Dawson Whitfield – Founder and CEO of Logojoy

I make a point to regularly take time to deliberately motivate myself…I vividly picture things and that really amps me up to get there.

Dawson Whitfield is the founder and CEO of Logojoy, an online tool that uses artificial intelligence to design beautiful, custom logos. He founded Logojoy after experiencing frustration creating logos for clients, thinking there must be a better way. He now runs the daily operations of the fast-growing startup.

Where did the idea for Logojoy come from?

I’ve been a designer for about 13 years, most of that time was spent doing branding for small businesses. Last summer I was doing a logo for a client and I just felt like a glorified font picker – not to mention they spent $3,000, and the whole process took about 3 weeks. I honestly felt like I was just getting in the way – which was hard for me because I really take pride in the work that I do.

I knew there had to be a better way for people to just get a beautiful logo. I couldn’t find a solution, so decided to build it myself.

What does your typical day look like and how do you make it productive?

My day is mostly split between three things – a) meetings with people on the marketing, product, and CS teams to make sure they are having the most impact possible, b) thinking about the future of the product and design, and c) high level business planning like financial planning, org structure, etc.

I make my day productive by writing every single to-do down. It’s easy to lose focus when your job requires you to do 50 things every day, but I find it really helps to write down every single to-do that pops up.

How do you bring ideas to life?

By inspiring others to take the ideas to life. Once the team gets to a certain size, you can no longer get your hands dirty with the actual work, so it’s critical to be able to inspire others to take ownership of the project.

I make sure to pick the right person, communicate why the idea is important, and give them as much autonomy as possible. I do my best work when I feel like I own the project, so I make sure to give full ownership.

What’s one trend that really excites you?

This whole ‘side hustle’ trend is incredibly exciting. I think people are so much happier if there is something in their life that they own, and if done properly, can bring a much more fulfilling life. It’s also a happy coincidence that one of our biggest markets is that same ‘side hustle’ market.

What is one habit of yours that makes you more productive as an entrepreneur?

I make a point to regularly take time to deliberately motivate myself. I imagine what would happen if we released a feature tomorrow that doubled conversion rates. I imagine how big our office will be in two years. I imagine seeing a team of 100 incredibly smart, happy team members celebrating a big investment round. I vividly picture things and that really amps me up to get there.

What advice would you give your younger self?

Embrace chaos. Embrace the fact that shitty things will happen. Prepare for business-threatening things to hit you every month. Understand that it’s a marathon and if you let stress overcome you, you won’t enjoy it, and no amount of money is worth spending 5 years of your life in agony.

Tell us something that’s true that almost nobody agrees with you on.

Often ‘important’ things come up that people think I’m crazy for ignoring. I’ve learned that there is a certain amount of care and stress that you have bandwidth for in the day, and some things just aren’t worth it. My dog got bit the other day and everyone said I should make a fuss with the other dog’s owner, but I just didn’t have the bandwidth for more stress in my life, so I didn’t bother.

As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?

Be the last to talk. Always let people, especially the people under you, get their thoughts out first. They will feel heard and respected, they will also feel like you really respect their perspective. Once I started doing this, I learned that there’s almost always something that I did not think about. I had a bad habit of assuming I always knew right, but oftentimes, people that have thought about it more, know better than you.

What is one strategy that has helped you grow your business?

SEO accounts for 65% of our revenues, and it’s free traffic. We understand that SEO is a long game and we took the risk of investing time into it early. We consistently create great content and products that people love to share. We’ve especially found success with micro-sites like How To Make a Logo. Micro-sites are extremely share-able, and also link-able, which is key for SEO.

What is one failure you had as an entrepreneur, and how did you overcome it?

I spent two years and my life’s savings working on a project that failed miserably. I overcame it by classifying it as a learning experience. It sucked, but I thought to myself, “Okay, now I’m really ready to make something work”. Coming out of that failure I had tried about every single growth hack and conversion optimization. I knew that once I had a company with product-market fit, I would kill it. And that’s exactly what happened.

What is one business idea that you’re willing to give away to our readers?

I actually tried this idea briefly before Logojoy and thought it really had legs. It would be a mobile website that let’s anyone add stickers to a photo. It would be used by brands to promote certain things. For example, Universal Studios would send their audience to a mobile website where they can apply a Minions filter to their photo and post it on a social network with #minions hashtag. By posting a photo with a hashtag, they would be entered into a competition to win.

What is the best $100 you recently spent? What and why?

Hiring someone to write an article for $100 off Upwork is a great investment. I personally don’t like writing articles, and an article can be worth much more than $100 for SEO purposes.

What is one piece of software or a web service that helps you be productive? How do you use it?

Trello is a nice one to keep track of what everyone is working on. We all have our cards assigned to ourselves and it really helps keep everyone focused and productive. I find if everyone knows what everyone else is working on, people are generally more productive as they are now accountable for their tasks.

What is the one book that you recommend our community should read and why?

The Hard Thing About Hard Things is a great one that gives a no-bullshit insider perspective on building a startup. It’s written by Ben Horowitz, who is a legendary investor.

What is your favorite quote?

“Today is the oldest you’ve ever been, and the youngest you’ll ever be again”. This reminds me to embrace things in life everyday. It reminds me to be young and enjoy my youth, but also that every day there is an expectation to grow and be better.

Key Learnings:

  • Do something you feel incredibly passionate about. Scratch your own itch.
  • Embrace life as it comes, don’t let the stress get to you. Make sure you’re enjoying the journey.
  • Keep yourself motivated. You should always take time to make sure your mental health is in order and you’re loving the day.


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