my calendar so that I know where I’m supposed to be and roughly what’s going to happen during the day. I try really hard to only think about what are the actions to get through that day, not look at every message, because I drown in those things.

Jonny Nastor: I love that. I love the confidence in it. Lots of people like it the night before, and you just know that you’re not that fresh at that time. You like it in the morning because it sets you up, and that’s I think what you need to do. You need to find out how you work.

Shannon Kinney: That’s right. Some people are night owls. I like to do social things at night.

Jonny Nastor: Exactly. I like that. And that segues us in — so you are organized, you get up early in the morning, and you know how to stay in touch with your network. Now, every blog post, every expert out there in the world right now is telling us the 80-20 rule — do the 20 percent that gives you 80 percent of the results. Do what you’re good at and delegate the rest. Shannon, can you tell us something in your business that you’re absolutely not good at?

Having a Team That’s Strong Where Shannon Isn t

Shannon Kinney: There’s two big things. One of them is I like to do the strategic planning and direction on where revenue is coming from — working closely with the customers to help the revenue. I have a director of operations who is brilliant at creating budgets, forecasts, making sure that the accounting is all done appropriately. She does a number of other amazing things as well, but she stays in touch of what happens once the money comes in and how all of that works. She and our accountant are really great at that, and that’s not my gift.

I think recognizing where your gifts are and where they aren’t and creating a team that complements you versus just says ‘yes’ to you all the time is a really key decision that you make running a business. I’m lucky that I have a team that supports me in those really well. It also pays to just have your ego in check and be like, “Hey, I know I’m not the smart one about this,” and look to those people to do it.

The other one is managing my calendar. It seems a very high maintenance situation, but I get so many requests or things or people trying to fit in my calendar that I could spend half the day answering emails and looking at my calendar and get nothing done.

It was key for me to finally accept that I needed to delegate that to someone else. It was hard for me because I don’t necessarily love the tone it sets with people who are trying to talk to me, but on the other hand, they get responded to. They get responded to way more quickly and efficiently than if it was relying on me to do it. Those two are the ones that have probably made the biggest difference in the business.

Jonny Nastor: That’s really interesting. It seems like they’re two very, very important things. By the way you described it, it sounds the first one with the revenue and taking control of the money once it comes in was something you knew in advance that you needed. Then it sounds the second one was something that you were kind of forced into because you realized you were doing it.

Shannon Kinney: I learned it. The numbers one, as an entrepreneur, you always have to know your numbers. You have to know them. You have to own them. You have to be part of making them happen, but I do that at a strategic level and as an owner of a business level. I understand that it’s not my gift in terms of from that high level, down to the street, and I’m very fortunate to have a team that is really strong where I am not.

Jonny Nastor: That’s awesome, and yeah, you’re right. You have to know those numbers. I find a lot of people struggle with putting somebody into that position earlier on because they’re more looking at generating that revenue — which isn’t always right — rather than controlling that revenue as it comes in because that’s really what usually sinks or allows the company to continue on. We’re always like, “No, we need people like sales people. We need marketing. We need people who will get us more sales.”

Shannon Kinney:...