Skip Wilson is the founder of Draft Advertising, a revolutionary wholesale advertising company that helps businesses tackle every aspect of the advertising journey. From campaign planning and strategy to media buying, negotiation, creative design, and more, Draft Advertising manages the nitty-gritty of marketing so companies can focus on (and enjoy) the results.
Before founding Draft, Skip continually ran into customer pain points surrounding results–and was frustrated when he couldn’t answer their questions. Motivated to give his clients a better experience, he drafted revolutionary software that would eventually evolve into the business he runs today. After a few ‘oh shit’ moments, Skip and his team discovered their big ‘aha’ moment that has carried them to success.
What inspired you to start your company?
I got tired of repeating the same phrases and answering the same questions with clients. The first phrase was telling clients they’d notice results after month three–there’s some truth to that, which I’ll get into in a little bit. The second was actually answering the question, “What kind of results can we expect?” That’s normally a very reasonable question, right? For instance, if I ask my financial advisor the same question, they might confidently say I can expect a 7% annual return on my investments.
In the marketing world, it’s more of a wild guess. And I hated not having an answer.
So, I wanted to find out all that information and bring it into one place for people to reference. It blew my mind that it didn’t already exist. There wasn’t a single place where you could do your planning by checking out the return on ad spend and those types of things. I wanted to build a tool that would help calculate, for example, how many clicks an ad campaign would generate so marketers could plan their campaigns.
Any lessons learned that you would like to share?
The biggest piece of advice I would say would be to be super empathetic. That means constantly listening to feedback from customers and employees. If you've got an angry or combatant client, that's actually somebody you can learn a lot from. Yes, they might be an asshole, but they also
might be an asshole with really good advice that nobody else is telling you. So, radical empathy would be lesson number one.
Beyond empathy, being disciplined is the second lesson. The root word of discipline, disciple, means ‘to teach.’ So, discipline, therefore, means ‘teaching yourself.’ Working on yourself, making yourself better. I literally keep a list of things that I want to change about myself. I’m always looking
for self-improvement. And empathy and discipline go hand-in-hand. You want to be empathetic so that you can learn what needs to change and then be disciplined to work on and change those things.
Our motto is, “where ‘aha’ meets ‘oh shit’.” Tell us about your biggest aha! And oh, shit moments.
One of the biggest ‘oh shit’ moments was just realizing that our whole company was based on a premise that no one was willing to pay for. We began marketing the company as a SaaS tool for marketing and media buying agencies, but we quickly realized that the companies we were marketing to didn’t have the budget for our tool. These companies were already spending almost six figures a year on resources. Our tool was the ultimate nice-to-have, not a need-to-have.
We had a lot of people ask us if we could just use our technology to answer the questions for them, and that’s when we realized we had a bigger opportunity on our hands to manage the research and execute for these companies. What people wanted was actually an easy button. I think that was the biggest ‘aha’ moment: if your product is still a nice-to-have, maybe it’s just not taking enough things off people's plates.
If you could hit rewind, is there anything you would do differently?
I’m big on making self-deprecating jokes. However, I realized how damaging that can be when you're the leader of a company.
About four months ago, I said in an offhand, joking way that we might go out of business tomorrow. I meant it as a joke, of course–some shit would really have to go wrong for that to be the case. It'd be zombie apocalypse-level for that to happen. But making that kind of joke when you're the leader of a team is not a good idea. Your team and your employees have their own stuff to worry about. But now the leader of the company has just casually dropped that it might go out of business tomorrow. Not great.
Did you have any “game-changing” resources or tools that helped you start or grow? Why was that resource a game-changer for you?
The Unstoppable Journal makes a huge difference. It not only tracks my appointments and those types of things but also makes sure that I'm getting the right sleep, making sure I'm taking the right supplements, etc.
For example, if I stay awake till 1:00 or 2:00 AM working on something, I’ll kill my productivity for the next couple of days. That doesn't matter as much if you're just riding the clock, but when you're steering the ship, that's a huge deal. The Unstoppable Journal helps me pay attention to things like that.
Where do you go for inspiration and resources?
I’m an avid reader of audiobooks. I face a unique challenge due to my dyslexia, which makes reading difficult for me. But I love audiobooks. I listen to about seven at a time, averaging almost one book per day. While I do enjoy spiritual literature as a Christian, a significant portion of my audiobook collection comprises business books.
One book that has had a significant impact on me is "Profit First." Despite its misleading title, it is actually an essential accounting book that emphasizes the importance of ensuring you get paid at the end of the day. This book really enlightened me about the financial realities of running a business, and I often come across instances where businesses neglect these crucial principles. Recently, a friend of mine was considering buying a franchise, and upon analyzing the books, I had to deliver the unfortunate news that it may not be a profitable venture. "Profit First" helps equip founders who may lack formal business accounting experience with the knowledge necessary to make informed decisions.
Another recommendation I have is "Unstoppable," a book that has resonated with me and offers valuable insights. This book does a good job of mixing health and business advice. To be truly unstoppable in business, you’ve got to prioritize all aspects of your health, mental, physical, everything. Losing a week of productivity due to a seemingly minor setback like strep throat can have a significant impact, particularly in the early stages of building a business. 'Unstoppable' sheds light on these realities and offers guidance on how to navigate such challenges."
What do you want your company to look like a year from now – from the market, your product or service, your team or people, the culture, or revenue?
A year after launch, we crossed the 1 million mark. I’d like to hit the 5 million milestone by the end of this year. That’s different than our projected number. It’s more like our “if everything goes well” number, but that’s the number I’m trying for.
We’ve heard from founders about the difficulty of shifting to being seen as a leader or having a CEO mindset. What have you experienced from your perspective?
I went in with naivety thinking, “I've managed teams, I've built my own department, I've handled profit and loss. That's all there is to running a business. All I gotta do is do that again, right?”
I would've said I had done all of it. The big difference is doing all of that without having a strong company culture. Before, I would've said things like company culture and having your own brand didn't matter at all. Anytime I would hear talk about company culture, I would roll my eyes. But when you lose it, you realize, “Oh wait, that actually does matter a whole lot.”
So, I realized that I had to build that, or we were going to end up as a company of assholes. It’s easy to go off the rails if you don't set parameters upfront. If you think corporate politics and those types of things are bad, which they are in large companies, it's even worse when you don't have
them in small companies.