Jackson Cunningham

Jackson is the founder of tuft + paw, a modern DTC brand for cat people that has grown to over 8 figures in sales. Prior to starting tuft + paw, Jackson started several other ecommerce brands in the fashion space.

Where did the idea for tuft + paw come from?

We had just adopted our own cat and we live in a small apartment in an expensive. After shopping for a litter box, we couldn’t believe there wasn’t any nicer options. We didn’t want to bring junk into our small apartment and felt like there had to be a better way 🙂

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

I wake up, make a coffee and then stroll to WeWork a few blocks away. In the mornings, I try to tackle the most important big thing on my list. In the afternoon, I do more quick task-based activities including emails (which I try to check only once per day). I only book meetings on Wednesdays and Thursdays to keep the other days free to do deep work.

I use Asana for my tasks, and have lots of recurring weekly and monthly tasks which show up on my daily to-do list. On Fridays, I organize and prioritize my upcoming week’s tasks.

How do you bring ideas to life?

It’s important to step back from the busyness of work every once in a while and look at the bigger picture so you can figure out the non-urgent, but important things you can do for your business. I find it really hard to think deeply on the same day as I’m rapid firing emails and tasks. So it’s important to make time to think of the big ideas.

Once I have an idea, I try to validate it as quickly as possible. For example, making a presale on a potential new product. This gives us the confidence and motivation to persevere with all the hard work that it’s going to take. For bigger ideas, I think it’s really important to build momentum with small victories along the way. You just need to take it one step at a time and recognize that it’s going to be a long journey.

What’s one trend that excites you?

Remote work. One of the reasons I started this business was to become more location independent and I love that I can offer that to everyone on our team now.

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

Batching emails so that I only receive new emails once per day. And batching tasks so that I do similar style of tasks at once (for example, all banking activities on Mondays). It reduces the mental fatigue of switching between tasks.

What advice would you give your younger self?

Think bigger. When I was younger, I started a few online stores that were so niche because I felt it would be impossible to fail. While that was somewhat accurate, I didn’t realize how limited I’d be if I actually succeeded – once the businesses had grown to a certain point, they couldn’t get any bigger. I wish I had focused on building businesses in bigger markets that had more potential for growth, even if there was more competition.

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

“Play it by year” makes more sense than “play it by ear”.

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

Take action. Stop reading, stop meeting people for coffee. Just start your business and you’ll learn 100x more.

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

Cold outreach for PR. I hire an Upworker, send them a list of 50 major publications, and ask them to find the most recent article on that site about X (x can be anything related to your business, e.g. ‘startups’). Then I ask the Upworker to get the name and email of the author of that post, I email the author offering them free products with no strings attached. I keep track of all these contacts, and usually we end up getting some great free media coverage. But I focus on the long term, with no expectations up front.

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

We almost ran out of money at one point. I assumed I could raise money from our existing investors, but they pushed back and it almost devastated our business. I ended up working 80 hour weeks and securing funding from new investors, but I learned a really valuable lesson. Never assume you can get outside money, and plan accordingly with financial forecasts.

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

An agency that makes creative (videos) for tiktok and facebook ads. This is a perfect mix of art and science that is very difficult for brands to find right now. Everyone is spending money on Facebook and TikTok ads, and the most important part is the video and figuring out 1) how to get people to thumbstop and pay attention (hook) and 2) how to sell your product (benefits that convert).
There are agencies that do this, but the really good ones are hard to find. If someone builds a business that focuses only on the actual creative production, and they do it well, they will grow a ton from word of mouth alone.
Start by offering your services for free to a few brands.

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

I spent $10 to get some bike chain lubricant. I’m a casual biker, and I can’t remember the last time I lubricated my chain. I bought a can and it makes my rides so much smoother.

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

Boomerang for gmail. It allows me to disappear emails so that they return at a later time in the future. This allows me to get distractions or larger tasks out of my inbox, and batch similar style tasks (ie. all customer care emails on friday).

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

I love the book “how to get rich” by Felix Dennis (terrible name, great book – it’s not about getting rich, but more around the perils and downsides of being rich and lessons learned about money).

What is your favorite quote?

Done is better than perfect.

Key Learnings:

• Get started on your business even if you don’t feel ready. You’ll learn more by doing.
• PR outreach can be a great way to grow your business in the early stages
• Batch similar tasks in order to stay productive and avoid distractions
• Dream big! Any good business idea is going to take a long time, so you might as well focus on something that has the potential to grow.